GB865970A - Organic molybdenum blue derivatives and mineral lubricating oils containing them - Google Patents

Organic molybdenum blue derivatives and mineral lubricating oils containing them

Info

Publication number
GB865970A
GB865970A GB2085957A GB2085957A GB865970A GB 865970 A GB865970 A GB 865970A GB 2085957 A GB2085957 A GB 2085957A GB 2085957 A GB2085957 A GB 2085957A GB 865970 A GB865970 A GB 865970A
Authority
GB
United Kingdom
Prior art keywords
sulphur
molybdenum blue
organic
molybdenum
glyoxalidine
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
GB2085957A
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.)
Alpha Molykote Corp
Original Assignee
Alpha Molykote 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 Alpha Molykote Corp filed Critical Alpha Molykote Corp
Publication of GB865970A publication Critical patent/GB865970A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic System
    • C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic System compounds without a metal-carbon linkage
    • 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
    • C10M2207/021—Hydroxy compounds having hydroxy groups 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
    • 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
    • C10M2207/125—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
    • C10M2207/128—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 containing hydroxy groups; Ethers 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
    • C10M2207/129—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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C10M2215/224—Imidazoles
    • 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
    • C10M2215/26—Amines
    • 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
    • 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
    • C10M2219/083—Dibenzyl sulfide
    • 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
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
    • 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
    • C10M2227/09—Complexes with metals

Abstract

The invention comprises organic sulphurmolybdenum blue compounds obtainable by interaction of an olefinically unsaturated alcohol or an organic nitrogenous base, each having a hydrocarbon radical containing 8-20 carbon atoms, with sulphur and then with molybdenum. The compounds, which are lubricant additives (see Group III), are preferably prepared by reacting the alcohol or organic nitrogenous base with approximately equimolar amounts of sulphur at an elevated temperature and then reacting the product, preferably in molar excess with molybdenum blue. There are also described as components of a lubricating oil composition organic molybdenum blue compounds prepared by reacting the above-defined alcohols or nitrogenous bases with molybdenum blue in isobutanol solution, distilling off the butanol on a water-bath followed by heating of the residue. The sulphur-containing additives may be rendered resistant to thermal decomposition by addition of a fatty acid containing at least 12 carbon atoms, or a reaction product thereof with an organic nitrogenous base such as oleic acid or its reaction product with 1-hydroxy ethyl-2-heptadecenyl glyoxalidine. In Examples: (1) the above-mentioned glyoxalidine is heated with elementary sulphur at 130-150 DEG C., the sulphurised base is dissolved in an isobutanolic solution of molybdenum blue and the mixture heated to remove the alcohol leaving an organic sulphur molybdenum blue as residue; (2) various sulphur-free organic molybdenum blues are prepared by adding hexadecenol, oleylamine, dehydroabietylamine and 1-hydroxyethyl-2-heptadecenyl glyoxalidine to separate solutions of molybdenum blue in isobutanol, each mixture then being stripped of alcohol under reduced pressure and further heated. Other specified unsaturated alcohols and nitrogenous bases are tetradecenol, octadecenol, octylamine, 1-hydroxyethyl-2-heptadecyl glyoxalidine, the reaction products of ethylene oxide with an amine such as actodecyclamine, and nitrogenous bases generally which are obtainable by condensing amino alcohols with higher fatty acids.ALSO:Mineral lubricating oil compositions comprise about 0.5 to 5% by weight of an organic sulphur-containing molybdenum blue compound obtainable by interaction of sulphur with an olefinically unsaturated alcohol or an organic nitrogenous base, each having a hydrocarbon radical containing 8-20 carbon atoms, and then with molybdenum blue. In a modification, the composition comprises about 0.5-5% by weight of a sulphur-free reaction product of molybdenum blue with an alcohol or nitrogenous base as defined above, and in addition elementary sulphur or an oil-soluble organic sulphur compound which liberates sulphur at the temperature created by lubricating friction. The compositions may also contain, as oil-solubilisers, alcohols containing 8-20 carbon atoms. The first-mentioned compositions may contain fatty acids containing at least 12 carbon atoms, or reaction products thereof with organic nitrogenous bases, to render the molybdenum blue additives heat-resistant. Examples describe mineral oil compositions containing (1) an organic sulphurcontaining molybdenum blue, obtained by sulphurising 1 - hydroxyethyl - 2 - heptadecenyl glyoxalidine and reacting the product with molybdenum blue, and oil-solubilising alcohols containing 14-18 carbon atoms and also optionally oleic acid or its reaction product with the above-named glyoxalidine; or (2) sulphur or dibenzyl disulphide and a sulphur-free organic molybdenum blue prepared from hexadecenol, dehydroabietylamine, oleylamine or the above-named glyoxalidine. The additives have extreme-pressure properties. The additives may also be derived from tetradecenol, octadecenol, octylamine, 1-hydroxyethyl-2-heptadecyl glyoxalidine, reaction products of ethylene oxide with octadecylamine and like amines, and nitrogenous bases generally which are obtainable by condensing amino-alcohols with higher fatty acids. Molybdenum blue is prepared by reacting metallic molybdenum with a solution of MoO3 in aqueous sulphuric acid and extracting the resulting molybdenum blue with isobutanol.
GB2085957A 1956-07-04 1957-07-02 Organic molybdenum blue derivatives and mineral lubricating oils containing them Expired GB865970A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA25244A DE1060079B (en) 1956-07-04 1956-07-04 Lubricants containing molybdenum

Publications (1)

Publication Number Publication Date
GB865970A true GB865970A (en) 1961-04-26

Family

ID=6925862

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2085957A Expired GB865970A (en) 1956-07-04 1957-07-02 Organic molybdenum blue derivatives and mineral lubricating oils containing them

Country Status (3)

Country Link
DE (1) DE1060079B (en)
FR (1) FR1177451A (en)
GB (1) GB865970A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3234129A (en) * 1962-08-01 1966-02-08 Ethyl Corp Lubricating compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4164473A (en) 1977-10-20 1979-08-14 Exxon Research & Engineering Co. Organo molybdenum friction reducing antiwear additives
US5137647A (en) * 1991-12-09 1992-08-11 R. T. Vanderbilt Company, Inc. Organic molybdenum complexes

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2291C (en) * G. LILIENTHAL, Ingenieur, in Berlin Cutting machine with knife disc
FR1099953A (en) * 1954-01-06 1955-09-14 Inst Francais Du Petrole Hydrocarbon soluble molybdenum blue
FR1099955A (en) * 1954-01-07 1955-09-14 Inst Francais Du Petrole Lubricants based on molybdic xanthates suitable for use at high temperature and pressure

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3234129A (en) * 1962-08-01 1966-02-08 Ethyl Corp Lubricating compositions

Also Published As

Publication number Publication date
DE1060079B (en) 1959-06-25
FR1177451A (en) 1959-04-24

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