EP1910503B1 - Utilisation d'une composition lubrifiante pour melange hydrocarbone et produits obtenus - Google Patents

Utilisation d'une composition lubrifiante pour melange hydrocarbone et produits obtenus Download PDF

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Publication number
EP1910503B1
EP1910503B1 EP06778762.2A EP06778762A EP1910503B1 EP 1910503 B1 EP1910503 B1 EP 1910503B1 EP 06778762 A EP06778762 A EP 06778762A EP 1910503 B1 EP1910503 B1 EP 1910503B1
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Prior art keywords
compound
mixture
group
use according
acid
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EP06778762.2A
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German (de)
English (en)
French (fr)
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EP1910503A1 (fr
Inventor
Nathalie Boitout
Laurent Dalix
Clarisse Doucet
Laurent Germanaud
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TotalEnergies Marketing Services SA
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Total Marketing Services SA
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    • C10M2207/285—Esters of aromatic 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy 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
    • C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether 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
    • 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
    • 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
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/065—Saturated Compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/067—Unsaturated Compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/069—Linear chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/071—Branched chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/43—Sulfur free or low sulfur content compositions
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • the present invention relates to the use of a hydrocarbon mixture composition especially with a low sulfur content, intended to improve their lubricity, but also concomitantly to limit their corrosive nature with respect to the metallic parts with which they are brought into contact with each other. increase their antistatic character by increasing their conductivity.
  • a composition is applicable to any hydrocarbon mixture, in whole or in part synthetic, capable of providing the energy required for the movement of land or flying vehicles, more particularly diesel fuel, kerosene or gasoline for internal combustion engines.
  • these hydrocarbons having a low sulfur content of less than 500 ppm, less than 50 ppm and even less than 10 ppm.
  • the additives containing dimer acids can not be used at high concentrations in fuels supplied to vehicles in which the fuel may be in contact with the lubricating oil, because these acids form, by chemical reaction, sometimes deposits. insoluble in the oil, but especially incompatible with the detergent additives, usually used.
  • esters or vegetable oils themselves are introduced into these fuels to improve their lubricity or lubricity.
  • esters derived from rapeseed, flax, soya, sunflower oils or the oils themselves see patents EP 635.558 and EP 605.857 ).
  • One of the major disadvantages of these esters is their low lubricating power at a concentration of less than 0.5% by weight in fuels.
  • the Applicant has proposed introducing into fuels with a low sulfur content, less than 500 ppm, the compositions obtained by mixing fatty monocarboxylic acids and polyaromatic monocarboxylic acids, preferably of plant origin, under acid form, ester or amine salts ( EP 915944 , EP.1310547 and EP 1340801 ).
  • WO 01/88064 claims a fuel composition
  • the demand WO 97/45507 proposes to introduce into the hydrocarbons, compounds derived from esterified alkenyl anhydrides, in proportions ranging from 5 to 5000 ppm. Applicants have found that by adding some of these compounds, the anti-corrosive properties of these fuels have been greatly improved.
  • the document US 4,448,586 discloses a liquid fuel having anti-corrosion properties comprising a major amount of monohydroxylated alkanol having 1 to 5 carbon atoms and a corrosion inhibiting amount of a mixture of an alkyl or alkenyl succinic acid or ester and of at least one polymerized unsaturated aliphatic monocarboxylic acid having from 16 to 18 carbon atoms.
  • the document US 4,032,303 discloses a fuel composition having a decreased tendency to deposit formation comprising a liquid fuel, a carboxylic acid ester and a liposoluble ester-type dispersant derived from a polyalcohol characterized by a hydrocarbon chain having at least 30 carbon atoms.
  • the document us 2004/0118033 discloses a fuel composition having improved antistatic properties and comprising a liquid fuel, a hydrocarbon monoamine or a poly (alkyleneamine) substituted with hydrocarbon compounds and at least one fatty acid comprising from 8 to 24 carbon atoms or one of its ester derivatives.
  • WO 02/02720 discloses a process for increasing the lubricity of a liquid hydrocarbon fuel having the addition of one or more component (s) derived from succinic anhydride.
  • the additive composition according to the invention will comprise from 40 to 70% by weight of at least a compound A and from 60 to 30% by weight of at least one compound B.
  • this efficiency can be improved if this composition further comprises at least 0.1% by weight of a compound C selected from C 5 -C 30 mono and / or polycarboxylic acid esters.
  • a compound C selected from C 5 -C 30 mono and / or polycarboxylic acid esters.
  • the addition of such esters to the concentrations of the invention makes it possible to improve the viscosity of the additive mixture which can thus be better dispersed in the hydrocarbon mixture.
  • composition will be all the more effective in terms of antistatic and lubricating efficacy that it will comprise from 30 to 60% by weight of at least one compound A, from 60 to 30% by weight of at least one compound B and from 5 to 20% by weight of at least one compound C.
  • R 1 is an alkenyl group of 1 to 22 carbon atoms
  • R 2 is hydrogen or vice versa.
  • radicals R 3 and R 4 of the compound A of formula (I) may also vary.
  • R 3 and R 4 are OR s with R 5 a group chosen from - [(CH 2 ) n -O] m -H with n varying from 1 to 4 and m varying. from 1 to 5; - [CH 2 -CHOH] p -CH 2 -OH, with p varying from 1 to 3; -CH 2 -CR 6 R 7 -OH, with R 6 and R 7 which can each be hydrogen, a methyl radical or a radical -CH 2 OH.
  • R 3 is OR 5 with R 5 a linear or branched alkyl group of C 1 to C 10 , optionally substituted by at least one OH group, and R 4 is OH or vice versa.
  • R 3 and R 4 are OR s groups, identical or different, with R 5 a linear or branched alkyl group of C 1 to C 10 , optionally substituted with at least one OH group.
  • R 3 is OH or OR s group with R 5 a linear or branched alkyl group of C 1 -C 10, optionally substituted with at least an OH group
  • R 4 is OR 5 with R 5 a - [(CH 2 ) n -O] m -H group with n varying from 1 to 4 and m varying from 1 to 5; - [CH 2 -CHOH] p -CH 2 -OH, with p varying from 1 to 3; -CH 2 -CR 6 R 7 -OH, with R 6 and R 7 which can each be hydrogen, a methyl radical or a radical -CH 2 OH.
  • the OR 5 groups are the groups -O-CH 2 -CH 2 -OH or -O-CH 2 -CHOH-CH 2 -OH or -O-CH 2 -C (CH 3 ) (CH 2 OH) -CH 2 -OH or -O-CH 2 -C (CH 2 OH) (CH 2 OH) -CH 2 -OH.
  • the compound B required for the invention will preferably be chosen as comprising at least one linear saturated or unsaturated carboxylic acid and / or their ester, amide or amine salt derivatives.
  • these acids oleic, linoleic, linolenic, palmitic, stearic and isostearic acids and their ester, amide and amine salt derivatives, alone or as a mixture, are preferred.
  • compound B will comprise mainly a mixture of oleic acid and linoleic acid, and / or their derivatives esters, amides or amine salts.
  • compound B will comprise a mixture of linear fatty acids of plant origin, rapeseed, castor oil, sunflower, corn, copra, pine or linseed, and / or their ester, amide or salt derivatives.
  • amines these products being generally commercial products.
  • Compound B will preferably consist of a mixture of linear fatty acids derived from the distillation of pine oils and / or their derivatives esters, amides or amine salts, whatever their origins.
  • compound B could comprise resin acids, among abietic acid, dihydroabietic acid, tetrahydroabietic acid, dehydroabietic acid, neoabietic acid, pimaric acid, levopimaric acid and parastinal acid, and / or their ester, amide or amine salts.
  • the compound B consists of a mixture of fatty acids and resin acids corresponding to a heavier distillate of the vegetable oil distillation. Distillates obtained by distillation of pine oil and / or their ester, amide or amine salt derivatives are preferred.
  • Compound C when added to the composition, is a vegetable oil ester of the group consisting of rapeseed, castor, sunflower, maize, coconut, pine or flax oils, the ester rapeseed methyl is preferred.
  • a second subject of the invention is a hydrocarbon mixture with a low sulfur content of less than 50 ppm, consisting mainly of hydrocarbons derived from the distillation of crude oil, a gasoline, a diesel fuel or a kerosene which can be used as fuel for the displacement of fuel. land or flying vehicles, this mixture comprising at least 50 ppm of the composition defined above.
  • the composition is particularly effective for hydrocarbon mixtures with a sulfur content of less than 10 ppm.
  • a hydrocarbon mixture according to the invention will advantageously comprise between 50 and 350 ppm of said composition.
  • the present example describes the preparation of various compounds A according to the invention.
  • the reaction consists of a mono- or di-esterification of the anhydride function with a polyol or mono alcohol without catalyst according to the reagents used.
  • an alkylated diacid compound in acid or anhydride form can be reacted with an alcohol or polyol in a tetracol reactor equipped with an ascending condenser, a thermometer, a dropping funnel and a nitrogen inlet. .
  • the alcohol or the polyol is dripped onto the previously heated acid or anhydride and maintained at 70.degree.
  • the sample is brought to the reflux temperature of the alcohol.
  • the reactor is maintained at this temperature and under nitrogen flushing for a period of about five hours.
  • the compound A thus obtained is distilled under vacuum in order to remove the water produced and / or the excess alcohol.
  • the present example aims to describe the lubricity performance of the compounds A i in admixture with a compound B i according to the invention, then in admixture with a third compound C i .
  • B 1 is a mixture of long chain fatty acids containing 2% of a mixture of resin acids derived from pine oil commonly called Tall oil fatty acid.
  • the lubricity of the Ai / Bi mixtures was tested in two different gasols, GO 1 and GO 2 according to the ISO 12156-1 standard for each concentration in the gas oil of 100, 150 and 200 ppm.
  • A1 is solid at room temperature, it is placed in an oven at 60 ° C. before formulation. For proportions greater than 50% of A 1 , it is necessary to place the mixture for a few minutes in an oven at 60 ° C in order to homogenize it.
  • the maximum level of A 1 in B 1 is limited by the state of the mixture at room temperature. Indeed it seems that the maximum rate of A 1 acceptable to have a liquid binary mixture at room temperature is between 80% (pasty mixture) and 60% (liquid but viscous).
  • the present example is intended to illustrate the lubricity efficiency of the other compounds A i according to the invention, alone or in combination with Bi and C 1 .
  • B 2 is an ester resulting from the reaction of B 1 with glycerol in a 1: 1 ratio
  • B 3 is the reaction product of B 1 with diethanolamine in a 1: 1 ratio.
  • the purpose of this example is to illustrate the significant effect of the Ai / Bi mixture on conductivity and corrosion.
  • composition according to the invention are also clearly visible for kerosines.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Lubricants (AREA)
  • Solid Fuels And Fuel-Associated Substances (AREA)
EP06778762.2A 2005-07-05 2006-07-04 Utilisation d'une composition lubrifiante pour melange hydrocarbone et produits obtenus Not-in-force EP1910503B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0507128A FR2888248B1 (fr) 2005-07-05 2005-07-05 Composition lubrifiante pour melange hydrocarbone et produits obtenus
PCT/FR2006/001578 WO2007006901A1 (fr) 2005-07-05 2006-07-04 Composition lubrifiante pour melange hydrocarbone et produits obtenus

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EP1910503A1 EP1910503A1 (fr) 2008-04-16
EP1910503B1 true EP1910503B1 (fr) 2013-09-04

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US (1) US8097570B2 (ru)
EP (1) EP1910503B1 (ru)
JP (2) JP2009500465A (ru)
KR (1) KR101327965B1 (ru)
CN (1) CN101213276B (ru)
ES (1) ES2433133T3 (ru)
FR (1) FR2888248B1 (ru)
NO (1) NO20080289L (ru)
RU (1) RU2449005C2 (ru)
WO (1) WO2007006901A1 (ru)

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KR101327965B1 (ko) 2013-11-13
JP5727554B2 (ja) 2015-06-03
CN101213276A (zh) 2008-07-02
US8097570B2 (en) 2012-01-17
RU2008103497A (ru) 2009-08-10
JP2009500465A (ja) 2009-01-08
NO20080289L (no) 2008-02-04
FR2888248B1 (fr) 2010-02-12
ES2433133T3 (es) 2013-12-09
FR2888248A1 (fr) 2007-01-12
JP2013224450A (ja) 2013-10-31
CN101213276B (zh) 2015-06-03
EP1910503A1 (fr) 2008-04-16
WO2007006901A1 (fr) 2007-01-18
RU2449005C2 (ru) 2012-04-27
US20080184617A1 (en) 2008-08-07
KR20080026647A (ko) 2008-03-25

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