Patent GB-870456-A (GB)
Title: Aliphatic glycidyl ethers and the preparation of sulphonates therefrom
IPC: C07D303/02
Filed: 1957-12-06
Abstract: The invention comprises firstly a process for the preparation of alkyl (including alkenyl) glyceryl ether sulphonates comprising reacting 100 molar parts of a saturated or ethylenically unsaturated fatty alcohol containing 10 to 20 carbon atoms with from 105 to 135 molar parts of epichlorhydrin, treating the resulting alkyl glyceryl chloroether with an aqueous alkali metal hydroxide solution having a concentration of 25-50% by weight of metal hydroxide to epoxidise the said product, separating the resultant mixture into a substantially inorganic salt-free epoxidised ether phase and an aqueous phase and sulphonating the epoxidised ether with an aqueous solution of alkali metal sulphite and alkali metal bisulphite proportioned to give a sulphonated product having a pH of about 5 to about 8.  The invention also comprises a substantially inorganic salt-free mixture of glycidyl ethers containing at least 10 but not more than 30 mole per cent. of glycidyl ethers of the formula:  <FORM:0870456/IV (b)/1> where R is a C10-20 alkyl or alkenyl radical and X is -Cl or OH, the mixture of glycidyl ethers being the epoxidised ether phase obtained by carrying out the first three stages of the above process.  The reaction between the fatty alcohol and epichlorhydrin may be effected following the procedure of Specification 802,325 and yields a mixture of ethers having the general formula:  <FORM:0870456/IV (b)/2> n being an integer from 1 to 4 containing 10-30 mole per cent. of the diglyceryl compound.  The epoxidation may be effected with 0-50% excess of the stoichiometric amount of alkali metal hydroxide required for complete epoxidation of the ether mixture and preferably at 160 DEG -200 DEG F. or higher, suitably in an autoclave. Separation of the resulting expoxidised ether can be carried out by settling or centrifuging; water may be added to ensure removal of the last traces of salt.  The sulphonation of the epoxidised ether may be carried out with a moisture content at below 50%.  Reaction is preferably initiated by seeding with a small amount of alkyl glycenyl ether sulphonate.  The resulting alkali metal salts may be converted into for example the calcium, magnesium, ammonium or alkylol amine salts by treating with an ion-exchange resin to liberate the free acid which is then neutralized with the appropriate base.  In the examples a middle cut of coconut alcohols is reacted with epichlorhydrin in the presence of SnCl4 yielding alkyl chloro glyceryl ethers, containing 14 moles per cent. of the diglyceryl ether, which are reacted with 2,5% aqueous NaOH and the product is worked up by either adding water and settling or separating the ether phase and water washing it; the product containing 3.2% combined chlorine is sulphonated as above with aqueous sodium sulphite/bisulphite solution at pH 5-8.  Other fatty alcohols specified include those derived from palm and marine oils and tallow. Comparative experiments are described wherein epoxidation is effected with aqueous alkali of concentrations above and below the values above stipulated and wherein sulphonation is effected with sodium sulphite in the absence of bisulphite.  The sulphonates may be used in detergent compositions (see Group III).ALSO:Detergent compositions comprise the mixture of alkyl or alkenyl glyceryl and polyglyceryl ether sulphonates prepared by reacting epichlorhydrin with a saturated or ethylenically unsaturated fatty alcohol containing 10 to 20 carbon atoms, treating the resulting alkyl or alkenyl glyceryl chloroethers with aqueous alkali metal hydroxide solution to epoxidise the product, separating a substantially inorganic salt-free epoxidised ether phase and sulphonating the epoxidised ether with an aqueous solution of alkali metal sulphite and bisulphite, all in specified manner (see Group IV(b)).  The mixture of sulphonates contains 10-30% mole of alkyl (or alkenyl) diglyceryl ether sulphonate. The sulphonates may be used in the alkali metal salt form or after appropriate reactions, in other salt form e.g. as the calcium, magnesium, ammonium or alkylolamine salts.  In Example II, the mixture of sodium ether sulphonates prepared as above from a middle cut of coconut oil alcohols is converted into a detergent composition in bar form comprising also soap and water, and into a liquid detergent comprising also alkyl benzene sulphonate, potassium pyrophosphate, silicate solids, water and amounts of solvent, builders, solubilising agents, colour and perfume. Specification 802,325 is referred to.