WO1991014373A1 - Extraction et traitement des lipides, et produits ainsi obtenus - Google Patents

Extraction et traitement des lipides, et produits ainsi obtenus Download PDF

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Publication number
WO1991014373A1
WO1991014373A1 PCT/AU1991/000106 AU9100106W WO9114373A1 WO 1991014373 A1 WO1991014373 A1 WO 1991014373A1 AU 9100106 W AU9100106 W AU 9100106W WO 9114373 A1 WO9114373 A1 WO 9114373A1
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WO
WIPO (PCT)
Prior art keywords
process according
fluid
lipid
cream
subcritical
Prior art date
Application number
PCT/AU1991/000106
Other languages
English (en)
Inventor
Corran Norman Stuart Mclachlan
Gary Norris Kerkin
Peter Vines
Original Assignee
Portwall Pty Limited
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 Portwall Pty Limited filed Critical Portwall Pty Limited
Publication of WO1991014373A1 publication Critical patent/WO1991014373A1/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
    • A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
    • A23J1/20—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from milk, e.g. casein; from whey
    • A23J1/202—Casein or caseinates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C15/00—Butter; Butter preparations; Making thereof
    • A23C15/02—Making thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C7/00—Other dairy technology
    • A23C7/04—Removing unwanted substances other than lactose or milk proteins from milk
    • A23C7/043—Removing unwanted substances other than lactose or milk proteins from milk using chemicals in liquid or solid state, e.g. flocculating, adsorbing or extracting agents
    • 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
    • A23J1/00—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites
    • A23J1/20—Obtaining protein compositions for foodstuffs; Bulk opening of eggs and separation of yolks from whites from milk, e.g. casein; from whey
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0203—Solvent extraction of solids with a supercritical fluid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0403—Solvent extraction of solutions which are liquid with a supercritical fluid
    • B01D11/0407—Solvent extraction of solutions which are liquid with a supercritical fluid the supercritical fluid acting as solvent for the solute
    • 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
    • C11B3/006—Refining fats or fatty oils by extraction
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K5/00—Lactose

Definitions

  • This invention relates to the recovery of lipids from a lipid containing mixture, the processing, where necessary, of the so extracted lipids and the products so obtained.
  • the invention relates to a process for making butter.
  • Butter is a water-in-oil emulsion containing about 80 percent milk-fat and a maximum of sixteen percent water.
  • Milk-fat consists of a complex mixture of fatty acids and triglycerides with carbon numbers ranging from 4 to 56. In addition it contains many minor components, the major of which are cholesterol, mono- and di-glycerides and phospholipids. Their relative composition varies from animal to animal, seasonally, and on nutrient quality and type. In addition milk-fat contains vitamins A, D and carotene.
  • This invention is broadly concerned with a process for separating lipids from a lipid containing mixture which in the case of butter making removes the need for a churning step and optionally allows cholesterol to be removed, whilst still allowing the production of milk-fat at economical costs.
  • Quality requirements necessitate heating to 50-70°C for short times followed by cooling to 5 ⁇ C.
  • the fat content of the cream influences fat loss on churning.
  • Presence of bacteria affects product taste and storage properties.
  • Hydrolysis may be catalysed by natural milk lipases or introduced bacterial lipases.
  • the process of the invention is designed to achieve a good balance of the most desirable of these features.
  • Continuous butter-making processes documented in IDF Bulletin No. 204 include Fritz, Alfa, Alfa-Laval, New Way, Meleshin, Cherry Burrell and Creamery Package.
  • SUBSTITUTESHEET The process consists of a large variable speed churning cylinder, a big separating cylinder for separating the butter milk from the butter grains, a low-speed working section, a vacuum chamber and a second working chamber.
  • Fat losses occur during the separation of the buttermilk which may contain a residual fat content of 3-lOgm/l. This corresponds to 0.5-1.5 percent of the butter-fat leaving the plant. In addition approximately 40 percent of the phospholipids are lost in the buttermilk.
  • Supercritical fluids are found to be useful in removing undesirable components from food products or extracting desire material from a range of plant and animal materials.
  • a process for separating substantially all the lipids from a lipid-water mixture comprising bringing a subcritical or supercritical fluid at a suitable temperature and pressure and of a type such that at least part of the lipid is more soluble therein than water, into contact with the mixture, in an extractor under conditions so that at least part of the lipid component in the mixture is taken up by the fluid and then recovering the lipid from that fluid.
  • the invention is particularly concerned with the production of butter or butter-fat fractions.
  • the starting material for normal butter production namely cream, is an oil in water emulsion.
  • the invention will be described with reference to the production of butter from cream, but it is not to be considered as limited thereto. Concentrates prepared by removal of water from whole-milk according to the known art, may be used.
  • cream is separated from milk by centrifugation, according to the known art.
  • the volume of ⁇ ilk is reduced by a prior concentration step in which water is removed by reverse osmosis, or evaporation or the like.
  • concentration of milk-fat in the cream can be preferably anywhere from 10-80 percent and more preferably 20- 50 percent.
  • SUBSTITUTESHEET The concentration of milk-fat in the liquor to be subsequently extracted is not crucial to the success of the process but is largely determined from economic consideration regarding the size of the high pressure extraction equipment. Too high concentration of milk-fat in the cream may give rise, however, to unnecessary fat losses in the course of separation.
  • the temperature of the cream may be raised to 50-80°C, preferably 50-60°C, to ensure that a substantial reduction occurs in the risk of lypolysis due to the natural lipases, or introduced lipases, in the milk. Temperatures above 60°C are generally undesirable due to the possible damage to heat sensitive proteins in the milk.
  • the cream may then be passed through a degassing chamber to ensure that air or other gases are removed.
  • Degassing may tak place under vacuum and optionally with the injection of live steam at low temperature, or it may be effected by any process known to the art which is suitable and which does not raise th temperature of the cream above the limits described above. It is then fed directly to the carbon dioxide extraction apparatu or may be cooled to 5 ⁇ C-10°C for storage.
  • the cream is then heated or cooled, as the case may be, to the temperature of the extraction system by passing it through a heat exchanger, as known to the art, from which it is fed to the extraction column.
  • the amount of the lipid fraction that is extracted into the carbon dioxide fluid varies with the temperature of the extraction.
  • the carbon dioxide is in a supercritical state, substantially all of the lipid materials will be extracted into the supercritical fluid.
  • the temperature is below the critical temperature fractionation of the lipids
  • SUBSTITUTESHEET may occur as described in our NZ Patent Application, 236,285 (1990) and copending PCT application filed simultaneously herewith. The methods described in that specification may be incorporated in the processes of this invention.
  • the pressure and temperature conditions can be chosen so that the water solubility in carbon dioxide is maximised whilst lipases are completely or partially inactivated.
  • the differential density between the supercritical fluid and water can also be maximised within the above constraints to facilitate separation of any non-lipid components in the cream not dissolved.
  • the fluid is preferably carbon dioxide but 2 0, SF ⁇ , CF,C1, CF j Cl,, CH j CF- C 3 F o' r CHF 3' ethane, propane, butane, ethylene or acetone, which are considered unobjectionable from a health point of view can also be used. Mixtures of these fluids can be used. This invention will be further described with reference to the use of carbon dioxide alone.
  • the high pressure carbon dioxide that is used in the extraction column may be used alone or may contain an amount of water up to the amount which will saturate it under the particular conditions of temperature and pressure used in the extraction process. It is generally saturated when re-cycled in accordance with the process of this invention.
  • the conditions of temperature and pressure under which the extraction is effected may vary for reasons mentioned above depending upon the desired product.
  • the temperature at a minimum will be sufficient under the conditions of pressure employed to achieve sufficient dissolution of a desired fraction of the lipids. This will normally be above 0°C.
  • the maximum temperatures will be mainly determined by cost constraints and the desire to avoid damage to heat sensitive ingredients in the butter-fat or other desired product. The temperature will thus be between 0°C and 80°C.
  • the temperature will preferably be between -10°C and 31°C, more preferably 0°C to
  • the temperature will preferably be between 30°C and 80 C C, more preferably between
  • the pressure is generally between 75 bar and
  • Water has a relatively limited solubility in sub- or supercritical carbon dioxide which increases with temperature at constant pressure whereas carbon dioxide solubility for lipids decreases with temperature at constant pressure.
  • the carbon dioxide should intimately contact the surface of a thin film of the fat-in-water emulsion in a continuous co- current or counter-current manner.
  • the emulsion may be converted into the form of a thin film in any known manner as, for example, by passing the fat-in-water emulsion over a surface in the form of a thin film covering the same; by passing the emulsion through a cascade or packed bed, containing rings or other distribution systems known to the art, or a device which corresponds to a thin film surface evaporator or the like, or by spray nozzle or other droplet generating device.
  • the extraction may take plac in a liquid-fluid extraction involving plate mixer-settler units. It is not intended that the separation process be limited but is to follow process steps well recognised in the art of chemical engineers.
  • SUBSTITUTE SHEET water which acts as a scrubbing section.
  • the purpose of this "washing or scrubbing" is to remove any particulate matter entrained in the high pressure fluid and to extract any undesirable components extracted from the buttermilk with the fat that are preferentially soluble in water.
  • this water may be replaced by dilute milk-of-lime suspension or dilute sodium hydroxide solution, or any suitable alkaline solution.
  • the amount of carbon dioxide will be sufficient to dissolve the milk-fat and hence will be preferably 30-150 times the weight of milk-fat to be dissolved.
  • solubility of water in supercritical carbon dioxide is about 0.3 w/w percent - Wiebe R. & Gaddy V L, J. Am. Chem. Soc. 63,475 (1941) - whereas at 50°C and 75 bar it is 0.142 w/w percent and at 31°C and 75 bar it is about 0.09 w/w percent.
  • a recirculation ratio of about 80:1 (carbon dioxide: water) on a weight/weight basis is required. Under these conditions the ratio of fat to water in the carbon dioxide is between 2:1 and 10:1.
  • An important feature of the invention is to then reduce the cholesterol content in the lipid fraction in the high pressure fluid stream to produce a low-cholesterol product, preferably a cholesterol-free product.
  • the cholesterol can be removed by methods known in the art, such as using an adsorbent.
  • the adsorbent can be an inorganic compound or organic compound, which preferentially adsorbs cholesterol. There are many such adsorbents described in the literature. It is preferred within the scope of this invention, to use an adsorbent which selectively removes cholesterol and thus leaves behind a cholesterol free product and at the same time removes only a small amount if any, of the " lipid.
  • the preferred materials are
  • the invention also provides a method whereby the adsorbent ste can take place during the washing step.
  • the adsorbent ste can take place during the washing step.
  • milk of lime is used in the washing step in the column
  • calcium carbonate is formed during that process which is the most preferred adsorbent for use in this invention.
  • the calcium carbonate will precipitate and take with it cholesterol.
  • the amount of milk of lime added to the stream o high pressure carbon dioxide/lipid has to be calculated accurately in order to ensure that the solvent characteristics of the high pressure carbon dioxide for the lipid in the cream is not changed to such an extent that the lipid itself begins to precipitate out.
  • Cholesterol may be recovered from the adsorbent by any method known to the art and preferably by eluting it with a solvent which may be a subcritical or supercritical fluid optionally with the addition of a cosolvent. Such elution may take place in situ or otherwise.
  • the cholesterol-free or low-cholesterol product is then passed through depressurisation and heating cycles to recover it from the fluid.
  • the dissolved material may be recovered when the fluid is in the supercritical state through an increase in temperature at constant pressure or by lowering the temperatur and pressure but remaining supercritical or alternatively by reducing the temperature and pressure to subcritical conditions. When the fluid is in a subcritical state the product can be recovered by reducing the pressure and/or increasing the temperature.
  • the dissolved material may be recovered as a mixture of water and lipids or alternatively as
  • SUBSTITUTESHEET two separate phases, namely a fat-free aqueous phase and an essentially anhydrous lipid phase.
  • the recovered mixture of milk-fat, vitamins, water and phospholipids is then suitably degassed at 30-80°C, preferably 30-40 ⁇ C, and subsequently cooled to 15-20 ⁇ C by pumping it through a degassing chamber in which carbon dioxide and any residual off odours are removed.
  • Degassing may be effected by vacuum, or by nitrogen sparging into a vacuum or low pressure, or by any method known to the art.
  • the degassed milk ⁇ fat and water mixture is then fed to a wiped film heat exchanger or other device where it is worked to allow crystal growth and the production of butter according to the known art in butter or edible fat manufacture so as to prepare a product of the desired physical properties.
  • the degassed butter may be blended with other lipid fractions from that process to produce spreads with desired softening points, spreadability and other properties.
  • An important benefit of the invention is the fact that high pressure carbon dioxide is a highly effective bactericide, particularly when moist. Therefore it is possible in accordance with the invention to obtain sterile butter without the need for other micro-organism control methods such as pasteurisation or vacreation. As described above, however, it may be desirable to apply some form of degassing and heating to eliminate off-odour and inactivate lipases.
  • the invention has as its principal advantage the elimination of the butter churning step which in a normal butter operation causes fat losses. In the process of the invention, these losses can be reduced considerably and by suitable choice of processing conditions, eliminated almost completely.
  • step 1 cream is separated by a normal technique from whole milk; skim milk is the other product.
  • step 2 contact between the cream and high pressure carbon dioxide occurs.
  • Cream is fed into the top of the column, extraction vessel 1, with high pressure carbon -dioxide being fed countercurrent through the bottom.
  • the lipid/water/carbon dioxide stream is then fed to step 4, while the residue, namel water, solids-not-fat and undissolved lipids, is fed to step 3 where further separation of milk solids may be effected.
  • step 4 the lipid/water/carbon dioxide stream, still under high pressure conditions, is fed to the adsorbent columns.
  • adsorbent columns Preferably three of these are operating in parallel, so that at any one stage one can be on stand-by, another one is being use as the adsorbent while the third is being replenished by passage of a solvent therethrough.
  • the conditions of this process are more particularly described in our NZ Patent Application No. 221,503.
  • the carbon dioxide/water/lipid stream is subject to depressurisation so that the fat and water condenses in a condenser in step 6, while the carbon dioxide is fed back through step 7 (to change the temperature of the carbon dioxid to the appropriate value) and then through pump 8 to pressuris it to a suitable state.
  • step 6 The fat and water from step 6 are passed to a degasser in step 9, from which the carbon dioxide is returned to the recompression stage while the fat and water mix is fed to step 10 and 11 to form cholesterol-free butter. It is at this stag that lipid * fractions obtained by fractionation as mentioned
  • SUBSTITUTESHEET previously can be incorporated in various proportions to produce butter having a desired softening point and other desirable properties.
  • step 6 may be operated so that an aqueous phase and a lipid phase coexist in the condenser. These phases may be recovered separately, the lipid phase being essentially anhydrous milk fat.
  • the cholesterol from step 4 is eluted from the adsorbent by carbon dioxide and recovered after depressurisation.
  • the carbon dioxide is compressed and recycled.
  • a cosolvent may be added.
  • the two fluids were contacted at a temperature of 41°C, and a pressure of 250 bar. After contact the fat-rich carbon dioxide stream was passed to a separator where dissolved fat and water were removed. The carbon dioxide was recirculated.
  • the material recovered from the carbon dioxide was found to contain 81.4% fat, 18.4% moisture and 0.2% solids-not-fat.
  • SUBSTITUTESHEET separate phases existed in the ratio of 82% fat-rich, and 18% aqueous.
  • the fat-rich phase contained less than 1% moisture
  • the aqueous phase contained 1% total solids (0.16% fat, 0.84% solids-not-fat).
  • the residue not dissolved in the carbon dioxide was recovered and found to contain 90.2% moisture. 1.4% fat and 8.4% solids- not-fat.

Abstract

On décrit un procédé permettant de séparer pratiquement tous les lipides présents dans un liquide aqueux contenant des lipides. Il consiste à mettre ledit liquide en contact avec un fluide souscritique ou supercritique dans des conditions de température et de pression appropriées, telles qu'au moins une partie du lipide soit plus soluble dans le fluide que les autres constituants du liquide. De cette manière, certains lipides sont absorbés par le fluide, où ils sont ensuite récupérés. Le procédé peut être utilisé par exemple pour la préparation du beurre par l'extraction de la graisse de beurre dans la crème en utilisant le gaz carbonique supercritique.
PCT/AU1991/000106 1990-03-21 1991-03-21 Extraction et traitement des lipides, et produits ainsi obtenus WO1991014373A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
NZ233031 1990-03-21
NZ23033190 1990-03-21
NZ23449490 1990-07-13
NZ234494 1990-07-13
NZ236064 1990-11-13
NZ23606490 1990-11-13

Publications (1)

Publication Number Publication Date
WO1991014373A1 true WO1991014373A1 (fr) 1991-10-03

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Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/AU1991/000104 WO1991014377A1 (fr) 1990-03-21 1991-03-21 Traitement de melanges contenant des lipides et des proteines, et produits ainsi obtenus
PCT/AU1991/000106 WO1991014373A1 (fr) 1990-03-21 1991-03-21 Extraction et traitement des lipides, et produits ainsi obtenus

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/AU1991/000104 WO1991014377A1 (fr) 1990-03-21 1991-03-21 Traitement de melanges contenant des lipides et des proteines, et produits ainsi obtenus

Country Status (3)

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AU (3) AU7468191A (fr)
CS (2) CS76491A2 (fr)
WO (2) WO1991014377A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4306303A1 (de) * 1993-03-01 1994-09-08 Barth Raiser Hopfenextraktion Verfahren zur Gewinnung von pflanzlichen Ölen durch Extraktion
EP0719854A2 (fr) * 1994-12-29 1996-07-03 SKW Trostberg Aktiengesellschaft Procédé de fractionnement ou de raffinage de produits naturels lipidiques
US5728851A (en) * 1991-12-31 1998-03-17 University Research & Marketing Process for removing oil from dairy food products
FR2798863A1 (fr) * 1999-09-27 2001-03-30 Separex Sa Procede et installation de mise a l'etat adsorbe sur un support poreux de composes actifs contenus dans un produit
FR2811239A1 (fr) * 2000-07-07 2002-01-11 Extractive Procede d'extraction ou de fractionnement par fluide supercritique en presence d'un co-solvant incluant au moins un solvant fluore
WO2002049736A1 (fr) * 2000-12-18 2002-06-27 Ineos Fluor Holdings Limited Dispositif et procede servant a extraire une biomasse
GB2353735B (en) * 1999-09-06 2003-06-11 Ici Plc Apparatus and method for extracting biomass
US6589422B2 (en) 2000-12-18 2003-07-08 Ineos Fluor Holdings Limited Apparatus and method for extracting biomass
US8048304B2 (en) 2007-12-27 2011-11-01 Dynasep Llc Solvent extraction and recovery
CN101642632B (zh) * 2009-09-03 2012-05-30 江苏大学 天然产物有效成分的亚临界流体萃取装置与方法
US10144904B2 (en) 2015-12-04 2018-12-04 Evonik Degussa Gmbh Process for extraction of aroma chemicals from fat-containing and/or aqueous liquid phases

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5378487A (en) * 1993-03-17 1995-01-03 Kraft General Foods, Inc. Oil extraction of cholesterol from milk products
FR2799984B1 (fr) * 1999-10-21 2002-05-03 Lavipharm Procede de fractionnement d'une matiere composee de plusieurs constituants a l'aide d'un solvant a pression supercritique
NZ523920A (en) 2003-01-31 2005-11-25 Fonterra Co Operative Group Methods for extracting lipids from diary products using a near critical phase fluid
KR20070114108A (ko) 2004-10-12 2007-11-29 폰테라 코-오퍼레이티브 그룹 리미티드 β-시럼 유제품, 중성 지방이 격감되고/되거나 극성 지방이풍부한 유제품, 및 이들의 제조 방법
CN112485079B (zh) * 2020-11-02 2022-09-06 武汉金开瑞生物工程有限公司 一种脂肪组织蛋白提取试剂盒和提取方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1132836A (fr) * 1978-02-13 1982-10-05 Kurt Zosel Methode de decafeinisation directe des extraits aqueux de cafe
US4504503A (en) * 1981-09-09 1985-03-12 Lever Brothers Company Fractionation of butterfat using a liquefied gas or a gas in the supercritical state
US4692280A (en) * 1986-12-01 1987-09-08 The United States Of America As Represented By The Secretary Of Commerce Purification of fish oils
EP0321055A1 (fr) * 1987-12-16 1989-06-21 Unilever N.V. Procédé d'extraction de lactones de matière lipide et utilisation de l'extrait ainsi obtenu pour aromatiser des produits alimentaires

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1132836A (fr) * 1978-02-13 1982-10-05 Kurt Zosel Methode de decafeinisation directe des extraits aqueux de cafe
US4504503A (en) * 1981-09-09 1985-03-12 Lever Brothers Company Fractionation of butterfat using a liquefied gas or a gas in the supercritical state
US4692280A (en) * 1986-12-01 1987-09-08 The United States Of America As Represented By The Secretary Of Commerce Purification of fish oils
EP0321055A1 (fr) * 1987-12-16 1989-06-21 Unilever N.V. Procédé d'extraction de lactones de matière lipide et utilisation de l'extrait ainsi obtenu pour aromatiser des produits alimentaires

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5728851A (en) * 1991-12-31 1998-03-17 University Research & Marketing Process for removing oil from dairy food products
DE4306303A1 (de) * 1993-03-01 1994-09-08 Barth Raiser Hopfenextraktion Verfahren zur Gewinnung von pflanzlichen Ölen durch Extraktion
EP0719854A2 (fr) * 1994-12-29 1996-07-03 SKW Trostberg Aktiengesellschaft Procédé de fractionnement ou de raffinage de produits naturels lipidiques
EP0719854A3 (fr) * 1994-12-29 1997-10-22 Sueddeutsche Kalkstickstoff Procédé de fractionnement ou de raffinage de produits naturels lipidiques
GB2353735B (en) * 1999-09-06 2003-06-11 Ici Plc Apparatus and method for extracting biomass
WO2001023064A1 (fr) * 1999-09-27 2001-04-05 Separex (Societe Anonyme) Procede et installation de mise a l'etat adsorbe sur un support poreux de composes actifs contenus dans un produit
FR2798863A1 (fr) * 1999-09-27 2001-03-30 Separex Sa Procede et installation de mise a l'etat adsorbe sur un support poreux de composes actifs contenus dans un produit
US6709595B1 (en) 1999-09-27 2004-03-23 Separex (Societe Anonyme) Method and installation for setting in adsorbed state on a porous support active compounds contained in a product
FR2811239A1 (fr) * 2000-07-07 2002-01-11 Extractive Procede d'extraction ou de fractionnement par fluide supercritique en presence d'un co-solvant incluant au moins un solvant fluore
WO2002004085A1 (fr) * 2000-07-07 2002-01-17 Extractive Procede d"extraction ou de fractionnement par fluide supercritique en presence d"un co-solvant incluant au moins un solvant fluore
WO2002049736A1 (fr) * 2000-12-18 2002-06-27 Ineos Fluor Holdings Limited Dispositif et procede servant a extraire une biomasse
US6589422B2 (en) 2000-12-18 2003-07-08 Ineos Fluor Holdings Limited Apparatus and method for extracting biomass
US8048304B2 (en) 2007-12-27 2011-11-01 Dynasep Llc Solvent extraction and recovery
CN101642632B (zh) * 2009-09-03 2012-05-30 江苏大学 天然产物有效成分的亚临界流体萃取装置与方法
US10144904B2 (en) 2015-12-04 2018-12-04 Evonik Degussa Gmbh Process for extraction of aroma chemicals from fat-containing and/or aqueous liquid phases

Also Published As

Publication number Publication date
CS159391A2 (en) 1991-11-12
AU2040495A (en) 1995-08-10
AU7468191A (en) 1991-10-21
CS76491A2 (en) 1991-11-12
WO1991014377A1 (fr) 1991-10-03
AU7547691A (en) 1991-10-21

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