Patent GB-669304-A (GB)
Title: Improvements in or relating to tri-(substituted mercapto)-s-antimonious acids and intermediates therefor
IPC: G06M1/14
Filed: 1948-01-23
Abstract: Tri - (substituted mercapto - S - antimonous acids of the general formula <FORM:0669304/IV (b)/1> wherein R1, R2 and R3 may be the same or different and represent hydrocarbon groups each containing from 6 to 16 carbon atoms, are prepared by reacting antimony trobromide or trichloride with mercaptans or their alkaline earth metal mercaptides containing the groups R1, R2 and R3 linked by -CH2CH2- t the mercapto sulphur atoms. The groups R1, R2 and R3 may contain from 8 to 12 carbon atoms, e.g. 10 carbon atoms.  The reactants may be employed in the proportion of one gram atom of antimony to three mols. of the mercapto compound.  The reaction may be effected by dissolving each reactant in an inert solvent, the solvents being miscible, and mixing the solutions.  The hydrocarbon groups R1, R2 and R3 may be normal alkyl groups or o -cyclic alkyl groups.  The expression "o -cyclic alkyl" refers to hydrocarbon groups having 8 to 18 carbon atoms of the formula Y-R-, where Y is a cyclic group and R is an alkylene chain containing from 2 to 10 carbon atoms.  The alkylene chain may contain up to 3 carbon atoms and the group Y may be partially or totally saturated.  In the examples tri-(n-dodecyl-mercapto)-, tri-[b -(naphthyl-1)-ethylmercapto]-, tri-[b -(cyclohexyl)-ethylmercapto]-, tri - [o -cyclohexylamylmercapto]-, tri-[o -(b -tetralyl)-butylmercapto]-, and tri-[o -decalylbutylmercapto]-S-antimonous acids are prepared. Compounds of the formula (R-S)3Sb, where R is n-octyl, n-decyl, n-undecyl, n-tetradecyl, n-hexadecyl, n-octadecyl and b -phenylethyl are also mentioned.  o -Cyclic alkyl mercaptans of the formula Y-R-SH, where the grouping Y-R- is the  -cyclic alkyl group defined above, are prepared by hydrolysing with a dilute solution of an alkaline hydroxide:-  o -Cyclic alkyl isothiuronium halides of the formula <FORM:0669304/IV (b)/2> where Y-R- is the o -cyclic alkyl group defined above and Hlg is chlorine, bromine or iodine, which may be prepared by reacting with thiourea o -cyclic alkyl halides of the formula Y-R-Hlg, wherein Y-R- is the o -cyclic alkyl group defined above, which may be prepared by treating with a phosphorus halide or a hydrohalogen acid, the halide being chlorine, bromine or iodine o -cyclic alkyl alcohols of the formula Y-R-OH, wherein Y-R- is the o -cyclic alkyl group defined above, which may be prepared by hydrogenating an ester of an acid of the general formula Y-R1-COOH, wherein Y is a cyclic hydrocarbon group, R1 is an alkylene chain containing 1 to 9 carbon atoms and Y and R1 together contain 7 to 17 carbon atoms.  In the examples, o -cyclohexyl-amyl-, o -(b -tetralyl)-butyl-, and o -decalylbutyl mercaptans, isothiuronium bromides and alcohols are prepared.  The Specification as open to inspection under Sect. 91 refers to the preparation of compounds of the general formula <FORM:0669304/IV (b)/3> wherein R1, R2 and R3 are the same or different organic radicals containing at least 8 carbon atoms by the method employed to prepare the above S-antimonous acids. Compounds in which R1, R2 and R3 represent the b -(2-pyridyl)-ethyl and the b -(p-diisobutyl phenoxyethoxy)-ethyl radicals are mentioned. This subject-matter does not appear in the Specification as accepted.