Patent GB-853590-A (GB)
Title: Improvements in the manufacture of surface-active acylated hydroxysulphonates
Inventor: ALPHEN JAN VAN
IPC: C07C309/42
Filed: 1957-05-10
Abstract: Surface-active agents of the general formula RCOOR1.SO3M wherein R is a monovalent hydrocarbon radical containing 7-19 carbon atoms, R1 is a divalent hydrocarbon or dialkylene ether radical containing 2-8 carbon atoms and M is an alkali metal are prepared by heating under conditions such that water is removed, an acid RCOOH with a hydroxy sulphonic acid salt HO. R1. SO3 M in the presence of, as a reaction-promoting compound, an organic acid which is a stronger acid than the acylating acid RCOOH.  Specified promoters are p-toluene sulphonic acid, b -naphthalene sulphonic acid, dodecyl benzene sulphonic acid, dodecane sulphonic acid, isethionic acid, acylated isethionic acids such as lauroyl isethionic acid, mono dodecyl phosphoric acid and mono chloracetic acid.  The promoter is preferably added to a small proportion of the reagents, the remainder of the reagents being added subsequently.  Generally, the promoter is used in amounts from 0,01 to 10% by weight of the reaction mixture. The esterification is normally effected by 200 DEG -250 DEG  C. with excess of the acid RCOOH in an oxygen-free atmosphere.  A small amount of preformed ester-product may be added during the initial stages of the reaction.  Water of reaction may be removed at or below atmospheric pressure or with the aid of any oxygen-free gas. Excess acylating acid may be removed or retained.  The resulting product may be bleached with hydrogen peroxide.  It can be wholly or partially neutralised with alkali.  Examples describe the interaction of sodium isethionate with lauric acid and coconut oil fatty acids (hydrogenated or otherwise) in the presence of various of the above mentioned promoters and a comparative experiment is described where the promotor is omitted.  Other specified reagents are the sodium salts of methyl isethionic, dimethyl isethionic, 3-hydroxy propane and hydroxy butane sulphonic acids and the acid HO-C2H4.O.C2H4SO3H ; myristic, palmitic, stearic, oleic and various naturally occurring fatty acid mixtures.  According to the Provisional Specification R is a monovalent organic radical and R1 a small divalent organic radical which may consist of or contain a ring system.ALSO:Surface active compositions comprising compounds of the general formula RCOOR1SO3M wherein R is a monovalent hydrocarbon radical containing 7-19 carbon atoms, R1 is a divalent hydrocarbon or dialkylene ether radical containing 2-8 carbon atoms and M is an alkali metal, are prepared by heating, under conditions such that water is removed, an acid RCOOH with a hydroxy sulphonic acid salt HO.R1.SO3M in the presence of, as a reaction promoting compound, an organic acid which is a stronger acid than the acylating acid RCOOH.  Specified promoters are p-toluene sulphonic acid, b -naphthalene sulphonic acid, dodecyl benzene sulphonic acid, dodecane sulphonic acid, isethionic acid, acylated isethionic acids, e.g., lauroyl isethionic acid, mono dodecyl phosphoric acid and mono chloracitic acid; these promoters remain in the final product.  A fatty acid acylating acid RCOOH is preferably used in excess in the reaction and the unchanged acid may be retained in the product.  The final reaction product may thereafter be wholly or partially neutralised with alkali, if desired after bleaching with hydrogen peroxide.  Specified acylating acids include lauric, myristic, palmitic, stearic and oleic acids and naturally occurring fatty acid mixtures.  Suitable hydroxy sulphonates include the sodium salts of isethionic acid, methyl isethionic acid, dimethyl isethionic acid, hydroxy propane and butane sulphonic acids and the acid HO.C2H4.O.C2H4.SO3H.  Examples are given.  According to the Provisional Specification, R may represent any organic radical and R1 a small organic radical and either may include a ring system.