GB659103A - Complex esters - Google Patents

Complex esters

Info

Publication number
GB659103A
GB659103A GB31036/48A GB3103648A GB659103A GB 659103 A GB659103 A GB 659103A GB 31036/48 A GB31036/48 A GB 31036/48A GB 3103648 A GB3103648 A GB 3103648A GB 659103 A GB659103 A GB 659103A
Authority
GB
United Kingdom
Prior art keywords
atoms
atom
radicals
ether oxygen
aliphatic hydrocarbon
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
GB31036/48A
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
Priority to GB31036/48A priority Critical patent/GB659103A/en
Priority to FR991513D priority patent/FR991513A/en
Publication of GB659103A publication Critical patent/GB659103A/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
    • C10M2207/30—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
    • C10M2207/302—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 monocarboxylic acids, dicarboxylic acids and dihydroxy compounds 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
    • 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
    • C10M2209/111—Complex polyesters having dicarboxylic acid centres
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether group
    • 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

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 complex ester is prepared by esterifying a saturated aliphatic mono-carboxylic acid with an equimolar proportion of a glycol to form a half ester, and esterifying two molar proportions thereof with one of an aliphatic or aromatic dicarboxylic acid. Esters for use as lubricants may have the formula <FORM:0659103/IV (a)/1> where R1 and R11 are saturated C2-C20 aliphatic hydrocarbon radicals or a series of such C2 or higher radicals linked by one or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 5-80 and the number of S atoms not more than 2, R2 and R12 are C1-C22 saturated aliphatic hydrocarbon radicals or similar radicals wherein up to 5 of the C atoms are replaced by ether oxygen atoms, there being at least 1 C atom between the carboxyl group and the first O atom, and at least 2 C atoms between each pair of O atoms, or wherein 1 C atom has been replaced by a thioether sulphur atom; R3 is an aliphatic hydrocarbon radical containing up to 30 C atoms or a series of C2 or higher, such radicals linked by 1 or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 3-80 and the number of S atoms not more than 2, and there being at least 1 C atom between each carboxyl group and the nearest O or S or R3 is an aromatic nucleus containing not more than 2 and preferably 1 aromatic ring with or without aliphatic substituents up to a total of 16 C atoms; and the starting materials are so chosen that the molecular weight of the product is at least 300 and its viscosity at 210 DEG F. not more than 150 Saybolt seconds. Preferred glycols are polyethylene glycols HO(CH2CH2O)nCH2CH2OH, where n is 1-26. Preferred monocarboxylic acids are fatty acids of 2-10 C atoms; preferred dicarboxylic acids are straight-chain paraffinic acids of 6-10 C atoms. Numerous examples of these are given. The preparation and properties of esters from valeric, caproic, caprylic, acetic, propionic or butyric acid; ethylene glycol or tri-, tetra- or higher polyglycols or thiodiglycol; and adipic and/or sebacic, thiodipropionic or terephthalic acid are described. They may be blended with mineral oils, and antioxidants, and other additives incorporated.ALSO:A complex ester is prepared by esterifying a saturated aliphatic monocarboxylic acid with an equimolar proportion of a glycol to form a half ester, and esterifying two molar proportions thereof with one of an aliphatic or aromatic dicarboxylic acid. Esters for use as lubricants may have the formula R2.COO-R1-OOC-R3-COO.R11 -OOC.R12 where R1 and R11 are saturated C2-C20 aliphatic hydrocarbon radicals or a series of such C2 or higher radicals linked by one or more ether oxygen and/or thioether sulphur atoms, the total number of p C, O, and S atoms being 5-80 and the number of S atoms not more than 2; R2 and R12 are C1-C22 saturated aliphatic hydrocarbon radicals or similar radicals wherein up to 5 of the C atoms are replaced by ether oxygen atoms, there being at least 1 C atom between the carboxyl group and the first O atom, and at least 2 C atoms between each pair of O atoms, or wherein 1 C atom has been replaced by a thioether sulphur atom; R3 is an aliphatic hydrocarbon radical containing up to 30 C atoms or a series of C2 or higher such radicals linked by 1 or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 3-80 and the number of S atoms not more than 2, and there being at least 1 C atom between each carboxyl group and the nearest O or S, or R3 is an aromatic nucleus containing not more than 2 and preferably 1 aromatic ring with or without aliphatic substituents up to a total of 16 C atoms; and the starting materials are so chosen that the molecular weight of the product is at least 300 and its viscosity at 210 DEG F. not more than 150 Saybolt seconds. Preferred glycols are polyethylene glycols HO(CH2CH2 O)nCH2CH2OH where n is 1-26. Preferred monocarboxylic acids are fatty acids of 2-10 C atoms; preferred dicarboxylic acids are straight chain paraffinic acids of 6-10 C atoms. Numerous examples of these are given. The preparation and properties of esters from valeric, caproic, caprylic, acetic, propionic or butyric acid; ethylene glycol or tri-, tetra- or higher poly-glycols or thiodiglycol; and adipic and/or sebacic, thiodipropionic or terephthalic acid are described. Esterification is effected in toluene with p-toluene sulphonic acid monohydrate as catalyst. They may be blended with mineral oils, and antioxidants, and other additives incorporated.ALSO:A complex ester is prepared by esterifying a saturated aliphatic monocarboxylic acid with an equimolar proportion of a glycol to form a half ester, and esterifying two molar proportions thereof with one of an aliphatic or aromatic dicarboxylic acid. Esters for use as lubricants may have the formula R2COO-R1-OOC-R3 -COO.R11-OOC.R12 where R1 and R11 are saturated C2-C20 aliphatic hydrocarbon radicals or a series of such C2 or higher radicals linked by one or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 5-80 and the number of S atoms not more than 2; R2 and R12 are C1-C22 saturated aliphatic hydrocarbon radicals or similar radicals wherein up to 5 of the C atoms are replaced by ether oxygen atoms, there being at least 1 C atom between the carboxyl group and the first O atom, and at least 2 C atoms between each pair of O atoms, or wherein 1 C atom has been replaced by a thioether sulphur atom; R3 is an aliphatic hydrocarbon radical containing up to 30 C atoms or a series of C2 or higher such radicals linked by 1 or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 3-80 and the number of S atoms not more than 2, and there being at least 1 C atom between each carboxyl group and the nearest O or S, or R3 is an aromatic nucleus containing not more than 2 and preferably 1 aromatic ring with or without aliphatic substituents up to a total of 16 C atoms; and the starting materials are so chosen that the molecular weight of the product is at least 300 and its viscosity at 210 DEG F. not more than 150 Saybolt seconds. Preferred glycols are polyethylene glycols HO(CH2CH2O)nCH2CH2 OH where n is 1-26. Preferred monocarboxylic acids are fatty acids of 2-10 C atoms; preferred dicarboxylic acids are stright chain paraffinic acids of 6-10 C atoms. Numerous examples of these are given. The preparation and properties of esters from valeric, caproic, caprylic, acetic, propionic or butyric acid; ethylene glycol or tri-, tetra- or higher polyglycols or thiodiglycol; and adipic and/or sebacic, thiodipropionic or terephthalic acid are described. They may be blended with mineral oils, and antioxidants, and other additives incorporated.
GB31036/48A 1948-11-30 1948-11-30 Complex esters Expired GB659103A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB31036/48A GB659103A (en) 1948-11-30 1948-11-30 Complex esters
FR991513D FR991513A (en) 1948-11-30 1949-07-30 Advanced lubricant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31036/48A GB659103A (en) 1948-11-30 1948-11-30 Complex esters

Publications (1)

Publication Number Publication Date
GB659103A true GB659103A (en) 1951-10-17

Family

ID=10316975

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31036/48A Expired GB659103A (en) 1948-11-30 1948-11-30 Complex esters

Country Status (2)

Country Link
FR (1) FR991513A (en)
GB (1) GB659103A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1135445B (en) * 1953-07-02 1962-08-30 Exxon Research Engineering Co Process for the preparation of complex esters which can be used as lubricating oils or lubricating oil components
DE1225628B (en) * 1955-07-11 1966-09-29 Exxon Research Engineering Co Process for the production of mixed esters serving as lubricating oils
EP3255128A1 (en) * 2016-06-08 2017-12-13 Peter Greven GmbH & Co. KG Complex esters and their use

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1135445B (en) * 1953-07-02 1962-08-30 Exxon Research Engineering Co Process for the preparation of complex esters which can be used as lubricating oils or lubricating oil components
DE1225628B (en) * 1955-07-11 1966-09-29 Exxon Research Engineering Co Process for the production of mixed esters serving as lubricating oils
EP3255128A1 (en) * 2016-06-08 2017-12-13 Peter Greven GmbH & Co. KG Complex esters and their use

Also Published As

Publication number Publication date
FR991513A (en) 1951-10-08

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