Patent GB-695809-A (GB)
Title: Stabilizer for mineral oils
IPC: C10L1/22
Filed: 1950-09-14
Abstract: Products are obtained by reacting acyl halides with pyridine, quinoline, carbazole and derivatives thereof containing hydrocarbon (C1-C20), hydroxy, thio, alkoxy and alkylthio (C1-C20), nitro and halogen substituents; the acyl halides are of the formula RCOX, where R is a hydrocarbon radical of 1-30 (preferably 20) carbon atoms and X is halogen; the reaction takes place at 0-100 DEG  C., preferably at room temperature.  The products are probably of the type of N-acylpyridinium halides.  They may be further reacted at 20-120 DEG C. with compounds R1TM to exchange TR1 for the halogen, T being O or S, R1 a hydrocarbon group of 1-20 carbon atoms, preferably an alkyl radical, and M an alkali metal. In the examples: (1) 2 : 6-lutidine is reacted with acetyl chloride; (2) 8-hydroxyquinoline with acetyl chloride; (3) quinoline with acetyl chloride; (4) quinoline with benzoyl chloride; (5) 2 : 6-lutidine is mixed with benzoyl chloride and then treated with sodium methoxide; (6) quinaldine is reacted first with benzoyl chloride and then with sodium lauryl mercaptide; (7) pyridine is reacted with benzoyl chloride and sodium lauryl mercaptide.  In both steps the reactants are used in stoichiometric proportions.  Other suitable components are listed. The products are stabilizers for hydrocarbon oils (see Groups III and XXIX).ALSO:Mineral oil fractions are stabilized against oxidation and/or polymerization by the presence of a product (see Group IV(b)) obtained by reacting at 0-100 DEG C an acyl halide RCOX with pyridine, quinoline or carbazole or derivatives thereof containing hydrocarbon (C1-C20), hydroxy, thio, alkoxy and alkylthio (C1-C20), nitro or halogen substituents; alternatively there may be used the conversion products obtained by replacing halogen by -TR1 in the above compounds; R is a hydrocarbon radical of 1-30 (preferably 20) carbon atoms, R1 is a hydrocarbon radical and T is O or S.  Both products are probably of the type of N-acylpyridinium compounds. Mineral oil fractions, and compositions containing such fractions, which may be stabilized include motor fuels, diesel fuels, lubricants, turbine oils, emulsifiable oils, flushing oils, cutting oils, transformer oils and greases.  The products of the invention may be present to the extent of 0.05-5 per cent by weight, preferably 0.05-2 per cent.  Examples show various oils stabilized with the following reaction products: (1) 2:6-lutidine and acetyl chloride, (2) 8-hydroxy-quinoline and acetyl chloride, (3) quinoline and acetyl chloride, (4) quinoline and benzoyl chloride, (5) 2:6-lutidine, benzoyl chloride and sodium methoxide, (6) quinaldine, benzoyl chloride and sodium lauryl mercaptide, and (7) pyridine, benzoyl chloride and sodium lauryl mercaptide.  The oils specified are: (1) turbine oil of Saybolt viscosity 43 sec. at 210 DEG F containing 0.06 per cent of zinc naphthenate with or without 0.2 per cent of 2:6-di-t-butyl-4-methylphenol, (2) solvent-extracted paraffinic mineral lubricating oil of SAE 20 viscosity grade, (3) paraffinic oil of 46 sec. Saybolt viscosity at 210 DEG F blended with polybutene, (4) partially cracked hydrocarbon distillate boiling at 320-660 DEG F.  Results are given for these oils.  Other additives may be present such as phenols, phenol sulphides, metal soaps, sulphonates, phenates, alcoholates, organophosphates, phosphites, thiophosphates, thiophosphites, xanthates, thioxanthates and thiocarbamates, dyes, pour point depressants, thickened or sulphurised fatty oils, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefine polymers and especially plasticisers and defoamers such as octyl, lauryl and stearyl alcohols.  The mineral oils may be derived from paraffinic, naphthenic or asphaltic sources.  Oils made by polymerisation of olefines, reaction of carbon oxides with hydrogen, hydrogenation of coal or distillation of tar or shale oil may also be employed. They may be blended with each other or with animal, vegetable or fish oils or their hydrogenated or volatilized products.  Other stabilizers are mentioned besides those specified above.