Patent GB-690423-A (GB)
Title: A process for the preparation of substituted sulphonamides
IPC: D06M13/438
Filed: 1949-04-14
Abstract: Substituted sulphonamides of the type in which an alkylbenzene radical is connected to the nucleus of an aromatic sulphonic acid through a sulphonamide group and wherein at least one such alkylbenzol-sulpho-acid radical is attached to the nitrogen atom, are obtained by reacting an alkyl-benzol-sulphochloride, the alkyl radical of which contains from 10 to 18 carbon atoms with an aromatic aminosulphonic acid or salt thereof which still contains at least one hydrogen atom united to the nitrogen atom.  The reaction may be carried out with or without the admixture of water.  The alkylbenzol-sulphochlorides used as starting materials may be prepared by reacting the alkylbenzol-sulpho acids or the salts thereof with chlorsulphonic acid as described in Specification 679,185 and they may contain either one or a plurality of alkyl chains having from 10 to 18 carbon atoms.  The alkyl groups may be straight-chained or branched and may be attached to the benzol nucleus by a primary, secondary or tertiary carbon atom.  The preferred aromatic sulphonic acid is sulphanilic acid which may be employed in the form of its sodium salt, the reaction being generally effected at below 100 DEG  C. and preferably at between 20 DEG  and 40 DEG  C.  An acid binding substance may be added to the reaction mixture.  Bis (alkyl-benzol-sulpho)-amides may be obtained by reacting one mole. of the aromatic aminosulphonic acid with two moles of the alkyl-benzol-sulphochloride.  In an example, sulphanilic acid is neutralized with an aqueous solution of caustic soda and dodecyl benzene sulphochloride and caustic soda solution are then added dropwise to the stirred solution maintained at 30-35 DEG  C.  The temperature is then raised to about 70 DEG  C., the final product after isolation from the resulting emulsion being a slightly water-soluble paste.  The products may be used as wetting agents, as washing and cleansing means, as auxiliary means in the manufacture of textiles, as softeners, and as means to prevent corrosion.  The Specification as open to inspection under Sect. 91 includes reacting alkyl benzol sulphochlorides wherein the alkyl group contains at least 4 carbon atoms with ammonia, ammonium salts or organic derivatives of ammonia which contain at least one hydrogen atom attached to the nitrogen atom, either in the presence or absence of water.  The preferred ammonium salt is ammonium carbonate.  Specified derivatives are mono- and dimethylamine, mono- and diethyl amine, propyl amines, octyl, decyl and dodecyl amines, hexadecenyl amine, cyclohexyl and alkyl cyclohexyl amines, piperidine, amino pyridine, amino pyrimidine, carbazol, furfuryl amine, amino-thiazole, mono- and diethanolamine, hydroxy propyl amine, aminoacetic acid, aminopropionic acid, lysalbinic acid, protalbinic acid, hydrolysate from albumen and albumen containing substances, e.g. leather; amino alkyl sulpho acids, aniline and its derivatives substituted at the nitrogen or in the benzol ring by alkyl or cycloalkyl groups, diphenyl amine, phenylene diamine, nitraniline, anthranilic acid, naphthylamine and its substitution products and aminophenols.  It is stated that more than one amino group may be present in these compounds. Other compounds specified are the amides of carboxylic or sulpho acids, e.g. of formic, acetic, propionic acid or other higher straight or branched chain saturated or unsaturated aliphatic or cycloaliphatic carboxylic acids, amides of ether-carboxylic acids which may be substituted at the nitrogen atom, such as 1-butyl-hydroxy-acetic acid, cyclohexyl - hydroxy acetic acid, n - octyl - hydroxypropionic acids, phenoxy-carboxylic acids which may also be substituted in the phenyl radical by alkyl or nitro groups or by halogen atoms.  Other derivatives which may be used are amides of aliphatic, cycloaliphatic or mixed aliphatic - cycloaliphatic dicarboxylic acids and the amides and N-substituted amides of aromatic and hydroaromatic carboxylic acids, e.g. benzoic, phthalic, nitrobenzoic, chlornitrobenzoic as well as halogen substitution products of aromatic carboxylic acids, also the amides and substituted amides of sulpho acids, e.g. those formed by reacting ammonia or amines with sulphohalides obtained by reacting sulphur dioxide and halogen or aliphatic, cycloaliphatic and aliphatic-aromatic hydrocarbons and which may also contain a plurality of sulphonamide groups in the molecule, also the amides and N-substituted amides of aromatic mono- or di-sulpho acids which may also carry alkyl groups in the aromatic radical.  There may also be used the alkyl benzol sulphonamides obtained by the present process whereby symmetrical or unsymmetrical bis-(alkyl-benzol-sulpho)-imides are obtained.  The following additional examples are given: (1) decyl benzol is sulphonated with sulphuric acid to give the sulpho-acid which is converted to the sulphochloride by reacting with chlorsulphonic acid; the sulpho-chloride is then reacted with concentrated aqueous ammonia to yield decylbenzol sulphonamide; (2) dodecyl benzol sulphonamide is obtained from the sulphochloride as in (1); (3) and (4) aqueous solutions of monomethylamine and diethylamine respectively are reacted with decyl benzol sulphochloride to yield viscous oils; (5) an emulsion of aniline in water is treated with dodecyl benzol sulphochloride, to yield a viscous liquid; (6) as in (5) except that monomethyl aniline is used; (7) decyl - benzol - sulphonamide is reacted with decyl-benzol-sulpho-chloride; (8) gelatine is swelled in water and dissolved by warming, caustic soda solution is then added and the mixture treated with dodecyl benzol sulphochloride to give a paste like product which when dissolved in water displays good lather-forming and cleansing properties; (9) casein is soaked in water, a solution of caustic soda added and the mixture treated with dodecyl benzol sulphochloride at 40 DEG  C.; the product yields an aqueous solution of good lather-forming properties; (10) casein is treated with a solution of caustic soda at 90 DEG  C. for 2 1/2 hours and dilute hydrochloric acid then added, the casein being degraded to protalbinic and lysalbinic acid, dodecyl benzol sulphochloride is then added along with more caustic soda and reaction effected at 70 DEG  C. to yield a viscous mass having lather-forming and lime-soap-dispersing properties; similar products are obtained by using twice the quantity of the sulphochloride; (11) as in (10) except that pearl glue is used instead of casein; (12) dodecyl benzol sulphochloride and caustic soda solution are added to the neutralized decomposition product from casein and caustic soda, after reaction at 60 DEG  to 70 DEG  C., benzyl chloride and more caustic soda solution are added to yield a product having dispersing properties.  This subject-matter does not appear in the Specification as accepted.