Patent GB-359001-A (GB)
Title: Improvements in the manufacture and production of valuable organic nitrogen compounds
IPC: C07F9/08
Filed: 1930-07-07
Abstract: Halogenated aliphatic hydrocarbons containing at least ten carbon atoms in the molecule are condensed with primary or secondary amines or fatty acid amides.  Suitable halogenated hydrocarbons may be obtained by halogenating appropriate petroleum fractions, products from the liquefaction of coal, or brown coal tar oils.  The amines used may be aliphatic, aromatic, or hydroaromatic, and may contain hydroxyl groups.  The condensation may be effected in the presence or absence of organic solvents or diluents, a number of which are specified, and at atmospheric or raised pressure; a condensing agent may be present, e.g. copper or a copper salt, aluminium chloride, zinc chloride, soda or caustic soda, or sodium acetate.  The condensation products may be treated with organic or inorganic non-oxidizing acids, including sulphuric acid, to yield salts, esters or sulphonic acids.  The products obtainable by any of the methods described above have emulsifying properties.  They may be used in the preparation of oil emulsions for spinning and for greasing leather, as assistants in the production of drilling greases or oils, and in the preparation of finely divided pigments.  According to the examples, (1) paraffin wax is chlorinated, the product is heated with ethanolamine, and the resulting oil is treated with chlorsulphonic acid to produce an acid sulphuric ester; (2) brown coal tar oil is chlorinated, and the product is heated under pressure with n-butylamine in the presence of a little copper; the base so obtained is useful as a dispersing agent for dyestuff printing pastes; the salts of the base have saponaceous properties; di-n-butylamine or ethylene diamine may be used instead of n-butylamine; (3) a petroleum fraction boiling at 150-300 DEG  C. is chlorinated, and the product is heated with p-aminophenol in the presence of a little copper; the product has dispersing properties, and yields on sulphonation a product useful as a wetting agent; p-aminophenol sulphonic acids or 1,2-, 1,7-, or 2,7-aminonaphthol may be used in the initial condensation, instead of p-aminophenol; (4) paraffin wax is chlorinated, and the product is heated with stearic acid amide; the resulting amide may be sulphonated with fuming sulphuric acid. Reference is made to the condensation of methylamine, dimethylamine, aniline, cyclohexylamine, and chlorocyclohexylamine with the halogenated hydrocarbons, and to the treatment of the condensation products with phosphoric, oxalic, acetic, or lactic acid. Specifications 264,860, [Class 1 (i), Chemical processes &c.], 302,984, and 339,962, [both in Class 2 (iii), Dyes &c.], are referred to.ALSO:Halogenated aliphatic hydrocarbons containing at least ten carbon atoms in the molecule are condensed with primary or secondary amines or fatty acid amides.  Suitable halogenated hydrocarbons may be obtained by halogenating appropriate petroleum fractions, products from the liquefaction of coal, or brown coal tar oils.  The amines used may be aliphatic, aromatic, or hydroaromatic, and may contain hydroxyl groups.  The condensation may be effected in the presence or absence of organic solvents or diluents, a number of which are specified, and at atmospheric or raised pressure; a condensing agent may be present, e.g. copper or a copper salt, aluminium chloride, zinc chloride, soda or caustic soda, or sodium acetate.  The condensation products may be treated with organic or inorganic non-oxidizing acids, including sulphuric acid, to yield salts, esters, or sulphonic acids.  The products obtainable by any of the methods described above have wetting, washing, tanning, emulsifying and like properties.  They may be used in the preparation of oil emulsions for spinning and for greasing leather, as assistants in the production of drilling greases or oils, as substitutes for fats and oils in industrial processes, as levelling agents in dyeing, and in the preparation of finely divided pigments. According to the examples, (1) paraffin wax is chlorinated, the product is heated with ethanolamine, and the resulting oil is treated with chlorsulphonic acid to produce an acid sulphuric ester having cleansing and wetting properties; (2) brown coal tar oil is chlorinated, and the product is heated under pressure with n-butylamine in the presence of a little copper; the base so obtained is useful as a softening agent for leather and as a dispersing agent for dyestuff printing pastes; the salts of the base have saponaceous properties; di-n-butylamine or ethylene diamine may be used instead of n-butylamine; (3) a petroleum fraction boiling at 150-300 DEG  C. is chlorinated, and the product is heated with p-aminophenol in the presence of a little copper; the product has dispersing properties, and yields on sulphonation a product useful as a wetting agent; p-aminophenol sulphonic acids or 1,2-, 1,7-, or 2,7-aminonaphthol may be used in the initial condensation, instead of p-aminophenol; (4) paraffin wax is chlorinated, and the product is heated with stearic acid amide; the resulting amide may be sulphonated with fuming sulphuric acid. Reference is made to the condensation of methylamine, dimethylamine, aniline, cyclohexylamine, and chlorocyclohexylamine with the halogenated hydrocarbons, and to the treatment of the condensation products with phosphoric, oxalic, acetic, or lactic acid. Specifications 264,860, 302,984, and 339,962, [all in Class 2 (iii), Dyes &c.], are referred to.