Patent GB-1012944-A (GB)
Title: ª‰-hydroxy-alkane-ª‡-sulphonic anhydrides and secondary products thereof, and a process for their manufacture
IPC: C07C303/02
Filed: 1961-12-11
Abstract: The invention comprises (a) b -hydroxy-alkane - a  - sulphonic anhydrides containing as structural units n groupings of the formula <FORM:1012944/C3/1> and m groupings of the formula <FORM:1012944/C3/2> wherein R1, R2, R3 and R4 represent hydrogen or identical or different hydrocarbon radicals which can be linked to each other and be substituted by chlorine atoms or nitro, cyano or alkoxy groups, n is an integer of 1 to 100, and m is an integer greater than n and smaller than 2n; (b) compounds of the formula (C2H4)n(SO3)m, wherein n is an integer of 3 to 100 and m is equal to n; and (c) a process for the preparation of b -hydroxy-alkane-a -sulphonic anhydrides containing as structural units n groupings of the formula <FORM:1012944/C3/3> and m groupings of the formula <FORM:1012944/C3/4> wherein R1, R2, R3 and R4 represent hydrogen or identical or different hydrocarbon radicals which can be linked to each other and which may contain substituents that are inert under the reaction conditions, wherein an olefine or olefines of the formula <FORM:1012944/C3/5> and being free of conjugated or cumulative double bonds is or are reacted with sulphur trioxide either (a) by first reacting the olefine with sulphur trioxide to form the corresponding carbyl sulphate and then eliminating one molecular proportion of sulphur trioxide therefrom or (b) by reacting the olefine with sulphur trioxide such that the molar concentration of sulphur trioxide in the reaction mixture does not exceed 10%.  The sulphur trioxide elimintion of (a) above is effected either thermally and the separated sulphur trioxide removed from the reaction zone, preferably under reduced pressure, or by reacting the carbyl sulphate at an elevated temperature, preferably 30 DEG  to 150 DEG C., either with the olefine used for making said carbyl sulphate or with another olefine of the above general formula.  It is preferred to use the sulphur trioxide in the direct reaction (b) above principally or, more advantageously, wholly in the monomeric form.ALSO:The invention comprises (a) b -hydroxy-alkane-a -sulphonic anhydrides containing as structural units n groupings of the formula <FORM:1012944/C2/1> and m groupings of the formula <FORM:1012944/C2/2> wherein R1, R2, R3 and R4 represent hydrogen or identical or different hydrocarbon radicals which can be linked to each other and be substituted by chlorine atoms or nitro, cyano or alkoxy groups, n is an integer of 1 to 100, and m is an integer greater than n and smaller than 2n; (b) compounds of the formula (C2H4)n(SO3)m, wherein n is an integer of 3 to 100 and m is equal to n; and (c) a process for the preparation of b -hydroxy-alkane-a -sulphonic anhydrides containing as structural units n groupings of the formula <FORM:1012944/C2/3> and m groupings of the formula <FORM:1012944/C2/4> wherein R1, R2, R3 and R4 represent hydrogen or identical or different hydrocarbon radicals which can be linked to each other and which may contain substituents that are inert under the reaction conditions, and b -substituted-a -sulphonic acids and a :b -unsaturated sulphonic acids of said anhydrides or salts thereof, wherein an olefine or olefines of the formula <FORM:1012944/C2/5> and being free of conjugated or cumulative double bonds is or are reacted with sulphur trioxide either (a) by first reacting the olefine with sulphur trioxide to form the corresponding carbyl sulphate and then eliminating one molecular proportion of sulphur trioxide therefrom, or (b) by reacting the olefine with sulphur trioxide such that the molar concentration of sulphur trioxide in the reaction mixture does not exceed 10%, and, if desired, converting the b -hydroxy-alkane-a -sulphonic anhydride so obtained by reaction with a polar or polarizable compound to form a b -substituted-a -sulphonic acid, an a :b -unsaturated sulphonic acid or a salt of either of said acids. The sulphur trioxide elimination of (a) above is effected either thermally and the separated sulphur trioxide removed from the reaction zone, preferably under reduced pressure, or by reacting the carbyl sulphate at an elevated temperature, preferably 30 DEG  to 150 DEG  C., either with the olefine used for making said carbyl sulphate or with another olefine of the above general formula.  It is preferred to use the sulphur trioxide in the direct reaction (b) above principally or, more advantageously, wholly in the monomeric form.  a :b -Unsaturated sulphonic acids may be obtained by treating a b -hydroxy-alkane-a -sulphonic anhydride of the formula given in (c) above and which contains at least one hydrogen atom at the a -carbon atom with a solution of a strong alkali or of a substance yielding a strongly basic solution in water.  Specified b  - substituted - a  - sulphonic acids obtained by reacting the anhydrides of the formula stated in (c) above with polar or polarizable compounds are those having hydroxy, amino, monomethylamino, monocyclohexylamino, diphenylamino, chloro, cyano, phenoxy, acetoxy, ethylthio and mercapto groups as the b -substituent.  The betaines of b -pyridinium-alkane-a -sulphonic acids may be prepared by reacting the anhydrides of the formula stated in (c) above with pyridine.