GB1164354A - Process for the Hydrogenation of Nitriles. - Google Patents
Process for the Hydrogenation of Nitriles.Info
- Publication number
- GB1164354A GB1164354A GB3079367A GB3079367A GB1164354A GB 1164354 A GB1164354 A GB 1164354A GB 3079367 A GB3079367 A GB 3079367A GB 3079367 A GB3079367 A GB 3079367A GB 1164354 A GB1164354 A GB 1164354A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogenation
- nitriles
- byproduct
- july
- mixture
- 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
- 238000005984 hydrogenation reaction Methods 0.000 title abstract 6
- 150000002825 nitriles Chemical class 0.000 title abstract 4
- 238000000034 method Methods 0.000 title 1
- 239000006227 byproduct Substances 0.000 abstract 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000003141 primary amines Chemical class 0.000 abstract 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 abstract 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 abstract 1
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 abstract 1
- OZOHTVFCSKFMLL-UHFFFAOYSA-N 4-amino-5-aminomethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CN)C(N)=N1 OZOHTVFCSKFMLL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ZBLACDIKXKCJGF-WDSKDSINSA-N [(1r,2r)-2-(aminomethyl)cyclobutyl]methanamine Chemical compound NC[C@@H]1CC[C@H]1CN ZBLACDIKXKCJGF-WDSKDSINSA-N 0.000 abstract 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 abstract 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 abstract 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- -1 fatty acid nitriles Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
1,164,354. Hydrogenation of nitriles. TOYO RAYON K.K. 4 July, 1967 [4 July, 1966], No. 30793/67. Heading C2C. Primary amines are produced by the hydrogenation of nitriles with hydrogen in the presence of a base, alumina, water, a hydrogenation catalyst and optionally an inert organic solvent. In the examples, dodecylamine, 2-methyl-4- amino - 5 - aminomethylpyrimidine, # - aminoethylbenzene, 3 - aminomethylpyridine, hexamethylene diamine, p-xylylenediamine, dodecamethylenediamine, 2 - methylpentamethylenediamine, trans - 1,2 - diaminomethylcyclobutane are obtained by hydrogenating the appropriate nitriles, dinitriles or aminonitriles; and a mixture of primary amines are obtained to form a mixture of fatty acid nitriles. Hexamethyleneimine is obtained as a byproduct in the hydrogenation of #-aminocapronitrile and adiponitrile. 3-Methylpiperidine is produced as a byproduct in the hydrogenation of 2-methylglutaronitrile.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4304166 | 1966-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1164354A true GB1164354A (en) | 1969-09-17 |
Family
ID=12652805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3079367A Expired GB1164354A (en) | 1966-07-04 | 1967-07-04 | Process for the Hydrogenation of Nitriles. |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE700877A (en) |
| GB (1) | GB1164354A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4375003A (en) * | 1978-07-13 | 1983-02-22 | Nalco Chemical Company | Method for the hydrogenation of nitriles to primary amines |
| US4552982A (en) * | 1983-08-01 | 1985-11-12 | Eli Lilly And Company | Synthesis of 9-carbamoyl-9-(3-aminopropyl)fluorenes |
| US5149816A (en) * | 1988-07-11 | 1992-09-22 | Reilly Industries | High temperature process for selective production of 3-methylpyridine |
| GB2267438A (en) * | 1992-05-28 | 1993-12-08 | British Tech Group | Alicyclic diamine plant fungicides |
| WO2002096862A3 (en) * | 2001-05-31 | 2003-07-31 | Du Pont | Environmentally friendly process for the hydrogenation of dinitriles |
| WO2005026101A1 (en) * | 2003-09-10 | 2005-03-24 | Basf Aktiengesellschaft | Method for producing xylylenediamine |
| WO2005028417A1 (en) * | 2003-09-10 | 2005-03-31 | Basf Aktiengesellschaft | Method for producing xylylenediamine (xda) |
| WO2006077233A1 (en) * | 2005-01-24 | 2006-07-27 | Basf Aktiengesellschaft | Method for producing a xylylene diamine |
| KR100613404B1 (en) | 2005-03-24 | 2006-08-17 | 한국과학기술연구원 | Method for producing xylenediamine using imidazoles |
| WO2025119889A1 (en) | 2023-12-07 | 2025-06-12 | Basf Se | Process for manufacturing an aliphatic diamine |
-
1967
- 1967-07-03 BE BE700877D patent/BE700877A/xx unknown
- 1967-07-04 GB GB3079367A patent/GB1164354A/en not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4375003A (en) * | 1978-07-13 | 1983-02-22 | Nalco Chemical Company | Method for the hydrogenation of nitriles to primary amines |
| US4552982A (en) * | 1983-08-01 | 1985-11-12 | Eli Lilly And Company | Synthesis of 9-carbamoyl-9-(3-aminopropyl)fluorenes |
| US5149816A (en) * | 1988-07-11 | 1992-09-22 | Reilly Industries | High temperature process for selective production of 3-methylpyridine |
| US5583261A (en) * | 1992-05-28 | 1996-12-10 | British Technology Group Ltd. | Alicyclic diamine fungicides |
| GB2267438B (en) * | 1992-05-28 | 1995-04-19 | British Tech Group | Alicyclic diamine fungicides |
| US5464873A (en) * | 1992-05-28 | 1995-11-07 | British Technology Group Limited | Alicyclic diamine fungicides |
| GB2267438A (en) * | 1992-05-28 | 1993-12-08 | British Tech Group | Alicyclic diamine plant fungicides |
| WO2002096862A3 (en) * | 2001-05-31 | 2003-07-31 | Du Pont | Environmentally friendly process for the hydrogenation of dinitriles |
| WO2005026101A1 (en) * | 2003-09-10 | 2005-03-24 | Basf Aktiengesellschaft | Method for producing xylylenediamine |
| WO2005028417A1 (en) * | 2003-09-10 | 2005-03-31 | Basf Aktiengesellschaft | Method for producing xylylenediamine (xda) |
| US7541497B2 (en) | 2003-09-10 | 2009-06-02 | Basf Aktiengesellschaft | Method for producing xylylenediamine (XDA) |
| WO2006077233A1 (en) * | 2005-01-24 | 2006-07-27 | Basf Aktiengesellschaft | Method for producing a xylylene diamine |
| KR100613404B1 (en) | 2005-03-24 | 2006-08-17 | 한국과학기술연구원 | Method for producing xylenediamine using imidazoles |
| WO2025119889A1 (en) | 2023-12-07 | 2025-06-12 | Basf Se | Process for manufacturing an aliphatic diamine |
Also Published As
| Publication number | Publication date |
|---|---|
| BE700877A (en) | 1967-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |