Patent GB-790096-A (GB)
Title: Stabilized organic compositions containing bisphenyl compounds
Inventor: YOUNG DAVID WILSON
IPC: C07C37/20
Filed: 1956-04-17
Abstract: The invention comprises alkylated bisphenyl type compounds corresponding to the general formula <FORM:0790096/IV (b)/1> wherein R1 is an alkyl group with 1 to 5 carbon atoms, R11 and R1111 can be the same or different and consist of hydrogen or alkyl radicals, where the sum of the carbon atoms of R11 and R1111 does not exceed 5. The radicals R111 can be the same or different and consist of hydrogen or alkyl radicals having no more than 22 carbon atoms, and at least two R111 radicals are alkyl radicals having a minimum total carbon atom number of eight.  The compounds may be used as antioxidants for hydrocarbons such as wax, natural and synthetic rubber and other polymers.  They are prepared by condensing a simple or chlorine substituted phenol with a ketone or aldehyde, and the resulting bisphenol is reacted under heat and pressure with methyl chloride and/or methyl iodide, in presence of such compounds as potassium hydroxide and methyl alcohol.  The product is then alkylated either with alkyl halides in the presence of aluminium chloride at 30-80 DEG  C. for 1-8 hours or with various olefines using catalysts such as boron trifluoride in ether, sulphuric acid or aluminium chloride, under dry conditions at 50-60 DEG  C.  Examples are given for the preparation of 2 - (4 - methoxy - 3,5 - ditertiary - butylphenyl) - 2 - (4 - hydroxy - 3,5 - ditertiary - butylphenyl)-propane.  The compounds can also be used to stabilize gasoline and mineral and lubricating oils.ALSO:Compounds suitable as antioxidants in lubricating oil and liquid fuel compositions have the formula: <FORM:0790096/III/1> where R1 is an alkyl radical having from 1-5 carbon atoms, R11 and R1111 are hydrogen or alkyl radicals, and can be the same or different.  The sum of the carbon atoms of R11 and R1111 does not exceed 5.  R111 is hydrogen or an alkyl radical having no more than 22 carbon atoms and can be the same or different. At least two R111 radicals are alkyl radicals having a minimum total of eight carbon atoms.  These compounds are suitable as antioxidants when mixed in a minor proportion with e.g. 0.1 to 5 lb./5000 gallons of gasoline or 0.02 to 10 per cent by weight of lubricating oils. The antioxidants may be added to hydrocarbon lubricating oils (e.g. mineral oils) such as turbine oils or to synthetic ester lubricating oils.  The latter may be thickened to greases with metallic soaps. An example is given using 2-(4-methoxy 3,5-ditertiary butylphenyl) - 2 - (4 - hydroxy - 3,5 - ditertiary butylphenyl) propane in leaded gasoline.ALSO:Compounds suitable as antioxidants for synthetic rubber have the formula: <FORM:0790096/IV (a)/1> where R1 is an alkyl radical having from 1-5 carbon atoms, R11 and R1111 are hydrogen or alkyl radicals and can be the same or different, the sum of the carbon atoms of R11 and R1111 does not exceed 5, R111 is hydrogen or an alkyl radical having no more than 22 carbon atoms and can be the same or different and at least two R111 radicals are alkyl radicals having a minimum total of eight carbon atoms.  The synthetic rubber may be an isobutylenediolefin copolymer, a polymer of a conjugated diolefine having 4-6 carbon atoms, e.g. 1,3-butadiene, isoprene, 2,3-dimethylbutadiene, 2-chloro 1,3-butadiene, piperylene or 2-methyl-1,3-pentadiene, or a copolymer thereof with acrylonitrile, methyl acrylonitrile, methyl methacrylate, styrene, alpha methyl styrene, vinyl naphthalene, vinyl ketones, vinylidene chloride, diethyl fumarate or vinyl pyridine.  An example is given of the use of 2-(4-methoxy-3,5-ditertiary butyl phenyl)-2-(4-hydroxy-3,5-ditertiary butyl phenyl) propane.ALSO:Compounds suitable as antioxidants for natural rubber have the general formula: <FORM:0790096/V/1> where R1 is an alkyl radical having from 1-5 carbon atoms, R11 and R1111 are hydrogen or alkyl radicals and can be the same or different.  The sum of the carbon atoms of R11 and R1111 does not exceed 5.  R111 is hydrogen or an alkyl radical having no more than 22 carbon atoms, and can be the same or different.  At least two R111 radicals are alkyl radicals having a minimum total of eight carbon atoms.  An example is given of the use of 2(4-methoxy-3, 5, ditertiary butylphenyl)-2-(4-hydroxy, 3, 5 ditertiary butylphenyl) propane as an antioxidant.