EP0184740B1 - Procédé de préparation d'esters méthyl d'acides gras - Google Patents

Procédé de préparation d'esters méthyl d'acides gras Download PDF

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Publication number
EP0184740B1
EP0184740B1 EP85115217A EP85115217A EP0184740B1 EP 0184740 B1 EP0184740 B1 EP 0184740B1 EP 85115217 A EP85115217 A EP 85115217A EP 85115217 A EP85115217 A EP 85115217A EP 0184740 B1 EP0184740 B1 EP 0184740B1
Authority
EP
European Patent Office
Prior art keywords
methanol
oil phase
glycerol
transesterification
fatty acids
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.)
Expired - Lifetime
Application number
EP85115217A
Other languages
German (de)
English (en)
Other versions
EP0184740A3 (en
EP0184740A2 (fr
Inventor
Herbert Dr. Lepper
Lothar Friesenhagen
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT85115217T priority Critical patent/ATE61332T1/de
Publication of EP0184740A2 publication Critical patent/EP0184740A2/fr
Publication of EP0184740A3 publication Critical patent/EP0184740A3/de
Application granted granted Critical
Publication of EP0184740B1 publication Critical patent/EP0184740B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • 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

Claims (8)

  1. Procédé pour la préparation d'esters méthyliques d'acides gras par transestérification catalytique de graisses et d'huiles naturelles contenant des acides gras libres, dans lequel
    a) dans une pré-estérification, on estérifie les acides gras libres présents dans le produit de départ, en présence de catalyseurs d'estérification acides, à 50 - 120°C et sous des pressions dans la plage de la pression normale à 5 bars, avec du méthanol qui est présent en excès par rapport aux acides gras libres, et on sépare la phase alcoolique contenant le catalyseur et une partie de l'eau de réaction,
    b) on extrait la phase huileuse restante et,
    c) on soumet la phase huileuse traitée à la transestérification sans pression avec du méthanol, catalysée par un alcali, caractérisé en ce que, pour l'élimination de l'eau de réaction résiduelle, on extrait la phase huileuse restante a 40 - 60°C avec un mélange de méthanol et de glycérol, dans lequel le rapport pondéral du glycérol au méthanol va de 1 : 0,25 à 1 : 1,25.
  2. Procédé selon la revendication 1, caractérisé en ce que, dans l'étape a), on utilise de 20 à 50 parties en volume de méthanol pour 100 parties en volume de produit de départ.
  3. Procédé selon les revendications 1 et 2, caractérisé en ce que, dans l'étape a), on opère sous la pression normale.
  4. Procédé selon l'une quelconque des revendications 1 à 3, caractérisé en ce que, dans l'étape a), on utilise en tant que catalyseurs des acides sulfoniques aliphatiques et/ou aromatiques.
  5. Procédé selon l'une quelconque des revendications 1 à 4, caractérisé en ce que dans l'étape a), on abaisse l'indice d'acide de la phase huileuse à des valeurs inférieures à 1.
  6. Procédé selon la revendication 5, caractérisé en ce que le mélange de glycérol et d'alcool utilisé provient de la transestérification sans pression de la phase huileuse, catalysée par un alcali.
  7. Procédé selon l'une quelconque des revendications 1 à 6, caractérisé en ce que, dans l'étape b), on utilise de 10 à 30 parties en volume de mélange de glycérol et de méthanol pour 100 parties en volume de phase huileuse.
  8. Procédé selon l'une quelconque des revendications 1 à 7, caractérisé en ce que l'on effectue l'étape c) à 50 - 100°C.
EP85115217A 1984-12-08 1985-11-30 Procédé de préparation d'esters méthyl d'acides gras Expired - Lifetime EP0184740B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85115217T ATE61332T1 (de) 1984-12-08 1985-11-30 Verfahren zur herstellung von fettsaeuremethylestern.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3444893 1984-12-08
DE19843444893 DE3444893A1 (de) 1984-12-08 1984-12-08 Verfahren zur herstellung von fettsaeuremethylestern

Publications (3)

Publication Number Publication Date
EP0184740A2 EP0184740A2 (fr) 1986-06-18
EP0184740A3 EP0184740A3 (en) 1987-09-09
EP0184740B1 true EP0184740B1 (fr) 1991-03-06

Family

ID=6252300

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85115217A Expired - Lifetime EP0184740B1 (fr) 1984-12-08 1985-11-30 Procédé de préparation d'esters méthyl d'acides gras

Country Status (13)

Country Link
US (1) US4652406A (fr)
EP (1) EP0184740B1 (fr)
JP (1) JPH0662502B2 (fr)
AT (1) ATE61332T1 (fr)
BR (1) BR8506119A (fr)
CA (1) CA1261870A (fr)
DE (2) DE3444893A1 (fr)
ES (1) ES8606242A1 (fr)
GB (1) GB2168701B (fr)
MX (1) MX162267A (fr)
MY (1) MY101291A (fr)
TR (1) TR25060A (fr)
ZA (1) ZA859371B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7828978B2 (en) 2006-01-11 2010-11-09 Doug Geier Simultaneous synthesis and purification of a fatty acid monoester biodiesel fuel
US7951967B2 (en) 2006-04-28 2011-05-31 Sk Chemicals Co., Ltd. Method and apparatus for preparing fatty acid alkyl ester using fatty acid
US8530684B2 (en) 2008-04-01 2013-09-10 Sk Chemicals Co., Ltd. Method for preparing fatty acid alkyl ester using fatty acid
US8895765B2 (en) 2008-11-07 2014-11-25 Sk Chemicals Co., Ltd. Method and apparatus for preparing alkyl ester fatty acid using fatty acid
EP1322588B1 (fr) 2000-10-05 2016-06-29 Bdi-Bioenergy International Ag Procede de production d'esters alkyliques d'acides gras

Families Citing this family (49)

* Cited by examiner, † Cited by third party
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WO1987007632A1 (fr) * 1986-06-11 1987-12-17 Bio-Energy Technology Ltd. Production de carburant biologique
DE3707563A1 (de) * 1987-03-10 1988-09-22 Klaus Dr Ing Scharmer Verfahren zur alkoholyse von fettsaeureglyceriden und vorrichtung zum durchfuehren des verfahrens
SE9001245L (sv) * 1990-04-05 1991-10-06 Carl Johan Lindquist Foerestringsprocess
US6262022B1 (en) 1992-06-25 2001-07-17 Novartis Ag Pharmaceutical compositions containing cyclosporin as the active agent
CA2083346A1 (fr) * 1991-12-13 1993-06-14 Eric G. Lundquist Procede d'esterification par catalyse
DE4209779C1 (fr) * 1992-03-26 1993-07-15 Oelmuehle Leer Connemann Gmbh & Co., 2950 Leer, De
ES2098739T3 (es) 1992-05-13 1997-05-01 Sandoz Ltd Composiciones oftalmicas conteniendo una cyclosporin.
EP0589843B1 (fr) 1992-09-25 2001-11-28 Novartis AG Compositions pharmaceutiques comprenant de la cyclosporine
AT399336B (de) * 1993-07-14 1995-04-25 Martin Mag Dr Mittelbach Verfahren zur herstellung von fettsäurealkylestern
NZ336900A (en) * 1997-01-30 2001-06-29 Novartis Ag Hard gelatine capsules containing pharmaceutical compositions comprising cyclosporin A and being substantially free of any oil
DE19732578C2 (de) * 1997-07-29 2000-08-24 Aventis Res & Tech Gmbh & Co Verwendung von sulfonierten aromatischen Polyetherketon-Kationenaustauschern und sulfonierten Polyphenylensulfid-Kationenaustauschern als Katalysatoren
DE19810440C1 (de) * 1998-03-11 1999-09-23 Dhw Deutsche Hydrierwerke Gmbh Verfahren zur Herstellung von ungesättigten Fettalkoholen aus Lauricölen
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
DE10154365A1 (de) * 2001-11-06 2003-05-15 Cognis Deutschland Gmbh Verfahren zur Herstellung von Fettsäureestern aus nicht entsäuerten Fetten und Ölen
AT504727A1 (de) 2002-04-12 2008-07-15 Energea Umwelttechnologie Gmbh Verfahren und anlage zur veresterung von fettsäuren
US20060042158A1 (en) * 2004-08-26 2006-03-02 Lee John H Fuel products from plant or animal lipids
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
JPWO2007000913A1 (ja) * 2005-06-27 2009-01-22 国立大学法人東京工業大学 高級脂肪酸エステルの製造方法
US7622600B1 (en) * 2006-01-06 2009-11-24 Redland Industries, Inc. System and method for the continuous production of bio-diesel
WO2008016330A2 (fr) * 2006-08-01 2008-02-07 Sie Hendery @ Hendery Bioformule pour remplacer le carburant diesel
US20080289248A1 (en) * 2007-05-23 2008-11-27 Southern Illinois University Carbondale Immobilized esterification catalysts for producing fatty acid alkyl esters
US20100130763A1 (en) * 2006-12-06 2010-05-27 Southern Illinois University Carbondale Processes for the production of fatty acid alkyl esters
US8288573B2 (en) 2006-12-15 2012-10-16 China Petroleum & Chemical Corporation Process for preparing a bio-diesel
US8500828B2 (en) 2006-12-15 2013-08-06 China Petroleum & Chemical Corporation Process for preparing a bio-diesel
JP2008260819A (ja) * 2007-04-11 2008-10-30 National Institute Of Advanced Industrial & Technology バイオディーゼル燃料の製造方法
US20080282606A1 (en) * 2007-04-16 2008-11-20 Plaza John P System and process for producing biodiesel
US20100242346A1 (en) * 2007-09-19 2010-09-30 Best Energies, Inc Processes for the esterification of free fatty acids and the production of biodiesel
US20090187035A1 (en) * 2008-01-22 2009-07-23 Cargill, Incorporated Process for production of fatty acid alkyl esters
US20090247785A1 (en) * 2008-03-31 2009-10-01 The University Of Connecticut Methods and systems for pretreatment of an oil stream
FR2929621A1 (fr) * 2008-04-08 2009-10-09 Arkema France Utilisation d'acide methane sulfonique pour l'esterification d'acides gras
US8742150B2 (en) * 2008-05-14 2014-06-03 Council Of Scientific & Industrial Research Castor oil fatty acid based estolide esters and their derivatives as potential lubricant base stocks
WO2009139884A1 (fr) * 2008-05-14 2009-11-19 Ethox Chemicals, Llc Beurres naturels reconstitués par transestérification avec de la glycérine et leurs utilisations dans des applications cosmétiques
EP2358851B2 (fr) † 2008-11-17 2018-01-10 Basf Se Utilisation de l'acide méthanesulfonique pour la fabrication d'esters d'acide gras
WO2010077685A1 (fr) 2008-12-08 2010-07-08 Onestep Llc Transestérification en une étape de matière première utilisant un catalyseur gazeux
ES2749879T3 (es) 2009-06-26 2020-03-24 China Petroleum & Chem Corp Composición de diésel y proceso para mejorar la estabilidad a la oxidación de biodiésel
WO2011008058A2 (fr) 2009-07-17 2011-01-20 한국과학기술원 Procédé de fabrication d'ester alkyliques d'acides gras à l'aide de microorganismes ayant une aptitude à la production d'huile
MY151440A (en) * 2009-10-29 2014-05-30 Malaysian Palm Oil Board Mpob A method of converting free fatty acid (ffa) from oil to methyl ester
AT510636B1 (de) 2010-10-28 2016-11-15 Wimmer Theodor Verfahren zur herstellung von fettsäureestern niederer alkohole
CN102851122A (zh) * 2011-06-30 2013-01-02 中国石油化工股份有限公司 一种制备脂肪酸酯的方法
CN103013678B (zh) * 2011-09-20 2014-12-31 中国石油化工股份有限公司 降低生物柴油粗产品酸值的方法以及生物柴油的制备方法
KR102327852B1 (ko) 2013-07-22 2021-11-18 에스케이에코프라임 주식회사 지방을 이용한 지방산알킬에스테르의 제조방법
US9328054B1 (en) 2013-09-27 2016-05-03 Travis Danner Method of alcoholisis of fatty acids and fatty acid gyicerides
EP3114196A1 (fr) * 2014-03-04 2017-01-11 Basf Se Procédé de démucilagination et d'estérification d'une huile
ES2585706B1 (es) * 2016-04-21 2017-08-14 Soluciones Industriales Extremeñas Sll Procedimiento mejorado para el refino y esterificación continua de cualquier material graso de origen vegetal o animal, especialmente diseñado para subproductos animales de categoría 1 y 2
ES2660207B8 (es) * 2016-09-21 2019-01-10 Bio Oils Huelva S L Procedimiento de alta eficacia para la producción de alquil-ésteres de ácidos grasos mediante catálisis ácida y procedimiento de tratamiento
US10780433B2 (en) * 2016-11-25 2020-09-22 Arkema France Acid composition for processing fatty acids
FR3059328B1 (fr) * 2016-11-25 2018-11-16 Arkema France Composition acide pour le traitement d'acides gras
CN108977281A (zh) * 2018-07-05 2018-12-11 浙江恒翔化工有限公司 一种利用高酸价劣质油脂制备甲酯的方法
ES2926282T3 (es) * 2018-10-10 2022-10-25 Basf Se Método de producción de biodiésel

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US2383599A (en) * 1942-10-17 1945-08-28 Colgate Palmolive Peet Co Treating fatty glycerides
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DE3319590A1 (de) * 1983-05-30 1984-12-06 Henkel KGaA, 4000 Düsseldorf Verfahren zur herstellung von fettsaeureestern kurzkettiger aliphatischer alkohole aus freie fettsaeuren enthaltenden fetten und/oder oelen

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1322588B1 (fr) 2000-10-05 2016-06-29 Bdi-Bioenergy International Ag Procede de production d'esters alkyliques d'acides gras
US7828978B2 (en) 2006-01-11 2010-11-09 Doug Geier Simultaneous synthesis and purification of a fatty acid monoester biodiesel fuel
US7951967B2 (en) 2006-04-28 2011-05-31 Sk Chemicals Co., Ltd. Method and apparatus for preparing fatty acid alkyl ester using fatty acid
US8530684B2 (en) 2008-04-01 2013-09-10 Sk Chemicals Co., Ltd. Method for preparing fatty acid alkyl ester using fatty acid
US8895765B2 (en) 2008-11-07 2014-11-25 Sk Chemicals Co., Ltd. Method and apparatus for preparing alkyl ester fatty acid using fatty acid

Also Published As

Publication number Publication date
JPS61140544A (ja) 1986-06-27
TR25060A (tr) 1992-09-22
GB2168701A (en) 1986-06-25
EP0184740A3 (en) 1987-09-09
US4652406A (en) 1987-03-24
GB2168701B (en) 1988-11-30
DE3444893A1 (de) 1986-06-12
JPH0662502B2 (ja) 1994-08-17
ES549666A0 (es) 1986-04-16
ES8606242A1 (es) 1986-04-16
ATE61332T1 (de) 1991-03-15
DE3582022D1 (de) 1991-04-11
MY101291A (en) 1991-09-05
EP0184740A2 (fr) 1986-06-18
GB8528953D0 (en) 1986-01-02
ZA859371B (en) 1986-07-30
MX162267A (es) 1991-04-19
BR8506119A (pt) 1986-08-26
CA1261870A (fr) 1989-09-26

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