GB690327A - Improvements in or relating to lubricating compositions - Google Patents

Improvements in or relating to lubricating compositions

Info

Publication number
GB690327A
GB690327A GB3168/48A GB316848A GB690327A GB 690327 A GB690327 A GB 690327A GB 3168/48 A GB3168/48 A GB 3168/48A GB 316848 A GB316848 A GB 316848A GB 690327 A GB690327 A GB 690327A
Authority
GB
United Kingdom
Prior art keywords
phosphorus
sulphur
sulphide
acids
sulphurized
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
GB3168/48A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB690327A publication Critical patent/GB690327A/en
Expired legal-status Critical Current

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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/16Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-nitrogen bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026Butene
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16Paraffin waxes; Petrolatum, e.g. slack wax
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/02Hydroxy compounds
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    • C10M2207/027Neutral salts thereof
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125Carboxylix 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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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/12Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/141Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/142Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
    • C10M2207/14Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/144Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2207/10Carboxylix acids; Neutral salts thereof
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    • C10M2207/146Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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    • C10M2207/22Acids obtained from polymerised unsaturated acids
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    • C10M2207/40Fatty vegetable or animal oils
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    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/082Macromolecular 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 monocarboxylic
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    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/101Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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    • C10N2010/16Groups 8, 9, or 10
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2060/00Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04Oxidation, e.g. ozonisation

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  • Organic Chemistry (AREA)
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  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

Phosphorus- and sulphur-containing reaction products are prepared by reacting a phosphorus sulphide with a cyclic ketone having at least 12 carbon atoms. The ketone may be derived from the condensation of acetone to high molecular weight isophorone type fractions; the hydrogenated condensation products may also be used, and other ketones mentioned are dibutyl cyclohexanone, alkyl substituted carvomenthone, menthone, pulegone, carvone and camphor. The phosphorus sulphide may be phosphorus pentasulphide or heptasulphide. The molecular ratio of phosphorus sulphide to ketone may be from 1 : 2 to 1 : 1.2. The reaction product may be sulphurized, and before or after sulphurization may be treated with a metal compound, ammonia or an organic base to form a salt. Sulphurizing agents used may be sulphur, sulphur halides, alkali polysulphides, ammonium hydrogen sulphide and hydrogen sulphide. Metal compounds specified are the hydroxides, carbonates or oxides of the alkali, alkaline earth and heavy metals, a number of which are mentioned. In a typical example, a mixture of cyclic unsaturated ketones containing at least 18 carbon atoms derived from the condensation of acetone is heated with phosphorus pentasulphide in the ratio 8 : 4 in an atmosphere of carbon dioxide, first at 60-80 DEG C., and then for five hours at 160 DEG C. The product is extracted with a non-aromatic hydrocarbon of boiling range 164-233 DEG F., the solution filtered and the filtrate evaporated. The product obtained is dissolved in mineral oil, lime added and the mixture heated and then filtered to remove excess lime. The calcium salt may be sulphurized by heating with sulphur at 150-170 DEG C. in an inert atmosphere. The products are useful as additions to lubricants (see Group III).ALSO:A lubricating composition comprises a major proportion of a lubricating oil and a minor proportion of a phosphorus and sulphur containing product obtained by reacting a cyclic ketone having at least 12 carbon atoms with a phosphorus sulphide. The unsaturated cyclic ketones derived from the condensation of acetone or diisobutyl ketone to high molecular weight isophorone type fractions or their hydrogenated products are preferably used; other ketones mentioned are dibutyl cyclohexanone, alkyl substituted carvomenthone, methone, pulegone, carvone and camphor. The phosphorus sulphide may be phosphorus pentasulphide or heptasulphide. The lubricating oil may be a mineral oil or a synthetic oil of the hydrocarbon or non-hydrocarbon type. The molecular ratio of phosphorus sulphide to ketone may be from 1 : 2 to 1 : 1.2 and preferably 0.1-2.0 per cent of the reaction product is used. The reaction product may be sulphurized, and before or after sulphurization may be treated with a metal compound, ammonia or an organic base to form a salt. Sulphurizing agents used may be sulphur, sulphur halides, alkali polysulphides, ammonium hydrogen sulphide and hydrogen sulphide. Metal compounds specified are the hydroxides, carbonates or oxides of the alkali, alkaline earth and heavy metals, a number of which are mentioned. In a typical example, a mixture of cyclic unsaturated ketones containing at least 18 carbon atoms derived from the condensation of acetone is heated with phosphorus pentasulphide in the ratio 8:4 in an atmosphere of carbon dioxide, first at 60 DEG -80 DEG C and then for five hours at 160 DEG C. The product is extracted with a non-aromatic hydrocarbon of boiling range 164 DEG -233 DEG F, the solution filtered and the filtrate evaporated. The product obtained is dissolved in mineral oil, lime added and the mixture heated and then filtered to remove excess lime. The lime salt recovered from the oil may be redissolved in oil and sulphurized by heating with sulphur. Optional additives mentioned are: detergents, for example salts of acids such as wool fat acids, paraffin wax acids, aromatic carboxylic acids, diphenol sulphides and sulphonic, sulphuric and phosphoric acids, for example calcium petroleum sulphonate or the calcium salt of an alkyl phenol-formaldehyde condensation product; non-metallic detergents such as lecithin and rapeseed oil; anti-oxidants such as alkyl-phenols, amino phenols and amines; corrosion inhibitors such as dicarboxylic acids, sulphonates and compounds such as d cyano stearic acid; extreme pressure agents such as esters of phosphorus acids, sulphides and disulphides, sulphurized fatty oils, sulphurized olefins and chlorinated hydrocarbons.
GB3168/48A 1947-02-04 1948-02-03 Improvements in or relating to lubricating compositions Expired GB690327A (en)

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US726445A US2482762A (en) 1947-02-04 1947-02-04 Lubricating compositions

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GB690327A true GB690327A (en) 1953-04-15

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GB3168/48A Expired GB690327A (en) 1947-02-04 1948-02-03 Improvements in or relating to lubricating compositions

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6583092B1 (en) * 2001-09-12 2003-06-24 The Lubrizol Corporation Lubricating oil composition

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2242260A (en) * 1937-01-22 1941-05-20 Lubri Zol Dev Corp Lubricating composition
US2419153A (en) * 1943-04-09 1947-04-15 Standard Oil Co Lubricant and the like
US2383497A (en) * 1943-07-08 1945-08-28 Socony Vacuum Oil Co Inc Mineral oil composition

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