GB670077A - Improved oxidation resisting compositions comprising mineral lubricating oils, and hydrocarbon polymers, synthetic rubbers and waxes - Google Patents

Improved oxidation resisting compositions comprising mineral lubricating oils, and hydrocarbon polymers, synthetic rubbers and waxes

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Publication number
GB670077A
GB670077A GB22971/48A GB2297148A GB670077A GB 670077 A GB670077 A GB 670077A GB 22971/48 A GB22971/48 A GB 22971/48A GB 2297148 A GB2297148 A GB 2297148A GB 670077 A GB670077 A GB 670077A
Authority
GB
United Kingdom
Prior art keywords
alcohols
hydrocarbon
oils
octyl
phenols
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
GB22971/48A
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.)
Standard Oil Development Co
Original Assignee
Standard Oil Development 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 Standard Oil Development Co filed Critical Standard Oil Development Co
Publication of GB670077A publication Critical patent/GB670077A/en
Expired legal-status Critical Current

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    • 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
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C—CHEMISTRY; METALLURGY
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/265—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen and/or sulfur bonds
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2691—Compounds of uncertain formula; reaction of organic compounds (hydrocarbons acids, esters) with Px Sy, Px Sy Halz or sulfur and phosphorus containing compounds
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
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    • C10M2201/04—Elements
    • C10M2201/041—Carbon; Graphite; Carbon black
    • C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
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    • C10M2201/06—Metal compounds
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
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    • C10M2205/20—Natural rubber; Natural resins
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    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)

Abstract

Cuprous thiophosphates of formula <FORM:0670077/IV (b)/1> where R and R1 are organic radicals which may be hydrocarbon, halogen-substituted hydrocarbon or nitro-substituted hydrocarbon radicals, the sum of the carbon atoms in aliphatic or cycloaliphatic groups in R and R1 being not less than 10 and X is oxygen or sulphur, are prepared by treating the corresponding thiophosphoric acid with cuprous oxide, preferably in the presence of a reducing agent and/or in an inert atmosphere. The thiophosphoric acid may be prepared by treating an appropriate alcohol, phenol, mercaptan or thiophenol with phosphorus pentasulphide. Alcohols mentioned are 2-ethylhexanol, methyl cyclohexanol, a mixture of C12 to C16 alcohols, normal straight-chain alcohols, alcohols derived from natural waxes or from the oxidation of petroleum hydrocarbons, lauryl, stearyl and oleyl alcohols, wool-fat alcohols, and sperm oil alcohols; alkylated phenols and naphthols such as amyl and octyl phenols, wax-alkylated phenols and petroleum phenols are also mentioned. The corresponding mercaptans and thiophenols may also be used, as well as a mixture of alcohols, such as a mixture of isopropanol and 2-ethylhexanol. In one example, 2-ethylhexanol is heated with phosphorus pentasulphide for 1 1/2 hours at 90 DEG C. After filtration the acid is added to a slurry of cuprous oxide and sodium hydrosulphite in benzene. The product is filtered, the filtrate is dissolved in mineral oil, and the benzene and water are removed by heating. The preparation of cuprous nonyl, octyl, methylcyclohexyl, isopropyl, ethyl-hexyl and C12-C16 alkyl secondary butyl thiophosphates is also described. Specification 601.586 is referred to.ALSO:Hydrocarbon products are mixed with a small proportion of a compound of formula <FORM:0670077/III/1> where R and R1 are organic radicals which may be hydrocarbon, halogen-substituted hydrocarbon and nitro substituted hydrocarbon radicals, the sum of the carbon atoms in aliphatic or cycloaliphatic groups in R and R1 being not less than 10, and where X is oxygen or sulphur. The tendency of the products to corrode metal surfaces and to undergo atmospheric oxidation is thus reduced. The hydrocarbon products may be hydrocarbon lubricating oils, hydrocarbon fuels such as Diesel fuel and kerosene, synthetic rubbers and hydrocarbon waxes. The hydrocarbon oils may be mineral oils or synthetic oils such as those prepared by the polymerisation of olefins, and mixtures of mineral oils with animal, vegetable and fish oils may also be used. The alcohol from which the thiophosphoric acid is derived may be 2-ethylhexanol, methylcyclohexanol, a mixture of C12 to C16 alcohols, normal straight-chain alcohols, alcohols derived from natural waxes or from the oxidation of petroleum hydrocarbons, lauryl, stearyl and oleyl alcohols, wool-fat alcohols and sperm oil alcohols; alkylated phenols and naphthols such as amyl and octyl phenols, wax-alkylated phenols and petroleum phenols are also mentioned. The corresponding mercaptans or thiophenols may also be used. Additives specified are cuprous methylcyclohexyl, 2-ethylhexyl, nonyl, octyl, isopropyl-ethylhexyl and C12-C16 alkyl - secondary butyl thiophosphates. These compounds are compared in their effects with sodium, potassium and calcium ethylhexyl thiophosphates. From 0.02 to about 3 per cent of the additives may be used. Detergents such as soaps, sulphonates, phenates, alcoholates, carboxylates, alkyl phenol sulphides, organo phosphates, other thiophosphates, phosphites and thiophosphites, salicylates, xanthates, thioxanthates, thiocarbamates, amines, reaction products of phenates and sulphur or phosphorus sulphides may also be added to the compositions. Examples of such detergents include barium tert. octyl phenol sulphide, nickel oleate, aluminium naphthenate, calcium phenyl stearate, calcium petroleum sulphonate and zinc methyl cyclohexyl thiophosphate. In the case of hydrocarbon lubricating compositions, other optional ingredients are dyes, pour point depressors, heat-thickened fatty oils, sulphurised fatty oils, organo-metallic compounds, sludge - dispersers, anti-oxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber olefin polymers, voltolized fats, voltolized mineral oils or voltolized waxes, graphite, zinc oxide, solvents and assisting agents. Assisting agents particularly mentioned are the higher alcohols, for example octyl, lauryl, cetyl, stearyl, heptadecyl, oleyl, napthenic, phenyl octyl and octadecyl benzyl alcohols, wool fat and sperm oil alcohols, and alcohols produced by the oxidation of petroleum hydrocarbons. Specification 601,586 is referred to.
GB22971/48A 1947-11-28 1948-08-31 Improved oxidation resisting compositions comprising mineral lubricating oils, and hydrocarbon polymers, synthetic rubbers and waxes Expired GB670077A (en)

Applications Claiming Priority (1)

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US788670A US2552570A (en) 1947-11-28 1947-11-28 Oxidation resisting hydrocarbon products

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GB670077A true GB670077A (en) 1952-04-16

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GB22971/48A Expired GB670077A (en) 1947-11-28 1948-08-31 Improved oxidation resisting compositions comprising mineral lubricating oils, and hydrocarbon polymers, synthetic rubbers and waxes

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US (1) US2552570A (en)
FR (1) FR971155A (en)
GB (1) GB670077A (en)
NL (1) NL72745C (en)

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US2552570A (en) 1951-05-15
FR971155A (en) 1951-01-15

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