GB796505A - Improved synthetic lubricant - Google Patents

Improved synthetic lubricant

Info

Publication number
GB796505A
GB796505A GB19967/55A GB1996755A GB796505A GB 796505 A GB796505 A GB 796505A GB 19967/55 A GB19967/55 A GB 19967/55A GB 1996755 A GB1996755 A GB 1996755A GB 796505 A GB796505 A GB 796505A
Authority
GB
United Kingdom
Prior art keywords
atoms
oxygen
sulphur
carbon atoms
radical
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
GB19967/55A
Inventor
Michael Frederick Hoare
Benjamin Thomas Fowler
Hans Georg Krischai
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering 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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to GB19967/55A priority Critical patent/GB796505A/en
Priority to US596135A priority patent/US2956954A/en
Priority to FR1162995D priority patent/FR1162995A/en
Publication of GB796505A publication Critical patent/GB796505A/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
    • C10M2207/302—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
    • 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
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • 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
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • 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
    • 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
    • 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
    • C10M2209/112—Complex polyesters having dihydric 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
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy 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
    • 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

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

The invention comprises a blend of complex esters in which the dicarboxylic acid component used to prepare the complex ester blend is a mixture of aliphatic dicarboxylic acids and either aromatic dicarboxylic acids or the anhydrides of aromatic dicarboxylic acids. The esters for use as lubricants are of general formul : R1COOR2OOCR3COOR4 R1COOR2OOCR3COOR12OOCR11 R4OOCR3COOR2OOCR13COOR14 where R1 and R11 are the residues of monocarboxylic acids, R2 and R12 are the residues of diols, R3 and R13 are the residues of dicarboxylic acids, and R4 and R14 are the residues of monohydric alcohols. R1 may be a straight or branched chain saturated hydrocarbon radical of 1 to 22 carbon atoms, or a series of saturated hydrocarbon radicals interlinked by 1 to 5 oxygen atoms, there being at least two carbon atoms between each pair of oxygen atoms and at least one carbon atom between the carboxyl group and the nearest oxygen atom, there being 3 to 22 carbon and oxygen atoms in the radical, or it may be a saturated aliphatic hydrocarbon chain containing a single interlinked sulphur atom which is separated from the carboxyl group by at least one carbon atom, the total number of carbon and sulphur atoms in the radical being 3 to 22. R2 may be a straight or branched chain saturated aliphatic hydrocarbon group of 2 to 18 carbon atoms, or a series of such hydrocarbon radicals linked by oxygen and/or ether sulphur, provided that there are at least two carbon atoms between each carboxyl group and the nearest oxygen and sulphur groups, or between each oxygen and sulphur atom, and that the total number of atoms in the radical is from 5 to 80, not more than 2 being sulphur. R3 may be a straight or branch-chained saturated aliphatic hydrocarbon radical containing up to 26 carbon atoms, or a series of hydrocarbon radicals linked by oxygen and/or sulphur, provided that there are at least two carbon atoms between each pair of oxygen or sulphur atoms and that the total number of atoms in the radical is from 30, there not being more than 2 sulphur atoms. R4 may be a saturated, straight or branched chain aliphatic hydrocarbon radical of 1-20 carbon atoms, or a series of such radicals, interlinked by oxygen and/or sulphur atoms, the total number of atoms in the radical being from 4 to 20, there not being more than 5 oxygen, or oxygen and sulphur, atoms in the radical, and the number of sulphur atoms does not exceed 2. The molecular weight of the entire ester should be at least 300 and the viscosity at 210 DEG F. should not be greater than 150 seconds (Saybolt). The complex esters may be prepared either by the monohydric alcohol half ester method or by refluxing all the components together in the presence of an esterification catalyst and water entrainer. Suitable temperatures of reflux are 150-200 DEG C., using an esterification catalyst such as sulphuric acid, sodium bisulphate, or an aryl sulphonic acid and a water entrainer such as an aromatic hydrocarbon. Any residual reactants should be removed, e.g. by vacuum stripping. Preferred starting materials are aliphatic straight or branched chain primary alcohols, containing no oxygen or sulphur atoms and having from 6 to 10 carbon atoms per molecule, fatty acids containing 2-10 carbon atoms per molecule, straight or branched chain dibasic acids of the paraffinic group having 6-10 carbon atoms per molecule, and ethylene glycol or any of its paraffinic homologues having up to 18 carbon atoms. Numerous examples of these are given. Suitable compounds which may be used to introduce an aromatic residue into the molecule are phthalic acids, or anhydrides, phenylenediacetic acids and higher phenylene alkanoic acids. The proportion of such material should preferably be less than 20 per cent. An example is given of the preparation of a blend of a complex ester and a diester (viz. di-(2-ethylhexyl) sebacate) using tetraethylene glycol, sebacic acid, and 2-ethylhexanol, and of a similar ester blend when part of the sebacic acid is replaced by phthalic anhydride. Various addition agents may be incorporated in the esters, e.g. antioxidants, thickeners, viscosity index improvers, pour-depressants and dyes.
GB19967/55A 1955-07-11 1955-07-11 Improved synthetic lubricant Expired GB796505A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB19967/55A GB796505A (en) 1955-07-11 1955-07-11 Improved synthetic lubricant
US596135A US2956954A (en) 1955-07-11 1956-07-06 Synthetic ester lubricants
FR1162995D FR1162995A (en) 1955-07-11 1956-07-11 Synthetic lubricant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB19967/55A GB796505A (en) 1955-07-11 1955-07-11 Improved synthetic lubricant

Publications (1)

Publication Number Publication Date
GB796505A true GB796505A (en) 1958-06-11

Family

ID=10138096

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19967/55A Expired GB796505A (en) 1955-07-11 1955-07-11 Improved synthetic lubricant

Country Status (3)

Country Link
US (1) US2956954A (en)
FR (1) FR1162995A (en)
GB (1) GB796505A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281288A (en) * 1963-11-27 1966-10-25 Exxon Research Engineering Co Processes and media for quenching metals
US3637501A (en) * 1968-11-05 1972-01-25 Ethyl Corp Complex esters
US4172802A (en) * 1978-05-30 1979-10-30 Cincinnati Milacron Inc. Aqueous metal working fluid containing carboxylic acid group terminated diesters of polyoxyalkylene diols
JPS6176442A (en) * 1984-09-21 1986-04-18 Satoru Matsumoto Production of composite ester
JPH05155809A (en) * 1991-12-05 1993-06-22 Satoru Matsumoto Diester complex ester having ether ester end structure and polyester
CN104862060A (en) * 2014-05-23 2015-08-26 山东瀚霖生物技术有限公司 Long-chain dibasic acid ester high-viscosity lubricating oil composition
US11760766B2 (en) 2020-07-28 2023-09-19 Ut-Battelle, Llc Ionic liquids containing quaternary ammonium and phosphonium cations, and their use as environmentally friendly lubricant additives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2575196A (en) * 1948-10-01 1951-11-13 Standard Oil Dev Co Mixed estirs of polyhydric alcohols and dibasic acids
US2499984A (en) * 1948-12-16 1950-03-07 Rohm & Haas Oily complex esters
GB687347A (en) * 1949-03-18 1953-02-11 Standard Oil Dev Co Improved lubricant blend
BE505417A (en) * 1951-08-09
US2742494A (en) * 1952-09-26 1956-04-17 Hercules Powder Co Ltd Mixed esters of phthalic acids and process for production thereof

Also Published As

Publication number Publication date
US2956954A (en) 1960-10-18
FR1162995A (en) 1958-09-19

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