EP0543356A2 - Procédé de fabrication des compositions avec un compostement amélioré à basse température - Google Patents

Procédé de fabrication des compositions avec un compostement amélioré à basse température Download PDF

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Publication number
EP0543356A2
EP0543356A2 EP92119657A EP92119657A EP0543356A2 EP 0543356 A2 EP0543356 A2 EP 0543356A2 EP 92119657 A EP92119657 A EP 92119657A EP 92119657 A EP92119657 A EP 92119657A EP 0543356 A2 EP0543356 A2 EP 0543356A2
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Prior art keywords
esters
long
fatty acid
chain fatty
process according
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EP92119657A
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German (de)
English (en)
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EP0543356A3 (en
EP0543356B1 (fr
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Uwe Böhmke
Horst Dr. Pennewiss
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Roehm GmbH Darmstadt
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Roehm GmbH Darmstadt
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    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
    • C10L10/16—Pour-point depressants
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/04—Fatty oil fractions
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    • 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
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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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    • 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
    • C10M145/16—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 polycarboxylic
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
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    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
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    • C10M2203/06—Well-defined aromatic compounds
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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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    • 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
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    • 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
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    • 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
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils used as base material
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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    • 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
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    • 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
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    • 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
    • C10M2209/086—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 polycarboxylic, e.g. maleic acid
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    • 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
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Definitions

  • the invention relates to a process for the preparation of compositions with improved low-temperature behavior for use as fuels or lubricants based on longer-chain fatty acid alkyl esters, in particular rape oil methyl esters.
  • PAMA polyalkyl (meth) acrylates
  • CFPP Gold Filter Plugging Point
  • PP Pour Point
  • the technology has partially switched to converting the naturally occurring triglycerides in fatty acid esters of monohydric alcohols, preferably into methyl esters, and using them in fuels (cf. DE-A 31 50 989, AT-B 387 399, M. Mittelbach et al. In Energy Agric 4 (3) 207-215 (1985), Chem. Abstr. 104 , 115 224j; Energy Agric. 2 , 369-84 (1983), Chem. Abstr. 100 , 106 496 q).
  • Experience is particularly available when used as an extender for diesel fuels or synthetic esters.
  • the task was therefore to provide additives for improving the low-temperature behavior, in particular the cold filter plugging point of fatty acid esters of monohydric alcohols, especially the rapeseed oil methyl ester.
  • the aim was to reduce the CFPP from -15 degrees C to -22 degrees C.
  • the additives should be in the range ⁇ 0.1% by weight.
  • the additives should also belong to a class other than that of the triglycerides.
  • the long-chain fatty acid esters FAE The long-chain fatty acid esters FAE
  • the expedient field of application of the method according to the invention results from the low-temperature behavior, especially the values of the CFPP of the long-chain fatty acid esters from natural sources. These were originally predominantly as triglycerides of mixtures of C10 (and lower) to approx. C26 fatty acids, namely saturated and unsaturated fatty acids. Depending on their composition or provenance, they are obtained as liquid vegetable oils, solid vegetable fats or as animal oils or animal fats. Overviews of the occurrences and compositions can be found in the literature (cf. Ullmann's Encyclopadie der Techn. Chemie, 4th edition, vol. 11 , pp. 458-459, Verlag Chemie; Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd.
  • esters of fatty acids derived from liquid vegetable oils with monohydric C1-C6 alcohols especially the methyl esters (usually in the proportions of the natural occurrence of the acids).
  • they do not contain any noteworthy C10 fatty acid fractions, C12 fractions mostly only in traces and also relatively little C14 fractions, so that the main fractions are to be found in the area of saturated / unsaturated C16-C24 fatty acids with a focus on unsaturated ones C18-C20 fatty acids.
  • the long-chain fatty acid esters FA-E are formed at least 95% by weight from C12-C26 fatty acids.
  • the fatty acid alkyl esters to be used according to the invention are prepared from the naturally occurring esters, especially the triglycerides, by processes known per se.
  • the naturally occurring fatty acid esters, in particular the triglycerides, can be converted, for example, by transesterification.
  • the rape oil methyl ester is of particular interest in the context of the present invention.
  • the following explanations exemplified are therefore preferably concerned with this ester, but they can easily be transferred to other fatty acid esters of the type claimed.
  • the rape oil methyl esters are commercially available (source: e.g. from CASTROL, Austria; from HENKEL, Düsseldorf).
  • a commercially available rape oil methyl ester can e.g. have the following composition: approx. 65% by weight oleic acid ester, approx. 19% by weight linoleic acid ester, approx. 2% by weight stearic acid ester, approx. 4% by weight palmitine ester, approx. 4% by weight ⁇ C14- Ester, approx. 6% by weight ⁇ C20 ester.
  • Such an ester is hereinafter referred to as FEA-1.
  • pour point depressants are generally the polymers used in particular, in particular those which are produced by a large number of long-chain ones Alkyl residues in the molecule are characterized or have a polyalkylene structure (cf. Ullmanns Encyclopadie der Technischen Chemie, 4th edition, vol. 20, pp. 548/549 Verlag Chemie 19; HF Mark et al. In Encyclopedia of Polymer Science and Engineering loc.cit. pg. 26 - 27.)
  • the temperature usually continues to rise, for example to 140 ⁇ 10 degrees C. If necessary, suitable conditions for the postpolymerization can be established by adding heat and / or further addition of initiator.
  • the total polymerization time is generally less than 12 hours.
  • the amounts added when adding the rapeseed methyl ester are 10 to 0.0001% by weight, preferably 0.1 to 0.05% by weight.
  • the C12-C30 fatty acid methyl esters can also be separated off by fractional distillation. For economic reasons, however, the fractional Crystallization is preferred according to the procedure outlined above.
  • the residues (preferably by filtration) are composed of unsaturated and saturated C12-C26 fatty acid methyl esters. These residues can advantageously be reused elsewhere.
  • the PPD additives are preferably incorporated by mixing in, expediently with stirring into the beet oil methyl ester before separating off the fatty acid methyl ester according to c).
  • compositions produced according to the invention can, in addition to the components mentioned, also other polymers used in a relevant manner and low-molecular compounds such as alcohols, long-chain iso-alcohols, fatty acid esters (esters of long-chain iso-alcohols) and the like. contain.
  • the CFPP is determined according to DIN 51 428, the "pour point" in a HERZOG PP apparatus MC 850.
  • U stands for the inconsistency U: Mw Mn -1 (See Vieweg-Esser, Kunststoff-Handbuch, Volume IX, p. 24, Carl Hanser 1975).
  • the pore size of the filter is specified according to ISO 4793. Filters P40 or P100 are preferred as pore sizes.
  • the viscosity ⁇ is determined according to DIN 51 398 / ASTM D 2183.

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  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Lubricants (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP92119657A 1991-11-22 1992-11-19 Procédé de fabrication des compositions avec un compostement amélioré à basse température Expired - Lifetime EP0543356B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4138429A DE4138429A1 (de) 1991-11-22 1991-11-22 Verfahren zur herstellung von kompositionen mit verbessertem tieftemperaturverhalten
DE4138429 1991-11-22

Publications (3)

Publication Number Publication Date
EP0543356A2 true EP0543356A2 (fr) 1993-05-26
EP0543356A3 EP0543356A3 (en) 1993-10-20
EP0543356B1 EP0543356B1 (fr) 1997-02-12

Family

ID=6445352

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92119657A Expired - Lifetime EP0543356B1 (fr) 1991-11-22 1992-11-19 Procédé de fabrication des compositions avec un compostement amélioré à basse température

Country Status (5)

Country Link
EP (1) EP0543356B1 (fr)
AT (1) ATE148915T1 (fr)
DE (2) DE4138429A1 (fr)
DK (1) DK0543356T3 (fr)
ES (1) ES2098425T3 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389113A (en) * 1990-12-17 1995-02-14 Henkel Kommanditgesellschaft Auf Aktien Mixtures of fatty alkyl lower alkyl esters having improved low-temperature stability
WO1999027037A1 (fr) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additif pour biodiesels et biocarburants
CN1054155C (zh) * 1996-03-21 2000-07-05 中国石油化工总公司石油化工科学研究院 一种复合钡基润滑脂及其制备方法
US7041738B2 (en) 2002-07-09 2006-05-09 Clariant Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US7473284B2 (en) 2003-12-11 2009-01-06 Clariant Produkte (Deutschland) Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US7476264B2 (en) 2003-10-25 2009-01-13 Lariant Produkte (Deutshland) Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US7500996B2 (en) 2003-10-25 2009-03-10 Clariant International Ltd. Cold flow improvers for fuel oils of vegetable or animal origin
US7815697B2 (en) 2003-12-11 2010-10-19 Clariant Finance (Bvi) Limited Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006022698B4 (de) * 2006-05-16 2008-10-02 Clariant International Limited Zusammensetzung von Brennstoffölen
DE102006022718B4 (de) * 2006-05-16 2008-10-02 Clariant International Limited Zusammensetzung von Brennstoffölen
DE102006022719B4 (de) * 2006-05-16 2008-10-02 Clariant International Limited Kaltfließverbesserer für pflanzliche oder tierische Brennstofföle
DE102006022720B4 (de) * 2006-05-16 2008-10-02 Clariant International Limited Kaltfließverbesserer für pflanzliche oder tierische Brennstofföle
CN101205489B (zh) * 2006-12-18 2012-01-25 中国石油化工股份有限公司 一种燃料油添加剂组合物、其制备方法及其应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR846829A (fr) * 1938-06-02 1939-09-26 Raffinage Cie Francaise Procédé de préparation d'huiles de filage très actives et produits en résultant
FR976997A (fr) * 1942-06-02 1951-03-27 Raffinage Cie Francaise Amélioration de la combustion des huiles grasses
US2610915A (en) * 1950-07-24 1952-09-16 Swift & Co Winterized glyceride oil and process of producing the same
GB1354749A (en) * 1971-07-14 1974-06-05 Exxon Research Engineering Co Palm oil compositions
FR2492402A1 (fr) * 1980-10-21 1982-04-23 Inst Francais Du Petrole Compositions combustibles renfermant des esters d'acides gras, utilisables comme carburants diesel
AT387399B (de) * 1987-04-03 1989-01-10 Gaskoks Vertrieb Ges Mit Besch Verfahren und vorrichtung zur herstellung von fettsaeureestern und deren verwendung
DE4040317A1 (de) * 1990-12-17 1992-06-25 Henkel Kgaa Mischungen von fettsaeureniedrigalkylestern mit verbesserter kaeltestabilitaet

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389113A (en) * 1990-12-17 1995-02-14 Henkel Kommanditgesellschaft Auf Aktien Mixtures of fatty alkyl lower alkyl esters having improved low-temperature stability
CN1054155C (zh) * 1996-03-21 2000-07-05 中国石油化工总公司石油化工科学研究院 一种复合钡基润滑脂及其制备方法
WO1999027037A1 (fr) * 1997-11-21 1999-06-03 Rohmax Additives Gmbh Additif pour biodiesels et biocarburants
US6409778B1 (en) * 1997-11-21 2002-06-25 Rohmax Additives Gmbh Additive for biodiesel and biofuel oils
US7041738B2 (en) 2002-07-09 2006-05-09 Clariant Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US7476264B2 (en) 2003-10-25 2009-01-13 Lariant Produkte (Deutshland) Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US7500996B2 (en) 2003-10-25 2009-03-10 Clariant International Ltd. Cold flow improvers for fuel oils of vegetable or animal origin
US7473284B2 (en) 2003-12-11 2009-01-06 Clariant Produkte (Deutschland) Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US7815697B2 (en) 2003-12-11 2010-10-19 Clariant Finance (Bvi) Limited Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties

Also Published As

Publication number Publication date
ATE148915T1 (de) 1997-02-15
EP0543356A3 (en) 1993-10-20
DE4138429A1 (de) 1993-05-27
DE59208037D1 (de) 1997-03-27
ES2098425T3 (es) 1997-05-01
DK0543356T3 (da) 1997-08-18
EP0543356B1 (fr) 1997-02-12

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