Patent GB-501004-A (GB)
Title: Manufacture of amides
Filed: 1937-08-10
Abstract: 501,004. Wetting &c. agents. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.) Aug. 10, 1937, No. 21988. [Classes 2 (iii) and 15 (ii)] [Also in Group III] Amides are manufactured by causing the anhydride or a halide of a carboxylic acid of the general formula A.O.R1.COOH, where A is an isocyclic ring system substituted by one or more hydrocarbon or acyl radicles of at least four carbon atoms and R1 is an aliphatic hydrocarbon radicle, the chain of which may be interrupted by oxygen, to react with a compound of the general formula <R>3H >N.R2.Y, where R2 is an aliphatic, cycloaliphatic, aliphatic-aromatic or aromatic radicle, R3 is an aliphatic, cycloaliphatic, aliphatic-aromatic or aromatic hydrocarbon radicle or hydrogen and Y is -OSO3Me or -SO3Me, where Me is an alkali metal. The reaction may be effected in aqueous alkaline solution or in the presence of pyridine or other organic base. Those of the products which contain a sulphuric ester group may alternatively be manufactured by reacting an acid of the above formula, or a halide thereof, with a hydroxyamine and converting the hydroxy group into a sulphuric ester and, if desired, into a salt of the ester. Those of the products which contain a sodium methanesulphonate group may alternatively be manufactured by reacting the amides of the carboxylic acids with formaldehyde and sodium bisulphite at a raised temperature. The products may be employed as wetting, washing, purifying dispersing or emulsifying agents, either in the form of their alkali metal salts, or after converting these into the free sulphonic acids or sulphuric acid esters. The water-soluble salts may be used as capillary agents in the textile, leather or paper-making industries, e.g. the sodium or potassium salts may be applied as wetting, bucking or fulling agents, as washing agents, e.g. for wool or fine laundry goods, or as hair washes. Some of the products may also be used as auxiliary agents in the dyeing industry for producing even dyeings penetrating through the goods, as dispersing agents for dyestuffs and for " soaping " dyeings. The products may be used alone or in admixture with other textile adjuvants, e.g. turkey red oil, alkylated naphthalenesulphonic acids or the products known as fatty acid condensation products or fatty alcohol sulphonates, with organic solvents, e.g. benzyl alcohol, chlorinated hydrocarbons, monoglycol ethers or cyclohexanol, with substances yielding oxygen, e.g. sodium perborate or perpyrophosphate, with stabilizers, e.g. magnesium salts, with other inorganic salts, e.g. trisodium phosphate, sodium pyrophosphate, sodium hexametaphosphate or silicates, or with organic salts capable of binding metal ions in a complex manner, e.g. sodium nitriloacetate or sodium citrate. In examples: (1) p-isooctylphenoxyacetyl chloride (obtainable by treating the acid with phosphorus trichloride or thionyl chloride) is heated with an aqueous solution of the sodium salt of methyltaurine, with the addition of caustic soda ; (2) a mixture of isomeric tetradecylcresoxyacetic acid chlorides (obtained by condensing technical olefine mixtures, mainly isomeric tetradecylenes, with cresoxyacetic acids and converting the product to the chlorides) is reacted similarly with taurine sodium salt; (3) dibutyl-#-naphthoxyacetyl chloride (obtainable by treating the acid with phosphorus trichloride or thionyl chloride) is reacted as in (2) ; (4) p-cyclohexylphenoxyacetyl chloride and caustic soda are run simultaneously into a solution of butyltaurine sodium salt; (5) p-isobutylcyclohexyloxyacetyl chloride is similarly reacted with sodium m-aminobenzenesulphonate ; (6) benzylphenoxypropionic acid chloride is similarly reacted with the sodium salt of the acid sulphuric ester of ethanolamine ; the same product is produced by heating benzylphenoxypropionic acid with ethanolamine, preferably in vacuo, and treating the product with chlorsulphonic acid in ether; (7) p-caproylphenoxyacetyl chloride is reacted with the sodium salt of mothyltaurine in aqueous solution with the addition of caustic soda ; (8) p - isododecylphenoxyacetic acid ethanolamide, prepared by reacting the corresponding acid chloride with ethanolamine or by heating the free acid with ethanolamine, is treated with chlorsulphonic acid in ether ; (9) p-isooctylphenoxyacetyl chloride is reacted with sodium aminomethanesulphonate with the addition of caustic soda; the same product is obtainable by reacting p-isooctylphenoxyacetic acid amide with formaldehyde and sodium bisulphite. Other starting materials specified are, on the one hand, the anhydrides or halides of p-butylphenoxyacetic acids, isotetradecylphenoxyacetic acids, perhydrobenzoylphenoxyacetic acid of the formula isooctylcresoxyacetic acids, p.isooctylphenoxyacetic acid, di- or tributylphenoxyacetic acids, isododecylphenoxypropionic acids, p-caproylphenoxypropionic acid, p-isooctylphenoxy-#- butyric acid, and isododecyl-#-naphthoxypropionic acids, and on the other hand the alkali metal salts of isoheptyltaurine, alpha-ethylhexyltaurine, # methylaminodiethyl ether . #<1>- sulphonic acid, dodecyltaurine, gamma-aminopropane-alpha-sulphonic acid, phenyltaurine, cyclohexyltaurine, benzylamine - p - sulphonic acid, sulphanilic acid and 1 : 4-naphthylaminesulphonic acid. Specifications 452,577 and 452,866 are referred to.