GB785108A - Manufacture of hexahydrobenzylamine - Google Patents
Manufacture of hexahydrobenzylamineInfo
- Publication number
- GB785108A GB785108A GB4417/56A GB441756A GB785108A GB 785108 A GB785108 A GB 785108A GB 4417/56 A GB4417/56 A GB 4417/56A GB 441756 A GB441756 A GB 441756A GB 785108 A GB785108 A GB 785108A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetic anhydride
- tetrahydrobenzonitrile
- mixture
- hexahydrobenzylamine
- nickel
- 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
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- GYBNBQFUPDFFQX-UHFFFAOYSA-N cyclohex-3-ene-1-carbonitrile Chemical compound N#CC1CCC=CC1 GYBNBQFUPDFFQX-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- -1 acetylamino compound Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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
Hexahydrobenzylamine is produced from tetrahydrobenzonitrile by catalytic hydrogenation in the presence of acetic anhydride, and subsequent hydrolysis of the acetylamino compound. Preferably, the tetrahydrobenzonitrile is dissolved in a mixture of glacial acetic acid and acetic anhydride, and after adding a hydrogenation catalyst such as finely distributed nickel, cobalt, palladium or platinum, especially Raney nickel, the mixture is treated with hydrogen in a pressure resistant vessel, while stirring at temperatures between 40-100 DEG C. and pressures between 20 and 300 atm. After evaporating the solvent and excess acetic anhydride, the reaction product is hydrolysed by boiling with hydrochloric acid, and the amine isolated by treatment with alkali.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH785108X | 1955-02-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB785108A true GB785108A (en) | 1957-10-23 |
Family
ID=4536525
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4417/56A Expired GB785108A (en) | 1955-02-14 | 1956-02-13 | Manufacture of hexahydrobenzylamine |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB785108A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3137727A (en) * | 1960-07-01 | 1964-06-16 | Eastman Kodak Co | 4-aminomethylcyclohexanemethanol |
US3143570A (en) * | 1960-07-01 | 1964-08-04 | Eastman Kodak Co | Method for preparing alicyclic diamines |
-
1956
- 1956-02-13 GB GB4417/56A patent/GB785108A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3137727A (en) * | 1960-07-01 | 1964-06-16 | Eastman Kodak Co | 4-aminomethylcyclohexanemethanol |
US3143570A (en) * | 1960-07-01 | 1964-08-04 | Eastman Kodak Co | Method for preparing alicyclic diamines |
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