GB676712A - Sulphur-containing compounds and lubricating compositions containing them - Google Patents

Sulphur-containing compounds and lubricating compositions containing them

Info

Publication number
GB676712A
GB676712A GB930/50A GB93050A GB676712A GB 676712 A GB676712 A GB 676712A GB 930/50 A GB930/50 A GB 930/50A GB 93050 A GB93050 A GB 93050A GB 676712 A GB676712 A GB 676712A
Authority
GB
United Kingdom
Prior art keywords
sulphur
mono
alkenes
mixture
molecule
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
GB930/50A
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.)
RANDOLPH COLIN HAWORTH
Shell Refining and Marketing Co Ltd
Original Assignee
RANDOLPH COLIN HAWORTH
Shell Refining and Marketing Co 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
Application filed by RANDOLPH COLIN HAWORTH, Shell Refining and Marketing Co Ltd filed Critical RANDOLPH COLIN HAWORTH
Priority to GB930/50A priority Critical patent/GB676712A/en
Publication of GB676712A publication Critical patent/GB676712A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B45/00—Formation or introduction of functional groups containing sulfur
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • C10M135/04—Hydrocarbons
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • 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
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated 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
    • C10M2207/26—Overbased carboxylic acid salts
    • C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
    • 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
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/08—Halogenated waxes
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • 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
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/02—Esters of silicic acids
    • 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

Abstract

Sulphur-containing compounds suitable for use as additives for lubricants are obtained by heating a mono-alkene containing at least 5 carbon atoms in the molecule or a mixture of such mono-alkenes with sulphur at between 100 DEG and 200 DEG C., preferably between 140 DEG and 180 DEG C., in the presence of a catalytic proportion of an organic vulcanizing accelerator, the molecular proportion of sulphur to mono-alkene or mixture of mono-alkenes being not more than 2 : 1. In calculating the molecular proportion of sulphur the sulphur molecule is deemed to be monoatomic. Specified alkenes are pentenes, hexenes, heptenes, octenes, decenes, tetradecenes, cetene, cerotene and melene or mixtures thereof, also the mixture of mono-alkenes obtained by the cracking or by the chlorination and dehydrochlorination of mineral oils or paraffin wax or by the dehydration of long-chain fatty alcohols. The reaction may be carried out under pressure and in an oxygen-free atmosphere, e.g. nitrogen. Specified vulcanization accelerators are 1-mercaptobenzthiazole and its substituted derivatives, benzthiazyl sulphides, alkyl xanthates, dithiocarbamates, aryl esters of the dithio acids such as 2,4-dinitrophenyl-piperidine carbothionolate and 2,4-dinitrophenyl-dialkyl dithiocarbamates and esters of the thiazoles with organic acids such as 1-benzthiazyl thiostearate or benzoate and 2,4 - dinitrophenyl - benzthiazyl sulphide. The more simple types may also be employed, e.g. aniline and thiocarbanilide and other organic bases such as piperidine, hexamethylene tetramine and the guanidines such as diphenylguanidine. Metal - containing vulcanizing accelerators such as the zinc dialkyl dithiocarbamates cannot be used where the presence of metal would prove undesirable in the final product unless some suitable means of removing the metal is employed. The use of about 0.5 to 10 per cent of vulcanization accelerator based on the total weight of sulphur and hydrocarbons gives good results. The reaction products may be purified by distillation under vacuum or by steam distillation under vacuum. In examples: (1) a mixture of mono-alkenes containing 6 carbon atoms in the molecule (obtained by the fractional distillation of cracked paraffin wax products) are heated with sulphur and 1-mercapto-benzthiazole in an autoclave at 140 DEG C. for 16 hours; the product is stated to be free from sulphides other than the tetrasulphide, whereas if the accelerator is omitted the product would contain penta- and hexa-sulphides; (2) a mixture of mono-alkenes containing 9 carbon atoms in the molecule (obtained by the fractional distillation of products obtained by the cracking of paraffin wax) is heated with sulphur and zinc diethyl dithiocarbamate at 142 DEG C. and atmospheric pressure for 10 hours, the reaction mixture being then cooled and filtered to remove the zinc in the vulcanizing accelerator; (3) a mixture of mono-alkenes containing 18 to 20 carbon atoms (obtained by the fractional distillation of a product obtained by cracking paraffin wax) is heated with sulphur and 1-mercapto-benzthiazole at 140 DEG C. for 9 hours. Specification 607,765 is referred to.ALSO:A lubricating composition comprises a mineral lubricating oil or a lubricating grease and a small proportion of a sulphur-containing compound obtained by heating a mono-alkene containing at least 5 carbon atoms in the molecule or a mixture of such mono-alkenes with sulphur at between 100 DEG C and 200 DEG C in the presence of a catalytic proportion of an organic vulcanizing accelerator, the molecular proportion of sulphur to mono-alkene or mixture of mono-alkenes being not more than 2:1 (see Group IV(b)). The sulphurated hydrocarbons may be added in such quantities as to yield lubricants having sulphur contents of 0.01 per cent to 5.0 per cent, generally about 0.1 per cent. The lubricating compositions may contain pourpoint depressors such as alkylated napthalenes, thickeners such as soaps and inorganic gels, oxidation inhibitors such as 2,4-dimethyl-6-tertiary butyl phenol and 2.6-di-tertiary butyl-4-methyl phenol, sludge dispersers such as oil soluble metal soaps and oil soluble metal phenates, anti-corrosion agents such as polycarboxylic acids obtained by condensing alkenes with maleic acid, viscosity index improvers such as polyisobutylenes and methyl methacrylate polymers, foam preventing agents such as polymeric organic silicones and metasilicates and antiring sticking agents such as basic metal soaps of alkylated salicylic acids. Other extreme pressure additives such as halogen and phosphorus containing compounds may also be used in conjunction with the sulphurated compounds, e.g. such compounds as chlorinated paraffin wax, calcium dichlorostearate, tricresyl phosphate, trichlorophenyl phosphate or 2,4-di(trichloromethyl)-6-nitro-1,3-benzodioxane.
GB930/50A 1950-01-13 1950-01-13 Sulphur-containing compounds and lubricating compositions containing them Expired GB676712A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB930/50A GB676712A (en) 1950-01-13 1950-01-13 Sulphur-containing compounds and lubricating compositions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB930/50A GB676712A (en) 1950-01-13 1950-01-13 Sulphur-containing compounds and lubricating compositions containing them

Publications (1)

Publication Number Publication Date
GB676712A true GB676712A (en) 1952-07-30

Family

ID=9713020

Family Applications (1)

Application Number Title Priority Date Filing Date
GB930/50A Expired GB676712A (en) 1950-01-13 1950-01-13 Sulphur-containing compounds and lubricating compositions containing them

Country Status (1)

Country Link
GB (1) GB676712A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3007870A (en) * 1958-12-31 1961-11-07 Exxon Research Engineering Co Lubricating oil compositions containing sulfurized olefins and mixed salts
WO1987000833A1 (en) * 1985-07-29 1987-02-12 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates, lubricating oils, metal working lubricants and asphalt compositions containing same
EP0420453A1 (en) * 1989-09-27 1991-04-03 Mobil Oil Corporation Sulphur coupled hydrocarbyl derived mercaptobenzothiazole adducts as multifunctional antiwear additives and compositions containing same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3007870A (en) * 1958-12-31 1961-11-07 Exxon Research Engineering Co Lubricating oil compositions containing sulfurized olefins and mixed salts
WO1987000833A1 (en) * 1985-07-29 1987-02-12 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates, lubricating oils, metal working lubricants and asphalt compositions containing same
US4740322A (en) * 1985-07-29 1988-04-26 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates, lubricating oils, metal working lubricants and asphalt compositions containing same
EP0420453A1 (en) * 1989-09-27 1991-04-03 Mobil Oil Corporation Sulphur coupled hydrocarbyl derived mercaptobenzothiazole adducts as multifunctional antiwear additives and compositions containing same
US5073279A (en) * 1989-09-27 1991-12-17 Mobil Oil Corporation Sulfur coupled hydrocarbyl derived mercaptobenzothiazole adducts as multifunctional antiwear additives and compositions containing same

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