GB932818A - Novel antioxidant 3,5-dialkyl-4-hydroxybenzyl ethers and their preparation - Google Patents

Novel antioxidant 3,5-dialkyl-4-hydroxybenzyl ethers and their preparation

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Publication number
GB932818A
GB932818A GB35552/61A GB3555261A GB932818A GB 932818 A GB932818 A GB 932818A GB 35552/61 A GB35552/61 A GB 35552/61A GB 3555261 A GB3555261 A GB 3555261A GB 932818 A GB932818 A GB 932818A
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United Kingdom
Prior art keywords
carbon atoms
formula
group containing
oils
inclusive
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
GB35552/61A
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.)
Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB932818A publication Critical patent/GB932818A/en
Expired legal-status Critical Current

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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
    • C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
    • C—CHEMISTRY; METALLURGY
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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    • C08K5/13—Phenols; Phenolates
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    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
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    • C08K5/372—Sulfides, e.g. R-(S)x-R'
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • 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
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling

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

Abstract

Gasoline, motor oils, lubricating oils, diesel oils, turbine oils, gear oils, transformer oils, domestic heating oils, cutting oils, brake fluids, drying oils, paints, and fixed oils are stabilized against oxidation by 3,5-dialkyl-4-hydroxybenzyl ethers of the formula:- <FORM:0932818/III/1> wherein n is 0 and m is 1, n is 1 and m is an integer from 1 to 5 inclusive, each R is an alkyl group containing from 3 to 8 carbon atoms, branched on the alpha carbon atom, R1 is (1) an unsubstituted aliphatic hydrocarbon group containing at least m+1 carbon atoms, connected to m+1 hydroxybenzyloxy groups, or (2) a phenylene group, or (3) a polyalkyleneoxy group of the formula -R2-(OR2)pin which each R2 represents an alkylene group containing from two to six carbon atoms, and p is a whole positive number from 1 to 5, inclusive, with the proviso that, when R1 represents said polyalkyleneoxy or phenylene group, m is 1. The compositions may contain as a second stabilizer, an organic sulphur compound of the type R1-Sx-R2 where x is a whole number and R1 and R2 are similar or dissimilar organic groups bound to Sx by carbon atoms, or an organic sulphur compound of the formula R1(R2)N-C(=S)-S-M-S-C(=S)-N(R2)R1, wherein M is a metal of Group II of the Periodic System and R1 and R2 are hydrocarbon groups having from 1 to 6 carbon atoms, or a trialkyltrithiophosphite having 6 to 20 carbon atoms, or polymeric products such as polyalkoxyalkylsulphides, polyalkoxyalkoxyalkylsulphides or polyhydroxyalkylsulphides. Specifications 847,248 and 893,896 are referred to.ALSO:Polystyrene, natural and synthetic rubber, for instance, styrene-butadiene rubber and polyisoprene are stabilized against oxidation by 3,5-dialkyl-4-hydroxybenzyl ethers of the formula:- <FORM:0932818/IV(a)/1> wherein n is 0 and m is 1, n is 1 and m is an integer from 1 to 5 inclusive, each R is an alkyl group containing from 3 to 8 carbon atoms, branched on the alpha carbon atom, R1 is (1) an unsubstituted aliphatic hydrocarbon group containing at least m+1 carbon atoms, connected to m+1 hydroxybenzyloxy groups, or (2) a phenylene group, or (3) a polyalkyleneoxy group of the formula -R2-(OR2)p-in which each R2 represents an alkylene group containing from two to six carbon atoms, and p is a whole positive number from 1 to 5, inclusive, with the proviso that, when R1 represents said polyalkyleneoxy or phenylene group, m is 1. The compositions may contain as a second stabilizer, an organic sulphur compound of the type R1-Sx-R2 where \s3 is a whole number and R1 and R2 are similar or dissimilar organic groups bound to SX by carbon atoms, or an organic sulphur compound of the formula R1(R2)N-C(=S)-S-M-S-C(=S)-N(R2)R1, wherein M is a metal of Group II of the Periodic System and R1 and R2 are hydrocarbon groups having from 1 to 6 carbon atoms, or a trialkyltrithiophosphite having 6 to 20 carbon atoms, or polymeric products such as polyalkoxyalkyl sulphides, polyalkoxyalkoxyalkyl sulphides or polyhydroxyalkyl sulphides. Specifications 847,824 and 893,896 are referred to.ALSO:The invention comprises a 3,5-dialkyl-4-hydroxybenzyl ether having the general formula <FORM:0932818/IV(a)/1> in which n = 0, m = 1, or n = 1 and m represents an integer from 1 to 5 inclusive, each R is an alkyl group containing from 3 to 8 carbon atoms, branched on the alpha carbon atom, R1 is (1) an unsubstituted aliphatic hydrocarbon group containing at least m + 1 carbon atoms connected to m + 1 hydroxybenzyloxy groups, or (2) a phenylene group, or (3) a polyalkyleneoxy group of the formula -R2-(O-R2)pin which each R2 represents an alkylene group containing from two to six carbon atoms, and p is a whole positive number from 1 to 5, inclusive, with the proviso that, when R1 represents said polyalkyleneoxy or phenylene group, m is 1. The novel ethers may be made by reacting the corresponding 3,5-dialkyl-4-hydroxybenzyl alcohol with itself or with either an unsubstituted aliphatic polyhydroxy alcohol having not more than 6 hydroxyl groups, or a dihydroxybenzene, or a polyalkylene-oxyglycol of the formula HO-R2-(OR2)p-OH in which R2 is an alkylene group containing from 2 to 6 carbon atoms and p is an integer from 1 to 5 inclusive, in the presence of an acid catalyst, e.g. sulphuric acid, hydrogen bromide or boron trifluoride. The reaction temperature is preferably within the range from 10 DEG to 100 DEG C. Lists of suitable starting materials are given. The ethers and polyethers represent a new class of antioxidants which may be used to stabilize fatty acids. Detailed examples describe the preparation of tri(3,5-di-tert. butyl-4-hydroxybenzyl) glyceryl ether, bis(3,5-di-tert. butyl-4-hydroxybenzyl) ether, di(3,5-di-tert. butyl-4-hydroxybenzyl) phenylene dioxy ether. Specifications 847,824 and 893,896 are referred to.ALSO:Foods are stabilized against oxidation by 3,5-dialkyl-4-hydroxybenzyl ethers of the formula <FORM:0932818/VI/1> wherein n is 0 and m is 1, n is 1 and m is an integer from 1 to 5 inclusive, each R is an alkyl group containing from 3 to 8 carbon atoms, branched on the alpha carbon atom, R1 is (1) an unsubstituted aliphatic hydrocarbon group containing at least m+1 carbon atoms, connected to m+1 hydroxybenzyloxy groups, or (2) a phenylene group, or (3) a polyalkyleneoxy group of the formula -R2-(OR2)pin which each R2 represents an alkylene group containing from two to six carbon atoms, and p is a whole positive number from 1 to 5, inclusive, with the proviso that, when R1 represents said polyalkyleneoxy or phenylene group, m is 1. The compositions may contain as a second stabilizer, an organic sulphur compound of the type R1-Sx-R2 where x is a whole number and R1 and R2 are similar or dissimilar organic groups bound to Sx by carbon atoms, or an organic sulphur compound of the formula R1(R2)N-C(=S)-S-M-S-C(=S)-N(R2)R1, wherein M is a metal of Group II of the Periodic System and R1 and R2 are hydrocarbon groups having from 1 to 6 carbon atoms, or a trialkyltrithiophosphite having 6 to 20 carbon atoms, or polymeric products such as polyalkoxyalkylsulphides, polyalkoxyalkoxyalkylsulphides or polyhydroxyalkylsulphides. Specifications 847,824 and 893,896 are referred to.
GB35552/61A 1960-10-03 1961-10-02 Novel antioxidant 3,5-dialkyl-4-hydroxybenzyl ethers and their preparation Expired GB932818A (en)

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DE (1) DE1184763B (en)
FR (1) FR1316500A (en)
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NL (1) NL269799A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3346648A (en) * 1961-09-01 1967-10-10 Ethyl Corp Benzyl ethers
FR2378090A1 (en) * 1977-01-21 1978-08-18 Shell Int Research Non-acid lubricant contg. sulphur-contg. ester - and phenol or amine antioxidant, giving better antioxidant properties at high temp.
WO2016095735A1 (en) * 2014-12-15 2016-06-23 绍兴瑞康生物科技有限公司 Multifunctional synergistic macromolecular anti-oxidation stabilizer and preparation method and use thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2838571A (en) * 1955-03-21 1958-06-10 Ethyl Corp 3, 5-dialkyl-4-hydroxybenzyl ethers
FR1249844A (en) * 1959-09-24 1961-01-06 Eastman Kodak Co New composition of matter stabilized by an antioxidant of the 4, 4'-alkylene-dioxy-bis (alkylphenols) type and method of stabilization of oxidizable organic compounds
FR1256229A (en) * 1960-04-05 1961-03-17 Ethyl Corp New antioxidant compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3346648A (en) * 1961-09-01 1967-10-10 Ethyl Corp Benzyl ethers
FR2378090A1 (en) * 1977-01-21 1978-08-18 Shell Int Research Non-acid lubricant contg. sulphur-contg. ester - and phenol or amine antioxidant, giving better antioxidant properties at high temp.
WO2016095735A1 (en) * 2014-12-15 2016-06-23 绍兴瑞康生物科技有限公司 Multifunctional synergistic macromolecular anti-oxidation stabilizer and preparation method and use thereof
JP2018507270A (en) * 2014-12-15 2018-03-15 紹興瑞康生物科技有限公司 Multifunctional cooperative polymer antioxidant stabilizer and its preparation method and application

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NL269799A (en) 1964-06-25
DE1184763C2 (en) 1965-09-02
BE608758A (en) 1962-04-02
FR1316500A (en) 1963-02-01

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