WO2006053664A1 - Additif pour ameliorer le pouvoir lubrifiant de carburants diesel - Google Patents

Additif pour ameliorer le pouvoir lubrifiant de carburants diesel Download PDF

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Publication number
WO2006053664A1
WO2006053664A1 PCT/EP2005/011998 EP2005011998W WO2006053664A1 WO 2006053664 A1 WO2006053664 A1 WO 2006053664A1 EP 2005011998 W EP2005011998 W EP 2005011998W WO 2006053664 A1 WO2006053664 A1 WO 2006053664A1
Authority
WO
WIPO (PCT)
Prior art keywords
esters
diesel
carboxylic acids
use according
acid
Prior art date
Application number
PCT/EP2005/011998
Other languages
German (de)
English (en)
Inventor
Markus Dierker
Herbert Fischer
Frank Bongardt
Harald Wallis
Original Assignee
Cognis Ip Management Gmbh
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 Cognis Ip Management Gmbh filed Critical Cognis Ip Management Gmbh
Publication of WO2006053664A1 publication Critical patent/WO2006053664A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters

Definitions

  • the present invention relates to the use of certain esters as lubricity improvers in hydrocarbon-based fuels, especially diesel fuels.
  • Hydrocarbon-based fuels in particular gasoline and diesel, usually contain a large number of additives in order to improve their usability.
  • Hydrocarbon-based fuels in particular gasoline and diesel, usually contain a large number of additives in order to improve their usability.
  • the SO ⁇ emission of fuel combustion can be significantly reduced.
  • No. 6,280,488 discloses additive mixtures which contain an ashless dispersant in combination with carboxylic esters, this additive increasing the lubricity of the oil.
  • a glycerol monooleate is tested as an additive to agents which, in addition to the glycerol monooleate, still contain the dispersants within the meaning of the technical teaching of US Pat. No. 6,280,488. It can be seen from Table 4 in column 12 of US Pat. No. 6,280,488 that the use of glycerol monooleate alone is not suitable for sufficiently improving the lubricity of diesel oil.
  • the present invention was therefore based on the object, an effective additive for improving the lubricity of fuels, especially low sulfur
  • a first subject of the present invention therefore relates to the use of esters prepared by reacting carboxylic acids of the general formula R-COOH in which R is a simple or polyunsaturated, branched or unbranched alkyl radical having 11 to 21 carbon atoms, or Mixtures of these carboxylic acids, with diglycerol, oligoglycerols and / or polyglycerols, as smokability improvers in hydrocarbon-based fuels.
  • Esters of carboxylic acids of the formula R-COOH with polyols are compounds known per se.
  • US Pat. No. 3,637,774 describes esters of polyglycerols and their preparation. Within the scope of the technical teaching claimed here, those esters are used to improve lubricity, the alcohol component of which is either a diglycerol or an oligoglycerol, that is to say a starting material formed by oligomerizing 2 to 5 moles of glycerol.
  • polyglycerols i. Condensation products of more than 5 moles of glycerol with each other.
  • Tables I, Ia and II in columns 3 and 4 of US Pat. No. 3,637,774 for the physical properties of the di-, oligo- and polyglycerides.
  • the polyols in the sense of the provisional present invention are reacted in a manner known per se in the presence of acidic and alkaline catalysts with the carboxylic acids of general formula R-COOH or derivatives thereof, for example the methyl ester thereof. It is essential for the present invention that the carboxylic acids used for the esterification are completely or predominantly monounsaturated or polyunsaturated. Particularly preferred is the esterification of the polyols with oleic acid. Since the use of pure oleic acid is cost-intensive, it is preferred for the purposes of the present technical teaching to use oleic acid mixtures of technical or natural origin which contain a particularly high proportion of oleic acid.
  • such acid mixtures would be used which contain more than 50 mol%, preferably more than 75 mol% and in particular more than 90 mol% of oleic acid. It is particularly preferred to resort to fatty acid mixtures obtained from rapeseed or rapeseed oil. Rapeseed oil or rapeseed oil is obtained from the seeds of rape or turnip rape. Rapeseed contains about 40-50% oil u. about 30% protein.
  • Old oilseed rape varieties contain high levels (35-64%) erucic acid, 5-10% Gondo acid [(Z) -11-eicosenoic acid, C 20 H 38 O 2, MR 310.52, Melting point: 24- 25 0 C ] and nervonic acid in addition to 13-38% oleic acid, 10-22% linoleic acid and 2-10% linolenic acid.
  • New rape varieties usually contain ⁇ 2% of the long-chain monoeno fatty acids.
  • LEAR low erucic acid rapeseed
  • the esters according to the present invention have an acid number according to DIN 53169 of at most 1.0, preferably less than 1.0 and in particular less than 0.6.
  • the additives may also contain less than 50% by weight, based on the total amount of ester used, of carboxylic acid esters with saturated carboxylic acids.
  • the glycerol esters of the present invention may be partially or fully esterified, i. it is possible that some or all of the free OH functions of the polyols have been reacted with carboxylic acids.
  • the esters are added to the fuel in amounts of from 10 to 1000 ppm, preferably from 50 to 200 ppm, and in particular in amounts of from 70 to 120 ppm, based on the amount of fuel.
  • fuels are understood as all energy-yielding fuels based on hydrocarbons whose free combustion energy is converted into mechanical work. These include all types of liquid at room temperature and normal pressure motor and aviation fuels.
  • Motor fuels e.g. for passenger car or truck engines, usually contain hydrocarbons, e.g. Benzine or higher boiling petroleum fractions or diesel fuel. Particularly preferred is the
  • Diesel fuels refer to flame-retardant mixtures of liquid hydrocarbons which are used as fuels for constant pressure or burner engines (diesel engines) and consist predominantly of paraffins with admixtures of olefins, naphthenes and aromatic hydrocarbons. Their composition varies and depends mainly on the method of preparation: common products have a density of 0.83-0.88, a boiling point in the range of 170-360 0 C and a flash point between 70-100 0 C. Diesel is obtained at the distillation of petroleum from gas oil, cracking, tars obtained from the carbonization (or hydrogenation) of brown or hard coal, and the hydrogenation of the coal extract.
  • Diesel for stationary equipment and marine engines have a similar composition as heavy fuel oil, which for cars, buses and trucks correspond to the fuel oil EL.
  • a key factor in the usability of diesel is its ignitability, for which the cetane number (CZ) was introduced in quantitative terms.
  • the ignition capability is the property of a motor fuel, lighter or harder to ignite in an operating on the diesel principle engine.
  • the requirements for diesel are CZ 20-40 for low-speed engines, CZ> 45 for small and high-speed engines.
  • One of the quality features of diesel is its low-temperature behavior, which can be described by the cloudpoint or preferably by the cold filter plugging point (CFPP), the temperature at which sucked-in diesel blocks a filter.
  • CFPP cold filter plugging point
  • Desirable are also a low pour point, low content of non-combustible and sooty substances and a niedri ⁇ ger sulfur content.
  • DIN-EN 590 05/1993
  • cetane number improvers nitric or nitric acid esters
  • corrosion inhibitors nitric or nitric acid esters
  • flow improvers nitric or nitric acid esters
  • surfactants keeping the injection nozzles clean
  • defoamers defoamers
  • smoke reducers as additives are added to the diesel.
  • Another object of the present invention relates to a process for improving the lubricity of fuels, in particular diesel oil, wherein the Dieselöl ⁇ ester or ester mixtures according to the above description in amounts of 10 to 1000 ppm added.
  • the process according to the invention is preferably carried out with fuels whose sulfur content is as low as possible, preferably less than 0.2% by weight of sulfur, based on the total amount of fuel. Examples

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

La présente invention concerne l'utilisation d'esters de diglycérine, d'oligoglycérine et/ou de polyglycérine avec des acides gras insaturés comme agents d'amélioration du pouvoir lubrifiant dans des carburants, en particulier dans des carburants diesel à faible teneur en soufre.
PCT/EP2005/011998 2004-11-18 2005-11-09 Additif pour ameliorer le pouvoir lubrifiant de carburants diesel WO2006053664A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004055589.3 2004-11-18
DE200410055589 DE102004055589A1 (de) 2004-11-18 2004-11-18 Additiv zur Schmierfähigkeitsverbesserung von Dieselölen

Publications (1)

Publication Number Publication Date
WO2006053664A1 true WO2006053664A1 (fr) 2006-05-26

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PCT/EP2005/011998 WO2006053664A1 (fr) 2004-11-18 2005-11-09 Additif pour ameliorer le pouvoir lubrifiant de carburants diesel

Country Status (2)

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DE (1) DE102004055589A1 (fr)
WO (1) WO2006053664A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012152309A1 (fr) * 2011-05-06 2012-11-15 Oleon Agent améliorant le pouvoir lubrifiant
US20160024411A1 (en) * 2012-02-17 2016-01-28 Total Marketing Services Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels
CN106590782A (zh) * 2016-12-05 2017-04-26 江苏汉光实业股份有限公司 柴油润滑性改进剂及其制备方法
WO2018162403A1 (fr) 2017-03-09 2018-09-13 Basf Se Utilisation de polyalcanolamines à modification hydrophobe en tant qu'inhibiteurs de cire, additif abaissant le point d'écoulement et additif pour lubrifiants

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19614722A1 (de) * 1996-04-15 1997-10-16 Henkel Kgaa Kältestabiles Schmier- und Kraftstoffadditiv
EP0826765A1 (fr) * 1996-08-27 1998-03-04 Institut Francais Du Petrole Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant
US5743922A (en) * 1992-07-22 1998-04-28 Nalco Fuel Tech Enhanced lubricity diesel fuel emulsions for reduction of nitrogen oxides
DE10252973A1 (de) * 2002-11-14 2004-05-27 Clariant Gmbh Oxidationsstabilisierte Schmieradditive für hochentschwefelte Brennstofföle

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5743922A (en) * 1992-07-22 1998-04-28 Nalco Fuel Tech Enhanced lubricity diesel fuel emulsions for reduction of nitrogen oxides
DE19614722A1 (de) * 1996-04-15 1997-10-16 Henkel Kgaa Kältestabiles Schmier- und Kraftstoffadditiv
EP0826765A1 (fr) * 1996-08-27 1998-03-04 Institut Francais Du Petrole Compositions d'additifs améliorant le pouvoir lubrifiant des carburants et carburants les contenant
DE10252973A1 (de) * 2002-11-14 2004-05-27 Clariant Gmbh Oxidationsstabilisierte Schmieradditive für hochentschwefelte Brennstofföle

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012152309A1 (fr) * 2011-05-06 2012-11-15 Oleon Agent améliorant le pouvoir lubrifiant
US9290434B2 (en) 2011-05-06 2016-03-22 Oleon Lubricity improver
US20160024411A1 (en) * 2012-02-17 2016-01-28 Total Marketing Services Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels
US9587193B2 (en) * 2012-02-17 2017-03-07 Total Marketing Services Additives for improving the resistance to wear and to lacquering of diesel or biodiesel fuels
CN106590782A (zh) * 2016-12-05 2017-04-26 江苏汉光实业股份有限公司 柴油润滑性改进剂及其制备方法
WO2018162403A1 (fr) 2017-03-09 2018-09-13 Basf Se Utilisation de polyalcanolamines à modification hydrophobe en tant qu'inhibiteurs de cire, additif abaissant le point d'écoulement et additif pour lubrifiants
US11274180B2 (en) 2017-03-09 2022-03-15 Basf Se Use of hydrophobically modified polyalkanolamines as wax inhibitors, pour point depressant and additive for lubricants

Also Published As

Publication number Publication date
DE102004055589A1 (de) 2006-05-24

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