EP0629185A1 - Procede de fabrication d'esters d'acides gras d'alcools inferieurs - Google Patents

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

Info

Publication number
EP0629185A1
EP0629185A1 EP94904961A EP94904961A EP0629185A1 EP 0629185 A1 EP0629185 A1 EP 0629185A1 EP 94904961 A EP94904961 A EP 94904961A EP 94904961 A EP94904961 A EP 94904961A EP 0629185 A1 EP0629185 A1 EP 0629185A1
Authority
EP
European Patent Office
Prior art keywords
phase
fatty acid
glycerol
transesterification
glycerin
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Withdrawn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
EP94904961A
Other languages
German (de)
English (en)
Inventor
Manfred Gross
Gerda Tschampel
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.)
CHEMISCHE und PHARMAZEUTISCHE FABRIKEN FAHLBERG-LIST GmbH
Original Assignee
CHEMISCHE und PHARMAZEUTISCHE FABRIKEN FAHLBERG-LIST 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 CHEMISCHE und PHARMAZEUTISCHE FABRIKEN FAHLBERG-LIST GmbH filed Critical CHEMISCHE und PHARMAZEUTISCHE FABRIKEN FAHLBERG-LIST GmbH
Publication of EP0629185A1 publication Critical patent/EP0629185A1/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Withdrawn legal-status Critical Current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
    • C10L1/02—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.
EP94904961A 1993-01-22 1994-01-19 Procede de fabrication d'esters d'acides gras d'alcools inferieurs Withdrawn EP0629185A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4301686 1993-01-22
DE4301686A DE4301686C1 (de) 1993-01-22 1993-01-22 Verfahren zur Herstellung von Fettsäureestern niederer Alkohole
PCT/DE1994/000057 WO1994017027A1 (fr) 1993-01-22 1994-01-19 Procede de fabrication d'esters d'acides gras d'alcools inferieurs

Publications (1)

Publication Number Publication Date
EP0629185A1 true EP0629185A1 (fr) 1994-12-21

Family

ID=6478726

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94904961A Withdrawn EP0629185A1 (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)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5424467A (en) * 1993-07-14 1995-06-13 Idaho Research Foundation Method for purifying alcohol esters
FR2748490B1 (fr) * 1996-05-07 1998-06-19 Inst Francais Du Petrole Procede de fabrication d'esters ethyliques
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
DE10022966A1 (de) * 2000-05-11 2001-11-22 Cognis Deutschland Gmbh Verfahren zur Herstellung von Esterquats
WO2002046339A2 (fr) * 2000-12-04 2002-06-13 Dr. Frische Gmbh Procede de pretraitement d'huiles brutes et de graisses brutes pour la production d'esters d'acides gras
WO2005037969A2 (fr) * 2003-10-09 2005-04-28 The Dallas Group Of America, Inc. Purification de biodiesel a l'aide de matieres adsorbantes
DK1996680T3 (en) * 2004-10-20 2014-03-24 Council Scient Ind Res Improved process for the preparation of fatty acid methyl ester (biodiesel) from triglyceride oil by transesterification
US8062391B2 (en) 2005-02-21 2011-11-22 Kagoshima University Method for purifying biodiesel fuel
DE102005059002A1 (de) 2005-12-08 2007-06-14 Helmut KÖRBER Verfahren zur Entfernung von Verunreinigungen aus Fettsäuremethylestern auf Basis natürlicher Fette und Öle
TR200703297A2 (tr) * 2007-05-15 2007-11-21 Keski̇nler Bülent Bitkisel yağlardan serbest yağ asitlerinin uzaklaştırılması için bir proses
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
CN102177130A (zh) * 2008-12-04 2011-09-07 国际壳牌研究有限公司 制备链烷二醇和二烷基碳酸酯的方法
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

Family Cites Families (5)

* 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
JPS56120799A (en) * 1980-02-28 1981-09-22 Lion Corp Manufacture of high quality fatty ester
EP0131991B1 (fr) * 1983-07-12 1986-12-03 Metallgesellschaft Ag Procédé continu d'alcoolyse
AT386222B (de) * 1986-09-02 1988-07-25 Hans Dr Junek Verfahren und vorrichtung zur herstellung eines als kraft- bzw. brennstoff geeigneten fettsaeureestergemisches
ES2062293T3 (es) * 1989-04-05 1994-12-16 Unilever Nv Procedimiento para la produccion de monoesteres alquilicos inferiores de acidos grasos.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9417027A1 *

Also Published As

Publication number Publication date
HUT68284A (en) 1995-06-28
HU214203B (hu) 1998-01-28
HU9402716D0 (en) 1994-12-28
RU94042226A (ru) 1996-07-20
DE4301686C1 (de) 1994-03-31
WO1994017027A1 (fr) 1994-08-04
PL305263A1 (en) 1995-01-09
RU2127251C1 (ru) 1999-03-10

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