GB796796A - Improved hydrolysis process for the manufacture of amines - Google Patents

Improved hydrolysis process for the manufacture of amines

Info

Publication number
GB796796A
GB796796A GB31734/55A GB3173455A GB796796A GB 796796 A GB796796 A GB 796796A GB 31734/55 A GB31734/55 A GB 31734/55A GB 3173455 A GB3173455 A GB 3173455A GB 796796 A GB796796 A GB 796796A
Authority
GB
United Kingdom
Prior art keywords
acid
formamide
mixture
hydrolysed
substituted
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
GB31734/55A
Inventor
George Henry Lang
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB31734/55A priority Critical patent/GB796796A/en
Publication of GB796796A publication Critical patent/GB796796A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a 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
    • C07C209/44—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
    • C07C209/50—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 carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • 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
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Abstract

Inisubstituted primary methylamines are obtained by hydrolysis of N-substituted formamides containing a tertiary carbon atom attached to amido nitrogen, which tertiary carbon atom may carry either aliphatic substituents or aliphatic substituents together with a cycloalkyl, an aralkyl or an aryl radical, or may be part of a monocyclic cycloaliphatic ring, the hydrolysis being carried out in the presence of acid at a temperature above 70 DEG C., preferably between 100 DEG and 120 DEG C. The acid used is preferably a strong mineral acid, e.g. sulphuric or hydrochloric acid, but strong organic acids, e.g. aryl or alkyl sulphonic acids or oxalic acid, may be used. Preferably at least one mol. of acid is used for each mol. of N-substituted formamide, and the acid may be mixed with water, a suitable mixture being one containing 10 to 85 per cent of acid by weight. The N-substituted formamides may be obtained by reaction of hydrogen cyanide, in the presence of an acid-reacting catalyst, with an olefin which gives a tertiary alkanol on reaction with water as described in Specification 796,572. Suitable starting materials are N - t - butyl formamide, N - (1,1,3,3 - tetramethylbutyl) - formamide, N - (1 - methylcyclohexyl) - formamide and N - (2 - phenylisopropyl) - formamide. The N - substituted formamide may be hydrolysed directly, without isolation from the reaction mixture in which it is formed. The products may be isolated by adding alkali metal hydroxide or carbonate, followed by extraction, distillation or mechanical separation. Typical products are t-butylamine, 1,1,3,3 - tetramethylbutylamine, 1 - methylcyclohexylamine and 2 - phenyl - isopropylamine. In examples: (1) N-t-octylformamide and 30 per cent sulphuric acid are refluxed for 2 hours and t-octylamine is isolated by distillation; (2) isobutene is passed into an aqueous mixture of sodium cyanide and sulphuric acid and the mixture is heated to 50 DEG to 55 DEG C., whereafter N-t-butylformamide separates as an upper layer on standing; the mixture is then heated to boiling under reflux for 1 hour to hydrolyse the N-t-butylformamide to t-butylamine; (3) commercial diisobutene (2 : 4 : 4 - trimethylpentene - 1 and 2,4,4 - trimethylpentene-2) sodium cyanide, water and sulphuric acid are heated to 50-55 DEG C. to give N - t - octylformide which is then hydrolysed to t-octylamine by boiling under reflux; (4) N-t-octylformamide is hydrolysed in presence of hydrochloric acid; (5) 1-methylcyclohexene is treated as in (3) to give 1-methylcyclohexylamine; (6) N-t-octylformamide is hydrolysed using oxalic acid solution.
GB31734/55A 1955-11-07 1955-11-07 Improved hydrolysis process for the manufacture of amines Expired GB796796A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB31734/55A GB796796A (en) 1955-11-07 1955-11-07 Improved hydrolysis process for the manufacture of amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31734/55A GB796796A (en) 1955-11-07 1955-11-07 Improved hydrolysis process for the manufacture of amines

Publications (1)

Publication Number Publication Date
GB796796A true GB796796A (en) 1958-06-18

Family

ID=10327591

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31734/55A Expired GB796796A (en) 1955-11-07 1955-11-07 Improved hydrolysis process for the manufacture of amines

Country Status (1)

Country Link
GB (1) GB796796A (en)

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