WO1998032449A1 - Procedimiento para extraer productos naturales mediante fluidos supercriticos - Google Patents
Procedimiento para extraer productos naturales mediante fluidos supercriticos Download PDFInfo
- Publication number
- WO1998032449A1 WO1998032449A1 PCT/ES1997/000015 ES9700015W WO9832449A1 WO 1998032449 A1 WO1998032449 A1 WO 1998032449A1 ES 9700015 W ES9700015 W ES 9700015W WO 9832449 A1 WO9832449 A1 WO 9832449A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- extraction
- organic products
- extracting organic
- products according
- procedure
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/02—Medicinal preparations containing materials or reaction products thereof with undetermined constitution from inanimate materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/56—Materials from animals other than mammals
- A61K35/60—Fish, e.g. seahorses; Fish eggs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/75—Rutaceae (Rue family)
- A61K36/752—Citrus, e.g. lime, orange or lemon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/906—Zingiberaceae (Ginger family)
- A61K36/9066—Curcuma, e.g. common turmeric, East Indian arrowroot or mango ginger
-
- 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
Definitions
- the present invention relates to a process for extracting organic products from plant or animal matrices, or their extracts, by high pressure extraction using conventional liquid solvents and in the presence of small amounts of supercritical fluids.
- JP 02235997 Preparation of algae aromas by extraction with supercritical or semi-critical carbon dioxide in the presence of water or alcohol
- US 4675198 Extraction of aromas from plant products using liquid or supercritical extractors
- JP 62036178 Extraction and separation of organic compounds from grape skins
- DE 2737794 Decaffeination of coffee by extraction with a solvent
- DE 2638383 Elimination of caffeine from coffee
- the process object of the present invention contemplates the maceration at pressures between 50 and 500 bar of the starting material in a solvent such as water, a hydrocarbon, an alcohol, a ketone, an ether, a carbon halide, or a mixture. of them, containing a supercritical fluid (FSC) in a proportion less than 50% of the total.
- a solvent such as water, a hydrocarbon, an alcohol, a ketone, an ether, a carbon halide, or a mixture. of them, containing a supercritical fluid (FSC) in a proportion less than 50% of the total.
- FSC supercritical fluid
- the high working pressure causes the penetrability of the FSC, as it decreases its viscosity and increases its diffusivity. This increase in diffusivity and decrease in viscosity facilitates the mobility of the FSC inside the cells and allows the extraction of substances much faster and with greater quantitative yields than in conventional extractions or in other existing extraction patents until moment.
- thermolabile products In addition to the extraction in an atmosphere that prevents oxidation, it is also carried out at such moderate temperatures, slightly higher than room temperature, that the risk of decomposition of thermolabile products is drastically reduced.
- the extraction mechanism is that the product extracted by the FSC is quickly solvated with the conventional solvent, establishing a balance between conventional solute-FSC-solvent that allows the
- the main solvent is not an FSC but it is ethanol, water or other solvents, which are those that are found in greater proportions, the FSC does not act as a solvent but acts as a transport vehicle between the plant matrix and the solvent
- extractions can be applied to the extraction of organic products such as essential oils, dyes, alkaloids, lipids, oils, waxes, proteins, fatty acids, aromas, spices, isoprenoids, steroids, carotenes, or pharmaceutical active ingredients, present in , or from, extracts of those provided by the technique, such as an oleoresin or an adsorbate, either present in, or from, biological matrices such as orange peel, paprika, grape skins, coffee, tea, plants Medicinal, seeds, carrot, or fish viscera.
- SUBSTITUTE SHEET (RULE 26) The time required to carry out this operation is generally between 0.5 and 5 hours.
- the product extracted and dissolved in the solvent is collected after depressurization and this technique can be combined with a separating stage that allows the extract to be recovered or fractionated. This recovery or fractionation can be carried out by any process offered by the technique.
- Example 1 Extraction of oleoresin from paprika. 140 g of paprika powder, 320 g of ethanol and 60 g of CO 2 are contacted for 30 minutes at 250 bar and 40 ° C. The extract is concentrated by evaporation in vacuo. 42 g of oleoresin are obtained.
- Example 2 Extraction of malvidin from the skins of the grapes. 100 g of grape skin, 280 g of ethanol and 150 g of CO 2 are contacted for 30 minutes at 150 bar and 80 ° C. The extract is concentrated by evaporation in vacuo. 125 mg of malvidin are obtained, approximately 70% of the total. This extract has a very aromatic character, which shows that the aromas present in the skin are also recovered during the extraction, i
- Example 3 Extraction of the essential oil, carotenes and flavonoids from the orange peel.
- 150 g of dried orange peel, 250 g of ethanol and 20 g of CO 2 are contacted for 30 minutes at 50 bar and 70 ° C.
- the extract is concentrated by evaporation in vacuo.
- 9 g of oleoresin are obtained, composed of the carotenes and flavonoids of the orange peel together with some pectins, free of degradation products, very aromatic and stable.
- Example 5 Extraction of pectins from orange albedo. 100 g of dry and finely ground albedo, 350 g of water acidified with nitric acid up to pH 2, and 40 g of CO 2 are contacted for one hour at 280 bar and 80 ° C. The extract is concentrated by evaporation under vacuum . To the residue after evaporation of water, ethanol is added, whereby 1.3 g of pectins precipitate.
- Example 6 Oil extraction from fishmeal. 200 g of fishmeal, 170 g of hexane, and 60 g of CO 2 are contacted for one hour at 250 bar and 50 ° C. The extract is concentrated by evaporation under vacuum. 13 g of oil are obtained.
- composition of this oil is: 6% in myristic acid, 19% in palmitic acid, 7% in palmitoleic acid, 19% in oleic acid, 8% in EPA, 8% in DHA, 12% in an unidentified fatty acid ( due to lack of standard), another 12% in another unidentified fatty acid (due to lack of standard), and the remaining 9% formed by miristoleic, pentadecanoic, stearic, heptadecanoic, linoleic and linolenic acids, in addition 1,209 ppm of vitamin A, 122 ppm of vitamin E, and small amounts of other vitamins.
- Example 7 Recovery of oil adsorbed by bleaching earth used in the refining of said oil. 200 g of one are contacted
- SUBSTITUTE SHEET (RULE 26) material whose composition is that of 76 g of adsorption land, 40 g of moisture, and 84 g of adsorbed olive oil, with 100 g of hexane and 40 g of C0 2 for 30 minutes at 280 bar and 40 ° C. extract is concentrated by evaporation in vacuo. 68 g of food grade olive oil are obtained.
- Example 8 Extraction of rosemary essential oil. 100 g of dehydrated rosemary, 200 g of hexane, and 60 g of CO 2 are contacted for 30 minutes at 150 bar and 40 ° C. The extract is concentrated by evaporation under vacuum. 5.7 g of oil are obtained.
- Example 9 Extraction of rosemary antioxidants. 100 g of dehydrated rosemary, 200 g of water, and 60 g of CO 2 are contacted for 30 minutes at 150 bar and 40 ° C. The extract is concentrated by evaporation under vacuum. 5.5 g of water-soluble extract are obtained.
- Example 10 Extraction of the essential oil and oleoresin from the rhizome of Turmeric longa. 125 g of Curcuma longa rhizome, 450 g of azeotropic ethanol, and 100 g of CO 2 are contacted for 30 minutes at 250 bar and 45 ° C. The extract is concentrated by evaporation under vacuum. 6.4 g of oleoresin are obtained, which contains 2.9 g of curcumin, equivalent to 46% of the curcumin present in the initial rhizome.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Botany (AREA)
- Alternative & Traditional Medicine (AREA)
- Cell Biology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developmental Biology & Embryology (AREA)
- Immunology (AREA)
- Virology (AREA)
- Zoology (AREA)
- Marine Sciences & Fisheries (AREA)
- Extraction Or Liquid Replacement (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES09600409A ES2103238B1 (es) | 1996-02-22 | 1996-02-22 | Procedimiento para extraer productos naturales a partir de matrices vegetales o animales mediante una extraccion a alta presion utilizando una mezcla de disolventes liquidos en presencia de fluidos supercriticos. |
PCT/ES1997/000015 WO1998032449A1 (es) | 1996-02-22 | 1997-01-28 | Procedimiento para extraer productos naturales mediante fluidos supercriticos |
DE69732031T DE69732031D1 (de) | 1997-01-28 | 1997-01-28 | Verfahren zur extraktion von naturstoffen mittels superkritischer fluide |
CA002250051A CA2250051A1 (en) | 1996-02-22 | 1997-01-28 | Procedure to extract natural products |
EP97903387A EP0917876B1 (en) | 1996-02-22 | 1997-01-28 | Process for extracting natural products by means of supercritical fluids |
AT97903387T ATE285242T1 (de) | 1997-01-28 | 1997-01-28 | Verfahren zur extraktion von naturstoffen mittels superkritischer fluide |
AU17959/97A AU1795997A (en) | 1996-02-22 | 1997-01-28 | Process for extracting natural products by means of supercritical fluids |
US09/154,030 US6326504B1 (en) | 1997-01-28 | 1998-09-16 | Procedure to extract natural products |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES09600409A ES2103238B1 (es) | 1996-02-22 | 1996-02-22 | Procedimiento para extraer productos naturales a partir de matrices vegetales o animales mediante una extraccion a alta presion utilizando una mezcla de disolventes liquidos en presencia de fluidos supercriticos. |
PCT/ES1997/000015 WO1998032449A1 (es) | 1996-02-22 | 1997-01-28 | Procedimiento para extraer productos naturales mediante fluidos supercriticos |
CA002250051A CA2250051A1 (en) | 1996-02-22 | 1997-01-28 | Procedure to extract natural products |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/154,030 Continuation-In-Part US6326504B1 (en) | 1997-01-28 | 1998-09-16 | Procedure to extract natural products |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998032449A1 true WO1998032449A1 (es) | 1998-07-30 |
Family
ID=8297787
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/ES1997/000015 WO1998032449A1 (es) | 1996-02-22 | 1997-01-28 | Procedimiento para extraer productos naturales mediante fluidos supercriticos |
Country Status (6)
Country | Link |
---|---|
US (1) | US6326504B1 (es) |
EP (1) | EP0917876B1 (es) |
AT (1) | ATE285242T1 (es) |
CA (1) | CA2250051A1 (es) |
DE (1) | DE69732031D1 (es) |
WO (1) | WO1998032449A1 (es) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2772561B1 (fr) | 1997-12-24 | 2000-12-29 | Aromes Et Parfums Franc | Utilisation de composes polyphenoliques ou de leurs derives comme capteurs de radicaux libres dans les filtres de cigarette |
FR2810672B1 (fr) * | 2000-06-22 | 2003-11-07 | Extractive | Procede de fractionnement d'huiles essentielles mettant en oeuvre au moins un solvant fluore |
US6576273B2 (en) * | 2000-08-24 | 2003-06-10 | Chr. Hansen A/S | Purification process for improving total yield of curcuminoid colouring agent |
KR100463232B1 (ko) * | 2001-10-12 | 2004-12-23 | 한국과학기술연구원 | 혼합유체를 이용한 성형물 중의 왁스류의 탈지방법 |
WO2004043163A2 (en) * | 2002-11-12 | 2004-05-27 | Water Solutions, Inc. | Process for extracting carotenoids from fruit and vegetable processing waste |
US7501141B2 (en) * | 2003-03-25 | 2009-03-10 | Council Of Scientific And Industrial Research | Process for the preparation of colorant from oleoresin |
US20060252949A1 (en) * | 2003-09-25 | 2006-11-09 | Lalit Chordia | Recovery of residual specialty oil |
ITAN20030053A1 (it) * | 2003-10-08 | 2005-04-09 | Mauro Angeletti | Processo per la produzione di estratto da semi d'uva a basso contenuto di polifenoli monomerici |
NZ545146A (en) * | 2006-02-07 | 2009-03-31 | Ind Res Ltd | Near-critical fluid fractionation process for extracting plant or animal material |
EP2010199A4 (en) * | 2006-03-17 | 2009-12-16 | Herbalscience Singapore Pte Ltd | EXTRACTS AND METHODS CONTAINING CURCUMA SPECIES |
FR2905284B1 (fr) * | 2006-08-29 | 2011-06-10 | Nat Invo | Procede d'extraction d'une substance d'un materiau. |
US20080233238A1 (en) * | 2007-02-08 | 2008-09-25 | Grimmway Enterprises, Inc. | Supercritical co2 carrot feedstock extraction |
CZ2008403A3 (cs) * | 2008-06-25 | 2010-03-31 | Ceská geologická služba | Metoda na získávání vápnitých nebo pyritizovaných fosílií z vápnitých hornin |
US8398857B2 (en) * | 2009-10-22 | 2013-03-19 | Epic Oil Extractors, Llc | Extraction of solute from solute-bearing material |
US8415506B2 (en) * | 2009-11-11 | 2013-04-09 | Dynasep Inc. | Energy efficient acetone drying method |
CN101905090B (zh) * | 2010-05-31 | 2012-08-15 | 中国农业大学 | 一种极性或中极性植物源天然产物提取的方法 |
US9908062B2 (en) | 2012-11-20 | 2018-03-06 | Andrew Paul Joseph | Extraction apparatus and method |
WO2014081881A2 (en) | 2012-11-20 | 2014-05-30 | Andrew Paul Joseph | Fluid-based extractor |
CN108288738B (zh) * | 2018-01-30 | 2021-03-23 | 常州大学 | 一种采用超临界二氧化碳流体回收锂离子电池电解液的方法 |
CN112843776A (zh) * | 2020-12-24 | 2021-05-28 | 常州市芙丽佳生物科技有限公司 | 一种橄榄仁提取物的提纯工艺 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0352667A1 (de) * | 1988-07-25 | 1990-01-31 | Siegfried Prof. Dr. Peter | Verfahren zur Herstellung von reinen Monoglyceriden und reinen Diglyceriden aus einem Gemisch, das Mono-, Di- und Triglyceride enthält |
DD294280A5 (de) * | 1990-05-11 | 1991-09-26 | Adw Institut Fuer Biotechnologie,De | Verfahren zur gewinnung von polyhydroxyfettsaeuren aus bakterienbiomasse |
US5210240A (en) * | 1984-08-09 | 1993-05-11 | Siegfried Peter | Process for the extraction of oil containing vegetable materials |
-
1997
- 1997-01-28 WO PCT/ES1997/000015 patent/WO1998032449A1/es active IP Right Grant
- 1997-01-28 DE DE69732031T patent/DE69732031D1/de not_active Expired - Fee Related
- 1997-01-28 CA CA002250051A patent/CA2250051A1/en not_active Abandoned
- 1997-01-28 EP EP97903387A patent/EP0917876B1/en not_active Expired - Lifetime
- 1997-01-28 AT AT97903387T patent/ATE285242T1/de not_active IP Right Cessation
-
1998
- 1998-09-16 US US09/154,030 patent/US6326504B1/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5210240A (en) * | 1984-08-09 | 1993-05-11 | Siegfried Peter | Process for the extraction of oil containing vegetable materials |
EP0352667A1 (de) * | 1988-07-25 | 1990-01-31 | Siegfried Prof. Dr. Peter | Verfahren zur Herstellung von reinen Monoglyceriden und reinen Diglyceriden aus einem Gemisch, das Mono-, Di- und Triglyceride enthält |
DD294280A5 (de) * | 1990-05-11 | 1991-09-26 | Adw Institut Fuer Biotechnologie,De | Verfahren zur gewinnung von polyhydroxyfettsaeuren aus bakterienbiomasse |
Also Published As
Publication number | Publication date |
---|---|
CA2250051A1 (en) | 1998-07-30 |
ATE285242T1 (de) | 2005-01-15 |
DE69732031D1 (de) | 2005-01-27 |
EP0917876A1 (en) | 1999-05-26 |
US6326504B1 (en) | 2001-12-04 |
EP0917876B1 (en) | 2004-12-22 |
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