EP2164937A2 - Amélioration de la décantation dans un procédé de production d'esters alkyliques à partir d'huile végétale ou animale et d'un monoalcool aliphatique - Google Patents
Amélioration de la décantation dans un procédé de production d'esters alkyliques à partir d'huile végétale ou animale et d'un monoalcool aliphatiqueInfo
- Publication number
- EP2164937A2 EP2164937A2 EP08826260A EP08826260A EP2164937A2 EP 2164937 A2 EP2164937 A2 EP 2164937A2 EP 08826260 A EP08826260 A EP 08826260A EP 08826260 A EP08826260 A EP 08826260A EP 2164937 A2 EP2164937 A2 EP 2164937A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- phase
- glycerine
- glycerin
- stream
- flow
- 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- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Definitions
- the invention relates to an improved process for producing alkyl esters from vegetable or animal oils and an aliphatic monoalcohol.
- the alkyl esters of vegetable oils are produced from vegetable oils derived for example from rapeseed, sunflower, soy or even palm. Poorly adapted to the direct supply of modern diesel engines in passenger cars, vegetable oils consisting essentially of triglycerides must be converted by a transesterification reaction with an alcohol, for example methanol or ethanol, introduced in excess to produce esters. vegetable oil methyl esters (VOME) and glycerine.
- VOME vegetable oil methyl esters
- glycol means the pure body of chemical formula C 3 H 8 O 3 and glycerine or glycerin phase, a mixture containing mainly glycerol and other impurities, such as, for example, water, methanol, mono-, di- and tri-glycerides, the mono-and di-glycerides being triglycerides partially converted by the transesterification reaction.
- the Esterfip-H TM process developed by I 1 I FP makes it possible to obtain a biodiesel and a glycerine of very good quality, with high yields.
- the basic scheme of this process consists of two fixed bed transesterification reactors using a solid heterogeneous catalyst, operating continuously and installed in series, which makes it possible to maximize the conversion.
- the effluent from the first reactor is subjected to partial evaporation to remove the excess methanol introduced, and thus promote the separation of the glycerin formed while favorably displacing the reaction equilibrium to maximize the conversion in the second reactor.
- the second transesterification reaction most of the excess methanol is removed by evaporation (more than 99%) and recycled.
- the insoluble glycerin is removed by decantation and a final purification step of the methyl esters consists of the removal of the soluble glycerin by passage over a column filled with a selective adsorbent. Content water in the reaction medium is controlled to remain below a given limit value as described in US Pat. No. 6,878,837 filed in the name of the Applicant.
- the current European standard on biofuels EN 14 214 imposes maximum levels of methanol, water, free glycerol and mono-, di- and triglycerides: 0.2% mass for methanol, 500 mg / kg for water 0.02% free glycerol mass, 0.8% monoglyceride mass and 0.2% di- and triglyceride mass.
- Free glycerol as opposed to bound glycerol, is defined as being a glycerol molecule totally detached from any carbon chain and of formula C 3 H 8 O 3 .
- the flow A at the outlet of the reaction section, contains mainly methyl esters, methanol, glycerol and partially converted glycerides (monoglycerides , diglycerides and triglycerides), as well as traces of water, impurity present in the load.
- the conversion reached in this reaction section (two reaction stages with an intermediate stage of separation of the co-produced glycerin) makes it possible to obtain partial glyceride contents compatible with the European standard for biodiesel.
- the solubility equilibrium that is defined by the content of the product P1 in the phase containing predominantly P2 and reciprocally the content of the product P2 in the phase containing predominantly P1 depends on the amounts of P1 and P2 in the initial mixture, the temperature, and the presence of a body P3 which can act as a co-solvent, that is to say increase the concentration of one of the products in the phase containing mainly the other.
- the methyl esters and the glycerol are not very soluble and the methanol acts as co-solvent. So the glycerol content in the ester phase is all the more important that the temperature is high and the methanol content is high.
- pure glycerol has a density close to 1.2 g.cm '3 while that of the ester is around 0.9 g.cm "3.
- the phase containing predominantly glycerol is therefore denser than the ester phase and thus tends to be below the latter under the effect of gravity, the ester phase thus constituting the supernatant phase.
- the separation of methanol from the flow A from the reaction section is effected by evaporation in two stages, the second being done under vacuum, to reach the methanol and water contents authorized by the standard (zone (1) in Figure 1), the flow B corresponding to evaporated methanol.
- methanol acts as a co-solubilizer for methyl esters and glycerol
- this evaporation step renders a portion of the glycerol present in this stream insoluble at a content of between 0.1 and 5% by weight.
- the soluble part represents at room temperature 500 to 700 ppm mass, the maximum permissible content imposed by the European standard being 200 ppm mass of free glycerol. This therefore requires separating both the insoluble glycerol and a part of the soluble glycerol. This separation is done in several stages.
- Stream C from the evaporation stage is at a temperature between 80 0 C and 180 0 C 1 and preferably between 120 ° C and 160 ° C.
- the first step is to reduce its temperature in a heat exchanger (2).
- the flow D of the same composition as the stream C but at a lower temperature of between 10 and 100 ° C., preferably between 35 ° and 75 ° C. is composed for the most part of an ester phase. said continuous and from 0.01 to 10% glycerol mass and preferably from 0.5 to 5% mass of insoluble glycerol and dissolved in the ester phase.
- the insoluble glycerin phase is very often dispersed in the form of droplets. These droplets can be formed during the appearance of the insoluble glycerine phase. They can also be divided into rotating machines, control valves or other process equipment in which the fluid reaches high speeds causing strong agitation.
- the insoluble glycerine phase therefore consists of a population of many droplets of different sizes.
- the separation of the glycerin phase is then by gravity settling.
- This step consists of sending this stream into a settling tank 3 whose function is to enable to glycerin phase droplets, denser than the ester phase to fall under the action of gravity.
- the size of the settling tank and the residence time of the charge in this apparatus define the threshold of the decanter.
- the cutoff threshold is expressed in ⁇ m and corresponds to the minimum size of the drops that can be separated by decantation in the flask. Below this threshold, the droplets do not decant sufficiently rapidly in the decanter and are entrained with the ester phase in the subsequent steps of the process. However too long settling times require greater immobilization of effluents, resulting in expensive over-storage and losses in the profitability of the process.
- the cut-off threshold is around 100 ⁇ m, the settling times are fast and of the order of less than one hour ("liquid-liquid extraction", description of devices, J. Leybros, engineering techniques , Process Engineering, J2764). If the cut-off threshold is less than 10 ⁇ m, the settling times become very long and the cost of installation is significantly increased.
- the settling tank may be in the form of a cylindrical capacity whose axis of symmetry is placed horizontally.
- the flow D containing the ester with drops of glycerine phase is injected at one end of the flask. Two exits are placed at the other end of the balloon. One located on the upper generatrix to collect the supernatant ester phase, the other located at the bottom of the settling tank to collect the glycerin phase.
- the ester flow containing the droplets of glycerine will therefore travel in the settling tank horizontally from the inlet to the outlets at a speed depending on the section and therefore the diameter of the flask.
- Coalescers are systems that make it possible to increase the size of fine droplets by promoting the phenomenon of coalescence, ie the formation of larger droplets (Perry's Chemical Engineers' Handbook, 7 m Edition, Chp 15-17 " Liquid-liquid extraction equipment "). Droplets once become larger can more easily be separated by decantation, for example.
- the coalescers are fibrous or porous solid beds whose properties are chosen according to the system to be separated. Generally, cotton and glass fibers are used. Like all industrial equipment, the coalescer does not achieve a perfect separation or can be made to operate in degraded operation (very high flow rate, aging, fouling, etc.). Part of the fine droplets can pass through the coalescing medium.
- the final ester treatment chain thus comprises a decanter (3) for separating the majority of the glycerine, a coalescer (4) for the insoluble residual glycerine and a solid adsorption zone (5) for separating the dissolved glycerin. of the ester phase I.
- the main separation step takes place in the clarifier, while the steps taking place in the coalescer or in the solid adsorption zone represent finishing steps.
- the solid adsorption zone for example on ion exchange resins, is in contact with a part of the insoluble glycerine. But their use will be all the more optimized as the share of Insoluble glycerin to be separated from the ester phase will be weak. In the presence of too much glycerol and glycerine, the adsorbent solids tend to saturate more quickly. The frequency of the adsorption / regeneration cycles increases. The regeneration is done using a solvent, preferably methanol. However, the repeated alternation of these cycles considerably reduces the life of the solids. For an optimized operation of these solids, at the outlet of the coalescer, the flow H must contain only 500 to 700 ppm mass of soluble glycerol.
- the present invention therefore provides a simple and improved process scheme which overcomes the aforementioned drawbacks and wherein the efficiency of the separation of glycerine is significantly improved at the decanter.
- the effectiveness of this decantation step conditions the sizing of the apparatus necessary for the subsequent steps of the process.
- increasing the efficiency of the decanter makes it possible to reduce the size of the coalescer and to increase its efficiency.
- the amount or the cycle time of the solids used in the adsorption zone, for example the ion exchange resins, is thereby increased.
- the present invention describes a process for producing alkyl esters of vegetable or animal oils and glycerin in which the separation between the ester phase and glycerine is improved.
- the effectiveness of the gravitational settling of small glycerin droplets is improved by a step of recontacting with a glycerine phase, thus making it possible to increase their size and to facilitate their decantation.
- the invention describes the plant in which the process for producing alkyl esters of vegetable or animal oils and glycerine with improved separation between the ester phase and glycerine is carried out.
- Figure 1 gives a schematic representation of part of the Esterfip-H TM process as described in the prior art.
- Figure 2 gives a schematic representation of an Esterfip-H TM process part including the improvement proposed according to the present invention.
- Figure 3 gives a schematic representation of a portion of the Esterfip-H TM process according to a second embodiment of the present invention.
- the present invention describes a process for the production of alkyl esters of fatty acids and of glycerol using in a reaction section a set of transesterification reactions between a vegetable or animal oil and an aliphatic monoalcohol, and using a heterogeneous solid catalyst, comprising: a) a step of recontacting the effluent from the reaction section, comprising partially converted alkyl esters, glycerol and triglycerides, and separated from the excess alcohol, with a glycerine phase of purity greater than 50; % mass, then b) a step of mixing said effluent with said glycerin phase and c) a step of decanting the glycerin phase and obtaining a supernatant ester phase.
- the ester phase obtained can be sent to one or more stages of separation of the residual glycerin.
- this subsequent separation takes place first in a coalescer, from which a glycerin phase and a very poorly insoluble glycerin ester phase are extracted.
- the ester phase is then sent to at least one solid adsorption zone to separate the soluble glycerin and thereby obtain an ester phase with fuel specifications.
- the process according to the present invention thus makes it possible to significantly improve the separation of glycerine. This is due to the increase in droplet size.
- the settling front separating the glycerin from the ester phase therefore progresses more rapidly in the presence of added glycerine.
- the invention makes it possible to optimize the decantation stage (size of the settling tank, residence time, production) and also the possible subsequent stages of separation of residual glycerin depending on the needs of the operator.
- Figure 2 is a schematic of a particular embodiment of the improved method of the present invention.
- an effluent comprising alkyl esters, glycerol, partially converted triglycerides and alcohol
- this separation zone may be a coalescer (4) for separating residual insoluble glycerin and / or a solid adsorption zone (5) in order to separate the soluble glycerol from the ester phase.
- Flow A is derived from the reaction section and consists mainly of partially converted alkyl esters, alcohol, glycerol and triglycerides.
- the step performed in zone (1) is a step of evaporation of the excess alcohol.
- the stream C is then subjected to cooling in a heat exchanger (2), in order to reduce the glycerol content dissolved in the ester phase.
- the recontacting step is then carried out: a stream J, enriched in glycerin, is mixed with the flow D coming from the heat exchanger (2) and containing micro-droplets of glycerine.
- This flow J represents 0.1 to 100% by volume of the flow rate of flow D corresponding to the effluent leaving the heat exchanger. Preferably, it represents 1 to 50% by volume of flow flow D.
- the stream J contains at least 50% glycerol mass and preferably 75% glycerol mass and even more preferably 90% glycerol mass.
- the glycerin used for this recontacting step consists of the streams J1 and / or J2.
- the stream J1 corresponds to a glycerine phase originating from an external source and having a purity greater than 50% by weight, preferably greater than 70% by weight, and even more preferably greater than 90% by mass.
- the stream J2 corresponds to a part of the flow F 'and is composed of glycerine of purity of at least 50% by weight, preferably greater than 75% by weight and even more preferably greater than 90% by weight, directly withdrawn from the clarifier (3) .
- the stream J comes entirely from the recycle (stream J2) glycerine withdrawn decanter (3) and represents a part of the flow F '.
- Figure 3 shows another embodiment of the recontacting step according to the invention, wherein said recontacting step takes place upstream of the heat exchanger (2).
- an effluent comprising alkyl esters, glycerol, partially converted triglycerides and alcohol,
- this separation zone may be a coalescer (4) for separating residual insoluble glycerin and / or a solid adsorption zone (5) in order to separate the soluble glycerin from the ester phase.
- the flow A from the reaction section and mainly consisting of alkyl esters, alcohol, glycerol and partially converted triglycerides is sent to the zone (1) in which the excess alcohol is evaporated.
- the flow J 'of glycerin is thus mixed with the flow C, directly obtained after the evaporation step (2) of the excess alcohol.
- This flow J ' represents 0.1 to 100% by volume of the flow rate of flow C corresponding to the effluent leaving the heat exchanger. Preferably, it represents 1 to 50% by volume of the flow of the stream C.
- the stream J ' contains 50% glycerin mass, preferably 75% by weight and even more preferably 90% glycerin mass.
- the glycerin used for this recontacting step consists of the streams J'1 and / or J'2.
- the flow I1 corresponds to a glycerin phase originating from an external source and having a purity of at least 50% by weight, preferably greater than 75% by weight and even more preferably at 90% by weight.
- the flux J'2 corresponds to a part of the flow F 1 and is composed of glycerine of purity of at least 50% by weight, preferably greater than 75% by weight and very preferably greater than 90% by mass, directly withdrawn from the clarifier (3)
- the flow J ' comes entirely from the recycle (flux J'2) glycerine withdrawn decanter (3) and represents a part of the flow F'.
- the recontacting step is preceded by a step of cooling the flow coming from the reaction section and separated from the excess of alcohol, whereas in the embodiment according to FIG. the recontacting step is followed by this cooling step.
- a static mixer is a device in which a plurality of generally fixed solid surfaces are arranged, the normals of these surfaces being in different directions of space, so as to produce a flow with many changes of orientation to mix the incoming fluxes.
- the surfaces inside the static mixer may be formed by the outer casings of particles of different shapes and sizes arranged in a pipe generally of circular section. It may also be baffles connected to the walls of the pipe, structured linings of SM V® or SMX® type Sulzer Company.
- a dynamic mixer has a rotor on which blades are arranged.
- An electric motor rotates the rotor and therefore drives the blades which thereby ensure a mixture of flows into the balloon with this rotor.
- this mixing step is to generate from the glycerin introduced a large quantity of drops of sufficient size to settle easily.
- the characteristics of the mixer are therefore determined according to this constraint imposed on the size of the droplets. This significantly increases the probability of encounter between the glycerin microdroplets dispersed in the ester phase and the drops of sufficient size from the glycerin phase introduced during the recontacting step. The drops will meet and merge or coalesce. Thus, the resulting drop will have a larger size than the two starting drops and thus will settle more easily.
- An advantage of the present invention is to reduce the size of the clarifier by increasing the size of the droplets.
- a stream F 'of glycerin is extracted, while the ester phase is drawn off on the top of the flask (stream E').
- the flow E ' due to the improved settling, contains less glycerin entrained in the ester phase.
- the flow E 'can be sent to a coalescer (4).
- this equipment will be smaller in size.
- a G 'stream of glycerine is withdrawn at the bottom of the coalescer.
- the stream H 'of esters extracted from the coalescer (4) containing practically no longer and preferably no longer at all insoluble glycerin can advantageously be sent to the zone (5) for a step of adsorption on solids.
- the alternation of the adsorption / regeneration cycles undergone by solids is thus less frequent and their lifetime is therefore increased.
- the solid regeneration phases are carried out with a smaller amount of solvent. In this way, the economy of the processing chain is greatly improved. If the decantation makes it possible to separate sufficiently insoluble glycerin, it is possible, for example, advantageously to send the ester stream coming from the decanter (3) directly to a solid adsorption zone (5), without the need for a additional step of coalescence.
- this limit is defined as the decantation front.
- the monitoring of the decantation front and in particular the speed of displacement of this front make it possible to estimate the size of the drops present in the ester phase.
- a sample of an emulsion consisting of the continuous ester phase containing droplets of glycerin is placed in a graduated cylinder. By following the time the displacement of the decantation front, it is possible to calculate a speed of displacement of this front. From standard values correlating the size of the drops and the speed of displacement of the decantation front, it is possible to deduce the sizes of the droplets among the smaller ones.
- Decantation times of the order of several hours involve very small drop sizes of the order of a few microns.
- Drop size measurements are also confirmed by light microscopy, by placing samples of the emulsion under a variable magnification optical microscope. The different sizes of glycerine droplets coexisting in the ester-glycerin mixture are thus directly measured. These sizes thus measured also make it possible to check the results obtained by monitoring the decantation front.
- a sample A of the ester-glycerine mixture is taken after the step of evaporation of the excess of methanol produced at the outlet of the reaction section, and after the cooling step (corresponds to the flow D in FIG. 1).
- This sample is in the form of an emulsion.
- a sample B is prepared in the laboratory, bringing into contact 97% of esters (biofuel with the specifications) with 3% of glycerin of purity of at least 97% by weight.
- One liter of mixture is placed for 20 minutes in a mechanical stirrer type IKA Ultraturrax rotating at 21,000 revolutions / min.
- the rate of drop of the drop of glycerine in the continuous ester phase depends on various factors: the difference in density p between the ester phase and the glycerine phase, the viscosity ⁇ of the ester phase and the diameter d of the drop. This last parameter related to the size of the drop is the most important since for droplets of sufficiently small size, the settling speed varies according to the square of the diameter.
- sample C is prepared in the same manner as sample B by adding 25% glycerin volume of purity of at least 97% by weight. Mechanical stirring carried out by the rotation of a propeller shaft at 450 rpm is applied to this sample C of 800 ml volume for 15 minutes.
- Tests were performed on a unit, on a 50 mm diameter column.
- the column is filled with glass beads 2 or 6 mm in diameter.
- the tests consisted in varying the flow rate of the emulsion at 4% by weight of glycerine in the ester while the glycerin flow rate used for the recontacting was kept constant at the value of 58 kg / h.
- the flow is upcurrent (UF) or downward (DF).
- the recontacting in the column clearly makes it possible to reduce the quantity of glycerin initially present in the emulsion: the gains measured under the conditions given in the table range from 30 to more than 50%.
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- Chemical & Material Sciences (AREA)
- General 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)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0704711A FR2918059B1 (fr) | 2007-06-29 | 2007-06-29 | Amelioration de la decantation dans un procede de production d'esters alkyliques a partir d'huile vegetale ou animale et d'un monoalcool aliphatique. |
PCT/FR2008/000782 WO2009007529A2 (fr) | 2007-06-29 | 2008-06-09 | Amélioration de la décantation dans un procédé de production d'esters alkyliques à partir d'huile végétale ou animale et d'un monoalcool aliphatique |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2164937A2 true EP2164937A2 (fr) | 2010-03-24 |
Family
ID=38698805
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08826260A Withdrawn EP2164937A2 (fr) | 2007-06-29 | 2008-06-09 | Amélioration de la décantation dans un procédé de production d'esters alkyliques à partir d'huile végétale ou animale et d'un monoalcool aliphatique |
Country Status (4)
Country | Link |
---|---|
US (1) | US8350071B2 (fr) |
EP (1) | EP2164937A2 (fr) |
FR (1) | FR2918059B1 (fr) |
WO (1) | WO2009007529A2 (fr) |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3515403A1 (de) * | 1985-04-29 | 1986-10-30 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur katalytischen umesterung von fettsaeureglyceriden mit niederen alkanolen |
FR2752242B1 (fr) * | 1996-08-08 | 1998-10-16 | Inst Francais Du Petrole | Procede de fabrication d'esters a partir d'huiles vegetales ou animales et d'alcools |
FR2838433B1 (fr) * | 2002-04-11 | 2005-08-19 | Inst Francais Du Petrole | Procede de production d'esters alkyliques a partir d'une huile vegetale ou animale et d'un monoalcool aliphatique |
FR2872812B1 (fr) | 2004-07-12 | 2006-09-08 | Inst Francais Du Petrole | Procede de production d'esters alkyliques d'acides gras et de glycerine de haute purete |
CA2621007A1 (fr) * | 2005-05-25 | 2006-11-30 | Long Island Technical Associates, Llc | Procede de production d'esters a partir de flux d'hydrocarbures contenant des olefines et d'huiles vegetales ou animales |
-
2007
- 2007-06-29 FR FR0704711A patent/FR2918059B1/fr not_active Expired - Fee Related
-
2008
- 2008-06-09 WO PCT/FR2008/000782 patent/WO2009007529A2/fr active Application Filing
- 2008-06-09 EP EP08826260A patent/EP2164937A2/fr not_active Withdrawn
- 2008-06-09 US US12/666,885 patent/US8350071B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO2009007529A2 * |
Also Published As
Publication number | Publication date |
---|---|
US8350071B2 (en) | 2013-01-08 |
WO2009007529A2 (fr) | 2009-01-15 |
FR2918059B1 (fr) | 2010-10-29 |
US20100292493A1 (en) | 2010-11-18 |
WO2009007529A3 (fr) | 2009-04-09 |
FR2918059A1 (fr) | 2009-01-02 |
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