CS208783B2 - Method of making the n-alkylarylamines - Google Patents
Method of making the n-alkylarylamines Download PDFInfo
- Publication number
- CS208783B2 CS208783B2 CS794489A CS448979A CS208783B2 CS 208783 B2 CS208783 B2 CS 208783B2 CS 794489 A CS794489 A CS 794489A CS 448979 A CS448979 A CS 448979A CS 208783 B2 CS208783 B2 CS 208783B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carbon atoms
- radical
- hydrogen atom
- alkyl radical
- catalyst
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 239000010949 copper Substances 0.000 claims abstract description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052802 copper Inorganic materials 0.000 claims abstract description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 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 3
- 229910000431 copper oxide Inorganic materials 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000007792 gaseous phase Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- -1 C1-C4 alkyl radical Chemical class 0.000 description 7
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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 class 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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 class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 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
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- TUONOWHEGIZLGU-UHFFFAOYSA-N 2,3-dimethylaniline;methanol Chemical compound OC.CC1=CC=CC(N)=C1C TUONOWHEGIZLGU-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DYAIRFBFUGCEEE-UHFFFAOYSA-N aniline methanol Chemical compound OC.OC.NC1=CC=CC=C1 DYAIRFBFUGCEEE-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001875 compounds Chemical class 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
- 239000010410 layer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003839 salts 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH715778A CH633520A5 (de) | 1978-06-30 | 1978-06-30 | Verfahren zur herstellung von n-alkylarylaminen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208783B2 true CS208783B2 (en) | 1981-09-15 |
Family
ID=4320802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS794489A CS208783B2 (en) | 1978-06-30 | 1979-06-28 | Method of making the 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 |
| EP0190101B1 (de) * | 1985-01-29 | 1992-07-22 | 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 EP EP79102070A patent/EP0006590B1/de not_active Expired
- 1979-06-22 IL IL57631A patent/IL57631A/xx unknown
- 1979-06-22 DE DE7979102070T patent/DE2960991D1/de not_active Expired
- 1979-06-22 AT AT79102070T patent/ATE288T1/de active
- 1979-06-26 DD DD213900A patent/DD146178A5/de unknown
- 1979-06-28 HU HU79LO433A patent/HU180833B/hu unknown
- 1979-06-28 CS CS794489A patent/CS208783B2/cs unknown
- 1979-06-28 SU SU792784304A patent/SU955856A3/ru active
- 1979-06-28 PL PL1979216679A patent/PL116521B1/pl unknown
- 1979-06-29 CA CA000330851A patent/CA1118447A/en not_active Expired
- 1979-06-30 RO RO7998006A patent/RO77273A/ro unknown
- 1979-06-30 KR KR7902163A patent/KR810001701B1/ko not_active Expired
- 1979-07-29 BR BR7904142A patent/BR7904142A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU180833B (en) | 1983-04-29 |
| DD146178A5 (de) | 1981-01-28 |
| CH633520A5 (de) | 1982-12-15 |
| EP0006590A1 (de) | 1980-01-09 |
| ES481637A1 (es) | 1980-06-16 |
| CA1118447A (en) | 1982-02-16 |
| PL116521B1 (en) | 1981-06-30 |
| SU955856A3 (ru) | 1982-08-30 |
| DE2960991D1 (en) | 1981-12-24 |
| IN153564B (enrdf_load_stackoverflow) | 1984-07-28 |
| IL57631A0 (en) | 1979-10-31 |
| IL57631A (en) | 1983-02-23 |
| PL216679A1 (enrdf_load_stackoverflow) | 1980-02-25 |
| EP0006590B1 (de) | 1981-10-14 |
| JPS559063A (en) | 1980-01-22 |
| BR7904142A (pt) | 1980-03-25 |
| KR810001701B1 (ko) | 1981-10-27 |
| RO77273A (ro) | 1981-08-17 |
| ATE288T1 (de) | 1981-10-15 |
| ZA792863B (en) | 1980-06-25 |
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