WO1996010643A1 - Procede de transesterification de graisse ou d'huile - Google Patents

Procede de transesterification de graisse ou d'huile Download PDF

Info

Publication number
WO1996010643A1
WO1996010643A1 PCT/JP1995/001969 JP9501969W WO9610643A1 WO 1996010643 A1 WO1996010643 A1 WO 1996010643A1 JP 9501969 W JP9501969 W JP 9501969W WO 9610643 A1 WO9610643 A1 WO 9610643A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
oil
ester
fat
fats
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.)
Ceased
Application number
PCT/JP1995/001969
Other languages
English (en)
Japanese (ja)
Inventor
Koutaro Yamaguchi
Sadayuki Hukazawa
Tadahisa Shimoda
Tugio Izumi
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.)
Fuji Oil Co Ltd (fka Fuji Oil Holdings Inc)
Original Assignee
Fuji Oil Co Ltd
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 Fuji Oil Co Ltd filed Critical Fuji Oil Co Ltd
Priority to JP51160896A priority Critical patent/JP4335306B2/ja
Publication of WO1996010643A1 publication Critical patent/WO1996010643A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
    • 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
    • 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
    • C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids

Definitions

  • the present invention relates to a method for transesterifying fats and oils.
  • fatty acid esters Enzymatic transesterification of fats and oils with fatty acids or their lower alcohol esters (hereinafter referred to as “fatty acid esters, etc.”) to convert tridaliceride by fiJi: to increase the portability of specific triglyceride molecular species
  • fatty acid esters etc.
  • This reaction is an equilibrium reaction, when the target target is high, a large amount of expensive raw material fatty acid esters and the like must be used, and the subsequent fats and oils must be separated by solvent separation or other means to achieve the target target. Has been done.
  • a multistage ester exchange reaction can be considered, but sufficient efficiency cannot be obtained even if the number of stages is increased as it is.
  • the migration of triglycerides and diglycerides that occur during the distillation operation causes isomerization, and undesired by-products are formed during the next reaction.
  • the present inventors have revised the conventional distillation method in which all fatty acid esters and the like are distilled off in a multi-stage transesterification, and the fatty acids liberated from triglycerides by the reaction were revised. If the boiling point of the ester etc. is lower than the boiling point of the starting fatty acid ester etc. to be introduced into the triglyceride, the fatty acid ester etc.
  • the present invention relates to a method of converting fats and oils into fatty acids or lower alcohol esters thereof. And a step of transesterifying as a catalyst with an enzyme, and a distillation step of removing fatty acids or lower alcohol esters thereof, in a multi-stage process. ⁇ This is a method of exchanging sleeve fat by using alcohol as a threat to selectively remain.
  • the types of raw material fats and oils and raw material fatty acid esters are subject to certain restrictions. That is, a combination of raw materials must be selected so that fatty acid esters and the like liberated from the raw material oil can be selectively removed as much as possible without removing the raw material fatty acid ester and the like in the distillation step. Therefore, in general, it is necessary to select such that the boiling point of the fatty acid or its ester released from the triglyceride by ⁇ is lower than the boiling point of the raw material fatty acid ester to be introduced into the triglyceride.
  • fats and oils include sunflower oil, sunflower oil, sunflower oil, safflower oil, hiolectus flower oil, ⁇ : oil, rapeseed oil, olive oil, palm oil, monkey fat, shea butter, coconut oil, and palm kernel.
  • One or more mixed oils selected from vegetable oils such as oil, animal oils such as fish oil, beef tallow, lard, and synthetic glycerides such as MCT and trilaurin, and palmitic acid, oleic acid as fatty acid esters, etc. Examples thereof include fatty acids having 12 to 24 carbon atoms such as behenic acid and esters of lower alcohols such as methyl or ethyl ester thereof.
  • a transesterification reaction is carried out using the above-mentioned raw materials and using an enzyme as a catalyst.
  • an enzyme as a catalyst.
  • the ester exchange method a known method can be adopted. That is, an enzyme or a cell having transesterification activity such as ribose is converted by a known method.
  • the immobilized enzyme preparation can be used as a catalyst.
  • the reaction solution is distilled by a known method so as to separate fatty acid esters and the like from fats and oils.
  • raw fats and oils and raw fatty acid esters and the like are selectively retained in the steaming step before the final stage.
  • the distillation conditions are as follows. Specifically, the distillation is set so that the fatty acids or the esters thereof released from the raw material triglycerides are kept as much as possible, and that only the raw material fats and oils and the raw material fatty acid esters remain substantially selectively and in large amounts. Is good.
  • This temperature is lower than the temperature at which all fatty acid esters and the like are distilled, especially at 210, and preferably the following temperature. This allows the removal of undesirable by-products such as high melting point components due to migration of triglycerides and diglycerides. Generation is suppressed. In addition, since the heat history becomes small, deterioration of color tone and deterioration of oxidation deterioration stability can be suppressed. These effects become clearer as the length of fatty acids such as fatty acid esters to be introduced is longer, and is most remarkable when the length is 22 or more (22 to 24).
  • Distillation is completed when most of the fatty acid ester and the like released from the triglyceride are distilled off.After the distillation, the liquid is left as it is, or if necessary, a raw material fatty acid ester or the like is added thereto and brought to a temperature suitable for the reaction. To conduct the next step of ester exchange reaction and distillation. If a higher port triglyceride is desired, the number of stages can be increased as needed (further transesterification to distillation is repeated).
  • the reaction efficiency of the raw material fatty acid ester and the like can be increased, and the target triglyceride can be efficiently filtered.
  • the present invention does not require an additional step of separating fats and oils such as solvent separation, and thus can be said to be a convenient method from the viewpoint of safety. Examples and comparative examples
  • reaction substrate was prepared.
  • the column was filled with 90 g of the above lipase agent, and the reaction substrate was passed through at 50 gZhr, 53, and the reaction solution was collected to obtain the first-stage reaction solution. Hold in a distillation flask under 2T0RR vacuum at 206 to selectively remove the forehead (51.4 parts) until substantially no ethyl oleate remains.
  • Table 1 shows the fatty acid composition of the ester before distillation, the distillate, and the ester remaining in the flask.
  • Example 1 50 parts of trilaurin (98% purity, manufactured by Sigma) and 50 parts of stearic acid were mixed, and the same procedure as in Example 1 was performed.
  • the column temperature was set to 65 using Lipozyme (enzyme manufactured by Novo)
  • the column was filled with 5 g of the lipase agent, and the substrate was passed at 3 gZhr.
  • the mixture was held in a distillation flask at 150 under 2 TORR vacuum to remove lauric acid.
  • Example 2 After distilling the first-stage reaction solution of Example 1 at 255 to completely remove the ethyl ester, 72 parts of behenic acid ethyl ester was added to 28 parts of the triglyceride remaining in the flask, and the mixture was treated with clay. The solution was passed to obtain a second-stage reaction solution, which was held at 255 under 2T0RR vacuum to completely remove the ester component.
  • the BOB content in this reaction product was 62%, but the BBB content was as high as 5.1%, making it difficult to use as a tempering accelerator unless the high melting point component was separated and removed. . In addition, it was considerably colored and was not preferable (color tone-5.0 x 50).
  • the first-stage distillation was carried out at 235, and the same method as in Example 2 was carried out except that 70 parts of oleic acid ethyl ester newly added to the S solution were used.
  • the Example requires less amount of fatty acid esters and the like than the Comparative Example, suppresses the generation of by-products, and improves the commercial portability of the target triglyceride as compared with the ordinary multistage transesterification method. And was able to do it efficiently.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Fats And Perfumes (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Procédé de transestérification de graisse ou d'huile permettant de modifier cette dernière et de préparer efficacement des triglycérides cibles en grandes concentrations. Le procédé consiste à transestérifier une graisse ou une huile à l'aide d'un acide gras ou d'un ester d'alcool inférieur de ce dernier en présence d'un catalyseur enzymatique et à extraire par distillation l'acide ou l'ester du mélange de réaction, ces deux étapes étant répétées dans plusieurs phases. Ce procédé se caractérise en ce que l'on n'enlève pas du mélange de réaction la graisse ou l'huile et l'acide gras de la charge de départ ou l'ester de celui-ci dans les étapes de distillation précédant la phase ultime. Ce procédé permet de réduire le volume d'acide gras ou d'ester à utiliser et d'inhiber la formation de sous-produits, et de produire lesdits triglycérides cibles en grandes concentrations plus efficacement que les procédés de transestérification à phases multiples classiques.
PCT/JP1995/001969 1994-09-30 1995-09-28 Procede de transesterification de graisse ou d'huile Ceased WO1996010643A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP51160896A JP4335306B2 (ja) 1994-09-30 1995-09-28 油脂のエステル交換方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP23823494 1994-09-30
JP6/238234 1994-09-30

Publications (1)

Publication Number Publication Date
WO1996010643A1 true WO1996010643A1 (fr) 1996-04-11

Family

ID=17027146

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1995/001969 Ceased WO1996010643A1 (fr) 1994-09-30 1995-09-28 Procede de transesterification de graisse ou d'huile

Country Status (2)

Country Link
JP (1) JP4335306B2 (fr)
WO (1) WO1996010643A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002105484A (ja) * 2000-09-29 2002-04-10 Fuji Oil Co Ltd 油脂の製造方法
US6617141B1 (en) * 1997-12-08 2003-09-09 Council Of Scientific & Industrial Research Enzymatic process for preparing reduced-calorie fats containing behenic acid
WO2003080851A1 (fr) * 2002-03-21 2003-10-02 Fuji Oil Company, Limited Procede de transesterification de graisses ou analogues
WO2009031680A1 (fr) 2007-09-07 2009-03-12 The Nisshin Oillio Group, Ltd. Procédé de séparation de triglycéride 1,3-disaturé-2-insaturé
WO2009031679A1 (fr) 2007-09-07 2009-03-12 The Nisshin Oillio Group, Ltd. Procédé de production de beurre dur
JP2013533346A (ja) * 2010-06-30 2013-08-22 ロダース・クロックラーン・ビー・ブイ 植物油の処理

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011132813A1 (fr) * 2010-04-22 2011-10-27 씨제이제일제당(주) Procédé de fractionnement à sec pour une composition d'huiles et de graisses transestérifiées
KR101314682B1 (ko) * 2010-04-22 2013-10-07 씨제이제일제당 (주) 카카오 버터 유사 하드버터의 제조 방법

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6261589A (ja) * 1985-09-10 1987-03-18 Fuji Oil Co Ltd グリセリド油脂の加工法
JPH01137988A (ja) * 1987-08-31 1989-05-30 Japanese Res & Dev Assoc Bio Reactor Syst Food Ind エステル交換脂の製造法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6261589A (ja) * 1985-09-10 1987-03-18 Fuji Oil Co Ltd グリセリド油脂の加工法
JPH01137988A (ja) * 1987-08-31 1989-05-30 Japanese Res & Dev Assoc Bio Reactor Syst Food Ind エステル交換脂の製造法

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6617141B1 (en) * 1997-12-08 2003-09-09 Council Of Scientific & Industrial Research Enzymatic process for preparing reduced-calorie fats containing behenic acid
JP2002105484A (ja) * 2000-09-29 2002-04-10 Fuji Oil Co Ltd 油脂の製造方法
WO2003080851A1 (fr) * 2002-03-21 2003-10-02 Fuji Oil Company, Limited Procede de transesterification de graisses ou analogues
WO2009031680A1 (fr) 2007-09-07 2009-03-12 The Nisshin Oillio Group, Ltd. Procédé de séparation de triglycéride 1,3-disaturé-2-insaturé
WO2009031679A1 (fr) 2007-09-07 2009-03-12 The Nisshin Oillio Group, Ltd. Procédé de production de beurre dur
EP2388306A1 (fr) 2007-09-07 2011-11-23 The Nisshin OilliO Group, Ltd. Procédé de fractionnement du triglycéride disaturé en 1,3 et insaturé en 2
EP2388307A1 (fr) 2007-09-07 2011-11-23 The Nisshin OilliO Group, Ltd. Procédé de fractionnement du triglycéride disaturé en 1,3 et insaturé en 2
EP2399977A1 (fr) 2007-09-07 2011-12-28 The Nisshin OilliO Group, Ltd. Méthode de fracionnement pour triglycéride 1,3-disaturé-2-insaturé
US8389754B2 (en) 2007-09-07 2013-03-05 The Nisshin Oillio Group, Ltd. Fractionation method of 1,3-disaturated-2-unsaturated triglyceride
US8980346B2 (en) 2007-09-07 2015-03-17 The Nisshin Oillio Group, Ltd. Process for preparing hard butter
JP2013533346A (ja) * 2010-06-30 2013-08-22 ロダース・クロックラーン・ビー・ブイ 植物油の処理
US9161553B2 (en) 2010-06-30 2015-10-20 Loders Croklaan B.V. Processing of vegetable oils

Also Published As

Publication number Publication date
JP4335306B2 (ja) 2009-09-30

Similar Documents

Publication Publication Date Title
JP2761293B2 (ja) ヒト乳脂の代替物の製造方法
EP2602308B1 (fr) Estérification catalysée par lipase d'huile marine
CN1098921C (zh) 用于生产甘油二酯的方法
US4960544A (en) Fractionation of fat blends
US6090598A (en) Enzymatic process for interesterification of fats and oils using distillation
JP2971962B2 (ja) ジグリセリドに富む油脂の脱臭工程における不均化反応を抑制する方法
JP5216277B2 (ja) 食用油脂の製造方法
CN101258230A (zh) 用于制备二油酰棕榈酰甘油酯的方法
CN106413414A (zh) 脂肪酸组合物及其应用
WO2019054256A1 (fr) Procédé pour la production de matière grasse
JPH0349319B2 (fr)
JPH0542260B2 (fr)
WO1996010643A1 (fr) Procede de transesterification de graisse ou d'huile
RU2635696C2 (ru) 1,3-селективная переэтерификация
JPWO1996010643A1 (ja) 油脂のエステル交換方法
JP3847445B2 (ja) ジグリセリドの製造法
JP2687337B2 (ja) 液体油の製造法
CN101287819B (zh) 甘油三酯方法
JPH0687787B2 (ja) サラダ油の製造方法
CN111787807A (zh) 2位富含棕榈酸的油脂组合物的制造方法
JPH03109495A (ja) 改質ラウリン脂肪組成物又は乳脂肪組成物及び、脂肪及びトリグリセリド油をトランスエステル交換する方法
JP4168933B2 (ja) 加工グリセリド油脂の製造法
JP3932788B2 (ja) 油脂類のエステル交換方法
EP0519542A1 (fr) Procédé combiné de fractionnement, de raffinage et d'interestérification
CN1277797C (zh) 脂肪酸类的制造方法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase