Patent GB-798488-A (GB)
Title: Quaternary ammonium compounds and method for the preparation thereof
Inventor: GREEN JEROME
IPC: C08F8/44
Filed: 1956-01-09
Abstract: Quaternary ammonium salts are prepared by bringing together in the presence of water a quaternary ammonium halide dissolved in a solvent and an anion-exchange resin which is insoluble in said solvent and contains an anion other than halide.  The water may comprise all or part of the solvent for the quaternary halide or may be present in the resin.  The process is particularly suitable for the conversion of quaternary halides such as chlorides into less readily prepared salts such as phosphates and nitrites whose solutions are less corrosive than halides.  The resin is preferably in the form of a column or bed of discrete particles so that it can be regenerated by a solution of an inorganic salt of the desired anion and the process repeated continuously.  Suitable resins are those containing quaternary ammonium groups obtained by reacting tertiary bases with polymers of vinyl-aromatic compounds containing a -halo-alkyl groups, especially copolymers of monovinyl and polyvinyl aromatic compounds. Suitable organic solvents are alcohols, glycols, ketones, aldehydes and dioxane. The quaternary cation may be of the formula NR1R2R3R4 where R1 an R2 are methyl and R3 and R4 are methyl, benzyl or C8-C18 alkyl or alkenyl, or may be an imidazolium, imidazolinium, pyrrolidinium, piperidinium, pyridinium, morpholinium, quinolinium, isoquinolinium or tetrazolinium ion, a large number of these being listed.  The anion in the desired product can be bromate, carbonate, bicarbonate, nitrate, nitrite, sulphate, sulphite, bisulphate, bisulphite, orthophosphate, pyrophosphate, polyphosphate, silicate, cyanide, formate, acetate or aminoacetate.  Examples show the conversion of 1-benzyl-1-(b  - hydroxyethyl) - 2 - tridecyl - imidazolinium chloride into the corresponding nitrite and phosphate.ALSO:The imidazolinium nitrite of the formula <FORM:0798488/III/1> acts as corrosion inhibitor when added to burning oils, diesel fuels, kerosene, gasoline and crude petroleum from the well and prevents attack on equipment in oil wells.ALSO:Strongly-basic anion-exchange resins are prepared by reacting tertiary alkyl, carbocyclic or heterocyclic amines with a -halo-alkyl vinyl aromatic resins, especially copolymers of 0.5-40 per cent of a polyvinyl-aromatic compound and 99.5-60 per cent of a monovinyl-aromatic compound containing 0.2-1.5 halomethyl groups per aromatic nucleus.  The amine may be trimethylamine, triethylamine, tributylamine, or an amino-alkanol or alkanediol such as dimethylethanolamine, dimethylpropanol, methyldiethanolamine, 1 - methylaminopropane - 2 : 3 - diol or dioctylethanolamine.  Suitable vinyl-aromatic compounds are styrene, a -methylstyrene, chlorostyrene, vinyl-toluene and vinyl-naphthalene on the one hand and divinylbenzene, divinyltoluene, divinylxylene, divinylnaphthalene and divinylethylbenzene on the other.  Weakly-basic anion-exchange resins are made as above by using a primary or secondary amine such as methylamine, dimethylamine, butylamine, dibutylamine, isobutylamine, aniline, benzidine, toluidine, xylidine, naphthylamine, benzylamine, dibenzylamine, naphthalenediamine, ethylenediamine, cyclohexylamine, dicyclohexylamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, propylenediamine or dipropylenetriamine.