Patent GB-1040178-A (GB)
Title: Process for the preparation of surface-active ether sulphonates
IPC: C07C309/03
Filed: 1963-05-27
Abstract: The invention comprises a detergent composition, a process for treating articles with a detergent or cleansing agent, and the articles treated by this process, the detergent composition comprising a surface-active compound of formula <FORM:1040178/C4-C5/1> in which R1 and R2 are alkyl groups, R3 is hydrogen or an alkyl group, R1, R2 and R3 together containing 7-19 carbon atoms, R4 is a bivalent straight or branched chain of carbon atoms which may be interrupted by one or more oxygen atoms, but which does not contain a hydroxyl group, the sulphur and oxygen atoms vicinal to R4 being attached to carbon atoms of the bivalent group R4, and Me represents a cation.  The compositions may also comprise other surface-active compounds, "builders" such as alkali metal pyrophosphates or polyphosphates, silicates, carbonates, sulphates, borates, sodium carboxymethylcellulose and other soluble derivatives of cellulose or starch, bleaching agents such as persulphates, perborates, percarbonates, "optic bleaching agents," foam promoters and foam stabilizers.ALSO:Surface active compounds of Formula I <FORM:1040178/C2/1> in which R1 and R2 are alkyl groups, R3 is hydrogen or an alkyl group, R1, R2 and R3 together containing 7-19 carbon atoms, R4 is a bivalent straight or branched chain of carbon atoms which may be interrupted by one or more oxygen atoms, but which does not contain a hydroxy group, the sulphur and oxygen atoms vicinal to R4 being attached to carbon atoms of the bivalent group R4, and Me represents a cation, are prepared by reacting a halohydrin of formula HO-R4-X, where X is a halogen atom, with an olefinic hydrocarbon which provides the group <FORM:1040178/C2/2> by dissolution of a double bond between the central carbon atom and any one of the groups which upon addition of a hydrogen atom becomes R1, R2 or R3, and replacing the halogen atom in the compound obtained of Formula III <FORM:1040178/C2/3> with a sulphonate group.  The halogen atom X may be replaced by a sulphonate group by reacting a compound of Formula III with a sulphite or bisulphite, preferably an alkali metal sulphite, preferably using excess sulphite or bisulphite reactant, in a suitable medium such as water or otherwise a liquid in which both reactants are to some extent soluble, at temperatures within the range 100-200 DEG  C.  Metabisulphites in a solvent containing a substance, such as water, whereby they are converted to bisulphites, may also be used.  The sulphites or bisulphites may also be prepared in situ, e.g. from an alkali metal hydroxide and sulphur dioxide.  The reaction between the olefinic compound and the halohydrin is advantageously carried out in the presence of acid catalysts, preferably BF3 and sulphuric acid, advantageously in the presence of water, when the reaction takes place at comparatively low temperatures. Strong acids, aromatic sulphonic acids, and Lewis acids are also suitable.  The reaction is generally conducted at elevated temperature, e.g. 50-200 DEG  C., under pressure to prevent boiling, advantageously in a solvent which preferably has a polar character. It is not necessary to start from pure olefins, mixtures of olefins having 8-18 carbon atoms, e.g. obtained by cracking paraffin hydrocarbons, may be used.  The sec.-dodecyl monoether of glycol is obtained as by-product in the reaction of 1 mol. sec.-dodecyl-beta-chloroethyl-ether with 5 mols. sodium sulphite used as 20% by weight aqueous solution.