Patent GB-465513-A (GB)
Title: Manufacture of amino-carboxylic acids, their salts and functional derivatives
Filed: 1935-08-06
Abstract: Aminoacids or derivatives thereof are obtained by reacting an unsaturated carboxylic acid or a derivative thereof with ammonia or a primary or secondary amine in sufficient proportion to effect addition at the double bond after allowing for the possible formation of a salt or an amide.  The preferred acids are a , b -unsaturated carboxylic acids, or carboxylic acids containing conjugated double bonds; the acid derivatives which may be used include the salts, esters, amides and anhydrides.  The components must be so selected that the free acid corresponding to the final product contains at least six carbon atoms, i.e. the unsaturated acid reagent must contain at least six carbon atoms when ammonia is the other reagent, but may contain a lower number of carbon atoms if a primary or secondary amine is used instead of ammonia. Specified acids or derivatives are crotonic acid, isocrotonic acid, sorbic acid, maleic acid, maleic anhydride, acrylic acid, methacrylic acid and oleic acid.  Specified amines are methylamine, ethylamine, diethylamine, butylamine, dodecylamine, heptadecylamine, stearylamine, oleylamine, methyloleylamine, glucamine dodecylglucamine, amines obtainable from montanic, naphthenic and resin acids, aniline, naphthylamine and toluidine. The products are useful as wetting and washing agents, and some of them may be used in dyeing processes in acid or alkaline baths, or as additions to printing pastes; they may be used alone or with appropriate additions, such as inorganic salts, soaps, sulphonated products, bleaching agents, clay, fat-solvents, and mucilage.  In the examples, (1) sodium crotonate solution is heated with butylamine to yield sodium butylaminobutyrate; (2) crotonic acid is heated in alcohol with stearylamine and the product is neutralized with caustic soda, sodium stearylaminobutyrate being obtained; (3) sodium crotonate and diethylamine yield sodium diethylaminobutyrate; (4) sodium, maleate and butylamine yield sodium butylaminosuccinate; (5) crotonic acid and p-toluidine yield b -p-tolylaminobutyric acid p-toluidide; (6) sodium oleate and ammonia yield sodium aminostearate; (7) sodium sorbate and methylamine yield sodium di(methylamino)-caproate.ALSO:Aminoacids or derivatives thereof are obtained by reacting an unsaturated carboxylic acid or a derivative thereof with ammonia or a primary or secondary amine in sufficient proportion to effect addition at the double bond after allowing for the possible formation of a salt or an amide.  The preferred acids are a .b  - unsaturated carboxylic acids, or carboxylic acids containing conjugated double bonds; the acid derivatives which may be used include the salts, esters, amides and anhydrides.  The components must be so selected that the free acid corresponding to the final product contains at least six carbon atoms, i.e. the unsaturated acid reagent must contain at least six carbon atoms when ammonia is the other reagent, but may contain a lower number of carbon atoms if a primary or secondary amine is used instead of ammonia. Specified acids or derivatives are crotonic acid, isocrotonic acid, sorbic acid, maleic acid, maleic anhydride, acrylic acid, methacrylic acid and oleic acid.  Specified amines are methylamine, ethylamine, diethylamine, butylamine, dodecylamine, heptadecylamine, stearylamine, oleylamine, methyloleylamine, glucamine, dodecylglucamine, amines obtainable from montanic, naphthenic and resin acids, aniline, naphthylamine and toluidine. The products are useful as washing agents they may be used alone or with appropriate additions, such as inorganic salts, soaps, sulphonated products, bleaching agents, clay, fat-solvents, and mucilage.  In the examples: (1) sodium crotonate solution is heated with butylamine to yield sodium butylaminobutyrate; (2) crotonic acid is heated in alcohol with stearylamine and the product is neutralized with caustic soda, sodium stearylaminobutyrate being obtained; (3) sodium crotonate and diethylamine yield sodium diethylaminobutyrate; (4) sodium maleate and butylamine yield sodium butylaminosuccinate; (5) crotonic acid and p-toluidine yield b -p-tolylaminobutyric acid p-toluidide; (6) sodium oleate and ammonia yield sodium amino-stearate; (7) sodium sorbate and methylamine yield sodium di(methylamino)caproate.