AU754139B2 - Method for extracting organic molecule(s) using a solvent medium containing a hydrofluoroether - Google Patents
Method for extracting organic molecule(s) using a solvent medium containing a hydrofluoroether Download PDFInfo
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- AU754139B2 AU754139B2 AU13412/99A AU1341299A AU754139B2 AU 754139 B2 AU754139 B2 AU 754139B2 AU 13412/99 A AU13412/99 A AU 13412/99A AU 1341299 A AU1341299 A AU 1341299A AU 754139 B2 AU754139 B2 AU 754139B2
- Authority
- AU
- Australia
- Prior art keywords
- solvent
- hydrofluoroether
- extraction
- extracts
- solvent medium
- 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.)
- Ceased
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- 239000002904 solvent Substances 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000006184 cosolvent Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000284 extract Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000000605 extraction Methods 0.000 description 21
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 10
- 239000002994 raw material Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000341 volatile oil Substances 0.000 description 6
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 244000178870 Lavandula angustifolia Species 0.000 description 2
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 241001393742 Simian endogenous retrovirus Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 244000073851 badasse Species 0.000 description 2
- 235000001053 badasse Nutrition 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000007803 cold maceration Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 238000007802 hot water maceration Methods 0.000 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- 235000018219 lavender Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- BUBOOZUTVJDNDE-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5-undecafluoro-5-propoxypentane Chemical compound CCCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BUBOOZUTVJDNDE-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DFUYAWQUODQGFF-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane Chemical compound CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)F DFUYAWQUODQGFF-UHFFFAOYSA-N 0.000 description 1
- 241001658031 Eris Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000005828 hydrofluoroalkanes Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
METHOD FOR EXTRACTING ORGANIC MOLECULE(S) USING A SOLVENT MEDIUM CONTAINING A HYDROFLUOROETHER The invention relates to the field of organic chemistry.
More precisely, the invention relates to a new method for solubilizing one or more organic molecules using a solvent medium containing a hydrofluoroether.
The invention finds application in particular in extraction, purifying, fractionating, separating, refining, depolluting, analysis operations, etc... These operations concern chiefly, but not exclusively, the aromatic, cosmetic, pharmaceutical, agribusiness, fine chemistry or environment-related industries.
The use of the solubilizing properties of some molecules is a well-known operation, in particular for the purpose of obtaining concentrated extracts. In this precise example, the extracts are conventionally obtained by contacting a given raw material with an extraction solvent such as hexane, acetone, ethanol.
This contacting may be conducted by hot or cold maceration, with or without shaking, by single or multiple extraction, for time intervals of varying lengths, etc... according to a unit protocol in separate batches or a continuous process. Other physical means may also be applied such as ultrasound or microwaves in 2 order to optimise extraction kinetics, yields or the quality of the extracts. On completion of the extraction, the exhausted raw material is separated from the solvent containing the solutes. The latter are concentrated by evaporation of the extraction solvent until a crude extract is obtained. The crude extract may undergo subsequent purification treatments such as, for example, desolvation. During the evaporation stage, the solutes undergo thermal stress which may lead to the denaturing of some of its constituents (onset of "roasted" notes, change in colour, loss of activity,...).
This degradation may be particularly extensive during the final desolvation of the extract, since industrial regulations lay down increasingly severe standards for residual solvent(s).
To these technical and regulatory restrictions must be added those imposed by consumers who demand products of increasingly higher purity, devoid of any toxicity yet having faultless organoleptic qualities.
New technologies have therefore been developed in order to substitute in full or in part those solvents having a certain extent of toxicity such as benzene, hexane or chlorinated products. Among these technologies, extraction using a gas in supercritical state has been the subject of numerous patent applications. By gas in the supercritical state is meant a gas which, when placed under special conditions of temperature and pressure, enters into an intermediate state between a liquid and a gas. On a phase diagram, this state is located beyond the critical point.
In known methods concerning this technique, the solvent gas may be carbon dioxide, alkanes or alkenes (butane, butene, propane, propene,...), chlorinated molecules such as chlorofluorocarbons (CFCs), etc...
either separately or in a mixture. For reasons of toxicity and safety, the solvent gas is most often carbon dioxide, whose critical point co-ordinates are 73 bars and 31.3 0 C. However, in most of the described methods, carbon dioxide is preferably subjected to a pressure of between 100 and 300 bars. The cost of the installations using supercritical methods is proportional to pressure constraints. These installations are therefore, by definition, extremely costly and rather more reserved up until now for products with high added value.
To reduce installation costs, several patent applications describe methods based on the principle of the refrigerating cycle in which the solvent gas of varying chemical nature is not in the supercritical state but simply liquefied under the action of pressure in the range of 2 to 25 bars.
Patent application EP 0 616 821 (on behalf of Wilde describes just such a method which generally uses non-chlorinated hydrofluoroalkanes as solvent gas and in particular 1,1,1,2-tetrafluoroethane. In this method, 1,1,1,2-tetrafluoroethane is liquefied under the action of a pressure of 6 bars and placed in contact with the raw material to be extracted. However, since 1,1,1,2tetrafluoroethane has limited solvent power, exhaustion of the raw material is conducted using multiplepercolation according to the well-known Soxhlet technique.
In order to remedy this constraint, patent GB 2 288 552 (Powell describes a method based on the same principle but which uses a hydrofluoroether as solvent gas instead of 1,1,1,2-tetrafluoroethane.
Hydrofluoroethers combine the qualities of 1,1,1,2tetrafluoroethane (safety, non-flammability, chemical inertia) with distinctly greater solvent power. However, in the described method, the hydrofluoroethers used are characterised by a number of carbon atoms lying between 18/09/2002 16: 56 +613-9890-1337 PATENT ATTORNEY SERV PAGE 03/08 4 2 and 4 and a boiling point eneray in the range of 'h s charac e t a eris 0 C and 15 0 C, Preferably between -70oC These characteristics require the use of specific equipment with which the solvent gas can be liquefied under pressure before and during extraction. For industrial application, this obligation becomes a nonnegligible financial restriction siice the industrialist must replace or considerably modify production tooling.
Finally, the use of hydrofluorocarbons (HFC) of I to 4 .0 carbons as extraction solvents is also to be noted, as described in WO 95/26794.
The purpose of the present invention is to put forward a new method for solubilizing or insolubilizing an Organic molecule or a group of organic molecules in a solvent or a mixture of solvents, which does not involve the above-cited disadvantages of the prior art.
In particular, one objective of the present invention is to describe said method which may be implemented using atmospheric pressure at room 20 temperature.
A further objective of the present invention is to disclose such a method which uses an atoxic solvent or mixture of solvents.
These different objectives are reached through the 25 invention which concerns a method using at least one solubilization step of an organic molecule or group of organic molecules in a solvent medium, characterised in that said solvent medium contains at least one hydrofluoroether chosen from the group made up of 30 methoxy-nonafluorobutane
(C
4
F
9
CH
3 and its isomer
S((C
3 ZCFCF2OCH 3 ethoxy-nonafluorobutane
(C
4 FrOC 2 Hs) and its isomer ((CF3) 2
CFCF
2
OC
2
H
5 and propoxyundecafluoropentane
(C
5
F
11 0C 3 1 7 said hydrofluoroether having a boiling point in atmospheric pressure ranging between +150C and +100°C.
18/09/2002 16:56 +613-9890-1337 PATENT ATTORNEY SERV PAGE 04/08 4a The method of the invention has the major advantage of bein: a::ble:^™ s ob e m aj or a d va nt a e of being able to be implemented under normal conditions of pressure and temperature, that is to say at atmospheric or near atmospheric pressure and at room or 0 near room temperature. Preferably, the method of the invention is implemented at room temperature and at atmospheric pressure.
Within the scope of the present invention, said hydrofluoroethers may be used pure or in a mixture. In addition to their high solvent power, they have the advantage of being non-toxic, chemically inert, nonflammable, colourless, odourless, tasteless. They also have low calorific capacity and low latent heat of vaporization. Finally, they also have the advantage of having zero Ozone Depletion Potential (ODP) and a low Global Warming Potential (GWP).
Also, preferably, said hydrofluoroether has a boiling point at atmospheric pressure in the range of +300C to +800C.
According to one variant of the invention, said solvent medium may, in addition to at least one hydrofluoroether, also contain at least one co-solvent.
By co-solvent is meant any molecule of any chemical nature whatsoever added in varying quantities to the hydrofluoroethers for the purpose of altering the properties of the mixture obtained (solvent power,...).
According to the present invention, the preferred cosolvents have the lowest toxicity possible. By way of example, that is in no way restrictive, ethanol and water are considered to be co-solvents within the scope of the present invention.
The present invention may be implemented in particular to obtain extracts of superior quality from a raw material, and/or to purify and/or fractionate such extracts under normal conditions of pressure and temperature.
When the method of the invention is used to obtain extracts of superior quality from a raw material, the method of obtaining these new extracts conforms to the prior art: placing the hydrofluoroether(s), whether or not containing one or more co-solvents, in contact with a determined raw material by hot or cold maceration, with or without shaking, by single or multiple extraction, for time intervals of varying lengths, etc...
Other physical means may also be used such as ultrasound or microwaves in order to optimise the extraction kinetics, yields or the quality of the extracts.
The exhausted raw material after extraction is separated from the solvent containing the solutes. The latter are concentrated by evaporation of the hydrofluoroether(s) until the extract is obtained. Given the physico-chemical characteristics of hydrofluoroethers, it is not necessary to apply any special pressure before or during extraction. Extraction is therefore conducted under atmospheric pressure. This characteristic of the invention is of importance since it allows substitution of conventionally used extraction solvents by hydrofluoroethers without requiring any change to existing industrial tooling.
The extracts obtained are characterised by: no toxicity caused by extraction solvents, low residual solvent content, high purity and low production costs while complying with the most restrictive environmental standards. This last characteristic of the extracts obtained can be accounted for by the absence of any need for changes to production tooling and easy hydrofluoroether regeneration.
The method of the invention may also be used to purify and/or fractionate extracts obtained with a conventional extraction method in order to remove, or at least substantially reduce, the concentration of one or more undesired molecules in the extract. By way of example of such molecules, that is in no way restrictive, mention may be made of the extraction solvents used in conventional methods and pesticides.
The hydrofluoroether(s) containing one or more undesired molecules are separated from the extract by simple sedimentation, filtration or azeotropic separation.
Given the physico-chemical characteristics of the hydrofluoroethers of the present invention, it is not necessary to apply any special pressure either before or during purifying and/or fractionating. It is therefore conducted at atmospheric pressure. In addition, all the purification and/or fractionating steps are conducted at a temperature of below 800C, preferably--at room temperature.
The refined extracts obtained show no or a greatly reduced number of undesired molecules, low residual solvent content, high purity, intactness of the "noble" constituents of the extract (no thermal degradation), low production costs while conforming to the most restrictive environmental standards.
The invention also covers any extract or any purified extract which may be obtained by using the method of the invention. Such extracts may in particular be aromatic extracts, active ingredients, colouring extracts, etc...
The invention and the various advantages it offers will be more easily understood on reading the following description of four non-restrictive examples of embodiment.
Example 1: 100 g of lavendula hybrida flowers crushed and dried (dry matter 85 are placed in contact with 2 litres of methoxy-nonafluorobutane (C 4
F
9 0CH 3 The mixture is brought to 45 0 C and shaken for 5 hours. After solid/liquid separation, the filtrate is evaporated in a vacuum (250 mbar, 48 0 An extract weighing 13.16 grams is collected which has the aromatic notes characteristic of hybrid lavender.
Example 2: 30 grams of whole dried flowers of lavendula hybrida and 250 g of methoxy-nonafluorobutane
(C
4
F
9 0CH 3 )are added to a mixing grinder of Warring Blender type in order to crush the flowers directly in contact with the solvent. After grinding for 30 seconds at 22 0 C the flowers are separated from the solvent by filtration and rinsed twice in 15 ml of fresh solvent.
The lavender residue is replaced in contact with the same quantity of fresh solvent and re-extracted under the same conditions. Overall, 5 successive extractions are made. Each filtrate is evaporated separately. The extracts obtained are weighed and the results given in the table below.
Grinding/extractio 1 2 3 4 n Mass of extract 1.72 0.67 0.58 0.58 0.13 The global yield of the 5 extraction tests is 12.27 The total mass of extract obtained is 3.68 g. The first extract obtained is in the form of a limpid slightly yellow-coloured oil. It has a strong smell and has the aromatic notes that are characteristic of hybrid lavender flowers.
Example 3: An emulsion water model is reconstituted by emulsifying 1 by mass of essential oil of lavender (obtained by conventional hydrodistillation) in demineralised water. The emulsion obtained has a milky appearance characteristic of emulsion waters. 170 grams of this solution are placed in contact with quantities of methoxy-nonafluorobutane (C 4
F
9
OCH
3 in accordance with a methoxy-nonafluorobutane/emulsion ratio of 0.01, 0.02, 0.1 and 0.2 relative to the emulsion. After homogenisation and sedimentation, the methoxynonafluorobutane containing the essential oil is drawn off and evaporated in a vacuum (250 mbars, 48° 0 C) An additional test is made conducting 3 successive washings of the model in accordance with a global ratio of 0.3.
The table below gives the percentages of essential oil extracted from the model in relation to the ratio and expressed relative to the initial quantity of essential oil in the model.
Ratio 0.01 0.02 0.1 0.2 0.3* essential oil 38.5 44.4 67.5 72.7 83.1 extracted result obtained for 3 washings The best result is obtained with a ratio (methoxynonafluorobutane/model) of 0.3 with 3 successive washings. In this case, 83 of the emulsified essential oil is extracted with methoxy-nonafluorobutane.
Example 4: A model of food oil to undergo de-solvation is reconstituted by incorporating 150 ppm of hexane in commercial soybean oil. The exact content of hexane in the oil is determined using the IUPAC 2 607 method by head space in gaseous phase chromatography.
It is desired to solubilize the residual hexane in the methoxy-nonafluorobutane and to collect the solution obtained by simple sedimentation. The methoxynonafluorobutane is incorporated into the model according to a (methoxy-nonafluorobutane/residual hexane) ratio of 5. After homogenisation and sedimentation for one hour at room temperature (250C), oil samples are taken to analyse the hexane content. The results obtained show that 23.5 of the hexane initially present is extracted from the oil by methoxynonafluorobutane in a single extraction.
The above-described examples of the invention are not intended to limit the scope of the invention. In this respect, it will be noted that the invention may be implemented under any method requiring the solubilization of a molecule or a group of molecules in a solvent.
Claims (5)
- 2. Method according to claim I, wherein said hydrofluoroether has a boiling point at atmospheric pressure in the range of +30C to +8 p o n t a t a t mo s p h er i c
- 3. Method according to either of claims 1 or 2, wherein said solvent medium includes at least one co-solvent.
- 4. Method according to claim 3, wherein said co-solvent is chosen from the group made up of ethanol and water. Method according to any one of claims 1 to 4, wherein method is implemented at room temperature.
- 6. Method according to any one of claims 1 to 5, wherein said method is implemented at atmospheric pressure.
- 7. Method substantially as hereinbefore described with reference to Examples 1 to 4. 25 Dated this 18th day of September 2002 PATENT ATTORNEY SERVICES Attorneys for EXTRACTIVE S.A. o
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9715114A FR2771408B1 (en) | 1997-11-26 | 1997-11-26 | METHOD FOR SOLUBILIZING ORGANIC MOLECULE (S) USING A SOLVENT MEDIUM CONTAINING A HYDROFLUOROETHER |
| FR97/15114 | 1997-11-26 | ||
| PCT/FR1998/002546 WO1999026903A1 (en) | 1997-11-26 | 1998-11-26 | Method for extracting organic molecule(s) using a solvent medium containing a hydrofluoroether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1341299A AU1341299A (en) | 1999-06-15 |
| AU754139B2 true AU754139B2 (en) | 2002-11-07 |
Family
ID=9514024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU13412/99A Ceased AU754139B2 (en) | 1997-11-26 | 1998-11-26 | Method for extracting organic molecule(s) using a solvent medium containing a hydrofluoroether |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1034155A1 (en) |
| JP (1) | JP2001524369A (en) |
| AU (1) | AU754139B2 (en) |
| BG (1) | BG104549A (en) |
| CA (1) | CA2311782A1 (en) |
| FR (1) | FR2771408B1 (en) |
| IL (1) | IL136970A0 (en) |
| WO (1) | WO1999026903A1 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2255413A1 (en) | 1998-12-11 | 2000-06-11 | Fracmaster Ltd. | Foamed nitrogen in liquid co2 for fracturing |
| WO2000065018A1 (en) * | 1999-04-26 | 2000-11-02 | 3M Innovative Properties Company | Stabilized carbon dioxide fluid composition and use thereof |
| FR2802547B1 (en) * | 1999-12-21 | 2002-03-01 | Archimex Pibs | PROCESS FOR THE EXTRACTION AND FRACTIONATION OF FATS BY SOLVENT, USING AT LEAST ONE HYDROFLUOROETHER |
| FR2810672B1 (en) * | 2000-06-22 | 2003-11-07 | Extractive | PROCESS FOR THE FRACTIONATION OF ESSENTIAL OILS USING AT LEAST ONE FLUOROUS SOLVENT |
| JP2006089543A (en) * | 2004-09-22 | 2006-04-06 | Shiseido Co Ltd | Method for producing natural perfume |
| FR2910470B1 (en) * | 2006-12-22 | 2009-02-27 | Armement Et D Etudes Alsetex S | LACRYMOGENIC COMPOSITION, PROCESS FOR PREPARING SUCH A COMPOSITION, AND NON - FLAMMABLE DEFENSE DEVICE COMPRISING SUCH A COMPOSITION. |
| CN106267902B (en) * | 2007-06-04 | 2019-08-20 | 高压生物科学公司 | Molecular stress-enhanced extraction and distribution |
| JP5481270B2 (en) * | 2010-05-07 | 2014-04-23 | Ｊｘ日鉱日石エネルギー株式会社 | Method for reducing sulfur compounds in hydrocarbon oils |
| CN102965198A (en) * | 2012-11-14 | 2013-03-13 | 陈和平 | Method for extracting and processing lavender essential oil |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2276392B (en) * | 1993-02-22 | 1997-03-26 | D G P | Improved production of natural flavours and fragrances |
| GB9406423D0 (en) * | 1994-03-31 | 1994-05-25 | Ici Plc | Solvent extraction process |
| GB2288552A (en) * | 1994-04-19 | 1995-10-25 | Ici Plc | Solvent extraction process |
| CA2219233A1 (en) * | 1995-05-16 | 1996-11-21 | Dean S. Milbrath | Azeotrope-like compositions and their use |
| US5814595A (en) * | 1995-05-16 | 1998-09-29 | Minnesota Mining And Manufacturing Company | Azeotrope-like compositions and their use |
| US5827446A (en) * | 1996-01-31 | 1998-10-27 | E. I. Du Pont De Nemours And Company | Nonafluoromethoxybutane compositions |
-
1997
- 1997-11-26 FR FR9715114A patent/FR2771408B1/en not_active Expired - Fee Related
-
1998
- 1998-11-26 JP JP2000522064A patent/JP2001524369A/en active Pending
- 1998-11-26 CA CA002311782A patent/CA2311782A1/en not_active Abandoned
- 1998-11-26 WO PCT/FR1998/002546 patent/WO1999026903A1/en not_active Ceased
- 1998-11-26 EP EP98956965A patent/EP1034155A1/en not_active Withdrawn
- 1998-11-26 AU AU13412/99A patent/AU754139B2/en not_active Ceased
- 1998-11-26 IL IL13697098A patent/IL136970A0/en unknown
-
2000
- 2000-06-20 BG BG104549A patent/BG104549A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1034155A1 (en) | 2000-09-13 |
| FR2771408B1 (en) | 2000-04-14 |
| AU1341299A (en) | 1999-06-15 |
| FR2771408A1 (en) | 1999-05-28 |
| BG104549A (en) | 2001-08-31 |
| CA2311782A1 (en) | 1999-06-03 |
| IL136970A0 (en) | 2001-06-14 |
| WO1999026903A1 (en) | 1999-06-03 |
| JP2001524369A (en) | 2001-12-04 |
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