Patent GB-869744-A (GB)
Title: Improvements in the manufacture of surface-active acylated hydroxy-sulphonates
Inventor: ALPHEN JAN VAN
IPC: C11D1/28
Filed: 1958-04-29
Abstract: A mixture of surface-active agents of the general formula RCOOR1SO3M, wherein R is a C9-17 alkyl radical, R1 is a divalent hydrocarbon or dialkyl ether radical containing 2 to 8 carbon atoms and M is an alkali metal, ammonium or substituted ammonium radical, is prepared by heating a mixture of salts of the formula HO.R1.SO3M which melts below 180 DEG  C., with an acid of the formula RCOOH at a temperature below 200 DEG C. but above the melting point of the mixture of salts and under conditions such that water is removed.  The mixture of salts used may have different cations or different anions or both. Reaction is preferably effected in the presence of a reaction-promoting compound, generally in an amount of up to 10% by weight of the reaction mixture, and which is (a) a salt of a base weaker than the alkaline earths and an inorganic or organic acid having a dissociation constant greater than 1 x 10-6, excluding those salts defined above as reactants, or (b) an organic acid stronger than the reactant carboxylic acid; and numerous examples of both are given (Specifications 848,463 and 853,590).  Preferably, all the promotor is first added to a portion of the reactants and then subsequently the remainder of the reactants is added gradually.  A small portion of preformed product may also be added initially.  The reactants may be used in stoichiometrical amounts or an excess of the said RCOOH may be used.  The excess acid may thereafter be distilled off.  The process may be operated continuously.  The product if necessary may be partially or wholly neutralised and may be used in detergent compositions (see Group III).  In typical Examples: (1) lauric acid is reacted with a mixture of sodium and potassium isethionates using p-toluene sulphonic acid, hydrated stannic chloride or hydrated aluminium sulphate as promotor; (2) lauric acid is similarly reacted with a mixture of sodium isethionate and 2-hydroxy-1-sulphonate.  Numerous other acids RCOOH are mentioned including oleic acid and coconut or hydrogenated coconut oil fatty acid.  R1 in the above formula may represent a butylene or -C2H4-O-C2H4-radical.  According to the Provisional Specification, in the above formulae R may be a monovalent organic radical, R1 a small divalent organic radical, wherein R and R1 may contain ring systems, and the reaction-promotors comprise acid inorganic or organic compounds generally, additional examples being given.ALSO:Detergent compositions comprise a mixture of compounds of the general formula RCOOR1SO3M wherein R is a C9-C17 alkyl radical, R1 is a divalent hydrocarbon or dialkylene ether radical containing 2 to 8 carbon atoms and M is an alkali metal, ammonium or substituted-ammonium radical, prepared in specified manner from carboxylic acids RCOOH and mixtures of salts of the formula HO.R1.SO3M which melt at below 180 DEG C. (see Group IV(b)).  The mixture of salts used may have different cations, different anions or both.  Reaction may be effected in the presence of a reaction-promotor which is (a) a salt of a base weaker than the alkaline earths and an inorganic or organic acid having a dissociation constant greater than 1 X 10-6, excluding those salts defined above as reactants, or (b) an organic acid stronger than the reactant RCOOH, for example toluene-, naphthalene-, dodecyl benzene- and dodecanesulphonic acids, isethionic acid, lauroyl isethionic acid, monododecyl phosphoric acid, monochloracetic acid; the chloride, sulphate, isethionate, dodecyl benzene sulphonate or dodecyl sulphate of aluminium; tin and zinc chlorides, zinc sulphate and isethionate and hydrazine chloride.  The carboxylic acid RCOOH may be for example lauric, stearic or oleic acid or acids derived from various fats or fatty oils.  The acid may be used in excess, the surplus acid if desired being left in the product, which may subsequently be wholly or partially neutralised with alkali.  The final products may be tabletted.  Specified values for R1 and M include ethylene, propylene, butylene and the radical -C2H4OC2H4-, and sodium and potassium.  According to the Provisional Specification, R may represent any monovalent organic radical and R1 a small divalent organic radical and each may comprise a ring system; also, the reaction promoter may be any acid inorganic or organic compound such as sulphuric acid, phosphoric acid, thionyl chloride, a phosphorus chloride, hydrobromic acid, boric acid, chlorosulphonic acid, acetyl chloride, lauroyl chloride, ethyl chloro formate, aluminium acetate and aluminium acetyl acetonate. Specifications 848,463 and 853,590 are referred to.