Patent GB-822901-A (GB)
Title: Sulphonates containing peroxide groups and a process for their preparation
IPC: C08F4/32
Filed: 1955-12-20
Abstract: The invention comprises sulphonates containing peroxy groups and having one of the following general formulae: (1) Kat-O-O-Z-SO3-Kat1. (2) X-O-O-Z-SO3-Kat; and (3) Kat1-SO3-Z1-O-O-Z-SO3-Kat, wherein Z and Z1 represent the hydrocarbon residues of sultones of the general formulae <FORM:0822901/IV (a)/1> wherein the carbon atom directly bound to the oxygen atom is a primary or secondary aliphatic carbon atom and Z and Z1 each contain not more than 20 carbon atoms and preferably have 3-7 carbons, Kat and Kat1 represent cations and X, which is linked to the peroxy group via a primary secondary or tertiary non-aromatic carbon atom, represents a substituted or unsubstituted hydrocarbon radical containing 1-30 carbon atoms which may be interrupted in its acyclic or cyclic chain by one or more hetero atoms, for example oxygen or sulphur atoms, and may be linked via a peroxide group to a substituted or unsubstituted hydrocarbon radical.  The sulphonates having the first general formula are prepared by reacting the sultone with hydrogen peroxide in the presence of an acid-binding substance using a molar ratio of sultone to hydrogen peroxide of less than 2, and if desired, acidifying the resulting peroxy-sulphonic acid salt to liberate the free acid.  The compounds having the third formula are prepared by reacting hydrogen peroxide with an appropriate sultone or mixture of such sultones in the presence of an acid binding agent using a molar ratio of sultone to hydrogen peroxide of at least 2 and, if desired, acidifying to liberate the free acid of the resulting product.  The compounds of the second general formula are prepared by reacting the sultone with the appropriate organic hydroperoxide in the presence of an acid binding agent, and acidifying the product if the free sulphonic acid is desired.  The sultones specified include alkane sultones, toluyl sultone and sultones of cycloaliphatic compounds.  The organic hydroperoxides may be saturated or unsaturated straight or branched chain aliphatic, cycloaliphatic, aromatic, aromatic-aliphatic or heterocyclic compounds and may contain peroxy, hydroxyl, mercapto, ether, thioether, carboxylic acid or carboxylic acid ester groups and halogen atoms; numerous examples are given of all types.  The acid-binding agents are preferably alkali metal or alkaline earth metal compounds; a mixture of the agents may be used.  If desired, the acid-binding agent may be provided by using the peroxide reagent in salt form.  The reaction is preferably effected in water or an organic solvent.  The reagents and solvents may be brought together in any order. Stabilizers may be added to the hydroperoxides before the reaction and several are specified.  Reaction temperatures may range from 5 DEG  up to 150 DEG  C.  The peroxy sulphonates may be isolated by filtration, if necessary after concentration.  The products, which may contain water of crystallization, can be converted into the free sulphonic acids by treatment with a strong acid or a hydrogen ion exchanger.  The products may be used to provide free radicals as initiators of chain reactions.