GB785108A - Manufacture of hexahydrobenzylamine - Google Patents

Manufacture of hexahydrobenzylamine

Info

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
Application number
GB4417/56A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
National Starch and Chemical Investment Holding Corp
Original Assignee
JR Geigy AG
National Starch and Chemical Investment Holding Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by JR Geigy AG, National Starch and Chemical Investment Holding Corp filed Critical JR Geigy AG
Publication of GB785108A publication Critical patent/GB785108A/en
Expired legal-status Critical Current

Links

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.
GB4417/56A 1955-02-14 1956-02-13 Manufacture of hexahydrobenzylamine Expired GB785108A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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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