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GB927179A - Asymmetric methylene-bis-phenols and their use as anti-oxidants - Google Patents

Asymmetric methylene-bis-phenols and their use as anti-oxidants

Info

Publication number
GB927179A
GB927179A GB11538/60A GB1153860A GB927179A GB 927179 A GB927179 A GB 927179A GB 11538/60 A GB11538/60 A GB 11538/60A GB 1153860 A GB1153860 A GB 1153860A GB 927179 A GB927179 A GB 927179A
Authority
GB
United Kingdom
Prior art keywords
tert
butyl
hydroxyphenyl
oil
phenols
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB11538/60A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ethyl Corp
Original Assignee
Ethyl Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ethyl Corp filed Critical Ethyl Corp
Publication of GB927179A publication Critical patent/GB927179A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/115—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using acetals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
    • C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Lubricating oils, liquid fuels, vegetable oils and fats and waxes are stabilized against oxidation by the addition of a compound of formula <FORM:0927179/III/1> <FORM:0927179/III/2> wherein A and B are hydrogen atoms or alkyl groups having up to 9 carbon atoms and at least one of A or B is a tertiary alkyl group having 4-9 carbon atoms and is positioned ortho to one of the hydroxyl groups and when the hydroxyl groups are both para to the methylene bridge A and B are such that the molecule is not symmetrical (see Group IV(b)). The compounds are used in admixture with the corresponding symmetrical bis-phenols. Specified lubricating oils include mineral lubricating oils and synthetic di-ester oils, examples being given. Specified liquid fuels are gasoline, jet fuel, kerosine and fuel oil. The lubricants and fuels may contain the usual additives. Specified vegetable oils and fats include lard, beef tallow, fish oils, castor oil, soybean oil, rapeseed oil, coconut oil, olive oil, palm oil, corn oil, sesame oil, peanut oil, babassu oil, citrus oils and cotton seed oil.ALSO:Natural and synthetic rubbers and synthetic polymers are stabilized against oxidation by the addition of a compound of formulae <FORM:0927179/IV(a)/1> <FORM:0927179/IV(a)/2> wherein A and B are hydrogen atoms or alkyl groups having up to 9 carbon atoms and at least one of A or B is a tertiary alkyl group having 4-9 carbon atoms and is in o-position to one of the hydroxyl groups and when the hydroxyl groups are both para to the methylene bridge A and B are such that the molecule is not symmetrical (see Group IV(b)). The compounds are used in admixture with corresponding symmetrical bis-phenols. Specified synthetic rubbers include polybutadiene, methyl and butyl rubbers, GR-S and GR-N, piperylene rubber and dimethylbutadiene rubber. Preferred polymers are those obtained by polymerization of mono-ethylenically unsaturated monomers such as ethylene, propylene, butylene and isobutylene. In examples: (1) polyethylene is admixed with (3,5-di-tert-butyl-4-hydroxyphenyl)-(31, 51-dimethyl- or -diisopropyl- or -di-tert-butyl- or 31-methyl-51-tert-butyl-41-hy droxyphenyl)-methane; (2) polypropylene is mixed with a mixture of bis-phenols containing (3,5-di-tert-butyl-4-hydroxyphenyl) - (31-tert-butyl-21- or -4-hydroxyphenyl)-methane as major components; (3) polyisobutylene is mixed with a mixture of bis-phenols containing (3,5-di-tert-butyl-4-hydroxyphenyl) - (31-methyl-51-tert-butyl-41-hydroxyphenyl) -methane; (4) (3-methyl-5-tert-octyl-4-hydroxyphenyl)- (31, 51-di-tert-butyl-4-hydroxyphenyl)-methane is mixed with a rubber batch containing GR-S rubber, zinc propionate stearate, carbon black, road tar, sulphur and mercaptobenzothiazole and the mixture is cured; (5) a mixture of bis-phenols containing (3,5-di-tert-butyl-4-hydroxyphenyl)-(31 - methyl - 51 - tert - butyl - 41 - hydroxyphenyl)-methane is mixed with crepe, natural rubber, wax, ultramarine dye, zinc oxide, titanium dioxide, sulphur, stearic acid, benzothiazolyl disulphide and an amine activator and the mixture vulcanized.ALSO:The invention comprises methylene-bisphenols of formula <FORM:0927179/IV(a)/1> <FORM:0927179/IV(a)/2> wherein A and B are hydrogen atoms or alkyl groups having up to 9 carbon atoms and wherein at least one A or B is a tertiary alkyl group having 4-9 carbon atoms and is positioned ortho to one of the hydroxyl groups and when the hydroxyl groups are both para to the methylene bridge A and B are such that the molecule is not symmetrical; and the compounds (3,5-di-tertbutyl- 4-hydroxyphenyl) - (31-tert-butyl-41-hydroxyphenyl)-methane and (3,5-di-tert-butyl-4-hydroxyphenyl) - (31-methyl- 51-tertbutyl-41-hydroxyphenyl) -methane. The compounds are prepared, in admixture with symmetrical methylene-bis-phenols, by reacting a mixture of suitably substituted phenols with formaldehyde and an aliphatic alcohol under basic conditions. The bis-phenols are used as anti-oxidants in oils and fats (see Group III), rubbers and synthetic polymers (see Group IV(a)). In an example a solution in p ethanol of 2-methyl-6-tert.-butyl-phenol and 2,6-di-tert-butyl-phenol is mixed with formaldehyde and aqueous sodium hydroxide and refluxed under nitrogen to give (3,5-di-tert.-butyl-4-hydroxyphenyl) - (31-methyl- 51-tertbutyl-41-hydroxyphenyl) -methane in admixture with symmetrical bis-phenols, benzyl ethers and benzyl alcohols. In further examples mixtures of (a) 2,6-di-tert-butylphenol and 2-tert.-butylphenol or 2-methyl- 6-tert-butyl-phenol and (b) 6-tert-amyl-p-cresol and 2-methyl-6-tert.- butylphenol are similarly reacted.ALSO:Oxidative deterioration of animal and vegetable oils and fats, e.g. butter, lard, beef tallow and cod liver oil, and of the fat in foods such as potato chips, fried fish, doughnuts, crackers, pastries and cakes, is prevented by asymmetrical bisphenols: <FORM:0927179/VI/1> <FORM:0927179/VI/2> wherein A and B are hydrogen atoms or alkyl groups having up to 9 carbon atoms and at least one of A or B is a tertiary alkyl group having 4-9 carbon atoms and is positioned ortho to one of the hydroxyl groups and, when the hydroxyl groups are both para to the methylene bridge A and B are such that the molecule is not symmetrical (see Group IV (b)). The compounds are used in admixture with the corresponding symmetrical bis-phenols.
GB11538/60A 1959-04-06 1960-04-01 Asymmetric methylene-bis-phenols and their use as anti-oxidants Expired GB927179A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US80413159A 1959-04-06 1959-04-06

Publications (1)

Publication Number Publication Date
GB927179A true GB927179A (en) 1963-05-29

Family

ID=25188253

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11538/60A Expired GB927179A (en) 1959-04-06 1960-04-01 Asymmetric methylene-bis-phenols and their use as anti-oxidants

Country Status (3)

Country Link
DE (1) DE1294583B (en)
GB (1) GB927179A (en)
NL (1) NL250204A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2365545A1 (en) * 1976-09-27 1978-04-21 Upjohn Co CATALYST AND PROCESS FOR PREPARING BISPHENOLS
US5616816A (en) * 1992-10-16 1997-04-01 The Lubrizol Corporation Tertiary alkyl alkylphenols and organic compositions containing same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB790096A (en) * 1956-04-17 1958-02-05 Exxon Research Engineering Co Stabilized organic compositions containing bisphenyl compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2365545A1 (en) * 1976-09-27 1978-04-21 Upjohn Co CATALYST AND PROCESS FOR PREPARING BISPHENOLS
US5616816A (en) * 1992-10-16 1997-04-01 The Lubrizol Corporation Tertiary alkyl alkylphenols and organic compositions containing same
US6002051A (en) * 1992-10-16 1999-12-14 The Lubrizol Corporation Tertiary alkyl alkylphenols and organic compositions containing same

Also Published As

Publication number Publication date
NL250204A (en)
DE1294583B (en) 1969-05-08

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