WO1999053001A1 - Procede de demucilagination de l'huile par des enzymes - Google Patents

Procede de demucilagination de l'huile par des enzymes Download PDF

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Publication number
WO1999053001A1
WO1999053001A1 PCT/DK1999/000202 DK9900202W WO9953001A1 WO 1999053001 A1 WO1999053001 A1 WO 1999053001A1 DK 9900202 W DK9900202 W DK 9900202W WO 9953001 A1 WO9953001 A1 WO 9953001A1
Authority
WO
WIPO (PCT)
Prior art keywords
phospholipase
oil
water
process according
aspergillus
Prior art date
Application number
PCT/DK1999/000202
Other languages
English (en)
Inventor
Kim Clausen
Original Assignee
Novo Nordisk A/S
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 Novo Nordisk A/S filed Critical Novo Nordisk A/S
Priority to EP99911648A priority Critical patent/EP1071734A1/fr
Priority to AU30263/99A priority patent/AU3026399A/en
Priority to CA002324653A priority patent/CA2324653A1/fr
Priority to BR9909502-5A priority patent/BR9909502A/pt
Publication of WO1999053001A1 publication Critical patent/WO1999053001A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/003—Refining fats or fatty oils by enzymes or microorganisms, living or dead

Definitions

  • the present invention relates to an improved process for enzymatic reducing the content of phosphorus containing components in an edible oil.
  • Oils obtained from the usual oil and fat production processes by compressing oil-bearing materials or by extracting oil from the materials and removing the extraction solvent contain impurities such as polar lipids mainly composed of phospholipids, as well as fatty acids, pigments, odor components and the like. Thus it is necessary to remove these impurities by a refining process. Such a process may require a degumming step.
  • EP 622446 suggest to use high amount of water in the enzymatic degumming process. See page 3, line 33-44 and claim 4 in said document, which suggest to use more than 30 percent of water by weight of the oil in said process.
  • the problem, to be solved, by the present invention is to provide a simplified and economically cheaper process for enzymatic degumming of edible oils.
  • the present invention relates to a process for reducing the content of phosphorus containing components in an edible oil, having from 50 to 10.000 part per million (pp ) of phosphorous content, which method comprises contacting said oil at a pH from 1.5 to 8 with an aqueous solution of a -2- phospholipase Al (PLA1) , phospholipase A2 (PLA2) , or phospholipase B (PLB) which is emulsified in the oil until the phosphorous content of the oil is reduced to less than 12 ppm, and then separating the aqueous phase from the treated oil, and wherein said process is characterized by that said emulsified condition is formed using from 0.01 to 1.5 percent of water by weight of the oil, preferably from 0.01 to 1.0 percent of water by weight of the oil, more preferably from 0.01 to 0.75 percent of water by weight of the oil, even more preferably from 0.01 to 0.5 percent of water by
  • the lower range above of 0.01 percent of water by weight of the oil may preferably be 0.1 percent of water by weight of the oil.
  • An advantage of the process described herein is that costs for water and waste water treatment may be reduced. Furthermore, oil recovery yields may be increased because less amount of oil will be wasted to the aqueous phase. Further, an advantage of the process described herein may be that an oil-mill using this process may skip sludge recycling of the polluted water used in the process.
  • Said recycling step may be saved by the low amount of water used in the process described herein.
  • enzymatic degumming carried out according to the art (e.g. US 5,264,367) a heat treatment to e.g. 65-75 °C of the water in oil emulsion is usually carried out in order to facilitate separation of the oil and aqueous phases by e.g. centrifugation.
  • the thermostable phospholipase LecitaseTM Novo Nordisk A/S, Denmark
  • the aqueous phase containing the enzyme can advantageously be reused several times (with or without addition -3-
  • Embodiment (s) of the present invention is described below, by way of example (s) only.
  • any edible oil may be degummed according to a process of the invention.
  • Example of oils are crude oils and water degummed oils.
  • a crude oil (also called a non-degummed oil) may be a pressed or extracted oil or a mixture thereof from e.g. rapeseed, soybean, or sunflower.
  • the phosphatide content in a crude oil may vary from 0.5-3% w/w corresponding to a phosphorus content in the range of 200-10.000 ppm, more preferably in the range of 250-1200 ppm.
  • the crude oil also contains small concentrations of carbohydrates, sugar compounds and metal/phosphatide acid complexes of Ca, Mg and Fe.
  • said edible oil is an oil from which mucilage has previously been removed and which has a phosphorus content from 50 to 250 ppm.
  • Such an oil is generally obtained by a water-degumming process and termed "a water-degummed oil".
  • a water-degummed oil is typically obtained by mixing 1-3% w/w of hot water with warm (60-90°C) crude oil. Usual treatment periods are 30-60 minutes.
  • the water-degumming step removes the phosphatides and mucilaginous gums which become insoluble in the oil when hydrated.
  • the hydrated phosphatides and gums can be separated from the oil by settling, filtering or centrifuging - centrifuging being the more prevalent practice.
  • water-degumming may be called “wet refining to remove mucilage” (see US 5,264,367) . -4-
  • an edible is preferably an vegetable oil.
  • a phospholipase used in the process of the invention is a phospholipase obtained from a microorganism, preferably a filamentous fungus, a yeast, or a bacterium.
  • the term "obtained from”, as used herein in connection with a specific microbial source, means that the enzyme and consequently the DNA sequence encoding said enzyme is produced by the specific source.
  • the enzyme is then obtained from said specific source by standard known methods enabling the skilled person to obtain a sample comprising the enzyme and capable of being used in a process of the invention.
  • Said standard methods may be direct purification from said specific source or cloning of a DNA sequence encoding the enzyme followed by recombinant expression either in the same source (homologous recombinant expression) or in a different source (heterologous recombinant expression) .
  • a phospholipase used in a process of the invention is obtained from a filamentous fungal species within the genus Fusarium, such as a strain of F. cul orum, F. heterosporum, F . solani , or in particular a strain of F. oxysporum; or a filamentous fungal species within the genus Aspergillus, such as a strain of Aspergillus awamori , Aspergillus foetidus, Aspergillus japonicus, Aspergillus niger or in particular Aspergillus oryzae .
  • VOD 5 Degomma VOD (Roehm, Germany) , which is believed to comprise an Aspergillus phospholipase is suitable to be used in a process of the invention.
  • a phospholipase used in a process of the invention exhibits certain properties.
  • embodiment of the invention relates to i) a process according to the invention, wherein the phospholipase is a phospholipase which is substantively independent of Ca 2+ concentration measured as, relative phospholipase activity at 5 mM EDTA and 5mM Ca 2+ in 5 a phospholipase activity assay measuring release of free fatty acids from lecithin in a buffer comprising 2% lecithin, 2% Triton X-100, 20 mM citrate, pH 5; incubated for 10 min. at 37°C followed by stop of reaction at 95°C for 5 min.
  • the ratio of relative phospholipase activity at 5mM 0 EDTA/5 mM Ca 2+ is greater than 0.25, more preferably greater than 0.5; and/or ii ) a process according to the invention, wherein the phospholipase is a phospholipase which has a phospholipase activity which is capable of releasing at least 7 ⁇ mol of free 25 fatty acid/min./mg enzyme; more preferably at least 15 ⁇ mol of free fatty acid/min./mg enzyme; measured as, phospholipase activity is measured in an assay measuring release of free fatty acids from lecithin in a buffer comprising
  • the invention relates to a process according to the invention, wherein the phospholipase is a phospholipase having an polypeptide sequence selected from the group comprising of:
  • a phospholipase obtained from F . oxysporum and having the polypeptide sequence shown in (b) above exhibits both of the above mentioned functional characteristic. Accordingly, this phospholipase is the most preferred phospholipase to be used in a process of the invention. A working example herein demonstrates the use of this phospholipase (vide infra) . Finally an example of a suitable non-microbial phospholipase is the commercial available PL (LecitaseTM, Novo Nordisk A/S, Denmark) obtained from porcine pancreas.
  • the enzymatic treatment is conducted by dispersing an aqueous solution of the phospholipase, preferably as droplets with an average diameter below 10 ⁇ (micro) . -7-
  • the amount of water is from 0.01 to 1.5% by weight in relation to the oil.
  • An emulsifier may optionally be added. Mechanical agitation may be applied to maintain the emulsion.
  • the enzymatic treatment can be conducted at any pH in the range 1.5-8, preferably from pH 3-6.
  • the pH may be adjusted by adding citric acid, a citrate buffer, NaOH or HC1.
  • a suitable temperature is generally 30-75°C (particularly 40-60°C) .
  • the reaction time will typically be 0.5-12 hours (e.g. 2-6 hours) , and a suitable enzyme dosage will usually be 100- 5000 IU per liter of oil, particularly 200-2000 IU/1.
  • the enzymatic treatment may be conducted batchwise, e.g. in a tank with stirring, or it may be continuous, e.g. a series of stirred tank reactors.
  • the enzymatic treatment is followed by separation of an aqueous phase and an oil phase. This separation may be performed by conventional means, e.g. centrifugation.
  • the process of the invention can reduce this value to below 12 ppm, more preferably below 10, and even more preferably below 5 ppm.
  • the equipment consists of a 1 1 jacketed steel reactor fitted with a steel lid, a propeller (about 600 rpm) , baffles, a temperature sensor, an inlet tube at the top, a reflux condenser (about 4°C) at the top, and an outlet tube at the bottom.
  • the reactor jacket is connected to a thermostat bath.
  • the outlet tube is connected via silicone tubing to a Silverson in-line mixer head equipped with a "square hole high shear screen", driven by a Silverson L4RT high shear lab mixer (about 8500 rpm, flow ca. 1.1 1/minute) .
  • the mixer head is fitted with a cooling coil (5-10 °C) and an outlet tube, which is connected to the -8-
  • the reactor/mixer system is emptied and rinsed with 2x500 ml 10% Deconex/DI water solution followed by minimum 3x500 ml of DI water.
  • Table 2 is a presentation of the various additions and samplings during the reaction.
  • Phosphorus analysis Take 10 ml of water in oil emulsion in a glass centrifuge tube. Heat the emulsion in a boiling water bath for 30 minutes. Centrifuge at 5000 rpm for 10 minutes. Transfer about 8 ml of upper (oil) phase to a 12 ml polystyrene tube and leave it (to settle) for 12-24 hours. After settling draw about 1-2 g from the upper clear phase for P-analysis.
  • a calibration curve was obtained by dissolving 0.6 g of citric acid monohydrate in 27 g of DI water; pH of this solution was measured by pH electrode Orion (pH real ) . 100 ⁇ l were mixed with 2 ml MilliQ water, and pH of this solution was measured by pH electrode Orion (pH measured ) . pH of the citric acid solution was changed gradually by adding NaOH solution, and for each adjustment dilution and pH measurements were carried out as described above.)
  • the enzyme was recombinantly expressed and purified as described in EP Patent application number 97610056.0.
  • Phospholipase activity was measured as the release of free fatty acids from lecithin. 50 ⁇ l 4% L-alpha- phosphatidylcholine (plant lecithin from Avanti, USA) , 4% Triton X-100, 5 mM CaCl 2 in 50 mM HEPES, pH 7 was added, 50 ⁇ l enzyme solution diluted to an appropriate concentration in 50 mM HEPES, pH 7. The samples were incubated for 10 min at 30°C and the reaction stopped at 95 °C for 5 min prior to centrifugation (5 min at 7000 rpm) .
  • Free fatty acids were determined using the NEFA C kit from Wako Chemicals GmbH; 25 ⁇ l reaction mixture was added to 250 ⁇ l reagent A and incubated for 10 min at 37°C. Then 500 ⁇ l Reagent B was added and the sample was incubated again, 10 min at 37 °C. The absorption at 550 nm was measured using an HP 8452A diode array spectrophotometer. Samples were run at least in duplicates. Substrate and enzyme blinds (preheated enzyme samples (10 min at 95°C) + substrate) were included. Oleic acid was used as a fatty acid standard. 1 PHLU equals the amount of enzyme capable of releasing 1 ⁇ mol of free fatty acid/min under these conditions.
  • the assay was run at 37°C in 20 mM citrate buffer, pH 5 (Ca 2+ -dependence) or 20 mM Britton-Robinson buffer (pH-profile/temperature-profile/stability) .
  • Phospholipase Al activity was measured using 1-(S- decanoyl) -2-decanoyl-l-thio-sn-glycero-3-phosphocholine (D3761
  • HEPES, 0.3 mM DTNB, 2 mM CaCl 2 , pH 7) in a 200 ⁇ l cuvette were added to 10 ⁇ l enzyme, and the absorption at 410 nm was measured as a function of time on the HP 8452A diode array spectrophotometer at room temperature. Activity was calculated as the slope of the curve in the linear range.
  • PLA1 equals the amount of enzyme capable of releasing 1 ⁇ mol of free fatty acid (thiol)/min at these conditions. -17-
  • Phospholipase A2 activity was measured at 40°C using 1- hexadecanoyl-2- (1-pyrenedecanoyl) -sn-glycero-3-phosphocholine (H361 Molecular Probes) .
  • 2 ml substrate 50 ⁇ l 1% Triton X-100 + 25 ⁇ l 0.1% H361 in methanol + 10 ml 50mM HEPES, pH 7) in a 2 ml cuvette with stirring was added to 10 ⁇ l enzyme, and the pyrene fluorescence emission was measured at 376 nm (excitation at 340 nm) as a function of time (1 sec. intervals) using the Perkin Elmer LS50 apparatus.
  • Triton X-100/phospholipid micelles the concentration of phospholipid was adjusted to have excimer formation (emits at 480 nm) . Upon cleavage the fatty acid in the 2-position containing the pyrene group is released into the aqueous phase resulting in an increase in the monomer emission. PLA2 was taken as the slope of the curve in the linear range at equal conditions.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Edible Oils And Fats (AREA)

Abstract

La présente invention concerne un procédé amélioré de réduction enzymatique des composants phosphorés présents dans une huile alimentaire. Ce procédé fait intervenir une phospholipase et une faible quantité d'eau.
PCT/DK1999/000202 1998-04-08 1999-04-07 Procede de demucilagination de l'huile par des enzymes WO1999053001A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP99911648A EP1071734A1 (fr) 1998-04-08 1999-04-07 Procede de demucilagination de l'huile par des enzymes
AU30263/99A AU3026399A (en) 1998-04-08 1999-04-07 An enzymatic oil-degumming process
CA002324653A CA2324653A1 (fr) 1998-04-08 1999-04-07 Procede de demucilagination de l'huile par des enzymes
BR9909502-5A BR9909502A (pt) 1998-04-08 1999-04-07 Processo para redução do teor de componentes contendo fósforo em um óleo edìvel

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK0506/98 1998-04-08
DK50698 1998-04-08

Publications (1)

Publication Number Publication Date
WO1999053001A1 true WO1999053001A1 (fr) 1999-10-21

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Application Number Title Priority Date Filing Date
PCT/DK1999/000202 WO1999053001A1 (fr) 1998-04-08 1999-04-07 Procede de demucilagination de l'huile par des enzymes

Country Status (7)

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EP (1) EP1071734A1 (fr)
CN (1) CN1139652C (fr)
AR (1) AR017484A1 (fr)
AU (1) AU3026399A (fr)
BR (1) BR9909502A (fr)
CA (1) CA2324653A1 (fr)
WO (1) WO1999053001A1 (fr)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000852A2 (fr) * 2000-06-26 2002-01-03 Novozymes A/S Lipase
WO2003102118A2 (fr) * 2002-05-30 2003-12-11 Council Of Scientific And Industrial Research Procede de pre-traitement d'huiles vegetales en vue de leur raffinage physique
JP2007528732A (ja) * 2004-03-12 2007-10-18 ダニスコ エイ／エス 真菌脂肪分解酵素
WO2008094847A1 (fr) * 2007-01-30 2008-08-07 Bunge Oils, Inc. Dégommage enzymatique utilisant un mélange de phospholipases pla et plc
WO2009081094A2 (fr) * 2007-12-21 2009-07-02 Danisco A/S Procédé
US7615241B2 (en) 2004-09-15 2009-11-10 De Smet Engineering N.V. Vapor scrubbing process and apparatus
US7670634B2 (en) 2003-08-06 2010-03-02 De Smet Engineering N.V. Method for vacuum stripping of oils and fats
US7696369B2 (en) * 2004-08-06 2010-04-13 De Smet Engineering N.V. Oil Recuperation process
WO2010150213A1 (fr) * 2009-06-25 2010-12-29 Danisco A/S Protéine
US7892335B2 (en) 2006-09-28 2011-02-22 N.V. Desmet Ballestra Engineering S.A. Phase transfer apparatus and process
EP2302042A3 (fr) * 2004-09-30 2011-08-10 Novozymes A/S Polypeptides dotés d'activité lipase et polynucléotides les codant
USRE43135E1 (en) 2001-05-18 2012-01-24 Danisco A/S Method of improving dough and bread quality
US8142178B2 (en) 2007-08-01 2012-03-27 N.V. Desmet Ballestra Engineering S.A. Device for desolventising under reduced pressure
USRE43341E1 (en) 1995-06-07 2012-05-01 Danisco A/S Method of improving the properties of a flour dough, a flour dough improving composition and improved food products
US8203014B2 (en) 2006-01-20 2012-06-19 N.V. De Smet Engineering S.A. Fractionation processes and devices for oils and fats
US8241876B2 (en) 2008-01-07 2012-08-14 Bunge Oils, Inc. Generation of triacylglycerols from gums
US8460905B2 (en) 2007-09-11 2013-06-11 Bunge Oils, Inc. Enzymatic degumming utilizing a mixture of PLA and PLC phospholipases with reduced reaction time
US8889371B2 (en) 2004-07-16 2014-11-18 Dupont Nutrition Biosciences Aps Lipolytic enzyme: uses thereof in the food industry
US8956853B2 (en) 2007-01-30 2015-02-17 Bunge Oils, Inc. Enzymatic degumming utilizing a mixture of PLA and PLC phospholipases
US9657319B2 (en) 2012-06-14 2017-05-23 Bunge Global Innovation Llc Process for production of low saturate oils
CN110760503A (zh) * 2019-05-07 2020-02-07 宁波大学 一种磷脂酶d的共交联固定化方法
CN113122382A (zh) * 2019-12-31 2021-07-16 丰益(上海)生物技术研发中心有限公司 一种低污染物含量的油脂的制备方法

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ATE231186T1 (de) 1998-07-21 2003-02-15 Danisco Lebensmittel
US7226771B2 (en) * 2002-04-19 2007-06-05 Diversa Corporation Phospholipases, nucleic acids encoding them and methods for making and using them
MXPA05007653A (es) 2003-01-17 2005-09-30 Danisco Metodo.
US7955814B2 (en) 2003-01-17 2011-06-07 Danisco A/S Method
US20050196766A1 (en) 2003-12-24 2005-09-08 Soe Jorn B. Proteins
US7906307B2 (en) 2003-12-24 2011-03-15 Danisco A/S Variant lipid acyltransferases and methods of making
US7718408B2 (en) 2003-12-24 2010-05-18 Danisco A/S Method
GB0716126D0 (en) 2007-08-17 2007-09-26 Danisco Process
CN100441668C (zh) * 2006-06-09 2008-12-10 中国农业科学院油料作物研究所 超声波强化生物酶油脂脱胶的方法
BR122020023911B1 (pt) * 2010-11-12 2022-02-15 Novozymes A/S Construto de ácido nucleico, célula microbiana hospedeira recombinante, e, método de produção do polipeptídeo
EP2792735A1 (fr) * 2013-04-16 2014-10-22 Clariant Produkte (Deutschland) GmbH Procédé d'amélioration de la démucilagination enzymatique aqueuse d'huiles végétales
CN104630175B (zh) * 2013-11-14 2019-10-25 丰益(上海)生物技术研发中心有限公司 一种磷脂酶c
CN106590920A (zh) * 2016-11-22 2017-04-26 汪逸凡 一种植物油脱胶剂的制备方法
US11999923B2 (en) * 2018-05-07 2024-06-04 Dsm Ip Assets B.V. Process for enzymatic oil degumming

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Cited By (37)

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Publication number Priority date Publication date Assignee Title
USRE43341E1 (en) 1995-06-07 2012-05-01 Danisco A/S Method of improving the properties of a flour dough, a flour dough improving composition and improved food products
WO2002000852A3 (fr) * 2000-06-26 2003-11-20 Novozymes As Lipase
WO2002000852A2 (fr) * 2000-06-26 2002-01-03 Novozymes A/S Lipase
EP2281878A1 (fr) * 2000-06-26 2011-02-09 Novozymes A/S Enzyme lipolytique.
EP2119773A1 (fr) * 2000-06-26 2009-11-18 Novozymes A/S Enzyme lipolytique des souches fusarium ou acremonium
USRE43135E1 (en) 2001-05-18 2012-01-24 Danisco A/S Method of improving dough and bread quality
WO2003102118A2 (fr) * 2002-05-30 2003-12-11 Council Of Scientific And Industrial Research Procede de pre-traitement d'huiles vegetales en vue de leur raffinage physique
WO2003102118A3 (fr) * 2002-05-30 2004-04-08 Council Scient Ind Res Procede de pre-traitement d'huiles vegetales en vue de leur raffinage physique
US7670634B2 (en) 2003-08-06 2010-03-02 De Smet Engineering N.V. Method for vacuum stripping of oils and fats
JP2007528732A (ja) * 2004-03-12 2007-10-18 ダニスコ エイ／エス 真菌脂肪分解酵素
JP4751877B2 (ja) * 2004-03-12 2011-08-17 ダニスコ エイ／エス 真菌脂肪分解酵素
US8889371B2 (en) 2004-07-16 2014-11-18 Dupont Nutrition Biosciences Aps Lipolytic enzyme: uses thereof in the food industry
US7696369B2 (en) * 2004-08-06 2010-04-13 De Smet Engineering N.V. Oil Recuperation process
US7615241B2 (en) 2004-09-15 2009-11-10 De Smet Engineering N.V. Vapor scrubbing process and apparatus
EP2302042A3 (fr) * 2004-09-30 2011-08-10 Novozymes A/S Polypeptides dotés d'activité lipase et polynucléotides les codant
US9303248B2 (en) 2004-09-30 2016-04-05 Novozymes A/S Polypeptides having lipase activity and polynucleotides encoding same
US8377675B2 (en) 2004-09-30 2013-02-19 Novozymes, Inc. Polypeptides having lipase activity and polynucleotides encoding same
US8203014B2 (en) 2006-01-20 2012-06-19 N.V. De Smet Engineering S.A. Fractionation processes and devices for oils and fats
US7892335B2 (en) 2006-09-28 2011-02-22 N.V. Desmet Ballestra Engineering S.A. Phase transfer apparatus and process
WO2008094847A1 (fr) * 2007-01-30 2008-08-07 Bunge Oils, Inc. Dégommage enzymatique utilisant un mélange de phospholipases pla et plc
US8956853B2 (en) 2007-01-30 2015-02-17 Bunge Oils, Inc. Enzymatic degumming utilizing a mixture of PLA and PLC phospholipases
RU2477746C2 (ru) * 2007-01-30 2013-03-20 Бандж Ойлз, Инк. Ферментативное обессмоливание с использованием смеси фосфолипаз pla и plc
US8142178B2 (en) 2007-08-01 2012-03-27 N.V. Desmet Ballestra Engineering S.A. Device for desolventising under reduced pressure
US8460905B2 (en) 2007-09-11 2013-06-11 Bunge Oils, Inc. Enzymatic degumming utilizing a mixture of PLA and PLC phospholipases with reduced reaction time
WO2009081094A3 (fr) * 2007-12-21 2010-03-04 Danisco A/S Procédé
AU2008339660B2 (en) * 2007-12-21 2013-09-26 Dupont Nutrition Biosciences Aps Process for edible oil refining using a lipid acyltransferase
EA020035B1 (ru) * 2007-12-21 2014-08-29 ДюПон НЬЮТРИШН БАЙОСАЙЕНСИЗ АпС Способы
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CN110760503A (zh) * 2019-05-07 2020-02-07 宁波大学 一种磷脂酶d的共交联固定化方法
CN110760503B (zh) * 2019-05-07 2023-03-17 宁波大学 一种磷脂酶d的共交联固定化方法
CN113122382A (zh) * 2019-12-31 2021-07-16 丰益(上海)生物技术研发中心有限公司 一种低污染物含量的油脂的制备方法
CN113122382B (zh) * 2019-12-31 2024-02-20 丰益(上海)生物技术研发中心有限公司 一种低污染物含量的油脂的制备方法

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AR017484A1 (es) 2001-09-05
BR9909502A (pt) 2000-12-12
CA2324653A1 (fr) 1999-10-21
AU3026399A (en) 1999-11-01
CN1139652C (zh) 2004-02-25
EP1071734A1 (fr) 2001-01-31
CN1293706A (zh) 2001-05-02

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