EP0184740A3 - Process for the preparation of methyl esters of fatty acids - Google Patents

Process for the preparation of methyl esters of fatty acids Download PDF

Info

Publication number
EP0184740A3
EP0184740A3 EP85115217A EP85115217A EP0184740A3 EP 0184740 A3 EP0184740 A3 EP 0184740A3 EP 85115217 A EP85115217 A EP 85115217A EP 85115217 A EP85115217 A EP 85115217A EP 0184740 A3 EP0184740 A3 EP 0184740A3
Authority
EP
European Patent Office
Prior art keywords
fatty acids
methanol
oil phase
alkanol
reaction
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
EP85115217A
Other languages
German (de)
Other versions
EP0184740A2 (en
EP0184740B1 (en
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/en
Publication of EP0184740A2 publication Critical patent/EP0184740A2/en
Publication of EP0184740A3 publication Critical patent/EP0184740A3/en
Application granted granted Critical
Publication of EP0184740B1 publication Critical patent/EP0184740B1/en
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

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Fatty acid alkyl esters are produced by catalytic transesterification of natural fats and oils containing free fatty acids. In a preliminary esterifying step, the free fatty acids present are reacted with a C1-C4 alkanol (e.g., methanol) in the presence of an acidic esterification catalyst, at a temperature of about 50 DEG to 120 DEG C. and at substantially atmospheric pressure. The resulting reaction mixture is allowed to separate into two phases: (1) an alcohol phase containing the acidic esterification catalyst and part of the water of reaction and (2) an oil phase. These phases separately recovered. The oil phase is then extracted with an immiscible extractant, preferably comprising a mixture of glycerol and methanol, to remove residual water of reaction. In the final step the extracted oil phase is transesterified with a C1-C4 alkanol, e.g. methanol, in the presence of an aklali catalyst and at substantially atmospheric pressure.
EP85115217A 1984-12-08 1985-11-30 Process for the preparation of methyl esters of fatty acids Expired - Lifetime EP0184740B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85115217T ATE61332T1 (en) 1984-12-08 1985-11-30 PROCESS FOR THE PREPARATION OF FATTY ACID METHYL ESTERS.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3444893 1984-12-08
DE19843444893 DE3444893A1 (en) 1984-12-08 1984-12-08 METHOD FOR PRODUCING FATTY ACID METHYL ESTERS

Publications (3)

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

Family

ID=6252300

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85115217A Expired - Lifetime EP0184740B1 (en) 1984-12-08 1985-11-30 Process for the preparation of methyl esters of fatty acids

Country Status (13)

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

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987007632A1 (en) * 1986-06-11 1987-12-17 Bio-Energy Technology Ltd. Bio-fuel production
DE3707563A1 (en) * 1987-03-10 1988-09-22 Klaus Dr Ing Scharmer Process for the alcoholysis of fatty acid glycerides and device for carrying out the process
SE9001245L (en) * 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 (en) * 1991-12-13 1993-06-14 Eric G. Lundquist A catalyzed esterification process
DE4209779C1 (en) * 1992-03-26 1993-07-15 Oelmuehle Leer Connemann Gmbh & Co., 2950 Leer, De
DK0642332T3 (en) 1992-05-13 1997-06-16 Sandoz Ltd Ophthalmic preparations containing cyclosporin
EP1142568A1 (en) 1992-09-25 2001-10-10 Novartis AG Pharmaceutical compositions containing cyclosporins
AT399336B (en) * 1993-07-14 1995-04-25 Martin Mag Dr Mittelbach METHOD FOR PRODUCING FATTY ACID ALKYL ESTERS
BR9807528A (en) 1997-01-30 2000-03-14 Novartis Ag Oil-free pharmaceutical compositions containing cyclosporine a
DE19732578C2 (en) * 1997-07-29 2000-08-24 Aventis Res & Tech Gmbh & Co Use of sulfonated aromatic polyether ketone cation exchangers and sulfonated polyphenylene sulfide cation exchangers as catalysts
DE19810440C1 (en) * 1998-03-11 1999-09-23 Dhw Deutsche Hydrierwerke Gmbh Process for the production of unsaturated fatty alcohols from lauric oils
ATA16992000A (en) 2000-10-05 2001-12-15 Michael Dr Koncar METHOD FOR PRODUCING FATTY ACID 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
DE10154365A1 (en) * 2001-11-06 2003-05-15 Cognis Deutschland Gmbh Process for the production of fatty acid esters from non-deacidified fats and oils
AT504727A1 (en) * 2002-04-12 2008-07-15 Energea Umwelttechnologie Gmbh METHOD AND APPARATUS FOR THE ESTABLISHMENT OF FATTY ACIDS
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
EP1897865B1 (en) * 2005-06-27 2011-06-08 Tokyo Institute Of Technology Processes for producing higher fatty acid esters
US7622600B1 (en) * 2006-01-06 2009-11-24 Redland Industries, Inc. System and method for the continuous production of bio-diesel
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
WO2008016330A2 (en) * 2006-08-01 2008-02-07 Sie Hendery @ Hendery Bio formula to substitute diesel fuel
US20100130763A1 (en) * 2006-12-06 2010-05-27 Southern Illinois University Carbondale Processes for the production of fatty acid alkyl esters
US20080289248A1 (en) * 2007-05-23 2008-11-27 Southern Illinois University Carbondale Immobilized esterification catalysts for producing fatty acid alkyl esters
WO2008071040A1 (en) 2006-12-15 2008-06-19 China Petroleum & Chemical Corporation A procss for preparing biodiesel
US8500828B2 (en) 2006-12-15 2013-08-06 China Petroleum & Chemical Corporation Process for preparing a bio-diesel
JP2008260819A (en) * 2007-04-11 2008-10-30 National Institute Of Advanced Industrial & Technology Method for producing bio-diesel fuel
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
JP5380523B2 (en) 2008-04-01 2014-01-08 エスケー ケミカルズ カンパニー リミテッド Method for producing fatty acid alkyl ester using fatty acid
FR2929621A1 (en) * 2008-04-08 2009-10-09 Arkema France Esterifying free fatty acid, useful to prepare bio-diesel, comprises providing a fatty substance comprising free fatty acid, adding alcohol and methane sulfonic acid, conducting esterification reaction, and recovering the fatty substance
WO2009139884A1 (en) * 2008-05-14 2009-11-19 Ethox Chemicals, Llc Natural butters reconstituted by transesterification with glycerin and its use in consmetics applications
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
KR101554607B1 (en) 2008-11-07 2015-09-22 에스케이케미칼주식회사 Method and apparatus for preparing fatty acid alkyl ester using fatty acid
ES2457097T5 (en) † 2008-11-17 2018-04-16 Basf Se Use of methanesulfonic acid for the preparation of fatty acid esters
MX2011006179A (en) 2008-12-08 2014-04-25 Initio Fuels Llc Single step transesterification of feedstock using a gaseous catalyst.
WO2010148652A1 (en) 2009-06-26 2010-12-29 中国石油化工股份有限公司 Diesel composition and process for improving oxidation stability of biodiesel
CN102575272B (en) 2009-07-17 2014-12-10 韩国科学技术院 Method for producing fatty acid alkyl esters using microorganisms having oil-producing ability
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 (en) 2010-10-28 2016-11-15 Wimmer Theodor PROCESS FOR PREPARING FATTY ACID PRESENTS OF LOW ALCOHOLS
CN102851122A (en) * 2011-06-30 2013-01-02 中国石油化工股份有限公司 Method for preparation of fatty acid ester
CN103013678B (en) * 2011-09-20 2014-12-31 中国石油化工股份有限公司 Method for reducing biodiesel crude product acid value, and biodiesel preparation method
KR102327852B1 (en) 2013-07-22 2021-11-18 에스케이에코프라임 주식회사 Method for preparing fatty acid alkyl ester using fat
US9328054B1 (en) 2013-09-27 2016-05-03 Travis Danner Method of alcoholisis of fatty acids and fatty acid gyicerides
AU2015227367A1 (en) * 2014-03-04 2016-09-22 Basf Se Method for degumming and esterification of an oil
ES2585706B1 (en) * 2016-04-21 2017-08-14 Soluciones Industriales Extremeñas Sll Improved procedure for the refining and continuous esterification of any fatty material of vegetable or animal origin, specially designed for animal by-products of category 1 and 2
ES2660207B8 (en) * 2016-09-21 2019-01-10 Bio Oils Huelva S L High efficiency process for the production of alkyl esters of fatty acids by acid catalysis and treatment procedure
FR3059328B1 (en) * 2016-11-25 2018-11-16 Arkema France ACIDIC COMPOSITION FOR THE TREATMENT OF FATTY ACIDS
MY192473A (en) 2016-11-25 2022-08-23 Arkema France Acid composition for processing fatty acids
CN108977281A (en) * 2018-07-05 2018-12-11 浙江恒翔化工有限公司 A method of methyl esters is prepared using high acid value poor oil rouge
US11591545B2 (en) * 2018-10-10 2023-02-28 Basf Se Method of producing biodiesel
EP4132900A1 (en) * 2020-04-07 2023-02-15 Basf Se Energy efficient biodiesel production from natural or industrial waste oil

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2383599A (en) * 1942-10-17 1945-08-28 Colgate Palmolive Peet Co Treating fatty glycerides
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 (en) * 1983-05-30 1984-12-05 Henkel Kommanditgesellschaft auf Aktien Process for the preparation of fatty-acid esters of short chain aliphatic alcohols from free fatty-acid-containing fats and/or oils

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US22751A (en) * 1859-01-25 Ball furniture-caster
US2360844A (en) * 1941-11-26 1944-10-24 Du Pont Preparation of detergents
US2486444A (en) * 1947-07-08 1949-11-01 Baker Castor Oil Co Process of producing esters

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2383599A (en) * 1942-10-17 1945-08-28 Colgate Palmolive Peet Co Treating fatty glycerides
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 (en) * 1983-05-30 1984-12-05 Henkel Kommanditgesellschaft auf Aktien Process for the preparation of fatty-acid esters of short chain aliphatic alcohols from free fatty-acid-containing fats and/or oils

Also Published As

Publication number Publication date
ES549666A0 (en) 1986-04-16
GB8528953D0 (en) 1986-01-02
DE3582022D1 (en) 1991-04-11
TR25060A (en) 1992-09-22
GB2168701A (en) 1986-06-25
DE3444893A1 (en) 1986-06-12
ATE61332T1 (en) 1991-03-15
CA1261870A (en) 1989-09-26
JPS61140544A (en) 1986-06-27
MX162267A (en) 1991-04-19
ZA859371B (en) 1986-07-30
EP0184740A2 (en) 1986-06-18
ES8606242A1 (en) 1986-04-16
US4652406A (en) 1987-03-24
EP0184740B1 (en) 1991-03-06
MY101291A (en) 1991-09-05
GB2168701B (en) 1988-11-30
BR8506119A (en) 1986-08-26
JPH0662502B2 (en) 1994-08-17

Similar Documents

Publication Publication Date Title
GB2168701B (en) A process for the production of fatty acid methyl esters
CA2143441A1 (en) Recovery of tocopherol and sterol
FI116847B (en) Process for the preparation of fatty acid alkyl esters
Bondioli The preparation of fatty acid esters by means of catalytic reactions
CA2264558A1 (en) Method for preparing fatty acid esters
ES543917A0 (en) PROCEDURE FOR PREPARING ESTERS OF FATTY ACIDS FROM PRIMARY AND SECONDARY SHORT-CHAIN ALCOHOLS
CZ111694A3 (en) Process for preparing esters of fatty acids with monovalent alcohols having a short chain
JP2003507495A (en) Single-phase process for producing fatty acid methyl esters from a mixture of triglycerides and fatty acids
CZ279421B6 (en) Process for preparing esters of fatty acids of lower alcohols
AU2004267023A1 (en) Method of making alkyl esters using glycerin
GB2153351B (en) A process for the production of mixtures containing c6-c10-fatty acids
EP0320043A3 (en) Process for the synthesis of polyol fatty acid esters
SU131352A1 (en) The use of metallic sodium as a catalyst

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

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH DE FR IT LI NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE FR IT LI NL SE

17P Request for examination filed

Effective date: 19870925

17Q First examination report despatched

Effective date: 19890329

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE FR IT LI NL SE

REF Corresponds to:

Ref document number: 61332

Country of ref document: AT

Date of ref document: 19910315

Kind code of ref document: T

ET Fr: translation filed
REF Corresponds to:

Ref document number: 3582022

Country of ref document: DE

Date of ref document: 19910411

ITF It: translation for a ep patent filed

Owner name: STUDIO JAUMANN

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

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

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19931020

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19931026

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 19931103

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19931110

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19931117

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19931130

Year of fee payment: 9

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19940105

Year of fee payment: 9

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Effective date: 19941130

Ref country code: CH

Effective date: 19941130

Ref country code: BE

Effective date: 19941130

Ref country code: AT

Effective date: 19941130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19941201

EAL Se: european patent in force in sweden

Ref document number: 85115217.3

BERE Be: lapsed

Owner name: HENKEL K.G.A.A.

Effective date: 19941130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19950601

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19950731

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19950801

EUG Se: european patent has lapsed

Ref document number: 85115217.3

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST