Patent GB-450579-A (GB)
Title: Process for the preparation of wetting, emulsifying, dispersing and cleansing agents
Filed: 1935-04-29
Abstract: A ketone of the formula RCOR or RCOR<1>, where R is an aliphatic chain of more than eight carbon atoms and R<1> is an aliphatic chain of less than five carbon atoms, is halogenated and then subjected to a reaction whereby the halogen is replaced by a solubilizing group or by a chain of less than five carbon atoms containing a solubilizing group; the solubilizing group is one of the following: a free or neutralized sulphuric or phosphoric acid ester, sulphonic or thiosulphuric group, a carboxylic group neutralized with an alkali metal or ammonium, a neutralized primary, secondary, tertiary or quaternary amino group, or a radicle of a polyglycerol or polyglycol derived from more than two molecules of glycerol or glycol.  The reaction may be effected in more than one stage.  The products are useful as wetting, emulsifying and cleansing agents.  The ketones used as starting materials are prepared from animal or vegetable fats or oils, e.g. by heating the corresponding acids with iron filings or by passing a mixture of the acids with a lower aliphatic acid over a ketonizing catalyst.  In examples of the preparation of halogenated ketones, (1) diheptadecyl ketone, prepared in known manner from stearic acid, is monochlorinated in carbon tetrachloride solution; (2) a ketone of the formula RCOCH3, where R is a saturated aliphatic chain of about thirteen carbon atoms, (prepared in known manner from acetic acid and the acid of coconut oil), is monobrominated in carbon tetrachloride solution. In examples of the preparation of products containing a solubilizing group; (3) the product of example 2 is heated with aqueous sodium sulphite; (4) the product of example 2 is heated with alcoholic potash and the hydroxyketone obtained is treated with sulphuric or phosphoric acid; (5) the product of example 2 is condensed with the monosodium compound of glycerol, and the product is esterified with sulphuric acid; (6) the product of example 2 is heated with sodium aminomethanesulphonate; (7) the product of example 2 is treated in benzene solution with gaseous ammonia; (8) the product of example 1 is heated with alcoholic potash and then esterified with sulphuric acid; (9) the product of example 2 is converted into a nitrile by reaction with potassium cyanide, and the nitrile is saponified with caustic potash. Reference is made also to the reaction of the halogenated ketones with sodium thiosulphate, the sodium compound of a polyglycerol, taurine, asym, dimethylethylenediamine, and ethanolamine; when ethanolamine is used, the product is afterwards sulphonated. Specification 360,493 is referred to.ALSO:A ketone of the formula RCOR or RCOR<1>, where R is an aliphatic chain of more than eight carbon atoms and R<1> is an aliphatic chain of less than five carbon atoms, is halogenated and then subjected to a reaction whereby the halogen is replaced by a solubilizing group or by a chain of less than five carbon atoms containing a solubilizing group; the solubilizing group is one of the following:--a free or neutralized sulphuric or phosphoric acid ester, sulphonic or thiosulphuric group, a carboxylic group neutralized with an alkali metal or ammonium, a neutralized primary, secondary, tertiary or quaternary amino group, or a radicle of a polyglycerol or polyglycol derived from more than two molecules of glycerol or glycol.  The reaction may be effected in more than one stage.  The products are useful as emulsifying agents.  In examples of the preparation of halogenated ketones, (1) diheptadecyl ketone is monochlorinated in carbon tetrachloride solution; (2) a ketone of the formula RCOCH3, where R is a saturated aliphatic chain of about thirteen carbon atoms derived from the acids of coconut oil, is monobrominated in carbon tetrachloride solution.  In examples of the preparation of products containing a solubilizing group, (3) the product of example 2 is heated with aqueous sodium sulphite; (4) the product of example 2 is heated with alcoholic potash and the hydroxyketone obtained is treated with sulphuric or phosphoric acid; (5) the product of example 2 is condensed with the monosodium compound of glycerol, and the product is esterified with sulphuric acid; (6) the product of example 2 is heated with sodium aminomethanesulphonate; (7) the product of example 2 is treated in benzene solution with gaseous ammonia; (8) the product of example 1 is heated with alcoholic potash and then esterified with sulphuric acid (9) the product of example 2 is converted into a nitrile by reaction with potassium cyanide and the nitrile is saponified with caustic potash.  Reference is made also to the reaction of the halogenated ketones with sodium thiosulphate, the sodium compound of a polyglycerol, taurine, asym. dimethylethylenediamine and ethanolamine; when ethanolamine is used, the product is afterwards sulphonated.  Specification 360,493 is referred to.