EP1308498A1 - Procédé de production d'esters d'acides gras à partir de graisses et d'huiles non désacidifiées - Google Patents

Procédé de production d'esters d'acides gras à partir de graisses et d'huiles non désacidifiées Download PDF

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Publication number
EP1308498A1
EP1308498A1 EP02023941A EP02023941A EP1308498A1 EP 1308498 A1 EP1308498 A1 EP 1308498A1 EP 02023941 A EP02023941 A EP 02023941A EP 02023941 A EP02023941 A EP 02023941A EP 1308498 A1 EP1308498 A1 EP 1308498A1
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EP
European Patent Office
Prior art keywords
transesterification
stage
process according
carried out
range
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.)
Granted
Application number
EP02023941A
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German (de)
English (en)
Other versions
EP1308498B1 (fr
Inventor
Lothar Friesenhagen
Bernhard Dr. Gutsche
Bernard Schleper
Christian Dr. Pelzer
Nicole Schöffler
Sabine Dr. Both
Claudius Lott
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.)
Cognis IP Management GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
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Publication of EP1308498A1 publication Critical patent/EP1308498A1/fr
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Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange

Definitions

  • synthetic triglycerides are also possible as starting materials, since these generally do not have any particular acid numbers, the problem described at the outset does not arise or only to a minor extent.
  • natural triglycerides i.e. vegetable or animal fats or oils
  • suitable feedstocks are palm oil, palm kernel oil, coconut oil, beef tallow, sunflower oil or rapeseed oil and also their mixtures.
  • the first step in the process takes advantage of the fact that esterifications are only acid-catalyzed run and are faster than transesterification reactions, which in turn both by Acids as can be catalyzed by bases. So while in usual procedures the humiliation the acid number by neutralization with the basic transesterification catalyst and soap formation takes place, according to the invention, an esterification of the free fatty acids takes place with the formation of alkyl esters instead, which are preferably directly identical to the target product.
  • Lewis acids which are selected from the Group formed by alkali salts of organic carboxylic acids with 1 to 4 carbon atoms, Alkali carbonates, alkali hydrogen carbonates and solutions of the catalysts in fatty acids or Partial glycerides.
  • Typical examples are alkali acetates, alkali propionates, alkali butyrates, sodium carbonate, Sodium hydrogen carbonate, potassium carbonate and potassium hydrogen carbonate. Particularly preferred are potassium salts, especially potassium acetate, which may be present in fatty acids or monoglycerides is solved.
  • the amount of catalyst is generally 0.1 to 2, preferably 0.5 to 1 wt .-% based on the starting materials.
  • the reaction is usually carried out at temperatures in the range of 100 to 300, preferably 150 to 240 ° C carried out.
  • the print range can be between 5 and 100 bar and is preferably 60 to 90 bar.
  • the amount of methanol is calculated according to the Acid number, i.e. according to the amount of available fatty acids. Usually alcohol, preferably methanol, and triglyceride in a weight ratio of 1: 2 to 2: 1.
  • the second stage of the transesterification typically at milder temperatures in the range from 20 to 200, preferably 70 to 150 ° C and lower pressures in the range of 1 to 10, preferably 1 to 5 bar. It is usually not necessary to add fresh alcohol, although this is of course possible consists.
  • Table 3 shows a list of the reaction components in percent by weight without methanol: Composition (expressed as area percent) composition TG DG MG Methylester fatty acid glycerin raw coconut oil 92.8 2.3 --- --- 4.9 --- Anfahrgemisch 91.5 2.8 --- --- 5.7 --- Total final sample --- 2.1 10.8 75.8 1.5 10.3 Final test upper phase after methanol separation --- 1.0 12.2 85.1 1.1 1.6 Final test sub-phase after methanol separation --- 0.1 0.4 1.2 2.0 96.7

Landscapes

  • Chemical & Material Sciences (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)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP02023941A 2001-11-06 2002-10-25 Procédé de production d'esters d'acides gras à partir de graisses et d'huiles non désacidifiées Expired - Lifetime EP1308498B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10154365 2001-11-06
DE10154365A DE10154365A1 (de) 2001-11-06 2001-11-06 Verfahren zur Herstellung von Fettsäureestern aus nicht entsäuerten Fetten und Ölen

Publications (2)

Publication Number Publication Date
EP1308498A1 true EP1308498A1 (fr) 2003-05-07
EP1308498B1 EP1308498B1 (fr) 2005-07-20

Family

ID=7704720

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02023941A Expired - Lifetime EP1308498B1 (fr) 2001-11-06 2002-10-25 Procédé de production d'esters d'acides gras à partir de graisses et d'huiles non désacidifiées

Country Status (3)

Country Link
EP (1) EP1308498B1 (fr)
AT (1) ATE299925T1 (fr)
DE (2) DE10154365A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007012097A1 (fr) 2005-07-25 2007-02-01 Bdi Biodiesel International Ag Procede de production d'alkylesters d'acide carboxylique

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2383601A (en) * 1943-04-28 1945-08-28 Colgate Palmolive Peet Co Treating fats and fatty oils
US4164506A (en) * 1977-03-17 1979-08-14 Kao Soap Co., Ltd. Process for producing lower alcohol esters of fatty acids
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
EP0200982A1 (fr) * 1985-04-29 1986-11-12 Henkel Kommanditgesellschaft auf Aktien Procédé d'interestérification catalytique de glycérides d'acides gras avec des alcanols inférieurs
EP0249463A2 (fr) * 1986-06-11 1987-12-16 Bio-Energy Technology Ltd. Production d'un biocombustible
JPH04182451A (ja) * 1990-11-17 1992-06-30 Daisan Kasei Kk 高級脂肪酸モノグリセリドの製造方法
US5525126A (en) * 1994-10-31 1996-06-11 Agricultural Utilization Research Institute Process for production of esters for use as a diesel fuel substitute using a non-alkaline catalyst
JP2000144172A (ja) * 1998-11-13 2000-05-26 Sumitomo Chem Co Ltd 脂肪酸エステル類の製造方法および脂肪酸エステル類の用途

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2383601A (en) * 1943-04-28 1945-08-28 Colgate Palmolive Peet Co Treating fats and fatty oils
US4164506A (en) * 1977-03-17 1979-08-14 Kao Soap Co., Ltd. Process for producing lower alcohol esters of fatty acids
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
EP0200982A1 (fr) * 1985-04-29 1986-11-12 Henkel Kommanditgesellschaft auf Aktien Procédé d'interestérification catalytique de glycérides d'acides gras avec des alcanols inférieurs
EP0249463A2 (fr) * 1986-06-11 1987-12-16 Bio-Energy Technology Ltd. Production d'un biocombustible
JPH04182451A (ja) * 1990-11-17 1992-06-30 Daisan Kasei Kk 高級脂肪酸モノグリセリドの製造方法
US5525126A (en) * 1994-10-31 1996-06-11 Agricultural Utilization Research Institute Process for production of esters for use as a diesel fuel substitute using a non-alkaline catalyst
JP2000144172A (ja) * 1998-11-13 2000-05-26 Sumitomo Chem Co Ltd 脂肪酸エステル類の製造方法および脂肪酸エステル類の用途

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 70, no. 23, 9 June 1969, Columbus, Ohio, US; abstract no. 105604y, FAL'KOVICH, M.M. ET AL.: "Comparative effectiveness of alcoholysis catalysts" page 248; column 2; XP002232108 *
LAKOKRAOCH. MATER. IKH PRIMEN., vol. 1, 1969, pages 16 - 18 *
PATENT ABSTRACTS OF JAPAN vol. 016, no. 496 (C - 0995) 14 October 1992 (1992-10-14) *
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 08 6 October 2000 (2000-10-06) *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007012097A1 (fr) 2005-07-25 2007-02-01 Bdi Biodiesel International Ag Procede de production d'alkylesters d'acide carboxylique

Also Published As

Publication number Publication date
DE10154365A1 (de) 2003-05-15
EP1308498B1 (fr) 2005-07-20
DE50203669D1 (de) 2005-08-25
ATE299925T1 (de) 2005-08-15

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