Patent GB-416379-A (GB)
Title: Improvements in the manufacture and production of substances suitable as wetting, cleansing, dispersing, softening and like agents
Filed: 1933-03-06
Abstract: Sulphonic acids stated to be useful as dispersing agents are prepared by condensing an aliphatic olefine hydrocarbon or an aliphatic halogenated hydrocarbon containing more than eight carbon atoms in the molecule with an aromatic hydrocarbon in the presence of a surface active or an acid condensing agent and sulphonating during or after the condensation.  The olefines may be prepared by catalytic dehydrogenation of saturated hydrocarbons, by cracking processes, by removing hydrogen halide from halogenated hydrocarbons and by removing water from the higher alcohols.  As examples of the latter are mentioned octyl, nonyl, decyl, dodecyl, myristyl, cetyl, octodecyl and oleyl alcohols, montanol, octodecandiol and the alcohols derived from palm oil, soya bean oil, olive oil, castor oil, train oil and tallow.  The following hydrocarbons which may be treated so as to yield olefines are specified: liquid, semi solid or solid paraffin hydrocarbons obtained by hydrogenation of coals, tars or mineral oils or by distilling shale oils or tars, hydrocarbons obtained by the reduction of carbon oxides, polymerized olefines, petroleum jelly, ceresine oxokerite, montan wax and lubricating oils. A mixture of aromatic and aliphatic hydrocarbons may be submitted to halogenation and subsequent removal of hydrogen halide.  Toluene, xylene, cumene, naphthalene, diphenyl, acenaphthene, phenanthrene, anthracene, methylnaphthalene, ethylnaphthalene and tetrahydronaphthalene are specified aromatic hydrocarbons. Edeleanu extracts which contain aromatic and unsaturated aliphatic hydrocarbons may be used.  The sulphonated products may be used as such or in the form of their salts with ammonia, methyl or ethylamine, pyridine and piperidine or in association with soaps, turkey red oils, sulphonic acids, sulphuric esters, glue, salts and perborates.  In examples: (1) mineral oil fractions are chlorinated and then condensed with benzene, xylene, naphthalene and methylated naphthalenes in the presence of aluminium or zinc chloride; the products, sometimes after purification by distillation are sulphonated with sulphuric monohydrate, oleum or chlorsulphonic acid; (2) octodecylene is condensed with toluene in the presence of aluminium chloride, whereupon the product is sulphonated; (3) a mixture of olefines obtained by cracking slack wax is condensed with naphthalene and xylene and is then sulphonated; (4) the alcohols derived from coconut or palm kernel fat are treated with phosphoric acid in vacuo and the resulting olefines condensed with toluene and xylene and finally sulphonated.  Specifications 246,867, 263,873, 277,277, and 322,005, [all in Class 2 (iii)], are referred to.ALSO:Sulphonic acids stated to be useful as wetting, cleansing, dispersing, softening, and like agents are prepared by condensing an aliphatic olefine hydrocarbon or an aliphatic halogenated hydrocarbon containing more than eight carbon atoms in the molecule with an aromatic hydrocarbon in the presence of a surface active or an acid condensing agent and sulphonating during or after the condensation. Friedel - Crafts catalysts, sulphuric acid, tonsil and bleaching earths are mentioned as examples of the condensing agents which may be employed.  The olefines may be prepared by catalytic dehydrogenation of saturated hydrocarbons, by cracking processes, by removing hydrogen halide from halogenated hydrocarbons and by removing water from the higher alcohols.  As examples of the latter are mentioned, octyl, nonyl, decyl, dodecyl, myristyl, cetyl, octodecyl and oleyl alcohols, montanol, octodecandiol and the alcohols derived from palm oil, soya bean oil, olive oil, castor oil, train oil and tallow.  The removal of water from the alcohols may be effected by means of phosphoric acid, active carbon impregnated with phosphoric acid, phosphorus pentoxide, aluminium oxide or bauxite, and the removal of hydrogen halide from the halogenated hydrocarbons may be effected by means of aluminium oxide, bauxite, zinc or barium chlorides.  The following hydrocarbons which may be treated so as to yield olefines are specified: liquid, semi-solid or solid paraffin hydrocarbons obtained by hydrogenation of coals, tars or mineral oils or by distilling shale oils or tars, hydrocarbons obtained by the reduction of carbon oxides, polymerized olefines, petroleum jelly, ceresine, ozokerite, montan wax and lubricating oils.  Any aliphatic hydrocarbons containing more than eight carbon atoms in the molecule, or mixtures thereof may be used for the preparation of the halogenated hydrocarbons used as starting material for the manufacture of the olefines, and a mixture of the aromatic hydrocarbons with the aliphatic hydrocarbons may also be submitted to halogenation and subsequent removal of hydrogen halide.  Toluene, xylene, cumene, naphthalene, diphenyl, acenaphthene, phenanthrene, anthracene, methylnaphthalene, ethylnaphthalene and tetrahydronaphthalene are specified aromatic hydrocarbons.  Edeleanu extracts which contain aromatic and unsaturated aliphatic hydrocarbons may be used.  The sulphonated products may be used as such or in the form of their salts with ammonia, methyl or ethylamine, pyridine and piperidine or in association with soaps, turkey red oils, sulphonic acids, sulphuric esters, glue, salts and perborates.  In examples: (1) mineral oil fractions are chlorinated and then condensed with benzene, xylene, naphthalene and methylated naphthalenes in the presence of aluminium or zinc chloride; the products, sometimes after purification by distillation are sulphonated with sulphuric monohydrate, oleum or chlorsulphonic acid; (2) octodecylene is prepared (a) from octodecane by chlorination and distillation over barium chloride or (b) from octodecylalcohol by treatment with active carbon impregnated with phosphoric acid and is condensed with toluene in the presence of aluminium chloride, whereupon the product is sulphonated; (3) a mixture of olefines obtained by cracking slack wax is condensed with naphthalene and xylene and is then sulphonated; (4) the alcohols derived from coco-nut or palm kernel fat are treated with phosphoric acid in vacuo and the resulting olefines condensed with toluene and xylene and finally sulphonated.  Specifications 246,867, 263,873, 277,277, and 322,005, [all in Class 2 (iii)], are referred to.