GB911958A - 3,5-dialkyl-4-hydroxybenzylthio compounds - Google Patents
3,5-dialkyl-4-hydroxybenzylthio compoundsInfo
- Publication number
- GB911958A GB911958A GB10045/61A GB1004561A GB911958A GB 911958 A GB911958 A GB 911958A GB 10045/61 A GB10045/61 A GB 10045/61A GB 1004561 A GB1004561 A GB 1004561A GB 911958 A GB911958 A GB 911958A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxybenzyl
- sulphide
- tert
- butyl
- carbon atoms
- 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
Links
Classifications
-
- 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
- C11B5/0071—Preserving by using additives, e.g. anti-oxidants containing halogens, sulfur or phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- 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
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
- C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
-
- 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
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; 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
- 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)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Liquid fuels such as kerosine and gasoline, hydrocarbon oils and greases, petroleum waxes and natural waxes are stabilized against oxidative deterioration by the presence of a minor proportion of any of the compounds A2S, A2S2 and H-, R- or Acyl-S-A, wherein A is 3:5-dialkyl-4-hydroxybenzyl, R is alkyl of at least eight carbon atoms and the acyl radical has not more than twenty carbon atoms. In Example IX the following compounds were used to stabilize commercial gasoline of a stated composition:-3:5-di-tert. amyl-4-hydroxybenzyl mercaptan; 3-ethyl-5-tert. butyl-4-hydroxybenzyl nonadecyl sulphide; 3:5-di-cyclohexyl-4-hydroxybenzyl thiobutyrate; bis(3-isopropyl-5-butyl-4-hydroxybenzyl) sulphide; 3:5-di-ter. butyl-31:51-diisopropyl-4:41-dihydroxydibenzyl sulphide; bis(3:5-diisopropyl-4-hydroxybenzyl) disulphide.ALSO:Polyolefins and natural or synthetic rubbers are stabilized against oxidative deterioration by the presence of a minor proportion of any of the compounds A2S, A2S2 and H-, R- or Acyl-S-A, wherein A is 3:5-dialkyl-4-hydroxybenzyl, R is alkyl of at least eight carbon atoms and the acyl radical has not more than twenty carbon atoms. In Examples:-(VI) polypropylene was stabilized with 3:5-di-tert.-butyl-4-hydroxybenzyl mercaptan and the corresponding disulphide and the S-acetyl and -dodecyl derivatives; (VII) polyethylene with bis(3:5-di-tert.-butyl-4-hydroxybenzyl) sulphide, and (VIII) a synthetic polyisoprene rubber with 3-methyl-5-tert.-butyl-4-hydroxybenzyl n-hecadecyl sulphide, 3:5-diisopropyl-4-hydroxybenzyl thiopropionate, 3-sec.-butyl-5-tert.-octyl-4-hydroxybenzyl mercaptan and bis-(3:5-di-tert.-amyl-4-hydroxybenzyl)sulphide. Stabilization of SBR and polybutadiene is also mentioned.ALSO:The invention comprises compounds of formulae A2S, A2S2 and H-, R- or Acyl-S-A, wherein A is 3 : 5-dialkyl-4-hydroxybenzyl, R is alkyl of at least eight carbon atoms and the acyl radical has not more than twenty carbon atoms. Specifically claimed are 3 : 5-di-tertbutyl-4-hydroxybenzyl mercaptan, the corresponding sulphide and disulphide and the S-n-dodecyl and -acetyl derivatives. The various types are prepared as follows:- ASH and ASR by reaction of AX (X = halogen) with a metal hydrosulphide and mercaptide, respectively, in liquid phase at ambient temperature; AS-Acyl by reaction of ASH with an organic acid anhydride in pyridine; A2S2 by oxidation of ASH with iodine in a liquid solvent medium; A2S either by reaction of ASH with AOH in presence of strong acid or by reaction of a 2 : 6-dialkylphenol with bis(chloromethyl) sulphide. The compounds of the invention are used to stabilize organic materials subject to oxidative deterioration (see also Groups III and IV(a)), e.g. polymerizable liquid unsaturated monomers such as vinylbenzenes, acrylates and methylacrylates.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1666560A | 1960-03-22 | 1960-03-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB911958A true GB911958A (en) | 1962-12-05 |
Family
ID=21778304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10045/61A Expired GB911958A (en) | 1960-03-22 | 1961-03-20 | 3,5-dialkyl-4-hydroxybenzylthio compounds |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE601608A (en) |
GB (1) | GB911958A (en) |
NL (1) | NL262577A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1543957B1 (en) * | 1963-08-01 | 1971-02-11 | Uniroyal Inc | Process for the preparation of bis (hydroxydialkylbenzyl) sulfides |
DE1593821B1 (en) * | 1967-03-17 | 1971-08-05 | Advance Prod Gmbh | Process for the preparation of dialkyl hydroxybenzyl sulfides |
GB2193957A (en) * | 1986-07-28 | 1988-02-24 | Magyar Asvanyolaj Es Foeldgaz | Extreme pressure (EP) aromatic oniphide lubricating oil additive and process for preparing same |
EP1146038A1 (en) * | 2000-04-12 | 2001-10-17 | Kumho Monsanto, Inc. | Novel antioxidant and method of producing the same |
-
0
- BE BE601608D patent/BE601608A/xx unknown
- NL NL262577D patent/NL262577A/xx unknown
-
1961
- 1961-03-20 GB GB10045/61A patent/GB911958A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1543957B1 (en) * | 1963-08-01 | 1971-02-11 | Uniroyal Inc | Process for the preparation of bis (hydroxydialkylbenzyl) sulfides |
DE1593821B1 (en) * | 1967-03-17 | 1971-08-05 | Advance Prod Gmbh | Process for the preparation of dialkyl hydroxybenzyl sulfides |
GB2193957A (en) * | 1986-07-28 | 1988-02-24 | Magyar Asvanyolaj Es Foeldgaz | Extreme pressure (EP) aromatic oniphide lubricating oil additive and process for preparing same |
EP1146038A1 (en) * | 2000-04-12 | 2001-10-17 | Kumho Monsanto, Inc. | Novel antioxidant and method of producing the same |
Also Published As
Publication number | Publication date |
---|---|
BE601608A (en) | |
NL262577A (en) |
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