Patent GB-824447-A (GB)
Title: Improved process of preparing anionic surface active agents
Filed: 1957-07-29
Abstract: Anionic surface-active agents prepared by reaction of carboxylic acids containing at least 8 carbon atoms with compounds of general formula <FORM:0824447/III/1> where R = H1 or C1-C2 alkyl, and M = alkali metal, alkaline earth metal or a sterically hindered secondary or tertiary amine (see Group IV (b)) are used as additives to petroleum lubricating oils, for breaking petroleum emulsions and, in aqueous solution, emulsions or in oils, used for the milling or cutting of metals.ALSO:The invention comprises a process for the preparation of esters of a 2-hydroxy alkane sulphonic acid, by reaction of one mol. of a salt of such an acid, of general formula <FORM:0824447/IV (b)/1> where R is hydrogen, methyl or ethyl and M is an alkali metal, alkaline earth metal or a sterically hindered secondary or tertiary amine with 1 to 10 mols. of an aliphatic, aromatic or alicyclic carboxylic acid having at least eight carbon atoms, at 185-300 DEG C. in the presence of o-phosphoric acid in an amount from 2-2 1/2 % by weight of the carboxylic acid, and the reaction is carried out at atmospheric pressure in an inert atmosphere of, e.g., nitrogen, carbon dioxide or steam, at a pH of 2.0 to 5.  The reaction time is usually between 1/2 and 2 hours. Monocarboxylic acids specified as starting materials are caprylic, pelargonic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, lauronolic, cycloalkane or heptane carboxylic, o- or mtoluic, cumic, phenylacetic, tall oil, hydrogenated tall and tallow, naphthenic, abietic, dodecylbenzoic, nonylbenzoic, octylbenzoic, and nonylnaphthoic acids.  Acids from oxo alcohols, and aldehydes, or from oxidized petroleum fractions may be used, as well as acid mixtures from natural plant and animal oils such as olive, tallow, castor, peanut, coconut, soybean, cottonseed, ucahuba, linseed, cod, herring, menhaden, neetsfoot, sperm, palm, corn, butter, babassu, kapok, hempseed, mustard, rubberseed, rape, safflower, and sesame oils.  2-Hydroxyalkane sulphonic acid salts specified, which may be condensed with the above monocarboxylic acids, are the calcium, magnesium, barium, lithium, sodium, potassium, trioctylamine, N,N-diphenylmethylamine, N,N - dimethyloctadecylamine, N,N - dioctodecylethylamine, and N,N-dihexadecylmethylamine salts of isethionic, 2-hydroxy-3-butane sulphonic, 2-hydroxy-propane-sulphonic, and 2-hydroxy-1-butane sulphonic acids.  These salts may be used as aqueous solutions or as dry powders; in the former case the water is removed during the reaction in the presence of a monocarboxylic acid.  Examples are given of the reaction between (A) a coconut oil fatty acid and sodium isethionate, (1) in the absence of a catalyst, and (2) in the presence of boric acid at pH 6.6, (3) in accordance with the invention; (B) lauric acid and sodium isethionate; (C) stearic acid and sodium isethionate; (D) a coconut fatty acid and (1) sodium BETA-methylisethionate, (2) the potassium salt of 2-hydroxypropane sulphonic acid, (3) the sodium salt of 2-hydroxy-1-butane sulphonic acid; (E) lauric acid and the tri-octylamine salt of 2-hydroxy-1 -butane sulphonic acid.