Patent GB-939776-A (GB)
Title: Organic aromatic compounds
IPC: C07C37/20
Filed: 1961-08-25
Abstract: Organic materials subject to oxidative deterioration in presence of air, oxygen or orzone are stabilized by the presence of 0,001-5% of a 3,5-dialkyl-4-hydroxybenzyl chloride wherein one alkyl has 1-12 and the other 3-12 carbon atoms, the alpha-carboxy atom being optionally substituted by a C1-12 alkyl or C6-12 mononuclear aryl radical.  Such materials include gasoline (which may contain PbEt4), hydrocarbon-derived and synthetic lubricants, turbine, hydraulic and transformer oils, soaps, paraffin and microcrystalline waxes, butter fat, lard, beef tallow and linseed, cod liver, castor, soybean, rapeseed, coconut, olive, palm, corn, sesane, peanut and babassu oils; also synthetic diester oils (e.g. sebacates and adipates) used as aircraft instrument oils, hydraulic and damping fluids and precision bearing lubricants.  In Examples (3)-(6), mineral oils alone or with a methacrylate V.I. improver, (7) a pentaerythritol ester, (8) dioctyl sebacate, (9) a mineral oil + Ba petroleum sulphonate, cetyl or lauryl polyacrylate, dimethyl silicone and a dialkyl zinc dithiophosphate, (10) a mineral oil + calcium octyl phenyl sulphide, a sulphurized sperm oil, a wax-alkylated-phenyl benzoate and polyisobutylene and (11) and (12) gasolines, are stabilized with specified dialkylhydroxy-benzyl chlorides. Lubricating oils may also be stabilized with mono- or polysulphide, and phosphonate derivatives of the benzyl chlorides; specified in this connection are di-(3,5-di-t-butyl-4-hydroxybenzyl) sulphide and dimethyl-(3,5di-t-butyl-4-hydroxy benzyl) phosphonate.ALSO:Polymers such as natural rubber, polyethylene, polypropylene, polybutylene, polybutadiene and methyl-, butyl-, GRS-, GRN-, piperylene-and dimethylbutadiene-rubbers are stabilized to oxidative deterioration in presence of air, oxygen or ozone, by the presence of 0,001-5% of a 3,5-dialkyl-4-hydroxybenzyl chloride wherein one alkyl has 1-12 and the other 3-12 carbon atoms, the alpha-carbon atom being optionally substituted by a C1-12 alkyl or C6-12 mononuclear aryl radical.ALSO:The invention comprises 3,5-dialkyl-4-hydroxybenzyl chlorides wherein one alkyl has 1-12 carbon atoms and the other has 3-12 carbon atoms; the alpha-carbon atom is optionally substituted by a C1-12 alkyl or C6-12 mononuclear aryl radical.  Such compounds are prepared by reacting together the appropriate 2,6-dialkylphenol and aldehyde. together with excess hydrogen chloride.  By reaction of the benzyl chlorides with sodium mono- or polysulphide, the corresponding substituted dibenzyl sulphide or polysulphide is formed.  By reaction of the benzyl chlorides with trialkyl phosphite, the corresponding dialkyl substituted-benzyl phosphonate may be prepared.  The preparation of 3,5-di-t-butyl-4-hydroxybenzy chloride and its conversion to di-(3,5-di-t-butyl-4-hydroxybenzyl) sulphide and di-isopropyl 3,5-di-t-butyl-4-hydroxybenzylphosphonate, is exemplified.  Organometallic compounds such as PbEt4 may be stabilised to oxidative deterioration by the addition of 0,001-5% of the benzyl chlorides.ALSO:Butter fat, lard and beef tallow may be stabilized against oxidative deterioration by the incorporation of 0.001-5% of a 3,5-dialkyl-4-hydroxybenxyl chloride, e.g. 3,5-ditert.-butyl-4-hydroxybenzyl chloride.