EP3124579A1 - Composition de lubrifiant contenant des diesters ramifiés et agent améliorant l'indice de viscosité - Google Patents

Composition de lubrifiant contenant des diesters ramifiés et agent améliorant l'indice de viscosité Download PDF

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Publication number
EP3124579A1
EP3124579A1 EP15179371.8A EP15179371A EP3124579A1 EP 3124579 A1 EP3124579 A1 EP 3124579A1 EP 15179371 A EP15179371 A EP 15179371A EP 3124579 A1 EP3124579 A1 EP 3124579A1
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EP
European Patent Office
Prior art keywords
alkyl group
saturated
lubricant composition
linear
branched
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.)
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Application number
EP15179371.8A
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German (de)
English (en)
Inventor
Julien SANSON
Nicolas CHAMPAGNE
François BENARD
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.)
TotalEnergies Marketing Services SA
Original Assignee
Total Marketing Services SA
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 Total Marketing Services SA filed Critical Total Marketing Services SA
Priority to EP15179371.8A priority Critical patent/EP3124579A1/fr
Priority to PCT/EP2016/068229 priority patent/WO2017021332A1/fr
Priority to EP16745115.2A priority patent/EP3328971B1/fr
Priority to US15/748,635 priority patent/US20190002785A1/en
Priority to ES16745115T priority patent/ES2970805T3/es
Priority to CN201680048505.2A priority patent/CN108026463A/zh
Publication of EP3124579A1 publication Critical patent/EP3124579A1/fr
Withdrawn legal-status Critical Current

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    • 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
    • C10M129/72—Esters of polycarboxylic 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/34—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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
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    • 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
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    • 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
    • C10M129/78—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/02—Polyethene
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    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/04—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing propene
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    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/10—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing aromatic monomer, e.g. styrene
    • C—CHEMISTRY; METALLURGY
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—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
    • C10M145/12—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 monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
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    • 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
    • C10M2203/1025—Aliphatic fractions used as base material
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/022—Ethene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
    • 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
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/301—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 used as base material
    • 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
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    • 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
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
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    • 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
    • C10N2030/02—Pour-point; Viscosity index
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    • 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
    • C10N2030/04—Detergent property or dispersant property
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/54—Fuel economy
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10N2030/74—Noack Volatility
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • This application relates to lubricant compositions comprising branched diester compounds in association with a viscosity index improver.
  • the compositions can be used to reduce the fuel consumption and to improve the cleanliness of an engine, especially a car engine.
  • Lubricants are widely used to reduce friction between surfaces of moving parts and thereby reduce wear and prevent damage to such surfaces and parts.
  • Lubricants are composed primarily of a base stock and one or more lubricant additives.
  • the base stock may be a relatively high molecular weight hydrocarbon.
  • lubricating compositions composed only of hydrocarbon base stock tend to fail and the parts become damaged.
  • the lubricant manufacturer is in constant need to improve their formulations to address increased demands on fuel economy while balancing the need to improve the cleanliness of the engines or to reduce emissions. These demands force manufacturers to address their formulation capabilities and/or look for new base stocks that can meet the performance requirements.
  • lubricants such as motor oils, transmission fluids, gear oils, industrial lubricating oils, metal working oils, etc.
  • a lubricant grade of petroleum oil from a refinery, or a suitable polymerized petrochemical fluid.
  • additive chemicals are blended therein to improve material properties and performance, such as enhancing lubricity, inhibiting wear and corrosion of metals, and retarding damage to the fluid from heat and oxidation.
  • various additives such as oxidation and corrosion inhibitors, dispersing agents, high pressure additives, anti-foaming agents, metal deactivators and other additives suitable for use in lubricant formulations, can be added in conventional effective quantities.
  • the invention provides a lubricant composition comprising at least one compound of formula (I) below and at least one viscosity index improver wherein :
  • R1 represents a saturated linear C5-C15 alkyl group, more preferably a saturated linear C5-C12 alkyl group
  • R' represents a saturated linear C3-C8 alkyl group, more preferably a saturated linear C5-C8 alkyl group
  • R represents a saturated linear or branched C5-C15 alkyl group, more preferably a saturated linear or branched C5-C10 alkyl group.
  • the compound of formula (I) is a compound of formula (Ia)
  • the compound of formula (I) is a compound of formula (Ib)
  • the viscosity index improver is a polymeric viscosity index improver, preferably chosen among :
  • the lubricant composition comprises from 0,1 to 50%, preferably from 1 to 50%, more preferably from 5 to 30% by weight based on the total weight of lubricant composition, of a compound of formula (I).
  • the lubricant composition comprises from 0,01 to 15%, preferably from 1 to 10% by weight based on the total weight of lubricant composition, of at least one viscosity index improver.
  • the lubricant composition further comprises at least one lubricant base oil.
  • lubricant base oil is a group III lubricant base oil.
  • the lubricant composition comprises from 50 to 99%, preferably from 50 to 80% by weight based on the total weight of lubricant composition, of a lubricant base oil.
  • the lubricant composition further comprises further at least one lubricant additive selected from the list consisting of detergent additives, anti-wear additives, friction modifiers additives, extreme pressure additives, antioxidant additives, dispersing agents, pour-point depressant additives, anti-foam agents, thickeners and mixtures of two or more thereof.
  • lubricant additives selected from the list consisting of detergent additives, anti-wear additives, friction modifiers additives, extreme pressure additives, antioxidant additives, dispersing agents, pour-point depressant additives, anti-foam agents, thickeners and mixtures of two or more thereof.
  • the invention also provides the use of the lubricant composition according to the invention to reduce the fuel consumption of an engine, preferably of a car engine and/or to improve the cleanliness of an engine, preferably of a car engine, more preferably of at least one piston of a car engine.
  • the present application relates to the compositions and methods for synthesis of diester compounds for use as a base stock for lubricant applications, or a base stock blend component for use in a finished lubricant composition, or for the particular applications of fuel economy and imparting cleanliness to the engines.
  • the present diesters also exhibit improved detergency, as determined based on the Micro Coking Test (MCT).
  • Fuel economy is measured as the gain in various driving cycles, especially NEDC (New European Driving Cycle), and compared to trimethylol propane ester (Nycobase 7300 (NB7300)) which is an ester known to provide fuel economy (see e.g. Dodos, G.S., et al., Renewable fuels and lubricants from Lunaria annual. Ind. Crops Prod. (2015), http://dx.doi.org/10.1016/j.indcrop.2015.05.046 and DOI:10.1080/10402004.2015.1025934 ).
  • Cleanliness is measured as a rating of piston merit, especially against PAO which is known to be effective in cleanliness.
  • the diesters in accordance with the present embodiments may constitute a lubricant base stock composition, or a base stock blend component for use in a finished lubricant composition, or they may be mixed with one or more additives for further optimization as a finished lubricant or for a particular application. Suitable applications which may be utilized include, but are not limited to, (two-cycle) engine oils, especially car engines.
  • the diesters in accordance with the present embodiments may also have alternative chemical uses and applications, as understood by a person skilled in the art. The content of the diesters of the present embodiments may be found neat.
  • finished lubricant compositions may include between about 1 to about 25% by weight of the diester, from about 50 to about 99% by weight of a lubricating base oil, and from about 1 to about 25% by weight of an additive, especially an additive package.
  • additives may include detergents, antiwear agents, antioxidants, metal deactivators, extreme pressure (EP) additives, dispersants, viscosity modifiers, pour point depressants, corrosion protectors, friction coefficient modifiers, colorants, antifoam agents, demulsifiers and the like.
  • EP extreme pressure
  • the diesters of the invention are preferably in combination with a viscosity improver.
  • Viscosity improvers are known in the art and a description thereof can be found in Chemistry and Technology of Lubricants - Editors: Mortier, Roy M., Fox, Malcolm F., Orszulik, Stefan, Ed 2010 , which is incorporated herein by reference.
  • the viscosity improver is typically:
  • the amount of viscosity improver can be varied and is generally from 0,01 to 15%, preferably from 1 to 10% by weight based on the total weight of lubricant composition.
  • Suitable base oils can be any of the conventionally used lubricating oils, such as a mineral oil, a synthetic oil, or a blend of mineral and synthetic oils, or in some cases, natural oils and natural oil derivatives, all individually or in combinations thereof.
  • Mineral lubricating oil base stocks used in preparing the lubricant compositions can be any conventionally refined base stocks derived from paraffinic, naphthenic and mixed base crudes.
  • the lubricating base oil may include polyolefin base stocks, of both polyalphaolefin (PAO) and polyinternal olefin (PIO) types. Oils of lubricating viscosity derived from coal or shale are also useful.
  • synthetic oils include hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers); poly(1-hexenes), poly(1-octenes), poly(1-decenes), and mixtures thereof; alkyl-benzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)-benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenyls); alkylated diphenyl ethers and alkylated diphenyl sulfides and the derivatives, analogs and homologs thereof.
  • hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes
  • Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, and etherification constitute another class of known synthetic lubricating oils that can be used. These are exemplified by the oils prepared through polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methyl-polyisopropylene glycol ether having a number average molecular weight of 1000, diphenyl ether of polyethylene glycol having a molecular weight of 500-1000, diethyl ether of polypropylene glycol having a molecular weight of 1000-1500) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C 3-8 fatty acid esters, the C 13 Oxo acid diester of tetraethylene glycol, or PAGs, such as PO/BO, e.g. disclosed in WO201270007 and WO201316
  • esters of dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, and alkenyl malonic acids
  • esters of dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, and alkenyl malonic acids
  • alcohols e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, di
  • esters include dibutyl adipate, di-(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
  • Esters useful as synthetic oils also include those made from C 5 to C 12 monocarboxylic acids and polyols such as neopentyl glycol, trimethylol propane, and pentaerythritol, or polyol ethers such as dipentaerythritol, and tripentaerythritol.
  • polyols such as neopentyl glycol, trimethylol propane, and pentaerythritol, or polyol ethers such as dipentaerythritol, and tripentaerythritol.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils include another useful class of synthetic lubricants (e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl)silicate, tetra-(4-methylhexyl)silicate, tetra-(p-tert-butylphenyl) silicate, hexyl-(4-methyl-2-pentoxy)disiloxane, poly(methyl)siloxanes, and poly-(methylphenyl)siloxanes).
  • synthetic lubricants e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl)silicate, tetra-(4-methylhexy
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, and the diethyl ester of decane phosphonic acid), and polymeric tetrahydrofurans.
  • liquid esters of phosphorus-containing acids e.g., tricresyl phosphate, trioctyl phosphate, and the diethyl ester of decane phosphonic acid
  • polymeric tetrahydrofurans e.g., tricresyl phosphate, trioctyl phosphate, and the diethyl ester of decane phosphonic acid
  • Unrefined, refined and re-refined oils can be used as the lubricating base oil in the lubricant composition.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from primary distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification acts to improve one or more properties.
  • re-refined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service.
  • Such re-refined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques directed to removal of spent additives and oil breakdown products.
  • Oils of lubricating viscosity can also be defined as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines.
  • the five base oil groups are as given in the table that follows.
  • Groups I, II, and III are mineral oil base stocks.
  • the oil of lubricating viscosity is a Group I, II, III, IV, or V oil or mixtures thereof.
  • Groupe III hydrocacked or hydroisomerized oils ⁇ 90% ⁇ 0.03 % ⁇ 120
  • Groupe IV Polyalphaolefins (PAO) Groupe V All other synthetics
  • the diesters were prepared via a two-act route of transesterification and saturated fatty acid addition. In other aspect, the diesters were prepared via a three-act route of transesterification, formic acid addition, and saturated fatty acid addition.
  • the reactant esters are commonly (fatty) acid alkyl esters, including C 1 -C 20 (fatty) acid alkyl esters derived from a natural oil.
  • the C 1 -C 20 (fatty) acid alkyl esters may be unsaturated alkyl esters, such as unsaturated fatty acid methyl esters.
  • esters may include 9-DAME (9-decenoic acid methyl esters), 9-UDAME (9-undecenoic acid methyl esters), and/or 9-DDAME (9-dodecenoic acid methyl esters).
  • the transesterification reaction is conducted at approximately 60-80°C and approximately 1 atm.
  • Such fatty acid alkyl esters are conveniently generated by self-metathesis and/or cross metathesis of a natural oil.
  • Metathesis is a catalytic reaction that involves the interchange of alkylidene units among compounds containing one or more double bonds (i.e., olefinic compounds) via the formation and cleavage of the carbon-carbon double bonds.
  • Self-metathesis may be represented schematically as shown in Equation II below.
  • Suitable olefins are internal or ⁇ -olefins having one or more carbon-carbon double bonds, and having between about 2 to about 30 carbon atoms. Mixtures of olefins can be used.
  • the olefin may be a monounsaturated C 2 -C 16 ⁇ -olefin, such as a monounsaturated C 2 -C 10 ⁇ -olefin.
  • the olefin may also include C 4 -C 9 internal olefins.
  • suitable olefins for use include, for example, ethylene, propylene, 1-butene, cis- and trans -2-butene, 1-pentene, isohexylene, 1-hexene, 3-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, and the like, and mixtures thereof, and in some examples, ⁇ -olefins, such as ethylene, propylene, 1-butene, 1-hexene, 1-octene, and the like.
  • ⁇ -olefins such as ethylene, propylene, 1-butene, 1-hexene, 1-octene, and the like.
  • Examples 8 and 9 of WO 2008/048522 may be employed to produce methyl 9-decenoate and methyl 9-dodecenoate. Suitable procedures also appear in U.S. Pat. Appl. Publ. No. 2011/0113679 , the teachings of which are incorporated herein by reference.
  • the metathesis catalyst in this reaction may include any catalyst or catalyst system that catalyzes a metathesis reaction. Any known metathesis catalyst may be used, alone or in combination with one or more additional catalysts. Some metathesis catalysts may be heterogeneous or homogenous catalysts. Non-limiting exemplary metathesis catalysts and process conditions are described in PCT/US2008/009635 , pp. 18-47, incorporated by reference herein. A number of the metathesis catalysts as shown are manufactured by Materia, Inc. (Pasadena, CA).
  • Cross-metathesis is accomplished by reacting the natural oil and the olefin in the presence of a homogeneous or heterogeneous metathesis catalyst.
  • the olefin is omitted when the natural oil is self-metathesized, but the same catalyst types may be used.
  • Suitable homogeneous metathesis catalysts include combinations of a transition metal halide or oxo-halide (e.g., WOCl 4 or WCl 6 ) with an alkylating cocatalyst (e.g., Me 4 Sn).
  • Homogeneous catalysts may include well-defined alkylidene (or carbene) complexes of transition metals, particularly Ru, Mo, or W.
  • Second-generation Grubbs catalysts may also have the formula described above, but L 1 is a carbene ligand where the carbene carbon is flanked by N, O, S, or P atoms, such as by two N atoms.
  • the carbene ligand may be part of a cyclic group. Examples of suitable second-generation Grubbs catalysts also appear in the '086 publication.
  • L 1 is a strongly coordinating neutral electron donor as in first- and second-generation Grubbs catalysts
  • L 2 and L 3 are weakly coordinating neutral electron donor ligands in the form of optionally substituted heterocyclic groups.
  • L 2 and L 3 are pyridine, pyrimidine, pyrrole, quinoline, thiophene, or the like.
  • a pair of substituents is used to form a bi- or tridentate ligand, such as a biphosphine, dialkoxide, or alkyldiketonate.
  • Grubbs-Hoveyda catalysts are a subset of this type of catalyst in which L 2 and R 2 are linked. A neutral oxygen or nitrogen may coordinate to the metal while also being bonded to a carbon that is ⁇ -, ⁇ -, or ⁇ - with respect to the carbene carbon to provide the bidentate ligand. Examples of suitable Grubbs-Hoveyda catalysts appear in the '086 publication.
  • Heterogeneous catalysts suitable for use in the self- or cross-metathesis reaction include certain rhenium and molybdenum compounds as described, e.g., by J.C. Mol in Green Chem. 4 (2002) 5 at pp. 11-12 .
  • Particular examples are catalyst systems that include Re 2 O 7 on alumina promoted by an alkylating cocatalyst such as a tetraalkyl tin lead, germanium, or silicon compound.
  • Others include MoCl 3 or MoCl 5 on silica activated by tetraalkyltins.
  • Suitable catalysts include ruthenium and osmium carbene catalysts as disclosed in U.S. Pat. Nos. 5,312,940 , 5,342,909 , 5,710,298, 5,728,785 , 5,728,917 , 5,750,815 , 5,831,108 , 5,922,863 , 6,306,988 , 6,414,097 , 6,696,597 , 6,794,534 , 7,102,047 , 7,378,528 , and U.S. Pat. Appl. Publ. No. 2009/0264672 A1 , and PCT/US2008/009635 , pp. 18-47, all of which are incorporated herein by reference.
  • a number of metathesis catalysts that may be advantageously employed in metathesis reactions are manufactured and sold by Materia, Inc. (Pasadena, Calif.).
  • Natural oils suitable for use as a feedstock to generate the fatty acid alkyl esters from self-metathesis or cross-metathesis with olefins are well known. Suitable natural oils include vegetable oils, algal oils, animal fats, tall oils, derivatives of the oils, and combinations thereof.
  • suitable natural oils include, for example, soybean oil, palm oil, rapeseed oil, coconut oil, palm kernel oil, sunflower oil, safflower oil, sesame oil, corn oil, olive oil, peanut oil, cottonseed oil, canola oil, castor oil, linseed oil, tung oil, jatropha oil, mustard oil, pennycress oil, camellina oil, coriander oil, almond oil, wheat germ oil, bone oil, tallow, lard, poultry fat, fish oil, and the like. Soybean oil, palm oil, rapeseed oil, and mixtures thereof are non-limiting examples of natural oils.
  • the fatty acid alkyl esters including the unsaturated fatty acid alkyl esters, are transesterified under conditions known to a person skilled in the art.
  • Such alcohols can be represented by R-OH, where R is the desired ester group, e.g., a shorter chain hydrocarbon, such as a C 1 -C 20 hydrocarbon, e.g. C 3 -C 15 hydrocarbon.
  • R is the desired ester group, e.g., a shorter chain hydrocarbon, such as a C 1 -C 20 hydrocarbon, e.g. C 3 -C 15 hydrocarbon.
  • Such hydrocarbon may include alkyl groups, aryl groups, alkenyl groups, alkynyl groups, which may be linear or branched.
  • the alcohols may include methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec.-butanol, tert.-butanol, pentanol, isoamyl, hexanol, cyclohexanol, heptanol, 2-ethyl hexanol, octanol. decanol, undecanol, dodecanol, eicosanol,
  • Suitable catalysts for the transesterification reaction include any acidic, non-volatile esterification catalysts, Lewis acids, Bronsted acids, organic acids, substantially non-volatile inorganic acids and their partial esters and heteropolyacids.
  • Particularly suitable esterification catalysts include alkyl, aryl or alkaryl sulfonic acids, such as for example methane sulfonic acid, naphthalene sulfonic acid, p-toluene sulfonic acid, and dodecyl benzene sulfonic acid.
  • Suitable acids may also include aluminum chloride, boron trifluoride, dichloroacetic acid, hydrochloric acid, iodic acid, phosphoric acid, nitric acid, acetic acid, stannic chloride, titanium tetraisopropoxide, dibutyltin oxide, and trichloroacetic acid.
  • These catalysts may be used in quantities of from about 0.1 to 5 percent by weight of the natural oil starting material.
  • the second act is a fatty acid addition that is performed across the double bond(s) of the unsaturated fatty acid alkyl ester.
  • the third act is a fatty acid addition is performed across the double bond(s) of the unsaturated fatty acid alkyl ester.
  • the fatty acid is a saturated fatty acid, and may be a straight chain or branched acid, and in some examples, a straight chain saturated fatty acid.
  • saturated fatty acids include propionic, butyric, valeric, caproic, enanthic, caprylic, pelargonic, capric, undecylic, lauric, tridecylic, myristic, pentadecanoic, palmitic, margaric, stearic, nonadecyclic, arachidic, heneicosylic, behenic, tricosylic, lignoceric, pentacoyslic, cerotic, heptacosylic, carboceric, montanic, nonacosylic, melissic, lacceroic, psyllic, geddic, ceroplastic acids.
  • the reaction of the saturated fatty acid and the unsaturated fatty acid alkyl ester is catalyzed by a strong acid.
  • the strong acid may be a Lewis Acid, a Bronsted acid, or a solid acid catalyst.
  • Examples of such acids include transition metal triflates and lanthanide triflates, hydrochloric acid, nitric acid, perchloric acid, tetrafluoroboric acids, or triflic acid.
  • Acids may include alkyl, aryl or alkaryl sulfonic acids, such as methane sulfonic acid, naphthalene sulfonic acid, trifluoromethane sulfonic acid, p-toluene sulfonic acid, and dodecyl benzene sulfonic acid.
  • alkyl, aryl or alkaryl sulfonic acids such as methane sulfonic acid, naphthalene sulfonic acid, trifluoromethane sulfonic acid, p-toluene sulfonic acid, and dodecyl benzene sulfonic acid.
  • Solid acid catalysts may include include cation exchange resins, such as Amberlyst® 15, Amberlyst® 35, Amberlite® 120, Dowex® Monosphere M-31, Dowex® Monosphere DR-2030, and acidic and acid- activated mesoporous materials and natural clays such a kaolinites, bentonites, attapulgites, montmorillonites, and zeolites. These catalysts may be used in quantities of from about 0.1 to 5 percent by weight of the natural oil starting material.
  • cation exchange resins such as Amberlyst® 15, Amberlyst® 35, Amberlite® 120, Dowex® Monosphere M-31, Dowex® Monosphere DR-2030, and acidic and acid- activated mesoporous materials and natural clays such a kaolinites, bentonites, attapulgites, montmorillonites, and zeolites. These catalysts may be used in quantities of from about 0.1 to 5 percent by weight of the natural oil starting material.
  • R and R1 may be one or more of the following: C 1 -C 20 alkyl, e.g. C 3 -C 20 alkyl, which may be linear or branched, saturated or unsaturated.
  • C 1 -C 20 alkyl e.g. C 3 -C 20 alkyl
  • Other non-limiting diesters are to be shown in the Examples below.
  • the diesters were prepared via a three-act route of transesterification, formic acid addition, and saturated fatty acid addition.
  • the transesterification conditions were similar to those described above.
  • the second act is the addition of formic acid across the double bond(s) of the unsaturated fatty acid alkyl ester.
  • Formic acid is distinct in the category of linear monocarboxylic acids in that it is approximately ten times more reactive that its higher carbon number analogues. Specifically, formic acid has a pKa value of 3.75, whereas acetic acid and propionic acid have pKa values of 4.75 and 4.87.
  • the significance of the relatively high acidity of formic acid was the addition of formic acid to the unsaturated fatty acid alkyl ester did not require the addition of strong acid catalysts. The omission of strong acid catalysts can lead to improved product quality, and the production of specific structural isomer products.
  • formic acid has other benefits, as in where free hydroxy species are the target compounds, the preparation of formyloxy esters is advantageous. For example, where acetic acid addition adducts are prepared, saponification of the acetyloxy ester would generate a stoichiometric amount of acetate salt waste. Conversely, the saponification of formyloxy esters would yield aqueous alkaline formate salts.
  • the hydroxyl group of the 9-hydroxy decanoic acid methyl ester is then esterified with a saturated fatty acid and an esterification catalyst.
  • saturated fatty acids include propionic, butyric, valeric, caproic, enanthic, caprylic, pelargonic, capric, undecylic, lauric, tridecylic, myristic, pentadecanoic, palmitic, margaric, stearic, nonadecyclic, arachidic, heneicosylic, behenic, tricosylic, lignoceric, pentacoyslic, cerotic, heptacosylic, carboceric, montanic, nonacosylic, melissic, lacceroic, psyllic, geddic, ceroplastic acids.
  • the esterification catalysts may be acidic, non-volatile catalysts, Lewis acids, Bronsted acids, organic acids, substantially non-volatile inorganic acids and their partial esters and heteropolyacids.
  • Particularly suitable esterification catalysts include alkyl, aryl or alkaryl sulfonic acids, such as for example methane sulfonic acid, naphthalene sulfonic acid, p-toluene sulfonic acid, and dodecyl benzene sulfonic acid.
  • Suitable acids may also include aluminum chloride, boron trifluoride, dichloroacetic acid, hydrochloric acid, iodic acid, phosphoric acid, nitric acid, acetic acid, stannic chloride, titanium tetraisopropoxide, dibutyltin oxide, and trichloroacetic acid.
  • R and R1 may be one or more of the following: C 1 -C 20 alkyl, e.g. C 3 -C 20 alkyl, which may be linear or branched, saturated or unsaturated.
  • synthesized diesters may include the following structure:
  • compositions indicate the origin of each component.
  • a shorthand nomenclature can be used to describe these compositions.
  • the composition can be labeled C12/9-DA-2EH, to reference the C12 fatty acid, 9-DAME, and 2-ethyl hexanol.
  • diesters are to be shown in the Examples below, which may include isomers thereof, including cis- and trans- isomers.
  • Acid Value is a measure of the total acid present in an oil. Acid value may be determined by any suitable titration method known to those of ordinary skill in the art. For example, acid values may be determined by the amount of KOH that is required to neutralize a given sample of oil, and thus may be expressed in terms of mg KOH/ g of oil.
  • NOACK Volatility is a measure of evaporative loss of a lubricating base oil over a period of time. The values reported were measured by ASTM Method ASTM D6375 - 09.
  • a 3-neck round bottom flask was fitted with a Dean-Stark trap under a condenser.
  • the reaction vessel was charged with 1.0 molar equivalent of the desired unsaturated fatty acid methyl ester (FAME, e.g. methyl-9-decenoate, methyl-9-dodecenoate), 1.2 molar equivalents of the desired alcohol (e.g. 2- ethylhexanol, 1-octanol, isobutanol), and 10 wt% octanol.
  • FAME unsaturated fatty acid methyl ester
  • 2- ethylhexanol 1-octanol, isobutanol
  • 10 wt% octanol e.g. 2- ethylhexanol, 1-octanol, isobutanol
  • 10 wt% octanol e.g. 2- ethylhex
  • the headspace was continuously purged with nitrogen, and the temperature of the reaction mixture was increased 5 °C every 30 minutes until GC-FID indicated that all FAME had been consumed (e.g., ⁇ 4 hour reaction time).
  • the catalyst was quenched with an equal equivalent of KOH in water (0.1 N concentration).
  • the mixture was then phase separated, and the organic phase was washed with water three times (20 g water / 100 g reaction mixture), dried with MgSO 4 , and filtered.
  • the unsaturated esters were purified by distillation; isolated yields may be in the range of 75-90% of the theoretical yield.
  • a pH strip was used to provide the pH is greater than ⁇ 6.5 before distillation (as decomposition may occur). Distillation occurred at ⁇ 2 Torr (head temperature may be >230°C, pot temp >245°C). Add a plug of dry basic alumina (0.5" - 1" of alumina) to a fritted funnel and filter with a very weak vacuum ( ⁇ 650 Torr). If acid value was > ⁇ 0.5 mg KOH/g, repeat filtration over the same plug of alumina. Before disposal of the alumina, stirring with 5% EtOAc in Hexanes to release residual diester occurred. This portion can be thoroughly evaporated and then combined with the bulk product.
  • KV Kinematic Viscosity
  • VI Viscosity Index
  • the diester is represented by the structure which also may be referred to herein as 2-ethylhexyl 9-(octanoyloxy)decanoate.
  • Octyl-9-decenoate >98%, 200 g, 0.708 mol
  • octanoic acid Aldrich, ⁇ 98%, 306 g, 2.12 mol
  • trifluoromethanesulfonic acid Sigma Aldrich 98%, 10 g, 0.067 mol
  • the mixture was stirred at 60 °C for 20 h.
  • a saturated solution of NaHCO3 250 mL was added to the reaction vessel and stirred for 30 minutes.
  • the mixture was transferred to a separatory funnel and phase separated.
  • the organic phase was washed with brine (200 mL x 3), dried over MgSO4, and distilled at 234°C, 2 torr.
  • the distillate was washed again with water and dried by rotary evaporation to yield 77 g of clear colorless oil.
  • Physical properties were reported as follows: KV at 100°C was 3.16 cSt, KV at 40°C was 11.3 cSt, VI 151, NOACK volatility 10 wt%.
  • the diester may be referred to herein as octyl-9-(octanoyloxy)decanoate. This is ester of formula I(a)
  • the mixture was gravity filtered, and the product was recovered by vacuum distillation at 224°C, 2 Torr; starting materials were recovered as light fractions and the bottoms were discarded.
  • the major fraction was gravity filtered to yield the product as a colorless oil (397 g, 0.87 mol).
  • Light fractions during distillation were combined to provide a 512 g mixture containing 2-ethylhexyl-9-decenoate (69 w% by GC-FID) and decanoic acid (26 w% by GC-FID).
  • the entire quantity was treated with trifluoromethanesulfonic acid (Aldrich, ⁇ 98%, 10 g) and stirred for 18 h at 60°C.
  • the resulting suspension was vacuum filtered through Whatman 6 filter paper.
  • the filtrate was concentrated in vacuo and the oil was washed with a 0.1 M aqueous solution of K 2 CO 3 until pH was 7, then washed with water.
  • the organic phase was dried over Na 2 SO 4 then purified by vacuum distillation at 218°C, 0.1 Torr to give 69 g of oil.
  • the distillate was passed through a bed of Al 2 O 3 to give a clear colorless oil.
  • KV at 100°C was 3.97 cSt
  • KV at 40°C was 15.62 cSt
  • VI 160.6 pour point -40°C
  • the synthesized diester may be referred to as 10-[(2-ethylhexyl)oxy]-10-oxodecan-2-yl dodecanoate. This is ester of formula I(b).
  • the organic phase was dried with Na 2 SO 4 , and purified by distillation. The major fraction was obtained as 292 g of oil at 215 °C, 0.1 Torr. The distillate was filtered through basic alumina. KV at 100°C was 3.35 cSt, KV at 40 °C was 12.24 cSt, VI 154, pour point ⁇ -18°C, NOACK volatility 12 wt%.
  • 2-ethylhexyl-9-dodecenoate ( ⁇ 98%, 416 g, 1.47 mol) and dodecanoic acid (Sigma Aldrich, ⁇ 98%, 357 g, 2.07 mol) were treated with trifluoromethanesulfonic acid (Sigma Aldrich, 98%, 20 g, 0.13 mol) and stirred at 60°C for 18 h.
  • the reaction was cooled to 25°C while stirring and the catalyst was quenched within the reaction vessel by dropwise addition of KOH solution (7.5 g KOH in 75 mL H2O). The mixture was transferred to a separatory funnel and phase separated.
  • 9-OH-2-Ethylhexyldecanoate 50 g, 0.17 mol
  • dodecanoic acid 40g
  • methanesulfonic acid 0.8 g
  • toluene 200 mL
  • the flask was then fitted with a thermocouple temperature regulator with heating mantle, Dean-Stark distillation trap with water condenser.
  • the top of the condenser was fitted with a rubber stopper with nitrogen needle inlet.
  • Each of the three components of the diester compositions (methyl ester, alcohol, and saturated fatty acid) impart predictable performance qualities on the final structure.
  • the properties of a diester may be tuned to fit within specific performance specifications by carefully selecting the combination of starting materials.
  • Methyl -9-decenoate (50 g, 0.27 mol) and formic acid (100 mL) were added to a 250 mL 2-necked round bottom flask at 23 °C under an atmosphere of air.
  • the flask was then fitted with a thermocouple temperature regulator with heating mantle and water condenser.
  • the top of the condenser was fitted with a rubber stopper with nitrogen needle inlet.
  • the temperature was increased to 105 °C. After approximately 15 hours, the heating source was removed and the reaction was allowed to cool to ambient temperature.
  • the reaction flask was fitted with a reflux condenser and heated to reflux for 24 hours. The reaction was allowed to cool, the layers were separated and the organic product was dried by vacuum stripping (5 Torr, 100 °C) for 1 hour to obtain the desired 9-OH-2-ethylhexyldecanoate as a slight brown oil, 275 g (91%).
  • the formulas prepared are grade 0W-20 formulas. They were carried out at iso-HTHS (2.6 mPa.s). HTHS is the value at High Temperature High Shear.
  • the compositions and characteristics of the formulas tested are given in the table below Composition Comp Ester I(a) Ester I(b) P6660 13.30 13.30 13.30 SV261 3.60 3.60 3.60 INFINEUM V385 0.20 0.20 0.20 YUBASE 4 82.90 72.90 72.90 ESTER I(a) 10.00 ESTER I(b) 10.00 Physicochemical characteristics Ex Comp Ester I(a) Ester I(b) KV at 40°C mm 2 /s 44.26 40.70 42.63 KV at 100°C mm 2 /s 8.311 7.828 8.179 VI No Unit 166 166 170 HTHS mPa.s 2.59 2.6 2.60 Density (15°C) kg/m 3 849.7 861.1 856.6 CCS (-35°C
  • compositions according to the invention (Ester I(a) and Ester I(b)) have an improved « cold » behaviour.
  • MCT Micro Coking Test
  • compositions are prepared.
  • Composition Comp. Ester I(a) Ester I(b) Additive package 10.9 10.9 10.9 SV261 6.5 6.5 6.5 MoDTC 0.1 0.1 0.1 YUBASE 4+ 62.5 62.5 62.5 YUBASE 6 10.0 10.0 10.0 PAO 4 10.0
  • Physicochemical characteristics Ex Comp I(a) I(b) KV at 40°C mm 2 /s 53.16 50.34 50.87 KV at 100°C mm 2 /s 9.93 9.74 9.76 VI No Unit 176 183 181 HTHS mPa.s 2.9 2.88 2.9
  • the test that is used to determine cleanliness is based on the piston merit.
  • Each lubricant composition (10 kg) was evaluated in a test of cleanliness diesel common rail (common rail) for automobile.
  • the engine is a 1.4L 4 cylinders engine. Its power is 80 kW.
  • the cycle time of the test is 96 hours, alternating idle and 4000rpm regime.
  • the temperature of the lubricating composition is 145°C and the temperature of the cooling water system is 100°C. No drain nor any extra to lubricating composition is made during the test.
  • Fuel EN590 is used.
  • the test is performed in two phases for a total of 106 hours and in a first rinsing step and lapping for 10 hours and then in a second step with the composition to be evaluated(4 kg), and finally according to an endurance step with a duration of 96 hours with the composition to be evaluated (4 kg).
  • a first rinsing step and lapping for 10 hours and then in a second step with the composition to be evaluated(4 kg), and finally according to an endurance step with a duration of 96 hours with the composition to be evaluated (4 kg).
  • an endurance step with a duration of 96 hours with the composition to be evaluated (4 kg).
  • esters I(a) and I(b) improve both this scoring value by 5 and 7 points, respectively.
  • compositions are prepared.
  • OLOA 249SX is an over-based sulphonate detergent from Oronite.
  • Composition Comp. Ester I(a) Ester I(b) Additive package 10.6 10.6 10.6 SV261 6.2 6.2 6.2 MoDTC 0.5 0.5 0.5 OLOA 249SX 0.7 0.7 0.7 YUBASE 4+ 72.0 72.97 72.7 NICOBASE 7300 10.0
  • ESTER I(b) 9.3 Physicochemical characteristics Ex Comp I(a) I(b) KV at 40°C mm 2 /s 41.25 42.04 43.28 KV at 100°C mm 2 /s 8.43 8.51 8.64 VI No Unit 187 185 183 HTHS mPa.s 2.62 2.59 2.63
  • the test is run on an engine of 2.0L displacement and maximum power 180kW, driven by an electric motor generator.
  • the various lubricant compositions are compared with a reference lubricating composition (SAE 0W-30).
  • SAE 0W-30 a reference lubricating composition
  • Each friction measurement is performed for about 12 hours and enables a detailed mapping of the friction torque induced by each lubricant composition.
  • the tests are performed in the following sequence:
  • the instructions implemented are:
  • Friction gain is evaluated for each lubricant composition according to the temperature and the engine speed measured and compared to friction for the lubricant reference composition.
  • NB7300 The choice of the reference (NB7300) is driven by the fact that NB7300 is known for providing elevated fuel economy.
  • the results indicate that the three formulas are at least equivalent, if not better, from a fuel economy standpoint with gains of 0.05% and 0.03%.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
EP15179371.8A 2015-07-31 2015-07-31 Composition de lubrifiant contenant des diesters ramifiés et agent améliorant l'indice de viscosité Withdrawn EP3124579A1 (fr)

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EP15179371.8A EP3124579A1 (fr) 2015-07-31 2015-07-31 Composition de lubrifiant contenant des diesters ramifiés et agent améliorant l'indice de viscosité
PCT/EP2016/068229 WO2017021332A1 (fr) 2015-07-31 2016-07-29 Composition lubrifiante comprenant des diesters ramifiés et un agent améliorant l'indice de viscosité
EP16745115.2A EP3328971B1 (fr) 2015-07-31 2016-07-29 Composition de lubrifiant contenant des diesters ramifiés et agent améliorant l'indice de viscosité
US15/748,635 US20190002785A1 (en) 2015-07-31 2016-07-29 Lubricant composition comprising branched diesters and viscosity index improver
ES16745115T ES2970805T3 (es) 2015-07-31 2016-07-29 Composición lubricante que comprende diésteres ramificados y un mejorador del índice de viscosidad
CN201680048505.2A CN108026463A (zh) 2015-07-31 2016-07-29 包含支链二酯和粘度指数改进剂的润滑剂组合物

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US11085006B2 (en) 2019-07-12 2021-08-10 Afton Chemical Corporation Lubricants for electric and hybrid vehicle applications
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CN108026463A (zh) 2018-05-11
EP3328971A1 (fr) 2018-06-06
ES2970805T3 (es) 2024-05-30
WO2017021332A1 (fr) 2017-02-09
US20190002785A1 (en) 2019-01-03

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