Patent GB-643517-A (GB)
Title: Aryl-substituted alkanes
IPC: C07C15/107
Filed: 1947-04-16
Abstract: Mono-aryl substituted branched-chain alkanes are prepared by condensing an acyclic polypropylene of 9-18, preferably 12-15, carbon atoms, and having at least a 75 DEG  C. boiling range, with an aromatic hydrocarbon in the presence of an alkylation catalyst such as BF3, mixtures of BF3+HF, AlCl3, H2SO4 or, preferably, anhydrous HF.  The alkene may be obtained by polymerizing propylene, which may contain inert hydrocarbons such as propane, ethane and methane, and ethylene but no isobutene, and, for example, less than 1 per cent of normal butene, with a phosphoric acid catalyst at 300-500 DEG  F., and separating a tetramer or pentamer fraction boiling preferably at 340-420 and 420-510 DEG  F. respectively.  A blend of 60-80 per cent by volume of tetramer and 40-20 per cent of pentamer or a mixture of polypropylenes having an I.B.P. of 365-370 DEG  F. and F.B.P. of 465-475 DEG  F., upon conversion to the phenyl alkanes and sulphonation, yield effective detergents.  Condensation is effected with benzene and its homologues, naphthalene or methyl naphthalene. Temperature is suitably about 20-50 DEG  F. Hydrofluoric acid may be 200-800 mol. per cent of the olefin. After removal of catalyst, the products are separated by distillation.  A mono-aryl alkane boiling at 500-600 DEG  F. is a preferred fraction for sulphonation.  The dried reactants and the catalyst may be fed upwards through a reactor with a rotary agitator and overflow to a settler whence the oil layer is taken to washing, stripping and fractionating apparatus. Hydrofluoric acid is recovered from the aqueous layer as by stripping with benzene.  The sulphonated monophenyl alkanes and their soluble salts are wetting agents, while the polyvalent metal salts are stabilizers for mineral lubricants.  The monophenyl alkanes yield sulphonyl chlorides with sulphur dioxide and chlorine which by hydrolysis and neutralization give the sodium sulphonates. Examples describe the condensation of propylene tetramer or pentamer fractions of specified characteristics or of 4,5- or 4,6-dimethylheptene with benzene, toluene, xylene or naphthalene in the presence of hydrofluoric acid.  The Specification as open to inspection under Sect. 91 comprises also the condensation with other aromatic compounds than hydrocarbons, e.g. phenol, cresols, xylenols, naphthols, chlor-or nitro-benzene, and benzene or naphthalene sulphonic acid.  The monophenol-substituted alkanes may be converted to alkaline earth, aluminium or zinc derivatives, e.g. by the action of calcium carbide or double decomposition of aluminium sulphate with the sodium salt, which are added to lubricants.  They may also be converted to neutral or acid esters of phosphoric or thiophosphoric acids or their polyvalent metal salts for use as lubricant additives or reacted with olefin oxides to yield non-ionic wetting agents and detergents.  This subject-matter does not appear in the Specification as accepted.ALSO:Additives for mineral lubricating oils for stabilizing and preventing ring sticking consist of polyvalent metal salts of sulphonated monophenyl alkanes, made by condensing acyclic polypropylenes with benzene.  The Specification as open to inspection under Sect. 91 comprises also the use of polyvalent metal derivatives of the corresponding monophenol alkanes made by using phenol in the condensation reaction, alkaline earth metal, Al, and Zn derivatives being referred to, and neutral or acid esters of the monophenol alkanes with phosphoric or thiophosphoric acids or the polyvalent metal salts of the acid esters.  This subject-matter does not appear in the Specification as accepted.