Patent GB-800827-A (GB)
Title: Production of n-acyl taurides
Filed: 1955-11-09
Abstract: A detergent composition comprises an N-acyl taurine salt of the formula R1R1N-CHR-CHR-SO3M wherein R is H or a C1-3 alkyl radical, R1 is H or a C1-20 hydrocarbon radical, R2 is an acyl radical derived from an aliphatic or alicyclic carboxylic acid having at least 8 carbon atoms and M is an alkali metal (Na, K and Li specified) or alkaline earth metal (Ca, Mg and Ba specified) cation, together with an Na, K or triethanolamine salt of an aliphatic or alicyclic carboxylic acid having at least 8 carbon atoms.  The compositions are suitably prepared by acylating the corresponding taurine salt with an excess of carboxylic acid acylating agent followed by saponification of the unused carboxylic acid in situ. The detergent compositions may be produced in particulate or bar form and may be mixed with soda ash and sodium tripolyphosphate; they may be used as ingredients of paint brush cleaning, metal cleaning, dry cleaning and shampoo compositions; they may be employed in aqueous solutions as emulsifying agents for asphalt compositions, rubber, oils, fats, waxes, hydrocarbon substitution products and resins; they may be added to petroleum lubricating oils and are used to break emulsions of crude petroleum and salt water as obtained from oil wells.ALSO:N-Higher acyl taurine salts are prepared by heating at least 1.2 mols. of an aliphatic or alicyclic carboxylic acid having at least 8 carbon atoms with one mol. of a taurine salt of the formula: <FORM:0800827/IV (b)/1> wherein R1 is H or a C1-20 hydrocarbon radical, R is H or a C1-3 alkyl radical and M is an alkali metal or alkaline earth metal cation, in an inert atmosphere at a temperature of 200-320 DEG  C. while removing the water formed during the reaction.  The excess of acylating acid is preferably saponified in situ with caustic alkali or amines such as triethanolamine.  The inert atmosphere may be provided by a vacuum or by nitrogen gas.  The reaction is carried out with or without a solvent such as a hydrocarbon, halogenated hydrocarbon or nitrated hydrocarbon.  Specified acylating acids are caprylic, pelargonic, capric, lauric, myristic, palmitic, stearic, oleic, ricinoleic, linoleic, undecylenic, tall oil, naphthenic and abietic acids; those derived from olive, tallow, castor, peanut, coconut, soybean, cotton seed, ucahuba, linseed, cod, herring, menhaden, neatsfoot, sperm, palm, corn, butter, babassu, kapok, hempseed, mustard, rubber seed, rape, safflower and sesame oils; those derived from the oxidation fractions of petroleum and from oxo-aldehydes; and hydrogenated derivatives of the foregoing unsaturated acids.  Specified 2-aminoalkane sulphonates are the Na, K, Li, Ca, Mg and Ba salts of taurine, N-methyl-, N-ethyl-, N-propyl-, N-isopropyl-, N-butyl-, N-isobutyl-, N-tertiarybutyl-, N-amyl-, N-hexyl-, N-cyclohexyl-, N-phenyl-, N-octyl-, N-dodecyl- and N-stearyl-taurines, N - methyl - 2 - methyl - taurine, N-methyl - 2 - ethyl - taurine and N - methyl-1 : 2 - dimethyl - taurine.  The examples describe the preparation of the sodium salts of N-stearoyl - N - methyl taurine, N - lauroyl - N - methyl taurine, N - oleoyl - N - methyl taurine, N - palmitoyl - N - methyl taurine, N - naphthenic acid acyl-N-methyl taurine and N-tall oil acyl - N - methyl taurine, and of the inner salt of N-stearoyl-N-methyl taurine by way of comparison.ALSO:A detergent composition comprising an N-acyl taurine salt of the formula R2R1N-CHR-CHR-SO3M, wherein R is H or a C1-3 alkyl radical, R1 is H or a C1-20 hydrocarbon radical, R2 is an acyl radical derived from an aliphatic or alicyclic carboxylic acid having at least 8 carbon atoms and M is an alkali metal (Na, K and Li specified) or alkaline earth metal (Ca, Mg and Ba specified) cation, together with an Na, K or triethanolamine salt of an or aliphatic alicyclic carboxylic acid having at least 8 carbon atoms may be used for the conditioning of soil.ALSO:A composition comprising an N - acyl taurine salt of the formula R2 R1 N - CHR - CHR-SO3M, wherein R is H or a C1- alkyl radical, R1 is H or a C1-20 hydrocarbon radical, R2 is an acyl radical derived from an aliphatic or alicyclic carboxylic acid having at least eight carbon atoms and M is an alkali metal (Na, K and Li specified) or alkaline earth metal (Ca, Mg and Ba specified) cation, together with an Na, K or triethanolamine salt of an aliphatic or alicyclic carboxylic acid having at least eight carbon atoms may be used in acid pickling baths and in acid cleaning compositions, as a corrosion inhibitor, as a rust inhibitor, and as a froth flotation agent.