Patent GB-466635-A (GB)
Title: Manufacture of water-soluble derivatives of the indole series
IPC: C07D209/08
Filed: 1936-07-03
Abstract: Products stated to have wetting, emulsifying, foaming, softening and washing properties are prepared by sulphonating, under conditions whereby coloured by products are avoided, indols containing an aliphatic or alicyclic substituent with more than five carbon atoms in positions 1, 2 or 3.  Derivatives in which p  (a) the benzene nucleus contains any substituent, (b) the heterocyclic nucleus is hydrogenated and (c) the remaining free positions 1, 2 or 3 contain alkyl, aralkyl or aryl groups give similar products on sulphonation. The use of the products for emulsifying lime soaps is mentioned.  In examples, the following indols or indol derivatives are sulphonated: 2-heptadecenylindol, the indols obtained from palm nut fatty acid o-toluidide and cod oil fatty acid o-toluidide, and dihydro indol obtained by reducing the indol from palm nut fatty acid o-toluidide. Indols used as starting materials may be made by acylating with a carboxylic acid an aromatic o-alkyl amine, whose amino group may contain one alkyl, aralkyl or aryl group, and subjecting the product to ring closure.  Aromatic amine derivatives containing alkoxy, cyano or halogen in the benzene nucleus may be used.  In an example, palm nut fatty acid o-toluidide is treated with sodium and ethylalcohol and after distillation of some of the alcohol is subjected to fusion to give the indol.  Indols derived from o-toluidine, o-aminoethylbenzene or m or p-xylidines which are alkylated or cycloalkylated at the nitrogen by means of residues of dodecylalcohol, olein alcohol, naphthene alcohol, terpene alcohol or cyclohexanol and are acylated by means of formic, acetic, phenylacetic or phenoxy-acetic acid are mentioned.  The use, for the acylation of aromatic amines of stearic, oleic, soya, naphthenic, campholic, fencholic and resin acids in order to produce indols having a higher aliphatic or cycloaliphatic residue in the 2-position is referred to.  Specification 303,467, [Class 2 (iii)], is referred to.ALSO:Products stated to have emulsifying properties are prepared by sulphonating, under conditions whereby coloured by-products are avoided, indols containing an aliphatic or alicyclic substituent with more than five carbon atoms in positions 1, 2 or 3. Derivatives in which (a) the benzene nucleus contains any substituent, (b) the heterocyclic nucleus is hydrogenated, and (c) the remaining free positions 1, 2 or 3 contain alkyl, aralkyl or aryl groups, give similar products on sulphonations The use of the products for emulsifying lime soaps is mentioned.  In examples, the following indols or indol derivatives are sulphonated: 2-heptadecenylindol, the indols obtained from palm nut fatty acid o-toluidide and cod oil fatty acid o-toluidide and a dihydroindol obtained by reducing the indol from palm nut fatty acid o-toluidide.  The indols used as starting materials may be made by acylating with a carboxylic acid an aromatic o-alkylamine, whose amino group may contain one alkyl, aralkyl or aryl group, and subjecting the product to ring closure. Aromatic amine derivatives containing alkoxy, cyano or halogen in the benzene nucleus may be used.  Indols derived from o-toluidine, o-aminoalkylbenzene or m-or p-xylidines which are alkylated or cycloalkylated at the nitrogen by means of residues of dodecylalcohol, olein alcohol, naphthene alcohol, terpene alcohol or cyclohexanol and are acylated by means of formic, acetic, phenylacetic or phenoxyacetic acid are mentioned.  The use, for the acylation of aromatic amines of stearic, oleic, soya, naphthenic, campholic. fencholic and resin acids in order to produce indols having a higher aliphatic or cycloaliphatic residue in the 2-position is referred to.  Specification 303,467, [Class 2 (iii)], is referred to.