WO1994017027A1 - Procede de fabrication d'esters d'acides gras d'alcools inferieurs - Google Patents

Procede de fabrication d'esters d'acides gras d'alcools inferieurs Download PDF

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Publication number
WO1994017027A1
WO1994017027A1 PCT/DE1994/000057 DE9400057W WO9417027A1 WO 1994017027 A1 WO1994017027 A1 WO 1994017027A1 DE 9400057 W DE9400057 W DE 9400057W WO 9417027 A1 WO9417027 A1 WO 9417027A1
Authority
WO
WIPO (PCT)
Prior art keywords
phase
fatty acid
glycerol
transesterification
glycerine
Prior art date
Application number
PCT/DE1994/000057
Other languages
German (de)
English (en)
Inventor
Manfred Gross
Gerda Tschampel
Original Assignee
Chemische Und Pharmazeutische Fabriken Fahlberg-List Gmbh I.L.
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 Chemische Und Pharmazeutische Fabriken Fahlberg-List Gmbh I.L. filed Critical Chemische Und Pharmazeutische Fabriken Fahlberg-List Gmbh I.L.
Priority to RU94042226A priority Critical patent/RU2127251C1/ru
Priority to PL94305263A priority patent/PL305263A1/xx
Priority to EP94904961A priority patent/EP0629185A1/fr
Publication of WO1994017027A1 publication Critical patent/WO1994017027A1/fr

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
    • C10L1/02—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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • 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
    • 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

Definitions

  • the present invention relates to a process for the preparation of fatty acid esters of lower monohydric n-alcohols having 1 to 4 carbon atoms by transesterification of fatty acid glycerides with the corresponding alcohols in the presence of basic catalysts under special work-up conditions.
  • the disadvantages of the known processes can be avoided if the fatty acid glycerides are mixed with a lower monohydric n-alcohol with 1 to 4 carbon atoms in a molar ratio of 1: 3 to 1: 6, in particular 1: 3.5 to 1: 5 in the presence of an alkali catalyst, in particular sodium or potassium hydroxide, dissolved in the lower alcohol in an amount of 0.01 mol to 0.05 mol, in particular 0.02 mol to 0.035 mol, based on 100 g of the fatty acid glyceride used plus the alkali - amount, which is equivalent to the acidic components contained in the fatty acid glycerides, at temperatures from ambient temperature to 70 ° C, in particular at 40 ° C to 60 ° C, after an at least two-step conversion process, after transesterification, the fatty acid ester phase to remove remaining impurities cleaning and a better phase separation with glycerin, crude glycerin from the working-up
  • the amount of glycerin used for washing is dependent on the amount of impurities remaining in the ester phase, in particular dissolved glycerol, catalyst residue, soaps, excess alcohol and other substances which reduce the specific weight of the heavier glycerol phase which precipitates and on the purity and density of the used washing glycerin.
  • washing glycerol it is advantageous to choose the amount and quality of the washing glycerol in such a way that a density of 1.03 g / cm 3 (20 ° C.) in the glycerol phase to be separated is not undercut.
  • the washing process can be carried out with stirring using the technological systems customary for this after the transesterification has taken place and before or after the separation of the last glycerol phase in multi-stage procedures, although it is not necessary to separate the last glycerol phase before adding the washing glycerol.
  • the process according to the invention gives a good washing and cleaning effect of the ester phase but no phase separation problems, and the ester phase can be separated after a short time, which also means that space-time Yield of the process is significantly improved.
  • the glycerol wash neither delays the reaction equilibrium of the transesterification reaction, nor increases the concentration of free or bound glycerol in the end product.
  • the complete separation of the heavier glycerol phase can optionally be accelerated or improved by using a coalescence separator or separator.
  • Another disadvantage of the known processes is the use of aqueous organic or inorganic acids, acid salts or of ion exchangers for neutralizing the alkalinity of the ester phase.
  • the acids are released from the fatty acid salts still present, which leads to an increase in the acid number of the end product, since the free fatty acids dissolve better in the ester phase than in an aqueous glycerol phase.
  • the residual alkalinity of the ester phase is removed by treatment with bleaching earth, silica or other physico-chemically similar substances.
  • the ester phase with such a substance in particular in an amount of 1% to 5% 1.5% to 3% based on the fatty acid glyceride used at process temperature delt.
  • This process is not identical to the known bleaching earth treatment in the refining of vegetable oils.
  • the treatment can be carried out separately or in conjunction with the removal of the volatile components from the ester phase.
  • the separation of the contaminated bleaching earth from the ester phase is carried out using filters or centrifuges and is unproblematic.
  • bleaching earth or similar adsorbents has the further advantage that other hydrophilic impurities such as e.g. B. glycerol, glycerides or oil-soluble plant ingredients are removed with.
  • other hydrophilic impurities such as e.g. B. glycerol, glycerides or oil-soluble plant ingredients are removed with.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (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)

Abstract

L'invention concerne un procédé de fabrication d'esters d'acides gras de n-alcools inférieurs monovalents, par transestérification de glycérides d'acides gras en présence de catalyseurs basiques. Le procédé selon l'invention est caractérisé en ce qu'après transestérification, la phase ester est lavée avec de la glycérine, de la glycérine brute provenant du retraitement de la glycérine, ou avec la phase glycérinée d'une étape précédente de transestérification, séparée complètement de la dernière phase glycérinée, puis traitée par de l'argile absorbante, de l'acide silicique ou d'autres substances physico-chimiques analogues. Contrairement aux procédés connus, il est alors possible d'obtenir, à partir d'huiles naturelles non raffinées, sans processus de lavage à l'eau et sans utilisation d'acides aqueux pour la neutralisation du catalyseur dans la phase ester, des qualités de produits qu'il est normalement possible d'obtenir qu'au moyen d'huiles purifiées et d'étapes de traitement en milieu aqueux.
PCT/DE1994/000057 1993-01-22 1994-01-19 Procede de fabrication d'esters d'acides gras d'alcools inferieurs WO1994017027A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
RU94042226A RU2127251C1 (ru) 1993-01-22 1994-01-19 Способ получения сложных эфиров жирных кислот
PL94305263A PL305263A1 (en) 1993-01-22 1994-01-19 Method of obtaining fatty acid ester with lower alcohols
EP94904961A EP0629185A1 (fr) 1993-01-22 1994-01-19 Procede de fabrication d'esters d'acides gras d'alcools inferieurs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4301686A DE4301686C1 (de) 1993-01-22 1993-01-22 Verfahren zur Herstellung von Fettsäureestern niederer Alkohole
DEP4301686.3 1993-01-22

Publications (1)

Publication Number Publication Date
WO1994017027A1 true WO1994017027A1 (fr) 1994-08-04

Family

ID=6478726

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1994/000057 WO1994017027A1 (fr) 1993-01-22 1994-01-19 Procede de fabrication d'esters d'acides gras d'alcools inferieurs

Country Status (6)

Country Link
EP (1) EP0629185A1 (fr)
DE (1) DE4301686C1 (fr)
HU (1) HU214203B (fr)
PL (1) PL305263A1 (fr)
RU (1) RU2127251C1 (fr)
WO (1) WO1994017027A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995002662A1 (fr) * 1993-07-14 1995-01-26 Idaho Research Foundation, Inc. Procede de purification d'esters d'alcool
EP0806471A1 (fr) * 1996-05-07 1997-11-12 Institut Francais Du Petrole Procédé de fabrication d'esters éthyliques d'acides gras
WO1999024387A1 (fr) * 1997-11-10 1999-05-20 The Procter & Gamble Company Procede de fabrication d'alkylesters inferieurs d'acides gras de haute purete
US6965043B1 (en) 1997-11-10 2005-11-15 Procter + Gamble Co. Process for making high purity fatty acid lower alkyl esters
EP1867702A1 (fr) * 2005-02-21 2007-12-19 Kagoshima University Procédé de purification de carburant biodiesel
WO2008140432A1 (fr) * 2007-05-15 2008-11-20 Bulent Keskinler Procédé pour l'élimination des acides gras libres des huiles végétales

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10022966A1 (de) * 2000-05-11 2001-11-22 Cognis Deutschland Gmbh Verfahren zur Herstellung von Esterquats
PL198770B1 (pl) * 2000-12-04 2008-07-31 Westfalia Separator Ag Sposób wstępnej obróbki surowych olejów i surowych tłuszczów do wytwarzania estrów kwasów tłuszczowych
ES2337692T3 (es) * 2003-10-09 2010-04-28 The Dallas Group Of America, Inc. Purificacion de biodiesel con materiales adsorbentes.
AU2004324250B2 (en) * 2004-10-20 2010-03-18 Council Of Scientific And Industrial Research Improved process for the preparation of fatty acid methyl ester (Biodiesel) from triglyceride oil through transesterification
DE102005059002A1 (de) 2005-12-08 2007-06-14 Helmut KÖRBER Verfahren zur Entfernung von Verunreinigungen aus Fettsäuremethylestern auf Basis natürlicher Fette und Öle
DE102007056703A1 (de) * 2007-11-24 2009-06-04 Lurgi Gmbh Verfahren zum Herstellen von Fettsäureester bzw. Fettsäureethylester
DE102007059620A1 (de) * 2007-12-12 2009-06-18 Bundesrepublik Deutschland, vertreten durch den Präsidenten der Bundesanstalt für Geowissenschaften und Rohstoffe Aufreinigung von Biodiesel mittels Allophan und/oder Imogolit
JP5596049B2 (ja) * 2008-12-04 2014-09-24 シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー アルカンジオールおよびジアルキルカーボネートの調製方法
DE102009006921A1 (de) * 2009-02-02 2010-08-05 Lurgi Gmbh Verfahren, Anlage und Mittel zur Vermeidung von Sterolglycoside enthaltenden Ausfällungen bei der Herstellung von Fettsäurealkylestern
DE102009041120A1 (de) 2009-09-15 2011-03-24 Lurgi Gmbh Verfahren zur Reinigung von stark mit Verseifungsprodukten belastetem Fettsäurealkylester
RU2453530C2 (ru) * 2010-06-28 2012-06-20 Государственное образовательное учреждение высшего профессионального образования Самарский государственный технический университет Способ получения сложных эфиров
DE102011079550A1 (de) 2011-07-21 2013-01-24 Evonik Degussa Gmbh Alkalimetall-Glycerate zur Entsäuerung und Trocknung von Fettsäureestern

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3107318A1 (de) * 1980-02-28 1981-12-17 Lion Corp., Tokyo Verfahren zur herstellung hochwertiger fettsaeureester
EP0131991A1 (fr) * 1983-07-12 1985-01-23 Metallgesellschaft Ag Procédé continu d'alcoolyse
EP0391485A1 (fr) * 1989-04-05 1990-10-10 Unilever N.V. Procédé de production de monoesters d'alkyl inférieur d'acides gras

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5665097A (en) * 1979-05-30 1981-06-02 Lion Corp Manufacture of fatty acid lower alcohol ester
AT386222B (de) * 1986-09-02 1988-07-25 Hans Dr Junek Verfahren und vorrichtung zur herstellung eines als kraft- bzw. brennstoff geeigneten fettsaeureestergemisches

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3107318A1 (de) * 1980-02-28 1981-12-17 Lion Corp., Tokyo Verfahren zur herstellung hochwertiger fettsaeureester
EP0131991A1 (fr) * 1983-07-12 1985-01-23 Metallgesellschaft Ag Procédé continu d'alcoolyse
EP0391485A1 (fr) * 1989-04-05 1990-10-10 Unilever N.V. Procédé de production de monoesters d'alkyl inférieur d'acides gras

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995002662A1 (fr) * 1993-07-14 1995-01-26 Idaho Research Foundation, Inc. Procede de purification d'esters d'alcool
US5424467A (en) * 1993-07-14 1995-06-13 Idaho Research Foundation Method for purifying alcohol esters
EP0806471A1 (fr) * 1996-05-07 1997-11-12 Institut Francais Du Petrole Procédé de fabrication d'esters éthyliques d'acides gras
FR2748490A1 (fr) * 1996-05-07 1997-11-14 Inst Francais Du Petrole Procede de fabrication d'esters ethyliques
US6013817A (en) * 1996-05-07 2000-01-11 Institut Francais Du Petrole Process for the production of ethyl esters
WO1999024387A1 (fr) * 1997-11-10 1999-05-20 The Procter & Gamble Company Procede de fabrication d'alkylesters inferieurs d'acides gras de haute purete
US6965043B1 (en) 1997-11-10 2005-11-15 Procter + Gamble Co. Process for making high purity fatty acid lower alkyl esters
EP1867702A1 (fr) * 2005-02-21 2007-12-19 Kagoshima University Procédé de purification de carburant biodiesel
EP1867702A4 (fr) * 2005-02-21 2010-02-24 Univ Kagoshima Procédé de purification de carburant biodiesel
US8062391B2 (en) 2005-02-21 2011-11-22 Kagoshima University Method for purifying biodiesel fuel
WO2008140432A1 (fr) * 2007-05-15 2008-11-20 Bulent Keskinler Procédé pour l'élimination des acides gras libres des huiles végétales

Also Published As

Publication number Publication date
RU2127251C1 (ru) 1999-03-10
HUT68284A (en) 1995-06-28
RU94042226A (ru) 1996-07-20
HU9402716D0 (en) 1994-12-28
EP0629185A1 (fr) 1994-12-21
PL305263A1 (en) 1995-01-09
DE4301686C1 (de) 1994-03-31
HU214203B (hu) 1998-01-28

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