GB874877A - Metal salts of organic dithiophosphates and lubricating compositions containing them - Google Patents

Metal salts of organic dithiophosphates and lubricating compositions containing them

Info

Publication number
GB874877A
GB874877A GB2388/59A GB238859A GB874877A GB 874877 A GB874877 A GB 874877A GB 2388/59 A GB2388/59 A GB 2388/59A GB 238859 A GB238859 A GB 238859A GB 874877 A GB874877 A GB 874877A
Authority
GB
United Kingdom
Prior art keywords
zinc
dithiophosphate
oil
alkyl radical
chlorine
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
GB2388/59A
Inventor
Victor Charles Ernest Burnop
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering Co
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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to GB2388/59A priority Critical patent/GB874877A/en
Priority to US860715A priority patent/US3087950A/en
Publication of GB874877A publication Critical patent/GB874877A/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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • 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
    • 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
    • C10M2223/042—Metal 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
    • 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
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Abstract

The invention comprises compounds having the general formula:- <FORM:0874877/IV (b)/1> wherein R1 is a C2-C24 alkyl radical, R2 is a C2-C24 alkyl radical in which one or more of the hydrogen atoms are replaced by chlorine atoms and M is zinc or cadmium. They may be obtained by reacting equimolar proportions of a C2-C24 alkanol and a C2-C24 chlorine-containing alkanol with phosphorus pentasulphide at elevated temperature and reacting the product thus obtained with the oxide, hydroxide or carbonate of zinc or cadmium. Suitable chlorine-containing alkanols are ethylene chlorhydrin, di- or trichlorethanol, 2-chloropropanol-1, 2,2,3-trichlorobutanol-1 and 5-chloro-pentanol-1. The products may be complexed with amines, preferably with tertiary alkyl primary amines. Examples are given for the production of (1) zinc chloroethyloctyl dithiophosphate, and (2) zinc chloroethyl ceto-stearyl dithiophosphate and of the complex of (1) with a mixture of isomeric tertiary alkyl primary amines in which the alkyl groups contain from 16 to 24 carbon atoms. The products are useful as additives for lubricating oils (see Group III).ALSO:A lubricating composition comprises a major proportion by weight of a lubricating oil containing a minor proportion by weight of a dithiophosphate of the formula:- <FORM:0874877/III/1> where R1 is a C2-C24 alkyl radical, R2 is a C2-C24 alkyl radical in which one or more of the hydrogen atoms are replaced by chlorine atoms and M is zinc or cadmium (see Group IV(b)) or of a complex of said dithiophosphate with an amine, especially a tertiary alkyl primary amine. The lubricating oil may be a mineral oil or a synthetic oil which may be a polymer oil or an ester oil, e.g. a dicarboxylic ester or ester of a phosphorus acid. Other aditives such as antioxidants, and detergent or viscosity improving additives may also be present. Specified additives are (1) zinc chloroethyl dithiophosphate and a complex thereof with a mixture of isomeric tertiary C16-C24 alkyl primary amines and (2) zinc chloroethyl ceto-stearyl dithiophosphate.
GB2388/59A 1959-01-22 1959-01-22 Metal salts of organic dithiophosphates and lubricating compositions containing them Expired GB874877A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2388/59A GB874877A (en) 1959-01-22 1959-01-22 Metal salts of organic dithiophosphates and lubricating compositions containing them
US860715A US3087950A (en) 1959-01-22 1959-12-21 Extreme pressure lubricant additive

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2388/59A GB874877A (en) 1959-01-22 1959-01-22 Metal salts of organic dithiophosphates and lubricating compositions containing them

Publications (1)

Publication Number Publication Date
GB874877A true GB874877A (en) 1961-08-10

Family

ID=9738673

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2388/59A Expired GB874877A (en) 1959-01-22 1959-01-22 Metal salts of organic dithiophosphates and lubricating compositions containing them

Country Status (2)

Country Link
US (1) US3087950A (en)
GB (1) GB874877A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3254025A (en) * 1961-08-18 1966-05-31 Lubrizol Corp Boron-containing acylated amine and lubricating compositions containing the same
EP0743354A1 (en) * 1993-12-30 1996-11-20 Tonen Corporation Lubricating oil composition
WO2001072759A1 (en) * 2000-03-24 2001-10-04 E. I. Du Pont De Nemours And Company Fluorinated lubricant additives
CN102887918A (en) * 2011-07-20 2013-01-23 中国石油天然气股份有限公司 Preparation and application of dialkyl dithiophosphate hydroxyl derivative and boric acid ester thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1198060A (en) * 1966-11-10 1970-07-08 British Petroleum Co Zinc Complexes
US3910976A (en) * 1971-08-04 1975-10-07 Dart Ind Inc Halo derivatives of vanadium organophosphates

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2899388A (en) * 1959-08-11 Calcium base grease containing a nickel
BE510012A (en) * 1951-03-29
US2838555A (en) * 1951-10-12 1958-06-10 Lubrizol Corp Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids
US2737492A (en) * 1952-03-26 1956-03-06 American Cyanamid Co Lubricating oil compositions
US2884431A (en) * 1956-06-08 1959-04-28 Exxon Research Engineering Co Fluorinated diesters of phosphorodithioic acid and salts thereof
US2906731A (en) * 1957-04-03 1959-09-29 Monsanto Chemicals Butyl rubber and phosphorothioates
US2923682A (en) * 1957-09-17 1960-02-02 Exxon Research Engineering Co Lubricating compositions containing mixed salts

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3254025A (en) * 1961-08-18 1966-05-31 Lubrizol Corp Boron-containing acylated amine and lubricating compositions containing the same
EP0743354A1 (en) * 1993-12-30 1996-11-20 Tonen Corporation Lubricating oil composition
EP0743354A4 (en) * 1993-12-30 1997-01-22 Tonen Corp Lubricating oil composition
WO2001072759A1 (en) * 2000-03-24 2001-10-04 E. I. Du Pont De Nemours And Company Fluorinated lubricant additives
US6541430B1 (en) 2000-03-24 2003-04-01 E. I. Du Pont De Nemours And Company Fluorinated lubricant additives
US6764984B2 (en) 2000-03-24 2004-07-20 E. I. Du Pont De Nemours And Company Fluorinated lubricant additives
CN102887918A (en) * 2011-07-20 2013-01-23 中国石油天然气股份有限公司 Preparation and application of dialkyl dithiophosphate hydroxyl derivative and boric acid ester thereof

Also Published As

Publication number Publication date
US3087950A (en) 1963-04-30

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