WO2009021486A1 - Flüssiger biokraftstoff aus estern und gebundenen glyceriden sowie verfahren zur herstellung desselben - Google Patents
Flüssiger biokraftstoff aus estern und gebundenen glyceriden sowie verfahren zur herstellung desselben Download PDFInfo
- Publication number
- WO2009021486A1 WO2009021486A1 PCT/DE2008/001268 DE2008001268W WO2009021486A1 WO 2009021486 A1 WO2009021486 A1 WO 2009021486A1 DE 2008001268 W DE2008001268 W DE 2008001268W WO 2009021486 A1 WO2009021486 A1 WO 2009021486A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- biofuel
- fraction
- triglycerides
- mass fraction
- mass
- 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.)
- Ceased
Links
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 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
- C10L1/19—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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
-
- 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
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
- C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
-
- 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
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/649—Biodiesel, i.e. fatty acid alkyl esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
- C10G2300/1014—Biomass of vegetal origin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Definitions
- the present invention relates to a liquid biofuel based on triglycerides, mono- and diglycerides and fatty acid alkyl esters and a process for the preparation thereof.
- the fuel is particularly useful as an additive to conventional fuels, e.g. Diesel, suitable. Direct use as fuel for internal combustion engines is also possible.
- Biofuels and biofuel mixtures based on vegetable oil or animal fat are described, for example, in DE 4116905 C1, WO 95/25152 A1, EP 855436 A2 or US Pat. No. 5,713,965.
- these publications disclose mixtures of rapeseed oils with gasoline or diesel to which an additional substance is added.
- this additional constituent is an alcohol, in WO 95/25152 Al an alkyl ester of a short-chain fatty acid having a chain length of at most 6 C atoms and in EP 855436 A2 an acetal.
- EP 1126011 A2 describes a process for the heterogeneously catalyzed transesterification of fats and oils under conditions in which at least one of the reactants is in the critical state.
- the glycerol formed here too is separated from the fatty acid alkyl esters and not used as a fuel fraction.
- the document US 5578090 A describes a biofuel consisting of fatty acid alkyl esters and bound glycerol.
- the bound glycerides are not in the form of mono-, di- and trialkylglycerol esters, but are present as mono-, di- and trialkylglycerol ethers. These ethers are prepared in a different from the transesterification reaction from the intermediates of the transesterification reaction.
- Plant oils are predominantly triglycerides, i. Esters of glycerine and three fatty acids, and too low levels of free fatty acids.
- PCT / DE2005 / 002156 describes a fuel produced by partial transesterification of triglycerides.
- the fuel yield is 100%, since the glycerol contained in fats and oils is not released, but is kept in the form of mono-, di- and triglycerides in solution.
- This mixture of bound glycerol and fatty acid alkyl esters is stable at room temperature.
- crystallization processes and the precipitation of individual components occur, in particular in the case of the compositions described as particularly advantageous in PCT / DE2005 / 002156.
- the fuel described in PCT / DE2005 / 002156 is therefore suitable only for use at room temperature or at higher temperatures. Especially for areas with low
- the object of the present invention is to provide a biofuel and a process for the production thereof which can be prepared with high yield and can also be used at lower temperatures.
- compositions of the biofuel and embodiments of the method for producing the same are the subject of the dependent claims or can be taken from the following description and the exemplary embodiments.
- the biofuel according to the invention contains at least one fraction of triglycerides, in particular vegetable oil or vegetable fat, and at least one fraction of monoglycerides and at least one fraction of diglycerides and additionally contains at least one fraction of fatty acid alkyl esters.
- Another factor to increase the solubility of glycerides in FSAE-containing fuels is the ratio of monoglycerides to diglycerides.
- a particularly advantageous mixture of mono-, di-, triglycerides with FSAE for cold storage contains the following composition:
- a mixture which contained 20-25% by mass of FSAE, 50-55% by weight,% of triglycerides, 20% by weight of diglycerides and 5% by weight of monoglycerides proved to be particularly cold-stable.
- a further improvement in cold stability can be achieved by adding up to 2% by weight of ethanol.
- the biofuel can be mixed in any ratio with fossil fuel, biodiesel or BTL fuel, thereby diluted and used as fuel for internal combustion engines. It is also possible to achieve a dilution of the fuel according to the invention in that diesel fuel or biodiesel is already added before the partial transesterification of the triglycerides.
- Vegetable oil are formed to fatty acid alkyl esters.
- mono-, di- and triglycerides which originate from another, possibly animal source or are of synthetic origin.
- mono- and diglycerides can be used in biofuel containing fatty acids with less than 10 carbon atoms.
- One possible method of production of the proposed biofuel is based on a partial transesterification of triglycerides. For this purpose, triglycerides are mixed with an alcohol and through
- the triglycerides used may be a raw material of vegetable, animal or synthetic origin as well as mixtures of triglycerides of various origin.
- the alcohol used is preferably a monohydric alcohol of any chain length. Both organic and inorganic compounds as well as enzymes and microorganisms can be used as the catalyst.
- the reaction can be carried out both by homogeneous and heterogeneous catalysis. In an economically particularly advantageous embodiment used as raw material source used cooking oils.
- residence time is meant the period of time during which the catalyst and the added alcohol are in contact with the triglycerides.
- Particularly advantageous is the use of carrier-bound sn-1,3 regiospecific lipases as a catalyst. It shows that a gradual addition of enzymes over several discontinuous production cycles leads to a particularly good yield. In each production cycle, the enzyme of the previous production cycle is used, with a small amount of unused enzyme being additionally added for a particularly good yield.
- the process temperature depends on the catalyst used and the triglyceride used, in particular its melting temperature.
- the residence time depends on the catalyst used, the amount of catalyst, the alcohol used and the triglyceride used.
- rapeseed oil In 100g of rapeseed oil, 2.0 g of ethanol are completely dissolved.
- the transesterification reaction is started by adding 1.0 g of an immobilized S n -I, 3 regiospecific lipase. The mixture is mixed for 3 hours at the temperature with the highest lipase activity.
- the lipase is separated from the reaction product to obtain a clear, single-phase liquid consisting of 30% by mass of fatty acid ethyl ester, 24% by mass of diglycerides,
- the separated enzyme can be reused in a second production cycle. This is carried out identically to that described above. At the start of the reaction, 0.1 g of fresh enzyme is added to the enzyme used in the first production cycle.
Landscapes
- 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)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Emergency Medicine (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Beans For Foods Or Fodder (AREA)
Abstract
Description
Claims
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE112008002783T DE112008002783A5 (de) | 2007-08-13 | 2008-07-31 | Flüssiger Biokraftstoff aus Estern und gebundenen Glyceriden sowie Verfahren zur Herstellung desselben |
| US12/673,091 US20110289828A1 (en) | 2007-08-13 | 2008-07-31 | Liquid biofuel made of esters and bound glycerides, and also process for production thereof |
| BRPI0815195 BRPI0815195A2 (pt) | 2007-08-13 | 2008-07-31 | Biocombustível, uso do biocombustível, e, processo para a preparação do biocombustível. |
| EP08801106A EP2183340A1 (de) | 2007-08-13 | 2008-07-31 | Flüssiger biokraftstoff aus estern und gebundenen glyceriden sowie verfahren zur herstellung desselben |
| CN200880103379A CN101821367A (zh) | 2007-08-13 | 2008-07-31 | 由酯和键结的甘油酯制成的液体生物燃料及其制造方法 |
| JP2010520417A JP2010535908A (ja) | 2007-08-13 | 2008-07-31 | エステルおよび結合グリセリドからつくられる液体バイオ燃料およびその製造方法 |
| AU2008286538A AU2008286538B2 (en) | 2007-08-13 | 2008-07-31 | Liquid biofuel made of esters and bound glycerides, and also process for production thereof |
| MX2010001710A MX2010001710A (es) | 2007-08-13 | 2008-07-31 | Biocombustible liquido a partir de esteres y de gliceridos fijados, asi como procedimiento para la fabricacion del mismo. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007038232 | 2007-08-13 | ||
| DE102007038232.6 | 2007-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2009021486A1 true WO2009021486A1 (de) | 2009-02-19 |
Family
ID=40155933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DE2008/001268 Ceased WO2009021486A1 (de) | 2007-08-13 | 2008-07-31 | Flüssiger biokraftstoff aus estern und gebundenen glyceriden sowie verfahren zur herstellung desselben |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20110289828A1 (de) |
| EP (1) | EP2183340A1 (de) |
| JP (1) | JP2010535908A (de) |
| KR (1) | KR20100051852A (de) |
| CN (1) | CN101821367A (de) |
| AR (1) | AR067881A1 (de) |
| AU (1) | AU2008286538B2 (de) |
| BR (1) | BRPI0815195A2 (de) |
| CL (1) | CL2008002379A1 (de) |
| DE (1) | DE112008002783A5 (de) |
| MX (1) | MX2010001710A (de) |
| MY (1) | MY156560A (de) |
| RU (1) | RU2010109418A (de) |
| WO (1) | WO2009021486A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017036785A1 (de) * | 2015-08-31 | 2017-03-09 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. | Schmierend wirkende mischung mit glyceriden |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8585901B1 (en) | 2013-01-25 | 2013-11-19 | Markus Johannes Lenger | Method of continuous in-situ triglyceride stabilization and sulfur reduction of FOG (fats, oil and grease) to optimize fuel extraction |
| IT201900014778A1 (it) * | 2019-08-14 | 2021-02-14 | Nextchem S P A | Processo per il pretrattamento di alimentazioni destinate alla produzione di bio-carburanti, mediante idrolisi di grassi ad alta temperatura e pressione |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020077492A1 (en) * | 2000-12-15 | 2002-06-20 | Fumisato Goto | Method for preparing fatty acid esters from seeds or fruits |
| DE102005002700A1 (de) * | 2005-01-19 | 2006-07-27 | Cognis Deutschland Gmbh & Co. Kg | Zusammensetzungen verwendbar als Biotreibstoff |
| WO2008135665A1 (fr) * | 2007-04-12 | 2008-11-13 | Ifp | Procede de fabrication d'esters alcooliques a partir de triglycerides et d'alcools au moyen de catalyseurs heterogenes a base de phosphate ou de compose organophosphore d'un metal du groupe 4 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5197999A (en) * | 1998-09-01 | 2000-03-21 | Kansai Chemical Engineering Co., Ltd. | Process for producing lower alcohol ester |
| JP2002241786A (ja) * | 2000-12-15 | 2002-08-28 | Sumitomo Chem Co Ltd | 植物の種子および/または果実から脂肪酸エステルを製造する方法 |
-
2008
- 2008-07-31 MX MX2010001710A patent/MX2010001710A/es unknown
- 2008-07-31 AU AU2008286538A patent/AU2008286538B2/en not_active Ceased
- 2008-07-31 KR KR1020107005225A patent/KR20100051852A/ko not_active Abandoned
- 2008-07-31 DE DE112008002783T patent/DE112008002783A5/de not_active Ceased
- 2008-07-31 MY MYPI2010000669A patent/MY156560A/en unknown
- 2008-07-31 US US12/673,091 patent/US20110289828A1/en not_active Abandoned
- 2008-07-31 CN CN200880103379A patent/CN101821367A/zh active Pending
- 2008-07-31 EP EP08801106A patent/EP2183340A1/de not_active Withdrawn
- 2008-07-31 BR BRPI0815195 patent/BRPI0815195A2/pt not_active IP Right Cessation
- 2008-07-31 WO PCT/DE2008/001268 patent/WO2009021486A1/de not_active Ceased
- 2008-07-31 JP JP2010520417A patent/JP2010535908A/ja active Pending
- 2008-07-31 RU RU2010109418/04A patent/RU2010109418A/ru unknown
- 2008-08-07 AR ARP080103462A patent/AR067881A1/es not_active Application Discontinuation
- 2008-08-13 CL CL2008002379A patent/CL2008002379A1/es unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020077492A1 (en) * | 2000-12-15 | 2002-06-20 | Fumisato Goto | Method for preparing fatty acid esters from seeds or fruits |
| DE102005002700A1 (de) * | 2005-01-19 | 2006-07-27 | Cognis Deutschland Gmbh & Co. Kg | Zusammensetzungen verwendbar als Biotreibstoff |
| WO2008135665A1 (fr) * | 2007-04-12 | 2008-11-13 | Ifp | Procede de fabrication d'esters alcooliques a partir de triglycerides et d'alcools au moyen de catalyseurs heterogenes a base de phosphate ou de compose organophosphore d'un metal du groupe 4 |
Non-Patent Citations (2)
| Title |
|---|
| DE FILIPPIS P ET AL: "Rapeseed Oil Transesterification Catalyzed by Sodium Phosphates", ENERGY & FUELS, THE SOCIETY, WASHINGTON, DC, US, vol. 19, no. 6, 1 January 2005 (2005-01-01), pages 2225 - 2228, XP003010535, ISSN: 0887-0624 * |
| MITTELBACH ET AL: "Lipase catalyzed alcoholysis of sunflower oil", OIL AND SOAP, AMERICAN OIL CHEMISTS'SOCIETY. CHAMPAIGN, US, 1 January 1900 (1900-01-01), XP002076829 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017036785A1 (de) * | 2015-08-31 | 2017-03-09 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. | Schmierend wirkende mischung mit glyceriden |
| AU2016315409B2 (en) * | 2015-08-31 | 2019-07-18 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. | Lubricating mixture having glycerides |
| US10640722B2 (en) | 2015-08-31 | 2020-05-05 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V. | Lubricating mixture having glycerides |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2183340A1 (de) | 2010-05-12 |
| MY156560A (en) | 2016-02-26 |
| RU2010109418A (ru) | 2011-09-20 |
| BRPI0815195A2 (pt) | 2015-03-31 |
| DE112008002783A5 (de) | 2010-07-15 |
| AU2008286538B2 (en) | 2012-09-13 |
| MX2010001710A (es) | 2010-03-11 |
| JP2010535908A (ja) | 2010-11-25 |
| CL2008002379A1 (es) | 2008-12-19 |
| AR067881A1 (es) | 2009-10-28 |
| AU2008286538A1 (en) | 2009-02-19 |
| US20110289828A1 (en) | 2011-12-01 |
| KR20100051852A (ko) | 2010-05-18 |
| CN101821367A (zh) | 2010-09-01 |
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