Patent GB-498008-A (GB)
Title: Improvements in the manufacture and production of capillary-active agents
IPC: C07C309/20
Filed: 1937-06-25
Abstract: Capillary-active agents are made by sulphonating aliphatic hydrocarbons containing in the molecule at least 15 carbon atoms and a halogen atom and at least one double linkage which is situated at the middle of the carbon chain or between the middle carbon atom or atoms and adjacent carbon atoms, or by halogenating sulphonation products of aliphatic hydrocarbons of the said nature free from halogen.  Suitable initial substances are those obtained by splitting off hydrogen halide from hydrocarbons containing at least two halogen atoms, one of which is at or near the middle of the carbon chain, or those obtained by treating high-molecular unsaturated alcohols with thionyl chloride, any hydrogen halide which adds on to the double linkage being split off again by saponifying agents.  The sulphonation may be carried out using concentrated sulphuric acid, sulphuric acid mono-hydrate, chlorsulphonic acid or sulphuric anhydride, if necessary in presence of solvents such as trichlorethylene or carbon tetrachloride and/or substances such as ether, phosphorus pentoxide, acetic anhydride or glacial acetic acid, or by using formaldehyde and sulphuric acid, thioethane sulphonic acid, ethionic acid or acetaldehyde disulphonic acid.  When employing anhydrides or chloride of inorganic or organic acid such as phosphorus pentoxide, acetyl chloride, or acetic anhydride, products containing phosphoric, acetic, or sulphuric ester groups may be obtained.  Unhalogenated sulphonated hydrocarbons suitable as initial materials may be obtained by sulphonation of dimers of olefines obtained by splitting off water from primary alcohols, such as those in the higher-boiling bye-products of the methanol synthesis, or obtained by cracking high-molecular aliphatic hydrocarbons, or by sulphonation of olefines obtained by isomerisation of high-molecular olefines having terminal double bonds, or by sulphonation of products obtained by converting aliphatic carboxylic acids of at least 8 carbon atoms into ketones, reducing these ketones to secondary alcohols, and splitting off water from the latter.  Halogenation may be carried out while irradiating and/or in presence of iodine.  In working up the sulphonation products they may be converted to salts with alkalies, ammonia or amines and organic bases such as dimethylamine, triethanolamine, or pyridine.  The products are wetting agents, and may be used for the treatment of textiles alone or with substances such as common salt, Glauber's salt, waterglass, sodium metaphosphate, solvents such as carbon tetrachloride, trichlorethylene, cyclohexanol, or tetrahydronaphthalene, or bleaching agents such as perborates or hydrogen peroxide.  In examples, (1) 1-chloro-9,10-octodecylene is treated with sulphuric acid monohydrate in acetic anhydride; (2) a mixture of olefines (obtained by ketonizing a carboxylic acid mixture consisting mainly of carboxylic acids of 8-9 carbon atoms recovered in the distillation of the carboxylic acids from the oxidation of high-molecular paraffins, reducing the ketones to secondary alcohols and splitting off water therefrom) is treated with sulphuric acid monohydrate in acetic anhydride, followed by chlorination of the product while irradiating with light.  Specifications 344,829 and 448,659 are referred to.  1-Chloro-9.10-octodecylene is prepared by treating oleyl alcohol with thionyl chloride.