GB445805A - Improvements in the manufacture and production of organic sulphur compounds - Google Patents

Abstract

Aminoethanethiols and aminoalkylethanethiols are manufactured by causing an alkylene 1 : 2-sulphide to act on a primary or secondary monovalent or polyvalent amine (aliphatic, cycloaliphatic, aliphatic-aromatic, aromatic or heterocyclic) or a secondary heterocyclic base, below about 300 DEG C. The reaction may be performed by heating the mixture of reacting materials, if desired in the presence of solvents inert to the alkylene sulphides, e.g. benzine or benzene hydrocarbons or ethers, or by heating the amine, if desired dissolved or suspended in a suitable solvent, and then introducing the vaporous or liquid alkylene sulphide at the rate at which it is absorbed. In order to reduce the polymerizing action of the amines on the alkylene sulphides it is advantageous to reduce their basic action by the addition of suitable substances, e.g. phenols. The products are suitable for the preparation of dyestuffs, vulcanization accelerators, or auxiliary agents or assistants for the textile industry. In examples: (1) aniline and ethylene sulphide are heated under pressure to produce anilidomonoethanethiol; similarly o-toluidine yields o-toluidinomonoethanethiol, b -naphthylamine yields 2-naphthylaminomonoethanethiol and n-dodecylamine yields n-dodecylaminomonoethanethiol; (2) aniline and 1 : 2-propylene sulphide similarly yield anilidomonopropanethiol, whilst benzylamine yields benzylaminomonopropanethiol, n - butylamine yields a mixture of n-butylaminomono- and -dipropanethiols, and cyclohexylamine yields a mixture of cyclohexylaminomono- and -dipropanethiols; (3) piperidine and ethylene sulphide are heated under pressure, producing piperidinomonoethanethiol and piperidinoethanethioethanethiol; (4) propylene sulphide vapour is led into aniline to produce anilidomono- and -polypropanethiols; (5) monomethylaniline and ethylene sulphide are heated under pressure, yielding N-methylanilidomonoethanethiol; N-methyldodecylamine similarly yields N-methyldodecylaminoethanethiol; (6) aniline and ethylene sulphide are heated under pressure to produce anilidomono- and -diethanethiols; for the preparation of the diethanethiol, the monoethanethiol may be used as starting material; dibutylamine similarly yields dibutylaminomonoethanethiol and dibutylaminoethanethioethanethiol.