GB814631A - The production of cyano benzylamines - Google Patents
The production of cyano benzylaminesInfo
- Publication number
- GB814631A GB814631A GB93457A GB93457A GB814631A GB 814631 A GB814631 A GB 814631A GB 93457 A GB93457 A GB 93457A GB 93457 A GB93457 A GB 93457A GB 814631 A GB814631 A GB 814631A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyanobenzylamine
- reaction
- ammonia
- dinitrile
- terephthalonitrile
- 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
- QIRSDXBXWUTMRE-UHFFFAOYSA-N benzylcyanamide Chemical class N#CNCC1=CC=CC=C1 QIRSDXBXWUTMRE-UHFFFAOYSA-N 0.000 title abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- LFIWXXXFJFOECP-UHFFFAOYSA-N 4-(aminomethyl)benzonitrile Chemical compound NCC1=CC=C(C#N)C=C1 LFIWXXXFJFOECP-UHFFFAOYSA-N 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M Perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N Perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000004677 hydrates Chemical class 0.000 abstract 2
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- XFKPORAVEUOIRF-UHFFFAOYSA-N 3-(aminomethyl)benzonitrile Chemical compound NCC1=CC=CC(C#N)=C1 XFKPORAVEUOIRF-UHFFFAOYSA-N 0.000 abstract 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N Cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N Phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 238000000151 deposition Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000005755 formation reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cyanobenzylamines are prepared by the hydrogenation of phthalonitrile, isophthalonitrile, and/or terephthalonitrile in the liquid phase in the presence of a palladium or platinum catalyst. The catalysts are preferably deposited on a support such as alumina or carbon. A preferred catalyst is made by depositing 0.1 to 5 parts of palladium on to 99.9-95 parts of powdered alumina. The amount of catalyst used is preferably from 0.005 and 5 per cent by weight of the dinitrile solution. A solvent such as ammonia, toluene or isopropylbenzene, which may be diluted with e.g. ethanol may be used. Suitable amounts of ammonia are up to twenty times the weight of dinitrile, and the ammonia may be used together with e.g. toluene. The reaction may take place between 0 DEG and 150 DEG C. at atmospheric to 100 atmospheres pressure. When temperatures above about 60 DEG C. are used the reaction should be stopped when sufficient hydrogen has been taken up to form the mono-amine. The cyanobenzylamine produced may be recovered e.g. by distillation to remove ammonia and solvents present, followed by vacuum distillation of the residue, or by formation of the hydrates by dissolving the residue in water above the m.p. of the hydrates. The reaction is preferably carried out so that substantially no dinitrile remains at the end of the reaction. Examples are given of the preparation of 4-cyanobenzylamine, and bis-(4-cyanobenzyl) amine from terephthalonitrile, and 3-cyanobenzylamine from isophthalonitrile. 4-Cyanobenzylamine may be converted to the perchlorate with perchloric acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB814631A true GB814631A (en) | 1959-06-10 |
Family
ID=1593512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB93457A Expired GB814631A (en) | 1957-01-10 | The production of cyano benzylamines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB814631A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050544A (en) * | 1959-04-30 | 1962-08-21 | Allied Chem | Cyanobenzyl amine |
| US3335176A (en) * | 1962-04-13 | 1967-08-08 | Allied Chem | Aminomethyl carboxy dibenzyl amines and preparation thereof |
| US3720702A (en) * | 1969-12-29 | 1973-03-13 | Ciba Geigy Corp | Partial reduction of phthalonitriles |
| WO2001044171A1 (en) * | 1999-12-14 | 2001-06-21 | Showa Denko K. K. | Process for producing salt of cyanobenzylamine or derivative |
| JP2001233843A (en) * | 1999-12-14 | 2001-08-28 | Showa Denko Kk | Method for producing salt of cyanobenzylamines |
| US6284913B1 (en) | 1998-06-11 | 2001-09-04 | Astrazeneca Ab | Selective hydrogenation of a C3-C5 alkyl alchol |
| EP1378504A3 (en) * | 2002-07-01 | 2004-09-29 | Mitsubishi Gas Chemical Company, Inc. | Process for production of xylylenediamine and/or cyanobenzylamine |
| EP1762561A1 (en) | 2005-09-09 | 2007-03-14 | Mitsubishi Gas Chemical Company, Inc. | Process and catalysts for the preparation of amino compounds containing an aromatic ring |
-
1957
- 1957-01-10 GB GB93457A patent/GB814631A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050544A (en) * | 1959-04-30 | 1962-08-21 | Allied Chem | Cyanobenzyl amine |
| US3335176A (en) * | 1962-04-13 | 1967-08-08 | Allied Chem | Aminomethyl carboxy dibenzyl amines and preparation thereof |
| US3720702A (en) * | 1969-12-29 | 1973-03-13 | Ciba Geigy Corp | Partial reduction of phthalonitriles |
| US6284913B1 (en) | 1998-06-11 | 2001-09-04 | Astrazeneca Ab | Selective hydrogenation of a C3-C5 alkyl alchol |
| WO2001044171A1 (en) * | 1999-12-14 | 2001-06-21 | Showa Denko K. K. | Process for producing salt of cyanobenzylamine or derivative |
| JP2001233843A (en) * | 1999-12-14 | 2001-08-28 | Showa Denko Kk | Method for producing salt of cyanobenzylamines |
| US6392083B2 (en) | 1999-12-14 | 2002-05-21 | Showa Denko K.K. | Process for producing salts of cyanobenzylamines |
| EP1378504A3 (en) * | 2002-07-01 | 2004-09-29 | Mitsubishi Gas Chemical Company, Inc. | Process for production of xylylenediamine and/or cyanobenzylamine |
| US7119230B2 (en) | 2002-07-01 | 2006-10-10 | Mitsubishi Gas Chemical Co., Inc. | Process for production of xylylenediamine and/or cyanobenzylamine |
| EP1762561A1 (en) | 2005-09-09 | 2007-03-14 | Mitsubishi Gas Chemical Company, Inc. | Process and catalysts for the preparation of amino compounds containing an aromatic ring |
| US7449604B2 (en) | 2005-09-09 | 2008-11-11 | Mitsubishi Gas Chemical Company, Inc. | Production of aromatic ring-containing amino compounds and catalysts |
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