GB716343A - Mixed diesters of dithiophosphoric acids, zinc salts thereof and lubricating oil compositions of these zinc salts - Google Patents

Mixed diesters of dithiophosphoric acids, zinc salts thereof and lubricating oil compositions of these zinc salts

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Publication number
GB716343A
GB716343A GB5686/52A GB568652A GB716343A GB 716343 A GB716343 A GB 716343A GB 5686/52 A GB5686/52 A GB 5686/52A GB 568652 A GB568652 A GB 568652A GB 716343 A GB716343 A GB 716343A
Authority
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United Kingdom
Prior art keywords
carbon atoms
zinc salts
diesters
butyl
zinc
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
GB5686/52A
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.)
California Research LLC
Original Assignee
California Research LLC
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Filing date
Publication date
Application filed by California Research LLC filed Critical California Research LLC
Publication of GB716343A publication Critical patent/GB716343A/en
Expired legal-status Critical Current

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    • 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 Table
    • 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
    • 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 Table
    • 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
    • C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
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    • 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
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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    • 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
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    • C10M2207/02—Hydroxy compounds
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    • C10M2209/086—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 polycarboxylic, e.g. maleic acid
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2211/08—Halogenated waxes
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    • 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
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    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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

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

Abstract

The invention comprises mixed diesters of dithiophosphoric acid made by reacting phosphorus pentasulphide with a blend consisting of two different monohydric aliphatic alcohols, one of which contains not more than 4 carbon atoms and the other from 6 to 18 carbon atoms, and the zinc salts produced from the diesters. Many alcohols are specified for use, representative being methyl, propyl, sec.- and tert.-butyl as those of not more than 4 carbon atoms with hexyl, ethylisopropylcarbinol, 2-ethyl amyl, iso-octyl, undecyl and octadecyl as others of 6-18 carbon atoms. The mol. ratio of lower to higher alcohols in the blend may be 1 to 5 although for lubricants (see Group III) a ratio of 2 to 4 is preferred. Reaction temperatures of 120-200 DEG F. are mentioned. The zinc salts are obtained from the diesters by heating with zinc oxide. In examples, diesters are obtained by heating phosphorus pentasulphide with (1) isopropyl alcohol and methylisobutylcarbinol and (2) sec.-butyl alcohol and methylisobutylcarbinol and zinc salts prepared from each product on heating with zinc oxide.ALSO:The invention comprises an oil of lubricating viscosity containing zinc salts of mixed diesters of dithiophosphoric acid obtainable by reacting phosphorus pentasulphide with a blend consisting of two different monohydric aliphatic alcohols, one of which contains not more than 4 carbon atoms and the other from 6-18 carbon atoms. Many alcohols are specified for use, representative being methyl, propyl, sec. and tert.-butyl as those of not more than 4 carbon atoms with hexyl, ethylisopropyl carbinol, 2-ethylamyl, iso-octyl undecyl and octadecyl as others of 6-18 carbon atoms. A mol. ratio of lower to higher alcohols of 2 to 4 is preferred. The zinc salts are obtained from the diesters by treatment with zinc oxide. Lubricating oils mentioned include naphthenic and paraffin base oils, mixed base mineral oils, alkylene polymers, alkylene oxide polymers, dicarboxylic acid esters, phosphorus esters, silicate fluids and many members of these classes are specified. Preferably 0.05-2.0 per cent. by weight of additive is used but concentrates containing 50 or more per cent. may be prepared. Engine tests are given showing the anti-oxidative effect and the effect on the Inhibition Period of zinc butyl methylisobutyl carbinol dithiophosphate in mineral oils optionally containing a sulphurized alkyl-substituted calcium phenate. The zinc salts may be used in conjunction with other additives those specified being phenates, e.g. calcium cetyl phenate, sulphonates, e.g. calcium petroleum sulphonate, phenols, e.g. 2, 6-di-tertiary butyl-4-methyl phenol, phosphonates, e.g. calcium white oil phosphonate, thiophosphonates, e.g. calcium cetyl thiophosphonate and sulphur containing paraffins, e.g. sulphurized diparaffin sulphide.
GB5686/52A 1951-03-29 1952-03-04 Mixed diesters of dithiophosphoric acids, zinc salts thereof and lubricating oil compositions of these zinc salts Expired GB716343A (en)

Applications Claiming Priority (1)

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US218281A US2680123A (en) 1951-03-29 1951-03-29 Zinc salt of mixed ester thiophosphates

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GB716343A true GB716343A (en) 1954-10-06

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US (2) US2680123A (en)
BE (1) BE510012A (en)
DE (1) DE1097606B (en)
FR (1) FR1057074A (en)
GB (1) GB716343A (en)
NL (1) NL85589C (en)

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EP1529829A1 (en) * 2003-11-06 2005-05-11 Afton Chemical Corporation Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
US7368596B2 (en) 2003-11-06 2008-05-06 Afton Chemical Corporation Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties
US7592490B2 (en) 2003-11-06 2009-09-22 Afton Chemical Corporation Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties

Also Published As

Publication number Publication date
US2680123A (en) 1954-06-01
NL85589C (en)
BE510012A (en)
DE1097606B (en) 1961-01-19
US2689220A (en) 1954-09-14
FR1057074A (en) 1954-03-04

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