JP7394630B2 - ジアンモニウム塩及びその用途 - Google Patents
ジアンモニウム塩及びその用途 Download PDFInfo
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- JP7394630B2 JP7394630B2 JP2020003384A JP2020003384A JP7394630B2 JP 7394630 B2 JP7394630 B2 JP 7394630B2 JP 2020003384 A JP2020003384 A JP 2020003384A JP 2020003384 A JP2020003384 A JP 2020003384A JP 7394630 B2 JP7394630 B2 JP 7394630B2
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- carbon atoms
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- zeolite
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- 150000003839 salts Chemical class 0.000 title claims description 70
- -1 halide ion Chemical class 0.000 claims description 467
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 105
- 239000010457 zeolite Substances 0.000 claims description 101
- 229910021536 Zeolite Inorganic materials 0.000 claims description 94
- 238000004519 manufacturing process Methods 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 52
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000000377 silicon dioxide Substances 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 12
- 229940006460 bromide ion Drugs 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 7
- 229940006461 iodide ion Drugs 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 184
- 125000000217 alkyl group Chemical group 0.000 description 48
- 239000002904 solvent Substances 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000002994 raw material Substances 0.000 description 32
- 150000003335 secondary amines Chemical class 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000003545 alkoxy group Chemical group 0.000 description 25
- JIWBIWFOSCKQMA-LTKCOYKYSA-N all-cis-octadeca-6,9,12,15-tetraenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O JIWBIWFOSCKQMA-LTKCOYKYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000000034 method Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 125000004663 dialkyl amino group Chemical group 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 125000004104 aryloxy group Chemical group 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 229910004298 SiO 2 Inorganic materials 0.000 description 17
- 229920001429 chelating resin Polymers 0.000 description 17
- 239000013078 crystal Substances 0.000 description 17
- 125000004986 diarylamino group Chemical group 0.000 description 17
- 239000002168 alkylating agent Substances 0.000 description 16
- 229940100198 alkylating agent Drugs 0.000 description 16
- 238000005342 ion exchange Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 125000003709 fluoroalkyl group Chemical group 0.000 description 14
- 239000012043 crude product Substances 0.000 description 13
- 150000004985 diamines Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 229910000323 aluminium silicate Inorganic materials 0.000 description 11
- 239000003957 anion exchange resin Substances 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 229910052723 transition metal Inorganic materials 0.000 description 11
- 150000003624 transition metals Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 150000007824 aliphatic compounds Chemical class 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000002955 isolation Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- QTFZPDIRXUVRDM-UHFFFAOYSA-N CS(OCC1C(COS(C)(=O)=O)CC(COS(C)(=O)=O)C(COS(C)(=O)=O)C1)(=O)=O Chemical compound CS(OCC1C(COS(C)(=O)=O)CC(COS(C)(=O)=O)C(COS(C)(=O)=O)C1)(=O)=O QTFZPDIRXUVRDM-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229910052681 coesite Inorganic materials 0.000 description 6
- 229910052906 cristobalite Inorganic materials 0.000 description 6
- 239000004210 ether based solvent Substances 0.000 description 6
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 235000012239 silicon dioxide Nutrition 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 229910052682 stishovite Inorganic materials 0.000 description 6
- 229910052905 tridymite Inorganic materials 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 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 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 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 5
- 238000004255 ion exchange chromatography Methods 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 4
- 125000005916 2-methylpentyl group Chemical group 0.000 description 4
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000005456 alcohol based solvent Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 229910017053 inorganic salt Inorganic materials 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KRVFDQLWSXYEOD-UHFFFAOYSA-N tetraethyl cyclohexane-1,2,4,5-tetracarboxylate Chemical compound CCOC(=O)C1CC(C(=O)OCC)C(C(=O)OCC)CC1C(=O)OCC KRVFDQLWSXYEOD-UHFFFAOYSA-N 0.000 description 4
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 description 3
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 229910000071 diazene Inorganic materials 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- 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 3
- 238000010335 hydrothermal treatment Methods 0.000 description 3
- 150000002500 ions Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000004337 3-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluenecarboxylic acid Natural products CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000008584 quinuclidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
Description
[1] 一般式(1)で表されるジアンモニウム塩。
R1、R2、R3及びR4は、各々独立に、炭素数1から10のアルキル基、炭素数1から10のハロアルキル基又は炭素数6から10の芳香族炭化水素基を表し、これらの置換基は、水酸基、炭素数1から6のアルキル基、炭素数6から10のアリール基、炭素数1から6のアルコキシ基、炭素数6から10のアリールオキシ基、炭素数2から12のジアルキルアミノ基、炭素数6から10のモノアリールアミノ基及び炭素数12から20のジアリールアミノ基からなる群から選択される1つ以上の置換基で置換されていてもよい。
[2] Y-が、塩化物イオン、臭化物イオン、ヨウ化物イオン、ベンゼンスルホン酸イオン、p-トルエンスルホン酸イオン、メタンスルホン酸イオン、トリフルオロメタンスルホン酸イオン又はOH-(水酸化物イオン)である[1]に記載のジアンモニウム塩。
[3] R1、R2、R3及びR4が、各々独立に、炭素数1から10のアルキル基又は炭素数6から10の芳香族炭化水素基を表し、これらの置換基は、炭素数1から6のアルキル基、炭素数6から10のアリールオキシ基、炭素数2から12のジアルキルアミノ基、炭素数1から6のアルコキシ基及び炭素数12から20のジアリールアミノ基からなる群から選択される1つ以上の置換基で置換されていてもよい、である[1]又は[2]に記載のジアンモニウム塩。
[4] R1、R2、R3及びR4が、各々独立に、炭素数1から6のアルキル基、炭素数6から10のアリールオキシ基、炭素数2から12のジアルキルアミノ基、炭素数1から6のアルコキシ基及び炭素数12から20のジアリールアミノ基からなる群から選択される1つ以上の置換基で置換されていてもよい炭素数1から10のアルキル基である[1]乃至[3]に記載のジアンモニウム塩。
[5] R1、R2、R3及びR4が、各々独立に、炭素数2から4のジアルキルアミノ基及び炭素数1から4のアルコキシ基からなる群から選択される1つ以上の置換基で置換されていてもよい炭素数1から6のアルキル基である[1]乃至[4]に記載のジアンモニウム塩。
[6] R1とR2とが同一、且つR3とR4とが同一の置換基である[1]乃至[5]に記載のジアンモニウム塩。
[7] R1とR2が同一且つメチル基又はエチル基であり、R3とR4とが同一且つメチル基又はエチル基であり、Y-が塩化物イオン、臭化物イオン又はOH-(水酸化物イオン)である[1]乃至[6]のいずれか一項に記載のジアンモニウム塩。
[8] [1]に記載の一般式(1)で表されるジアンモニウム塩、シリカ源、アルミナ源、アルカリ源及び水を含む組成物を結晶化させる結晶化工程、を有することを特徴とするゼオライトの製造方法。
[9] ゼオライトが小細孔ゼオライトである、前記[8]に記載のゼオライトの製造方法。
[10] ゼオライトがAFX型ゼオライトである、前記[8]又は[9]に記載のゼオライトの製造方法。
本発明のジアンモニウム塩(1)の製造方法として、下記一般式(2)で表される脂肪族化合物と、下記一般式(3a)で表される第二級アミンと、下記一般式(3b)で表される第二級アミンとを反応させる工程、を含む、一般式(1a)で表されるジアンモニウム塩の製造方法(以下、「製法1」ともいう。)を挙げることができる。
製法1の反応に供する、第二級アミン(3a)及び第二級アミン(3b)は、同一の第二級アミンを用いても良いし、異なる2種類の第二級アミンを用いても良く、異なる2種類の第二級アミンを用いた場合、非対称の本発明のジアンモニウム塩(1a)を得ることができる。
本実施形態のジアンモニウム塩の製造方法の別の実施形態として、下記一般式(4a)で表されるジアミンと、下記一般式(5a)で表されるアルキル化剤と、下記一般式(5b)で表されるアルキル化剤とを反応させる工程、を有することを特徴とする、一般式(1b)で表されるジアンモニウム塩の製造方法(以下、「製法2」ともいう。)が挙げられる。
Yaは、ハロゲン原子又はR5SO2Oで表される有機スルホニルオキシ基を表す。
Yaは、ハロゲン原子又はR5SO2Oで表される有機スルホニルオキシ基を表す。
製法2の反応に供する、アルキル化剤(5a)及びアルキル化剤(5b)は、同一のアルキル化剤を用いても良いし、異なる2種類のアルキル化剤を用いても良く、異なる2種類のアルキル化剤を用いた場合、非対称の本発明のジアンモニウム塩(1b)を得ることができる。
製法2に供するジアミン(4a)の製造方法の実施形態の一例として、一般式(6a)で表されるジイミドと、還元剤とを反応させる工程、を有することを特徴とする、ジアミン(4a)の製造方法(以下、「原料製法1」ともいう。)、を挙げることができる。
好ましくは10以上50以下、
より好ましくは10以上40以下
OH/SiO2 0.06以上1.0以下、
好ましくは0.08以上0.60以下、
より好ましくは0.10以上0.40以下
M/SiO2 0.06以上1.0以下、
好ましくは0.08以上0.60以下、
より好ましくは0.10以上0.40以下
SDA/SiO2 0.01以上2.0以下、
好ましくは0.02以上1.0以下、
より好ましくは0.03以上0.5以下
H2O/SiO2 5以上60以下、
好ましくは10以上45以下、
より好ましくは10以上30以下
種晶 10.0重量%以下、
好ましくは5.0重量%以下、
より好ましくは3.5重量%以下
上記組成において、SiO2/Al2O3は原料組成物中のアルミナに対するシリカのモル比であり、OH/SiO2、M/SiO2、SDA/SiO2及びH2O/SiO2は、それぞれ、原料組成物中のシリカに対する水酸化物イオン、アルカリ金属、SDA又は水のモル比である。なお、Mはアルカリ金属であり、例えば、アルカリ金属がナトリウムである場合、又は、アルカリ金属がナトリウムとカリウムである場合、M/SiO2は、それぞれ、Na/SiO2、又は(Na+K)/SiO2となる。
処理時間 :2時間以上500時間以下
処理圧力 :自生圧
結晶化における原料組成物の状態は任意であり、静置下又は撹拌下のいずれでもよいが、撹拌下であることが好ましい。
(H1-NMR)
AscendTM 400(400MHz、Bruker製)又はUltraShieldTM Plus 400(400MHz、Bruker製)を使用して、試料のH1-NMR測定を行った。測定溶媒として、重クロロホルム(CDCl3)、重ジメチルスルホキシド(DMSO-d6)又は重水(D2O)を、内部標準物質としてテトラメチルシラン(TMS)を用いて試料のH1-NMRを測定した。測定データは、化学シフト、多重度、カップリング定数(Hz)、積分値の順に記載した。
(イオンクロマトグラフ)
イオンクロマトグラフ装置IC-2001(東ソー製)を使用し、陰イオンクロマトグラフを測定した。測定条件は以下のとおりである。
溶離液: 7.5mmol/L炭酸水素ナトリウム水溶液
+1.1mmol/L炭酸ナトリウム水溶基
流速 : 0.8mL/min
温度 : 40℃
検出 : 電気伝導度
(粉末X線回折)
一般的なX線回折装置(装置名:Ultima IV、RIGAKU製)を使用し、試料のXRD測定を行った。測定条件は以下のとおりである。
測定モード : ステップスキャン
スキャン幅 : 0.02°
発散スリット: 1.00deg
散乱スリット: 開放
受光スリット: 開放
計測時間 : 1.0分
測定範囲 : 2θ=3.0°~43.0°
得られたXRDのパターンとIZAのStructure Commissionのホーム-ページに掲載されたXRDパターンとを比較することによって、試料の結晶相及びXRDピーク強度比を確認した。
(ケイ素、アルミニウムの定量)
一般的な誘導結合プラズマ発光分析装置(装置名:OPTIMA3300DV、PERKIN ELMER製)を用いて、試料の組成分析を行った。試料をフッ酸と硝酸の混合溶液に溶解させ、測定溶液を調製した。得られた測定溶液を装置に投入して試料の組成を分析した。得られたケイ素(Si)、アルミニウム(Al)のモル濃度から、SiO2/Al2O3を算出した。
実施例1-1
参考例1-1
(1,2,4,5-テトラキシ(ヒドロキシメチル)シクロヘキサンの合成)
(1,2,4,5-テトラキス(メタンスルホニルオキシメチル)シクロヘキサンの合成)
実施例2-1
実施例1-1で得られた5,5,11,11-テトラエチルトリシクロ[7.3.0.03,7]ドデカン-5,11-ジアザニウム=ジブロミド、48%NaOH及びY型ゼオライト(商品名:HSZ-350HUA、東ソー製)を混合し組成物を得た。得られた組成物の組成を示す。
OH/SiO2 = 0.35
Na/SiO2 = 0.35
SDA/SiO2 = 0.08
H2O/SiO2 = 25
組成物の種晶含有量が3.0重量%となるように、組成物にAFX型ゼオライトを添加した後、十分に撹拌した。
Claims (6)
- 一般式(1)で表されるジアンモニウム塩。
R1、R2、R3及びR4は、各々独立に、メチル基、エチル基、プロピル基、又はイソプロピル基、を表し、これらの置換基は、水酸基で置換されていてもよい。
Y-は、同一又は相異なって、ハロゲン化物イオン、R5SO2O-で表されるスルホン酸イオン、R6COO-で表されるカルボン酸イオン又はOH-(水酸化物イオン)を表す。
R5は、メチル基、エチル基、プロピル基、又はイソプロピル基を表す。
R6は、メチル基、エチル基、プロピル基、又はイソプロピル基を表す。] - Y-が、塩化物イオン、臭化物イオン、ヨウ化物イオン又はOH-(水酸化物イオン)である請求項1に記載のジアンモニウム塩。
- R1とR2とが同一、且つR3とR4とが同一の置換基である請求項1又は2に記載のジアンモニウム塩。
- R1とR2が同一且つメチル基又はエチル基であり、R3とR4とが同一且つメチル基又はエチル基であり、Y-が塩化物イオン、臭化物イオン又はOH-(水酸化物イオン)である請求項1乃至3のいずれか一項に記載のジアンモニウム塩。
- 請求項1に記載の一般式(1)で表されるジアンモニウム塩、シリカ源、アルミナ源、アルカリ源及び水を含む組成物を結晶化させる結晶化工程、を有することを特徴とするゼオライトの製造方法。
- ゼオライトがAFX型ゼオライトである、前記請求項5に記載のゼオライトの製造方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016169139A (ja) | 2015-03-16 | 2016-09-23 | 国立大学法人横浜国立大学 | Afx型ゼオライトの製法 |
JP2017197398A (ja) | 2016-04-26 | 2017-11-02 | ユニゼオ株式会社 | Mse型ゼオライトの製造方法 |
WO2020241202A1 (ja) | 2019-05-27 | 2020-12-03 | 国立大学法人大阪大学 | 化合物及びその製造方法、afx型ゼオライト及びその製造方法、並びにハニカム積層触媒 |
JP2021031459A (ja) | 2019-08-27 | 2021-03-01 | 東ソー株式会社 | ヘキサヒドロベンゾジピロール及びその製造方法 |
JP7249911B2 (ja) | 2019-08-27 | 2023-03-31 | 東ソー株式会社 | ヘキサヒドロベンゾジピロリウム塩及びその用途 |
-
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016169139A (ja) | 2015-03-16 | 2016-09-23 | 国立大学法人横浜国立大学 | Afx型ゼオライトの製法 |
JP2017197398A (ja) | 2016-04-26 | 2017-11-02 | ユニゼオ株式会社 | Mse型ゼオライトの製造方法 |
WO2020241202A1 (ja) | 2019-05-27 | 2020-12-03 | 国立大学法人大阪大学 | 化合物及びその製造方法、afx型ゼオライト及びその製造方法、並びにハニカム積層触媒 |
JP2021031459A (ja) | 2019-08-27 | 2021-03-01 | 東ソー株式会社 | ヘキサヒドロベンゾジピロール及びその製造方法 |
JP7249911B2 (ja) | 2019-08-27 | 2023-03-31 | 東ソー株式会社 | ヘキサヒドロベンゾジピロリウム塩及びその用途 |
Non-Patent Citations (1)
Title |
---|
MARTIN,N. et al.,Cage-based small-pore catalysts for NH3-SCR prepared by combining bulky organic structure directing agents with modified zeolites as reagents,Applied Catalysis, B: Environmental,2017年,Vol.217,p.1-36 |
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