GB796603A - Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation - Google Patents

Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation

Info

Publication number
GB796603A
GB796603A GB14319/55A GB1431955A GB796603A GB 796603 A GB796603 A GB 796603A GB 14319/55 A GB14319/55 A GB 14319/55A GB 1431955 A GB1431955 A GB 1431955A GB 796603 A GB796603 A GB 796603A
Authority
GB
United Kingdom
Prior art keywords
phenol
tert
butyl
phenols
methyl
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
GB14319/55A
Inventor
Robert Ellis Knowlton
Hubert William Dyson Stubbs
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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
Priority to NL99615D priority Critical patent/NL99615C/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB14319/55A priority patent/GB796603A/en
Priority to FR1154466D priority patent/FR1154466A/en
Priority to DEI11694A priority patent/DE1035137B/en
Publication of GB796603A publication Critical patent/GB796603A/en
Expired legal-status Critical Current

Links

Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/349—Organic compounds containing oxygen with singly-bound oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/86—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • 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
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • 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—Semi-solids; greasy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Lubricants (AREA)

Abstract

Organic substances, liable to deterioration as the result of peroxide formation, are stabilized by the addition thereto of a small proportion (at most 1 per cent by weight) of a plurality of mononuclear monohydric phenols chosen so that (A) at least one of these phenols has 2 tertiary alkyl nuclear substituents ortho to the hydroxy position and (B) at least one other of these phenols has only one tertiary alkyl nuclear substituent ortho to the hydroxy position or has no tertiary alkyl nuclear substituent ortho to the hydroxy position. The phenols of each type may carry other nuclear substituents but these must be alkyl groups other than tertiary alkyl groups. Organic substances mentioned as being liable to deterioration as the result of peroxide formation are petrol, petroleum oil compositions such as lubricating oils, transformer oils and turbine oils, mineral and vegetable oils, greases, waxes, natural and synthetic rubbers, fats, foodstuffs, aldehydes and tetrahydrofurfuryl alcohol. Phenols of type A include 2,6-di-tert.-butyl-phenol, 2,4,6-tri-tert.-butyl - phenol, 4 - methyl - 2,6 - di - tert. - butyl-phenol, 4 - ethyl - 2,6 - di - tert. - butyl - phenol, 4 - methyl - 2,6 - di - (2 - methylpentyl - 2) - phenol and 4 - methyl - 2 - (2,4,4 - trimethyl-pentyl - 2) - 6 - tert. - butyl - phenol. Type B phenols mentioned are phenol, xylenols, cresols, 2,3,5 - trimethyl - phenol, 2,4,6 - trimethyl-phenol, 2,4,5 - trimethyl - phenol, 2 - methyl - 6 - tert. - butyl - phenol, 3 - methyl - 6 - tert. - phenol, 4 - methyl - 2 - tert. - butyl - phenol, 2,4 - di - tert. - butyl - phenol, 3,4 - dimethyl - 6 - tert. - butyl - phenol, 2,6 - dimethyl - 4 - tert. - butyl - phenol, 2,5 - dimethyl - 4 - tert. - butyl - phenol, 2 - methyl - 4,6 - di - tert. - butyl - phenol and 3 - methyl - 4,6 - di - tert. - butyl-phenol. In examples, the stabilizing effects of various phenols and mixtures of phenols on petrol or nonaldehyde (3,5,5-tri-methyl-hexaldehyde) are described.ALSO:Organic substances, liable to deterioration as the result of peroxide formation, are stabilized by the addition thereto of a small proportion (at most 1 per cent by weight) of a plurality of mononuclear monohydric phenols chosen so that (A) at least one of these phenols has 2 tertiary alkyl nuclear substituents ortho to the hydroxy position and (B) at least one other of these phenols has only one tertiary alkyl nuclear substituent ortho to the hydroxy position or has no tertiary alkyl nuclear substituent ortho to the hydroxy position. The phenols of each type may carry other nuclear substituents but these must be alkyl groups other than tertiary alkyl groups. Organic substances mentioned as being liable to deterioration as the result of peroxide formation include petrol, petroleum oil compositions such as lubricating oils, transformer oils and turbine oils, mineral and vegetable oils, greases and fats. Phenols of type A include 2,6 - di - tert. - butyl - phenol, 2,4,6 - tri - tert.-butyl - phenol, 4 - methyl - 2,6 - di - tert. - butyl-phenol, 4 - ethyl - 2,6 - di - tert. - butyl - phenol, 4-methyl-2,6-di-(2-methylpentyl-2)-phenol and 4 - methyl - 2 - (2,4,4 - trimethylpentyl - 2) - 6 - tert.-butyl-phenol. Type B phenols mentioned are phenol, xylenols, cresols, 2,3,5-trimethyl-phenol, 2,4,6-trimethyl-phenol, 2,4,5-trimethyl-phenol, 2 - methyl - 6 - tert. - butyl - phenol, 3 - methyl - 6 - tert. - butyl - phenol, 4 - methyl - 2 - tert. - butyl - phenol, 2,4 - di - tert. - butyl - phenol, 3,4 - dimethyl - 6 - tert. - butyl - phenol, 2,6 - dimethyl - 4 - tert. - butyl - phenol, 2,5-dimethyl - 4 - tert. - butyl - phenol, 2 - methyl - 4,6 - di - tert. - butyl - phenol and 3 - methyl - 4,6 - di - tert. - butyl phenol. In examples, the stabilizing effects of various phenols and mixtures of phenols on petrol are described.ALSO:Organic substances, liable to deterioration as the result of peroxide formation, are stabilized by the addition thereto of a small proportion (at most 1 per cent by weight) of a plurality of mononuclear monohydric phenols chosen so that (A) at least one of these phenols has 2 tertiary alkyl nuclear substituents ortho to the hydroxy position and (B) at least one other of these phenols has only one tertiary alkyl nuclear substituent ortho to the hydroxy position or has no tertiary alkyl nuclear substituent ortho to the hydroxy position. The phenols of each type may carry other nuclear substituents but these must be alkyl groups other than tertiary alkyl groups. Organic substances mentioned as being liable to deterioration as the result of peroxide formation include rubber. Phenols of type A include 2,6 - di - tert.butyl - phenol, 2,4,6 - tri - tert.butyl - phenol, 4 - methyl - 2,6 - di - tert. butyl - phenol, 4 - ethyl - 2,6 - di - tert.butyl - phenol, 4 - methyl - 2,6 - di - (2 - methylpentyl - 2) - phenol and 4 - methyl - 2 - (2,4,4 - tri - methylpentyl - 2) - 6 - tert.butyl - phenol. Type B phenols mentioned are phenol, xylenols, cresols, 2,3,5 - trimethyl - phenol, 2,4,6 - trimethyl - phenol, 2,4,5 - trimethyl - phenol, 2 - methyl - 6 - tert.butyl - phenol, 3 - methyl - 6 - tert.butyl - phenol, 4 - methyl - 2 - tert.butyl - phenol, 2,4 - di-tert.butyl - phenol, 3,4 - dimethyl - 6 - tert.butyl - phenol, 2,6 - dimethyl - 4 - tert.,butyl - phenol, 2,5 - dimethyl - 4 - tert. butyl - phenol, 2 - methyl - 4,6 - di - tert.butyl - phenol and 3 - methyl - 4,6 - di - tert.butyl phenol.ALSO:Foods, especially vegetable oils and fats, liable to deterioration as the result of peroxide formation, are stabilized by the addition thereto of a small proportion (at most 1 per cent by weight) of a plurality of mononuclear monohydric phenols chosen so that (a) at least one of these phenols has 2 tertiary alkyl nuclear substituents ortho to the hydroxy position; and (b) at least one other of these phenols has only one tertiary alkyl nuclear substituent ortho to the hydroxy position or has no tertiary alkyl nuclear substituent ortho to the hydroxy position. The phenols of each type may carry other nuclear substituents but these must be alkyl groups other than tertiary alkyl groups.
GB14319/55A 1955-05-18 1955-05-18 Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation Expired GB796603A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
NL99615D NL99615C (en) 1955-05-18
GB14319/55A GB796603A (en) 1955-05-18 1955-05-18 Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation
FR1154466D FR1154466A (en) 1955-05-18 1956-05-18 Oxidation, peroxidation and polymerization inhibitors
DEI11694A DE1035137B (en) 1955-05-18 1956-05-18 Process for stabilizing organic compounds with a tendency to auto-oxidize and mixtures thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB14319/55A GB796603A (en) 1955-05-18 1955-05-18 Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation

Publications (1)

Publication Number Publication Date
GB796603A true GB796603A (en) 1958-06-18

Family

ID=10039052

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14319/55A Expired GB796603A (en) 1955-05-18 1955-05-18 Improvements in and relating to inhibitors of oxidation, peroxidation and polymerisation

Country Status (4)

Country Link
DE (1) DE1035137B (en)
FR (1) FR1154466A (en)
GB (1) GB796603A (en)
NL (1) NL99615C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2129011A (en) * 1982-10-25 1984-05-10 Sandoz Ltd Improvements in or relating to organic compounds
EP1736528A3 (en) * 2005-04-04 2007-01-10 Degussa GmbH Process for increasing the oxidative stability of biodiesel.
WO2015023559A1 (en) * 2013-08-12 2015-02-19 Shell Oil Company Methods for modifying auto-ignition properties of a base oil or lubricant composition
US11932746B2 (en) * 2013-11-27 2024-03-19 Si Group, Inc. Composition

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL284832A (en) * 1961-10-30
NL284831A (en) * 1961-10-30
US3442806A (en) * 1966-12-22 1969-05-06 Ethyl Corp Stabilized organic material
CA1149602A (en) * 1980-09-22 1983-07-12 Vandos Shedigian Non-toxic impregnant for electrical capacitors

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2682474A (en) * 1951-05-31 1954-06-29 Eastman Kodak Co Propenyl derivatives of alkoxyphenols as antioxidants

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2129011A (en) * 1982-10-25 1984-05-10 Sandoz Ltd Improvements in or relating to organic compounds
EP1736528A3 (en) * 2005-04-04 2007-01-10 Degussa GmbH Process for increasing the oxidative stability of biodiesel.
WO2015023559A1 (en) * 2013-08-12 2015-02-19 Shell Oil Company Methods for modifying auto-ignition properties of a base oil or lubricant composition
US11932746B2 (en) * 2013-11-27 2024-03-19 Si Group, Inc. Composition

Also Published As

Publication number Publication date
DE1035137B (en) 1958-07-31
NL99615C (en)
FR1154466A (en) 1958-04-10

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