JPH0258258B2 - - Google Patents
Info
- Publication number
- JPH0258258B2 JPH0258258B2 JP842184A JP842184A JPH0258258B2 JP H0258258 B2 JPH0258258 B2 JP H0258258B2 JP 842184 A JP842184 A JP 842184A JP 842184 A JP842184 A JP 842184A JP H0258258 B2 JPH0258258 B2 JP H0258258B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- compounds
- halogenated
- halogen
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 platinum group metals Chemical class 0.000 claims description 139
- 238000006243 chemical reaction Methods 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 43
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 33
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 29
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 24
- 239000004202 carbamide Substances 0.000 claims description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims description 16
- 239000010948 rhodium Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 14
- 150000002366 halogen compounds Chemical class 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 12
- 150000002828 nitro derivatives Chemical class 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 9
- 229910001882 dioxygen Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 229910052703 rhodium Inorganic materials 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 150000003868 ammonium compounds Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910001507 metal halide Inorganic materials 0.000 claims description 5
- 150000005309 metal halides Chemical class 0.000 claims description 5
- 150000004010 onium ions Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012495 reaction gas Substances 0.000 claims description 2
- 150000008045 alkali metal halides Chemical class 0.000 claims 1
- 150000002941 palladium compounds Chemical class 0.000 claims 1
- 238000000066 reactive distillation Methods 0.000 claims 1
- 150000003284 rhodium compounds Chemical class 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- 150000003672 ureas Chemical class 0.000 description 44
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 24
- 150000001340 alkali metals Chemical class 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000002723 alicyclic group Chemical group 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- KATOLVAXCGIBLO-UHFFFAOYSA-N 1,3-dibenzylurea Chemical class C=1C=CC=CC=1CNC(=O)NCC1=CC=CC=C1 KATOLVAXCGIBLO-UHFFFAOYSA-N 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000003673 urethanes Chemical class 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical class [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 125000000962 organic group Chemical group 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical class C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 150000004677 hydrates Chemical class 0.000 description 5
- 229910000765 intermetallic Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 150000004714 phosphonium salts Chemical class 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 101150003085 Pdcl gene Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001174 sulfone group Chemical group 0.000 description 4
- 125000003375 sulfoxide group Chemical group 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052792 caesium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910052714 tellurium Inorganic materials 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- BFLWAUWLGJKDMJ-UHFFFAOYSA-N 1-butyl-3-ethylurea Chemical compound CCCCNC(=O)NCC BFLWAUWLGJKDMJ-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
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- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
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- UXZFQZANDVDGMM-UHFFFAOYSA-N iodoquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(I)C2=C1 UXZFQZANDVDGMM-UHFFFAOYSA-N 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- QNPFDIMIWRIIHK-UHFFFAOYSA-K lanthanum(3+);tribromate Chemical compound [La+3].[O-]Br(=O)=O.[O-]Br(=O)=O.[O-]Br(=O)=O QNPFDIMIWRIIHK-UHFFFAOYSA-K 0.000 description 1
- BULVJAIIOVREOT-UHFFFAOYSA-K lanthanum(3+);triiodate Chemical compound [La+3].[O-]I(=O)=O.[O-]I(=O)=O.[O-]I(=O)=O BULVJAIIOVREOT-UHFFFAOYSA-K 0.000 description 1
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- 239000007791 liquid phase Substances 0.000 description 1
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- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
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- NNNSKJSUQWKSAM-UHFFFAOYSA-L magnesium;dichlorate Chemical compound [Mg+2].[O-]Cl(=O)=O.[O-]Cl(=O)=O NNNSKJSUQWKSAM-UHFFFAOYSA-L 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
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- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
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- FVSUYFWWFUVGRG-UHFFFAOYSA-N naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)N)=CC=CC2=C1 FVSUYFWWFUVGRG-UHFFFAOYSA-N 0.000 description 1
- IYRGXJIJGHOCFS-UHFFFAOYSA-N neocuproine Chemical compound C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 IYRGXJIJGHOCFS-UHFFFAOYSA-N 0.000 description 1
- SEHRUTVBKBCDGC-UHFFFAOYSA-K neodymium(3+);triiodate Chemical compound [Nd+3].[O-]I(=O)=O.[O-]I(=O)=O.[O-]I(=O)=O SEHRUTVBKBCDGC-UHFFFAOYSA-K 0.000 description 1
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- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- IPVBXZMWDWJWHR-UHFFFAOYSA-N nitrocyclobutane Chemical compound [O-][N+](=O)C1CCC1 IPVBXZMWDWJWHR-UHFFFAOYSA-N 0.000 description 1
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- CJSZWOGCKKDSJG-UHFFFAOYSA-N nitrocyclopentane Chemical compound [O-][N+](=O)C1CCCC1 CJSZWOGCKKDSJG-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
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- TWLXDPFBEPBAQB-UHFFFAOYSA-N orthoperiodic acid Chemical compound OI(O)(O)(O)(O)=O TWLXDPFBEPBAQB-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- DUXDETQJUQZYEX-UHFFFAOYSA-L oxalate;rubidium(1+) Chemical compound [Rb+].[Rb+].[O-]C(=O)C([O-])=O DUXDETQJUQZYEX-UHFFFAOYSA-L 0.000 description 1
- PZKNFJIOIKQCPA-UHFFFAOYSA-N oxalic acid palladium Chemical compound [Pd].OC(=O)C(O)=O PZKNFJIOIKQCPA-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 1
- RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
- NEEYQSLHJZSEKP-UHFFFAOYSA-I pentasilver pentaoxido(oxo)-lambda7-iodane Chemical compound [Ag+].[Ag+].[Ag+].[Ag+].[Ag+].[O-]I([O-])([O-])([O-])([O-])=O NEEYQSLHJZSEKP-UHFFFAOYSA-I 0.000 description 1
- LLYCMZGLHLKPPU-UHFFFAOYSA-N perbromic acid Chemical class OBr(=O)(=O)=O LLYCMZGLHLKPPU-UHFFFAOYSA-N 0.000 description 1
- HSAJRDKFYZAGLU-UHFFFAOYSA-M perchloryloxymercury Chemical compound [Hg+].[O-]Cl(=O)(=O)=O HSAJRDKFYZAGLU-UHFFFAOYSA-M 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical group O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- SKJJGBRWKOFYAD-UHFFFAOYSA-N piperidin-1-ylurea Chemical compound NC(=O)NN1CCCCC1 SKJJGBRWKOFYAD-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- FJVZDOGVDJCCCR-UHFFFAOYSA-M potassium periodate Chemical compound [K+].[O-]I(=O)(=O)=O FJVZDOGVDJCCCR-UHFFFAOYSA-M 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 description 1
- UJQKSBYNVKHMFX-UHFFFAOYSA-N potassium;hypoiodite Chemical compound [K+].I[O-] UJQKSBYNVKHMFX-UHFFFAOYSA-N 0.000 description 1
- ACAYDTMSDROWHW-UHFFFAOYSA-M potassium;iodic acid;iodate Chemical compound [K+].OI(=O)=O.[O-]I(=O)=O ACAYDTMSDROWHW-UHFFFAOYSA-M 0.000 description 1
- KVOIJEARBNBHHP-UHFFFAOYSA-N potassium;oxido(oxo)alumane Chemical compound [K+].[O-][Al]=O KVOIJEARBNBHHP-UHFFFAOYSA-N 0.000 description 1
- VXLUZERCXISKBW-UHFFFAOYSA-M potassium;perbromate Chemical compound [K+].[O-]Br(=O)(=O)=O VXLUZERCXISKBW-UHFFFAOYSA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- SBOLKCRPTBJXQW-UHFFFAOYSA-N propyl n-cyclohexylcarbamate Chemical compound CCCOC(=O)NC1CCCCC1 SBOLKCRPTBJXQW-UHFFFAOYSA-N 0.000 description 1
- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
- MZVRPCYUUFGMLJ-UHFFFAOYSA-N pyrrolidin-1-ylurea Chemical compound NC(=O)NN1CCCC1 MZVRPCYUUFGMLJ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229940102127 rubidium chloride Drugs 0.000 description 1
- 229910001952 rubidium oxide Inorganic materials 0.000 description 1
- LACSDIAFVPRAER-UHFFFAOYSA-M rubidium(1+);bromate Chemical compound [Rb+].[O-]Br(=O)=O LACSDIAFVPRAER-UHFFFAOYSA-M 0.000 description 1
- GZXRGRLACABJNC-UHFFFAOYSA-M rubidium(1+);chlorate Chemical compound [Rb+].[O-]Cl(=O)=O GZXRGRLACABJNC-UHFFFAOYSA-M 0.000 description 1
- CWBWCLMMHLCMAM-UHFFFAOYSA-M rubidium(1+);hydroxide Chemical compound [OH-].[Rb+].[Rb+] CWBWCLMMHLCMAM-UHFFFAOYSA-M 0.000 description 1
- QUXRPHKFJTZUIH-UHFFFAOYSA-N rubidium(1+);hypoiodite Chemical compound [Rb+].I[O-] QUXRPHKFJTZUIH-UHFFFAOYSA-N 0.000 description 1
- CIOUAZZDKTZOPK-UHFFFAOYSA-M rubidium(1+);iodate Chemical compound [Rb+].[O-]I(=O)=O CIOUAZZDKTZOPK-UHFFFAOYSA-M 0.000 description 1
- VSKZPMJZTZBXCF-UHFFFAOYSA-M rubidium(1+);periodate Chemical compound [Rb+].[O-]I(=O)(=O)=O VSKZPMJZTZBXCF-UHFFFAOYSA-M 0.000 description 1
- JNFXLBYFDYRNBF-UHFFFAOYSA-K samarium(3+);tribromate Chemical compound [Sm+3].[O-]Br(=O)=O.[O-]Br(=O)=O.[O-]Br(=O)=O JNFXLBYFDYRNBF-UHFFFAOYSA-K 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- XQLMNMQWVCXIKR-UHFFFAOYSA-M silver bromate Chemical compound [Ag+].[O-]Br(=O)=O XQLMNMQWVCXIKR-UHFFFAOYSA-M 0.000 description 1
- YSVXTGDPTJIEIX-UHFFFAOYSA-M silver iodate Chemical compound [Ag+].[O-]I(=O)=O YSVXTGDPTJIEIX-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- SAFWHKYSCUAGHQ-UHFFFAOYSA-N sodium;hypoiodite Chemical compound [Na+].I[O-] SAFWHKYSCUAGHQ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- HISNRBVYBOVKMB-UHFFFAOYSA-N stibonium Chemical class [SbH4+] HISNRBVYBOVKMB-UHFFFAOYSA-N 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- NAMOWWYAIVZKKA-UHFFFAOYSA-L strontium bromate Chemical compound [Sr+2].[O-]Br(=O)=O.[O-]Br(=O)=O NAMOWWYAIVZKKA-UHFFFAOYSA-L 0.000 description 1
- YJPVTCSBVRMESK-UHFFFAOYSA-L strontium bromide Chemical compound [Br-].[Br-].[Sr+2] YJPVTCSBVRMESK-UHFFFAOYSA-L 0.000 description 1
- 229910001625 strontium bromide Inorganic materials 0.000 description 1
- 229940074155 strontium bromide Drugs 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- KRIJWFBRWPCESA-UHFFFAOYSA-L strontium iodide Chemical compound [Sr+2].[I-].[I-] KRIJWFBRWPCESA-UHFFFAOYSA-L 0.000 description 1
- 229910001643 strontium iodide Inorganic materials 0.000 description 1
- UHCGLDSRFKGERO-UHFFFAOYSA-N strontium peroxide Chemical compound [Sr+2].[O-][O-] UHCGLDSRFKGERO-UHFFFAOYSA-N 0.000 description 1
- JKGZNVNIOGGUKH-UHFFFAOYSA-L strontium;diiodate Chemical compound [Sr+2].[O-]I(=O)=O.[O-]I(=O)=O JKGZNVNIOGGUKH-UHFFFAOYSA-L 0.000 description 1
- LPSWFOCTMJQJIS-UHFFFAOYSA-N sulfanium;hydroxide Chemical group [OH-].[SH3+] LPSWFOCTMJQJIS-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000004772 tellurides Chemical class 0.000 description 1
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- OSWMMVUHYHQYCV-UHFFFAOYSA-N tetrabenzylazanium Chemical class C=1C=CC=CC=1C[N+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 OSWMMVUHYHQYCV-UHFFFAOYSA-N 0.000 description 1
- SBCUXVQZGCKZET-UHFFFAOYSA-N tetrabenzylphosphanium Chemical class C=1C=CC=CC=1C[P+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 SBCUXVQZGCKZET-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical class CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KOFMFKMQSQTMTM-UHFFFAOYSA-N tetrakis(4-methylphenyl)phosphanium Chemical class C1=CC(C)=CC=C1[P+](C=1C=CC(C)=CC=1)(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KOFMFKMQSQTMTM-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical class C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- CRUVUWATNULHFA-UHFFFAOYSA-M tetramethylphosphanium;hydroxide Chemical compound [OH-].C[P+](C)(C)C CRUVUWATNULHFA-UHFFFAOYSA-M 0.000 description 1
- PJMJFVQKDBRMIP-UHFFFAOYSA-N tetraphenylarsonium Chemical class C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PJMJFVQKDBRMIP-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical class C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- COGRQAIUMQAJID-UHFFFAOYSA-K tribromocobalt Chemical compound Br[Co](Br)Br COGRQAIUMQAJID-UHFFFAOYSA-K 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- JJPVWQWOOQYHCB-UHFFFAOYSA-N triethyl(phenyl)azanium Chemical class CC[N+](CC)(CC)C1=CC=CC=C1 JJPVWQWOOQYHCB-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- NYKQYQGHJAVHSU-UHFFFAOYSA-M triethylsulfanium;hydroxide Chemical compound [OH-].CC[S+](CC)CC NYKQYQGHJAVHSU-UHFFFAOYSA-M 0.000 description 1
- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical class C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-UHFFFAOYSA-N 0.000 description 1
- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical class [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- BTFMMLSOTLUDGC-UHFFFAOYSA-L zinc diperiodate Chemical compound [Zn++].[O-][I](=O)(=O)=O.[O-][I](=O)(=O)=O BTFMMLSOTLUDGC-UHFFFAOYSA-L 0.000 description 1
- TUDPEWOTGHYZBQ-UHFFFAOYSA-L zinc;dibromate Chemical compound [Zn+2].[O-]Br(=O)=O.[O-]Br(=O)=O TUDPEWOTGHYZBQ-UHFFFAOYSA-L 0.000 description 1
- MFMKGXZULQONRI-UHFFFAOYSA-L zinc;diiodate Chemical compound [Zn+2].[O-]I(=O)=O.[O-]I(=O)=O MFMKGXZULQONRI-UHFFFAOYSA-L 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明はウレタン化合物の製造方法、さらに詳
しくは酸化剤の存在下に尿素化合物を一酸化炭素
及び有機ヒドロキシル化合物と反応させて酸化的
にカルボニル化することによつてウレタン化合物
を製造する方法に関するものである。
ウレタン類はカーバメイト系農薬などに用いら
れる重要な化合物であり、最近ではホスゲンを使
用しないイソシアナート類製造の原料として、そ
の安価な製造方法が要望されている。
このようなウレタン化合物を一酸化炭素を用い
て製造する方法としては、芳香族ニトロ化合物、
芳香族ニトロソ化合物、芳香族アゾ化合物、芳香
族アゾキシ化合物などを酸化剤の不存在下で還元
的にウレタン化する方法および芳香族アミノ化合
物を酸化的にウレタン化する方法が知られてい
る。
さらにN,N′−ジアリール尿素を酸化的にウ
レタン化する方法も提案されている(特開昭55−
120552号公報)。この方法では主触媒として第
族貴金属またはその化合物を用い、助触媒として
塩化銅、塩化鉄、オキシ塩化鉄、塩化バナジウ
ム、オキシ塩化バナジウムなどの、ルイス酸であ
つてしかも反応系においてレドツクス反応を行な
うことのできる金属を含む塩化物を反応系中に溶
解させておく必要がある。しかしながら溶解した
これらの金属塩化物は反応容器や配管、バルブな
どの金属材料に対する腐食性が大きく、このため
高価な金属材料を使用しなければならないという
設備上の問題がある。さらに溶解したこれらの金
属塩化物を生成物である芳香族ウレタンのような
高沸点物質から分離・回収するためには、はん雑
な操作と多大の費用を要するという欠点があつ
た。
また、これらの触媒系を用いる方法では、一酸
化炭素基準のウレタン化合物の選択率が工業的に
実施する上で満足すべきものでなく、特にN,
N′−ジアリール尿素の反応率を上げていくに従
つて、この一酸化炭素基準のウレタン化合物の選
択率がさらに低下していくことも問題であつた。
そこで本発明者らは、尿素化合物を酸化的にウ
レタン化する方法において、先行技術におけるこ
れらの問題点がなく高収率、高選択率でウレタン
を製造できる触媒系を見出すべく鋭意研究を進め
た結果、有効な触媒系を見出し、先に提案した。
これらの触媒系は、白金族金属及び白金族元素を
含む化合物の中から選ばれた少くとも1種と、ハ
ロゲン化合物の少くとも1種とからなつており、
ハロゲン化合物としては臭素又はヨウ素を含む化
合物が特に有効な助触媒であることをも見出し
た。これらの触媒系を用いることによつて、尿素
化合物及び一酸化炭素基準のウレタン化合物の収
率及び選択率を、先行技術に比べて大巾に向上さ
せることができたが、尿素化合物の反応率を例え
ば90%以上に高めていくと、一酸化炭素基準のウ
レタン化合物の選択率が若干低下してくることが
判明したので、この点を改良すべくさらに鋭意研
究を進めた結果、これらの触媒系を用いること
と、反応によつて生成してくる水の全量又は一部
を反応系外に除去しながら反応させる方法とを組
合わせることによつて、一酸化炭素基準のウレタ
ン化合物の選択率がさらに向上するばかりでな
く、反応速度及び尿素化合物基準の収率及び選択
率もさらに向上させることができることを見出
し、これらの知見に基づいて本発明を完成するに
至つた。
すなわち、本発明は、酸化剤及び、(a)白金族金
属及び白金族元素を含む化合物の中から選ばれた
少なくとも1種と、(b)ハロゲン化合物の中から選
ばれた少なくとも1種とから成る触媒系の存在下
に、尿素化合物を一酸化炭素及び有機ヒドロキシ
ル化合物と反応させてウレタンを製造する方法に
おいて、反応によつて生成してくる水の全量又は
一部を反応系外に除去しながら反応させることを
特徴とするウレタンの製造法を提供することにあ
る。
さらに、本発明は、上記の触媒系及び反応方式
に加えて、追加的助触媒として塩基性物質及び/
又はキレート試薬の中から選ばれた少くとも1種
を用いるウレタン化合物の製造法を提供すること
にある。
本発明の特微の1つである、反応によつて生成
する水の全量又は一部を反応系外に除去する方法
としては、実質的に水が除去できればどのような
方法でもよいが、反応蒸留方式で留去する方法、
一酸化炭素を含む反応用ガス又は低沸点有機物質
などの搬送剤による除去法、有機ヒドロキシル化
合物の一部と共に留去する方法及びこれらを組合
わせた方法などが特に好ましい。従つて反応方式
としては、液相は回分式、流通式のいずれでもよ
いが、一酸化炭素を含むガス成分は流通式にする
のが好ましい。
本発明方法において用いられる白金族金属及び
白金族元素を含む化合物については、成分として
パラジウム、ロジウム、白金、ルテニウム、イリ
ジウム、オスミウムなどの白金族元素から選ばれ
た少なくとも1種を含むものであれば特に制限は
なく、これらの元素が金属状態であつてもよい
し、化合物を形成する成分であつてもよい。ま
た、これらの触媒成分は活性炭、グラフアイト、
シリカ、アルミナ、シリカ−アルミナ、シリカ−
チタニア、チタニア、ジルコニア、硫酸バリウ
ム、炭酸カルシウム、アスベスト、ベントナイ
ト、ケイソウ土、ポリマー、イオン交換樹脂、ゼ
オライト、モレキユラーシーブ、ケイ酸マグネシ
ウム、マグネシアなどの担体に担持されたもので
あつてもよい。
金属状態の白金族元素として、例えばパラジウ
ム、ロジウム、白金、ルテニウム、イリジウム及
びオスミウムなどの金属、これらの金属黒、これ
らの金属イオンを含む触媒成分を前記のような担
体に担持したのち、水素やホルムアルデヒドで還
元処理したもの、及びこれらの金属を含む合金あ
るいは金属間化合物などが用いられる。また、合
金あるいは金属間化合物はこれらの白金族金属同
士のものであつてもよいし、他の元素、例えばセ
レン、テルル、イオウ、アンチモン、ビスマス、
銅、銀、金、亜鉛、スズ、バナジウム、鉄、コバ
ルト、ニツケル、水銀、鉛、タリウム、クロム、
モリブデン、タングステンなどを含むものであつ
てもよい。
一方、白金族元素を含む化合物としては、例え
ばハロゲン化物、硫酸塩、硝酸塩、リン酸塩、ホ
ウ酸塩などの無機塩類;酢酸塩、シユウ酸塩、ギ
酸塩などの有機酸塩類;シアン化物類;水酸化物
類;酸化物類;硫化物類;ニトロ基、シアノ基、
ハロゲン、シユウ酸イオンなどのアニオンを含む
金属酸塩及びアンモニア、アミン類、ホスフイン
類、一酸化炭素、キレート配位子などを含む塩又
は錯体などの金属の錯化合物類;有機配位子又は
有機基を有する有機金属化合物類などがあげられ
る。
これらの触媒成分の中では、パラジウム又はロ
ジウム若しくはその両方を含むものが特に好まし
く、このようなものとしては、例えばPd黒;Pd
−C、Pd−Al2O3、Pd−SiO2、Pd−TiO2、Pd−
ZrO2、Pd−BaSO4、Pd−CaCO3、Pd−アスベ
スト、Pd−ゼオライト、Pd−モレキユラーシー
ブなどの担持パラジウム触媒類;Pd−Pb、Pd−
Se、Pd−Te、Pd−Hg、Pd−Ti、Pd−P、Pd
−Cu、Pd−Ag、Pd−Fe、Pd−Co、Pd−Ni、
Pd−Rhなどの合金又は金属間化合物類;及びこ
れらの合金又は金属間化合物を前記のような担体
に担持したもの;PdCl2、PdBr2、PdI2、Pd
(NO3)2、PdSO4などの無機塩類;Pd
(OCOCH3)2、シユウ酸パラジウムなどの有機酸
塩類;Pd(ON)2;PdO;PdS;M2〔PdX4〕、M2
〔PdX6〕で表わされる。パラジウム酸塩類(Mは
アルカリ金属、アンモニウムイオンを表わし、X
はニトロ基、シアノ基、ハロゲンを表わす。);
〔Pd(NH3)4〕X2、〔Pd(en)2〕X2などのパラジウ
ムのアンミン錯体類(Xは上記と同じ意味をも
ち、enはエチレンジアミンを表わす);PdCl2
(PhCN)2、PdCl2(PR3)2、Pd(CO)(PR3)3、Pd
(PPh3)4、PdCl(R)(PPh3)2、Pd(C2H4)
(PPh3)2、Pd(C3H5)2などの錯化合物又は有機金
属化合物類(Rは有機基を表わす);Pd(acac)2
などのキレート配位子が配位した錯化合物類;
Rh黒;Pdと同様な担持ロジウム触媒類;Pdと同
様なRh合金又は金属間化合物類及びこれらを担
体に担持したもの;RhCl3及び水和物、RhBr2及
び水和物、RhI3及び水和物、Rh2(SO4)3及び水和
物などの無機塩類;Rh2(OCOCH3)4;Rh2O3、
RhO2;M3〔RhX6〕及び水和物(M、Xは前記と
同じ意味をもつ);〔Rh(NH3)5)X3、〔Rh(en)3〕
X3などのロジウムのアンミン錯体類;Rh4
(CO)12、Rh6(CO)16などのロジウムカルボニル
クラスター類;〔RhCl(CO)2〕2、PhCl3(PR3)3、
RhCl(PPh3)3、RhX(CO)L2(Xは前記と同じ意
味をもち、Lは有機リン化合物及び有機ヒ素化合
物からなる配位子である)、RhH(CO)(PPh3)3
などの錯化合物又は有機金属化合物類があげられ
る。
本発明においては、これらの白金族金属又は白
金族元素を含む化合物を1種だけ用いてもよい
し、また2種以上混合して用いてもよく、その使
用量については特に制限はないが、通常白金族元
素を含む成分が尿素化合物に対して、0.0001〜50
モル%の範囲であるのが望ましい。
また本発明で用いられるハロゲンを含む化合物
とは、白金族元素を含まない化合物であれば有機
性、無機性いずれのものであつてもよく、例えば
金属ハロゲン化物、ハロゲン化オニウム化合物、
反応系でハロゲン化オニウム化合物を生成するこ
とのできる化合物、ハロゲンのオキソ酸またはそ
の塩、ハロゲンを含む錯化合物、有機ハロゲン化
物などが好ましく用いられる。
金属のハロゲン化物としては、例えば、アルカ
リ金属、アルカリ土類金属、銅、銀、亜鉛、カド
ミウム、水銀、アルミニウム、カリウム、タリウ
ム、ゲルマニウム、スズ、鉛、アンチモン、ビス
マス、チタン、ジルコニウム、バナジウム、ニオ
ブ、タンタル、テルル、クロム、モリブデン、タ
ングステン、マンガン、レニウム、鉄、コバル
ト、ニツケル、希土類金属などのハロゲン化物が
用いられる。特に好ましいのはアルカリ金属およ
びアルカリ土類金属のハロゲン化物である。
アルカリ金属およびアルカリ土類金属のハロゲ
ン化物としては、例えばフツ化ナトリウム、フツ
化セシウム、フツ化バリウム、塩化リチウム、塩
化ナトリウム、塩化カリウム、塩化ルビジウム、
塩化セシウム、塩化マグネシウム、塩化カルシウ
ム、塩化ストロンチウム、塩化バリウム、臭化リ
チウム、臭化ナトリウム、臭化ルビジウム、臭化
セシウム、臭化マグネシウム、臭化ストロンチウ
ム、臭化バリウム、ヨウ化リチウム、ヨウ化ナト
リウム、ヨウ化カリウム、ヨウ化ルビジウム、ヨ
ウ化セシウム、ヨウ化マグネシウム、ヨウ化カル
シウム、ヨウ化ストロンチウム、ヨウ化バリウ
ム、などの単一金属と単一ハロゲンとの化合物
類;塩化マグネシウムナトリウム、塩化マグネシ
ウムカリウム、塩化カルシウムカリウム、臭化マ
グネシウムカリウムなどの複塩類;フツ化臭素カ
リウム、塩化ヨウ素カリウム、塩化ヨウ素ルビジ
ウム、塩化ヨウ素セシウム、臭化塩化ヨウ素セシ
ウム、臭化塩化ヨウ素ルビジウム、臭化ヨウ素カ
リウム、臭化ヨウ素セシウム、臭化ヨウ素ルビジ
ウムなどのポリハロゲン化物類などがあげられ
る。
ハロゲン化オニウム化合物とは孤立電子対をも
つ元素を含む化合物において、これらの孤立電子
対にプロトンあるいは他の陽イオン形の試薬が結
合して孤立電子対をもつ元素が共有結合原子価1
を増加して陽イオンとなつているものであつて、
対イオンとしてハロゲンアニオンを有するもので
ある。
このようなオニウム化合物としては、アンモニ
ウム化合物(〔R1R2R3R4N
〕X
)、ホスホニ
ウム化合物(〔R1R2R3R4P
〕X
)、アルソニ
ウム化合物(〔R1R2R3R4As
〕X
)、スチボニ
ウム化合物(〔R1R2R3R4Sd
〕X
)、オキソニ
ウム化合物(〔R1R2R3O
〕X
)、スルホニウ
ム化合物(〔R1R2R3S
〕X
)、オキシスルホ
ニウム化合物(〔R1R2R3S
(O)〕X
)、セレ
ノニウム化合物(〔R1R2R3Se
〕X
)、テルロ
ニウム化合物(〔R1R2R3Te
〕X
)、スタンノ
ニウム化合物(〔R1R2R3Sn
〕X
)、ヨウドニ
ウム化合物(〔R1R2I
〕X
)などが挙げられ
る。ここでR1、R2、R3、R4は水素または脂肪族
基、芳香族基、脂環族基、芳香脂肪族基、複素環
式基から選ばれた基を表わし、それぞれが同じで
あつてもよいし、また場合によつては孤立電子対
を有する元素を含む環の構成要素であつてもよ
い。またXはF、Cl、Br、Iから選ばれたハロ
ゲンを表わす。もちろん、このようなオニウムグ
ループを分子内に2個以上有する化合物であつて
もよいし、さらには主鎖または側鎖にこのような
オニウムグループを含むポリマーであつてもよ
い。
このような陰イオンがハロゲンであるオニウム
化合物であるハロゲン化オニウム化合物は、ハロ
ゲン化水素または有機ハロゲン化物と相当するア
ミンまたは含窒素化合物、ホスフイン化合物、ア
ルシン化合物、スチビン化合物、オキシ化合物、
スルフイド化合物、スルホキシド化合物、セレニ
ド化合物、テルリド化合物などとの反応によつて
容易に得られるものであり、これらは反応系外で
製造されたものを用いてもよいし、反応系内でこ
れらを生成させてもよい。もちろん他の方法で製
造されたものであつてもよいし、他の方法によつ
て反応系内で生成させたものであつてもよい。
これらの中で好ましいのは、ハロゲン化アンモ
ニウム化合物、ハロゲン化ホスホニウム化合物、
ハロゲン化アルソニウム化合物およびハロゲン化
スルホニウム化合物で、特に好ましいのはハロゲ
ン化アンモニウム化合物およびハロゲン化ホスホ
ニウム化合物である。ハロゲン化アンモニウム化
合物は相当する含窒素化合物とハロゲン化水素と
の反応、含窒素化合物とハロゲン化アルキルある
いはハロゲン化アリールとの反応などによつて容
易に得ることができるが、このような含窒素化合
物としては、例えば、アンモニア;1級アミン、
2級アミン、3級アミン等のアミン類;ヒドロキ
シルアミン類;ヒドラジン類;ヒドラゾン類;ア
ミノ酸類;オキシム類、イミドエステル類;アミ
ド類および種々の含窒素複素環式化合物等があ
る。
好ましい含窒素化合物のハロゲン化水素塩とし
ては、塩化アンモニウム、臭化アンモニウム、ヨ
ウ化アンモニウム等のアンモニアの塩類;ジフエ
ニルアミン、トリフエニルアミン等の芳香族アミ
ンの塩類;メチルアミン、エチルアミン、ヘキシ
ルアミン、オクチルアミン、ジメチルアミン、ト
リメチルアミン、ジエチルアミン、トリエチルア
ミン、ジブチルアミン、トリプロピルアミン、メ
チルエチルアミン、ジメチルエチルアミン、ジブ
チルメチルアミン、トリブチルアミン、エチレン
ジアミン、ヘキサメチレンジアミン等の脂肪族ア
ミンの塩類;シクロプロピルアミン、シクロヘキ
シルアミン、N−メチルシクロヘキシルアミン等
の脂環族アミンの塩類;ベンジルアミン、N−メ
チルベンジルアミン、N,N−ジエチルベンジル
アミン、ジベンジルアミン等の芳香脂肪族アミン
の塩類;ピペリジン、ピペラジン、モルホリン、
ピリジン、キノリン、ヘキサメチレンテトラミ
ン、オキサゾール、チアゾール、イミダゾール、
トリアゾール、ベンゾトリアゾール、ジアザビシ
クロウンデセン等の含窒素複素環式化合物の塩
類;ジメチルアセトアミド、N−メチルプロリド
ン等のアミドの塩類などが用いられる。
また4級アンモニウムハライドとしては、ハロ
ゲン化テトラメチルアンモニウム、ハロゲン化テ
トラエチルアンモニウム、ハロゲン化テトラブチ
ルアンモニウム、ハロゲン化トリメチルエチルア
ンモニウム、ハロゲン化ジエチルジブチルアンモ
ニウム等の脂肪族4級アンモニウムハライド類;
ハロゲン化N,N,N−トリメチルシクロヘキシ
ルアンモニウム等の脂環族4級アンモニウムハラ
イド類;ハロゲン化テトラベンジルアンモニウ
ム、ハロゲン化トリメチルベンジルアンモニウム
等の芳香脂肪族4級アンモニウムハライド類;ハ
ロゲン化N,N,N−トリメチルフエニルアンモ
ニウム、ハロゲン化N,N,N−トリエチルフエ
ニルアンモニウム等の芳香族4級アンモニウムハ
ライド類;ハロゲン化N−メチルピリジニウム、
ハロゲン化N−エチルキノリニウム、ハロゲン化
N,N−ジメチルピペリジニウム、ハロゲン化
N,N′−ジメチルイミダゾリニウム等の複素環
式4級アンモニウムハライド等が好ましく用いら
れる。
また、ハロゲン化アンモニウムグループを主鎖
または側鎖に含むポリマーとしては、例えば、次
のような主要構成単位を有するものが好ましく用
いられる。
The present invention relates to a method for producing a urethane compound, and more particularly to a method for producing a urethane compound by reacting a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of an oxidizing agent to oxidatively carbonylate it. It is. Urethanes are important compounds used in carbamate pesticides and the like, and recently there has been a demand for inexpensive methods of producing them as raw materials for producing isocyanates without using phosgene. As a method for producing such urethane compounds using carbon monoxide, aromatic nitro compounds,
A method of reductively urethanizing an aromatic nitroso compound, an aromatic azo compound, an aromatic azoxy compound, etc. in the absence of an oxidizing agent, and a method of oxidatively urethanizing an aromatic amino compound are known. Furthermore, a method of oxidatively converting N,N'-diarylurea into urethane has also been proposed (Japanese Unexamined Patent Application Publication No. 1983-1999-
Publication No. 120552). In this method, a group noble metal or its compound is used as the main catalyst, and a Lewis acid such as copper chloride, iron chloride, iron oxychloride, vanadium chloride, vanadium oxychloride, etc. is used as a cocatalyst, and a redox reaction is carried out in the reaction system. It is necessary to dissolve chlorides containing metals in the reaction system. However, these dissolved metal chlorides are highly corrosive to metal materials such as reaction vessels, piping, valves, etc., and therefore there is an equipment problem in that expensive metal materials must be used. Furthermore, in order to separate and recover these dissolved metal chlorides from high boiling point substances such as aromatic urethane products, there is a drawback that complicated operations and large costs are required. In addition, in the methods using these catalyst systems, the selectivity of urethane compounds based on carbon monoxide is not satisfactory for industrial implementation, and in particular, N,
Another problem was that as the reaction rate of N'-diarylurea increased, the selectivity of the urethane compound based on carbon monoxide further decreased. Therefore, the present inventors conducted intensive research to find a catalyst system that does not have these problems in the prior art and can produce urethane with high yield and high selectivity in the method of oxidatively converting urea compounds into urethanes. As a result, an effective catalyst system was discovered and proposed earlier.
These catalyst systems consist of at least one type selected from platinum group metals and compounds containing platinum group elements, and at least one type of halogen compound,
It has also been found that, as a halogen compound, a compound containing bromine or iodine is a particularly effective promoter. By using these catalyst systems, the yield and selectivity of urethane compounds based on urea compounds and carbon monoxide could be greatly improved compared to the prior art; however, the reaction rate of urea compounds It was found that when the selectivity of urethane compounds based on carbon monoxide was increased to over 90%, for example, the selectivity of urethane compounds based on carbon monoxide decreased slightly.As a result of further intensive research to improve this point, these catalysts The selectivity of urethane compounds based on carbon monoxide can be improved by combining the use of a reaction system with a method of conducting the reaction while removing all or part of the water produced by the reaction from the reaction system. It has been found that not only the reaction rate but also the yield and selectivity based on urea compounds can be further improved, and based on these findings, the present invention has been completed. That is, the present invention provides an oxidizing agent, and (a) at least one selected from platinum group metals and compounds containing platinum group elements, and (b) at least one selected from halogen compounds. In a method for producing urethane by reacting a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system consisting of An object of the present invention is to provide a method for producing urethane, which is characterized in that the reaction is carried out at the same time. Furthermore, in addition to the catalyst system and reaction scheme described above, the present invention provides a basic substance and/or as an additional cocatalyst.
Another object of the present invention is to provide a method for producing a urethane compound using at least one selected from chelating reagents. As a method for removing all or part of the water produced by the reaction out of the reaction system, which is one of the features of the present invention, any method may be used as long as water can be substantially removed. Distillation method,
Particularly preferred are a removal method using a reaction gas containing carbon monoxide or a carrier agent such as a low-boiling point organic substance, a method of distilling off together with a part of the organic hydroxyl compound, and a method of combining these. Therefore, the reaction method may be either a batch method or a flow method for the liquid phase, but it is preferable to use a flow method for the gas component containing carbon monoxide. The platinum group metal and platinum group element-containing compound used in the method of the present invention may contain at least one component selected from platinum group elements such as palladium, rhodium, platinum, ruthenium, iridium, and osmium. There are no particular limitations on these elements, and these elements may be in a metallic state or may be components forming a compound. In addition, these catalyst components include activated carbon, graphite,
Silica, alumina, silica - alumina, silica -
It may be supported on a carrier such as titania, titania, zirconia, barium sulfate, calcium carbonate, asbestos, bentonite, diatomaceous earth, polymer, ion exchange resin, zeolite, molecular sieve, magnesium silicate, magnesia, etc. . Examples of platinum group elements in the metallic state include metals such as palladium, rhodium, platinum, ruthenium, iridium, and osmium, these metal blacks, and catalyst components containing these metal ions on the above-mentioned carrier, and then hydrogen and Those reduced with formaldehyde, alloys or intermetallic compounds containing these metals, etc. are used. Further, the alloy or intermetallic compound may be one of these platinum group metals, or may be one of these platinum group metals, or may contain other elements such as selenium, tellurium, sulfur, antimony, bismuth,
Copper, silver, gold, zinc, tin, vanadium, iron, cobalt, nickel, mercury, lead, thallium, chromium,
It may also contain molybdenum, tungsten, or the like. On the other hand, compounds containing platinum group elements include, for example, inorganic salts such as halides, sulfates, nitrates, phosphates, and borates; organic acid salts such as acetates, oxalates, and formates; and cyanides. ; Hydroxides; Oxides; Sulfides; Nitro group, cyano group,
Complex compounds of metals such as metal salts containing anions such as halogens and oxalate ions, and salts or complexes containing ammonia, amines, phosphines, carbon monoxide, chelate ligands, etc.; organic ligands or organic Examples include organometallic compounds having groups. Among these catalyst components, those containing palladium or rhodium or both are particularly preferred, such as Pd black; Pd black;
-C, Pd- Al2O3 , Pd- SiO2 , Pd - TiO2 , Pd-
Supported palladium catalysts such as ZrO 2 , Pd-BaSO 4 , Pd-CaCO 3 , Pd-asbestos, Pd-zeolite, Pd-molecular sieve; Pd-Pb, Pd-
Se, Pd-Te, Pd-Hg, Pd-Ti, Pd-P, Pd
−Cu, Pd−Ag, Pd−Fe, Pd−Co, Pd−Ni,
Alloys or intermetallic compounds such as Pd-Rh; and these alloys or intermetallic compounds supported on the above-mentioned supports; PdCl 2 , PdBr 2 , PdI 2 , Pd
(NO 3 ) 2 , PdSO 4 and other inorganic salts; Pd
(OCOCH 3 ) 2 , organic acid salts such as palladium oxalate; Pd(ON) 2 ; PdO; PdS; M 2 [PdX 4 ], M 2
It is expressed as [PdX 6 ]. Palladate salts (M represents an alkali metal, ammonium ion,
represents a nitro group, a cyano group, or a halogen. );
Palladium ammine complexes such as [Pd(NH 3 ) 4 ]X 2 , [Pd(en) 2 ]X 2 (X has the same meaning as above, and en represents ethylenediamine); PdCl 2
(PhCN) 2 , PdCl 2 (PR 3 ) 2 , Pd(CO) (PR 3 ) 3 , Pd
(PPh 3 ) 4 , PdCl(R) (PPh 3 ) 2 , Pd(C 2 H 4 )
Complex compounds or organometallic compounds such as (PPh 3 ) 2 , Pd(C 3 H 5 ) 2 (R represents an organic group); Pd(acac) 2
Complex compounds coordinated with chelate ligands such as;
Rh black; Supported rhodium catalysts similar to Pd; Rh alloys or intermetallic compounds similar to Pd, and those supported on supports; RhCl 3 and hydrates, RhBr 2 and hydrates, RhI 3 and water Inorganic salts such as hydrates, Rh 2 (SO 4 ) 3 and hydrates; Rh 2 (OCOCH 3 ) 4 ; Rh 2 O 3 ,
RhO 2 ; M 3 [RhX 6 ] and hydrates (M and X have the same meanings as above); [Rh(NH 3 ) 5 )X 3 , [Rh(en) 3 ]
Rhodium ammine complexes such as X 3 ; Rh 4
Rhodium carbonyl clusters such as (CO) 12 , Rh 6 (CO) 16 ; [RhCl(CO) 2 ] 2 , PhCl 3 (PR 3 ) 3 ,
RhCl (PPh 3 ) 3 , RhX (CO) L 2 (X has the same meaning as above, L is a ligand consisting of an organic phosphorus compound and an organic arsenic compound), RhH (CO) (PPh 3 ) 3
Examples include complex compounds such as or organometallic compounds. In the present invention, only one type of these platinum group metals or compounds containing platinum group elements may be used, or two or more types may be used as a mixture, and there is no particular restriction on the amount used. Normally, components containing platinum group elements are 0.0001 to 50% relative to urea compounds.
A range of mole % is desirable. Further, the halogen-containing compound used in the present invention may be either organic or inorganic as long as it does not contain a platinum group element, such as metal halides, onium halide compounds,
Compounds that can produce onium halide compounds in the reaction system, oxoacids of halogens or salts thereof, complex compounds containing halogens, organic halides, and the like are preferably used. Examples of metal halides include alkali metals, alkaline earth metals, copper, silver, zinc, cadmium, mercury, aluminum, potassium, thallium, germanium, tin, lead, antimony, bismuth, titanium, zirconium, vanadium, and niobium. , tantalum, tellurium, chromium, molybdenum, tungsten, manganese, rhenium, iron, cobalt, nickel, rare earth metals, and other halides are used. Particularly preferred are alkali metal and alkaline earth metal halides. Examples of alkali metal and alkaline earth metal halides include sodium fluoride, cesium fluoride, barium fluoride, lithium chloride, sodium chloride, potassium chloride, rubidium chloride,
Cesium chloride, magnesium chloride, calcium chloride, strontium chloride, barium chloride, lithium bromide, sodium bromide, rubidium bromide, cesium bromide, magnesium bromide, strontium bromide, barium bromide, lithium iodide, sodium iodide , potassium iodide, rubidium iodide, cesium iodide, magnesium iodide, calcium iodide, strontium iodide, barium iodide, and other compounds of a single metal and a single halogen; sodium magnesium chloride, potassium magnesium chloride , calcium potassium chloride, magnesium potassium bromide and other double salts; potassium bromine fluoride, potassium iodine chloride, rubidium iodine chloride, cesium iodine chloride, cesium iodine chloride bromide, rubidium iodine bromide, potassium iodine bromide, bromide Examples include polyhalides such as cesium iodine and rubidium iodine bromide. An onium halide compound is a compound containing an element with a lone pair of electrons, in which a proton or other cationic reagent is bonded to these lone pairs, and the element with a lone pair of electrons forms a covalent bond with a valence of 1.
increases and becomes a cation,
It has a halogen anion as a counter ion. Examples of such onium compounds include ammonium compounds ([R 1 R 2 R 3 R 4 N ]X), phosphonium compounds ([R 1 R 2 R 3 R 4 P ] R 3 R 4 As ]X), stibonium compounds ([ R 1 R 2 R 3 R 4 Sd ] 3 S ]X ) , oxysulfonium compounds ([R 1 R 2 R 3 S ( O ) ] Examples include Te ]X ), stannonium compounds ([R 1 R 2 R 3 Sn ]X ), and iodonium compounds ([R 1 R 2 I ]X ). Here, R 1 , R 2 , R 3 , and R 4 represent hydrogen or a group selected from an aliphatic group, an aromatic group, an alicyclic group, an araliphatic group, and a heterocyclic group, and each is the same. Alternatively, in some cases, it may be a constituent element of a ring containing an element having a lone pair of electrons. Further, X represents a halogen selected from F, Cl, Br, and I. Of course, it may be a compound having two or more such onium groups in its molecule, or it may be a polymer containing such onium groups in its main chain or side chain. Such halogenated onium compounds, which are onium compounds whose anion is a halogen, include amines or nitrogen-containing compounds, phosphine compounds, arsine compounds, stibine compounds, oxy compounds,
It is easily obtained by reaction with sulfide compounds, sulfoxide compounds, selenide compounds, telluride compounds, etc. These can be produced outside the reaction system, or they can be produced within the reaction system. You may let them. Of course, it may be produced by other methods, or may be produced within the reaction system by other methods. Among these, preferred are halogenated ammonium compounds, halogenated phosphonium compounds,
Among the halogenated arsonium compounds and halogenated sulfonium compounds, particularly preferred are halogenated ammonium compounds and halogenated phosphonium compounds. Halogenated ammonium compounds can be easily obtained by reacting a corresponding nitrogen-containing compound with hydrogen halide, or by reacting a nitrogen-containing compound with an alkyl halide or an aryl halide. For example, ammonia; primary amine;
Examples include amines such as secondary amines and tertiary amines; hydroxylamines; hydrazines; hydrazones; amino acids; oximes, imidoesters, amides, and various nitrogen-containing heterocyclic compounds. Preferred hydrogen halide salts of nitrogen-containing compounds include salts of ammonia such as ammonium chloride, ammonium bromide, and ammonium iodide; salts of aromatic amines such as diphenylamine and triphenylamine; methylamine, ethylamine, hexylamine, and octylamine. Salts of aliphatic amines such as amine, dimethylamine, trimethylamine, diethylamine, triethylamine, dibutylamine, tripropylamine, methylethylamine, dimethylethylamine, dibutylmethylamine, tributylamine, ethylenediamine, hexamethylenediamine; cyclopropylamine, cyclohexylamine , salts of alicyclic amines such as N-methylcyclohexylamine; salts of aromatic aliphatic amines such as benzylamine, N-methylbenzylamine, N,N-diethylbenzylamine, dibenzylamine; piperidine, piperazine, morpholine,
Pyridine, quinoline, hexamethylenetetramine, oxazole, thiazole, imidazole,
Salts of nitrogen-containing heterocyclic compounds such as triazole, benzotriazole and diazabicycloundecene; salts of amides such as dimethylacetamide and N-methylprolidone are used. Examples of quaternary ammonium halides include aliphatic quaternary ammonium halides such as halogenated tetramethylammonium, halogenated tetraethylammonium, halogenated tetrabutylammonium, halogenated trimethylethylammonium, and halogenated diethyldibutylammonium;
Alicyclic quaternary ammonium halides such as halogenated N,N,N-trimethylcyclohexyl ammonium; Aroaliphatic quaternary ammonium halides such as halogenated tetrabenzylammonium and halogenated trimethylbenzylammonium; halogenated N,N, Aromatic quaternary ammonium halides such as N-trimethylphenylammonium and halogenated N,N,N-triethylphenylammonium; halogenated N-methylpyridinium,
Heterocyclic quaternary ammonium halides such as halogenated N-ethylquinolinium, halogenated N,N-dimethylpiperidinium, and halogenated N,N'-dimethylimidazolinium are preferably used. Further, as the polymer containing a halogenated ammonium group in the main chain or side chain, for example, those having the following main structural units are preferably used.
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】
ここでR1、R2、R3、Xは前記のとおりであり、
R5は2価の有機基を表わす。
ハロゲン化ホスホニウム化合物としては、例え
ば、ハロゲン化テトラメチルホスホニウム、ハロ
ゲン化テトラエチルホスホニウム、ハロゲン化テ
トラブチルホスホニウム等の対称形テトラアルキ
ルホスホニウム化合物類;ハロゲン化エチルトリ
メチルホスホニウム、ハロゲン化ジエチルジメチ
ルホスホニウム等の非対称形テトラアルキルホス
ホニウム化合物類;ハロゲン化テトラフエニルホ
スホニウム、ハロゲン化テトラ(p−トリル)ホ
スホニウム等の対称形テトラアリールホスホニウ
ム化合物類;ハロゲン化(α−ナフチル)トリフ
エニルホスホニウム等の非対称形テトラアリール
ホスホニウム化合物類;ハロゲン化メチルトリフ
エニルホスホニウム、ハロゲン化フエニルトリメ
チルホスホニウム等のアルキルアリール混合ホス
ホニウム化合物類;ハロゲン化テトラベンジルホ
スホニウム等のテトラアラルキルホスホニウム化
合物類などが好ましく用いられる。
ハロゲン化アルソニウム化合物としては、例え
ば、ハロゲン化テトラメチルアルソニウム、ハロ
ゲン化テトラエチルアルソニウム等の対称形テト
ラアルキルアルソニウム化合物類;ハロゲン化メ
チルトリエチルアルソニウム、ハロゲン化ジメチ
ルジエチルアルソニウム等の非対称形テトラアル
キルアルソニウム化合物類;ハロゲン化テトラフ
エニルアルソニウム等の対称形テトラアリールア
ルソニウム化合物類;ハロゲン化メチルトリフエ
ニルアルソニウム、ハロゲン化エチルトリフエニ
ルアルソニウム、ハロゲン化フエニルトリメチル
アルソニウム等のアルキルアリール混合アルソニ
ウム化合物類などが好ましく用いられる。
また、ハロゲン化スルホニウム化合物として
は、例えば、ハロゲン化トリメチルスルホニウ
ム、ハロゲン化トリエチルスルホニウム、ハロゲ
ン化メチルジエチルスルホニウム等の対称または
非対称形アルキルスルホニウム化合物類;ハロゲ
ン化トリフエニルスルホニウム等のアリールスル
ホニウム化合物類;ハロゲン化ジメチルフエニル
スルホニウム、ハロゲン化メチルジフエニルスル
ホニウム等のアルキルアリールスルホニウム化合
物類;ハロゲン化ビシクロー(2,2,1)−ヘ
プタン−1−スルホニウム、ハロゲン化チオピリ
リウム等の環状スルホニウム化合物類などが好ま
しく用いられる。
また、ハロゲン化ホスホニウムグループあるい
はハロゲン化スルホニウムグループを主鎖または
側鎖に含むポリマー類も好ましく用いられるが、
そのようなポリマーとしては、例えば、次のよう
な主要構成単位を有するものが挙げられる。[Formula] Here, R 1 , R 2 , R 3 , and X are as described above,
R 5 represents a divalent organic group. Examples of halogenated phosphonium compounds include symmetric tetraalkylphosphonium compounds such as halogenated tetramethylphosphonium, halogenated tetraethylphosphonium, and halogenated tetrabutylphosphonium; asymmetric types such as halogenated ethyltrimethylphosphonium and halogenated diethyldimethylphosphonium Tetraalkylphosphonium compounds; Symmetrical tetraarylphosphonium compounds such as halogenated tetraphenylphosphonium and halogenated tetra(p-tolyl)phosphonium; Asymmetrical tetraarylphosphonium compounds such as halogenated (α-naphthyl)triphenylphosphonium alkylaryl mixed phosphonium compounds such as halogenated methyltriphenylphosphonium and halogenated phenyltrimethylphosphonium; tetraaralkylphosphonium compounds such as halogenated tetrabenzylphosphonium, and the like are preferably used. Examples of the halogenated arsonium compounds include symmetrical tetraalkylarsonium compounds such as tetramethylarsonium halide and tetraethylarsonium halide; asymmetrical tetraalkylarsonium compounds such as methyltriethylarsonium halide and dimethyldiethylarsonium halide; Alkyl arsonium compounds; symmetrical tetraaryl arsonium compounds such as halogenated tetraphenyl arsonium; alkyl halogenated methyl triphenyl arsonium, halogenated ethyl triphenyl arsonium, halogenated phenyl trimethyl arsonium, etc. Aryl mixed arsonium compounds and the like are preferably used. Examples of halogenated sulfonium compounds include symmetrical or asymmetrical alkylsulfonium compounds such as trimethylsulfonium halide, triethylsulfonium halide, and methyldiethylsulfonium halide; arylsulfonium compounds such as triphenylsulfonium halide; Alkylarylsulfonium compounds such as dimethylphenylsulfonium chloride and methyldiphenylsulfonium halide; cyclic sulfonium compounds such as bicyclo(2,2,1)-heptane-1-sulfonium halide and thiopyrylium halide are preferably used. It will be done. Polymers containing a halogenated phosphonium group or a halogenated sulfonium group in the main chain or side chain are also preferably used, but
Examples of such polymers include those having the following main structural units.
【式】【formula】
【式】
(式中、R1、R2、R3、Xは前記のとおりであ
る。)
ハロゲンのオキソ酸およびその塩とは、酸化数
が正1、3、5、7のハロゲンの酸素酸およびそ
の塩のことであつて、具体的には次亜塩素酸、亜
塩素酸、塩素酸、過塩素酸、次亜臭素酸、臭素
酸、過臭素酸、次亜ヨウ素酸、亜ヨウ素酸、ヨウ
素酸、オルト過ヨウ素酸、メタ過ヨウ素酸および
これらの酸の塩のことである。
塩類の陽イオンとしては、アンモニウムイオン
および種々の金属イオンなどどのようなものであ
つてもよいが、アルカリ金属イオンおよびアルカ
リ土類金属イオンが好ましい。
このような塩としては例えば次亜塩素酸ナトリ
ウム、次亜塩素酸カリウム、次亜塩素酸カルシウ
ム、次亜塩素酸バリウムなどの次亜塩素酸塩類;
亜塩素酸ナトリウムなどの亜塩素酸塩類;塩素酸
リチウム、塩素酸ナトリウム、塩素酸カリウム、
塩素酸ルビジウム、塩素酸セシウム、塩素酸マグ
ネシウム、塩素酸カルシウム、塩素酸バリウムな
どの塩素酸塩類、過塩素酸アルミニウム、過塩素
酸カルシウム、過塩素酸バリウム、過塩素酸亜
鉛、過塩素酸カドミウム、過塩素酸水銀、過塩素
酸セリウム、過塩素酸鉛、過塩素酸アンモニウム
などの過塩素酸塩類;次亜臭素酸ナトリウム、次
亜臭素酸カリウムなどの次亜臭素酸塩類、亜臭素
酸ナトリウムなどの亜臭素酸塩類;臭素酸リチウ
ム、臭素酸ナトリウム、臭素酸カリウム、臭素酸
ルビジウム、臭素酸セシウム、臭素酸マグネシウ
ム、臭素酸カルシウム、臭素酸ストロンチウム、
臭素酸バリウム、臭素酸銀、臭素酸亜鉛、臭素酸
カドミウム、臭素酸水銀、臭素酸アルミニウム、
臭素酸ランタン、臭素酸サマリウム、臭素酸鉛、
臭素酸アンモニウムなどの臭素酸塩類;過臭素酸
カリウムなどの過臭素酸塩類;次亜ヨウ素酸ナト
リウム、次亜ヨウ素酸カリウム、次亜ヨウ素酸ル
ビジウム、次亜ヨウ素酸セシウム、次亜ヨウ素酸
カルシウム、次亜ヨウ素酸バリウム等の次亜ヨウ
素酸塩類;ヨウ素酸リチウム、ヨウ素酸ナトリウ
ム、ヨウ素酸カリウム、ヨウ素酸水素カリウム、
ヨウ素酸ルビジウム、ヨウ素酸セシウム、ヨウ素
酸マグネシウム、ヨウ素酸カルシウム、ヨウ素酸
ストロンチウム、ヨウ素酸バリウム、ヨウ素酸
銀、ヨウ素酸金、ヨウ素酸亜鉛、ヨウ素酸カドミ
ウム、ヨウ素酸水銀、ヨウ素酸アルミニウム、ヨ
ウ素酸インジウム、ヨウ素酸ランタン、ヨウ素酸
セリウム、ヨウ素酸プロセオジム、ヨウ素酸ネオ
ジム、ヨウ素酸ガドリニウム、ヨウ素酸鉛、ヨウ
素酸アンモニウムなどのヨウ素酸塩類;過ヨウ素
酸リチウム、メタ過ヨウ素酸ナトリウム、オルト
過ヨウ素酸二水素三ナトリウム、オルト過ヨウ素
酸三水素二ナトリウム、メタ過ヨウ素酸カリウ
ム、オルト過ヨウ素酸三水素二カリウム、二メソ
過ヨウ素酸水素三カリウム、過ヨウ素酸ルビジウ
ム、過ヨウ素酸セシウム、過ヨウ素酸バリウム、
メタ過ヨウ素酸銀、メソ過ヨウ素酸銀、オルト過
ヨウ素酸銀、オルト過ヨウ素酸三水素銀、過ヨウ
素酸亜鉛、過ヨウ素酸カドミウム、過ヨウ素酸
鉛、過ヨウ素酸アンモニウムなどの過ヨウ素酸塩
類などが用いられる。
ハロゲンを含む錯化合物とは陽イオン性、陰イ
オン性いずれのハロゲンを含むものであつてもよ
く、例えばジクロロ臭素酸アンモニウム、テトラ
ブロモヨウ素酸テトラメチルアンモニウム等のポ
リハロゲン化ハロゲン酸塩類;ヘキサヨードテル
酸カリウム、テトラヨード水銀酸テトラエチルア
ンモニウム、テトラヨードビスマス酸カリウム、
テトラブロモ銅酸ナトリウム、テトラブロモ鉄酸
セシウム、ヘキサヨードスズ酸バリウム、テトラ
ヨード鉛酸カリウム、ヘキサブロモテルル酸カリ
ウム等のハロゲン化金属酸塩類;テトラブロモ
(ジエチルスクシナート)スズ、オクタテス(N,
N−ジメチルホルムアミド)ランタントリヨウダ
イド、ヘキサキス(ウレア)クロムトリブロミ
ド、ヘキサアンミンクロムトリブロミド、ヨウド
ペンタアンミンクロムトリヨウダイド、トリス
(ピリジン)クロムトリブロミド、トリス(ピリ
ジン)モリブデントリヨウダイド、ヘキサアンミ
ンコバルトトリブロミド、ビス(2,2′−ビピリ
ジン)銅ジヨウダイドなどの配位子を有する錯体
類などが用いられる。
また、有機ハロゲン化物とは、一般式
R6(X)n
(式中、R6はm価の有機基、Xはハロゲン、m
は1以上の整数を意味する。)
で表わされるものであつて、mは2以上の場合、
Xは2種以上の異なるハロゲン種であつてもよ
い。また、ハロゲンXは炭素以外のヘテロ原子、
例えば、窒素、リン、酸素、イオウ、セレンなど
と結合しているものであつてもよい。
このような有機ハロゲン化物としては、例え
ば、ハロゲン化メチル、ハロゲン化エチル、ハロ
ゲン化プロピル(各異性体)、ハロゲン化ブチル
(各異性体)、ハロゲン化アミル(各異性体)、ハ
ロゲン化ヘキシル(各異性体)、ハロゲン化オク
チル(各異性体)、ハロゲン化パーフルオロヘキ
シル(各異性体)、ハロゲン化パーフルオロヘプ
チル(各異性体)、ハロゲン化ビニル、ハロゲン
化アリル、ハロゲン化メチレン、ハロホルム、テ
トラハロゲンメタン、ハロゲン化アルキリデン、
ジハロゲン化エタン(各異性体)、トリハロゲン
化エタン(各異性体)、テトラハロゲン化エタン、
ジハロゲン化ブタン(各異性体)、ジハロゲン化
ヘキサン(各異性体)、ジハロエチレン(各異性
体)等の脂肪族モノおよびポリハロゲン化物類;
ハロゲンベンゼン、ジハロゲンベンゼン(各異性
体)、トリハロゲンベンゼン(各異性体)、テトラ
ハロゲンベンゼン(各異性体)、ヘキサハロゲン
ベンゼン、ハロゲンナフタリン、ジハロゲンナフ
タリン(各異性体)、ハロゲンピリジン(各異性
体)、ハロゲントルエン(各異性体)、ハロゲンエ
チルベンゼン(各異性体)、フエニルヨードジク
ロリド、ヨードソベンゼン、ヨードキシベンゼン
等の芳香族モノおよびポリハロゲン化物類;ハロ
ゲン化シクロヘキサン、ハロゲン化シクロブタン
等の脂環族ハロゲン化物類;ハロゲン化ベンジ
ル、ハロゲン化フエネチル等の芳香脂肪族ハロゲ
ン化物類;ハロゲン化フラン、ハロゲン化テトラ
ヒドロフラン、ハロゲン化チオフエン、ハロゲン
化イミダゾール、ハロゲン化ピペリジン等の複素
環式ハロゲン化物類;ハロゲン化アセチル、ハロ
ゲン化ベンゾイル等の酸ハロゲン化物類;N−ハ
ロゲンコハク酸イミド、N−ハロゲンアルキルア
ミン、N−ハロゲンアセトアミド、N−ハロゲン
ベンズアミド等のN−ハロゲン化物類などが好ま
しく用いられる。
さらには、これらの有機基は種々の置換基、例
えば、ニトロ基、低級アルキル基、シアノ基、ア
ルコキシ基、アリーロキシ基、芳香族基、スルホ
キシド基、スルホン基、カルボニル基、エステル
基、アミド基などを含んでいてもよいし、不飽和
基を有するものでもよい。
またハロゲンを含む化合物として塩化水素、臭
化水素、ヨウ化水素などのハロゲン化水素および
ハロゲン化水素酸、又は塩素、臭素、ヨウ素など
のハロゲン分子そのものも用いることができる。
このようなハロゲンを含む化合物は1種だけで
もよいし、2種以上混合して用いることもでき
る。
また反応原料である尿素化合物もしくは有機ヒ
ドロキシル化合物、又は触媒の他の成分がハロゲ
ンを含有する場合には、ハロゲン化合物の添加を
省略することもできる。
本発明方法で用いられるハロゲンを含む化合物
の中で、ハロゲン種が臭素またはヨウ素であるも
のが好ましく、特に好ましいのはヨウ素を含むも
のである。
本発明において用いられるハロゲン化合物の量
については、特に制限はないが、使用される白金
族元素を含む成分の中の金属元素の量に対して、
通常0.001〜10000倍モルの範囲で使用されるのが
好ましい。
さらに本発明において追加的助触媒として用い
ることのできる塩基性物質は無機性、有機性いず
れのものであつてもよい。このような塩基性物質
としては例えば、リチウム、ナトリウム、カリウ
ム等のアルカリ金属類;マグネシウム、カルシウ
ム、バリウム等のアルカリ土類金属類;酸化リチ
ウム、過酸化リチウム、酸化ナトリウム、過酸化
ナトリウム、超酸化ナトリウム、酸化カリウム、
過酸化カリウム、三酸化二カリウム、超酸化カリ
ウム、酸化ルビジウム、過酸化ルビジウム、三酸
化二ルビジウム、超酸化ルビジウム、オゾン化ル
ビジウム、酸化セシウム、過酸化セシウム等のア
ルカリ金属の酸化物類;酸化ベリリウム、酸化マ
グネシウム、酸化カルシウム、過酸化カルシウ
ム、酸化ストロンチウム、過酸化ストロンチウ
ム、酸化バリウム、過酸化バリウムなどのアルカ
リ土類金属の酸化物類;水酸化リチウム、水酸化
ナトリウム、水酸化カリウム、水酸化ルビジウ
ム、水酸化セシウム、水酸化ベリリウム、水酸化
マグネシウム、水酸化カルシウム、水酸化ストロ
ンチウム、水酸化バリウムなどのアルカリ金属お
よびアルカリ土類金属の水酸化物類;炭酸ナトリ
ウム、炭酸水素ナトリウム、炭酸カリウム、炭酸
水素カリウム、炭酸バリウム、ケイ酸ナトリウ
ム、ケイ酸マグネシウム、アルミン酸カリウム、
アルミン酸カルシウム、ホウ酸ナトリウム、ホウ
酸バリウム等の強塩基と弱酸の塩類;炭化カルシ
ウム、炭化セシウム等の炭化物類;水酸化アルミ
ニウム、水酸化ガリウム、水酸化インジウム、水
酸化タリウム、酸化タリウム等のアルミニウム族
金属の水酸化物及び酸化物類;酸化ランタン、酸
化セリウム、水酸化セリウム等の希土類元素の酸
化物及び水酸化物類;水素化リチウム、水酸化ナ
トリウム、ホウ水素化ナトリウム、水素化カルシ
ウム、水素化リチウムアルミニウム等の水素化物
類;硫化ナトリウム、硫化水素ナトリウム、硫化
カリウム、硫化カルシウム等のアルカリ金属又は
アルカリ土類金属の硫化物及び硫化水素化合物
類;水酸化テトラエチルアンモニウム、水酸化テ
トラプロピルアンモニウム等の水酸化4級アンモ
ニウム化合物類;水酸化メチルトリフエニルホス
ホニウム、水酸化テトラメチルホスホニウム等の
水酸化4級ホスホニウム化合物類;水酸化トリエ
チルスルホニウム、水酸化トリフエニルスルホニ
ウム等の水酸化3級スルホニウム化合物類;酢酸
ナトリウム、安息香酸カリウム、シユウ酸ルビジ
ウム、プロピオン酸バリウム等の強塩基と弱有機
酸との塩類;ナトリウムメチラート、ナトリウム
エチラート、カルシウムエチラート等のアルカリ
金属及びアルカリ土類金属のアルコラート類;ナ
トリウムフエノラート、カリウムフエノラート、
マグネシウムフエノラート等のアルカリ金属及び
アルカリ土類金属のフエノラート類;リチウムア
ミド、ナトリウムアミド、カルシウムアミド、リ
チウムジメチルアミド等のアルカリ金属及びアル
カリ土類金属のアミド類;トリメチルアミン、ト
リエチルアミン、トリ−n−ブチルアミン、トリ
フエニルアミン、ジエチルメチルアミン、N,N
−ジエチルアニリン、N−メチルピペリジン、
N,N′−ジエチルピペラジン、N−メチルモル
ホリン、トリエチレンジアミン、ヘキサメチレン
テトラミン、N,N,N′,N′−テトラメチルエ
チレンジアミン、ジシクロヘキシルエチルアミ
ン、1,2,2,6,6−ペンタメチルピペリジ
ン、ピリジン、キノリン、インドール、N−メチ
ルイミダゾール、1,8−ジアザビシクロ−〔5,
4,0〕−ウンデセン−7(DBU)、1,5−ジア
ザビシクロ−〔4,3,0〕−ノネン−5(DBN)
等の3級アミン類や環状含窒素化合物類(ただし
N−H基をもたないもの);クラウンエーテル、
アザクラウンエーテル、チアクラウンエーテル、
アザクラウンなどのクラウン化合物類及びこれら
のクラウン化合物とアルカリ金属やアルカリ土類
金属イオンなどとの錯体類などが用いられる。さ
らにこれらの塩基性を示すグループが分子内に2
個以上あつてもよいし、例えば水酸化4級アンモ
ニウム基を有する陰イオン交換樹脂のようなポリ
マーの一部を形成するものであつてもよい。また
これらの塩基性物質又は塩基性を有するグループ
が固体に担持されたり、化学的に結合されている
ものであつてもよい。
また本発明で追加的助触媒として用いられるキ
レート試薬としては、ジメチルグリオキシム、ベ
ンジルジオキシム、1,2−シクロヘキサンジオ
ンジオキシムなどのα−ジオキシム類;2,2′−
ビピリジン、2,2′−ビキノリン、ターピリジン
などのビピリジン及びターピリジン類;o−フエ
ナンスロリン、4,7−ジフエニル−o−フエナ
ンスロリン、2,9−ジメチル−o−フエナンス
ロリン、2,9−ジメチル−4,7−ジフエニル
−o−フエナンスロリン、4,7−ジヒドロキシ
−o−フエナンスロリンなどのo−フエナンスロ
リン類;8−ヒドロキシキノリン、5,7−ジク
ロル−8−ヒドロキシキノリン、5,7−ジブロ
ム−8−ヒドロキシキノリン、5,7−ジヨード
−8−ヒドロキシキノリン、2−メチル−8−ヒ
ドロキシキノリンなどの8−ヒドロキシキノリン
類;キナルジン酸、キノリン−8−カルボン酸な
どのキノリンカルボン酸類などがあげられる。
追加的助触媒として用いることのできるこれら
の塩基性物質あるいはキレート試薬は単独で用い
てもよいし、あるいは2種以上混合して用いても
よい。またその使用量についても特に制限はない
が、ハロゲン化合物に対して通常0.01〜1000倍モ
ルの範囲、又は白金族元素を含む成分の中の金属
元素の量に対して、通常0.01〜10000倍モルの範
囲で使用されるのが好ましい。
本発明の原料として用いられる尿素化合物は式
で示されるような尿素結合を1分子中に少くとも
1つ含む化合物のことである。ここで、Nに連な
る2本の線は、窒素原子と他の原子又は基との結
合手を表わす。このような原子又は基としては水
素、ハロゲン、アルカリ金属原子、ヒドロキシル
基、アミノ基、脂肪族基、脂環族基、芳香脂肪族
基、複素環式基、芳香族基などがある。またこれ
らの窒素はそれ自身、環を構成する要素となつて
いてもよいし、尿素結合自身が環を構成する一部
となつているようなものであつてもよい。
このような尿素化合物としては未置換尿素、モ
ノ置換尿素、ジ置換尿素、トリ置換尿素、テトラ
置換尿素などいずれであつてもよい。
モノ置換尿素としては例えば、メチル尿素、エ
チル尿素、プロピル尿素、ブチル尿素、ヘキシル
尿素等の脂肪族モノ置換尿素類;シクロプロピル
尿素、シクロブチル尿素、シクロヘキシル尿素等
の脂環族モノ置換尿素類;ベンジル尿素、β−フ
エネチル尿素等の芳香脂肪族モノ置換尿素類;フ
ラニル尿素、チオフエニル尿素等の複素環式モノ
置換尿素類;フエニル尿素、トリル尿素、ナフチ
ル尿素等の芳香族モノ置換尿素類などが用いられ
る。ジ置換尿素としては例えば、N,N−ジメチ
ル尿素、N,N−ジエチル尿素、N,N−ジプロ
ピル尿素、N,N−ジブチル尿素、N,N−ジヘ
キシル尿素、N−エチル−N−メチル尿素、N−
エチル−N−ブチル尿素等の脂肪族N,N−ジ置
換尿素類;N,N−ジシクロプロピル尿素、N,
N−ジシクロブチル尿素、N,N−ジシクロヘキ
シル尿素;N−シクロプロピル−N−メチル尿
素、N−シクロヘキシル−N−エチル尿素等の脂
環族N,N−ジ置換尿素類;N,N−ジベンジル
尿素、N−ベンジル−N−メチル尿素等の芳香脂
肪族N,N−ジ置換尿素類;N,N−ジフラニル
尿素、N,N−ジチオフエニル尿素、N−フラニ
ル−N−メチル尿素等の複素環式N,N−ジ置換
尿素類;N,N−ジフエニル尿素、N,N−ジト
リル尿素、N,N−ジナフチル尿素、N−フエニ
ル−N−メチル尿素、N−フエニル−N−トリル
尿素、N−ナフチル−N−ベンジル尿素、N−フ
エニル−N−シクロヘキシル尿素等の芳香族N,
N−ジ置換尿素類;N,N′−ジメチル尿素、N,
N′−ジエチル尿素、N,N′−ジプロピル尿素、
N,N′−ジブチル尿素、N,N′−ジヘキシル尿
素、N−エチル−N′−メチル尿素、N−エチル
−N′−ブチル尿素、N−ヘキシル−N′−メチル
尿素などの脂肪族N,N′−ジ置換尿素類;N,
N′−ジシクロプロピル尿素、N,N′−ジシクロ
ブチル尿素、N,N′−ジシクロヘキシル尿素、
N−シクロプロピル−N′−メチル尿素、N−シ
クロヘキシル−N′−エチル尿素等の脂環族N,
N′−ジ置換尿素類;N,N′−ジベンジル尿素、
N−ベンジル−N′−メチル尿素の芳香脂肪族N,
N′−ジ置換尿素類;N,N′−ジフラニル尿素、
N,N′−ジチオフエニル尿素等の複素環式N,
N′−ジ置換尿素類;N,N′−ジフエニル尿素、
N,N′−ジトリル尿素、N,N′−ジナフチル尿
素、N−フエニル−N′−トリル尿素、N−フエ
ニル−N′−ナフチル尿素、N−フエニル−N′−
エチル尿素、N−ナフチル−N′−ベンジル尿素、
N−フエニル−N′−シクロヘキシル等の芳香族
N,N′−ジ置換尿素類およびピペリジル尿素、
ピロリジニル尿素等の環状窒素化合物の尿素類な
どが用いられる。トリ置換尿素類としては例え
ば、トリメチル尿素、トリエチル尿素、トリプロ
ピル尿素、トリブチル尿素、トリヘキシル尿素、
N,N−ジメチル−N′−エチル尿素、N,N−
ジエチル−N′−ブチル尿素、N−メチル−N−
エチル−N′−ブチル尿素等の脂肪族トリ置換尿
素類;トリシクロプロピル尿素、トリシクロヘキ
シル尿素、N,N′−ジシクロヘキシル−N′−メ
チル尿素、N−シクロヘキシル−N′−メチル尿
素、N−シクロヘキシル−N−エチル−N′−ブ
チル尿素、N,N−ジエチル−N′−シクロブチ
ル尿素等の脂環族トリ置換尿素類;トリフラニル
尿素、トリチオフエニル尿素、N,N′−ジフラ
ニル−N−メチル尿素等の複素環式トリ置換尿素
類;トリフエニル尿素、トリトリル尿素、トリナ
フチル尿素、N,N−ジフエニル−N′−メチル
尿素、N,N′−ジフエニル−N−シクロヘキシ
ル尿素、N,N′−ジメチル−N′−フエニル尿素、
N−フエニル−N−エチル−N′−ベンジル尿素
等の芳香族トリ置換尿素類;N−エチルピペリジ
ル尿素、N−メチルプロリジニル尿素等のN−置
換の環状窒素化合物の尿素類などが用いられる。
テトラ置換尿素としては例えばテトラメチル尿
素、テトラエチル尿素、テトラプロピル尿素、テ
トラヘキシル尿素、ジエチルメチル尿素、エチル
トリメチル尿素等の脂肪族テトラ置換尿素類;テ
トラシクロプロピル尿素、テトラシクロヘキシル
尿素、ジシクロヘキシルジエチル尿素、シクロブ
チルトリメチル尿素等の脂環族テトラ置換尿素
類;テトラベンジル尿素、トリベンジルメチル尿
素、ジベンジルジエチル尿素、ベンジルトリメチ
ル尿素等の芳香脂肪族テトラ置換尿素類;テトラ
フラニル尿素、テトラチオフエニル尿素、フラニ
ルトリメチル尿素等の複素環式テトラ置換尿素
類;テトラフエニル尿素、テトラトリル尿素、テ
トラナフチル尿素、メチルトリフエニル尿素、ジ
エチルジフエニル尿素、ジシクロヘキシルジフエ
ニル尿素、ナフチルトリエチル尿素等の芳香族テ
トラ置換尿素類などが用いられる。また尿素結合
を環の構成要素とする環状尿素化合物としては例
えば、2−イミダゾロン、2−イミダゾリドン、
ビオチン、ヒダントイン、N,N′−ヘキサメチ
レン尿素、パラバン酸、ベンツイミダゾリドンな
どが用いられる。
さらには分子内に2個以上の尿素結合を有する
化合物、例えばN,N′−ジメチルカルバモイル
ヘキサメチレンジアミン、N,N′−ジフエニル
カルバモイルフエニレンジアミンなどのポリアミ
ンのポリ尿素類あるいは次式で表わされるような
構造単位を有するポリメリツク尿素類なども用い
ることができる。
またこれらの置換尿素類においては置換基の1
個以上の水素が他の置換基、例えば低級脂肪族
基、アミノ基、カルボキシル基、エステル基、ア
ルコキシ基、シアノ基、ハロゲン、ニトロ基、ウ
レタン基、スルホキシド基、スルホン基、カルボ
ニル基、アミド基、芳香族基、芳香脂肪族基など
によつて置換されているものであつてもよい。
イソシアナート類の製造原料としてのウレタン
化合物を得るためにはN,N′−ジ置換尿素類が
好ましく、特に芳香族ウレタン化合物はN,
N′−ジアリール尿素類を用いることによつて容
易に製造される。
これらの尿素化合物は1種またはそれ以上で用
いられる。
本発明に用いる有機ヒドロキシル化合物は、1
価又は多価のアルコール類、あるいは1価又は多
価のフエノール類であり、このようなアルコール
類としては、例えば炭素数1〜20の直鎖又は分枝
鎖の1価又は多価アルカノールやアルケノール、
1価又は多価のシクロアルカノールやシクロアル
ケノールやアラルキルアルコールなどがあげられ
る。さらにこれらのアルコール類は他の置換基、
例えばハロゲン原子、シアノ基、アルコキシ基、
スルホキシド基、スルホン基、カルボニル基、エ
ステル基、アミド基などを含んでいてもよい。
このようなアルコール類の具体例として、メタ
ノール、エタノール、プロパノール(各異性体)、
ブタノール(各異性体)、ペンタノール(各異性
体)、ヘキサノール(各異性体)、ヘプタノール
(各異性体)、オクタノール(各異性体)、ノニル
アルコール(各異性体)、デシルアルコール(各
異性体)、ウンデシルアルコール(各異性体)、ラ
ウリルアルコール(各異性体)、トリデシルアル
コール(各異性体)、テトラデシルアルコール
(各異性体)、ペンタデシルアルコール(各異性
体)などの脂肪族アルコール類;シクロヘキサノ
ール、シクロヘプタノールなどのシクロアルカノ
ール類;エチレングリコールモノメチルエーテ
ル、エチレングリコールモノエチルエーテル、ジ
エチレングリコールモノメチルエーテル、ジエチ
レングリコールモノエチルエーテル、トリエチレ
ングリコールモノメチルエーテル、トリエチレン
グリコールモノエチルエーテル、プロピレングリ
コールモノメチルエーテル、プロピレングリコー
ルモノエチルエーテルなどアルキレングリコール
モノエーテル類;エチレングリコール、プロピレ
ングリコール、ジエチレングリコール、ジプロピ
レングリコール、グリセリン、ヘキサントリオー
ル、トリメチロールプロパンなどの多価アルコー
ル類;ベンジルアルコールなどのアラルキルアル
コール類などが用いられる。
またフエノール類としては例えば、フエノー
ル、各種アルキルフエノール、各種アルコキシフ
エノール、各種ハロゲン化フエノール、ジヒドロ
キシベンゼン、4,4′−ジヒドロキシ−ジフエニ
ルメタン、ビスフエノール−A、ヒドロキシナフ
タレンなどが用いられる。
本発明において用いられる酸化剤としては、通
常の酸化剤を使用しうるが、好ましいものは分子
状酸素又は有機ニトロ化合物若しくはこれらの混
合物である。特に好ましいのは分子状酸素であ
る。この分子状酸素とは純酸素又は酸素を含むも
のであつて空気でもよいし、あるいは空気又は純
酸素に反応を阻害しない他のガス、例えば窒素、
アルゴン、ヘリウム、炭酸ガスなどの不活性ガス
を加えて希釈したものであつてもよい。また場合
によつては、水素、一酸化炭素、炭化水素、ハロ
ゲン化炭化水素などのガスを含んでいてもよい。
また、有機ニトロ化合物としては脂環族、脂肪
族及び芳香族のいずれのニトロ化合物であつても
よい。脂環族ニトロ化合物としては、例えばニト
ロシクロブタン、ニトロシクロペンタン、ニトロ
シクロヘキサン、ジニトロシクロヘキサン(各異
性体)、ビス−(ニトロシクロヘキシル)−メタン
などが、脂肪族ニトロ化合物としては、例えばニ
トロメタン、ニトロエタン、ニトロプロパン(各
異性体)、ニトロブタン(各異性体)、ニトロペン
タン(各異性体)、ニトロヘキサン(各異性体)、
ニトロデカン(各異性体)、1,2−ジニトロエ
タン、ジニトロプロパン(各異性体)、ジニトロ
ブタン(各異性体)、ジニトロペンタン(各異性
体)、ジニトロヘキサン(各異性体)、ジニトロデ
カン(各異性体)、フエニルニトロメタン、ビス
−(ニトロメチル)−シクロヘキサン、ビス−(ニ
トロメチル)−ベンゼンなどが、芳香族ニトロ化
合物としては、例えばニトロベンゼン、ジニトロ
ベンゼン(各異性体)、ニトロトルエン(各異性
体)、ジニトロトルエン(各異性体)、ニトロピリ
ジン(各異性体)、ジニトロピリジン(各異性
体)、ニトロナフタレン(各異性体)、ジニトロナ
フタレン(各異性体)等があげられる。
また、これらのニトロ化合物において、少なく
とも1個の水素が他の置換基、例えばハロゲン原
子、アミノ基、シアノ基、アルキル基、脂環族
基、芳香族基、アラルキル基、アルコキシ基、ス
ルホキシド基、スルホン基、カルボニル基、エス
テル基、アミド基などで置換されていてもよい。
本発明において酸化剤が分子状酸素の場合は、
次のような一般的な反応式に従つて進行する。
(ここでR1、R2、R3、R4は水素、脂肪族基、脂
環族基、芳香脂肪族基、複素環式基、芳香族基か
ら選ばれた原子又は基を、Rは有機基を表わす)
分子状酸素は当量よりも少なくても、多くても
よいが、酸素/一酸化炭素又は酸素/有機ヒドロ
キシル化合物の混合物は爆発限界外で使用すべき
である。
また、有機ニトロ化合物を酸化剤として用いる
場合、有機ニトロ化合物自体も反応に与かりウレ
タンとなるので、その有機基の構造が尿素化合物
の置換基と異なれば、それぞれの構造に応じたウ
レタン化合物が得られ、両者の構造が同じであれ
ば同じウレタン化合物が得られることはいうまで
もない。
この場合、ウレタン化反応は例えば次のような
反応式に従つて進行する。
(ここでR1、R2、R3、R4およびRは前記と同じ
意味をもち、R′は有機ニトロ化合物の有機残基
を表わす)
有機ニトロ化合物だけを酸化剤として用いる場
合、尿素化合物と有機ニトロ化合物の量比は、尿
素基2モル当りニトロ基1モルとなるようにする
のが好ましいが、もちろんこの化学量論量比から
離れたところで実施してもかまわない。一般に尿
素基のニトロ基に対する当量比は1.1:1ないし
4:1、好ましくは1.5:1ないし2.5:1で実施
される。
もちろん分子状酸素あるいはその他の酸化剤を
同時に使用する場合には有機ニトロ化合物は化学
量論量より少なくてもよい。
本発明方法においては、反応溶媒として有機ヒ
ドロキシル化合物を過剰に用いることが好ましい
が、必要に応じて反応に悪影響を及ぼさない溶媒
を用いることもできる。このような溶媒として
は、例えばベンゼン、トルエン、キシレン、メシ
チレンなどの芳香族炭化水素類;アセトニトリ
ル、ベンゾニトリルなどのニトリル類;スルホラ
ン、メチルスルホラン、ジメチルスルホランなど
のスルホン類;テトラヒドロフラン、1,4−ジ
オキサン、1,2−ジメトキシエタンなどのエー
テル類;アセトン、メチルエチルケトンなどのケ
トン類;酢酸エチル、安息香酸エチルなどのエス
テル類;N,N−ジメチルホルムアミド、N,N
−ジメチルアセトアミド、N−メチルピロリド
ン、ヘキサメチルホスホルアミドなどのアミド類
などがあげられる。
さらには、本発明の触媒成分として用いられる
有機ハロゲン化物の1種であるクロルベンゼン、
ジクロルベンゼン、トリクロルベンゼン、フルオ
ロベンゼン、クロルトルエン、クロルナフタレ
ン、ブロムナフタレンなどのハロゲン化芳香族炭
化水素類;クロルヘキサン、クロルシクロヘキサ
ン、トリクロルトリフルオロエタン、塩化メチレ
ン、四塩化炭素などのハロゲン化脂肪族炭化水素
あるいはハロゲン化脂環族炭化水素類なども溶媒
として用いられる。
本発明方法において、反応をより効率的に行う
ために必要に応じて他の添加物を反応系に加える
こともできる。このような添加物として、例え
ば、ゼオライト類、オルソエステル類、ケタール
類、アセタール類、エノールエーテル類、トリア
ルキルオルソホウ酸エステル類などが好適であ
る。
本発明方法において、反応は通常80〜300℃、
好ましくは120〜220℃の温度範囲で行われる。ま
た反応圧力は1〜500Kg/cm2、好ましくは20〜300
Kg/cm2の範囲であり、反応時間は反応系、触媒系
およびその他の反応条件によつて異なるが、通常
数分〜数時間である。
次に実施例によつて本発明をさらに詳細に説明
するが、本発明は、これらの実施例に限定される
ものではない。
実施例 1
500mlオートクレーブにN,N′−ジフエニル尿
素100mmol、エタノール120ml、ヨウ化ナトリウ
ム3mmol、粉末状SiO2に2w%のPdを担持した
Pd/SiO28gを入れ、系内を一酸化炭素で置換し
た後、撹拌しながら160〜170℃に加熱した。所定
温度に達した後、一酸化炭素75%、空気25%から
成る混合ガス80Kg/cm2の圧力下で60N/hrの流
量で導入しながら撹拌下に反応を行つた。この反
応装置はオートクレーブの上部に部分凝縮器が設
置されており、凝縮性ガス成分は必要に応じて部
分的に又は全量凝縮させて反応器に循環させるこ
とが可能であり、もちろん反応器に循環しないで
凝縮させた液状成分の全量を反応系外に除去する
ことも可能である。また反応器内の液量を所定量
に保つために必要に応じて、液成分をポンプで反
応器内に連続的に注入することも可能である。
反応によつて生成してくる水をエタノールの一
部と共に、ほぼ全量反応系外に除去した場合と、
50%除去した場合、及び全然除去せずに全量反応
系内に留置した場合についての、1時間後の反応
成績は第1表の通りであつた。なおこの反応にお
いてエタノールを留出させる場合は、その量に見
合つた量を連続的に反応器に供給して、液量をほ
ぼ一定に保つた。[Formula] (In the formula, R 1 , R 2 , R 3 , and Acids and their salts, specifically hypochlorous acid, chlorous acid, chloric acid, perchloric acid, hypobromous acid, bromate acid, perbromate acid, hypoiodic acid, and iodic acid. , iodic acid, orthoperiodic acid, metaperiodic acid, and salts of these acids. The cation of the salts may be any one such as ammonium ion and various metal ions, but alkali metal ions and alkaline earth metal ions are preferred. Examples of such salts include hypochlorites such as sodium hypochlorite, potassium hypochlorite, calcium hypochlorite, and barium hypochlorite;
Chlorites such as sodium chlorite; lithium chlorate, sodium chlorate, potassium chlorate,
Chlorates such as rubidium chlorate, cesium chlorate, magnesium chlorate, calcium chlorate, barium chlorate, aluminum perchlorate, calcium perchlorate, barium perchlorate, zinc perchlorate, cadmium perchlorate, Perchlorates such as mercury perchlorate, cerium perchlorate, lead perchlorate, and ammonium perchlorate; hypobromites such as sodium hypobromite and potassium hypobromite, sodium bromite, etc. Bromites; lithium bromate, sodium bromate, potassium bromate, rubidium bromate, cesium bromate, magnesium bromate, calcium bromate, strontium bromate,
Barium bromate, silver bromate, zinc bromate, cadmium bromate, mercury bromate, aluminum bromate,
Lanthanum bromate, samarium bromate, lead bromate,
Bromates such as ammonium bromate; perbromates such as potassium perbromate; sodium hypoiodite, potassium hypoiodite, rubidium hypoiodite, cesium hypoiodite, calcium hypoiodite, Hypoiodates such as barium hypoiodate; lithium iodate, sodium iodate, potassium iodate, potassium hydrogen iodate,
Rubidium iodate, cesium iodate, magnesium iodate, calcium iodate, strontium iodate, barium iodate, silver iodate, gold iodate, zinc iodate, cadmium iodate, mercury iodate, aluminum iodate, iodate Iodates such as indium, lanthanum iodate, cerium iodate, proseodymium iodate, neodymium iodate, gadolinium iodate, lead iodate, ammonium iodate; lithium periodate, sodium metaperiodate, orthoperiodate Trisodium dihydrogen, disodium trihydrogen orthoperiodate, potassium metaperiodate, dipotassium trihydrogen orthoperiodate, tripotassium hydrogenhydrogen dimesoperiodate, rubidium periodate, cesium periodate, periodate barium acid,
Periodic acids such as silver metaperiodate, silver mesoperiodate, silver orthoperiodate, silver trihydrogen orthoperiodate, zinc periodate, cadmium periodate, lead periodate, and ammonium periodate. Salts etc. are used. A halogen-containing complex compound may contain either a cationic or anionic halogen; for example, polyhalogenated halogenated salts such as ammonium dichlorobromate and tetramethylammonium tetrabromoiodate; hexaiodine; Potassium tellate, tetraethylammonium tetraiodomercurate, potassium tetraiodobismuthate,
Metal halides such as sodium tetrabromocuprate, cesium tetrabromoferrate, barium hexaiodostannate, potassium tetraiodoleanate, potassium hexabromotellurate; tin tetrabromo(diethylsuccinate), octate (N,
N-dimethylformamide) lanthanum triiodide, hexakis(urea) chromium tribromide, hexaammine chromium tribromide, iodopentaammine chromium triiodide, tris(pyridine) chromium tribromide, tris(pyridine) molybdenum triiodide, hexaammine chromium tribromide Complexes having a ligand such as ammine cobalt tribromide and bis(2,2'-bipyridine) copper diiodide are used. In addition, organic halides have the general formula R 6 (X) n (wherein R 6 is an m-valent organic group, X is a halogen, m
means an integer greater than or equal to 1. ), where m is 2 or more,
X may be two or more different halogen species. In addition, halogen X is a heteroatom other than carbon,
For example, it may be bonded with nitrogen, phosphorus, oxygen, sulfur, selenium, etc. Examples of such organic halides include methyl halide, ethyl halide, propyl halide (each isomer), butyl halide (each isomer), amyl halide (each isomer), hexyl halide ( (Each isomer), Octyl halide (Each isomer), Perfluorohexyl halide (Each isomer), Perfluoroheptyl halide (Each isomer), Vinyl halide, Allyl halide, Methylene halide, Haloform, Tetrahalogenmethane, alkylidene halide,
Dihalogenated ethane (each isomer), trihalogenated ethane (each isomer), tetrahalogenated ethane,
Aliphatic mono- and polyhalides such as dihalogenated butane (each isomer), dihalogenated hexane (each isomer), dihaloethylene (each isomer);
Halogenbenzene, dihalogenbenzene (each isomer), trihalogenbenzene (each isomer), tetrahalogenbenzene (each isomer), hexahalogenbenzene, halogennaphthalene, dihalogennaphthalene (each isomer), halogenpyridine (each isomer) ), halogenated toluene (each isomer), halogenated ethylbenzene (each isomer), aromatic mono- and polyhalides such as phenyl iodo dichloride, iodosobenzene, iodoxybenzene; halogenated cyclohexane, halogenated cyclobutane, etc. Alicyclic halides; Aroaliphatic halides such as halogenated benzyl and halogenated phenethyl; Heterocyclic halides such as halogenated furan, halogenated tetrahydrofuran, halogenated thiophene, halogenated imidazole, and halogenated piperidine Acid halides such as halogenated acetyl and halogenated benzoyl; N-halides such as N-halogensuccinimide, N-halogenalkylamine, N-halogenacetamide, and N-halogenbenzamide are preferably used. Furthermore, these organic groups can be substituted with various substituents, such as nitro groups, lower alkyl groups, cyano groups, alkoxy groups, aryloxy groups, aromatic groups, sulfoxide groups, sulfone groups, carbonyl groups, ester groups, amide groups, etc. or may have an unsaturated group. Further, as a compound containing a halogen, hydrogen halides such as hydrogen chloride, hydrogen bromide, and hydrogen iodide, and hydrohalic acid, or halogen molecules themselves such as chlorine, bromine, and iodine can be used. Such halogen-containing compounds may be used alone or in combination of two or more. Further, when the urea compound or organic hydroxyl compound as a reaction raw material, or other components of the catalyst contain a halogen, the addition of the halogen compound can be omitted. Among the halogen-containing compounds used in the method of the present invention, those in which the halogen species is bromine or iodine are preferred, and those containing iodine are particularly preferred. There is no particular restriction on the amount of the halogen compound used in the present invention, but with respect to the amount of the metal element in the component containing the platinum group element used,
It is usually preferable to use it in a range of 0.001 to 10,000 times the mole. Furthermore, the basic substance that can be used as an additional promoter in the present invention may be either inorganic or organic. Examples of such basic substances include alkali metals such as lithium, sodium, and potassium; alkaline earth metals such as magnesium, calcium, and barium; lithium oxide, lithium peroxide, sodium oxide, sodium peroxide, and superoxide. sodium, potassium oxide,
Alkali metal oxides such as potassium peroxide, dipotassium trioxide, potassium superoxide, rubidium oxide, rubidium peroxide, dirubidium trioxide, rubidium superoxide, rubidium ozonide, cesium oxide, cesium peroxide; beryllium oxide , magnesium oxide, calcium oxide, calcium peroxide, strontium oxide, strontium peroxide, barium oxide, barium peroxide, and other alkaline earth metal oxides; lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide , alkali metal and alkaline earth metal hydroxides such as cesium hydroxide, beryllium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide; sodium carbonate, sodium hydrogen carbonate, potassium carbonate, carbonic acid Potassium hydrogen, barium carbonate, sodium silicate, magnesium silicate, potassium aluminate,
Salts of strong bases and weak acids such as calcium aluminate, sodium borate, and barium borate; Carbides such as calcium carbide and cesium carbide; Hydroxides and oxides of aluminum group metals; oxides and hydroxides of rare earth elements such as lanthanum oxide, cerium oxide, and cerium hydroxide; lithium hydride, sodium hydroxide, sodium borohydride, calcium hydride , hydrides such as lithium aluminum hydride; sulfides and hydrogen sulfide compounds of alkali metals or alkaline earth metals such as sodium sulfide, sodium hydrogen sulfide, potassium sulfide, calcium sulfide; tetraethylammonium hydroxide, tetrapropyl hydroxide Quaternary ammonium hydroxide compounds such as ammonium; Quaternary phosphonium hydroxide compounds such as methyltriphenylphosphonium hydroxide and tetramethylphosphonium hydroxide; Tertiary sulfonium hydroxide such as triethylsulfonium hydroxide and triphenylsulfonium hydroxide Compounds: Salts of strong bases such as sodium acetate, potassium benzoate, rubidium oxalate, barium propionate and weak organic acids; Salts of alkali metals and alkaline earth metals such as sodium methylate, sodium ethylate, calcium ethylate, etc. Alcoholates; sodium phenolate, potassium phenolate,
Alkali metal and alkaline earth metal phenolates such as magnesium phenolate; alkali metal and alkaline earth metal amides such as lithium amide, sodium amide, calcium amide, lithium dimethylamide; trimethylamine, triethylamine, tri-n-butylamine , triphenylamine, diethylmethylamine, N,N
-diethylaniline, N-methylpiperidine,
N,N'-diethylpiperazine, N-methylmorpholine, triethylenediamine, hexamethylenetetramine, N,N,N',N'-tetramethylethylenediamine, dicyclohexylethylamine, 1,2,2,6,6-pentamethylpiperidine , pyridine, quinoline, indole, N-methylimidazole, 1,8-diazabicyclo-[5,
4,0]-undecene-7 (DBU), 1,5-diazabicyclo-[4,3,0]-nonene-5 (DBN)
Tertiary amines and cyclic nitrogen-containing compounds such as (but not having an N-H group); crown ether,
Aza Crown Ether, Chia Crown Ether,
Crown compounds such as azacrown and complexes of these crown compounds with alkali metals, alkaline earth metal ions, etc. are used. Furthermore, these basic groups have 2 groups in the molecule.
There may be more than one, or it may form a part of a polymer such as an anion exchange resin having a quaternary ammonium hydroxide group. Further, these basic substances or groups having basicity may be supported on a solid or chemically bonded. In addition, examples of chelating reagents used as additional promoters in the present invention include α-dioximes such as dimethylglyoxime, benzyldioxime, and 1,2-cyclohexanedionedioxime;
Bipyridine and terpyridines such as bipyridine, 2,2'-biquinoline, and terpyridine; o-phenanthroline, 4,7-diphenyl-o-phenanthroline, 2,9-dimethyl-o-phenanthroline, 2,9-dimethyl-4,7 o-phenanthrolines such as -diphenyl-o-phenanthroline and 4,7-dihydroxy-o-phenanthroline; 8-hydroxyquinoline, 5,7-dichloro-8-hydroxyquinoline, 5,7-dibromo-8-hydroxyquinoline, Examples include 8-hydroxyquinolines such as 5,7-diiodo-8-hydroxyquinoline and 2-methyl-8-hydroxyquinoline; and quinolinecarboxylic acids such as quinaldic acid and quinoline-8-carboxylic acid. These basic substances or chelating reagents that can be used as additional promoters may be used alone or in combination of two or more. There is also no particular restriction on the amount used, but it is usually in the range of 0.01 to 1000 times the mole of the halogen compound, or usually 0.01 to 10,000 times the mole of the metal element in the component containing the platinum group element. It is preferable to use it within the range of . The urea compound used as a raw material in the present invention has the formula It refers to a compound containing at least one urea bond in one molecule as shown in the following. Here, the two lines connected to N represent bonds between the nitrogen atom and other atoms or groups. Such atoms or groups include hydrogen, halogen, alkali metal atoms, hydroxyl groups, amino groups, aliphatic groups, alicyclic groups, araliphatic groups, heterocyclic groups, and aromatic groups. Further, these nitrogens may themselves be elements constituting a ring, or the urea bond itself may be a part constituting a ring. Such urea compounds may be unsubstituted urea, monosubstituted urea, disubstituted urea, trisubstituted urea, tetrasubstituted urea, or the like. Examples of monosubstituted ureas include aliphatic monosubstituted ureas such as methylurea, ethylurea, propylurea, butylurea, and hexylurea; alicyclic monosubstituted ureas such as cyclopropylurea, cyclobutylurea, and cyclohexylurea; benzyl Aroaliphatic monosubstituted ureas such as urea and β-phenethylurea; heterocyclic monosubstituted ureas such as furanylurea and thiophenyl urea; aromatic monosubstituted ureas such as phenyl urea, tolylurea and naphthylurea, etc. are used. It will be done. Examples of the disubstituted urea include N,N-dimethylurea, N,N-diethylurea, N,N-dipropylurea, N,N-dibutylurea, N,N-dihexylurea, and N-ethyl-N-methylurea. , N-
Aliphatic N,N-disubstituted ureas such as ethyl-N-butylurea; N,N-dicyclopropylurea, N,
Alicyclic N,N-disubstituted ureas such as N-dicyclobutylurea, N,N-dicyclohexylurea; N-cyclopropyl-N-methylurea, N-cyclohexyl-N-ethylurea; N,N-dibenzylurea , N-benzyl-N-methylurea and other aromatic aliphatic N,N-disubstituted ureas; N,N-difuranylurea, N,N-dithiophenylurea, N-furanyl-N-methylurea and other heterocyclic ureas N,N-disubstituted ureas; N,N-diphenylurea, N,N-ditolylurea, N,N-dinaphthylurea, N-phenyl-N-methylurea, N-phenyl-N-tolylurea, N- Aromatic N such as naphthyl-N-benzylurea, N-phenyl-N-cyclohexylurea,
N-disubstituted ureas; N,N'-dimethylurea, N,
N'-diethylurea, N,N'-dipropylurea,
Aliphatic N such as N,N'-dibutylurea, N,N'-dihexylurea, N-ethyl-N'-methylurea, N-ethyl-N'-butylurea, N-hexyl-N'-methylurea , N'-disubstituted ureas; N,
N'-dicyclopropylurea, N,N'-dicyclobutylurea, N,N'-dicyclohexylurea,
Alicyclic N such as N-cyclopropyl-N'-methylurea, N-cyclohexyl-N'-ethylurea,
N'-disubstituted ureas; N,N'-dibenzylurea,
Aroaliphatic N of N-benzyl-N'-methylurea,
N'-disubstituted ureas; N,N'-difuranylurea,
Heterocyclic N, such as N,N'-dithiophenylurea,
N'-disubstituted ureas; N,N'-diphenylurea,
N,N'-ditolylurea, N,N'-dinaphthylurea, N-phenyl-N'-tolylurea, N-phenyl-N'-naphthylurea, N-phenyl-N'-
Ethyl urea, N-naphthyl-N'-benzylurea,
Aromatic N,N'-disubstituted ureas such as N-phenyl-N'-cyclohexyl and piperidyl urea,
Ureas such as cyclic nitrogen compounds such as pyrrolidinyl urea are used. Examples of tri-substituted ureas include trimethylurea, triethylurea, tripropylurea, tributylurea, trihexylurea,
N,N-dimethyl-N'-ethylurea, N,N-
Diethyl-N'-butyl urea, N-methyl-N-
Aliphatic trisubstituted ureas such as ethyl-N'-butylurea; tricyclopropylurea, tricyclohexylurea, N,N'-dicyclohexyl-N'-methylurea, N-cyclohexyl-N'-methylurea, N- Alicyclic trisubstituted ureas such as cyclohexyl-N-ethyl-N'-butylurea, N,N-diethyl-N'-cyclobutylurea; trifuranylurea, trithiophenylurea, N,N'-difuranyl-N-methylurea Heterocyclic trisubstituted ureas such as triphenylurea, tritolylurea, trinaphthylurea, N,N-diphenyl-N'-methylurea, N,N'-diphenyl-N-cyclohexylurea, N,N'-dimethyl- N′-phenylurea,
Aromatic trisubstituted ureas such as N-phenyl-N-ethyl-N'-benzylurea; N-substituted cyclic nitrogen compound ureas such as N-ethylpiperidylurea and N-methylprolidinyl urea are used. It will be done. Examples of tetra-substituted ureas include aliphatic tetra-substituted ureas such as tetramethylurea, tetraethylurea, tetrapropylurea, tetrahexylurea, diethylmethylurea, and ethyltrimethylurea; tetracyclopropylurea, tetracyclohexylurea, dicyclohexyldiethylurea, Alicyclic tetra-substituted ureas such as cyclobutyltrimethylurea; aromatic aliphatic tetra-substituted ureas such as tetrabenzyl urea, tribenzylmethyl urea, dibenzyl diethyl urea, and benzyl trimethyl urea; tetrafuranylurea, tetrathiophenylurea, Heterocyclic tetra-substituted ureas such as furanyltrimethylurea; aromatic tetra-substituted ureas such as tetraphenylurea, tetratolylurea, tetranaphthylurea, methyltriphenylurea, diethyldiphenylurea, dicyclohexyldiphenylurea, naphthyltriethylurea etc. are used. Examples of cyclic urea compounds having a urea bond as a ring component include 2-imidazolone, 2-imidazolidone,
Biotin, hydantoin, N,N'-hexamethylene urea, parabanic acid, benzimidazolidone, etc. are used. Furthermore, compounds having two or more urea bonds in the molecule, such as polyureas of polyamines such as N,N'-dimethylcarbamoylhexamethylenediamine and N,N'-diphenylcarbamoylphenylenediamine, or compounds represented by the following formula: Polymeric ureas having a structural unit such as that described above can also be used. In addition, in these substituted ureas, one of the substituents
or more hydrogen may be substituted with other substituents, such as lower aliphatic groups, amino groups, carboxyl groups, ester groups, alkoxy groups, cyano groups, halogens, nitro groups, urethane groups, sulfoxide groups, sulfone groups, carbonyl groups, and amide groups. , an aromatic group, an araliphatic group, or the like. In order to obtain a urethane compound as a raw material for producing isocyanates, N,N'-disubstituted ureas are preferable, and aromatic urethane compounds are particularly suitable for N,N'-disubstituted ureas.
It is easily produced using N'-diarylureas. One or more of these urea compounds may be used. The organic hydroxyl compound used in the present invention is 1
or polyvalent or polyhydric alcohols, or monovalent or polyvalent phenols. Examples of such alcohols include linear or branched monovalent or polyhydric alkanols and alkenols having 1 to 20 carbon atoms. ,
Examples include monovalent or polyvalent cycloalkanols, cycloalkenols, and aralkyl alcohols. Furthermore, these alcohols have other substituents,
For example, halogen atoms, cyano groups, alkoxy groups,
It may contain a sulfoxide group, a sulfone group, a carbonyl group, an ester group, an amide group, etc. Specific examples of such alcohols include methanol, ethanol, propanol (each isomer),
Butanol (each isomer), pentanol (each isomer), hexanol (each isomer), heptanol (each isomer), octanol (each isomer), nonyl alcohol (each isomer), decyl alcohol (each isomer) ), undecyl alcohol (each isomer), lauryl alcohol (each isomer), tridecyl alcohol (each isomer), tetradecyl alcohol (each isomer), and aliphatic alcohols such as pentadecyl alcohol (each isomer) Cycloalkanols such as cyclohexanol and cycloheptanol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl Alkylene glycol monoethers such as ether and propylene glycol monoethyl ether; polyhydric alcohols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, glycerin, hexanetriol, and trimethylolpropane; aralkyl alcohols such as benzyl alcohol, etc. used. Examples of phenols that can be used include phenol, various alkylphenols, various alkoxyphenols, various halogenated phenols, dihydroxybenzene, 4,4'-dihydroxy-diphenylmethane, bisphenol-A, and hydroxynaphthalene. The oxidizing agent used in the present invention may be any conventional oxidizing agent, but preferred are molecular oxygen, organic nitro compounds, or mixtures thereof. Particularly preferred is molecular oxygen. This molecular oxygen is pure oxygen or a substance containing oxygen, which may be air, or other gases that do not inhibit the reaction of air or pure oxygen, such as nitrogen,
It may be diluted by adding an inert gas such as argon, helium, or carbon dioxide. In some cases, it may also contain gases such as hydrogen, carbon monoxide, hydrocarbons, and halogenated hydrocarbons. Further, the organic nitro compound may be any of alicyclic, aliphatic, and aromatic nitro compounds. Examples of alicyclic nitro compounds include nitrocyclobutane, nitrocyclopentane, nitrocyclohexane, dinitrocyclohexane (each isomer), bis-(nitrocyclohexyl)-methane, and examples of aliphatic nitro compounds include nitromethane, nitroethane, Nitropropane (each isomer), Nitrobutane (each isomer), Nitropentane (each isomer), Nitrohexane (each isomer),
Nitrodecane (each isomer), 1,2-dinitroethane, dinitropropane (each isomer), dinitrobutane (each isomer), dinitropentane (each isomer), dinitrohexane (each isomer), dinitrodecane (each Aromatic nitro compounds include, for example, nitrobenzene, dinitrobenzene (isomers), nitrotoluene (isomers), phenylnitromethane, bis-(nitromethyl)-cyclohexane, bis-(nitromethyl)-benzene, etc. , dinitrotoluene (each isomer), nitropyridine (each isomer), dinitropyridine (each isomer), nitronaphthalene (each isomer), dinitronaphthalene (each isomer), and the like. In addition, in these nitro compounds, at least one hydrogen has another substituent, such as a halogen atom, an amino group, a cyano group, an alkyl group, an alicyclic group, an aromatic group, an aralkyl group, an alkoxy group, a sulfoxide group, It may be substituted with a sulfone group, carbonyl group, ester group, amide group, etc. In the present invention, when the oxidizing agent is molecular oxygen,
The reaction proceeds according to the following general reaction formula. (Here, R 1 , R 2 , R 3 , and R 4 are atoms or groups selected from hydrogen, aliphatic groups, alicyclic groups, araliphatic groups, heterocyclic groups, and aromatic groups, and R is (representing an organic group) Molecular oxygen may be used in less or more than equivalent amounts, but mixtures of oxygen/carbon monoxide or oxygen/organic hydroxyl compounds should be used outside the explosive limits. In addition, when an organic nitro compound is used as an oxidizing agent, the organic nitro compound itself also participates in the reaction and becomes urethane, so if the structure of the organic group is different from the substituent of the urea compound, the urethane compound depending on the structure It goes without saying that the same urethane compound can be obtained if both structures are the same. In this case, the urethanization reaction proceeds according to the following reaction formula, for example. (Here, R 1 , R 2 , R 3 , R 4 and R have the same meanings as above, and R' represents an organic residue of an organic nitro compound.) When only an organic nitro compound is used as an oxidizing agent, a urea compound The quantitative ratio of the organic nitro compound and the organic nitro compound is preferably 1 mole of nitro group per 2 moles of urea group, but of course it may be carried out at a value far from this stoichiometric ratio. Generally, the equivalent ratio of urea groups to nitro groups is carried out from 1.1:1 to 4:1, preferably from 1.5:1 to 2.5:1. Of course, if molecular oxygen or other oxidizing agents are used at the same time, the amount of organic nitro compound may be less than the stoichiometric amount. In the method of the present invention, it is preferable to use an excess of the organic hydroxyl compound as the reaction solvent, but if necessary, a solvent that does not adversely affect the reaction can also be used. Examples of such solvents include aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; nitriles such as acetonitrile and benzonitrile; sulfones such as sulfolane, methylsulfolane, and dimethylsulfolane; tetrahydrofuran, 1,4- Ethers such as dioxane and 1,2-dimethoxyethane; Ketones such as acetone and methyl ethyl ketone; Esters such as ethyl acetate and ethyl benzoate; N,N-dimethylformamide, N,N
Examples include amides such as -dimethylacetamide, N-methylpyrrolidone, and hexamethylphosphoramide. Furthermore, chlorobenzene, which is a type of organic halide used as a catalyst component of the present invention,
Halogenated aromatic hydrocarbons such as dichlorobenzene, trichlorobenzene, fluorobenzene, chlorotoluene, chlornaphthalene, and bromonaphthalene; halogenated fats such as chlorhexane, chlorocyclohexane, trichlorotrifluoroethane, methylene chloride, and carbon tetrachloride Group hydrocarbons or halogenated alicyclic hydrocarbons are also used as solvents. In the method of the present invention, other additives may be added to the reaction system as necessary in order to carry out the reaction more efficiently. Suitable examples of such additives include zeolites, orthoesters, ketals, acetals, enol ethers, and trialkylorthoborates. In the method of the present invention, the reaction is usually carried out at 80 to 300°C.
Preferably it is carried out at a temperature range of 120 to 220°C. The reaction pressure is 1 to 500Kg/cm 2 , preferably 20 to 300Kg/cm 2 .
Kg/cm 2 , and the reaction time varies depending on the reaction system, catalyst system, and other reaction conditions, but is usually from several minutes to several hours. Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples. Example 1 100 mmol of N,N'-diphenylurea, 120 ml of ethanol, 3 mmol of sodium iodide, and 2 w% Pd supported on powdered SiO 2 in a 500 ml autoclave.
After adding 8 g of Pd/SiO 2 and replacing the inside of the system with carbon monoxide, the system was heated to 160 to 170° C. with stirring. After reaching a predetermined temperature, a reaction was carried out with stirring while introducing a mixed gas of 75% carbon monoxide and 25% air under a pressure of 80 kg/cm 2 at a flow rate of 60 N/hr. This reactor is equipped with a partial condenser at the top of the autoclave, and condensable gas components can be partially or completely condensed as necessary and circulated to the reactor. It is also possible to remove the entire amount of the condensed liquid component from the reaction system without doing so. Further, in order to maintain the liquid amount in the reactor at a predetermined level, it is also possible to continuously inject liquid components into the reactor using a pump, as necessary. A case in which almost the entire amount of water produced by the reaction is removed from the reaction system together with a part of the ethanol;
Table 1 shows the reaction results after 1 hour when 50% was removed and when the entire amount was left in the reaction system without being removed at all. In addition, when distilling ethanol in this reaction, an amount commensurate with the amount was continuously supplied to the reactor to keep the liquid amount almost constant.
【表】
選択率A及びBは、それぞれ尿素化合物及び一
酸化炭素基準のウレタンの選択率を表わす。
実施例 2〜10
第2表に示す種々のハロゲン化合物及び塩基性
物質又はキレート試薬を用いる以外は、実施例1
と同様に反応を行つた結果を第2表に示す。これ
らの実施例においては、反応で生成する水はエタ
ノールの一部と共に、ほぼ全量除去した。また留
出させるエタノール量に相当するエタノールを連
続的に供給し、液量をほぼ一定に保つた。また選
択率A、Bは前記と同じ意味を表わす。[Table] Selectivity A and B represent the selectivity of urethane based on urea compound and carbon monoxide, respectively. Examples 2-10 Example 1 except that various halogen compounds and basic substances or chelating reagents shown in Table 2 are used.
Table 2 shows the results of the reaction conducted in the same manner as above. In these Examples, almost all of the water produced in the reaction was removed along with a portion of the ethanol. In addition, ethanol corresponding to the amount of ethanol to be distilled was continuously supplied to keep the liquid amount almost constant. Further, selectivity A and B represent the same meaning as above.
【表】
実施例 11
N,N′−ジシクロヘキシル尿素100mmol、n
−プロパノール150ml、ヨウ化ナトリウム3m
mol、Pd黒1.5mgatomを用い実施例1と同様な方
法により反応を行つた。反応により生成する水は
ほぼ全量、n−プロパノールの一部と共に留出さ
せた。また系外に留出させた量に相当するだけの
n−プロパノールを反応器に連続的に供給した。
1時間後の反応成績は次の通りであつた。N,
N′−ジシクロヘキシル尿素の反応率は100%で、
N−シクロヘキシルカルバミン酸n−プロピルの
収率は98%で、選択率はN,N′−ジシクロヘキ
シル尿素基準で98%、一酸化炭素基準で94%であ
つた。水を系外に除去しないで同様の反応を行つ
たところN,N′−ジシクロヘキシル尿素の反応
率は96%で、N−シクロヘキシルカルバミン酸n
−プロピルの収率は89%で、N,N′−ジシクロ
ヘキシル尿素基準の選択率は93%であつたが、一
酸化炭素基準の選択率は89%であつた。
実施例 12
N,N′−ジベンジル尿素100mmol、ヨウ化テ
トラエチルアンモニウム3mmol、Pd黒1mg
atom、エタノール120mlを実施例1で用いたのと
同じオートクレーブに入れ、系内を一酸化炭素で
置換した後、160〜170℃に昇温し、次いで一酸化
炭素15vol%、酸素5vol%、窒素80vol%から成る
混合ガスを100Kg/cm2の圧力下、60N/hrの流
量で導入しながら撹拌下に反応を行つた。生成し
てくる水はエタノールの一部と共に留出させ、エ
タノールはその分だけ連続的に反応器に供給し
た。1.5時間後のN,N′−ジベンジル尿素の反応
率は98%でN−ベンジルカルバミン酸エチルの収
率は96%で、N,N′−ジベンジル尿素基準の選
択率は98%で、一酸化炭素基準の選択率は95%で
あつた。
実施例 13
N,N′−ジフエニル尿素100mmol、ニトロベ
ンゼン50mmol、エタノール150ml、塩化パラジ
ウム10mmol、ヨウ化カリウム15mmolを実施例
1で用いたのと同じオートクレーブに入れ、系内
を一酸化炭素で置換した後、160〜170℃に加熱し
た。所定の温度に達した後、一酸化炭素を150
Kg/cm2圧力下、50N/hrの流量で導入した。生
成してくる水はエタノールの一部と共に除き、留
出した分だけエタノールを連続的に供給しながら
撹拌下に3時間反応させた結果、N,N′−ジフ
エニル尿素およびニトロベンゼンの反応率はそれ
ぞれ47%及び43%で、N−フエニルカルバミン酸
エチルが82mmol生成していた。一酸化炭素のウ
レタン化反応への選択率は91%であつた。水を除
去しないで同様の反応を行つたところ、N−フエ
ニルカルバミン酸エチルが70mmol生成してお
り、一酸化炭素のウレタン化反応への選択率は76
%であつた。
実施例 14〜18
実施例1におけるPd/SiO2の代りに第3表に
示す種々の白金族触媒を用いる以外は実施例1と
同様な方法により、生成してくる水をほぼ全量除
去しながら反応を行つた結果を第3表に示す。な
お選択率A、Bは前記に示した通りである。また
白金族触媒は金属元素として2mgatomを用い、
%表示は担体に担持された金属の重量%を示す。[Table] Example 11 N,N'-dicyclohexyl urea 100 mmol, n
-Propanol 150ml, sodium iodide 3m
The reaction was carried out in the same manner as in Example 1 using 1.5 mg of Pd black. Almost all of the water produced by the reaction was distilled off along with a portion of n-propanol. Further, n-propanol was continuously supplied to the reactor in an amount corresponding to the amount distilled out of the system.
The reaction results after 1 hour were as follows. N,
The reaction rate of N′-dicyclohexyl urea is 100%,
The yield of n-propyl N-cyclohexylcarbamate was 98%, and the selectivity was 98% based on N,N'-dicyclohexylurea and 94% based on carbon monoxide. When a similar reaction was carried out without removing water from the system, the reaction rate of N,N'-dicyclohexylurea was 96%, and the reaction rate of N-cyclohexylcarbamate n
The yield of -propyl was 89%, and the selectivity based on N,N'-dicyclohexylurea was 93%, but the selectivity based on carbon monoxide was 89%. Example 12 100 mmol of N,N'-dibenzylurea, 3 mmol of tetraethylammonium iodide, 1 mg of Pd black
Atom and 120ml of ethanol were placed in the same autoclave as used in Example 1, and after replacing the system with carbon monoxide, the temperature was raised to 160-170℃, and then 15vol% of carbon monoxide, 5vol% of oxygen, and nitrogen The reaction was carried out under stirring while introducing a mixed gas consisting of 80 vol % under a pressure of 100 Kg/cm 2 at a flow rate of 60 N/hr. The produced water was distilled off along with a portion of the ethanol, and that amount of ethanol was continuously supplied to the reactor. After 1.5 hours, the reaction rate of N,N'-dibenzylurea was 98%, the yield of ethyl N-benzylcarbamate was 96%, the selectivity based on N,N'-dibenzylurea was 98%, and the monoxide The selectivity of the carbon standard was 95%. Example 13 100 mmol of N,N'-diphenylurea, 50 mmol of nitrobenzene, 150 ml of ethanol, 10 mmol of palladium chloride, and 15 mmol of potassium iodide were placed in the same autoclave as used in Example 1, and the system was replaced with carbon monoxide. , heated to 160-170℃. After reaching the predetermined temperature, carbon monoxide to 150
It was introduced at a flow rate of 50 N/hr under Kg/cm 2 pressure. The produced water was removed along with a portion of the ethanol, and the reaction was continued for 3 hours with stirring while continuously supplying ethanol corresponding to the distilled amount. As a result, the reaction rates of N,N'-diphenylurea and nitrobenzene were as follows. At 47% and 43%, 82 mmol of ethyl N-phenylcarbamate was produced. The selectivity of carbon monoxide to the urethanization reaction was 91%. When a similar reaction was carried out without removing water, 70 mmol of ethyl N-phenylcarbamate was produced, and the selectivity of carbon monoxide to the urethanization reaction was 76
It was %. Examples 14 to 18 The same method as in Example 1 was used except that various platinum group catalysts shown in Table 3 were used instead of Pd/SiO 2 in Example 1, while almost all of the generated water was removed. The results of the reaction are shown in Table 3. Note that the selectivities A and B are as shown above. In addition, the platinum group catalyst uses 2mgatom as the metal element,
The % display indicates the weight % of the metal supported on the carrier.
【表】
実施例 19
次式で表わされる構成単位
を有する陰イオン交換樹脂(Amberlyst
A−
26、OH型)をヨウ化水素酸で処理することによ
つてヒドロキシル基をヨウ素アニオンで交換し、
次いで減圧下100℃で乾燥させた。
このヨウ素含有陰イオン交換樹脂4g、N,
N′−ジフエニル尿素80mmol、エタノール120ml、
パラジウム黒1mgatomを用い実施例1と同様の
方法により、水をエタノールの一部と共に留去
し、留出した分だけエタノールを連続的に供給し
ながら1時間反応を行つた結果、N,N′−ジフ
エニル尿素の反応率は100%、N−フエニルカル
バミン酸エチルの収率は99%で、N,N′−ジフ
エニル尿素基準の選択率は99%で、一酸化炭素基
準の選択率は95%であつた。[Table] Example 19 Constituent unit expressed by the following formula Anion exchange resin (Amberlyst A-
26, OH type) was treated with hydroiodic acid to exchange the hydroxyl group with an iodine anion,
It was then dried at 100°C under reduced pressure. 4 g of this iodine-containing anion exchange resin, N,
N'-diphenyl urea 80 mmol, ethanol 120 ml,
In the same manner as in Example 1 using palladium black 1 mgatom, water was distilled off along with a portion of the ethanol, and the reaction was carried out for 1 hour while continuously supplying ethanol corresponding to the distilled amount. As a result, N, N' -The reaction rate of diphenyl urea is 100%, the yield of ethyl N-phenylcarbamate is 99%, the selectivity based on N,N'-diphenyl urea is 99%, and the selectivity based on carbon monoxide is 95%. It was %.
Claims (1)
中から選ばれた少くとも1種と (b) ハロゲンを含む化合物の中から選ばれた少く
とも1種と からなる触媒系の存在下に尿素化合物を一酸化炭
素および有機ヒドロキシル化合物と反応させてウ
レタン化合物を製造する方法において、反応によ
つて生成してくる水の全量又は一部を反応系外に
除去しながら反応させることを特徴とするウレタ
ン化合物の製造法。 2 反応によつて生成してくる水を、反応蒸留
法、一酸化炭素を含む反応用ガスを搬送剤として
除去する方法、有機ヒドロキシル化合物の一部と
共に留去する方法及びこれらを組合わせた方法の
いずれかの方法によつて、反応系外に除去する特
許請求の範囲第1項記載の方法。 3 追加的助触媒として塩基性物質及び/又はキ
レート試薬の中から選ばれた少くとも1種を用い
る特許請求の範囲第1項又は第2項記載の方法。 4 酸化剤が、分子状酸素、有機ニトロ化合物又
はその両方である特許請求の範囲第1項ないし第
3項のいずれかに記載の方法。 5 酸化剤が分子状酸素である特許請求の範囲第
1項ないし第3項のいずれかに記載の方法。 6 白金族金属及び白金族元素を含む化合物が、
パラジウム、ロジウム、パラジウム化合物及びロ
ジウム化合物である特許請求の範囲第1項ないし
第5項のいずれかに記載の方法。 7 ハロゲン化合物が金属ハロゲン化物である特
許請求の範囲第1項ないし第6項のいずれかに記
載の方法。 8 金属ハロゲン化物が、アルカリ金属ハロゲン
化物又はアルカリ土類金属ハロゲン化物である特
許請求の範囲第7項記載の方法。 9 ハロゲン化合物が、ハロゲン化オニウム化合
物又は反応系でこれらを生成することのできる化
合物である特許請求の範囲第1項ないし第6項の
いずれかに記載の方法。 10 ハロゲン化オニウム化合物が、ハロゲン化
アンモニウム化合物、ハロゲン化ホスホニウム化
合物、ハロゲン化アルソニウム化合物又はハロゲ
ン化スルホニウム化合物である特許請求の範囲第
9項記載の方法。 11 ハロゲン化オニウム化合物がハロゲン化オ
ニウムグループを主鎖又は側鎖に含むポリマーで
ある特許請求の範囲第9項又は第10項記載の方
法。 12 ハロゲン化合物が、ハロゲンのオキソ酸又
はその塩である特許請求の範囲第1項ないし第6
項のいずれかに記載の方法。 13 ハロゲン化合物が、ハロゲンを含む錯化合
物である特許請求の範囲第1項ないし第6項のい
ずれかに記載の方法。 14 ハロゲン化合物が、有機ハロゲン化物であ
る特許請求の範囲第1項ないし第6項のいずれか
に記載の方法。 15 ハロゲン種が臭素及び/またはヨウ素であ
る特許請求の範囲第1項ないし第14項のいずれ
かに記載の方法。 16 ハロゲン種が、ヨウ素である特許請求の範
囲第1項ないし第14項のいずれかに記載の方
法。 17 尿素化合物が、N,N′−ジアリール尿素
である特許請求の範囲第1項ないし第16項記載
の方法。 18 N,N′−ジアリール尿素が、N,N′−ジ
フエニル尿素である特許請求の範囲第17項記載
の方法。[Scope of Claims] 1. An oxidizing agent; (a) at least one compound selected from platinum group metals and compounds containing platinum group elements; and (b) at least one compound selected from halogen-containing compounds. In a method for producing a urethane compound by reacting a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system consisting of seeds, all or part of the water produced by the reaction is removed from the reaction system. A method for producing a urethane compound, which comprises reacting while removing the urethane compound. 2. Reactive distillation method, method of removing reaction gas containing carbon monoxide as a carrier agent, method of distilling off the water produced by the reaction together with a part of the organic hydroxyl compound, and a method of combining these methods. The method according to claim 1, wherein the method is removed from the reaction system by any one of the following methods. 3. The method according to claim 1 or 2, in which at least one selected from basic substances and/or chelating reagents is used as an additional promoter. 4. The method according to any one of claims 1 to 3, wherein the oxidizing agent is molecular oxygen, an organic nitro compound, or both. 5. The method according to any one of claims 1 to 3, wherein the oxidizing agent is molecular oxygen. 6 A platinum group metal and a compound containing a platinum group element,
The method according to any one of claims 1 to 5, which is palladium, rhodium, palladium compounds, and rhodium compounds. 7. The method according to any one of claims 1 to 6, wherein the halogen compound is a metal halide. 8. The method according to claim 7, wherein the metal halide is an alkali metal halide or an alkaline earth metal halide. 9. The method according to any one of claims 1 to 6, wherein the halogen compound is an onium halide compound or a compound capable of producing these in a reaction system. 10. The method according to claim 9, wherein the halogenated onium compound is a halogenated ammonium compound, a halogenated phosphonium compound, a halogenated arsonium compound, or a halogenated sulfonium compound. 11. The method according to claim 9 or 10, wherein the halogenated onium compound is a polymer containing a halogenated onium group in its main chain or side chain. 12 Claims 1 to 6, wherein the halogen compound is a halogen oxoacid or a salt thereof
The method described in any of the paragraphs. 13. The method according to any one of claims 1 to 6, wherein the halogen compound is a complex compound containing a halogen. 14. The method according to any one of claims 1 to 6, wherein the halogen compound is an organic halide. 15. The method according to any one of claims 1 to 14, wherein the halogen species is bromine and/or iodine. 16. The method according to any one of claims 1 to 14, wherein the halogen species is iodine. 17. The method according to claims 1 to 16, wherein the urea compound is N,N'-diarylurea. 18. The method according to claim 17, wherein the 18 N,N'-diarylurea is N,N'-diphenylurea.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP842184A JPS60152456A (en) | 1984-01-23 | 1984-01-23 | Production of urethane compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP842184A JPS60152456A (en) | 1984-01-23 | 1984-01-23 | Production of urethane compound |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60152456A JPS60152456A (en) | 1985-08-10 |
JPH0258258B2 true JPH0258258B2 (en) | 1990-12-07 |
Family
ID=11692657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP842184A Granted JPS60152456A (en) | 1984-01-23 | 1984-01-23 | Production of urethane compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60152456A (en) |
-
1984
- 1984-01-23 JP JP842184A patent/JPS60152456A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS60152456A (en) | 1985-08-10 |
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