EP0005873B1 - A liquid hydrocarbon oil composition containing an ester of an unsaturated carboxylic acid - Google Patents

A liquid hydrocarbon oil composition containing an ester of an unsaturated carboxylic acid Download PDF

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Publication number
EP0005873B1
EP0005873B1 EP79200228A EP79200228A EP0005873B1 EP 0005873 B1 EP0005873 B1 EP 0005873B1 EP 79200228 A EP79200228 A EP 79200228A EP 79200228 A EP79200228 A EP 79200228A EP 0005873 B1 EP0005873 B1 EP 0005873B1
Authority
EP
European Patent Office
Prior art keywords
ester
carboxylic acid
oil composition
unsaturated carboxylic
composition containing
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
EP79200228A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0005873A1 (en
Inventor
Hans Berger
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of EP0005873A1 publication Critical patent/EP0005873A1/en
Application granted granted Critical
Publication of EP0005873B1 publication Critical patent/EP0005873B1/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
    • 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
    • C10L1/18—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 hydrocracked lubricating oil compositions having improved resistance against the formation therein of insoluble material.
  • esters reduce the amount of insoluble material formed in hydrocracked lubricating oils, which normally tend to form insoluble material during use especially at high temperatures e.g. at temperature of at least 100°C.
  • the invention is concerned with a hydrocracked lubricating oil composition
  • a hydrocracked lubricating oil composition comprising 0.001 to 10%w of an ester of an olefinically unsaturated carboxylic acid and a C 10 to C 30 alkyl alcohol, characterized in that the ester is an ester of acrylic and/or methacrylic acid.
  • the esters may be prepared by any suitable technique such as by transesterification 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.
  • 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 feed-stock 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 amount of ester may vary between wide limits from 0.001. to 10%w, preferably from 0.01 to 2.0%w, based on the weight of the hydrocarbon oil.
  • the lubricating 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 passivators, 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 passivators, 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 ⁇ 10 -6 m 2 /s (5.1 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).

Landscapes

  • 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)
EP79200228A 1978-05-22 1979-05-10 A liquid hydrocarbon oil composition containing an ester of an unsaturated carboxylic acid Expired EP0005873B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB21049/78A GB1596126A (en) 1978-05-22 1978-05-22 Hydrocarbon oil composition
GB2104978 1978-05-22

Publications (2)

Publication Number Publication Date
EP0005873A1 EP0005873A1 (en) 1979-12-12
EP0005873B1 true EP0005873B1 (en) 1982-06-23

Family

ID=10156338

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79200228A Expired EP0005873B1 (en) 1978-05-22 1979-05-10 A liquid hydrocarbon oil composition containing an ester of an unsaturated carboxylic acid

Country Status (5)

Country Link
EP (1) EP0005873B1 (enrdf_load_stackoverflow)
JP (1) JPS54153806A (enrdf_load_stackoverflow)
CA (1) CA1126719A (enrdf_load_stackoverflow)
DE (1) DE2963146D1 (enrdf_load_stackoverflow)
GB (1) GB1596126A (enrdf_load_stackoverflow)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3700363A1 (de) * 1987-01-08 1988-07-21 Basf Ag Kraft- oder schmierstoffzusammensetzung und verwendung von polybutyl- oder polyisobutylderivaten in denselben
JPS63318402A (ja) * 1987-06-19 1988-12-27 東京電力株式会社 作業用ロボツト
WO1996041851A1 (fr) * 1995-06-08 1996-12-27 Idemitsu Kosan Co., Ltd. Additifs pour pressions extremes, modificateur du coefficient de friction et fluides fonctionnels
WO1999038939A1 (fr) * 1998-01-29 1999-08-05 Idemitsu Kosan Co., Ltd. Nouvelles compositions d'addition

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2204597A (en) * 1937-02-23 1940-06-18 Standard Oil Co Compounded lubricant
US2341565A (en) * 1940-01-22 1944-02-15 Standard Oil Co California Compounded oil
JPS5438124B2 (enrdf_load_stackoverflow) * 1972-04-19 1979-11-19
AR208270A1 (es) * 1972-05-08 1976-12-20 Texaco Development Corp Un poli(acrilato de n-alquilo)interpolimerico
GB1525804A (en) * 1976-03-17 1978-09-20 Shell Int Research Middle distillate fuel compositions

Also Published As

Publication number Publication date
JPS54153806A (en) 1979-12-04
CA1126719A (en) 1982-06-29
JPS6239196B2 (enrdf_load_stackoverflow) 1987-08-21
EP0005873A1 (en) 1979-12-12
GB1596126A (en) 1981-08-19
DE2963146D1 (en) 1982-08-12

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