Patent GB-462720-A (GB)
Title: Manufacture of quaternary ammonium compounds
Filed: 1935-09-10
Abstract: Quaternary ammonium compounds are obtained by the action of tertiary aliphatic amines, containing at least one radicle of at least eight carbon atoms, on halogenated esters of the formula XRCOOR<1>, where X is halogen, R is an aliphatic hydrocarbon radicle containing up to four carbon atoms, and R<1> is an aliphatic hydrocarbon radicle containing up to five carbon atoms; the products may be saponified to replace the radicle R<1> by hydrogen.  Specified tertiary amines are hexadecylmethylglucamine, dodecyldimethylamine, oleyldiethanolamine, stearyldipolyethanolamine, and stearyldimethylamine; other suitable amines may be obtained from the acids of oils, fats and waxes by converting these into primary amines in known manner and alkylating, hydroxyalkylating, or polyhydroxyalkylating the products to the tertiary stage.  Suitable esters are those of chloracetic, a - and b -chloropropionic, and a -bromobutyric acids with aliphatic alcohols containing up to five carbon atoms.  The products are useful (a) as wetting, emulsifying and cleansing agents in the treatment of textiles, skins and leather, (b) as agents for softening, brightening, fulling or sizing textiles, (c) as levelling, through-dyeing and fixing agents in the dyeing industry, (d) as additions to mercerizing lyes, and (e) as agents for stabilizing foam in flotation processes; the products may be used in the form of aqueous solutions or dispersions of their solutions in organic solvents.  In the examples: (1) palmnut oil dimethylamine is treated with methyl chloracetate, and the product is saponified with a solution of soda or caustic soda; the specified amine may be replaced by a tertiary amine mixture obtainable by reducing the amides or nitriles of hardened fish-oil acids and treating the resulting primary amines with ethylene oxide or propylene oxide; (2) palmnut oil dimethylamine is treated with methyl b -chloropropionate; the product may be saponified with acids or alkalies; (3) stearyldimethylamine is treated with methyl g -chlorobutyrate.  The Provisional Specification refers p  generally to the reaction of tertiary amines with esters of halogenated carboxylic acids, and includes examples of the manufacture of products from (1) butyldiethanolamine and methyl or ethyl chloracetate; (2) triethanol-amine or dipropanolbutylamine and butyl-chloracetate; and (3) stearyldimethylamine and butyl a -bromolaurate.  The reaction of tributylamine with methyl chloracetate is also mentioned.ALSO:Quaternary ammonium compounds useful as emulsifying agents, are obtained by the action of tertiary aliphatic amines, containing at least one radicle of at least eight carbon atoms, on halogenated esters of the formula XRCOOR<1>, where X is halogen, R is an aliphatic hydrocarbon radicle containing up to four carbon atoms, and R<1> is an aliphatic hydrocarbon radicle containing up to five carbon atoms; the products may be saponified to replace the radicle R<1> by hydrogen.  Specified tertiary amines are hexadecylmethylglucamine, dodecyldimethylamine, oleyldiethanolamine, stearyldipolyethanolamine, and stearyldimethyl amine; other suitable amines may be obtained from the acids of oils, fats and waxes by converting these into primary amines in known manner and alkylating, hydroxyalkylating, or polyhydroxyalkylating the products to the tertiary stage. Suitable esters are those of chloracetic, a - and b -chloropropionic, and a -bromobutyric acids with aliphatic alcohols containing up to five carbon atoms.  The products may be used in the form of aqueous solutions or dispersions of their solutions in organic solvents.  In the examples, (1) palmnut oil dimethylamine is treated with methyl chloracetate, and the product is saponified with a solution of soda or caustic soda; the specified amine may be replaced by a tertiary amine mixture obtainable by reducing the amides or nitriles of hardened fish-oil acids and treating the resulting primary amines with ethylene oxide or propylene oxide; (2) palmnut oil dimethylamine is treated with methyl b -chloropropionate; the product may be saponified with acids or alkalies; (3) stearyldimethylamine is treated with methyl g -chlorobutyrate.  The Provisional Specification refers generally to the reaction of tertiary amines with esters of halogenated carboxylic acids, and includes examples of the p  manufacture of products from (1) butyl diethanolamine and methyl or ethyl chloracetate; (2) triethanolamine or dipropanolbutylamine and butyl chloracetate, and (3) stearyldimethylamine and butyl a -bromolaurate.  The reaction of tributylamine with methyl chloracetate is also mentioned.ALSO:Quaternary ammonium compounds useful as agents for stabilizing foam in flotation processes, are obtained by the action of tertiary aliphatic amines, containing at least one radicle of at least eight carbon atoms, on halogenated esters of the formula XRCOOR1, where X is halogen, R is an aliphatic hydrocarbon radicle containing up to four carbon atoms, and R1 is an aliphatic hydrocarbon radicle containing up to five carbon atoms; the products may be saponified to replace the radicle R1 by hydrogen.  Specified tertiary amines are hexadecylmethylglucamine, dodecyldimethylamine, oleyldiethanolamine, stearyldipolyethanolamine, and stearyldimethylamine; other suitable amines may be obtained from the acids of oils, fats and waxes by converting these into primary amines in known manner and alkylating, hydroxyalkylating, or polyhydroxyalkylating the products to the tertiary stage. Suitable esters are those of chloracetic, a - and b -chloropropionic, and a -bromobutyric acids with aliphatic alcohols containing up to five carbon atoms.  The products may be used in the form of aqueous solutions or dispersions of their solutions in organic solvents.  In the examples, (1) palmnut oil dimethylamine is treated with methyl chloracetate, and the product is saponified with a solution of soda or caustic soda; the specified amine may be replaced by a tertiary amine mixture obtainable by reducing the amides or nitriles of hardened fish-oil acids and treating the resulting primary amines with ethylene oxide or propylene oxide; (2) palmnut oil dimethylamine is treated with methyl b -chloropropionate; the product may be saponified with acids or alkalies; (3) stearyldimethylamine is treated with methyl g -chlorobutyrate.  The Provisional Specification refers generally to the reaction of tertiary amines with esters of halogenated carboxylic acids, and includes examples of the manufacture of products from (1) butyl diethanolamine and methyl or ethyl chloracetate; (2) triethanolamine or dipropanolbutylamine and butyl chloracetate, and (3) stearyldimethylamine and butyl a -bromolaurate.  The reaction of tributylamine with methyl chloracetate is also mentioned.