GB2288552A - Solvent extraction process - Google Patents

Solvent extraction process Download PDF

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Publication number
GB2288552A
GB2288552A GB9503875A GB9503875A GB2288552A GB 2288552 A GB2288552 A GB 2288552A GB 9503875 A GB9503875 A GB 9503875A GB 9503875 A GB9503875 A GB 9503875A GB 2288552 A GB2288552 A GB 2288552A
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United Kingdom
Prior art keywords
extraction
raw material
solvent
composition
present
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
GB9503875A
Other versions
GB9503875D0 (en
Inventor
Richard Llewellyn Powell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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
Priority claimed from GB9407743A external-priority patent/GB9407743D0/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB9503875A priority Critical patent/GB2288552A/en
Publication of GB9503875D0 publication Critical patent/GB9503875D0/en
Publication of GB2288552A publication Critical patent/GB2288552A/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • B01D11/0288—Applications, solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/10—Apiaceae or Umbelliferae [Carrot family], e.g. parsley, caraway, dill, lovage, fennel or snakebed
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/40—Liliopsida [monocotyledons]
    • A01N65/48—Zingiberaceae [Ginger family], e.g. ginger or galangal
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/11—Natural spices, flavouring agents or condiments; Extracts thereof obtained by solvent extraction

Abstract

A process for extracting a compound or composition of matter from a raw material containing that compound or composition as a constituent part is described. The process comprises the steps of (1) contacting a sample of the raw material with an extraction solvent comprising a (hydro)fluorocarbon ether, and (2) separating the solvent liquor thus obtained containing the extract from the raw material.

Description

SOLVENT EXTRACTION PROCESS The present invention relates to a solvent extraction process in which a raw material containing a particular compound or composition is treated with an extraction solvent so as to remove at least a proportion of that compound or composition from the raw material.
Processes for extracting a desired compound or composition from a raw or bulk material which contains that compound or composition as a constituent part using a suitable extraction solvent are known in the art. In these known processes, the raw material is contacted with the extraction solvent, often under vigorous mixing conditions so as to facilitate the dissolution of the desired compound or composition into the extraction solvent, and the resulting solvent liquor containing the desired compound or composition is then separated from the raw material for subsequent processing, e.g. distillation to remove the extraction solvent. Multiple extractions may suitably be carried out on the same raw material sample so as to maximise the amount of the desired compound or composition which is extracted from that sample. Typical examples of extraction solvents which have been used in the prior art extraction processes include hexane, methyl acetate, ethyl acetate, acetone and methanol.
Although solvent extraction processes are used on a commercial scale, the extraction solvents which are currently used in these processes are not wholly satisfactory. Thus, when solvents such as hexane are used to extract flavoured or aromatic oils, such as are used in the food and cosmetic industries, from plant matter containing those oils, unwanted materials contained in the plant, e.g. high molecular weight waxes, tend to be eluted along with the desired oil. This problem necessitates subjecting the resultant hexane liquor to further processing in which the unwanted waxes are removed by extraction, e.g. using ethanol. Furthermore, the extraction solvents which are currently in use have fairly high boiling points, and the elevated temperatures which are employed in the distillation process to remove these high boiling solvents from the extracted material can cause problems. For example, the flavoured or aromatic oils contained in certain plants are complex substances containing a large number of individual compounds some of which are relatively volatile or relatively thermally unstable. Consequently, high distillation temperatures can tend to result in a loss of product either through co-evaporation of the more volatile compounds with the extraction solvent or thermal degradation of the more thermally unstable compounds.
The present invention provides a new solvent extraction process which can be used to extract a wide variety of compounds or compositions from raw or bulk materials of which they form a constituent part. In one particular embodiment, the present invention provides a solvent extraction process which is capable of extracting the flavoured or aromatic oils contained in certain plant materials without eluting the high molecular waxes they contain.
According to the present invention there is provided a process for extracting a compound or composition of matter from a raw material containing that compound or composition as a constituent part, which process comprises the steps of (1) contacting a sample of the raw material with an extraction solvent comprising a (hydro)fluorocarbon ether, and (2) separating the solvent liquor thus obtained containing the extract from the raw material.
In one particular embodiment, the extraction process of the present invention can be used to extract a natural product, such as a flavoured or aromatic oil, from a plant material containing that product.
Accordingly, the present invention provides a process for extracting a natural product from a plant material containing that product as a constituent part, which process comprises the steps of (1) contacting a sample of the plant material with an extraction solvent comprising a (hydro)fluorocarbon ether, and (2) separating the solvent liquor thus obtained containing the extract from the plant material.
When used in this specification, the expression "plant material" not only includes materials which are essentially unprocessed and as such are clearly recognisable as being of plant origin, for example bark, leaves, flowers and seeds, but also materials, which although originating from plants, have been subjected to various processes and as such have a form which is somewhat different than the plants from which they originated, for example ground cumin and ground ginger.
In a further embodiment, the extraction process of the present invention can be used to extract a biologically active compound, such as a pesticide or a pharmaceutically active substance, or a precursor to such a compound from a raw material containing that compound or precursor, such as a plant material, a cell culture or a fermentation broth.
Accordingly, the present invention provides a process for extracting a composition comprising a biologically active compound or a precursor thereof from a raw material containing that composition as a constituent part, which process comprises the steps of (1) contacting a sample of the raw material with an extraction solvent comprising a (hydro)fluorocarbon ether, and (2) separating the solvent liquor thus obtained containing the extract from the raw material.
Suitable pesticides which may be extracted using the extraction process of the present invention include insecticides such as the pyrethroids.
Suitable pharmaceutically active substances which may be extracted using the extraction process of the present invention include the penicillins, the alkaloids, taxol, monensin and cytochalasin. Precursors to these compounds may also be extracted using the extraction process of the present invention. In one particular application for the extraction process of the present invention, taxol, which is an important anti-cancer drug, and/or taxane, which is a precursor to taxol, can be extracted from yew tree products, such as the bark or needles harvested from these trees.
According to a further aspect of the present invention, there is provided a composition comprising a pharmaceutically active substance obtained from a raw material product using the extraction process of the present invention.
According to a still further aspect of the present invention, there is provided a composition comprising a pharmaceutically active substance obtained from a raw material product using the extraction process of the present invention for use in medicine.
The present invention also provides a process for extracting a composition comprising one or more polar group containing compounds from a raw material containing that composition as a constituent part, such as a plant material, which process comprises the steps of (1) contacting a sample of the raw material with an extraction solvent comprising a (hydro)fluorocarbon ether, and (2) separating the solvent liquor thus obtained containing the extract from the raw material.
The extraction solvent which is used in the process of the present invention comprises a (hydro)fluorocarbon ether. Mixtures of two or more (hydro)fluorocarbon ethers may be used if desired. By the term (hydro)fluorocarbon ether we mean a compound selected from the group consisting of the hydrofluorocarbon ethers and the perfluorocarbon ethers.
(Hydro)fluorocarbon ethers having from 2 to 4 carbon atoms, especially the fluorine containing dialkyl ethers having this number of carbon atoms, are preferred, and of these the fluorine containing dimethyl ethers are particularly preferred. Examples of C24 (hydro)fluorocarbon ethers which may be useful in the extraction process of the present invention include, inter alia, bis(trifluoromethyl) ether (CF30CF3), trifluoromethyl difluoromethyl ether (CF30CF2H), pentafluoroethyl difluoromethyl ether (CF3CF2OCF2H), 1,1,1,2-tetrafluoroethyl trifluoromethyl ether (CF3CFHOCF3), trifluoromethyl fluoromethyl ether (CF30CFH2), bis(difluoromethyl) ether (CF2HOCF2H), pentafluoroethyl methyl ether (CF3CF2OCH3) and 1,1,2,2-tetrafluoroethyl trifluoromethyl ether (CF2HCF2OCF3).
The preferred (hydro)fluorocarbon ethers have a boiling point of 15"C or below, for example in the range of from -85 to 15C, preferably 0 C or below, for example in the range of from -85 to O"C, and more preferably -10 C or below, for example in the range of from -70 to -10 C.
In a preferred embodiment of the present invention, the extraction solvent which is used comprises a co-solvent in addition to the (hydro)fluorocarbon ether. Suitable co-solvents will typically have a boiling point of 60"C or below, for example in the range of from -85 to 60"C. The preferred co-solvents have a boiling point of 20"C or below, for example in the range of from -85 to 20"C, preferably 10 C or below, for example in the range of from -70 to 10 C, and more preferably 0 C or below, for example in the range of from -60 to 0 C. Mixtures of two or more co-solvents may be used if desired.
Suitable co-solvents may be selected from the C26, particularly the C24 hydrocarbon compounds which may be aliphatic or alicyclic.
Preferred hydrocarbons are the alkanes and cycloalkanes, with alkanes such as ethane, propane, n-butane and i-butane being especially preferred.
Other compounds which may be usefully employed as co-solvents in the extraction process of the present invention include the hydrocarbon ethers, particularly the dialkyl ethers, such as dimethyl ether, methyl ethyl ether and diethyl ether.
The extraction solvent preferably comprises from 50.0 to 99.5 % by weight, more preferably from 70.0 to 99.0 % by weight, and particularly preferably from 80.0 to 98.0 % by weight of the one or more (hydro)fluorocarbon ethers and from 50.0 to 0.5 % by weight, more preferably from 30.0 to 1.0 % by weight, and particularly preferably from 20.0 to 2.0 % by weight of the one or more co-solvents. If the co-solvent is a flammable material, which will be the case with the hydrocarbon and hydrocarbon ethers identified above, then the extraction solvent will preferably comprise sufficient of the (hydro)fluorocarbon ether to render it non-flammable overall. Where the extraction solvent is a blend of one or more (hydro)fluorocarbon ethers and one or more co-solvents, the resulting blend may be zeotropic, but is preferably azeotropic or azeotrope-like. Azeotropic and azeotrope-like blends are preferred, since they behave essentially as a single substance.
The extraction solvent which is used in the process of the present invention may be in liquid, gaseous or vaporous form, but is preferably in liquid form.
The raw material which is subjected to the present extraction process may be a liquid, e.g. a solution, suspension or emulsion, or a solid. If the raw material is a solid, then the efficiency of the extraction process may be significantly improved by reducing the solid to a finely divided form, such as a powder.
The.contacting of the extraction solvent with the raw material to be processed may be carried out under vigorous mixing conditions so as to facilitate the dissolution of the material to be extracted into the extraction solvent. The vigorous mixing may be achieved by mechanically shaking the extraction vessel containing the raw material/extraction solvent mixture or by stirring that mixture.
After the extraction process of the present invention has been completed, the solvent liquor containing the extract can be distilled to remove the extraction solvent from the extract. The resulting extract may then be used as it is or, alternatively, it may be subjected to one or more further processes, for example to purify the extract or to isolate a given compound or compounds contained in the extract.
In the preferred extraction process of the present invention, the extraction solvent which is used comprises a (hydro)fluorocarbon ether which has a relatively low boiling point compared to the extraction solvents used hitherto and, moreover, where a co-solvent is used this will likewise preferably have a relatively low boiling point. In consequence, once the extraction process of the present invention has been completed to yield a solvent liquor containing the extract, the removal of the extraction solvent from the liquor tends to be relatively facile allowing the distillation to be carried out at relatively low temperatures, e.g. room temperature and below. This in turn reduces the risk of losing desired product either through co-evaporation of the more volatile compounds with the extraction solvent or thermal degradation of the more thermally unstable compounds.
The extraction process of the present invention may be operated continuously with the same extraction solvent being used repeatedly.
A suitable installation for carrying out a continuous extraction process typically comprises an extraction vessel, a distillation unit, a compressor, a condenser and a suitable arrangement of connecting pipe work. The extraction solvent is first charged to the extraction vessel where it is contacted with the raw material to be processed, possibly under vigorous mixing conditions so as to facilitate the dissolution of the compound or composition to be extracted into the extraction solvent. The resulting solvent liquor containing the extract is then separated from the raw material, e.g.
by allowing the liquor to drain through a filter arranged at the bottom of the extraction vessel, and passed to the distillation unit where the extraction solvent is removed by evaporation to leave the extract. The vapour generated in the distillation unit is compressed, e.g. using a diaphragm compressor, and is then delivered to a condenser which returns the extraction solvent to liquid form for recharging to the extraction vessel. With a continuous extraction process of this kind, it is possible to maximise the amount of the extract obtained without subjecting the same raw material sample to a succession of individual extractions. Once the raw material sample is exhausted, it is then removed from the extraction vessel and replaced with a fresh raw material sample.

Claims (1)

  1. Claims:
    1. A process for extracting a compound or composition of matter from a raw material containing that compound or composition as a constituent part, which process comprises the steps of (1) contacting a sample of the raw material with an extraction solvent comprising a (hydro)fluorocarbon ether, and (2) separating the solvent liquor thus obtained containing the extract from the raw material.
GB9503875A 1994-04-19 1995-02-27 Solvent extraction process Withdrawn GB2288552A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB9503875A GB2288552A (en) 1994-04-19 1995-02-27 Solvent extraction process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9407743A GB9407743D0 (en) 1994-04-19 1994-04-19 Solvent extraction process
GB9503875A GB2288552A (en) 1994-04-19 1995-02-27 Solvent extraction process

Publications (2)

Publication Number Publication Date
GB9503875D0 GB9503875D0 (en) 1995-04-19
GB2288552A true GB2288552A (en) 1995-10-25

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2323544A (en) * 1997-03-25 1998-09-30 Robert Jeffrey Geddes Carr Extracting halocarbons
GB2324050A (en) * 1997-04-08 1998-10-14 Advanced Phytonics Ltd Extracting polar compounds
FR2771408A1 (en) * 1997-11-26 1999-05-28 Archimex Pibs Use of hydrofluoro ethers as solvents for organic molecules
WO2000072861A1 (en) * 1999-05-27 2000-12-07 Armadillo Pharmaceuticals, Inc. Pharmaceutical preparations of bioactive substances extracted from natural sources
GB2353727A (en) * 1999-09-06 2001-03-07 Ici Plc Apparatus and method for removing solvent residues
GB2353730A (en) * 1999-09-06 2001-03-07 Ici Plc Apparatus and method for extracting biomass
GB2353736A (en) * 1999-09-06 2001-03-07 Ici Plc Hydrofluorocarbon solvent recycling in biomass extraction.
FR2802547A1 (en) * 1999-12-21 2001-06-22 Archimex Pibs Extracting and fractionating fats comprises extraction using a fluorinated hydrocarbon solvent and a separation step
US6746695B1 (en) 1998-10-02 2004-06-08 Armadillo Pharmaceuticals, Inc. Pharmaceutical preparations of bioactive substances extracted from natural sources
AU775513B2 (en) * 1999-02-16 2004-08-05 Solvents Australia Pty Ltd Solvent extraction apparatus and process

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2323544A (en) * 1997-03-25 1998-09-30 Robert Jeffrey Geddes Carr Extracting halocarbons
GB2324050B (en) * 1997-04-08 2001-09-26 Advanced Phytonics Ltd Solvent extraction
GB2324050A (en) * 1997-04-08 1998-10-14 Advanced Phytonics Ltd Extracting polar compounds
US6649205B2 (en) 1997-04-08 2003-11-18 Advanced Phytonics Limited Solvent extraction
US6455087B1 (en) 1997-04-08 2002-09-24 Advanced Phytonics Limited Solvent extraction
FR2771408A1 (en) * 1997-11-26 1999-05-28 Archimex Pibs Use of hydrofluoro ethers as solvents for organic molecules
WO1999026903A1 (en) * 1997-11-26 1999-06-03 Extractive S.A. Method for extracting organic molecule(s) using a solvent medium containing a hydrofluoroether
US6746695B1 (en) 1998-10-02 2004-06-08 Armadillo Pharmaceuticals, Inc. Pharmaceutical preparations of bioactive substances extracted from natural sources
AU775513B2 (en) * 1999-02-16 2004-08-05 Solvents Australia Pty Ltd Solvent extraction apparatus and process
WO2000072861A1 (en) * 1999-05-27 2000-12-07 Armadillo Pharmaceuticals, Inc. Pharmaceutical preparations of bioactive substances extracted from natural sources
AU779928B2 (en) * 1999-05-27 2005-02-17 Michael Z. Martin Pharmaceutical preparations of bioactive substances extracted from natural sources
GB2353730B (en) * 1999-09-06 2001-11-14 Ici Plc Apparatus and method for extracting biomass
GB2353736B (en) * 1999-09-06 2001-07-18 Ici Plc A method and apparatus for recovering a solvent
GB2353727B (en) * 1999-09-06 2001-12-12 Ici Plc Apparatus and methods for removing solvent residues
US6667015B1 (en) 1999-09-06 2003-12-23 Ineos Fluor Holdings Limited Apparatus and method for extracting biomass
US6676838B2 (en) 1999-09-06 2004-01-13 Ineos Fluor Holdings Limited Apparatus and methods for removing solvent residues
US6710216B1 (en) 1999-09-06 2004-03-23 Imperial Chemical Industries Plc Method and apparatus for recovering a solvent
GB2353736A (en) * 1999-09-06 2001-03-07 Ici Plc Hydrofluorocarbon solvent recycling in biomass extraction.
GB2353730A (en) * 1999-09-06 2001-03-07 Ici Plc Apparatus and method for extracting biomass
GB2353727A (en) * 1999-09-06 2001-03-07 Ici Plc Apparatus and method for removing solvent residues
US7485207B2 (en) 1999-09-06 2009-02-03 Ineos Fluor Holdings Limited Method and apparatus for recovering a solvent
WO2001046354A1 (en) * 1999-12-21 2001-06-28 Extractive Method for extracting and fractionating fats with solvent, using at least a hydrofluroether
FR2802547A1 (en) * 1999-12-21 2001-06-22 Archimex Pibs Extracting and fractionating fats comprises extraction using a fluorinated hydrocarbon solvent and a separation step
US6673952B2 (en) 1999-12-21 2004-01-06 Extractive Method for extracting and fractionating fats with solvent, using at least a hydrofluroether

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Publication number Publication date
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