EP1835014B1 - Extraction d'huile utilisant des esters alkyliques d'acides gras - Google Patents

Extraction d'huile utilisant des esters alkyliques d'acides gras Download PDF

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Publication number
EP1835014B1
EP1835014B1 EP20060290413 EP06290413A EP1835014B1 EP 1835014 B1 EP1835014 B1 EP 1835014B1 EP 20060290413 EP20060290413 EP 20060290413 EP 06290413 A EP06290413 A EP 06290413A EP 1835014 B1 EP1835014 B1 EP 1835014B1
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Prior art keywords
fatty acid
seed
ester
oil
triglyceride
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EP1835014A1 (fr
Inventor
Chih-Chung Chou
Kohsin Chien
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Oilseeds Biorefinery Corp
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Oilseeds Biorefinery Corp
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Priority to EP20060290413 priority Critical patent/EP1835014B1/fr
Priority to PT62904131T priority patent/PT1835014E/pt
Priority to ES06290413.1T priority patent/ES2540910T3/es
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    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting

Definitions

  • Oil has been routinely recovered from oil-bearing plants for thousands of years. A large variety of plants produce sufficient quantities of oil that can be processed into edible or industrial products.
  • Oil from oil-bearing plants is typically extracted by solvents.
  • Solvent extraction is a mass-transfer process in which one or more materials are transported from a mixture to a solvent phase, resulting in their separation from the mixture.
  • Various organic solvents have been used for commercial extraction.
  • This invention is based on the discovery that a triglyceride can be readily extracted from an oil-bearing seed by using a fatty acid alkyl ester which is obtained by reacting alcohol with a triglyceride that is identical to the triglyceride extracted from the triglyceride-containing part of the oil-bearing plant as a solvent.
  • this invention features a method of producing a triglyceride solution.
  • the method includes contacting a liquid fatty acid alkyl ester and a substance containing triglyceride (e.g., at 15-180°C or 25-150°C) so that the triglyceride is dissolved into the fatty acid alkyl ester to form a triglyceride solution.
  • the fatty acid alkyl ester is obtained, prior to the contacting step, by reacting alcohol (e.g. a C1-C8 primary or secondary alcohol) with triglyceride extracted from the same triglyceride-containing part of the oil-bearing plant.
  • alcohol e.g. a C1-C8 primary or secondary alcohol
  • Exemplary alcohols include methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-pentanol, isopentanol, neopentanol and n-hexanol.
  • the fatty acid alkyl ester and the triglyceride-containing part of the oil-bearing plant can be mixed at a weight ratio ranging from 1:2 to 10:1 (e.g., from 1:1 to 6:1).
  • the triglyceride-containing oil-bearing plant can be oil-bearing seed.
  • oil-bearing seed refers to any plant seed suitable for oil extraction.
  • oil-bearing seed include, but are not limited to, soybean, peanut, sunflower seed, rapeseed, corn (e.g., corn germs or distillers dried corn grains), jatropha seed, karanja seed, neem seed, mahua seed, castor bean, rubber seed, cotton seed, palm kernel, olive, almond kernel, babassu seed, ben seed, cardoon seed, camelina seed, linseed, hazelnut kernel, hemp seed, mustard seed (e.g., Ethiopian mustard seed and Indian mustard seed), jojoba seed, poppy seed, safflower seed, sesame seed, wheat grain, sal seed, crambe seed, cuphea seed, nahor seed, and tobacco seed.
  • mustard seed e.g., Ethiopian mustard seed and Indian mustard seed
  • jojoba seed
  • the triglyceride-containing substance can be obtained from parts other than seed in certain oil-bearing plants.
  • oil-bearing plant refers to any plant that contains oil in any part (e.g., seed or fruit) and is suitable for oil extraction. Examples in addition to those listed above include, but are not limited to, rice bran, palm (e.g., palm fruit pulp), yellowwood, and algae.
  • the fatty acid alkyl ester described above can contain a C1-C8 primary or secondary alkoxy moiety or a C6-C24 fatty acid moiety.
  • fatty acid mentioned herein refers to a straight or branched, saturated or unsaturated monobasic organic acid.
  • Exemplary fatty acids include, but are not limited to, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachidic acid, behenic acid, lignoceric acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, cis-11-eicosenoic acid, and erucic acid.
  • Exemplary fatty acid alkyl esters include, but are not limited to, fatty acid methyl esters, fatty acid ethyl esters, fatty acid n-propyl esters, fatty acid isopropyl esters, fatty acid n-butyl esters, fatty acid isobutyl esters, fatty acid n-pentyl esters, fatty acid isopentyl esters, fatty acid neopentyl esters, and fatty acid n-hexyl esters.
  • the fatty acid alkyl ester can have a boiling point of 150-500°C.
  • Erskine discloses a method for extracting a compound from a plant material, the extractant including a fatty acid ester.
  • the method consists in contacting Echium Planatagineum with fatty acid esters to extract a mixture of fatty acids containing stearidonic acid. This method produces a stearidonic acid solution.
  • Echium Planatagineum is an example of an oil bearing plant with characteristically high content of a particular fatty acid ( WO 02/092779 ).
  • Koslowsky (US 4,004,041 ) teaches the use of palm fatty acid esters in dissolving the palm glycerides.
  • Ikehara et al. (EP 1491204 ) teaches the use of an oil and fat composition containing 10% by weight or more of a specific fat-soluble polyhydric fatty acid ester, in particular, a glycerol fatty acid ester, as a solvent for extracting hydrophobic components (i.e., flavonoids), which are not triglycerides, from licorice.
  • This invention relates to extracting a triglyceride from an oil-bearing plant using a fatty acid alkyl ester which is obtained by reacting alcohol with a triglyceride that is identical to the triglyceride extracted from the triglyceride-containing part of the oil-bearing plant as a solvent at a certain temperature (e.g., 15-180°C) to obtain an extraction solution.
  • a fatty acid alkyl ester which is obtained by reacting alcohol with a triglyceride that is identical to the triglyceride extracted from the triglyceride-containing part of the oil-bearing plant as a solvent at a certain temperature (e.g., 15-180°C) to obtain an extraction solution.
  • a certain temperature e.g. 15-180°C
  • the extraction process can be performed by methods well known in the art. As an example, it can be carried out by mixing a pulverized oil-bearing plant and a fatty acid alkyl ester in a continuous stirred-tank reactor for a predetermined period of time. As another example, it can be carried out continuously by bring together, without mixing, a pulverized oil-bearing plant and a fatty acid alkyl ester in a plug flow reactor or a fixed bed reactor through a counter-current flow, a co-current flow, or a combination of both flows.
  • the extraction process can be carried out by either a batch method or a flow method. Typically, a flow method can be used to help maintain reasonable manufacturing costs.
  • the extraction can be performed at different temperatures. Generally, extraction at a higher temperature (e.g., above 35°C) recovers more oil. However, high temperature extraction may also produce more impurities (e.g., phosphorus and moisture).
  • the weight ratio between the solvent and the oil-bearing plant used in the extraction process depends on various factors, e.g., the type of the oil-bearing plant and the oil content in the oil-bearing plant. For example, one can use a low weight ratio for extracting a prepressed oil-bearing plant, from which a portion of the oil in the plant has been removed. Typically, the weight ratio is in the range of 1:2 to 10:1. Other extraction conditions (e.g., the extraction time) can be determined empirically.
  • the fatty acid alkyl ester used in the extraction process can be prepared by known methods.
  • a fatty acid alkyl ester can be prepared by an esterification reaction between an alcohol (e.g., ethanol) and a fatty acid (e.g., stearic acid).
  • a fatty acid alkyl ester can be prepared by a transeterification reaction between an alcohol and a triglyceride, such as the transeterification reactions described in U.S. Patent Application 10/945,339 .
  • the fatty acid alkyl ester is prepared from a C1-C4 alcohol.
  • Extractions with such a fatty acid alkyl ester generally produce a triglyceride solution that contains less impurities (e.g., phosphorus and moisture).
  • the triglyceride used to prepare the fatty acid alkyl ester is obtained from a plant that is the same as the plant to be extracted.
  • the triglyceride extracted from the plant is identical to the triglyceride used to prepare the extraction solvent (i.e., the fatty acid alkyl ester).
  • the fatty acid alkyl ester in an extraction solution can be used as a solvent for the reaction and therefore needs not to be separated from the extracted triglyceride.
  • the fatty acid alkyl ester can be optionally separated from the extracted triglyceride by partially or completely removal from an extraction solution.
  • the removal step can be carried out by distillation using a vacuum column, a short-path vacuum distillation unit, or any other suitable device known in the art. Whether to remove the fatty acid alkyl ester partially or completely from an extraction solution or to remove it at all depends on various factors, such as the ratio between the fatty acid alkyl ester and the extracted triglyceride and the end use of the extracted triglyceride.
  • the extracted triglyceride can be further processed for use in the food and pharmaceutical industries. It can also be used as a raw material for preparing fatty acid alkyl esters or fatty alcohols.
  • Fatty acid alkyl esters are useful as diesel fuels, lubricant oils, or chemical intermediates.
  • Fatty alcohols are useful as surfactants in detergent industry.
  • Soybeans were first ground into a powder and sieved through a filter having a size of 40 mesh (about 425-520 ⁇ m). Soybean powder having an average particle size of less than 40 mesh, which is similar to a dehulled powder, was collected and used for oil extraction.
  • soybean powder obtained above was dried until it had a moisture content of less than 6 wt%.
  • the powder was then extracted using soybean based fatty acid methyl esters (FAMEs) as a solvent in a beaker with agitation.
  • FAMEs soybean based fatty acid methyl esters
  • the soybean based FAMEs were previously prepared by a transesterification reaction between methanol and triglycerides obtained from soybean.
  • the extraction process was carried out by using FAMEs at a solvent-to-powder weight ratio of 6:1 at 35°C.
  • the beaker was agitated at a revolution per minute (rpm) of 300.
  • the content of the miscella i.e., the solution containing extracted oil
  • the oil content in the miscella was determined by HPLC (JASCO model 1580; column: Luna Su C18, 2 ⁇ m, 250*4.6 mm, Phenomenex, Torrance, CA; mobile phases: methanol, and hexane/isopropyl alcohol (4:5); UV detector: UV-2075, JASCO Inc., Tokyo, Japan).
  • the moisture content in the miscella was determined by the Karl-Fisher method according to the operation manual, MKC-500 KF Moisture Titrator Kyoto Electronic Manufacturing Co. Ltd, Ver. 04, #595-0006.
  • the phosphorus content in the miscella was determined according to American Oil Chemist's Society official method Ca 12-55. The results showed that miscella contained a moisture content of 818 ppm, a phosphorus content of 14.4 ppm, and an oil content of 3.60 wt%.
  • the weight of the extracted oil was 20% of that of the soybean powder.
  • the soybean powder was also successively extracted with FAMEs at a reduced solvent-to-powder ratio in a beaker. Specifically, the powder was extracted twice at a solvent-to-powder ratio of 1: 1 by agitating the beaker at a rpm of 1,000 for 15 mintues. After the first extraction, the miscella contained a moisture content of 989 ppm, a phosphorus content of 23.4 ppm, and an oil content of 14.08 wt%. After the second extraction, the miscella contained a moisture content of 1,428.3 ppm, a phosphorus content of 14.23 ppm, and an oil content of 6.13 wt%. After two extractions, the total weight of the extracted oil was 21.59% of that of the soybean powder.
  • the soybean powder obtained above was also extracted via a conventional method. Specifically, the powder was extracted by Gerhardt's Soxtherm automated soxlet system using hexane as a solvent at a solvent-to-powder ratio of 8:1 at 65°C. This method is described in Official and Tentative Methods, the American Oil Chemist Society, Vol. 1, AOCS Champaign II (1980) Method Am 2-93 . The results show that the oil contained a phosphorus content of 265 ppm. The weight of the extracted oil was 18.8% of that of the soybean powder.
  • FAMEs Two types of oil-bearing seeds were extracted by FAMEs prepared from triglycerides obtained from their corresponding oil sources. Specifically, sunflower seeds were extracted by sunflower seed based FAMEs and peanuts (ground nuts) were extracted by peanut based FAMEs.
  • Sunflower seeds were dehulled and ground into a powder having an average particle size of less than 40 mesh. The powder was dried until it had a moisture content of less than 6 wt%. It was then extracted twice in a beaker with sunflower seed based FAME at a solvent-to-powder ratio of 1:1. Each extraction was conducted by agitating the beaker at a rpm of 1,000 for 15 minutes at 35°C. After the first and second extractions, the miscella contained a moisture content of 794 and 831 ppm, respectively, a phosphorus content of 49.6 and 47.8 ppm, respectively, and an oil content of 35.65 and 12.30 wt%, respectively. After two extractions, the total weight of the extracted oil was 54.83% of that of the sunflower seeds.
  • Peanuts were ground into a powder having an average particle size of less than 25 mesh (i.e., about 425-710 ⁇ m) and then dried until it contained less than 6 wt% of moisture. The powder was then extracted four times in a beaker with peanut based FAMEs at a solvent-to-powder ratio of 1:1. Each extraction was conducted by agitating the beaker at a rpm of 1,000 for 15 minutes at 35°C.
  • the miscella contained a moisture content of 701, 690, 661, and 661 ppm, respectively, a phosphorus content of 23.5, 16.4, 0, and 0 ppm, respectively, and an oil content of 31.4, 10.9, 2.63, and 0.78 wt%, respectively.
  • the total weight of the extracted oil was 45.83% of that of the peanuts.
  • the total weight of the extracted oil was 47.48% of that of the peanuts.
  • Soybeans were extracted by soybean based fatty acid ethyl esters (FAEEs). Soybean based FAEEs were prepared by a transesterification reaction between ethanol and triglycerides obtained from soybeans.
  • Soybeans were first ground into a powder having an average particle size of less than 40 mesh and then dried until it had a moisture content of less than 6 wt%. The powder was then extracted three times in a beaker with soybean based FAEEs at a solvent-to-powder ratio of 1: 1. Each extraction was conducted by agitating the beaker at a rpm of 1000 for 15 minutes at 35°C. After the first, second, and third extractions, the miscella contained a moisture content of 650, 652, and 694 ppm, respectively, a phosphorus content of 39.4, 23.3, 16.0 ppm, respectively, and an oil content of 14.09, 5.93, and 1.05 wt%, respectively. After three extractions, the total weight of the extracted oil was 20.1 % of that of the soybean powder.
  • Soybeans were extracted by a method similar to that described in Example 3 except that soybean based fatty acid butyl esters (FABEs) were used as a solvent. Soybean based FABEs were prepared by a transesterification reaction between n-butanol and triglycerides obtained from soybeans.
  • FABEs soybean based fatty acid butyl esters
  • the miscella contained a moisture content of 576, 519, and 479 ppm, respectively, a phosphorus content of 27.32,13.49, and 0.96 ppm, respectively, and an oil content of 15.93, 5.10, and 1.60 wt%, respectively. After three extractions, the total weight of the extracted oil was 21.6% of that of the soybean powder.
  • Soybeans were extracted by a method similar to that described in Example 4 except that the extractions were conducted at a reduced agitation rate, i.e., at a rpm of 500. Further, the extractions were conducted at four different temperatures, i.e., 35°C, 60°C, 100°C, and 150°C.
  • the results show that the total weight of the extracted oil increased at higher temperatures. Specifically, at 35°C, 60°C, 100°C, and 150°C, the total weights of the extracted oil were respectively 21.42, 23.25, 28.4, and 32.8% of those of soybean powder. The results also show that at 35°C, 60°C, 100°C, and 150°C, the phosphorus contents in a mixture containing a combination of miscella obtained after each extraction were 16.2, 18.64, 48.32, and 91.12 ppm, respectively.
  • Two oil-bearing seeds were extracted by FAMEs prepared from triglycerides obtained from their corresponding oil sources and triglycerides obtained from another oil source. Specifically, sunflower seeds were extracted by sunflower seed based FAMEs and soybean based FAMEs, and peanuts (ground nuts) were extracted by peanut based FAMEs and soybean based FAMEs.
  • Sunflower seeds were extracted with sunflower seed based FAMEs and soybean based FAMEs using a method similar to that described in Example 2 except that a solvent-to-powder ratio of 6:1 was used and that only one extraction was performed.
  • the miscella contained a moisture content of 466 and 856 ppm, respectively, a phosphorus content of 10.6 and 12.78 ppm, respectively, and an oil content of 6.33 and 4.06 wt%, respectively.
  • the total weight of the extracted oil was 39.0% of that of the sunflower seeds when sunflower seed based FAMEs were used as the solvent and 24.71% of that of the sunflower seeds when soybean based FAMEs were used as the solvent.
  • Peanuts were extracted with peanut based FAMEs and soybean based FAMEs using a method similar to that described in Example 2 except that the solvent-to-powder ratio was 6:1 and that only one extraction was performed.
  • the miscella contained a moisture content of 470 and 718 ppm, respectively, a phosphorus content of 19.36 and 10.0 ppm, respectively, and an oil content of 6.23 and 6.83 wt%, respectively.
  • the total weight of the extracted oil was 39.1% of that of the peanuts when peanut based FAMEs were used as the solvent and 39.8% of that of the peanuts when soybean based FAMEs were used as the solvent.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Claims (29)

  1. Procédé de production d'une solution de triglycéride, comprenant la mise en contact d'une partie d'une plante oléagineuse contenant un triglycéride avec un ester alkylique d'acide gras liquide qui est obtenu en faisant réagir un alcool avec un triglycéride qui est identique au triglycéride extrait de la partie contenant un triglycéride de la plante oléagineuse, de sorte que le triglycéride soit dissous dans l'ester alkylique d'acide gras pour former une solution de triglycéride.
  2. Procédé selon la revendication 1, dans lequel la plante oléagineuse est du son de riz, de la pulpe de fruit de palmier, du podo ou des algues.
  3. Procédé selon la revendication 1, dans lequel la partie contenant un triglycéride de la plante oléagineuse est une graine oléagineuse.
  4. Procédé selon la revendication 3, dans lequel la graine oléagineuse est le soja, l'arachide, la graine de tournesol, la graine de colza, le maïs, la graine de jatropha, la graine de karanja, la graine de margousier, la graine de mahua, la graine de ricin, la graine d'hévéa, la graine de coton, l'amande de palmiste, l'olive, l'amande, la graine de babassu, la graine de Moringa oleifera, la graine de cardon, la graine de caméline, la graine de lin, la noisette, la graine de chènevis, la graine de moutarde, la graine de jojoba, la graine de pavot, la graine de carthame, la graine de sésame, la graine de blé, la graine de sal, la graine de crambe, la graine de cuphéa, la graine de nahor ou la graine de tabac.
  5. Procédé selon la revendication 1, dans lequel l'ester alkylique d'acide gras contient une fraction acide en C6 à C24.
  6. Procédé selon la revendication 1, dans lequel l'ester alkylique d'acide gras contient une fraction alcoxy primaire ou secondaire en C1 à C8.
  7. Procédé selon la revendication 1, dans lequel l'ester alkylique d'acide gras est un ester méthylique d'acide gras, un ester éthylique d'acide gras, un ester n-propylique d'acide gras, un ester isopropylique d'acide gras, un ester n-butylique d'acide gras, un ester isobutylique d'acide gras, un ester n-pentylique d'acide gras, un ester isopentylique d'acide gras, un ester néopentylique d'acide gras ou un ester n-hexylique d'acide gras.
  8. Procédé selon la revendication 1, dans lequel l'ester alkylique d'acide gras a un point d'ébullition de 150 à 500° C.
  9. Procédé selon la revendication 1, dans lequel l'étape de mise en contact est réalisée à 15 à 180° C.
  10. Procédé selon la revendication 9, dans lequel l'étape de mise en contact est réalisée à 25 à 150° C.
  11. Procédé selon la revendication 1, dans lequel l'ester alkylique d'acide gras et la partie contenant un triglycéride de la plante oléagineuse sont mis en contact à un rapport en poids allant de 1 : 2 à 10 : 1.
  12. Procédé selon la revendication 1, dans lequel l'ester alkylique d'acide gras est obtenu, avant l'étape de mise en contact, en faisant réagir de l'alcool avec un triglycéride extrait de la même partie contenant un triglycéride de la plante oléagineuse.
  13. Procédé selon la revendication 12, dans lequel la plante oléagineuse est du son de riz, de la pulpe de fruit de palmier, du podo ou des algues.
  14. Procédé selon la revendication 12, dans lequel la partie contenant un triglycéride de la plante oléagineuse est une graine oléagineuse.
  15. Procédé selon la revendication 14, dans lequel la graine oléagineuse est le soja, l'arachide, la graine de tournesol, la graine de colza, le maïs, la graine de jatropha, la graine de karanja, la graine de margousier, la graine de mahua, la graine de ricin, la graine d'hévéa, la graine de coton, l'amande de palmiste, l'olive, l'amande, la graine de babassu, la graine de Moringa oleifera, la graine de cardon, la graine de caméline, la graine de lin, la noisette, la graine de chènevis, la graine de moutarde, la graine de jojoba, la graine de pavot, la graine de carthame, la graine de sésame, la graine de blé, la graine de sal, la graine de crambe, la graine de cuphéa, la graine de nahor ou la graine de tabac.
  16. Procédé selon la revendication 15, dans lequel l'ester alkylique d'acide gras contient une fraction acide en C6 à C24.
  17. Procédé selon la revendication 16, dans lequel l'alcool est un alcool primaire ou secondaire en C1 à C8.
  18. Procédé selon la revendication 17, dans lequel l'ester alkylique d'acide gras est un ester méthylique d'acide gras, un ester éthylique d'acide gras, un ester n-propylique d'acide gras, un ester isopropylique d'acide gras, un ester n-butylique d'acide gras, un ester isobutylique d'acide gras, un ester n-pentylique d'acide gras, un ester isopentylique d'acide gras, un ester néopentylique d'acide gras ou un ester n-hexylique d'acide gras.
  19. Procédé selon la revendication 18, dans lequel l'ester alkylique d'acide gras et la partie contenant un triglycéride de la plante oléagineuse sont mis en contact à un rapport en poids allant de 1 : 2 à 10 : 1.
  20. Procédé selon la revendication 19, dans lequel l'étape de mise en contact est réalisée à 15 à 180° C.
  21. Procédé selon la revendication 20, dans lequel l'étape de mise en contact est réalisée à 25 à 150° C.
  22. Procédé selon la revendication 12, dans lequel l'ester alkylique d'acide gras contient une fraction acide en C6 à C24.
  23. Procédé selon la revendication 12, dans lequel l'alcool est un alcool primaire ou secondaire en C1 à C8.
  24. Procédé selon la revendication 12, dans lequel l'ester alkylique d'acide gras est un ester méthylique d'acide gras, un ester éthylique d'acide gras, un ester n-propylique d'acide gras, un ester isopropylique d'acide gras, un ester n-butylique d'acide gras, un ester isobutylique d'acide gras, un ester n-pentylique d'acide gras, un ester isopentylique d'acide gras, un ester néopentylique d'acide gras ou un ester n-hexylique d'acide gras.
  25. Procédé selon la revendication 12, dans lequel l'ester alkylique d'acide gras a un point d'ébullition de 150 à 500° C.
  26. Procédé selon la revendication 12, dans lequel l'étape de mise en contact est réalisée à 15 à 180° C.
  27. Procédé selon la revendication 12, dans lequel l'étape de mise en contact est réalisée à 25 à 150° C.
  28. Procédé selon la revendication 12, dans lequel l'ester alkylique d'acide gras et la partie contenant un triglycéride de la plante oléagineuse sont mis en contact à un rapport en poids allant de 1 : 2 à 10 : 1.
  29. Procédé selon la revendication 1, dans lequel l'alcool est un alcool primaire ou secondaire en C1 à C8.
EP20060290413 2006-03-14 2006-03-14 Extraction d'huile utilisant des esters alkyliques d'acides gras Not-in-force EP1835014B1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP20060290413 EP1835014B1 (fr) 2006-03-14 2006-03-14 Extraction d'huile utilisant des esters alkyliques d'acides gras
PT62904131T PT1835014E (pt) 2006-03-14 2006-03-14 Extracção de óleo utilizando ésteres de alquilo de ácidos gordos
ES06290413.1T ES2540910T3 (es) 2006-03-14 2006-03-14 Extracción de aceite usando ésteres alquílicos de ácidos grasos

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EP1835014B1 true EP1835014B1 (fr) 2015-04-22

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002092779A2 (fr) * 2001-05-17 2002-11-21 Pilot Therapeutics, Inc. Procede d'enrichissement de tissus dans des acides gras polyinsatures a chaine longue

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