Patent GB-810560-A (GB)
Title: Improvements relating to alkylarylsulphonyl derivatives of amino acids, to corrosion and rust inhibiting compositions thereof and their use
IPC: C10L1/24
Filed: 1955-10-20
Abstract: Lubricating oils and greases and anti-rust or slushing compositions for the protection of metals against atmospheric corrosion contain as a corrosion-inhibiting ingredient a compound of formula <FORM:0810560/III/1> wherein R is an alkyl group having 8-24 carbon atoms, Ar is an arylene group, R1 and R2 are hydrogen or an alkyl or carboxyalkyl radical, n i 0, 1 or 2, m is 1 or 2 and Y is hydrogen, a monovalent cation or the equivalent of a polyvalent cation (see Group IV (b)).  Specified oleaginous vehicles or solvents which may be used are hydrocarbon oils, fatty oils, fats and synthetic lubricants such as polyesters, polysiloxanes, polyalkylene glycols and polyolefines. Many other vehicles such as gasoline, fuel oil, alcohols, glycols, glycol ethers, ketones, esters, petroleum waxes, natural waxes, &c., are specified.  In an example samples of a mineral lubricating oil containing compounds of the above formula and in some cases stearic acid and/or a tertiary alkyl primary amine are subjected to rust and emulsion tests.ALSO:The invention comprises compounds of formula <FORM:0810560/IV (b)/1> wherein R is an alkyl group having 8-24 carbon atoms, Ar is an arylene radical, R1 and R2 are hydrogen or an alkyl or carboxylalkyl radical, n is 0, 1 or 2, m is 1 or 2 and Y is hydrogen, a monovalent cation or the equivalent of a polyvalent cation.  The compounds are used in corrosion and rust-inhibiting compositions (see Groups II, III and XIII).  The acids of the above formula may be prepared by (a) reacting an alkarylsulphonyl chloride with an amino-acid salt followed by acidification, (b) reacting an alkarylsulphonyl chloride with an ester or nitrile of an amino-acid followed by saponification and acidification, or (c) reacting an alkarylsulphonamide with a chlorocarboxylic acid salt followed by acidification.  Amino-acids from which the compounds may be derived are glycine, a - and b -alanine, sarcosine and iminodiacetic, aspartic and glutamic acids.  The group Rm-Armay be derived from straight- or branched-chain octyl, decyl, dodecyl, tetradecyl, hexadecyl or octadecyl derivatives of benzene, naphthalene, anthracene or chrysene.  Specified compounds are N-(dodecylbenzene sulphonyl) glycine or glutamic acid or a - or b -alanine, N-(dinonylnaphthalene sulphonyl) glycine or sarcosine or iminodiacetic acid or glutamic acid or a - or b -alanine N-(octadecylanthracene sulphonyl) sarcosine and N-(octyl xylyl) sarcosine.  In examples: (1) n-dodecylbenzene sulphonyl chloride was reacted with sodium sarcosinate and the reaction mixture acidified to give N-(n-dodecylbenzene sulphonyl) sarcosine; (2) n-dodecylbenzene sulphonyl chloride was reacted with dimethyl iminodiacetate hydrochloride, the product saponified with aqueous sodium hydroxide solution and acidified to give N-(n-dodecyl benzene sulphonyl) iminodiacetic acid; (3) as in (1) but technical dodecylbenzene sulphonyl chloride used; (4) iminodiacetic acid and excess triethylamine were reacted with technical dodecylbenzene sulphonyl chloride followed by-acidification; (5) as in (2) but technical dodecylbenzene sulphonyl chloride used, the product, obtained by saponification of the ester with methanolic potassium hydroxide, contained some unsaponified ester.  n-Dodecylbenzene sulphonyl chloride was prepared by reacting n-dodecylbenzene with chlorosulphonic acid, the product of this reaction being reacted further with phosphorus pentachloride.  Technical dodecylbenzene sulphonyl chloride (containing 15 per cent of dodecylbenzene sulphonic acid) was prepared by reacting commercial dodecylbenzene with chlorosulphonic acid.ALSO:Acidic aqueous solutions used as metal pickling baths may contain as an anti-corrosion ingredient a compound of formula: <FORM:0810560/II/1> wherein R is an alkyl group having 8-24 carbon atoms, Ar is an arylene group, R1 and R2 are hydrogen or an alkyl or carboxyalkyl radical n is 0, 1 or 2, m is 1 or 2 and Y is hydrogen, a monovalent cation or the equivalent of a polyvalent cation (see Group IV (b)).