EP0489883A1 - Verfahren zur herstellung von fettsäureestern niederer alkohole - Google Patents

Verfahren zur herstellung von fettsäureestern niederer alkohole

Info

Publication number
EP0489883A1
EP0489883A1 EP91912029A EP91912029A EP0489883A1 EP 0489883 A1 EP0489883 A1 EP 0489883A1 EP 91912029 A EP91912029 A EP 91912029A EP 91912029 A EP91912029 A EP 91912029A EP 0489883 A1 EP0489883 A1 EP 0489883A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
acid
transesterification
acid esters
potassium
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Withdrawn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
EP91912029A
Other languages
German (de)
English (en)
French (fr)
Inventor
Theodor Wimmer
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.)
Vogel and Noot Industrieanlagenbau GmbH
Original Assignee
Vogel and Noot Industrieanlagenbau GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Vogel and Noot Industrieanlagenbau GmbH filed Critical Vogel and Noot Industrieanlagenbau GmbH
Publication of EP0489883A1 publication Critical patent/EP0489883A1/de
Withdrawn legal-status Critical Current

Links

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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group

Definitions

  • the present invention relates to a process for the preparation of fatty acid esters and / or fatty acid ester mixtures of lower monohydric alcohols having 1 to 5 carbon atoms by transesterification of fatty acid glycerides with the lower alcohols in the presence of basic catalysts.
  • the fatty acid esters produced according to the invention are suitable, for example, as pharmaceutical, dietetic or cosmetic raw materials, as diesel fuels, as heating oils or as intermediates for the production of further fatty acid derivatives, such as fatty alcohols, surfactants etc. and for the production of lubricants.
  • reaction conditions depend on the fatty acid glycerides used in each case.
  • 'oils and fats nag ⁇ commercial origin such as are commonly used, depending on the origin and pretreatment a free fatty acid content up to 20% and dar ⁇ may have on, temperatures in the presence of basic catalysts at Tempera ⁇ around 240 ° C and pressures of about 100 bar with 7- to 8-fold molar excess of the alcohol u can be esterified (Ullmann, Enzyklopadie d.techn.Chemie, 4. Auf! .Bd.11, p. 32, 1976) . It is also known that such transesterifications at temperatures around the
  • the boiling point of the alcohol used and at normal or only slightly increased pressure can be carried out with smaller excesses of the lower alcohols if the oils and fats used have previously reached a maximum content by methods such as distillation, alkali extraction, acid-catalyzed pre-esterification, etc. Free fatty acids of 0.5% are deacidified and then dried.
  • the main disadvantages of the known methods are that in the case of the use of high temperatures and pressures and excess alcohol, expensive reactors are required and high energy costs are incurred, or that the oils and fats used have to be deacidified and dried, which also requires expensive equipment, or that Degrees of transesterification are too low or the residual glyceride proportions are too high, which is particularly the case with the processes with low alcohol excesses or with stoichiometric amounts of alcohol, as a result of which the fatty acid esters have to be subjected to a subsequent distillation for most purposes and that the removal of the Catalyst in the case that this takes place by washing with water, causes considerable difficulties due to the formation of emulsions with regard to the subsequent phase separation, or in the case of washing out with acids a considerable amount of free fatty acids into the It comes to phase and, if an ion exchanger is used, the disadvantages associated with regeneration and the resulting wastewater occur.
  • the abovementioned disadvantages can be avoided or the above-mentioned need can be met by adding the fatty acid glycerides with 1.10 to 1.80 mol of a lower alcohol based on 1 mol of fatty acid bound as glyceride in the presence of a Alkali or alkaline earth metal compound in the form of an oxide, hydroxide, hydride, carbonate, acetate or alcoholate, but preferably in the presence of sodium hydroxide, potassium hydroxide, sodium and potassium alcoholates of the lower monohydric alcohols with one to five carbon atoms in an amount of at least 0.025 mol preferably 0.030 to 0.045 mol based on 100 grams of the fatty acid glyceride used plus the amount of the alkali metal or alkaline earth metal which is equivalent to the free fatty acids contained in the fatty acid glycerides used, and that after the transesterification and separation of the glycerol phase Distance from n impurities remaining
  • the # transesterification can be carried out in one or two or more stages, that is to say the fatty acid glyceride is either transesterified with the entire amount of lower alcohol and catalyst or only a part of the required amount of lower alcohol is used in a first stage and catalyst are used for the transesterification and, after settling and separation of a glycerol phase in a second stage or in further stages, the remaining amount (s) of lower alcohol and catalyst are used for the transesterification in the same way, the two and multi-stage Working methods have the advantage of further reducing the excess of alcohol.
  • the transesterification is carried out according to the two-stage procedure, 6/10 to 9/10 of the total amount of lower alcohol and catalyst required are preferably used in the first stage and 1/10 to 4/10 in the second stage.
  • the water can be added immediately after the second or the last stage, that is, without first separating off the glycerol phase formed in the second or last stage.
  • the transesterification by the process according to the invention is preferably carried out at ambient temperatures of approximately + 5 ° C. to + 40 ° C. and atmospheric pressure and can be carried out in any open or closed container of any size, which is advantageously equipped with a drainage device on the bottom.
  • Stirring may in batch sizes up to about 2000 liters by hand by means of an electric or air-driven simple paddle stirrer or in larger quantities advantageously in closed containers with permanently fitted R 'carried industrial .
  • the necessary manipulations can be carried out manually or automated as required.
  • Suitable fatty acid glycerides are triglycerides such as those naturally occurring as vegetable oils and fats such as soybean oil, palm oil and palm fat, coconut oil and coconut oil, sunflower oil, rapeseed oil, cotton oil, linseed oil, castor oil, peanut oil, olive oil, safflower oil, evening primrose oil, borage oil, etc.
  • locust bean oil isolated from the above-mentioned vegetable oils and 'fats or onooleat by interesterification or synthetically produced mono-, di- and triglycerides such as triolein, tripalmitin, tristearin, glycerol, glycerol distearate, etc. but ONO also waste oils such as frying oil ge fretes .
  • the vegetable oils and fats can be used in a refined or unrefined manner and can be used in addition to mucilages, cloudy substances and others Impurities contain free fatty acids up to 20% and above.
  • Suitable lower monohydric alcohols are those having one to five carbon atoms, for example methanol, ethanol, propanol, isopropanol, butanol, isobutanol, 3-methyl-1-butanol, fermentation amyl alcohol, neopentyl alcohol.
  • Suitable organic or inorganic acids are, for example, acetic acid, oxalic acid, citric acid, succinic acid, organic sulfonic acids or sulfuric acid esters, hydrochloric acid, nitric acid, sulfuric acid or phosphoric acid in a form diluted with water, or dilute aqueous solutions of acidic salts such as potassium or sodium hydrogen sulfate or sodium or potassium dihydrogen phosphate.
  • the two essential characteristics of the process according to the invention are the amount of the catalyst used, so that with a high degree of contamination and a high content of free fatty acids in the fatty acid glycerides used at ambient temperature and atmospheric pressure with only a slight excess of alcohol, any degree of esterification and problematic settling and Separation of the glycerol phase is achieved, and the addition of water or an organic or inorganic acid after the transesterification, whereby the catalyst residues are removed from the ester phase and other impurities such as glycerol, phosphatides, etc. remaining in the ester phase without any problems.
  • a dilute organic or inorganic acid such as acetic acid, oxalic acid, citric acid, succinic acid, organic sulfonic acid or organic sulfuric acid ester, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid or a dilute aqueous solution of an acidic salt such as sodium or potassium hydrogen sulfate or sodium or Potassium dihydrogen phosphate can be used in an amount of 0.1-5%, preferably 0.3-3%, the concentration of the acid or the acidic salt being measured so that it remains in the ester phase
  • Amount of the transesterification catalyst is at least equivalent and is up to 100% higher. This embodiment is mainly used when only very small amounts of residual catalyst are contained in the ester phase.
  • the glycerol phase obtained by the process according to the invention which can contain relatively large amounts of soaps, especially when fatty acid glycerides with a high proportion of free fatty acids are used, and the heavy phase obtained after the addition of water, which also contains glycerol and soaps, can advantageously be concentrated with concentrated phosphoric acid such as it is described in the "Process for the preparation of the glycerol phase resulting from the transesterification of fats and oils with lower alcohols" (A 2357/89) by the applicant.
  • the method according to the invention does not exclude that the so produced
  • Fatty acid esters are subjected to further purification by known measures, e.g. by vacuum distillation, removal of residual amounts of the lower alcohols by evaporation or blowing out, additional drying by means of silica gel, molecular sieves, coalescence aids, etc., removal of higher-melting parts of fatty acid esters by freezing out, color and odor improvement or reduction in the peroxide number Treatment with bleaching earth, etc. or by adding additives such as pour point depressants, viscosity improvers, corrosion inhibitors, odixation protection agents, cetane number improvers, etc. can be adapted to the particular intended use in a known manner.
  • additives such as pour point depressants, viscosity improvers, corrosion inhibitors, odixation protection agents, cetane number improvers, etc. can be adapted to the particular intended use in a known manner.
  • the advantages of the process according to the invention are in particular that, with only slight excesses of the lower alcohols, it is possible to work at ambient temperatures of +5 to + 40 ° C. and atmospheric pressure, that the oils and fats used do not have to be subjected to any cleaning and besides mucilages, phosphatides , and other impurities can contain free fatty acids up to 20% and above that, depending on the use of the preferably mentioned amounts of lower alcohol and transesterification catalyst, arbitrarily high degrees of transesterification can be achieved, which for many applications require further purification, for example Make it superfluous by distillation, for example if the fatty acid esters are to be used as diesel fuels, that no washing processes with water or acids and no ion exchangers are required to remove the catalyst residues, and that if necessary also at temperatures of + 5 ° C.
  • a solution of 1.83 g (0.033 mol) of potassium hydroxide in 19 ml of methanol is added added to 100 g degummed and deacidified (acid number 0.07) rapeseed oil and stirred in a 250 ml beaker with a magnetic stirrer for 15 minutes. After standing for one hour, the glycerol phase located at the bottom of the vessel is drawn off, for example by suction, into a pipette, 0.5 ml of water is added and the mixture is stirred for 10 minutes. After standing for 12 hours, the supernatant is decanted off. It consists of practically pure rapeseed fatty acid methyl ester without detectable fatty acid mono-, di- or triglycerides and an ash content of 0.004%.
  • the supernatant can be used as diesel fuel without further treatment. It contains less than 1.5% residual fatty acid glycerides and 0.008% ash.
  • a solution of 2.5 g of potassium ethylate in 18.4 g of ethanol is added to 100 g of deacidified evening primrose oil (acid number 0.07) and stirred at a temperature of 0 to + 5 ° C. for 30 minutes using a magnetic stirrer. After 2 hours the glycerol phase is separated off and the supernatant is stirred for 5 minutes with 1 ml of water. After the heavy phase has settled, the excess ester is separated off. It contains no detectable amounts of fatty acid glycerides and a potassium content of 15 ppm. The gas chromatogram of the fatty acids is identical to that of the evening primrose oil used. No isomerizations have occurred.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP91912029A 1990-06-29 1991-06-28 Verfahren zur herstellung von fettsäureestern niederer alkohole Withdrawn EP0489883A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AT1386/90 1990-06-29
AT0138690A AT394374B (de) 1990-06-29 1990-06-29 Verfahren zur herstellung von fettsaeureestern niederer alkohole

Publications (1)

Publication Number Publication Date
EP0489883A1 true EP0489883A1 (de) 1992-06-17

Family

ID=3512758

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91912029A Withdrawn EP0489883A1 (de) 1990-06-29 1991-06-28 Verfahren zur herstellung von fettsäureestern niederer alkohole

Country Status (13)

Country Link
US (1) US5399731A (cs)
EP (1) EP0489883A1 (cs)
AT (1) AT394374B (cs)
AU (1) AU641525B2 (cs)
BG (1) BG60163B2 (cs)
BR (1) BR9105796A (cs)
CA (1) CA2065306A1 (cs)
CZ (1) CZ279421B6 (cs)
HU (2) HUT59369A (cs)
PL (1) PL294039A1 (cs)
RU (1) RU2058298C1 (cs)
WO (1) WO1992000268A1 (cs)
ZA (1) ZA914972B (cs)

Families Citing this family (94)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT397510B (de) * 1991-11-06 1994-04-25 Wimmer Theodor Verfahren zur herstellung von fettsäureestern kurzkettiger alkohole
US5491226A (en) * 1994-04-06 1996-02-13 Procter & Gamble Company Process for preparing polyol polyesters having low levels of triglycerides
AT405938B (de) * 1994-06-29 1999-12-27 Lackner Johannes Kontinuierliches umesterungsverfahren, durchflussreaktor sowie trennrohr
FI95367C (fi) * 1994-09-07 1996-01-25 Raision Tehtaat Oy Ab Menetelmä synteettisen esterin valmistamiseksi kasviöljystä
DE59600783D1 (de) * 1995-04-27 1998-12-10 Sucher & Holzer Bauplan Handel Schneckenpresse
AT406870B (de) * 1995-06-16 2000-10-25 Sucher & Holzer Bauplan Handel Verfahren zur herstellung von fettsäurealkylestern
EE04110B1 (et) 1997-11-24 2003-08-15 Energea-Umwelttechnologie Gmbh Rasvhappe metüülestri valmistamise meetod ja seadmestik meetodi realiseerimiseks
AT406871B (de) * 1998-05-22 2000-10-25 Mittelbach Martin Verfahren zum verwerten eines esters, der aus mindestens einer fettsäure und einem mono-, di- oder trisaccharid gebildet ist
US6127560A (en) * 1998-12-29 2000-10-03 West Central Cooperative Method for preparing a lower alkyl ester product from vegetable oil
FR2792190B1 (fr) * 1999-04-16 2001-09-28 Sophim Procede de fabrication d'un emollient non gras a base de cires-esters
DE19925871A1 (de) 1999-06-07 2000-12-21 At Agrar Technik Gmbh Verfahren zur Herstellung von Fettsäureestern einwertiger Alkylalkohole und deren Verwendung
US6407272B1 (en) * 1999-07-14 2002-06-18 Arizona Chemical Company Secondary alcohol esters of hydroxyacids and uses thereof
WO2002002498A1 (fr) * 2000-07-04 2002-01-10 Sophim Procede de fabrication d'un emollient non gras a base de cires-esters
US6489496B2 (en) * 2000-07-12 2002-12-03 Cognis Corporation Transesterification process
MXPA03000964A (es) * 2000-08-02 2004-02-17 Mj Res & Dev L P Sistema de aceite lubricante y refrigerante.
DE10043575A1 (de) * 2000-09-05 2002-03-28 Biodiesel Plants Res & Enginee Verfahren zur kontinuierlichen Herstellung eines als Kraft- und/oder Brennstoff geeigneten Fettsäurealkylestergemisches sowie Verwendung des Fettsäurealkylesters als Kraft- bzw. Brennstoff
ATA16992000A (de) * 2000-10-05 2001-12-15 Michael Dr Koncar Verfahren zur herstellung von fettsäurealkylestern
AT410443B (de) * 2000-11-08 2003-04-25 Wimmer Theodor Verfahren zur herstellung von fettsäureestern niederer alkohole
DE10122011A1 (de) * 2001-05-07 2002-11-14 Hochschule Zittau Goerlitz Verfahren zur Herstellung von Estern aus natürlich vorkommenden Fetten und Ölen
AU778808B2 (en) * 2001-05-31 2004-12-23 Biodiesel Australia Ltd Method for production of alkyl esters
US6965044B1 (en) 2001-07-06 2005-11-15 Iowa State University Research Foundation Method of converting free fatty acids to fatty acid methyl esters with small excess of methanol
DE10135297B4 (de) * 2001-07-19 2010-05-12 Rmenergy Umweltverfahrenstechnik Gmbh Vorrichtung und Verfahren zur Herstellung von Fettsäurealkylester
ES2194598B2 (es) * 2002-01-25 2006-04-01 Universidad Complutense De Madrid Procedimiento de transesterificacion de trigliceridos con monoalcoholes de bajo peso molecular para obtencion de esteres de alcoholes ligeros utilizando catalizadores mixtos.
EP1477549B1 (en) * 2002-02-20 2008-10-22 Revo International Inc. Method of producing fatty acid alkyl ester for diesel fuel oil
FR2838433B1 (fr) * 2002-04-11 2005-08-19 Inst Francais Du Petrole Procede de production d'esters alkyliques a partir d'une huile vegetale ou animale et d'un monoalcool aliphatique
AT504727A1 (de) * 2002-04-12 2008-07-15 Energea Umwelttechnologie Gmbh Verfahren und anlage zur veresterung von fettsäuren
MXPA04010803A (es) 2002-04-29 2005-03-07 Dow Global Technologies Inc Procesos quimicos integrados para la utilizacion industrial de aceites de semilla.
CA2507329A1 (en) * 2002-11-27 2004-06-10 Biodiesel Australia Ltd Method for production of alkyl esters
DE10257215B4 (de) * 2002-12-07 2005-12-22 Lurgi Ag Verfahren zur Verbesserung der Langzeitstabilität von Biodiesel
US7871448B2 (en) * 2003-01-27 2011-01-18 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US8088183B2 (en) * 2003-01-27 2012-01-03 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US7806945B2 (en) * 2003-01-27 2010-10-05 Seneca Landlord, Llc Production of biodiesel and glycerin from high free fatty acid feedstocks
US9725397B2 (en) 2003-01-27 2017-08-08 REG Seneca, LLC Production of biodiesel and glycerin from high free fatty acid feedstocks
CN100412169C (zh) * 2003-03-20 2008-08-20 迈克尔·F·佩莱 精制生物柴油的方法和装置
KR100566106B1 (ko) 2003-03-28 2006-03-30 한국에너지기술연구원 바이오디젤유의 제조방법
US8246699B2 (en) * 2003-05-19 2012-08-21 Malaysian Palm Oil Board Palm diesel with low pour point for cold climate countries
US20040231236A1 (en) * 2003-05-19 2004-11-25 May Choo Yuen Palm diesel with low pour point for cold climate countries
US20040231234A1 (en) * 2003-05-19 2004-11-25 May Choo Yuen Palm diesel with low pour point for climate countries
US20050027137A1 (en) * 2003-07-29 2005-02-03 Hooker Jeffrey D. Apparatus and method for the production of fatty acid alkyl ester
US6822105B1 (en) 2003-08-12 2004-11-23 Stepan Company Method of making alkyl esters using glycerin
US7579508B2 (en) * 2003-09-09 2009-08-25 Kao Corporation Process for producing alcohol
US7619104B2 (en) * 2005-04-04 2009-11-17 Renewable Products Development Laboratories, Inc. Process for producing biodiesel or fatty acid esters from multiple triglyceride feedstocks
AT502218B1 (de) * 2005-07-25 2010-09-15 Bdi Biodiesel Internat Ag Verfahren zur herstellung von carbonsäurealkylestern
JP4219349B2 (ja) * 2005-09-16 2009-02-04 富士フイルム株式会社 脂肪酸アルキルエステルの製造方法及び燃料
US20070087085A1 (en) * 2005-10-17 2007-04-19 Bunge Oils, Inc. Protein-containing food product and coating for a food product and method of making same
US20080113067A1 (en) * 2005-10-17 2008-05-15 Monoj Sarma Protein-Containing Food Product and Coating for a Food Product and Method of Making Same
US20070148311A1 (en) * 2005-12-22 2007-06-28 Bunge Oils, Inc. Phytosterol esterification product and method of make same
US7828978B2 (en) * 2006-01-11 2010-11-09 Doug Geier Simultaneous synthesis and purification of a fatty acid monoester biodiesel fuel
GB2438403B (en) * 2006-05-25 2011-02-23 Viktor Fedorovych Dekhtiaruk Manufacture of biodiesel
US8378132B2 (en) * 2007-02-16 2013-02-19 Daniel W. Lemke Process for producing methyl esters
WO2008112910A1 (en) * 2007-03-14 2008-09-18 Endicott Biofuels Ii, Llc Methods for producing triol ethers by reactive distillation
BRPI0808893A2 (pt) * 2007-03-14 2015-03-24 Endicott Biofuels Ii Llc Produção de combustíveis de biodiesel que possuem baixos níveis de glicerina e de enxofre
DE102007016157A1 (de) 2007-04-02 2008-10-09 Bayer Technology Services Gmbh Verfahren zur Trennung von Produktgemischen aus Umesterungsreaktionen
CZ301958B6 (cs) * 2007-04-16 2010-08-11 Univerzita Pardubice Zpusob výroby bionafty z rostlinných oleju, zejména z repkového oleje
US20080282606A1 (en) * 2007-04-16 2008-11-20 Plaza John P System and process for producing biodiesel
WO2009017957A1 (en) * 2007-07-31 2009-02-05 Endicott Biofuels Ii, Llc Production of alkyl esters from high fatty acid feedstocks
US20090049739A1 (en) * 2007-07-31 2009-02-26 Endicott Biiofuels Ii, Llc Production of Fuels with Superior Low Temperature Properties from Tall Oil or Fractionated Fatty Acids
WO2009017958A1 (en) * 2007-07-31 2009-02-05 Endicott Biofuels Ii, Llc Production of renewable diesel by pyrolysis and esterification
US20090031618A1 (en) * 2007-07-31 2009-02-05 Endicott Biofuels Ii, Llc Vacuum Distillation Process
US20110139106A1 (en) * 2007-08-09 2011-06-16 21St Century R & D, Llc Modification of fats and oils for fuel and lubricating applications
US20090038692A1 (en) * 2007-08-09 2009-02-12 21St Century R & D, Llc Modification of vegetable oils for fuel applications
US8105398B2 (en) * 2007-08-27 2012-01-31 Endicott Biofuels Ii, Llc Production of ester-based fuels such as biodiesel from renewable starting materials
US8901330B2 (en) * 2007-08-29 2014-12-02 Sauber Llc Method for production of biofuel
AU2014240324B2 (en) * 2007-08-29 2016-06-30 Agron Bioenergy Llc Method for production of biofuel
WO2009038864A1 (en) * 2007-09-19 2009-03-26 Endicott Biofuels Ii, Llc Method for obtaining biodiesel, alternative fuels and renewable fuels tax credits and treatment
WO2009038865A1 (en) * 2007-09-19 2009-03-26 Endicott Biofuels Ii, Llc Method for obtaining biodiesel, alternative fuels and renewable fuels tax credits and treatment
RU2366646C2 (ru) * 2007-10-11 2009-09-10 Общество с ограниченной ответственностью "Научно-производственное объединение "Нефтепромхим" ООО "НПО "Нефтепромхим" Способ получения сложных эфиров жирных кислот
US7718833B2 (en) 2007-11-02 2010-05-18 Johann Haltermann, Ltd. Purification of glycerin obtained as a bioproduct from the transesterification of triglycerides in the synthesis of biofuel
US20090119979A1 (en) * 2007-11-08 2009-05-14 Imperial Petroleum, Inc. Catalysts for production of biodiesel fuel and glycerol
RU2381262C2 (ru) * 2008-04-03 2010-02-10 Государственное научное учреждение Всероссийский научно-исследовательский институт мясной промышленности им. В.М. Горбатова Российской академии сельскохозяйственных наук Способ переработки животного жира в жидкое топливо
RU2385900C1 (ru) * 2008-07-01 2010-04-10 Государственное научное учреждение Всероссийский научно-исследовательский институт мясной промышленности имени В.М. Горбатова Российской академии сельскохозяйственных наук Способ получения жидкого биотоплива
FR2938257B1 (fr) 2008-11-10 2012-08-03 Arkema France Procede de transesterification d'huiles hydroxylees
US8735640B2 (en) 2009-10-12 2014-05-27 Elevance Renewable Sciences, Inc. Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks
US9365487B2 (en) 2009-10-12 2016-06-14 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US9382502B2 (en) 2009-10-12 2016-07-05 Elevance Renewable Sciences, Inc. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks
BR112012008608B8 (pt) 2009-10-12 2022-06-14 Elevance Renewable Sciences Método de refinação de óleo natural
US9175231B2 (en) * 2009-10-12 2015-11-03 Elevance Renewable Sciences, Inc. Methods of refining natural oils and methods of producing fuel compositions
US9051519B2 (en) 2009-10-12 2015-06-09 Elevance Renewable Sciences, Inc. Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters
US9169447B2 (en) * 2009-10-12 2015-10-27 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US9222056B2 (en) * 2009-10-12 2015-12-29 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US9000246B2 (en) 2009-10-12 2015-04-07 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
BR112012017956B1 (pt) 2010-01-22 2020-04-07 Archer Daniels Midland Co composição de poli (haleto de vinila)
DE102010055969A1 (de) * 2010-12-23 2012-06-28 Süd-Chemie AG Verfahren zur Aufreinigung von organischen Flüssigkeiten
JP5944303B2 (ja) * 2011-12-08 2016-07-05 花王株式会社 脂肪酸モノグリセライド含有混合物の製造方法。
US9388098B2 (en) 2012-10-09 2016-07-12 Elevance Renewable Sciences, Inc. Methods of making high-weight esters, acids, and derivatives thereof
AT513799B1 (de) 2012-12-18 2020-02-15 Mag Schell Klaus Verfahren zur Herstellung eines Bio-Diesel-Kraftstoffes mit einem speziell ausgelegten Reaktor und quasi katalytisch wirksamer nanoskalig strukturierter Materialoberfläche des Reaktors
US9738855B2 (en) 2013-02-04 2017-08-22 Tehnochem Process for converting low and high free fatty acid containing oils into no free fatty acid containing oils and associated systems and devices
US9365801B2 (en) 2013-02-04 2016-06-14 Technochem International, Inc. Process of converting low and high free fatty acid containing oils into no free fatty acid containing oils
EP3008200B1 (en) 2013-06-11 2020-01-08 Renewable Energy Group, Inc. Production of biodiesel and products obtained therefrom
US9328054B1 (en) 2013-09-27 2016-05-03 Travis Danner Method of alcoholisis of fatty acids and fatty acid gyicerides
CN105647654A (zh) * 2016-01-18 2016-06-08 佳力士添加剂（海安）有限公司 单甘酯的制备工艺
US10072231B2 (en) 2016-12-02 2018-09-11 Ag Chem, Llc Process for the conversion of free fatty acids to glycerol esters and production of novel catalyst systems
EP4071226A1 (en) 2021-04-08 2022-10-12 AT Agrar-Technik Int. GmbH Process for producing fatty acid alkyl esters
CN113731487A (zh) * 2021-08-17 2021-12-03 沈阳工业大学 再生甲氧基甲酸钠复合物催化剂及催化合成emc的方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2360844A (en) * 1941-11-26 1944-10-24 Du Pont Preparation of detergents
JPS5665097A (en) * 1979-05-30 1981-06-02 Lion Corp Manufacture of fatty acid lower alcohol ester
JPS56120799A (en) * 1980-02-28 1981-09-22 Lion Corp Manufacture of high quality fatty ester
DE3932514A1 (de) * 1989-09-29 1991-04-18 Henkel Kgaa Kontinuierliches verfahren zum herstellen niederer alkylester

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9200268A1 *

Also Published As

Publication number Publication date
CA2065306A1 (en) 1991-12-30
AU8074291A (en) 1992-01-23
CZ279421B6 (cs) 1995-04-12
ZA914972B (en) 1992-04-29
ATA138690A (de) 1991-09-15
RU2058298C1 (ru) 1996-04-20
AT394374B (de) 1992-03-25
BR9105796A (pt) 1992-09-22
HU209912B (en) 1994-11-28
BG60163B2 (bg) 1993-11-30
AU641525B2 (en) 1993-09-23
WO1992000268A1 (de) 1992-01-09
HUT59369A (en) 1992-05-28
PL294039A1 (en) 1992-11-30
US5399731A (en) 1995-03-21
CS58792A3 (en) 1992-10-14

Similar Documents

Publication Publication Date Title
AT394374B (de) Verfahren zur herstellung von fettsaeureestern niederer alkohole
AT397510B (de) Verfahren zur herstellung von fettsäureestern kurzkettiger alkohole
EP1322588B1 (de) Verfahren zur herstellung von fettsäurealkylestern
DE69808029T2 (de) Verfahren zum Herstellen von Fettsäureester
EP0198243B1 (de) Verfahren zur Herstellung von Carbonsäurealkylestern, insbesondere Fettsäurealkylestern
DE69701014T2 (de) Verfahren zur Herstellung von Fettsäureäthylestern
EP1910267B1 (de) Verfahren zur herstellung von carbonsäurealkylestern
EP1183225A1 (de) Verfahren zur herstellung von fettsäureestern einwertiger alkylalkohole und deren verwendung
EP0629185A1 (de) Verfahren zur herstellung von fettsäureestern niederer alkohole
DE4122530A1 (de) Verfahren zur herstellung von fettsaeureniedrigalkylestern
EP2358851B1 (de) Verwendung von methansulfonsäure zur herstellung von fettsäureestern
AT410443B (de) Verfahren zur herstellung von fettsäureestern niederer alkohole
AT397966B (de) Verfahren zur herstellung von fettsäureestern niederer einwertiger alkohole
EP1358306A1 (de) Verfahren zur umesterung von fett und/oder öl mittels alkoholyse
AT394571B (de) Verfahren zur herstellung von fettsaeureestern kurzkettiger alkohole
AT392977B (de) Verfahren zur aufbereitung der bei der umesterung von fetten und oelen mit niederen alkoholen anfallenden glycerinphase
EP1092703B1 (de) Verfahren zur Herstellung von Fettsäuremethylestern
EP0728176B1 (de) Verfahren zur herstellung von fettsäureniedrigalkylestern
AT412280B (de) Gereinigter fettsäurealkylester mit niedrigem schwefelgehalt und verfahren zu seiner herstellung
DE10157067A1 (de) Verfahren zur Entsäuerung von natürlichen Fetten und Ölen
WO2010037772A1 (de) Verfahren zur herstellung von biodiesel
DE19956599C2 (de) Verfahren zur Herstellung von entsäuerten Triglyceriden
AT406870B (de) Verfahren zur herstellung von fettsäurealkylestern
WO1999057091A1 (de) Verfahren zur herstellung von fettsäureestern aus triglyceriden
WO2008049260A2 (de) Verfahren zur herstellung von fettsäureestern

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19920214

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE

17Q First examination report despatched

Effective date: 19931118

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19941213