Classifications

• • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid 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
  • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
  • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
  • C10M129/68—Esters
  • C10M129/70—Esters of monocarboxylic 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
• • 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
• • 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
  • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
  • C10M2207/282—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
  • C10M2207/283—Esters of polyhydroxy compounds
• • 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
  • C10M2207/286—Esters of polymerised unsaturated 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
  • C10M2211/044—Acids; Salts or esters 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/06—Perfluorinated compounds
• • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/08—Resistance to extreme temperature
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/12—Gas-turbines
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/12—Gas-turbines
  • C10N2040/13—Aircraft turbines

Definitions

• the invention is concerned with'liquid hydrocarbon oil compositions having improved resistance against the formation therein of insoluble material.
• liquid hydrocarbon oils such as lubricating oils, especially fuels, e.g. middle distillate fuels and hydrotreated lubricating oils tend to form insoluble material during use especially at high temperatures e.g. at temperatures of at least 100°C.
• esters of olefinically unsaturated carboxylic acids reduce the amount of insoluble material formed in liquid hydrocarbon oils.
• the invention is concerned with a liquid hydrocarbon oil composition
• a liquid hydrocarbon oil composition comprising a major proportion of a liquid hydrocarbon oil and a minor proportion of a C 8 to C50 hydrocarbyl ester of an olefinically unsaturated carboxylic acid.
• the hydrocarbyl group of the ester is suitably an alkyl group, preferably a C 10 to C 30 alkyl group.
• the alkyl group may be linear or branched, with substantially linear alkyl groups being preferred.
• the hydrocarbyl group may be substituted or interrupted e.g. with one or more halo-, oxy-, nitrogen- or sulphur-containing groups or atoms.
• the esters may be derived from olefinically unsaturated monocarboxylic acids i.e. acids having the general formula: and/or one or more olefinically unsaturated dicarboxylic acids such as fumaric or maleic acid i.e. acids having the general formula: wherein, in both formulae, n is an integer suitably of from 2 to 10, preferably of from 2 to 6.
• esters are those derived from olefinically unsaturated monocarboxylic acids, in particular those derived from acrylic and/or methacrylic acids.
• the preferred esters to be added to the hydrocarbon oil may be represented by the formula: wherein R is H or a methyl group, and R 1 is a C 8 to C 50 , preferably a C 10 to C 30' alkyl group.
• the esters may be prepared by any suitable technique such as by trans- esterification but are suitably prepared by direct esterification of the appropriate acid with the appropriate alcohol.
• Suitable alcohols include linear or branched and primary, secondary or tertiary alcohols. A single alcohol or a mixture of alcohols may be used.
• the alcohols may be natural or synthetic e.g. hydroformylation alcohols.
• the esters may be added to any liquid hydrocarbon oil.
• the liquid hydrocarbon oil may be a synthetic or natural oil with mineral oils being preferred.
• the esters may be added to crude mineral oil; lubricating oil; fuels e.g. heavy residual fuels and distillate fuels such as gasoline, aviation turbine fuel and gas oil; and functional oils e.g. hydraulic oils, heat transfer oils and automatic transmission fluids.
• the esters are particularly suitable for reducing the amount of insoluble material formed in lubricating oils and middle distillate fuels.
• the lubricating oils are preferably mineral oils which may be of a naphthenic,paraffinic or mixed naphthenic/paraffinic nature depending on the crude oil from which they are prepared. They may be obtained by vacuum distillation of oil and may have been subjected to one or more refining treatments, such as extraction, dewaxing or hydrogenation treatment.
• the present invention is useful for improving the resistance of hydrotreated lubricating oils, particularly hydrocracked lubricating oils, against the formation therein of insoluble material.
• hydrocracking is a severe hydrogenation treatment under conditions which depend upon the nature of the oil but usually comprises contacting the feedstock with hydrogen in the presence of a hydrogenation catalyst at a temperature usually between 350 and 500°C and at a pressure usually between 60 and 200 bars. Hydrocracking is usually performed in place of a conventional solvent extraction step. Hydrocracking usually increases the viscosity index of the feedstock and is used in the preparation of high, very high and extra high viscosity index lubricating oils. The hydrocracked lubricating oils may also be subjected to a hydrofinishing step which is a mild hydrogenation step.
• the middle distillate fuels which usually have a boiling point range in the range of from about 120 to 480°C at atmospheric pressure, may be straight run products or catalytically or thermally cracked products or hydrotreated products or mixtures thereof and they find utility as heating, diesel or jet fuels.
• the amount of ester present in the hydrocarbon oil compositions may vary between wide limitse.g. from 0.001 to 10%w, preferably from 0.01 to 2.0%w, based on the weight of the hydrocarbon oil.
• the hydrocarbon oil composition may contain other additives such as pour-point depressants, anti-corrosion agents, additives to improve the viscosity and viscosity- temperature characteristics, anti-oxidants, metal passiva- tors, extreme pressure and anti-wear additives.
• additives such as pour-point depressants, anti-corrosion agents, additives to improve the viscosity and viscosity- temperature characteristics, anti-oxidants, metal passiva- tors, extreme pressure and anti-wear additives.
• Example 1 a liquid hydrocracked hydrocarbon lubricating oil was used which was derived from a crude mineral oil.
• the lubricating oil has a VI of 94.5 and a viscosity (98.9°C) of 5.11 centistokes.
• Example 2 a C 20 /C 22 (1:4) alkyl acrylate
• Example 2 a C 20 /C 22 (1:4) alkyl methacrylate
• the oil composition (30 g) and the oil itself (30 g; Example a; comparative) were tested by blowing air through the mixture (15 litres/hour) for 168 hours after which the amount of insoluble material formed was determined.
• the results obtained were 0.36%w (Example 1), 0.33%w (Example 2) and 0.55%w (Example a).
• Example 3 a liquid middle distillate fuel was used having a boiling point range of from 150°C to 300°C.
• the fuel was subjected to the Jet Fuel Oxidation and Thermal Stability Test (ASTM 3241).
• the fuel caused filter blockage (pressure drop overfilter of more than 16,932 kPa) in 83 minutes.
• the test was then repeated after adding 0.02% (Example 3) and 0.03% (Example 4) of a C 20 /C 22 (1 : 4) alkyl acrylate.
• the composition of Example 3 caused filter blockage after 121 minutes and the composition of Example 4 had not caused filter blockage by the end of the test (150 minutes) at which time the pressure drop over filter was 1693.2 kPa.

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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)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Engineering & Computer Science (AREA)
• Lubricants (AREA)
• Liquid Carbonaceous Fuels (AREA)

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• 1978
  • 1978-05-22 GB GB21049/78A patent/GB1596126A/en not_active Expired
• 1979
  • 1979-04-09 CA CA325,149A patent/CA1126719A/en not_active Expired
  • 1979-05-10 EP EP79200228A patent/EP0005873B1/de not_active Expired
  • 1979-05-10 DE DE7979200228T patent/DE2963146D1/de not_active Expired
  • 1979-05-21 JP JP6160579A patent/JPS54153806A/ja active Granted

Patent Citations (5)

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