WO2012054946A1 - Procédé de production d'esters d'acides gras d'alcools inférieurs - Google Patents

Procédé de production d'esters d'acides gras d'alcools inférieurs Download PDF

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Publication number
WO2012054946A1
WO2012054946A1 PCT/AT2011/000437 AT2011000437W WO2012054946A1 WO 2012054946 A1 WO2012054946 A1 WO 2012054946A1 AT 2011000437 W AT2011000437 W AT 2011000437W WO 2012054946 A1 WO2012054946 A1 WO 2012054946A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
fatty acids
methanol
esterification
lower alcohols
Prior art date
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PCT/AT2011/000437
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German (de)
English (en)
Inventor
Theodor Wimmer
Original Assignee
Theodor Wimmer
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 Theodor Wimmer filed Critical Theodor Wimmer
Publication of WO2012054946A1 publication Critical patent/WO2012054946A1/fr

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Classifications

    • 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
    • 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
    • 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 invention relates to a process for the preparation of fatty acid esters of lower alcohols from fatty acids contained in fatty acid triglycerides or fatty acid esters of lower alcohols by esterification of the free fatty acids present with lower alcohols at atmospheric pressure and temperatures in the boiling range of the lower alcohols in the presence of acidic homogeneous Catalysts and optionally serving as a carrier material for the acidic catalysts, insoluble in the fatty acid triglycerides or fatty acid esters and optionally recovery and reuse of the catalysts by distilling off the excess of lower alcohol and water of reaction and subsequent alkaline catalyzed transesterification of the triglycerides with lower alcohols in one purity required for use as fuel for diesel engines.
  • Fatty acid triglycerides such as fats and oils of vegetable or animal origin or waste fats from the food preparation or fatty acid-containing fractions from edible oil refining or fatty acids or fatty acid-containing
  • Fatty acid methyl esters have recently acquired great economic and environmental importance as a substitute for fossil diesel fuels.
  • the raw materials used to produce biodiesel are obtained by pressing or extracting oilseeds such as e.g. Rapeseed, soybeans,
  • Sunflower seeds, jatrophan nuts, etc. and contain more or less free fatty acids depending on the method of production. Furthermore, waste greases such as e.g. used edible oils from the
  • 2007/012097 alkaline earth metal salts of fatty acids as catalysts at 210 ° C
  • EP 593524 free fatty acids as catalysts and 150 - 300 ° C. Disadvantages of these methods are the high reaction temperatures and pressures and the associated high expenditure on equipment and the high energy input.
  • Phosphoric acid hydrogen chloride
  • sulfonic acids such as p-toluene or
  • Camphersulfonic acid or metal salts are called, and in the
  • fatty acid-containing phase is pre-esterified together with the fatty acid-containing crude oil.
  • Sulfuric acid is named.
  • EP 127 104 and EP 184 740 describe the esterification of the free fatty acids contained in the crude oils in the presence of acidic catalysts such as alkyl, aryl, aryl-alkyl-sulfonic acids, e.g. Methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, naphthalenesulfonic acid, dodecylbenzenesulfonic acid,
  • acidic catalysts such as alkyl, aryl, aryl-alkyl-sulfonic acids, e.g. Methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, naphthalenesulfonic acid, dodecylbenzenesulfonic acid,
  • Molybdatophosphoric acid which is also present in an entraining agent, e.g. Glycerol, ethylene glycol, diethylene glycol and the like may be dissolved as a liquid carrier, wherein the catalyst acids are further used or regenerated after distilling off the excess methanol and the water of reaction.
  • DE 102 43700 likewise describes the use of a carrier material, in particular glycerol, for the sulfuric acid or p-toluenesulfonic acid used as catalyst, the acids being disposed of as fertilizer after neutralization with the alkaline catalyst for subsequent transesterification.
  • Sulfonic acids with respect to the reaction rate and the degree of esterification achieved and can be in contrast to hydrogen chloride and sulfuric acid by distilling off the excess methanol and the water of reaction in particular in the presence of an inert solvent regenerate and re-use as catalysts for esterification.
  • sulfuric acid monomethyl ester is also intermediately formed with methanol, and the possibility of forming small amounts of the highly toxic dimethyl sulfate can not be ruled out.
  • the object of the invention is therefore to provide a method which avoids the disadvantages of the aforementioned method and makes it possible, from inexpensive raw materials containing free fatty acids
  • Esterification catalysts are used.
  • the invention has surprisingly been found, for the first time, that no sulfur is introduced into the biodiesel when using 2-basic aliphatic or aromatic sulfonic acids for pre-esterification of free fatty acid-containing raw materials with subsequent alkaline-catalyzed transesterification.
  • the sulfur content is less than 5 mg / kg, preferably less than 2 mg / kg or corresponds to the sulfur content of the crude oil used.
  • methanol is used as the lower alcohol.
  • Suitable starting materials for the process according to the invention are triglycerides containing free fatty acids, e.g. Oils and fats of vegetable origin, such as e.g. by pressing or extracting in particular of
  • Degumming usually 1 to 2%, occasionally up to 15% and more free fatty acids included.
  • Suitable fatty acids containing triglycerides are waste fats from the food preparation which usually contain 3 to 6% of free fatty acids, in some cases more.
  • oil fractions that are used in the distillative deacidification of crude oils or from the "soapstock" of chemical deacidification
  • oil phases which are obtained by neutralization of the glycerol phase obtained as a by-product from methanol catalyzed by alkaline catalyzed transesterification with methanol and usually contain from 20 to 80% of free fatty acids besides fatty acid methyl esters are suitable for the process according to the invention.
  • the lower alcohol used is preferably methanol in an amount of 10 to 200% by weight, preferably 20 to 50% by weight, based on the weight of the oil used.
  • Suitable support materials for the acidic catalysts are those solvents which are insoluble in fatty acids, triglycerides and fatty acid esters of lower alcohols or mixtures thereof, e.g. aliphatic triols, glycols, di-, oligo-, or low molecular weight polyglycols, in particular diethylene glycol and glycerol.
  • the 2-basic sulfonic acids are used in an amount of 0, 1 to 6.0%
  • esterification reaction preferably takes place under stirring
  • Boiling temperature of the lower alcohol in particular of the methanol is usually completed after 1 to 4 hours, depending on the initial content of free fatty acids.
  • the esterification mixture then separates by gravity into a light phase consisting of methanol, the carrier material, the
  • the heavy phase is by repeated, preferably 3 times washing with methanol to completely remove the catalyst acid, the
  • Washing processes can be carried out by means of preferably three series-connected mixer / settler apparatus, wherein the after
  • Phase separation of the 1st washing stage resulting light methanol phase after receiving the regenerated catalyst is used for the next esterification approach and the light methanol phase from the 2nd washing stage for the 1st washing stage of the next esterification approach and the light methanol phase from the 3rd washing stage for the 2nd washing stage the next esterification approach is used and the 3rd washing step of the next
  • heavy phase washing may also be accomplished by liquid-liquid extraction, e.g. by means of a countercurrent column.
  • phase separations of the washing stages can also be effected by means of separators.
  • the washing operations can be carried out both batchwise and continuously. Regeneration of the catalyst:
  • the present after the phase separation of the esterification mixture light phase containing mainly methanol, the support material, the catalyst acid and the reaction water of the esterification is obtained by evaporation of Methanol and water released.
  • the evaporation of the methanol-water of reaction can be carried out for example via an evaporator at atmospheric pressure or at a slight negative pressure of 90 - 100mbar absolute and a temperature of not more than 80 - 90 ° C.
  • Reaction water as completely as possible to remove and in the interest of the lowest possible thermal load of the evaporation residue can be used after the evaporator, a falling film or thin film evaporator at pressures of preferably below 50 mbar absolute and temperatures of less than 50 ° C.
  • the evaporation residue is used without further purification
  • the methanol-water mixture obtained from the evaporators can be separated by means of a rectification column or dried by means of a molecular sieve and the anhydrous methanol thus obtained can in turn be used for esterification.
  • the heavy phase liberated by the washes of catalyst residues and water of reaction contains, depending on the initial free fatty acid content, fatty acid methyl esters, triglycerides, methanol and a residual fatty acid content of less than 1.0%, preferably less than 0.2%, and is readily available
  • the transesterification is carried out in a manner known per se, e.g. According to the teaching of EP 658183 carried out in 2 stages, due to the low
  • naphthalene-1, 5-disulfonic acid and 8.0 grams of diethylene glycol are dissolved in 45 grams of methanol and stirred intensively together with the rapeseed oil-oil phase mixture at 60-65 ° C for 75 minutes.
  • the mixture is then transferred to a separatory funnel and allowed to settle for 30 minutes at a temperature not lower than 50 ° C, wherein a phase separation in a light phase consisting of methanol, diethylene glycol, naphthalene -1, 5 - disulfonic acid and water of reaction and a heavy phase consisting from rapeseed oil and
  • the heavy phase is stirred to remove residual amounts of catalyst and water of reaction by means of three washing steps, each with 45 g of methanol and allowed to settle in a separatory funnel, with one each
  • Washing methanol from the 3rd washing stage is used for the 2nd washing stage of the further batch.
  • Rapeseed oil / rapeseed methyl ester mixture contains 300 ppm water, 0, 1% free fatty acids and 8% methanol. Regeneration of the catalyst:
  • the light phase obtained after settling of the esterification mixture is freed from methanol and water in a rotary evaporator until the
  • Residue has a water content of less than 3%, without further purification in 45 grams of washing methanol from the 1st Washed and used for a further Verest fürsanthesis.
  • Transesterification added, stirred for 3 minutes and transferred to a separatory funnel. After phase separation, the light phase is removed by washing with a dilute acid from adhering residual soaps and by distillation of excess methanol and water.
  • the yield is 150 g rapeseed methyl ester and corresponds in all values to EN 14214.
  • Fatty acid methyl ester which was obtained by an acid treatment of an originating from the alkaline transesterification glycerol processed.
  • the oil phase was mixed with refined rapeseed oil such that the oil phase / rapeseed oil mixture had an FFA content of 25%.
  • the catalyst used was naphthalene-1, 5-disulfonic acid dissolved in diethylene glycol.
  • the mixing ratio of the catalyst mixture was 20% by mass of naphthalene-1, 5-disulfonic acid and 80% by mass of diethylene glycol.
  • the oil phase / rapeseed oil mixture was placed in a receiver tank in which the medium was heated to 60 ° C. From this storage tank, the mixture was continuously fed into the process model by means of a pump at a rate of 429 g / h - for this endurance test consisting of the process units "Esterification with 3-stage wash", “Catalyst regeneration” and “Transesterification with biodiesel cleaning and drying” - pumped.
  • Catalyst regeneration and methanol from the separator of the 1st washing stage mixed in a mixer and then passed through a reactor.
  • the residence time of the mixture in the reactor was 160 minutes, the temperature in the reactor was kept at 60 ° C.
  • the corresponding esterification reactions took place, i. from the free fatty acids and the methanol were fatty acid methyl esters and water.
  • the mixture was at a residence time of 30 minutes at about 55 ° C in a light phase consisting mainly of methanol, diethylene glycol, naphthalene-1, 5-disulfonic acid, and water of reaction and in a heavy phase consisting mainly of rapeseed oil and
  • the heavy phase from the separator was in the following
  • the heavy phase from the 1st washing stage was mixed in a 2nd washing stage in a mixer with the light phase from the separator of the 3rd washing stage and washed again. In a subsequent separator that was
  • Rapeseed oil / fatty acid methyl ester mixture contained 330 ppm of water, 0.25% of free fatty acids and about 11% of methanol.
  • the light phase from the separator after the esterification reactor was transferred to a vessel in which the medium was maintained at a temperature of 55 ° C. From this container, the mixture consisting of mainly methanol, diethylene glycol, naphthalene-1, 5-disulfonic acid and water, a vacuum column, which at 80 to
  • the bottom product consisting mainly of diethylene glycol, naphthalene-1, 5-disulfonic acid and water, transferred with a pump in another vacuum column and dried to a residual water content in the bottom product below 30,000 ppm.
  • the bottom product was transferred by means of a pump into a buffer vessel from where the regenerated catalyst mixture was fed via a further pump to the mixer for the catalysis of the esterification.
  • the catalyst regeneration was also carried out continuously.
  • the rapeseed oil / fatty acid methyl ester mixture obtained from the esterification with the subsequent 3-stage wash was then from a
  • Buffer tank driven by a pump with a throughput of 487 g / h in a 2-stage transesterification stage followed by Biodieselgraphy and drying.
  • 63 g / h of a 3.5 percent sodium methoxide in methanol solution were fed to the rapeseed oil / fatty acid methyl ester mixture from a feed tank via a pump to a reactor.
  • the residence time of the mixture in the reactor was 40 minutes, the temperature in the reactor was kept at 60 ° C.
  • the mixture was separated at a residence time of 80 minutes at about 55 ° C in a light phase and heavy glycerol phase.
  • the light phase from the 1st transesterification stage was fed to a reactor from a feed tank via a pump in a second transesterification stage with a further 8.6 g / h of a 10 percent sodium methoxide in methanol solution.
  • the residence time of the mixture in the reactor was 40 minutes, the temperature in the reactor was kept at 60 ° C.
  • At the outlet of the reactor 29 g / h glycerol phase from the 1. Transesterification fed.
  • the mixture was separated at a residence time of 80 minutes at about 55 ° C in a light phase and in a heavy glycerol phase.
  • the light phase from the 2nd transesterification step was then fed to the laundry in a mixer, a dilute acid, from a storage tank via a pump.
  • the mixture was then separated in a separator into a light phase and into a heavy aqueous phase.
  • Process units - esterification with 3-stage scrubbing, catalyst regeneration and transesterification with biodiesel purification and drying - were operated continuously over a period of 2 times 5 days a week over 24 hours.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention concerne un procédé de production d'esters d'acides gras d'alcools inférieurs à partir d'acides gras contenus dans des triglycérides d'acides gras ou des esters d'acides gras d'alcools inférieurs. Ce procédé consiste à estérifier les acides gras libres contenus avec des alcools inférieurs sous pression atmosphérique et à des températures situées dans la plage d'ébullition des alcools inférieurs. Il se déroule en outre en présence de catalyseurs acides homogènes et, éventuellement, d'un solvant servant de support aux catalyseurs acides et insoluble dans les triglycérides d'acides gras ou les esters d'acides gras. On procède éventuellement à une récupération et à un recyclage des catalyseurs par distillation de l'alcool inférieur excédentaire et de l'eau de réaction. Le procédé s'achève par une transestérification subséquente avec catalyseur alcalin des triglycérides avec des alcools inférieurs à un degré de pureté nécessaire à une utilisation comme carburant pour moteurs diesel. Selon l'invention, on utilise des acides sulfoniques aliphatiques ou aromatiques dibasiques comme catalyseurs d'estérification.
PCT/AT2011/000437 2010-10-28 2011-10-27 Procédé de production d'esters d'acides gras d'alcools inférieurs WO2012054946A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ATA1786/2010A AT510636B1 (de) 2010-10-28 2010-10-28 Verfahren zur herstellung von fettsäureestern niederer alkohole
ATA1786/2010 2010-10-28

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WO2012054946A1 true WO2012054946A1 (fr) 2012-05-03

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3309241A1 (fr) * 2016-10-17 2018-04-18 UBPM Umwelt-Beratung und Produkt-Management GmbH & Co. KG Procédé et utilisation d'un agent d'oxydation permettant l'oxydation du soufre élémentaire et/ou des composés du soufre en présence de dérivés d'acide gras
CN112159727A (zh) * 2020-09-09 2021-01-01 湖北天基生物能源科技发展有限公司 一种废弃油脂的酯化方法
US11767481B2 (en) 2021-08-16 2023-09-26 Petróleo Brasileiro S.A.—Petrobras Process for producing biodiesel from acidic raw materials

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH254798A (de) * 1942-12-11 1948-05-31 Ag Georg Schicht Verfahren zur Veresterung von Fettsäuren mit niedrigmolekularen einwertigen Alkoholen.
GB612667A (en) 1945-05-29 1948-11-16 Unilever Ltd Improvements in or relating to methods of alcoholysis of low grade fatty materials
EP0127104A1 (fr) 1983-05-30 1984-12-05 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'esters d'acides gras et d'alcools aliphatiques à courte chaîne à partir de graisses et/ou d'huiles contenant des acides gras libres
EP0184740A2 (fr) 1984-12-08 1986-06-18 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'esters méthyl d'acides gras
DE3501761A1 (de) 1985-01-21 1986-07-24 Henkel KGaA, 4000 Düsseldorf Verfahren zur vorveresterung freier fettsaeuren in rohfetten und/oder -oelen
EP0593524A1 (fr) 1991-07-08 1994-04-27 Henkel Kgaa Procede de fabrication d'alkylesters inferieurs d'acides gras.
EP0658183A1 (fr) 1991-11-06 1995-06-21 Theodor Wimmer Procede de preparation d'esters d'acides gras d'alcools monovalents a courte chaine.
EP0708813A1 (fr) 1993-07-14 1996-05-01 Vogel & Noot Industrieanlagen Procede de preparation d'esters d'alkyle d'acide gras
WO2002046340A1 (fr) 2000-12-04 2002-06-13 Dr. Frische Gmbh Procede de production d'esters d'acides gras
AT410443B (de) 2000-11-08 2003-04-25 Wimmer Theodor Verfahren zur herstellung von fettsäureestern niederer alkohole
EP1322588A1 (fr) 2000-10-05 2003-07-02 BDI Anlagenbau Gesellschaft mbH Procede de production d'esters alkyliques d'acides gras
DE10311075A1 (de) * 2002-03-13 2003-09-25 Kao Corp Verfahren zur Erzeugung eines Esters
DE10243700A1 (de) 2002-09-20 2004-04-01 Oelmühle Leer Connemann Gmbh & Co. Verfahren und Vorrichtung zur Herstellung von Biodiesel
WO2004083350A1 (fr) * 2003-03-20 2004-09-30 Bdi Anlagenbau Gesellschaft M.B.H. Ester alkylique d'acide gras purifie a faible teneur en soufre et son procede de production
WO2007012097A1 (fr) 2005-07-25 2007-02-01 Bdi Biodiesel International Ag Procede de production d'alkylesters d'acide carboxylique

Patent Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH254798A (de) * 1942-12-11 1948-05-31 Ag Georg Schicht Verfahren zur Veresterung von Fettsäuren mit niedrigmolekularen einwertigen Alkoholen.
GB612667A (en) 1945-05-29 1948-11-16 Unilever Ltd Improvements in or relating to methods of alcoholysis of low grade fatty materials
EP0127104A1 (fr) 1983-05-30 1984-12-05 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'esters d'acides gras et d'alcools aliphatiques à courte chaîne à partir de graisses et/ou d'huiles contenant des acides gras libres
EP0184740A2 (fr) 1984-12-08 1986-06-18 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'esters méthyl d'acides gras
DE3501761A1 (de) 1985-01-21 1986-07-24 Henkel KGaA, 4000 Düsseldorf Verfahren zur vorveresterung freier fettsaeuren in rohfetten und/oder -oelen
US4698186A (en) 1985-01-21 1987-10-06 Henkel Kommanditgesellschaft Auf Aktien Process for the pre-esterification of free fatty acids in fats and oils
EP0593524A1 (fr) 1991-07-08 1994-04-27 Henkel Kgaa Procede de fabrication d'alkylesters inferieurs d'acides gras.
EP0658183A1 (fr) 1991-11-06 1995-06-21 Theodor Wimmer Procede de preparation d'esters d'acides gras d'alcools monovalents a courte chaine.
EP0708813A1 (fr) 1993-07-14 1996-05-01 Vogel & Noot Industrieanlagen Procede de preparation d'esters d'alkyle d'acide gras
EP1322588A1 (fr) 2000-10-05 2003-07-02 BDI Anlagenbau Gesellschaft mbH Procede de production d'esters alkyliques d'acides gras
AT410443B (de) 2000-11-08 2003-04-25 Wimmer Theodor Verfahren zur herstellung von fettsäureestern niederer alkohole
WO2002046340A1 (fr) 2000-12-04 2002-06-13 Dr. Frische Gmbh Procede de production d'esters d'acides gras
DE10311075A1 (de) * 2002-03-13 2003-09-25 Kao Corp Verfahren zur Erzeugung eines Esters
DE10243700A1 (de) 2002-09-20 2004-04-01 Oelmühle Leer Connemann Gmbh & Co. Verfahren und Vorrichtung zur Herstellung von Biodiesel
WO2004083350A1 (fr) * 2003-03-20 2004-09-30 Bdi Anlagenbau Gesellschaft M.B.H. Ester alkylique d'acide gras purifie a faible teneur en soufre et son procede de production
WO2007012097A1 (fr) 2005-07-25 2007-02-01 Bdi Biodiesel International Ag Procede de production d'alkylesters d'acide carboxylique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Ullmanns Enzyklopädie der techn. Chemie", vol. 11, 1976, pages: 432

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3309241A1 (fr) * 2016-10-17 2018-04-18 UBPM Umwelt-Beratung und Produkt-Management GmbH & Co. KG Procédé et utilisation d'un agent d'oxydation permettant l'oxydation du soufre élémentaire et/ou des composés du soufre en présence de dérivés d'acide gras
CN112159727A (zh) * 2020-09-09 2021-01-01 湖北天基生物能源科技发展有限公司 一种废弃油脂的酯化方法
CN112159727B (zh) * 2020-09-09 2022-04-12 湖北天基生物能源科技发展有限公司 一种废弃油脂的酯化方法
US11767481B2 (en) 2021-08-16 2023-09-26 Petróleo Brasileiro S.A.—Petrobras Process for producing biodiesel from acidic raw materials

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AT510636A1 (de) 2012-05-15

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