EP2183340A1 - Biocarburant liquide issu d'esters et de glycérides liés, ainsi que son procédé de production - Google Patents

Biocarburant liquide issu d'esters et de glycérides liés, ainsi que son procédé de production

Info

Publication number
EP2183340A1
EP2183340A1 EP08801106A EP08801106A EP2183340A1 EP 2183340 A1 EP2183340 A1 EP 2183340A1 EP 08801106 A EP08801106 A EP 08801106A EP 08801106 A EP08801106 A EP 08801106A EP 2183340 A1 EP2183340 A1 EP 2183340A1
Authority
EP
European Patent Office
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.)
Withdrawn
Application number
EP08801106A
Other languages
German (de)
English (en)
Inventor
Peter Eisner
Michael Menner
Andreas STÄBLER
Andreas Malberg
Michael Frankl
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.)
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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 Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV filed Critical Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Publication of EP2183340A1 publication Critical patent/EP2183340A1/fr
Withdrawn legal-status Critical Current

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, 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
    • C10L1/02—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, 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
    • C10L1/02—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, 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
    • 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)
  • Emergency Medicine (AREA)
  • Biotechnology (AREA)
  • Microbiology (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

La présente invention a pour objet un biocarburant et un procédé de production, comprenant au moins une fraction de triglycérides, une fraction de monoglycérides, une fraction de diglycérides et une fraction d'alkylester d'acide gras. Ledit biocarburant s'obtient par transestérification partielle d'huile végétale ou de graisse végétale et est caractérisé en ce que le rapport massique à l'alkylester d'acide gras dans le biocarburant est inférieur au rapport massique aux triglycérides. Le carburant est particulièrement adapté en tant qu'additif pour les carburants classiques, s'obtient avec un rendement plus élevé, et s'utilise à des températures basses inférieures à 10 °C.
EP08801106A 2007-08-13 2008-07-31 Biocarburant liquide issu d'esters et de glycérides liés, ainsi que son procédé de production Withdrawn EP2183340A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007038232 2007-08-13
PCT/DE2008/001268 WO2009021486A1 (fr) 2007-08-13 2008-07-31 Biocarburant liquide issu d'esters et de glycérides liés, ainsi que son procédé de production

Publications (1)

Publication Number Publication Date
EP2183340A1 true EP2183340A1 (fr) 2010-05-12

Family

ID=40155933

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08801106A Withdrawn EP2183340A1 (fr) 2007-08-13 2008-07-31 Biocarburant liquide issu d'esters et de glycérides liés, ainsi que son procédé de production

Country Status (14)

Country Link
US (1) US20110289828A1 (fr)
EP (1) EP2183340A1 (fr)
JP (1) JP2010535908A (fr)
KR (1) KR20100051852A (fr)
CN (1) CN101821367A (fr)
AR (1) AR067881A1 (fr)
AU (1) AU2008286538B2 (fr)
BR (1) BRPI0815195A2 (fr)
CL (1) CL2008002379A1 (fr)
DE (1) DE112008002783A5 (fr)
MX (1) MX2010001710A (fr)
MY (1) MY156560A (fr)
RU (1) RU2010109418A (fr)
WO (1) WO2009021486A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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
JP7053454B2 (ja) * 2015-08-31 2022-04-12 フラウンホッファー－ゲゼルシャフト ツァ フェルダールング デァ アンゲヴァンテン フォアシュンク エー．ファオ グリセリド含有潤滑混合物
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

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000012743A1 (fr) * 1998-09-01 2000-03-09 Kansai Chemical Engineering Co., Ltd. Procede de production d'ester d'alcool inferieur
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
AU782699B2 (en) * 2000-12-15 2005-08-18 Sumitomo Chemical Company, Limited 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
FR2914927B1 (fr) * 2007-04-12 2009-06-12 Inst Francais Du Petrole Procede de fabrication d'esters alcooliques a partir de triglycerides et d'alcools au moyens de catalyseurs heterogenes a base de phosphate ou de compose organophosphore d'un metal du groupe 4.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009021486A1 *

Also Published As

Publication number Publication date
BRPI0815195A2 (pt) 2015-03-31
KR20100051852A (ko) 2010-05-18
AU2008286538A1 (en) 2009-02-19
AR067881A1 (es) 2009-10-28
RU2010109418A (ru) 2011-09-20
WO2009021486A1 (fr) 2009-02-19
DE112008002783A5 (de) 2010-07-15
AU2008286538B2 (en) 2012-09-13
MY156560A (en) 2016-02-26
CN101821367A (zh) 2010-09-01
CL2008002379A1 (es) 2008-12-19
JP2010535908A (ja) 2010-11-25
US20110289828A1 (en) 2011-12-01
MX2010001710A (es) 2010-03-11

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