CA1118447A - Process for the production of n-alkylarylamines - Google Patents
Process for the production of n-alkylarylaminesInfo
- Publication number
- CA1118447A CA1118447A CA000330851A CA330851A CA1118447A CA 1118447 A CA1118447 A CA 1118447A CA 000330851 A CA000330851 A CA 000330851A CA 330851 A CA330851 A CA 330851A CA 1118447 A CA1118447 A CA 1118447A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- carbon atoms
- moiety
- reaction
- alkanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000008569 process Effects 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 18
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052802 copper Inorganic materials 0.000 claims abstract description 8
- 239000010949 copper Substances 0.000 claims abstract description 8
- 239000007792 gaseous phase Substances 0.000 claims abstract description 4
- 239000004115 Sodium Silicate Substances 0.000 claims abstract 2
- 229910052911 sodium silicate Inorganic materials 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000012159 carrier gas Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 4
- 239000005751 Copper oxide Substances 0.000 claims description 4
- 229910000431 copper oxide Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract description 5
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- -1 alkyl radical Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229940024548 aluminum oxide Drugs 0.000 description 1
- FJPRYKYQVBQRTD-UHFFFAOYSA-N aniline methanol Chemical compound CO.Nc1ccccc1 FJPRYKYQVBQRTD-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus 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
- 150000003839 salts Chemical class 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
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000004992 toluidines Chemical class 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
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- 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
- C07C209/18—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 carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH715778A CH633520A5 (de) | 1978-06-30 | 1978-06-30 | Verfahren zur herstellung von n-alkylarylaminen. |
| CH7157/78 | 1978-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1118447A true CA1118447A (en) | 1982-02-16 |
Family
ID=4320802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000330851A Expired CA1118447A (en) | 1978-06-30 | 1979-06-29 | Process for the production of n-alkylarylamines |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2919741A1 (de) * | 1979-05-16 | 1980-11-27 | Basf Ag | Verfahren zur herstellung von m-substituierten n-methylanilinen |
| DE3686063D1 (de) * | 1985-01-29 | 1992-08-27 | Ciba Geigy Ag | Verfahren zur herstellung von n-alkylanilinen. |
| CN100408179C (zh) * | 2005-05-20 | 2008-08-06 | 中国科学院大连化学物理研究所 | 用于苯胺与醇气相合成n-烷基苯胺的过渡金属催化剂 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732311A (en) * | 1970-02-24 | 1973-05-08 | Fine Organics Inc | Production of n-alkylated amines |
| US3819709A (en) * | 1970-12-09 | 1974-06-25 | New Japan Chem Co Ltd | Synthesis of n-methylaniline |
| DE2324855A1 (de) * | 1973-05-17 | 1974-12-05 | Hoechst Ag | Verfahren zur n-methylierung von aliphatischen aminen |
| DE2335906C3 (de) * | 1973-07-14 | 1978-06-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen Herstellung von N-Alkylarylaminen |
| DE2646379C3 (de) * | 1976-10-14 | 1982-04-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N-Alkylanilinen |
-
1978
- 1978-06-30 CH CH715778A patent/CH633520A5/de not_active IP Right Cessation
-
1979
- 1979-06-08 ZA ZA792863A patent/ZA792863B/xx unknown
- 1979-06-13 IN IN613/CAL/79A patent/IN153564B/en unknown
- 1979-06-18 ES ES481637A patent/ES481637A1/es not_active Expired
- 1979-06-21 JP JP7865079A patent/JPS559063A/ja active Pending
- 1979-06-22 DE DE7979102070T patent/DE2960991D1/de not_active Expired
- 1979-06-22 EP EP79102070A patent/EP0006590B1/de not_active Expired
- 1979-06-22 AT AT79102070T patent/ATE288T1/de active
- 1979-06-22 IL IL57631A patent/IL57631A/xx unknown
- 1979-06-26 DD DD213900A patent/DD146178A5/de unknown
- 1979-06-28 PL PL1979216679A patent/PL116521B1/pl unknown
- 1979-06-28 CS CS794489A patent/CS208783B2/cs unknown
- 1979-06-28 SU SU792784304A patent/SU955856A3/ru active
- 1979-06-28 HU HU79LO433A patent/HU180833B/hu unknown
- 1979-06-29 CA CA000330851A patent/CA1118447A/en not_active Expired
- 1979-06-30 KR KR7902163A patent/KR810001701B1/ko not_active Expired
- 1979-06-30 RO RO7998006A patent/RO77273A/ro unknown
- 1979-07-29 BR BR7904142A patent/BR7904142A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0006590A1 (de) | 1980-01-09 |
| ZA792863B (en) | 1980-06-25 |
| JPS559063A (en) | 1980-01-22 |
| CS208783B2 (en) | 1981-09-15 |
| PL116521B1 (en) | 1981-06-30 |
| KR810001701B1 (ko) | 1981-10-27 |
| ES481637A1 (es) | 1980-06-16 |
| BR7904142A (pt) | 1980-03-25 |
| RO77273A (ro) | 1981-08-17 |
| IN153564B (enrdf_load_stackoverflow) | 1984-07-28 |
| CH633520A5 (de) | 1982-12-15 |
| IL57631A (en) | 1983-02-23 |
| IL57631A0 (en) | 1979-10-31 |
| EP0006590B1 (de) | 1981-10-14 |
| DE2960991D1 (en) | 1981-12-24 |
| ATE288T1 (de) | 1981-10-15 |
| PL216679A1 (enrdf_load_stackoverflow) | 1980-02-25 |
| HU180833B (en) | 1983-04-29 |
| DD146178A5 (de) | 1981-01-28 |
| SU955856A3 (ru) | 1982-08-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4122118A (en) | Copper-N-methylpyrrolidone catalyst useful in the production of nitrodiphenyl amines | |
| US8952155B2 (en) | Rilpivirine process | |
| AU2002315530B2 (en) | Process for preparing 4-aminodiphenylamine | |
| AU2002315530A1 (en) | Process for preparing 4-aminodiphenylamine | |
| US3231601A (en) | Process for the cyanoethylation of aromatic amines | |
| CA1118447A (en) | Process for the production of n-alkylarylamines | |
| CA2675685A1 (en) | Process for preparing 4-aminodiphenylamines | |
| IE46944B1 (en) | Denitrosation of organic nitrosamines | |
| US3496213A (en) | Mono-cyanoethylation of aromatic amines with an aqueous zinc chloride catalyst | |
| US4642344A (en) | Polyamines | |
| CA2028047A1 (en) | Process for preparing quaternary ammonium compounds | |
| JP4142861B2 (ja) | 環状脂肪族の第１級ビシナルジアミンのシアノエチル化 | |
| JP2531519B2 (ja) | オキサミド誘導体の製法 | |
| US2537834A (en) | Substituted guanylmelamines | |
| US3393241A (en) | Preparation of nitrodiarylamines | |
| KR910004664B1 (ko) | 할로겐화된 아닐린류의 제조방법 | |
| US3366686A (en) | Process for preparing primary amines | |
| US3941844A (en) | Continuous manufacture of N-alkylated arylamines | |
| US3278603A (en) | Process for preparing aromatic amines | |
| JPH0138779B2 (enrdf_load_stackoverflow) | ||
| US4268458A (en) | Process for the preparation of N-alkylated aromatic amines | |
| US4463192A (en) | Process for the reduction of an N-hydrocarbyl substituted oxazolidine with carbon monoxide to form the corresponding N-hydrocarbyl substituted alkanolamine | |
| US4366321A (en) | Preparation of 2-halo-3-nitro-5-acyl thiophenes and intermediate compounds | |
| JPS647981B2 (enrdf_load_stackoverflow) | ||
| JPH0358960A (ja) | Ｎ―アルキル化アニリンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |