WO1991014784A1 - A process for increasing the amount of triglyceride of a fat or oil - Google Patents

A process for increasing the amount of triglyceride of a fat or oil Download PDF

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Publication number
WO1991014784A1
WO1991014784A1 PCT/DK1991/000083 DK9100083W WO9114784A1 WO 1991014784 A1 WO1991014784 A1 WO 1991014784A1 DK 9100083 W DK9100083 W DK 9100083W WO 9114784 A1 WO9114784 A1 WO 9114784A1
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Prior art keywords
lipase
immobilized
triglyceride
process according
oil
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PCT/DK1991/000083
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French (fr)
Inventor
Hanne Svanholm
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Novo Nordisk A/S
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Publication date
Priority claimed from DK75890A external-priority patent/DK75890D0/en
Priority claimed from DK226490A external-priority patent/DK226490D0/en
Application filed by Novo Nordisk A/S filed Critical Novo Nordisk A/S
Publication of WO1991014784A1 publication Critical patent/WO1991014784A1/en

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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • 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
    • C11C3/10—Ester interchange
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
    • C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
    • C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
    • C12N11/082—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
    • C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
    • C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
    • C12N11/082—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C12N11/087—Acrylic polymers

Definitions

  • a process for increasing the amount of triglyceride of a fat or oil is provided.
  • the invention relates to a process for increasing the amount of triglyceride (TG) of a fat or oil containing free fatty acid (FFA) together with diglyceride (DG) and/or monoglyceride (MG) and/or glycerol in the presence of a lipase.
  • TG triglyceride
  • FFA free fatty acid
  • DG diglyceride
  • MG monoglyceride
  • glycerol glycerol
  • Some commercial fats and oils have a considerable content of diglyceride and fatty acid, e.g. some vegetable oils such as palm oil and rice bran oil. Thus, extracted palm oil typically contains about 5% of free fatty acid and 10% diglycerides. In rice bran oil, the free fatty acid level generally varies from about 2 to 5 %, but commercial oils with 15-40% free fatty acid have been reported.
  • Free fatty acids are relatively easy to remove by refining of the oil, but diglycerides are very difficult to remove even partially. In many applications, the diglycerides cause problems by changing the physical and chemical properties of the oil.
  • TG content of palm oil could be increased from 84 to 95% in 24 hours, at otherwise essentially the same conditions as Kurashige (op.cit.).
  • the invention provides a process for increasing the amount of triglyceride in a fat or oil containing free fatty acid together with diglyceride, monoglyceride and/or glycerol in the presence of a lipase.
  • the lipase is immobilized by adsorption on a particulate, macroporous adsorbent (i.e. non-ionic) resin of the acrylic type.
  • the lipase is positionally non-specific or is derived from Humicola. DETAILED DESCRIPTION OF THE INVENTION
  • the process of the invention serves to convert free fatty acid together with diglyceride, monoglyceride and/or glycerol contained in a fat or oil into triglyceride.
  • This process is applicable to any fat or oil containing these, particularly to fats or oils containing valuable structured lipids, so that acyl migration is undesired.
  • examples are vegetable oils, such as palm oil, olive oil, rice bran oil, palm kernel oil and cottonseed oil. These typically contain free fatty acid in essentially the stoichiometric amount, i.e. as required for full conversion of diglycerides etc. into triglyceride.
  • Another example is upgrading of oils with a high content of free fatty acids that occur as by-products in oil processing. It may be preferred to add glycerol to reach essentially the stoichiometric ratio for the conversion.
  • the process of the invention is also applicable to oil or fat that has been subjected to lipase-catalyzed interesterification in the presence of a small amount of water.
  • the main purpose is conversion of diglyceride to triglyceride.
  • Diglycerides are otherwise difficult to remove. Addition of glycerol is generally not preferred.
  • One aspect of the invention uses a positionally non-specific lipase, i.e. one that reacts with all three acyl groups of a TG molecule.
  • lipases derived from strains of Candida, especially C. antarctica lipase (WO 88/02775, incorporated herein by reference), and lipase from C. rugosa (also known as C. cylindracea). It is preferred to use a lipase preparation containing lipase B, and particularly a preparation containing both lipase A and lipase B of C. antarctica described in said reference. Humicola lipase
  • Preferred Humicola upases are those derived from H. lanuginosa (WO 89/06278) and recombinant Humicola lipase (EP 305,216).
  • the non-specific lipase or Humicola lipase may optionally be immobilized, e.g. by adsorption on a macroporous adsorbent resin as described further below or on a weakly basic anion exchange resin (e.g. as described in EP 140,542) or on an inorganic carrier such as silica.
  • One aspect of the invention uses lipase immobilized by adsorption on a particulate, macroporous adsorbent (i.e. non-ionic) resin.
  • the resin may be of the acrylic type according to WO 89/02916 (incorporated herein by reference) or a hydrophobic resin, especially a polyolefin such as polypropylene, as described in EP 232,933 (AKZO) and EP 322,213 (Unilever).
  • the lipase to be immobilized on this resin may be e.g. a non-specific lipase or Humicola lipase, as described above, or a lipase from Mucor (also termed Rhizomucor), especially M. miehei (R. miehei).
  • Mucor also termed Rhizomucor
  • a suitable water content can be achieved by applying vacuum (e.g. below 500 Pa) during all or part of the reaction time, by aeration with dry, inactive gas (e.g. nitrogen or air), by free evaporation to a dry atmosphere while stirring the reaction mixture, or by use of molecular sieves.
  • vacuum e.g. below 500 Pa
  • inactive gas e.g. nitrogen or air
  • the reaction temperature will generally be in the range 40-70°C, depending on temperature stability of the lipase. Sufficient conversion of FFA with DG, MG and/or glycerol to TG can generally be achieved in less than 36 hours, usually less than 24 hours. Such a short reaction time is preferred in order to reduce acyl migration.
  • Immobilized lipase samples were prepared by the procedure of
  • the acrylic resin used above was Lewatit ® E2001/85 from Bayer, and the polypropylene was Accurel from AKZO.
  • Example 2 Each sample was treated as in Example 1 , using the first- mentioned lipase. Analysis was done by latroscan after removal of free fatty acids and/or methyl esters. The following results were obtained:

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

Abstract

Treatment of a fat or oil containing free fatty acid together with diglyceride and/or monoglyceride and/or glycerol with a positionally non-specific lipase or with lipase derived from Humicola or with lipase immobilized on a macroporous acrylic carrier leads to a much more rapid formation of triglyceride than prior-art process, and the shorter reaction time leads to less acyl migration. Treatment with lipase immobilized on a macroporous acrylic carrier promotes triglyceride formation and retards acyl migration.

Description

A process for increasing the amount of triglyceride of a fat or oil.
TECHNICAL FIELD
The invention relates to a process for increasing the amount of triglyceride (TG) of a fat or oil containing free fatty acid (FFA) together with diglyceride (DG) and/or monoglyceride (MG) and/or glycerol in the presence of a lipase.
BACKGROUND ART
Some commercial fats and oils have a considerable content of diglyceride and fatty acid, e.g. some vegetable oils such as palm oil and rice bran oil. Thus, extracted palm oil typically contains about 5% of free fatty acid and 10% diglycerides. In rice bran oil, the free fatty acid level generally varies from about 2 to 5 %, but commercial oils with 15-40% free fatty acid have been reported.
Similarly, in lipase-catalyzed interesterification of oil, a small amount of water is required to activate the lipase. This water facilitates hydrolysis side reactions, resulting in the formation of some diglycerides and free fatty acids.
Free fatty acids are relatively easy to remove by refining of the oil, but diglycerides are very difficult to remove even partially. In many applications, the diglycerides cause problems by changing the physical and chemical properties of the oil.
Treatment of crude vegetable oil with lipase to convert DG and
FFA into TG, thereby removing the undesired DG and increasing the yield of
TG, is described by J. Kurashige, Proceedings from World Conference on
Biotechnology for the Fats and Oil Industry 1988, 138-141 , S. Bhattacharyya et al., Fat Sci. Technol., 91 (1), 27-31 (1989) and S. Bhattacharyya et al., JAOCS, Vol. 66, No. 10 (Oct. 1989). Water was removed by vacuum in order to promote the reaction. Kurashige, using lipase from Pseudomonas fluorescens immobilized on celite at 60ºC, reported that 3 days was required to increase TG from 87% to 95%. The lipase is known to be positionally specific.
However, it is known that these process conditions cause considerable acyl migration, thereby reducing the oil's content of valuable structured lipids of formula SUS (S=saturated, U=unsaturated). It is the object of the invention to provide an improved process with more rapid increase of TG content and less acyl migration.
STATEMENT OF THE INVENTION
We have found that, surprisingly, treatment of an oil with a suitably chosen lipase leads to a much more rapid formation of TG than the prior-art process. Advantageously, the shorter reaction time leads to less acyl migration. We have found that this improvement can be realized by use of a positionally non-specific lipase or a lipase derived from Humicola or by use of lipase immobilized on a macroporous acrylic carrier. Thus, according to the invention the TG content of palm oil could be increased from 84 to 95% in 24 hours, at otherwise essentially the same conditions as Kurashige (op.cit.).
Accordingly, the invention provides a process for increasing the amount of triglyceride in a fat or oil containing free fatty acid together with diglyceride, monoglyceride and/or glycerol in the presence of a lipase. In one aspect, the lipase is immobilized by adsorption on a particulate, macroporous adsorbent (i.e. non-ionic) resin of the acrylic type. In other aspects, the lipase is positionally non-specific or is derived from Humicola. DETAILED DESCRIPTION OF THE INVENTION
Fat or oil
The process of the invention serves to convert free fatty acid together with diglyceride, monoglyceride and/or glycerol contained in a fat or oil into triglyceride. This process is applicable to any fat or oil containing these, particularly to fats or oils containing valuable structured lipids, so that acyl migration is undesired. Examples are vegetable oils, such as palm oil, olive oil, rice bran oil, palm kernel oil and cottonseed oil. These typically contain free fatty acid in essentially the stoichiometric amount, i.e. as required for full conversion of diglycerides etc. into triglyceride.
Another example is upgrading of oils with a high content of free fatty acids that occur as by-products in oil processing. It may be preferred to add glycerol to reach essentially the stoichiometric ratio for the conversion.
The process of the invention is also applicable to oil or fat that has been subjected to lipase-catalyzed interesterification in the presence of a small amount of water. Here, the main purpose is conversion of diglyceride to triglyceride. Diglycerides are otherwise difficult to remove. Addition of glycerol is generally not preferred.
Non-specific lipase
One aspect of the invention uses a positionally non-specific lipase, i.e. one that reacts with all three acyl groups of a TG molecule. Examples are lipases derived from strains of Candida, especially C. antarctica lipase (WO 88/02775, incorporated herein by reference), and lipase from C. rugosa (also known as C. cylindracea). It is preferred to use a lipase preparation containing lipase B, and particularly a preparation containing both lipase A and lipase B of C. antarctica described in said reference. Humicola lipase
Preferred Humicola upases are those derived from H. lanuginosa (WO 89/06278) and recombinant Humicola lipase (EP 305,216).
The non-specific lipase or Humicola lipase may optionally be immobilized, e.g. by adsorption on a macroporous adsorbent resin as described further below or on a weakly basic anion exchange resin (e.g. as described in EP 140,542) or on an inorganic carrier such as silica.
Immobilization method
One aspect of the invention uses lipase immobilized by adsorption on a particulate, macroporous adsorbent (i.e. non-ionic) resin. The resin may be of the acrylic type according to WO 89/02916 (incorporated herein by reference) or a hydrophobic resin, especially a polyolefin such as polypropylene, as described in EP 232,933 (AKZO) and EP 322,213 (Unilever).
The lipase to be immobilized on this resin may be e.g. a non- specific lipase or Humicola lipase, as described above, or a lipase from Mucor (also termed Rhizomucor), especially M. miehei (R. miehei).
Reaction conditions
In order to shift the reaction equilibrium, the water content in the reaction system should be kept low. On the other hand, a slight amount of water should be present in order to activate the lipase. A suitable water content can be achieved by applying vacuum (e.g. below 500 Pa) during all or part of the reaction time, by aeration with dry, inactive gas (e.g. nitrogen or air), by free evaporation to a dry atmosphere while stirring the reaction mixture, or by use of molecular sieves.
The reaction temperature will generally be in the range 40-70°C, depending on temperature stability of the lipase. Sufficient conversion of FFA with DG, MG and/or glycerol to TG can generally be achieved in less than 36 hours, usually less than 24 hours. Such a short reaction time is preferred in order to reduce acyl migration.
A suitable amount of lipase is generally in the range 1-5 BlU/g of oil (BIU = Batch Interesterification Unit, see WO 89/06278) by use of immobilized lipase, or 50-500 LU/g of oil (LU = Lipase Unit, see WO 88/02775) by use of native (non-immobilized) lipase.
It is preferred to run the process without organic solvent, to avoid costly separation after the process. EXAMPLE 1
Immobilized lipase samples were prepared by the procedure of
Example 1 of WO 89/02916 from the lipases and carriers shown below. Partially purified palm oil (1 ppm Fe, 3.2 ppm P, peroxide value 5.5, p-anisidine value
8.9) was treated with 10% by weight of the immobilized lipase in a rotary evaporator at 60ºC, 5 mbar (500 Pa).
Samples were taken before treatment and after 24 and 48 hours and were analyzed for content of triglyceride (TG), free fatty acid (FFA), diglyceride (DG) and acid value (AV). Results:
Figure imgf000007_0001
The acrylic resin used above was Lewatit® E2001/85 from Bayer, and the polypropylene was Accurel from AKZO.
The above results can be compared with Kurashige (op.cit.) who reported increase from 87% TG to 91% after 24 hours and 93% after 48 hours at similar conditions. It is seen that a faster conversion of DG and FFA into TG is achieved by the use of non-specific lipase (such as that from C. antarctica) or lipase from Humicola. Faster conversion is also obtained by the use of lipase adsorbed on a macroporous, non-ionic (so-called adsorbent) resin.
EXAMPLE 2 Three samples of interesterified oils were prepared by lipase- catalyzed interesterification of the following mixtures:
A. Palm oil mid fraction + methyl stearate (1 :1 w/w), 50% water saturation.
B. Palm oil mid fraction + methyl stearate (1 :1 w/w), 100% water saturation.
C. Canola oil + saff lower fatty acids (1 :1 w/w), 100% water saturation.
Each sample was treated as in Example 1 , using the first- mentioned lipase. Analysis was done by latroscan after removal of free fatty acids and/or methyl esters. The following results were obtained:
Figure imgf000009_0001
It is seen that the diglyceride content is significantly reduced in 6 hours, and is completely removed within 48 hours.

Claims

1. A process for increasing the amount of triglyceride of a fat or oil containing free fatty acid together with diglyceride, monoglyceride and/or glycerol in the presence of an immobilized lipase, characterized in that the lipase is immobilized by adsorption on a particulate, macroporous non-ionic resin.
2. A process according to Claim 1 , wherein the resin is of the acrylic type.
3. A process according to Claim 1 , wherein the resin is hydrophobic, preferably a polyolefin and most preferably polypropylene.
4. A process for increasing the amount of triglyceride of a fat or oil containing free fatty acid together with diglyceride, monoglyceride and/or glycerol in the presence of a lipase, characterized in that said lipase is positionally non-specific.
5. A process according to Claim 4, wherein the lipase is derived from a strain of Candida, preferably C. cylindracea or C. antarctica, most preferably lipase B or a mixture of lipases A and B from C. antarctica.
6. A process according to Claim 4 or 5 wherein the lipase is in immobilized form.
7. A process according to Claim 6 wherein the lipase is immobilized by adsorption on a particulate, macroporous non-ionic or weakly basic anion exchange resin.
8. A process for increasing the amount of triglyceride of a fat or oil containing free fatty acid together with diglyceride, monoglyceride and/or glycerol in the presence of a lipase, characterized in that said lipase is derived from Humicola.
9. A process according to Claim 8, wherein the lipase is immobilized by adsorption on silica.
10. A process according to a preceding claim in the absence of an organic solvent.
11. A process according to a preceding claim wherein the reaction time is 24 hours or less.
PCT/DK1991/000083 1990-03-23 1991-03-19 A process for increasing the amount of triglyceride of a fat or oil WO1991014784A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DK0758/90 1990-03-23
DK75890A DK75890D0 (en) 1990-03-23 1990-03-23 FAT PROCESSING
DK226490A DK226490D0 (en) 1990-09-20 1990-09-20 FAT PROCESSING
DK2264/90 1990-09-20

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6110508A (en) * 1992-08-21 2000-08-29 Novo Nordisk A/S Use of lipase in baking
EP1314775A1 (en) * 2001-11-21 2003-05-28 Cognis Deutschland GmbH & Co. KG Process for the deacidification of natural fats and oils
WO2003050215A1 (en) * 2001-12-13 2003-06-19 Jott Australia Pty Ltd Process for production of fatty acid esters
AU2002347198B2 (en) * 2001-12-13 2008-04-17 Jott Australia Pty Ltd Process for production of fatty acid esters
CN113150863A (en) * 2021-02-04 2021-07-23 吉林省百利生物科技有限公司 Method for reducing anisidine value of grease by adopting macroporous adsorption resin
WO2021165475A1 (en) * 2020-02-20 2021-08-26 Palsgaard A/S Novel structurizing oil, method of production, and uses in margarine and ice cream

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CHEMCIAL ABSTRACTS, Volume 111, No. 1, 3 July 1989, (Columbus, Ohio, US), HELDT-HANSEN, H.P. et al.: "A New Immobilized Positional Nonspecific Lipase for Fat Modification and Ester Synthesis", see page 301, Abstract 3085c; & ACS SYMP. SER., 1989, 389(), 158-172. *
CHEMICAL ABSTRACTS, Volume 106, No. 21, 25 May 1987, (Columbus, Ohio, US), OMAR, IBRAHIM CHE et al.: "Purification and some Properties of a Thermostable Lipase from Humicola Lanuginosa No. 3", see page 310, Abstract 171667j; & AGRIC. BIOL. CHEM., 1987, 51(1), 37-45. *
CHEMICAL ABSTRACTS, Volume 107, No. 23, 7 December 1987, (Columbus, Ohio, US), OMAR, IBRAHIN CHE et al.: "Fat Hydrolysis and Esterification by a Lipase from Humicola Lanuginosa", see page 262, Abstract 214029t; & AGRIC. BIOL. CHEM., 1987, 51(8), 2153-2159. *
CHEMICAL ABSTRACTS, Volume 108, No. 17, 25 April 1988, (Columbus, Ohio, US), OMAR, IBRAHIM CHE et al.: "Hydrolysis of Triglycerides by Immobilized Ther=Mostable Lipase from humicola Lanuginosa", see page 356, Abstract 146248g; & AGRIC. BIOL. CHEM., 1988, 52(1), 99-105. *
CHEMICAL ABSTRACTS, Volume 111, No. 1, 3 July 1989, (Columbus, Ohio, US), HELDT-HANSEN, HANS PETER et al.: "A New Immobilized Positional Nonspecific Lipase for Fat Modification and Ester Synthesis", see page 301, Abstract 3085c; & ACS SYMP. SER., 1989, 389, 158-172. *
CHEMICAL ABSTRACTS, Volume 111, No. 25, 18 December 1989, (Columbus, Ohio, US), KURASHINGE, J. et al.: "Modification of Fats and Oils by Lipases", see page 611, Abstract 230625; & J. DISPERSION SCI. TECHNOL., 1988, 10(4), 531-539. *
CHEMICAL ABSTRACTS, Volume 112, No. 17, 23 April 1990, (Columbus, Ohio, US), see page 588, Abstract 156751n; & JP,A,1 257 485, "Manufactur of Triglycerides with Lipases from Fatty Acids and Glycerol or Parial Glycerides", 7 April 1988. *
CHEMICAL ABSTRACTS, Volume 114, No. 15, 15 April 1991, (Columbus, Ohio, US), ERGAN, FRANCOISE et al., "Effect of Lipase Specificity on Triglyceride Synthesis", see page 355, Abstract 138912c; & BIOTECHNOL. LETT., 1991, 13(1), 19-24. *
DIALOG INFORMATION SERVICES, File 351, World Patent Index, Accession No. 008079604, KANEGAFUCHI CHEM KK: "Prodn. of Triglyceride by the Aid of Lipase - by Reacting Fatty Acid (Ester) and Glycerol or Partial Glyceride in Presence of Lipase, ESTER"; & JP,A,1 257 485, 13-10-1989, (Basic). *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6110508A (en) * 1992-08-21 2000-08-29 Novo Nordisk A/S Use of lipase in baking
EP1314775A1 (en) * 2001-11-21 2003-05-28 Cognis Deutschland GmbH & Co. KG Process for the deacidification of natural fats and oils
US6897328B2 (en) 2001-11-21 2005-05-24 Cognis Deutschland Gmbh & Co. Kg Process for deacidifying natural fats and oils
WO2003050215A1 (en) * 2001-12-13 2003-06-19 Jott Australia Pty Ltd Process for production of fatty acid esters
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