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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C309-00
filingDate 1964-04-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1967-02-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1059984-A
titleOfInvention Process for producing metal salts of 2-hydroxyalkane sulfonic acids
abstract Metal salts of 2-hydroxyalkane sulphonic acids of the formula HOCHR-CHR1SO3M, wherein R and R1 each represent a hydrogen atom or an alkyl radical and M represents an alkali metal, alkaline earth metal or Ag, Zn, Mn or Al cation are obtained by reacting ammonia or a volatile amine of the formula R2N(R3)R4, wherein R2 R3 and R4 are as hereinafter defined with sulphur dioxide in the presence of water, to form a bisulphite which is then reacted with an alkylene oxide to give the salt of the nitrogen base of 2-hydroxyalkane sulphonate of the formula <FORM:1059984/C2/1> wherein R2, R3 and R4 each represent hydrogen or an alkyl, alkenyl, alicyclic, or aryl or any two of R2, R3 and R4 form with the N atom a heterocyclic radical; which is then reacted with a metal hydroxide or oxide selected from the alkali metals, alkaline earth metals or Ag, Zn, Mn or Al in the presence of water and the nitrogen base removed by vaporization. The above process may be carried out continuously, the nitrogen base being recovered from the process and reused. Suitable nitrogen bases include methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, dipropylamine, tripropylamine, butylamine, dibutylamine, tributylamine, amylamine, diamylamine, hexylamine, cyclohexylamine, octylamine, dodecylamine, aniline, methyl aniline, their isomers and their mixtures, and also heterocyclic amines of the formula <FORM:1059984/C2/2> where X represents oxygen, sulphur, nitrogen or a methylene radical, m represents 2 or 3 and n represents an integer of 1 to 3. Specific examples include morpholine and piperidine. Unsaturated heterocyclic compounds such as pyridine and quinoline may also be used. Specified alkylene oxides include ethylene oxide, propylene oxide, butylene oxide, their isomers and their mixtures. Salts of those metals which on hydrolysis yield hydroxides may be used provided objectionable anions are not produced, e.g. aluminium isopropylate. Examples are given and an example is also given in which calcium isethionate prepared according to the process is reacted with tallow acid in the presence of hypophosphorus acid to give the tallow ester of calcium isethionate.
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