JP2017533247A - 直接アミノ化反応によるアミンの形成方法 - Google Patents
直接アミノ化反応によるアミンの形成方法 Download PDFInfo
- Publication number
- JP2017533247A JP2017533247A JP2017525040A JP2017525040A JP2017533247A JP 2017533247 A JP2017533247 A JP 2017533247A JP 2017525040 A JP2017525040 A JP 2017525040A JP 2017525040 A JP2017525040 A JP 2017525040A JP 2017533247 A JP2017533247 A JP 2017533247A
- Authority
- JP
- Japan
- Prior art keywords
- reactant
- palladium
- ammonia
- compound
- catalyst
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- 150000001412 amines Chemical class 0.000 title claims abstract description 28
- 238000005576 amination reaction Methods 0.000 title abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 229910000420 cerium oxide Inorganic materials 0.000 claims abstract description 26
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002941 palladium compounds Chemical class 0.000 claims abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 38
- 239000000376 reactant Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 229910021529 ammonia Inorganic materials 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 10
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005470 impregnation Methods 0.000 claims description 6
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 4
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 4
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 3
- 238000010304 firing Methods 0.000 claims description 3
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
- 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 claims description 3
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005968 1-Decanol Substances 0.000 claims description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 2
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims description 2
- NMRPBPVERJPACX-QMMMGPOBSA-N 3-Octanol Natural products CCCCC[C@@H](O)CC NMRPBPVERJPACX-QMMMGPOBSA-N 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 238000000975 co-precipitation Methods 0.000 claims description 2
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 claims description 2
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 2
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 claims description 2
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 claims description 2
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000003335 secondary amines Chemical class 0.000 abstract description 16
- 150000003512 tertiary amines Chemical class 0.000 abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 8
- 150000001298 alcohols Chemical class 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 230000009467 reduction Effects 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000001354 calcination Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- UNJPQTDTZAKTFK-UHFFFAOYSA-K cerium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Ce+3] UNJPQTDTZAKTFK-UHFFFAOYSA-K 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000007126 N-alkylation reaction Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 2
- DRVWBEJJZZTIGJ-UHFFFAOYSA-N cerium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Ce+3].[Ce+3] DRVWBEJJZZTIGJ-UHFFFAOYSA-N 0.000 description 2
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 hydroamination Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910001848 post-transition metal Inorganic materials 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 101001086426 Homo sapiens Olfactory receptor 1J2 Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229910021193 La 2 O 3 Inorganic materials 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 102100032722 Olfactory receptor 1J2 Human genes 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 208000034699 Vitreous floaters Diseases 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000005913 hydroamination reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N octan-4-ol Chemical compound CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MMKQUGHLEMYQSG-UHFFFAOYSA-N oxygen(2-);praseodymium(3+) Chemical compound [O-2].[O-2].[O-2].[Pr+3].[Pr+3] MMKQUGHLEMYQSG-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910003447 praseodymium oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- VDRDGQXTSLSKKY-UHFFFAOYSA-K ruthenium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Ru+3] VDRDGQXTSLSKKY-UHFFFAOYSA-K 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/63—Platinum group metals with rare earths or actinides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
RHC=O+NH3→RHC=NH+H2O
RHC=NH+H2→R−CH2−NH2
R1−OH+R2R3NH→R1R2R3−N+H2O
(R1=アルキル/R2,R3=H又はアルキル)
1)1つの1級又は2級ヒドロキシル基を含むアルキルアルコールである第1の反応物と、
2)アンモニア及び/又はアンモニア源である第2の反応物と、
を少なくとも反応させることを含む、少なくとも1種のアミンの、特には1級、2級、又は3級アミンの製造方法に関する。
1)式(I)R1−OH又は式(II)R2−C(OH)−R3の化合物である第1の反応物(式中、R1、R2、及びR3は独立に1〜40個の炭素原子を含むアルキル基である)と、
2)アンモニア及び/又はアンモニア源である第2の反応物と、
を少なくとも反応させることを含む、少なくとも1種のアミンの、好ましくは1級、2級、又は3級アミンの製造方法に関する。
特許請求の範囲を含めて、本明細書の全体にわたって、用語「1つを含む」は、特に明記しない限り、用語「少なくとも1つを含む」と同じ意味であると理解されるべきであり、「〜」は、その両端を含むと理解されるべきである。
−場合によっては酸化剤の存在下で、反応媒体のpHが7より大きくなるような塩基の量で、セリウム塩の溶液と塩基とを反応させることにより水酸化セリウムを合成し、得られた析出物を分離し、場合によってはこれを洗浄すること;
−水酸化セリウムを分解性塩基の水性懸濁液又は水溶液に入れること;
−密閉したチャンバーの中で、これを前記媒体の臨界温度及び臨界圧力よりもそれぞれ低いある温度及びある圧力まで加熱すること;
−反応混合物を冷却してこれを周囲圧力にすること;
−この方法で処理した水酸化セリウムを分離すること;その後
−これを焼成すること;
からなる方法に従って特には得ることができる。
R1−NH2 (III)
(R1)2−NH (IV)
(R1)3−N (V)
n−C8H17OH+NH3→n−C8H17NH2+(n−C8H17)2NH+(n−C8H17)3N+C7H15CN
Claims (14)
- 酸化セリウムを含む担体上に少なくともパラジウム化合物が含まれる触媒の存在下、
1)1つの1級又は2級ヒドロキシル基を含むアルキルアルコールである第1の反応物と、
2)アンモニア及び/又はアンモニア源である第2の反応物と、
を少なくとも反応させることを含む、少なくとも1種のアミンの製造方法。 - 触媒の担体が、担体の総重量基準で50〜100重量%の酸化セリウムを含む、請求項1に記載の方法。
- 酸化セリウムが、350℃の温度で2時間焼成後に測定した際に、50〜300m2/gに含まれる比表面積を示す、請求項1又は2に記載の方法。
- パラジウム化合物が、パラジウム金属、PdO、PdO2、硝酸パラジウム、塩化パラジウム、酢酸パラジウム、パラジウムアセチルアセトナート、及び水酸化パラジウムからなる群から選択される、請求項1又は2のいずれか一項に記載の方法。
- 触媒が含浸又は共沈によって得られる、請求項1〜4のいずれか一項に記載の方法。
- 第2の反応物に対する触媒の重量比が0.05〜2に含まれる、請求項1〜5のいずれか一項に記載の方法。
- 第1の反応物が1〜40個の炭素原子を含むアルキル鎖を有する、請求項1〜6のいずれか一項に記載の方法。
- 第1の反応物が、式(I)R1−OH、又は式(II)R2−C(OH)−R3(式中、R1、R2、及びR3は独立に1〜40個の炭素原子を含むアルキル基である)の化合物である、請求項1〜7のいずれか一項に記載の方法。
- 第1の反応物が、式(I)R1−OH、又は式(II)R2−C(OH)−R3(式中、R1、R2、及びR3は独立に4〜20個の炭素原子を含むアルキル基である)の化合物である、請求項1〜7のいずれか一項に記載の方法。
- 第1の反応物が、1−ブタノール、1−ヘキサノール、1−オクタノール、1−デカノール、1−ドデカノール、2−ブタノール、2−ヘキサノール、3−ヘキサノール、2−オクタノール、3−オクタノール、及び4−オクタノールからなる群から選択される、請求項1〜9のいずれか一項に記載の方法。
- 第2の反応物がアンモニアである、請求項1〜10のいずれか一項に記載の方法。
- アンモニアが気体のアンモニア、液体のアンモニア、又は溶媒中のアンモニア溶液である、請求項1〜11のいずれか一項に記載の方法。
- 得られるアミンが、オクチルアミン、ジオクチルアミン、トリオクチルアミン、ブチルアミン、ジブチルアミン、トリブチルアミン、ヘキシルアミン、ジヘキシルアミン、トリヘキシルアミン、デシルアミン、ジデシルアミン、トリデシルアミン、ドデシルアミン、ジドデシルアミン、及びトリドデシルアミンからなる群から選択される、請求項1〜12のいずれか一項に記載の方法。
- 反応媒体が、反応の開始時に、1モル当量の第1の反応物に対して0.1〜50モル当量の第2の反応物を含む、請求項1〜13のいずれか一項に記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2014/090695 WO2016074121A1 (en) | 2014-11-10 | 2014-11-10 | Process for forming amine by direct amination reaction |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017533247A true JP2017533247A (ja) | 2017-11-09 |
JP6450841B2 JP6450841B2 (ja) | 2019-01-09 |
Family
ID=55953530
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017525040A Active JP6450841B2 (ja) | 2014-11-10 | 2014-11-10 | 直接アミノ化反応によるアミンの形成方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10207980B2 (ja) |
EP (1) | EP3218350B1 (ja) |
JP (1) | JP6450841B2 (ja) |
KR (1) | KR20170083085A (ja) |
CN (1) | CN107074735B (ja) |
WO (1) | WO2016074121A1 (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10207980B2 (en) | 2014-11-10 | 2019-02-19 | Rhodia Operations | Process for forming amine by direct amination reaction |
US10167252B2 (en) | 2015-12-22 | 2019-01-01 | Eastman Chemical Company | Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds |
US10160718B2 (en) | 2015-12-22 | 2018-12-25 | Eastman Chemical Company | Methods of making compounds having antidegradant and antifatigue efficacy |
US10428009B2 (en) | 2015-12-22 | 2019-10-01 | Eastman Chemical Company | Methods of making compounds and mixtures having antidegradant and antifatigue efficacy |
US10260017B2 (en) | 2015-12-22 | 2019-04-16 | Eastman Chemical Company | Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including said compounds |
US10287418B2 (en) | 2015-12-22 | 2019-05-14 | Eastman Chemical Company | Compounds with antidegradant and antifatigue efficacy and compositions including said compounds |
WO2018157395A1 (en) * | 2017-03-03 | 2018-09-07 | Rhodia Operations | Process for preparing an amine via a direct amination reaction |
CN107915645A (zh) * | 2017-10-12 | 2018-04-17 | 浙江晋巨化工有限公司 | 一种正丁胺生产方法 |
US10974197B2 (en) * | 2017-11-14 | 2021-04-13 | Hamilton Sundstrand Corporation | Closed-environment air purification system |
EP4114820A4 (en) * | 2020-03-06 | 2024-01-17 | Specialty Operations France | AMINES ALKYLATION PROCESS |
CN114539071B (zh) * | 2022-03-09 | 2024-05-03 | 天津大学 | 一种正己醇胺化反应制正己胺的方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007197422A (ja) * | 2005-12-28 | 2007-08-09 | Kao Corp | 脂含窒素化合物の製造方法 |
JP2011530408A (ja) * | 2008-08-10 | 2011-12-22 | イェダ リサーチ アンド デベロップメント カンパニー リミテッド | アルコールおよびアンモニアからアミンを調製する方法 |
JP2013538816A (ja) * | 2010-09-10 | 2013-10-17 | エボニック デグサ ゲーエムベーハー | 第二級アミンをアンモニアで直接にアミノ化して第一級アミンにする方法 |
JP2014019652A (ja) * | 2012-07-13 | 2014-02-03 | Sumitomo Chemical Co Ltd | 1級アミンの製造方法 |
JP2014505029A (ja) * | 2010-12-08 | 2014-02-27 | エボニック デグサ ゲーエムベーハー | 気相に対する液相の高い体積比及び/又は高い圧力での、均一触媒を用いた、第一級アミンを得るための、アンモニアによる第一級アルコールの高選択的な直接アミノ化法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4209424A (en) | 1977-12-12 | 1980-06-24 | Societe Chimique de la Grande Paroisse, Azote et Products Chimiques | Catalyst for manufacturing amines from alcohols |
DE3045719A1 (de) * | 1980-12-04 | 1982-07-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von cycloaliphatischen und/oder aromatischen aminen |
FR2617154B1 (fr) | 1987-06-29 | 1990-11-30 | Rhone Poulenc Chimie | Procede d'obtention d'oxyde cerique et oxyde cerique a nouvelles caracteristiques morphologiques |
DE3883724T2 (de) * | 1987-12-11 | 1994-04-28 | Showa Denko Kk | Verfahren zur Herstellung von Aminen vom Allyltyp. |
FR2640954B1 (ja) | 1988-12-23 | 1991-03-29 | Rhone Poulenc Chimie | |
JP4989889B2 (ja) | 2005-12-28 | 2012-08-01 | 花王株式会社 | 含窒素化合物の製造方法 |
JP5755237B2 (ja) | 2009-12-03 | 2015-07-29 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 触媒及びアミンの製造方法 |
KR101208895B1 (ko) | 2010-07-02 | 2012-12-06 | 주식회사 케이씨아이 | 액상 촉매를 이용한 장쇄 지방족 삼차 아민의 제조방법 |
CN102503836A (zh) * | 2011-10-11 | 2012-06-20 | 浙江新化化工股份有限公司 | 一种二苄胺的制备方法 |
EP2935201A4 (en) * | 2012-12-21 | 2016-08-03 | Rhodia Operations | PROCESS FOR FORMATION OF PRIMARY, SECONDARY OR TERTIARY AMINE BY DIRECT AMINATION REACTION |
US9663446B2 (en) | 2013-10-15 | 2017-05-30 | Rhodia Operations | Process for forming a primary, a secondary or a tertiary amine via a direct amination reaction |
CN103599776A (zh) * | 2013-11-21 | 2014-02-26 | 福州大学 | 一种Pd/CeO2可见光光催化剂及其制备方法和应用 |
US10207980B2 (en) | 2014-11-10 | 2019-02-19 | Rhodia Operations | Process for forming amine by direct amination reaction |
-
2014
- 2014-11-10 US US15/525,632 patent/US10207980B2/en active Active
- 2014-11-10 CN CN201480083313.6A patent/CN107074735B/zh active Active
- 2014-11-10 EP EP14906052.7A patent/EP3218350B1/en active Active
- 2014-11-10 WO PCT/CN2014/090695 patent/WO2016074121A1/en active Application Filing
- 2014-11-10 JP JP2017525040A patent/JP6450841B2/ja active Active
- 2014-11-10 KR KR1020177015455A patent/KR20170083085A/ko active IP Right Grant
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007197422A (ja) * | 2005-12-28 | 2007-08-09 | Kao Corp | 脂含窒素化合物の製造方法 |
JP2011530408A (ja) * | 2008-08-10 | 2011-12-22 | イェダ リサーチ アンド デベロップメント カンパニー リミテッド | アルコールおよびアンモニアからアミンを調製する方法 |
JP2013538816A (ja) * | 2010-09-10 | 2013-10-17 | エボニック デグサ ゲーエムベーハー | 第二級アミンをアンモニアで直接にアミノ化して第一級アミンにする方法 |
JP2014505029A (ja) * | 2010-12-08 | 2014-02-27 | エボニック デグサ ゲーエムベーハー | 気相に対する液相の高い体積比及び/又は高い圧力での、均一触媒を用いた、第一級アミンを得るための、アンモニアによる第一級アルコールの高選択的な直接アミノ化法 |
JP2014019652A (ja) * | 2012-07-13 | 2014-02-03 | Sumitomo Chemical Co Ltd | 1級アミンの製造方法 |
Non-Patent Citations (1)
Title |
---|
KEN-ICHI SHIMIZU ET AL., ACS CATAL., vol. Vol.3, JPN6018026714, 2013, pages 112 - 117 * |
Also Published As
Publication number | Publication date |
---|---|
KR20170083085A (ko) | 2017-07-17 |
EP3218350A4 (en) | 2018-07-11 |
CN107074735A (zh) | 2017-08-18 |
US10207980B2 (en) | 2019-02-19 |
WO2016074121A1 (en) | 2016-05-19 |
US20170320811A1 (en) | 2017-11-09 |
EP3218350B1 (en) | 2022-01-05 |
CN107074735B (zh) | 2020-04-03 |
JP6450841B2 (ja) | 2019-01-09 |
EP3218350A1 (en) | 2017-09-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6450841B2 (ja) | 直接アミノ化反応によるアミンの形成方法 | |
Furukawa et al. | Highly efficient aerobic oxidation of various amines using Pd 3 Pb intermetallic compounds as catalysts | |
US8187997B2 (en) | Low metal loaded, catalyst compositions including acidic mixed metal oxide as support | |
US5002922A (en) | Catalyst for the amination of alcohols under hydrogenating conditions | |
US9663446B2 (en) | Process for forming a primary, a secondary or a tertiary amine via a direct amination reaction | |
US20100137642A1 (en) | Low metal loaded, alumina supported, catalyst compositions and amination process | |
EA021623B1 (ru) | Катализатор на носителе и способ получения амина | |
KR100216935B1 (ko) | 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법 | |
JP6049757B2 (ja) | 液相中での第二級アミンの製造法 | |
WO2008018148A1 (fr) | Procédé servant à produire un composé aminé | |
US8642811B2 (en) | Preparation of primary diamines having a linear main chain for polyamide syntheses | |
CA2051476A1 (en) | Process for producing an ethylenamine | |
KR20120103323A (ko) | 알코올의 환원성 아민화에 의한 알킬아민 제조용 촉매 | |
US5600000A (en) | Reductive amination processes for the selective production of amino-ethylethanolamine | |
JP5076329B2 (ja) | 酸化オレフィンの製造法 | |
Imamura et al. | Selective hydrogenation of benzene to cyclohexadiene and cyclohexene by lanthanide precipitates obtained from Eu or Yb metal solutions in liquid ammonia | |
Yamaguchi et al. | Supported Metal Hydroxides as Efficient Heterogeneous Catalysts for Green Functional Group Transformations | |
JP4359447B2 (ja) | モノヒドロキシアセトンの製造方法 | |
JP2008044930A (ja) | アミノ化合物の製造方法 | |
JP2015519349A (ja) | モノ−n−アルキル−ピペラジンの製造方法 | |
Wang et al. | Environmentally benign and effective syntheses of N-substituted carbamates via alcoholysis of disubstituted ureas over TiO2/SiO2 catalyst | |
WO2006090754A1 (ja) | 酸化オレフィンの製造法 | |
JP5803619B2 (ja) | ピペラジン類の製造方法 | |
JP5803620B2 (ja) | ピペラジン類の製造法 | |
CN114746179A (zh) | 在铜催化剂上制备胺的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20171010 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180717 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180713 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181011 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20181113 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20181210 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6450841 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |