GB981644A - Sulfur and chlorine containing reaction products and applications thereof - Google Patents

Sulfur and chlorine containing reaction products and applications thereof

Info

Publication number
GB981644A
GB981644A GB46056/62A GB4605662A GB981644A GB 981644 A GB981644 A GB 981644A GB 46056/62 A GB46056/62 A GB 46056/62A GB 4605662 A GB4605662 A GB 4605662A GB 981644 A GB981644 A GB 981644A
Authority
GB
United Kingdom
Prior art keywords
phenol
products
butylphenol
tert
substituted
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
GB46056/62A
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 GB981644A publication Critical patent/GB981644A/en
Expired legal-status Critical Current

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    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • 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
    • C10L1/103—Liquid carbonaceous fuels containing additives stabilisation of anti-knock agents
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
    • C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S524/925—Natural rubber compositions having nonreactive materials, i.e. NRM, other than: carbon, silicon dioxide, glass titanium dioxide, water, hydrocarbon or halohydrocarbon

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

Abstract

Sulphurized chlorophenols are prepared by the action of sulphur dichloride on monoalkyl phenols substituted in the ortho-position to the hydroxyl group with an alkyl group of 1-12 carbon atoms, at least one mol., preferably 1.1-1.5 mols., of sulphur dichloride being used per mol. of phenol. The reaction may be effected at 0-100 DEG C., preferably at 40-65 DEG C., preferably in a solvent. Examples are given of the manufacture of products from 2-tert.-butylphenol, methods of purifying the products being indicated. Other phenols which may be treated are 2-n-hexylphenol, 2-n-butylphenol, 2-sec.-butylphenol, 2 - (31 - heptyl)phenol, 2 - n-propylphenol, 2 - isopropylphenyl, 2 - n - amylphenol, 2 - isobutylphenol, 2 - n - octylphenol, 2 - (31 - octyl)phenol, 2 - tert. - amylphenol, 2 - (21 - heptyl)phenol, 2 - (21 - hexyl)phenol and 2 - tert. - octylphenol. The products are useful as antioxidants.ALSO:As antioxidants, use is made of sulphurized chlorophenols prepared by the action of sulphur dichloride on monoalkyl phenols substituted in the ortho-position to the hydroxyl group with an alkyl group of 1-12 carbon atoms, at least one mol., preferably 1.1-1.5 mols., of sulphur dichloride being used per mol. of phenol. Examples are given of the manufacture of products from 2-tert.-butylphenol. Other phenols which may be treated are 2-n-hexylphenol, 2 - n - butylphenol, 2 - sec. - butylphenol, 2 - (31-heptyl) phenol, 2 - n - propylphenol, 2 - isopropylphenol, 2 - n - amylphenol, 2 - isobutylphenol, 2 - n - octylphenol, 2 - (31 - octyl)-phenol, 2 - tert. - amylphenol, 2 - (21 - heptyl)-phenol, 2-(21-hexyl)phenol and 2-tert.-octylphenol. The products may be applied to the treatment of olefine polymers and natural or synthetic rubber. The proportions of stabilizer may be up to 5%.ALSO:As antioxidants, use is made of sulphurized chlorophenols prepared by the action of sulphur dichloride on monoalkyl phenols substituted in the ortho-position to the hydroxyl group with an alkyl group of 1-12 carbon atoms, at least one mol., preferably 1.1-1.5 mols., of sulphur dichloride being used per mol. of phenol. The products may be applied to the treatment of lubricating oils and greases; hydrocarbon fuels; hydraulic fluids; fats and fatty oils such as linseed, codliver, castor, soybean, rapeseed, coconut, olive, palm, corn, sesame, peanut and babassu oils, lard and beef tallow; soaps; and petroleum waxes. Examples of the treatment of lubricating oils are given. The hydrocarbon fuels may contain organo-lead anti-knock agents and either cyclopentadienyl manganese tricarbonyl or cyclopentadienyl nickel nitrosyl. They may also contain halogen-scavengers and manganese pentacarbonyl. Concentrates of the anti-oxidants in hydrocarbon fuel compositions may be prepared. Examples of hydrocarbon fuel compositions are given. The hydraulic fluids may contain organic compounds of aluminium, calcium, lithium, barium, strontium or magnesium, e.g. alkaline-earth metal salts of phenyl-substituted long-chain fatty acids or of the capryl or octyl esters of salicylic acid or of petroleum sulphonic acids or of alkyl-substituted phenol sulphides, the aluminium and alkaline-earth metal salts of cetylphenol, metal salts of wax-substituted phenol derivatives, and reaction products of alkylphenols or alkylphenol sulphides and alkaline-earth metal oxides or hydroxides. The proportion of stabilizer may be up to 5%.
GB46056/62A 1961-12-22 1962-12-06 Sulfur and chlorine containing reaction products and applications thereof Expired GB981644A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US161357A US3129213A (en) 1961-12-22 1961-12-22 Orthoalkylphenol-sulfur dichloride reaction products

Publications (1)

Publication Number Publication Date
GB981644A true GB981644A (en) 1965-01-27

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Family Applications (1)

Application Number Title Priority Date Filing Date
GB46056/62A Expired GB981644A (en) 1961-12-22 1962-12-06 Sulfur and chlorine containing reaction products and applications thereof

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GB (1) GB981644A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3335104A (en) * 1962-06-22 1967-08-08 Stauffer Chemical Co Stabilization of crystalline polypropylene
US3365406A (en) * 1962-07-05 1968-01-23 Stauffer Chemical Co Stabilization of crystalline polypropylene with a combination of trialkyl phenol, dithio bis phenol and thiodipropionic esters
US3498936A (en) * 1964-05-27 1970-03-03 Hooker Chemical Corp Hydroxyalkylated phenol-sulfur halide resins and polyurethanes containing same
US3882082A (en) * 1972-05-08 1975-05-06 Ashland Oil Inc Stabilization of propylene polymers
US4056568A (en) * 1975-03-24 1977-11-01 Crown Zellerbach Corporation 2,6-Dialkyl-4-hydroxysulfenyl chlorides
US4393241A (en) * 1982-02-01 1983-07-12 Celanese Corporation Synthesis of alkoxy and phenoxy substituted aryl sulfides
US4877902A (en) * 1988-03-14 1989-10-31 Ethyl Corporation Polythiobisphenol process
US5004481A (en) * 1989-08-03 1991-04-02 Ethyl Corporation Fuel compositions containing sulfur-bridged phenolic antioxidants

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2239534A (en) * 1939-09-02 1941-04-22 Standard Oil Dev Co Polymerization and condensation products
US2362293A (en) * 1939-12-27 1944-11-07 Standard Oil Dev Co Lubricant
US2409687A (en) * 1943-05-10 1946-10-22 Standard Oil Dev Co Sulfur and metal containing compound
US2569122A (en) * 1947-12-22 1951-09-25 Shell Dev Lubricant
US2621172A (en) * 1949-02-02 1952-12-09 Sinclair Refining Co Compositions of matter from sulfur chlorides, bicyclic terpenes, phosphorus sulfides, and alkylated phenols or alcohols
FR1050806A (en) * 1952-02-13 1954-01-11 Renault Lubricants for heavily loaded components
US2767163A (en) * 1952-05-13 1956-10-16 Exxon Research Engineering Co Stabilized organic sulfur-containing compounds

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