Patent GB-861794-A (GB)
Title: Improved hydrocarbon liquids having increased electrical conductivity
IPC: C10L1/14
Filed: 1958-10-23
Abstract: A salt of a metal having an atomic number of from 22 to 28 inclusive with an aromatic carboxylic acid or an aromatic or aliphatic sulphonic acid, the salt having a molecular weight of at least 200, is employed to raise the electrical conductivity of liquid hydrocarbon compositions, e.g. petroleum distillate fuels (see Group III). Examples of such salts include chromic, ferric and vanadium diisopropylsalicylates; chromic and cobaltic dioctyl sulphosuccinates; chromic, cobaltic and vanadium petroleum sulphonates; chromic and ferric dinonyl naphthalene sulphonates; and chromic, titanium III and manganous salts of C14-18 alkylsalicylic acids. Preferred salts are the basic or neutral salts of trivalent chromium with alkysalicylic acids containing at least one alkyl group of at least 8, preferably 10 to 22, carbon atoms.  A preferred preparation of these salts involves the alkylation of phenol with, e.g., a mixture of C14 to C18 olefins obtained by cracking paraffin wax, in the presence of zinc chloride and hydrochloric acid as catalyst, followed by conversion to alkali metal e.g. sodium, alkylphenates. The phenates are then carboxylated by Kolbe's method in a solvent, e.g. xylene.  Carboxylation is incomplete and the reaction product contains unconverted alkyl phenate, e.g. 38% by weight exclusive of xylene, as well as by-products such as alkyl phenols and alkali metal salts of dicarboxylic acids.  The preparation of pure chromium C14-18 alkyl salicylates, of chromium alkylsalicylates containing alkyl phenol or chromium alkyl phenates, and of basic chromium alkylsalicylates containing chromium alkyl phenates, from this reaction product, is described. Specification 523,451 and U.S.A. Specification 2,285,878 is referred to.ALSO:Compositions of liquid hydrocarbons, particularly petroleum distillates boiling within the range - 40 DEG  C. to 375 DEG  C., having increased electrical conductivity, comprise a major proportion of a hydrocarbon liquid, a small proportion of a salt of a metal having an atomic number of 22 to 28 inclusive with an aromatic carboxylic acid or an aromatic or aliphatic sulphonic acid, the salt having a molecular weight of at least 200, and a small proportion of a metal deactivator containing the structural grouping:- <FORM:0861794/III/1> where R is an alkylene radical containing 1-4 carbon atoms. Salts exemplified are those derived from alkyl hydroxy aryl carboxylic acids, e.g. chromic, vanadium and ferric diisopropylsalicylates, titaniumIII and manganous salts of C14-18-alkylsalicylic acids, and those derived from sulphonated dialkyl esters of aliphatic dicarboxylic acids, petroleum sulphonic acids, and alkylated naphthalene sulphonic p  acids, e.g. chromic and cobaltic dioctyl sulphosuccinates; chromic, cobaltic and vanadium petroleum sulphonates; and chromic and ferric dinonylnaphthalene sulphonates.  Preferred salts are chromium alkylsalicylates having at least one alkyl group of 10 to 22 carbon atoms (see Group IV (b)). The salts increase the electrical conductivity of the hydrocarbons and thereby reduce risk of explosion due to electrostatic charging. Synergists which augment the increased conductivity effect of the salts may also be included in the compositions, e.g. calcium dioctyl sulphosuccinate.  Specified concentrations of salt and synergist in the hydrocarbon are equivalent to 10-9-10-3 gm. atom of metal/litre and 10-9-10-4 gm. mol./litre respectively.  The metal deactivators have a molecular weight not greater than 300 and are present in the compositions at a concentration at least equivalent to that of the metal salt.  The group R is preferably ethylene or 1,2-propylene, e.g. N,N1 - disalicylidene - 1,2 - propanediamine.  Bis - (1 - acetonylethylidene) - ethanediamine and bis - (1 - acetonyl - 2,2 - dimethyl - ethyli - dene) - 1,2 - propanediamine are also specified as deactivators.  Petroleum distillates specified are gasoline, kerosene, JP-1, JP-4 and JP-5 type aviation fuels, VM and P naphtha, cleaner's naphtha, lighter fluid, mineral spirits, rubber solvent, lacquer diluent, insecticide base and solvents such as direct cuts of xylenes and non-aromatics boiling in or near the xylene range, toluene or benzene cuts, and extracts and raffinates (e.g. from SO2 or furfural extraction) obtained from such cuts.  Specification 523,451 and U.S.A.  Specification 2,285,878 are referred to.