GB844778A - Improvements relating to synthetic lubricants - Google Patents

Improvements relating to synthetic lubricants

Info

Publication number
GB844778A
GB844778A GB16626/57A GB1662657A GB844778A GB 844778 A GB844778 A GB 844778A GB 16626/57 A GB16626/57 A GB 16626/57A GB 1662657 A GB1662657 A GB 1662657A GB 844778 A GB844778 A GB 844778A
Authority
GB
United Kingdom
Prior art keywords
polyester
acid
carbon atoms
ethylhexanol
prepared
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
GB16626/57A
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.)
BP PLC
Original Assignee
BP PLC
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
Priority to BE567991D priority Critical patent/BE567991A/xx
Application filed by BP PLC filed Critical BP PLC
Priority to GB16626/57A priority patent/GB844778A/en
Priority to FR1206948D priority patent/FR1206948A/en
Priority to CH5987158A priority patent/CH377466A/en
Publication of GB844778A publication Critical patent/GB844778A/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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—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
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10N2040/12—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

A lubricating composition comprises a blend of a liquid aliphatic diester of a saturated aliphatic dicarboxylic acid, or a mixture of such diesters, and a polyester, soluble in the diester, and having the general formula ROOCR1COO (R2OOCR1COO)nR where n is an integer, the Rs are hydrocarbon residues of monohydric alcohols ROH, the R1s are hydrocarbon residues of dicarboxylic acids HOOCR1COOH and R2s are residues of diols HOR2OH, or a mixture of such polyesters, the polyester or polyester mixture having been prepared by reacting in one or more stages (a) an acid or acids of the formula HOOCR1COOH, or the anhydrides of such acids (where they exist), where R1 is an alkylene group having 4-14 carbon atoms, (b) a saturated monohydric alcohol or alcohols of the formula ROH where R is an alkyl group having 4-18 carbon atoms, (c) a diol or diols of the formula HOCH2C(R6)(R7)CH2OH where R6 is a methyl or ethyl group and R7 is an alkyl group having 1-4 carbon atoms, and (d)1,3-butanediol, the total molecular proportion of (c) and (d) being at least half the molecular proportion of (b), and the total molecular proportion of (b), (c) and (d) being greater than the molecular proportion of (a), the relative proportions of diester and polyester in the blend being such that the viscosity of the blend at 210,F. is 4-30 centistokes. The diesters may have the formula R4OOCR5COOR4 where R5 is an alkylene group having 4-14 carbon atoms and the R4s are alkyl groups, preferably branched-chain, having 4-18 carbon atoms. The lubricating composition may also contain an antioxidant, such as phenothiazine, or a crystallization suppressant, such as a polymerized alkyl ester of acrylic of methacrylic acid. In the examples, lubricating compositions are described consisting of a diester (a blend of octyl nonyl sebacate, dioctyl sebacate and dinonyl sebacate prepared from sebacic acid, 2-ethylhexanol and 3, 5, 5-trimethylhexanol), a polyester (prepared from sebacic acid, 2-ethyl hexanol, 2, 2-dimethyl-1, 3-propanediol and 1, 3-butanediol) and phenothiazine. For comparison purposes, a similar lubricating composition is described wherein the polyester is prepared from sebacic acid, 2-ethylhexanol and 1, 2-propanediol. Lubricating compositions are also described consisting of dioctyl or dinonyl sebacate and a polyester prepared from sebacic acid, 2-ethylhexanol and polyglycol 200. According to the Provisional Specification, the dicarboxylic acid HOOCR1COOH employed in the preparation of the polyester may be an aromatic acid such as phthalic acid and there is mentioned, for comparison purposes, a polyester derived from sebacic acid, phthalic anhydride, 2-ethylhexanol and propylene glycol.ALSO:A polyester, which is employed as an ingredient of a lubricating composition (see Group III) has the general formula ROOCR1COO (R2OOCR1COO)nR where n is an integer, the Rs are hydrocarbon residues of monohydric alcohols ROH, the R1s are hydrocarbon residues of dicarboxylic acids HOOCR1COOH and the R2s are residues of diols HOR2OH. The polyester, or a mixture of such polyesters, is prepared by reacting in one or more stages (a) an acid or acids of the formula HOOCR1-COOH, or the anhydrides of such acids (where they exist), where R1 is an alkylene group having 4-14 carbon atoms, (b) a saturated monohydric alcohol or alcohols of the formula ROH, where R is an alkyl group having 4-18 carbon atoms, (c) a diol or diols of the formula HOCH2C(R6)R7)CH2OH where R6 is a methyl or ethyl group and R7 is an alkyl group having 1-4 carbon atoms and (d) 1,3- butanediol, the total molecular proportion of (c) and (d) being at least half the molecular proportion of (b), and the total molecular proportion of (b), (c) and (d) being greater than the molecular proportion of (a). In an example, the polyester is prepared from sebacic acid, 2-ethylhexanol, 2,2-dimethyl-1,3-propanediol and 1,3-butanediol. For comparison purposes, the preparation of a polyester from sebacic acid, 2-ethylhexanol and 1,2-propanediol is described. According to the Provisional Specification, the dicarboxylic acid HOOCR1COOH employed in the preparation of the polyester may be an aromatic acid such as phthalic acid and there is mentioned, for comparison purposes, a polyester derived from sebacic acid, phthalic anhydride, 2-ethylhexanol and propylene glycol.ALSO:A lubricating composition, suitable for the lubrication of aero gas turbine engines, comprises a blend of a liquid aliphatic diester of a saturated aliphatic dicarboxylic acid, or a mixture of such diesters, and a polyester, soluble in the diester, and having the general formula ROOCR1COO(R2OOCR1COO)nR where n is an integer, the Rs are hydrocarbon residues of monohydric alcohols ROH, the R1s are hydrocarbon residues of dicarboxylic acids HOOCR1COOH and the R2s are residues of diols HOR2OH, or a mixture of such polyesters, the polyester or polyester mixture having been prepared by reacting in one or more stages (a) an acid or acids of the formula HOOCR1COOH, or the anhydrides of such acids (where they exist), where R1 is an alkylene group having 4-14 carbon atoms, (b) a saturated monohydric alcohol or alcohols of the formula ROH, where R is an alkyl group having 4-18 carbon atoms, (c) a diol or diols of the formula HOCH2C(R6)(R7)CH2OH where R6 is a methyl or ethyl group and R7 is an alkyl group having 1-4 carbon atoms, and (d) 1,3-butanediol, the total molecular proportion of (c) and (d) being at least half the molecular proportion of (b), and the total molecular proportion of (b), (c) and (d) being greater than the molecular proportion of (a), the relative proportions of diester and polyester in the blend being such that the viscosity of the blend at 210 DEG F. is 4-30 centistokes. The diesters may have the formula R4OOCR5COOR4 where R5 is an alkylene group having 4-14 carbon atoms and the R4s are alkyl groups, preferably branched-chain, having 4-18 carbon atoms. The lubricating composition may also contain an anti-oxidant, such as phenothiazine, or a crystallization suppressant, such as a polymerized alkyl ester of acrylic or methacrylic acid. In the examples, lubricating compositions are described consisting of a diester (a blend of octyl nonyl sebacate, dioctyl sebacate and dinonyl sebacate prepared from sebacic acid, 2-ethylhexanol and 3,5,5-trimethylhexanol), a polyester (prepared from sebacic acid, 2-ethylhexanol, 2,2-dimethyl-1,3-propanediol and 1,3-butanediol) and phenothiazine. For comparison purposes, a similar lubricating composition is described wherein the polyester is prepared from sebacic acid, 2-ethylhexanol and 1,2-propanediol. Lubricating compositions are also described consisting of dioctyl or dinonyl sebacate and a polyester prepared from sebacic acid, 2-ethylhexanol and polyglycol 200. According to the Provisional Specification, the dicarboxylic acid HOOCR1COOH employed in the preparation of the polyester may be an aromatic acid such as phthalic acid and there is mentioned, for comparison purposes, a polyester derived from sebacic acid, phthalic anhydride, 2-ethylhexanol and propylene glycol.
GB16626/57A 1957-05-24 1957-05-24 Improvements relating to synthetic lubricants Expired GB844778A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE567991D BE567991A (en) 1957-05-24
GB16626/57A GB844778A (en) 1957-05-24 1957-05-24 Improvements relating to synthetic lubricants
FR1206948D FR1206948A (en) 1957-05-24 1958-05-23 Synthetic lubricant for air and gas turbines
CH5987158A CH377466A (en) 1957-05-24 1958-05-23 Lubricants for gas turbines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB16626/57A GB844778A (en) 1957-05-24 1957-05-24 Improvements relating to synthetic lubricants

Publications (1)

Publication Number Publication Date
GB844778A true GB844778A (en) 1960-08-17

Family

ID=10080710

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16626/57A Expired GB844778A (en) 1957-05-24 1957-05-24 Improvements relating to synthetic lubricants

Country Status (4)

Country Link
BE (1) BE567991A (en)
CH (1) CH377466A (en)
FR (1) FR1206948A (en)
GB (1) GB844778A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2878652A4 (en) * 2012-07-26 2015-07-08 Jx Nippon Oil & Energy Corp Lubricant base oil, refrigerator oil and working fluid composition for refrigerators

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2878652A4 (en) * 2012-07-26 2015-07-08 Jx Nippon Oil & Energy Corp Lubricant base oil, refrigerator oil and working fluid composition for refrigerators
TWI595082B (en) * 2012-07-26 2017-08-11 Jx Nippon Oil & Energy Corp Lubricating base oil, refrigeration oil and freezer are used as the dynamic fluid composition
US9752091B2 (en) 2012-07-26 2017-09-05 Jx Nippon Oil & Energy Corporation Lubricant base oil, refrigerator oil and working fluid composition for refrigerators

Also Published As

Publication number Publication date
FR1206948A (en) 1960-02-12
CH377466A (en) 1964-05-15
BE567991A (en)

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