JPS58116465A - α−ピコリンの製法 - Google Patents

α−ピコリンの製法

Info

Publication number: JPS58116465A
Authority: JP; Japan
Prior art keywords: zeolite; picoline; aniline; silica; ammonia
Prior art date: 1981-12-01
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

Application number

JP57208748A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6348267B2 (de

Inventor

クラレンス・デイトン・チヤング

パトリツク・ダンフオ−ド・パ−キンス

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mobil Oil AS

Original Assignee

Mobil Oil AS

Priority date (The priority date 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 date listed.)

1981-12-01

Filing date

1982-11-30

Publication date

1983-07-11

1982-11-30 Application filed by Mobil Oil AS filed Critical Mobil Oil AS

1983-07-11 Publication of JPS58116465A publication Critical patent/JPS58116465A/ja

1988-09-28 Publication of JPS6348267B2 publication Critical patent/JPS6348267B2/ja

Status Granted legal-status Critical Current

Links

BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 title claims description 95
238000004519 manufacturing process Methods 0.000 title claims description 22
239000010457 zeolite Substances 0.000 claims description 81
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 77
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 62
229910021536 Zeolite Inorganic materials 0.000 claims description 61
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 58
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 46
239000003054 catalyst Substances 0.000 claims description 30
229910021529 ammonia Inorganic materials 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 27
239000000377 silicon dioxide Substances 0.000 claims description 23
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
150000002989 phenols Chemical class 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
150000001412 amines Chemical class 0.000 claims description 10
150000001448 anilines Chemical class 0.000 claims description 10
238000004821 distillation Methods 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 description 23
239000000047 product Substances 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 11
239000013078 crystal Substances 0.000 description 9
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
238000001354 calcination Methods 0.000 description 5
239000011159 matrix material Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
150000004992 toluidines Chemical class 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
238000000605 extraction Methods 0.000 description 4
238000010304 firing Methods 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
229910000831 Steel Inorganic materials 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000499 gel Substances 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
-1 nitrogen-containing aromatic compounds Chemical class 0.000 description 3
150000002892 organic cations Chemical class 0.000 description 3
239000011148 porous material Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000010025 steaming Methods 0.000 description 3
239000010959 steel Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-methylquinoline Chemical compound C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000012159 carrier gas Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000000571 coke Substances 0.000 description 2
239000002131 composite material Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000005336 cracking Methods 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
238000000691 measurement method Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
NHFQUMYGFXFXEK-UHFFFAOYSA-N 2-methylpyridine;4-methylpyridine Chemical compound CC1=CC=NC=C1.CC1=CC=CC=N1 NHFQUMYGFXFXEK-UHFFFAOYSA-N 0.000 description 1
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001292396 Cirrhitidae Species 0.000 description 1
244000241257 Cucumis melo Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
238000004176 ammonification Methods 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
229910052789 astatine Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
125000000753 cycloalkyl group Chemical group 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
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
239000012013 faujasite Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group 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
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000005204 hydroxybenzenes Chemical class 0.000 description 1
239000003317 industrial substance Substances 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229910052680 mordenite Inorganic materials 0.000 description 1
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
238000002411 thermogravimetry Methods 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1

Landscapes

Indole Compounds (AREA)
Catalysts (AREA)
Pyridine Compounds (AREA)

JP57208748A 1981-12-01 1982-11-30 α−ピコリンの製法 Granted JPS58116465A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US32625881A	1981-12-01	1981-12-01
US326258		1981-12-01
US369296		1989-06-21

Publications (2)

Publication Number	Publication Date
JPS58116465A true JPS58116465A (ja)	1983-07-11
JPS6348267B2 JPS6348267B2 (de)	1988-09-28

Family

ID=23271469

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57208748A Granted JPS58116465A (ja)	1981-12-01	1982-11-30	α−ピコリンの製法

Country Status (1)

Country	Link
JP (1)	JPS58116465A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2024541230A (ja) *	2021-10-31	2024-11-08	中国石油化工股▲ふん▼有限公司	アニリンから２－メチルピリジン及びジフェニルアミンを選択的かつ連続的に生産する方法

1982
- 1982-11-30 JP JP57208748A patent/JPS58116465A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2024541230A (ja) *	2021-10-31	2024-11-08	中国石油化工股▲ふん▼有限公司	アニリンから２－メチルピリジン及びジフェニルアミンを選択的かつ連続的に生産する方法

Also Published As

Publication number	Publication date
JPS6348267B2 (de)	1988-09-28

Publication	Publication Date	Title
CA1120455A (en)	1982-03-23	Method for producing aluminosilicates, their use as a catalysts and supports and method for producing catalysts therefrom
EP0002899A1 (de)	1979-07-11	Verfahren zur Herstellung von Aluminosilikaten und deren Verwendung als Katalysatorträger und Katalysatoren
DE68902286T2 (de)	1992-12-10	Chemisches verfahren und katalysator dafuer.
WO2013010662A1 (en)	2013-01-24	Catalyst for the preparation of aromatic hydrocarbons and use thereof
CN115108925A (zh)	2022-09-27	一种硫酸沙丁胺醇杂质及其制备方法
JPS5869846A (ja)	1983-04-26	メチルアミンの製法
US3903079A (en)	1975-09-02	Production of polymethylenimines by cycloammonolysis
RU2127726C1 (ru)	1999-03-20	Способ получения 3-метилпиперидина и 3-метилпиридина
US3976697A (en)	1976-08-24	Preparation of tertiary amines
EP0062542B1 (de)	1985-07-10	Verfahren für die Synthese von Anilin
EP0082613B1 (de)	1986-01-15	Verfahren zur Herstellung von alpha-Picolin
JPS62155242A (ja)	1987-07-10	ビス（ｐ−アミノクミル）ベンゼン類の製造方法
EP0542039B1 (de)	1996-06-26	Verfahren zur Herstellung von Aminen durch reduktive Aminierung
US4388461A (en)	1983-06-14	Process for producing alpha-picoline
Inagaki et al.	1975	Reactions of 2, 4, 6-Tri-t-butylnitrosobenzene with Grignard Reagents
EP0156421A1 (de)	1985-10-02	Verfahren zur Herstellung von Cyanamid
US5488165A (en)	1996-01-30	Process for the production of methyl amines
WO2000031018A1 (en)	2000-06-02	Process for preparing methylamines using acidic molecular sieve catalysts
JPS6348267B2 (de)	1988-09-28
RU2071475C1 (ru)	1997-01-10	Способ получения триэтилендиамина
Pellacani et al.	1982	Degradation of aminimides obtained from enamines and (ethoxycarbonyl) nitrene
JP3443583B2 (ja)	2003-09-02	シス−２，６−ジメチルピペラジンの製造方法
SU1321722A1 (ru)	1987-07-07	Способ получени ацетонитрила
JPS593464B2 (ja)	1984-01-24	アルキル−又はシクロアルケノ−フエノ−ルを、酸触媒の存在下に過剰のアンモニアで気相アミノ化することによつて、アルキル−又はシクロアルケノ−アニリンを製造する方法
JP4505911B2 (ja)	2010-07-21	ジアリールアミンの製造方法

JPS58116465A - α−ピコリンの製法 - Google Patents

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