Classifications

• • 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
  • C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
• • 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
• • 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
  • C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B3/00—Refining fats or fatty oils
  • C11B3/006—Refining fats or fatty oils by extraction
• • C—CHEMISTRY; METALLURGY
  • 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
  • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
  • C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
  • C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
  • Y02W30/00—Technologies for solid waste management
  • Y02W30/50—Reuse, recycling or recovery technologies
  • Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

Definitions

• the invention relates to the field of extraction chemistry. More specifically, the present invention relates to the extraction of fats from natural raw materials.
• Fats mainly those of vegetable origin, are ingredients widely used by the food, cosmetic and pharmaceutical industries.
• fats enriched with unsaponifiable matter that is to say, according to French standard NFT 60-205-1 in substances which, after saponification of the fat by potash and extraction by a specified solvent, are not volatile under specified conditions.
• Fats enriched in unsaponifiables have particularly high contents of hydrocarbons, heavy alcohols (aliphatic or terpene), sterols and tocopherols and are obtained after elimination of part of the triglycerides which are the main constituents of crude fat.
• solvent extraction is a very widespread technique which is available according to numerous technological variants.
• patent application FR 2 702 773 proposes a process for the preparation of vegetable fat fractions enriched with unsaponifiable matter.
• the vegetable fat is treated with acetone in order to recover, on the one hand, a hot insoluble fraction, rich in unsaponifiable matter, and, on the other hand, a soluble fraction, subjected subsequently to a step of cold crystallization.
• the filtrate is evaporated to dryness.
• the evaporation residue also constitutes a fraction enriched with unsaponifiable matter.
• the precipitate on the other hand, is enriched in triglycerides. It will be noted that, depending on the raw material from which they are extracted, vegetable fats have different compositions, qualitatively and quantitatively.
• the main objective of the present invention is to provide a method for extracting and fractionating fat by solvent which does not have such drawbacks.
• a method according to the invention is characterized in that it comprises at least one step using an extraction solvent consisting of at least one hydrofluroether (abbreviated to HFE) of general formula (I): n ⁇ 2n + ⁇ m H 2m + 1 in which, n is between 3 and 6 and m is between 1 and 5 and at least one separation step leading to the obtaining of a part of a crude extract of matter fatty rich in unsaponifiable substances and, possibly, in free fatty acids and on the other hand to an insoluble fraction of extraction.
• HFE hydrofluroether
• hydrofluoroethers have, compared to conventional solvents, the following advantages compared to conventional solvents. They are non-flammable and do not therefore require the use of special production and protection equipment. This characteristic is particularly interesting in production prospects on an industrial scale since it has a direct impact on the cost of finished products;
• said hydrofluoroether is chosen from methoxynonafluorobutane of formula C 4 F 9 -O-CH 3 (also designated in the chemical industry by the name HFE7100) and ethoxynonafluorobutane C 4 F 9 -OC H 5 (also designated in the chemical industry by the name HFE-7200).
• hydrofluoroethers can also be used in extraction processes using new technologies such as microwaves or ultrasound. It will be noted that the use of hydrofluoroethers as extraction agents has already been described in PCT patent application FR98 / 02546. This document discloses the solubilizing nature of HFEs for the preparation of plant extracts without, however, highlighting, unlike the present invention, the particularly selective character of these HFEs with respect to the particular classes of chemical compounds that are the rich lipid fractions. in unsaponifiable matter.
• the present invention demonstrates that the HFEs are capable of extracting, with good selectivity, such lipid fractions rich in unsaponifiable matter. It will be noted that this selectivity is not total since the HFEs of formula (I) co-extract lipid substances which do not belong to the category of unsaponifiable matters, in particular triglycerides and free fatty acids. The coextraction of free fatty acids constitutes in some cases an additional advantage of the process, particularly in the case of matrices containing free fatty acids of pharmaceutical, cosmetic or nutritional interest.
• the method according to the invention therefore makes it possible to fractionate the fat into fractions enriched in unsaponifiable matter and in free fatty acids and in fractions enriched in triglycerides.
• the method comprises an additional step consisting in decanting said filtrate and then evaporating it so as to recover a soluble extract very enriched in unsaponifiable substances and in free fatty acids.
• said insoluble fraction is recycled at the start of the process.
• the method according to the invention can be implemented in the presence of at least one co-solvent chosen from alkanes, ketones, alcohols, alkyl ethers, carboxylic acids, esters, amides , halogenated hydrocarbons, acetals.
• Example 1 Fractionation of shea butter into a fraction enriched in triglycerides and a fraction enriched in unsaponifiable shea butter (20 g), titrated at 7-8% unsaponifiable, is stirred at 40 ° C. for
• This example is intended to provide an element of comparison with regard to the extraction yields with hexane and the extraction yields with ethoxy nonafl uorobutane.
• Cocoa cake (50 g) is extracted in a Soxhlet for 5 hours with hexane. After extraction, the hexane extract is evaporated and the extract yield is calculated on the basis of the weight of cake used.
• Cocoa cakes (50 g) are extracted in Soxhlet for 5 hours with ethoxynonafluorobutane (C 4 F 9 -OC 2 H 5 ). After extraction, the extract is cooled to room temperature (20 ° C). This operation makes it possible to decant an insoluble fraction. After elimination of the insoluble fraction, the fluorinated under-swimming is evaporated. The yields of insolubilized extract and of soluble extract are calculated on the basis of the weight of oil cakes used.
• Cocoa cake (500 g) is extracted with stirring, at 65 ° C, for 1H3O, with 2 liters (2.86 kg) of ethoxynonafluorobutane (C 4 F 9 -OC 2 H 5 ).
• the suspension is quickly filtered on a 10 ⁇ m mesh filter cloth.
• the filtrate is cooled to 20 ° C. in order to precipitate an insoluble material as in Example 2.
• the insoluble material is filtered through a filter fabric of 10 ⁇ m mesh.
• the intermediate yield in insoluble fraction is calculated on the basis of the weight of oil cakes used.
• the filtrate obtained is returned to the extractor for a new extraction cycle using the insoluble material from the previous extraction. In total, four extraction cycles are carried out according to the same operating mode.
• the final filtrate (separated from the insoluble material precipitated at 20 ° C) is evaporated under reduced pressure.
• the yield of soluble materials is expressed relative to the weight of oil cakes used. The results are specified in Table 3 below.
• the extracts insolubilized at 20 ° C are yellow in color.
• the soluble extract is lighter with a strong cocoa odor.
• the qualitative analysis of the fractions is carried out by thin layer chromatography (silica) using an eluent hexane / ethyl ether / acetic acid 90/10/1.
• the deposits correspond to 6 ⁇ l of hexane solutions at 20 mg / ml.
• the plates are dried and then revealed with ethanol at 5% sulfuric acid (drying at 110 ° C).
• the results indicate that the insolubilized extracts are enriched in triglycerides and that the soluble matters of the final filtrate are on the other hand enriched in unsaponifiable matters. A much higher content of free fatty acids is also observed in the soluble materials of the final filtrate than in the insolubilized extracts.
• the fractionation by hydrofluoroethers can be applied to many other fats or natural matrices known for their lipid profile as well as for their uses for mainly cosmetic, pharmaceutical or food purposes (in particular avocado, wheat germ oil, oil pumpkin and pumpkin seeds, savv palmeto fruits (Serenoa repens), bark of Pygeum africanum (Prunus africana).
• the invention may also be applied to animal raw materials, raw materials of animal origin (milk and derivatives, egg products, lanolin, beeswax, etc.) as well as single-celled organisms (yeasts, fungi, bacteria).
• This example describes the influence of various operating parameters on the fractionation of shea butter by ethoxynonafluorobutane (HFE7200). These parameters are the extraction temperature, the extract reprocessing temperature and the number of extraction cycles carried out on the same charge of shea butter 50 g of shea butter (titrating 6.5% unsaponifiable) are extracted by 2 liters of ethoxynonafluorobutane with gentle stirring for 30 minutes and at the extraction temperature T E (50 or 70 ° C). After decantation, the two-phase medium is separated into a crude extract (EB1) and a raffinate.
• EB1 crude extract
• the raffinate is subjected twice more to the same extraction operating procedure, making it possible to obtain two other crude extracts (EB2 and EB3).
• the three crude extracts (EB 1, EB2 and EB3) are stored overnight at a precipitation temperature T p (4 ° C or room temperature) in order to cause the precipitation of part of the triglycerides and, thus, to increase the unsaponifiable content of fluorinated extracts.
• T p 4 ° C or room temperature
• the indicators making it possible to evaluate the influence of the three operating parameters are the mass of the soluble extracts ESI, ES2 and ES3, the unsaponifiable content of the soluble extracts ESI, ES2 and ES3, the mass of unsaponifiable extract, present in the ESI extracts , ES2 and ES3, and the mass of the precipitated extracts EPI, EP2 and EP3. Table 4 below shows the influence of these three operating parameters.
• the amount of soluble extract depends only on the precipitation temperature. It increases with T p and decreases with each extraction cycle.
• the unsaponifiable content only depends on the precipitation temperature. It increases when T p decreases and it decreases with each extraction cycle, the mass of extractable unsaponifiable matter remains approximately constant, whatever the extraction and precipitation temperatures. It decreases with each extraction cycle, the quantity of precipitated extract only depends on the extraction temperature. It increases with T E and also remains constant whatever the extraction cycle.
• the critical parameter is therefore the precipitation temperature: "for a low precipitation temperature (ex: 4 ° C), the extraction will be selective
• Example 4 showed that the extraction temperature had no significant influence on either the selectivity or the efficiency of the extraction. Consequently, in this example, the shea butter is treated at an extraction temperature of 50 ° C., just above its liquefaction temperature.
• the extraction procedure is identical to that of Example 4, except for the precipitation temperatures: -18 ° C, 4 ° C and room temperature.
• the extraction will be effective (high quantity of soluble extract) but not very selective (average unsaponifiable content).

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Wood Science & Technology (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Chemistry (AREA)
• Analytical Chemistry (AREA)
• Microbiology (AREA)
• Fats And Perfumes (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Extraction Or Liquid Replacement (AREA)
• Cosmetics (AREA)

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• 1999
  • 1999-12-21 FR FR9916196A patent/FR2802547B1/fr not_active Expired - Fee Related
• 2000
  • 2000-12-12 US US10/168,459 patent/US6673952B2/en not_active Expired - Fee Related
  • 2000-12-21 CA CA 2395559 patent/CA2395559A1/en not_active Abandoned
  • 2000-12-21 EP EP00993521A patent/EP1240284A1/de not_active Withdrawn
  • 2000-12-21 JP JP2001546852A patent/JP2003518160A/ja active Pending
  • 2000-12-21 BR BR0016548A patent/BR0016548A/pt not_active Application Discontinuation
  • 2000-12-21 CN CN00818592A patent/CN1425057A/zh active Pending
  • 2000-12-21 AU AU28576/01A patent/AU2857601A/en not_active Abandoned
  • 2000-12-21 WO PCT/FR2000/003658 patent/WO2001046354A1/fr not_active Application Discontinuation

Non-Patent Citations (1)

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