WO1991003946A1 - Extraction de jaune d'×uf liquide frais - Google Patents

Extraction de jaune d'×uf liquide frais Download PDF

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Publication number
WO1991003946A1
WO1991003946A1 PCT/CA1990/000243 CA9000243W WO9103946A1 WO 1991003946 A1 WO1991003946 A1 WO 1991003946A1 CA 9000243 W CA9000243 W CA 9000243W WO 9103946 A1 WO9103946 A1 WO 9103946A1
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WO
WIPO (PCT)
Prior art keywords
volume
fraction
egg
yolk
aqueous ethanol
Prior art date
Application number
PCT/CA1990/000243
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English (en)
Inventor
Jeong S. Sim
Original Assignee
Canadian Egg Marketing Agency
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 Canadian Egg Marketing Agency filed Critical Canadian Egg Marketing Agency
Publication of WO1991003946A1 publication Critical patent/WO1991003946A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin

Definitions

  • This invention relates to the extraction of fresh liquid egg yolk and particularly the isolation of lecithin from fresh liquid egg yolk of hens eggs and more especially it relates to the isolation of lecithin (phospholip ds ) , neutral egg yolk oil (neutral lipids which are mainly triglyce ⁇ des) and egg yolk protein from fresh liquid egg yolk of hens eggs.
  • lecithin phospholip ds
  • neutral egg yolk oil neutral lipids which are mainly triglyce ⁇ des
  • egg yolk protein from fresh liquid egg yolk of hens eggs.
  • Lecithin is useful in the food and pharmaceutical industry while egg oil is useful in the preparation of infant formula food because of its fatty acid composition.
  • Egg yolk protein s useful as a source of protein.
  • U.S. patent No 4,425,276 issued January 10, 1984 describes the preparation of highly purified phosphatidy - choline free from oils and phosphatidylethanolamine by placing the starting material as a solution n an aqueous alkanol at the head of a chromatographic column of silicic acid gel at a temperature of 40°C to 90°C and eluting the column with an aqueous alkanol.
  • U.S. patent No. 4,443,378 issued April 17, 1984 describes the use of 95% ethanol in the separation of acylated phospholipids in a chromatographic purification procedure.
  • U.S. patent No. 4,496,486 issued January 29, 1985 describes the purification of crude phosphatides, e.g.
  • Canadian patent No. 1,064,907 issued October 23, 1979 describes the treatment of dried egg yolk powder with aqueous 95% ethanol at a temperature of 25° to 30°C for 2 to 4 hours to remove at least 70% by weight of cholesterol contained in the dried egg yolk powder.
  • the drawing is a schematic flow sheet of the process showing the separation of fresh liquid egg yolk into solid yolk residue (protein), neutral egg oil (triflycerides) and egg lecithin (phospholipids) .
  • fresh liquid egg yolk from hens eggs can be subjected to a unique novel process using a precise combination of solvent and temperature to provide a high yield of egg yolk protein, lecithin (phospholipids) and neutral egg yolk oil (triglycerides) .
  • a process for the separation of fresh liquid egg yolk into a yolk protein fraction, a neutral egg oil fraction and an egg lecithin fraction which comprises treating fresh liquid egg yolk with aqueous ethanol at an elevated temperature to provide a slurry thereof, separating the slurry into a solid fraction and a liquid fraction, for example by filtration, to provide a solid fraction which is solid yolk protein and a liquid fraction which is an aqueous ethanolic solution, and thereafter subjecting the aqueous ethanolic solution to low temperature crystallation to provide a crystalline neutral egg oil fraction and removing this crystalline fraction to provide a residual aqueous ethanolic solution containing egg lecithin.
  • Fresh liquid egg yolk from hens eggs contains about 50% water and about 50% solid matter and the latter is essentially made up of yolk protein and lipids.
  • These lipids are a complex mixture of t ⁇ g yce ⁇ des (also called neutral lipids or neutral egg oil) and phospholipids which are polar lipids containing lecithin, together with cholesterol. It is possible to use the process of the present invention to isolate first the yolk protein essentially free from lipids and thereafter to separate the residual lipids into a neutral lipid fraction known as neutral egg oil (t ⁇ glycerides) and egg lecithin which is essentially phospholipids, i.e. polar lipids containing lecithin. These products thus obtained by the process of this invention are essentially free from, or contain only very minor amounts of, cholesterol.
  • neutral egg oil t ⁇ glycerides
  • egg lecithin which is essentially phospholipids, i.e. polar lipids containing lecithin.
  • the drawing shows a preferred embodiment of the process wherein 1 part by weight of fresh liquid egg yolk is stirred with 4 volumes of 95% aqueous ethanol (95% by volume of ethanol w th 5% by volume of water) at a temperature of about 60°C for about 15 minutes.
  • the slurry thus obtained is separated, for example by f ltration, and the solid yolk residue is essentially yolk protein free from lipids.
  • the residual aqueous ethanolic solution is subjected to low temperature crystallization, e.g. a tern- perature of about 2°C to 5°C.
  • the crystalline product which separates is essentially neutral triglycerides which is commonly known as neutral egg oil since it is crystalline at the temperature of 2°C to 5°C but liquefies at ambient temperature.
  • the residual aqueous ethanolic solution may be dried, for example in a vacuum evaporator, to remove the aqueous ethanol and provide a final solid residue which is essentially egg lecithin.
  • a process for the separation of fresh liquid egg yolk into a yolk protein fraction, a neutral, egg oil fraction and an egg lecithin fraction which comprises treating about 100 parts by weight of fresh liquid egg yolk with about 400 volumes (1:4 weight to volume) of aqueous ethanol (5% by volume of water and 95% by volume of ethanol) at a temperature of about 60°C to provide a slurry thereof, separating said slurry, for example by filtration, to provide a solid fraction which is solid yolk protein and a liquid fraction which is an aqueous ethanolic solution, and thereafter subjecting said solution to low temperature crystallization to provide a crystalline neutral egg oil fraction and removing said crystalline fraction to provide a residual aqueous ethanolic solution containing egg lecithin.
  • a process for the separation of fresh liquid egg yolk into a yolk protein fraction, a neutral egg oil fraction and an egg lecithin fraction which comprises treating about 100 parts by weight of fresh liquid egg yolk with about 400 volumes (1:4 weight to volume) of aqueous ethanol (5% by volume of water and 95% by volume of ethanol) at a temperature of about 60°C to provide a slurry thereof, separating said slurry, for example by
  • TE SHEET filtration to provide a solid fraction which is solid yolk protein and a liquid fraction which is an aqueous ethanolic solution, and thereafter subjecting said solution to crystallization at a temperature of from about 2°C to about 5°C to provide a crystalline neutral egg oil fraction and removing said crystalline fraction to provide a residual aqueous ethanolic solution containing egg lecithin.
  • the novel process of this invention it is possible to separate fresh liquid egg yolk from hens eggs into three products.
  • the first product is yolk protein
  • the second product is neutral egg yolk oil so- called because it is an oil at ambient temperature and a crystalline product at a lower temperature of about 2°C to 5°C while the third product is egg lecithin.
  • These products contain little or no undesirable byproducts and they are therefore very desirable products for use in the food and pharmaceutical industries.
  • aqueous ethanol used herein is intended to mean ethanol containing from about 2% volume to volume of water (i.e. about 98% by volume of ethanol. and about 2% by volume of water) to about 10% volume to volume of water (i.e. about 90% by volume of ethanol and about 10% by volume of water).
  • a preferred aqueous ethanol is one containing from about 4% volume to volume to about 6% volume to volume of water, i.e. from about 96% by volume to about 94% by volume of ethanol, and, more especially, one containing about 5% volume to volume of water, i.e. 95% by volume of ethanol and 5% by volume of water.
  • (v) of aqueous ethanol used in the process in relation to the weight (w) of fresh liquid egg yolk used as starting material may vary from about 2 volumes, i.e. 2 v/w (volume to weight) to about 5 volumes, i.e. 5 v/w (volume to weight), and preferably from about 3 volumes to about 5 volumes (3 v/w to 5 v/w) and more particulary about 4 volumes, i.e. 4 v/w.
  • aqueous ethanol desirably containing 95% by volume of ethanol and 5% by volume of water
  • elevated temperature is intended to mean a temperature of from about 45°C to about 75°C, preferably from about 55°C to about 65°C and more particularly a temperature of from about 58°C to about 62°C. A most preferred temperature is about 60°C.
  • the time taken for treatment of the fresh liquid egg yolk with aqueous ethanol to prepare a slurry thereof may vary from about 5 minutes to about 60 minutes but it has generally been found that the separation of the solid yolk protein fraction occurs fairly quickly.
  • a preferred operating temperature is about 60°C and the time for treatment is generally about 15 minutes before the slurry thus obtained is ready for separation to separate the solid yolk residue from the aqueous ethanolic liquid.
  • Treatment of fresh liquid egg yolk with aqueous ethanol according to the process of this invention is effective in precipitating the solid yolk protein fraction while the residual aqueous ethanolic liquid contains essentially the neutral egg yolk oil and the lecithin.
  • the residual aqueous ethanolic solution can be cooled to a sufficiently low temperature to permit the neutral egg yolk oil to crystallize out from the solution.
  • a suitable low temperature below ambient temperature of from about 0°C to about lOoc, preferably from about 2°C to about 8°C, and
  • SHEET especially a temperature of from about 2°C to about 5°C.
  • the residual aqueous ethanolic filtrate may be dried, for example by use of a rotary vacuum evaporator, to remove the water and ethanol under relatively mild conditions.
  • the solid residue thus obtained is essentially lecithin which may be further purified, as required, by known means.
  • the crystalline product which is neutral egg oil in its crystalline state may be washed at low temperature with a small amount of cold aqueous ethanol to remove adhering traces of the filtrate from which it has been separated.
  • the crystalline product may then be allowed to warm up to ambient temperature when it liquefies and the neutral egg yolk oil thus obtained is essentially a mixture of triglycerides.
  • the oil may be further purified by a recrystallization procedure.
  • the originally isolated egg yolk protein may be retreated with aqueous ethanol to remove residual traces of undesired products and the slurry thus obtained may be filtered to obtain purified egg yolk protein.
  • fresh liquid egg yolk means unprocessed, unspoiled, natural liquid egg yolk, to be used as starting material, which has been obtained from hens eggs, irrespective of the age of said eggs.
  • EXAMPLE 1 100 g Of fresh liquid egg yolk which contains approximately 50% of solid matter (i.e. about 50 g of solid matter and about 50 g of water), is diluted with 400 ml
  • SUBSTITUTE S residue which is essentially lipid-free egg yolk protein.
  • the aqueous ethanolic filtrate contains egg yolk lipids (fat).
  • the aqueous ethanolic filtrate is then cooled to a temperature of from about 2°C to about 5°C for a period of about 12 hours (roughly overnight).
  • the neutral lipids (triglycerides ) in the aqueous ethanolic filtrate crystallize out and are precipitated at the bottom.
  • the bottom crystalline product (mainly triglycerides ) is separated from the aqueous ethanol solution by filtering through a *Whatman #2 ashless filter paper.
  • the crystalline product thus collected is transferred into a round bottomed flask with several rinsings of hot ethanol and is then dried (remove aqueous ethanol) by a rotary vacuum evaporator.
  • the product is designated as "Neutral Egg Oil” (97.03% triglycerides) .
  • the remaining aqueous ethanolic filtrate after the removal of neutral egg oil (triglycerides), is dried in a rotary vacuum evaporator at 40°C.
  • the solid fraction thus obtained is designated as "Egg Lecithin” (89.16% phospholipids) .
  • the initially obtained solid yolk residue which is essentially lipid free egg yolk protein may be subjected to a further treatment with 100 ml of 95% aqueous ethanol in order to remove residual traces of lipids.
  • the slurry thus produced is filtered and the solid residue of egg yolk protein thus obtained is free from lipids.
  • the neutral egg oil (97.03% triglycerides) contains only trace amounts (0.04% to 0.12%) of cholesterol. This cholesterol may be reduced or removed completely by subjecting the egg oil to a recrystallization procedure using aqueous ethanol or by subjecting the egg oil to a supercritical fluid extraction procedure.
  • Example 2 SUBSTITUTE SHEET extraction over different time periods (15, 30 and 60 minutes) and at different temperatures (40°C and 60°C), the process described in Example 1 was further evaluated as follows:- To 100 g of fresh liquid egg yolk (containing approximately 48.1% water, 35.0% lipids, 15.1% protein and 1.8% ash) were added 400 ml (1:4 weight to volume) of 95% aqueous ethanol (95% by volume of ethanol and 5% by volume of water) . The slurry was homogenized in a blender and charged into the chamber of an extraction/filtration (EF) unit in the extraction mode. Extraction was continued by stirring for 15, 30 or 60 minutes.
  • EF extraction/filtration
  • the slurry was isothermally filtered at 40°C or 60°C with a gradually increasing pressure in order to prevent clogging of the filter.
  • a triple layer of *FYNTEX 300 mesh (pore size 79 ⁇ m) nylon filter was found to be suitable for this purpose.
  • the aqueous ethanolic filtrate was collected and stored overnight (about 12 to 16 hours) at 2°C to 5°C.
  • Two phases formed, one a crystalline precipitate at the bottom of the flask, which is essentially tr glycerides, and an isotropic liquid phase at the top, which contains polar lipids, mainly lecithin.
  • the two phases were separated by filtering using a Whatman #2 ashless filter paper in a cold room temperature
  • the crystalline phase containing neutral egg oil (triglycerides) and the liquid upper phase containing mainly polar lipids (lecithin) were each subjected separately to a drying process by evaporation at 40°C in a rotary vacuum evaporator.
  • PL phospholipids (polar lipids containing lecithin) .
  • FC free cholesterol
  • TG triglycerides (neutral lipids) .
  • 100 g Of fresh liquid egg yolk was extracted with 200, 300, 400 or 500 ml of 95% aqueous ethanol (95% by volume of ethanol and 5% by volume of water) at 60°C for 15 minutes. Extraction, filtration and cold temperature fractionation were performed as described in Example 2. As seen in the following table, a 4:1 volume to weight ratio gives 96.36% extractability, producing 11 g of crude lecithin and 22 g of neutral egg oil per 100 g of fresh liquid egg yolk, with a high purity. A ratio higher than 4:1 volume to weight (v/w) of 95% ethanol appears to increase the total extractability but the lecithin fraction becomes less pure mainly due to the shift of triglycerides to the lecithin fraction in the cold temperature fractionation step. Therefore, 400 ml per 100 g (4:1 v/w ratio) was adopted as the best procedure.

Abstract

L'invention se rapporte à un nouveau procédé permettant de séparer du jaune d'÷uf liquide frais en une fraction de protéines de jaune d'÷uf, en une fraction d'huile d'÷uf neutre et en une fraction de lécithine d'÷uf. Ce procédé consiste à traiter du jaune d'÷uf liquide frais avec de l'éthanol aqueux à une température élevée, afin de former une pâte, à filtrer la pâte pour obtenir des protéines de jaune d'÷uf solides et un filtrat d'éthanol aqueux, puis à soumettre ce filtrat à une opération de cristallisation à base température, pour obtenir une fraction d'huile d'÷uf neutre cristalline, et à retirer la fraction cristalline pour obtenir un filtrat résiduel qui consiste en une solution d'éthanol aqueux contenant de la lécithine d'÷uf.
PCT/CA1990/000243 1989-09-21 1990-07-31 Extraction de jaune d'×uf liquide frais WO1991003946A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA612,411 1989-09-21
CA000612411A CA1335054C (fr) 1989-09-21 1989-09-21 Extraction de jaune d'oeuf liquide frais

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5883273A (en) * 1996-01-26 1999-03-16 Abbott Laboratories Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds
US5917068A (en) * 1995-12-29 1999-06-29 Eastman Chemical Company Polyunsaturated fatty acid and fatty acid ester mixtures free of sterols and phosphorus compounds
US6063946A (en) * 1996-01-26 2000-05-16 Eastman Chemical Company Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds
US6200624B1 (en) 1996-01-26 2001-03-13 Abbott Laboratories Enteral formula or nutritional supplement containing arachidonic and docosahexaenoic acids
AT6609U3 (de) * 2003-04-07 2004-04-26 Unipack Ges M B H Abfuell Und Verfahren zum herstellen einer klaren lecithin enthaltenden oralen zubereitung
US7235515B2 (en) * 2004-02-11 2007-06-26 Ibnsina Karkenny Method of making a lubrication additive
WO2009095435A1 (fr) 2008-01-30 2009-08-06 Bnlfood Investments Sarl Composition à base de lécithine et son utilisation dans l'alimentation
WO2009132685A1 (fr) * 2008-04-28 2009-11-05 L. Raphael Sa Composition comportant des phospholipides en combinaison avec de l'acide ascorbique et produits cosmétiques la comportant
CN102863470A (zh) * 2012-09-10 2013-01-09 江苏大学 蛋黄卵磷脂、脑磷脂、蛋黄油及低变性蛋白粉的联产方法
CN102863469A (zh) * 2012-09-10 2013-01-09 江苏大学 一种高纯度蛋黄卵磷脂的制备方法
WO2014042509A1 (fr) 2012-09-12 2014-03-20 Sime Darby Malaysia Berhad Extraction de lécithine à partir d'un déchet agro-industriel de palme

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10018213A1 (de) 2000-04-12 2001-10-25 Westfalia Separator Ind Gmbh Verfahren zur Fraktionierung von öl-und lecithinhaltigen nativen Rohstoffen
US7566570B2 (en) * 2004-01-26 2009-07-28 Martek Biosciences Corporation Method for the separation of phospholipids from phospholipid-containing materials
US20170058233A1 (en) * 2015-08-24 2017-03-02 Hui Wang Method for fractionation of a protein and lipid containing material

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4157404A (en) * 1978-07-28 1979-06-05 Asahi Kasei Kogyo Kabushiki Kaisha Process for obtaining yolk lecithin from raw egg yolk
JPS62186744A (ja) * 1986-02-13 1987-08-15 Morinaga Milk Ind Co Ltd 母乳代替ミルク組成物
JPS62263192A (ja) * 1986-05-09 1987-11-16 Nisshin Oil Mills Ltd:The 卵黄レシチンの製造方法
EP0259495A1 (fr) * 1986-02-10 1988-03-16 Q.P. Corporation Procede de production de lecithine de jaune d'oeuf contenant une quantite reduite de phosphatidyle-ethanolamine (pe) et/ou ne contenant essentiellement aucune impurete

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4157404A (en) * 1978-07-28 1979-06-05 Asahi Kasei Kogyo Kabushiki Kaisha Process for obtaining yolk lecithin from raw egg yolk
EP0259495A1 (fr) * 1986-02-10 1988-03-16 Q.P. Corporation Procede de production de lecithine de jaune d'oeuf contenant une quantite reduite de phosphatidyle-ethanolamine (pe) et/ou ne contenant essentiellement aucune impurete
JPS62186744A (ja) * 1986-02-13 1987-08-15 Morinaga Milk Ind Co Ltd 母乳代替ミルク組成物
JPS62263192A (ja) * 1986-05-09 1987-11-16 Nisshin Oil Mills Ltd:The 卵黄レシチンの製造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN, Volume 12, No. 148 (C-493) (2995), 7 May 1988, & JP, A, 62263192 (Nisshin Oil Mills Ltd) 16 November 1987 see Abstract *
PATENT ABSTRACTS OF JAPAN, Volume 12, No. 37 (C-473) (2884), 4 February 1988, & JP, A, 62186744 (Morinaga Milk Inc. Co. Ltd) 15 August 1987 see Abstract *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5917068A (en) * 1995-12-29 1999-06-29 Eastman Chemical Company Polyunsaturated fatty acid and fatty acid ester mixtures free of sterols and phosphorus compounds
US5883273A (en) * 1996-01-26 1999-03-16 Abbott Laboratories Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds
US6063946A (en) * 1996-01-26 2000-05-16 Eastman Chemical Company Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds
US6200624B1 (en) 1996-01-26 2001-03-13 Abbott Laboratories Enteral formula or nutritional supplement containing arachidonic and docosahexaenoic acids
AT6609U3 (de) * 2003-04-07 2004-04-26 Unipack Ges M B H Abfuell Und Verfahren zum herstellen einer klaren lecithin enthaltenden oralen zubereitung
US7235515B2 (en) * 2004-02-11 2007-06-26 Ibnsina Karkenny Method of making a lubrication additive
WO2009095435A1 (fr) 2008-01-30 2009-08-06 Bnlfood Investments Sarl Composition à base de lécithine et son utilisation dans l'alimentation
EP2100897A1 (fr) 2008-01-30 2009-09-16 BNLfood Investments SARL Composition à base de lécithine et son utilisation dans les aliments
EP2250179B1 (fr) 2008-01-30 2020-01-22 AAK AB (publ) Composition à base de lécithine et son utilisation dans les aliments
WO2009132685A1 (fr) * 2008-04-28 2009-11-05 L. Raphael Sa Composition comportant des phospholipides en combinaison avec de l'acide ascorbique et produits cosmétiques la comportant
CN102863470A (zh) * 2012-09-10 2013-01-09 江苏大学 蛋黄卵磷脂、脑磷脂、蛋黄油及低变性蛋白粉的联产方法
CN102863469A (zh) * 2012-09-10 2013-01-09 江苏大学 一种高纯度蛋黄卵磷脂的制备方法
CN102863469B (zh) * 2012-09-10 2015-04-22 江苏大学 一种高纯度蛋黄卵磷脂的制备方法
WO2014042509A1 (fr) 2012-09-12 2014-03-20 Sime Darby Malaysia Berhad Extraction de lécithine à partir d'un déchet agro-industriel de palme

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