EP2170481A2 - Procédé de traitement d'émulsions inhibées par coalescence, issues de biotransformations de cellules complètes, à l'aide de gaz comprimés ou supercritiques, en particulier à l'aide de dioxyde de carbone - Google Patents

Procédé de traitement d'émulsions inhibées par coalescence, issues de biotransformations de cellules complètes, à l'aide de gaz comprimés ou supercritiques, en particulier à l'aide de dioxyde de carbone

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Publication number
EP2170481A2
EP2170481A2 EP08784358A EP08784358A EP2170481A2 EP 2170481 A2 EP2170481 A2 EP 2170481A2 EP 08784358 A EP08784358 A EP 08784358A EP 08784358 A EP08784358 A EP 08784358A EP 2170481 A2 EP2170481 A2 EP 2170481A2
Authority
EP
European Patent Office
Prior art keywords
emulsion
compressed
carbon dioxide
supercritical gas
container
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08784358A
Other languages
German (de)
English (en)
Inventor
Gabriele Sadowski
Andreas Schmid
Bruno BÜHLER
Michael GÖRNERT
Christoph Brandenbusch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Universitat Dortmund
Technische Universitaet Dortmund
Original Assignee
Universitat Dortmund
Technische Universitaet Dortmund
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE102007034258A external-priority patent/DE102007034258A1/de
Application filed by Universitat Dortmund, Technische Universitaet Dortmund filed Critical Universitat Dortmund
Publication of EP2170481A2 publication Critical patent/EP2170481A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/02—Separating microorganisms from their culture media
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
    • B01D17/02—Separation of non-miscible liquids
    • B01D17/04—Breaking emulsions
    • B01D17/044—Breaking emulsions by changing the pressure
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
    • B01D17/02—Separation of non-miscible liquids
    • B01D17/04—Breaking emulsions
    • B01D17/047—Breaking emulsions with separation aids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/06—Lysis of microorganisms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D21/00—Separation of suspended solid particles from liquids by sedimentation
    • B01D21/02—Settling tanks with single outlets for the separated liquid

Definitions

  • the invention relates to a process for working up coalescence-inhibited emulsions from whole-cell biotransformations with compressed or supercritical gases, in particular with carbon dioxide, according to the preamble of claim 1.
  • an aqueous-organic two-phase system For the biocatalytic conversion of apolar organic molecules, an aqueous-organic two-phase system is often used [1-5].
  • This system permits the use and accumulation of high concentrations of poorly water-soluble substrates and products, the organic phase consisting of an apolar, non-toxic solvent or a mixture of several solvents serving as a substrate reservoir and / or as a product sink.
  • the organic phase protects against toxic effects of substrates and products.
  • the characteristic distribution of substrates and products in the two phases can be used to prevent kinetic product inhibition, direct equilibrium reactions in the desired direction, increase enantioselectivity, and control multi-step reactions.
  • Such two-phase systems are highly emulsified to achieve high mass transfer rates.
  • the formation of stable emulsions is also promoted by high biocatalyst concentrations, especially when whole microbial cells are used.
  • high concentrations of macromolecular surface-active substances lipids, proteins, polysaccharides, biosurfactants, cell debris
  • phase separation Since in bi-phase bioprocesss, apart from product isolation, for economic and ecological reasons, solvent recycling is also essential, the two phases must be separated from each other after biotransformation. These Phase separation has proven to be difficult with stable coalescence-inhibited emulsions, such as occur when whole microbial cells are used. Various methods for phase separation, such as centrifugation, membrane filtration, filter coalescence, addition of de-emulsifiers or thermal processes, gave unsatisfactory results or were very expensive in terms of apparatus and time [7]. Complex phase separation is considered to be a major limitation for the industrial implementation of biphasic bioprocesses with their great economic as well as ecological potential. In the field of phase separation in two-phase whole-cell biotransformations there is therefore a need for innovation.
  • the systems are initially roughly separated from the biotransformation by centrifugation. Subsequently, several filtration and (UItra) centrifugation steps are carried out in order to achieve a sufficient separation.
  • the organic phase obtained in this way is then subjected to a distillative or extractive work-up in order to separate off the desired product (however, sufficient phase separation can not be achieved.) It is therefore not possible to completely separate the organic product containing the desired value from the aqueous phase separate, which makes further processing considerably more difficult).
  • a disadvantage of the previous methods is in addition to the high number of purification steps, the possibly necessary use of a solvent used for extraction, which must then be recovered again.
  • the separation of aqueous-organic biphasic systems under discussion here is described below by way of example by the separation of coalescence-inhibited emulsions from biphasic whole-cell biotransformations, for example in apolar solvents.
  • the reaction mixture present here after biotransformation does not separate spontaneously and, after prolonged standing, essentially exists as shown in FIG.
  • the mixture is optically composed of three phases, with a milky organic / aqueous emulsion forming the upper phase (I), which in addition to the organic solvent contains the educt, by-products and the product.
  • the second optically identifiable phase (II) is an aqueous phase in which the nutrients necessary for cultivation (which are also partially present in the emulsion) are located and from which the cells / biomass (III) are in a third phase drop.
  • oil-in-water emulsions [10, 11] are frequently used, examples of which are known, for example, from US Pat. No. 6 566 410 B1 Similar applications are for example from DE 101 14 920 A1 for the extraction of organic monomers known.
  • the invention is based on a process for working up a coalescence-inhibited emulsion comprising constituents of whole-cell biotransformations such as cells, soluble cell constituents, organic solvents and / or water.
  • a process for working up a coalescence-inhibited emulsion comprising constituents of whole-cell biotransformations such as cells, soluble cell constituents, organic solvents and / or water.
  • the coalescence-inhibited emulsion stable after the biotransformation is admixed in excess in a container with at least one compressed or supercritical gas and mixed at elevated pressure and elevated temperatures for a prescribable period of time, after which the aqueous and the organic phase of the emulsion separate from each other and the cells and cell constituents separate both the aqueous and the organic phase in the range of their interfaces or phase boundaries and then separated.
  • the compressed or supercritical gas such as carbon dioxide
  • a pressure eg about 115 bar and at a temperature of about 45 ° C, for example preferably mixed intensively with the compressed or supercritical gas for 2 minutes.
  • a sharp separation of the aqueous and organic phase is then observed, whereby cell constituents at the interfaces of the phases (for example also at an interface to a container or the like) both at the lower end of the aqueous phase and the organic phase deposit. These cell constituents can now be easily separated, since they sediment faster than the original emulsion.
  • the inventive method offers an enormous potential to separate emulsions from biocatalytic processes (such as whole-cell biotransformations using microorganisms as catalysts) and work up with little equipment and cost.
  • compressed or supercritical gases such as compressed carbon dioxide as a solvent, high efficiency can be achieved in further process steps.
  • the cells (IV) present in the aqueous phase (IM) settle at the bottom of the vessel, but also that the cell fragments present in the interphase / emulsion phase / Collect macromolecules (II) at the phase interface between an organic phase (I) and an aqueous phase (III). This is done after switching off the stirrer within a very short time (typically less than 2 minutes).
  • the volume ratio of organic to aqueous phase is advantageously 1: 1.
  • the separation state obtained by working up with compressed or supercritical gas, such as compressed carbon dioxide, is retained even after expansion and outgassing of the compressed or supercritical gas (and remixing).
  • compressed or supercritical gases can furthermore achieve that, depending on the composition and properties of the emulsion, a suitable compressed or supercritical gas or even a plurality of such gases can be introduced simultaneously into the emulsion so as to separate the emulsion into the different ones Phase to allow.
  • the method is therefore basically feasible with all compressed or supercritical gases, which is particularly favorable to carry out with carbon dioxide.
  • the compressed or supercritical gas as carbon dioxide, this is always to be regarded as an exemplary abbreviation for the term compressed or supercritical gas and to be interpreted in the sense that beside or alternatively to the expressly mentioned Carbon dioxide, other compressed or supercritical gases, whether individually or as mixtures, can be used according to the information described herein.
  • a gas whose critical data is similar to the critical data of carbon dioxide is used as the compressed or supercritical gas. Since the solubility of carbon dioxide in emulsions is particularly advantageous for the separation of the emulsion, it can be expected, even when using compressed or supercritical gases with similar critical data and / or solution properties, that a corresponding separation of the phases of the emulsion can be brought about.
  • similarity of the critical data and / or solution properties it is to be understood that similar effects can be brought about in the emulsion, as was also the case with carbon dioxide.
  • propane, butane or the like gases are used as the compressed or supercritical gas.
  • the critical data and solution properties of such low-valent hydrocarbons is quite similar to that of carbon dioxide and thus also suitable for carrying out the method according to the invention.
  • such gases are available at low cost and non-technical largely unproblematic.
  • the gas when using a compressed or supercritical gas with a poorer solution property than carbon dioxide in the emulsion, the gas is introduced under increased pressure in the emulsion and / or the emulsion is separated and thus the poorer solution properties are at least partially compensated.
  • the cells and cell constituents deposit at the lower end of both the aqueous and the organic phase.
  • these separate phases can be subjected to further purification, in particular for obtaining a valuable substance contained in at least one of the phases.
  • the substance of value is any substance within the emulsion which represents a desired result of the biocatalytic process and is to be made available for use in conventionally technical quantities.
  • the aqueous phase with the separated cells and cell constituents and the organic phase with the separated cells and cell constituents are separately withdrawn from the separated emulsion and separated in each case for further purification, for example by sedimentation processes or the like Extraction of cells or cell components can be subjected.
  • the emulsion may be mixed in a container with the compressed or supercritical gas in so-called batch mode, whereupon the phases separate in the same container after mixing and form a layered arrangement of the individual phases or components in the container, whereupon the phases or components from the individual layers are withdrawn separately from the container.
  • the emulsion is intensively mixed in a first container with the compressed or supercritical gas and the homogeneous mixture of emulsion and compressed or supercritical gas produced thereby is placed in a second container , in which the phases, preferably at slow ren, separate and form a layered in the second container arrangement of the individual phases or constituents, after which the phases or components from the individual layers are withdrawn separately from the second container.
  • the phases preferably at slow ren, separate and form a layered in the second container arrangement of the individual phases or constituents, after which the phases or components from the individual layers are withdrawn separately from the second container.
  • the emulsion is mixed intensively in a first container with the compressed or supercritical gas and the homogeneous mixture of emulsion and compressed or supercritical gas is transferred to a second container in which the aqueous and the organic phase, preferably with slow stirring, separate, after which the aqueous and the organic phase are withdrawn separately from the second container in more containers in which then separate the cells and cell components of the aqueous and the organic phase and the compressed or supercritical gas to let.
  • the work-up involves an extraction step for obtaining a valuable substance, preferably from the organic phase of the emulsion. tet.
  • a valuable substance preferably from the organic phase of the emulsion.
  • Such extractions even using, for example, supercritical carbon dioxide as a compressed or supercritical gas are basically known and are used, for example, often for the extraction of individual substances from plant components such as in spice production.
  • the valuable substance can be separated out directly from the emulsion and withdrawn separately and / or together with impurities.
  • the residual emulsion is further separated in a subsequent extraction of the valuable substance following separation with the addition of compressed or supercritical gas and the constituents of the residual emulsion are separated off separately. This also allows reusable substances to be specifically recovered.
  • an extraction can be carried out by means of compressed or supercritical gas.
  • the compressed or supercritical gas already used in the cell / emulsion separation can also be used for extraction. This can be easily recovered after the extraction by lowering the pressure and used again in the process.
  • at least one process step from chromatography, crystallization, distillation, adsorption, absorption, membrane processes or filtration or combinations of these methods can be used.
  • FIG. 1 shows a typical arrangement of the phases in a reaction mixture after biotransformation and after settling
  • FIG. 2 shows a typical arrangement of the phases in a reaction mixture according to FIG.
  • FIG. 1 after prolonged centrifugation
  • FIG. 3 typical arrangement of the phases in a reaction mixture after the application of the method according to the invention
  • FIG. 4 shows a first preferred embodiment of an apparatus for carrying out the method according to the invention for separating the coalesced-inhibited emulsion
  • FIG. 5 shows another preferred embodiment of an apparatus for carrying out the method according to the invention for separating the coalescence-inhibited emulsion in two steps
  • FIG. 6 shows a further preferred embodiment of an apparatus for carrying out the method according to the invention for separating the coalescence-inhibited emulsion
  • FIG. 7 shows a first possibility for the realization of the product processing by emulsion separation after the extraction of the desired product
  • FIG. 8 shows another possibility for realizing the product processing by emulsion separation before extraction of the desired product
  • FIG. 9 shows a further possibility for the realization of the product work-up by emulsion separation before an isolation of the desired product by one or more further separation step (s),
  • FIG. 10 shows the extraction behavior of the emulsion for a sample solution
  • FIG. 11 is a table of critical data of selected fluids that are used in industrial applications for use in high pressure processing and can also be used in the process of the present invention.
  • FIGS. 4 to 10 Various processes are shown in FIGS. 4 to 10, with which an emulsion resulting from a biotransformation can be separated into its individual constituents, whereby this process is also particularly suitable for industrial use.
  • the cell suspension from a biotransformation (phases I, II and III from FIG. 1) is introduced directly into a pressure vessel (FIG. 6) and heated to about 45 ° C.
  • compressed or supercritical gas e.g. Carbon dioxide added to the emulsion until the carbon dioxide content based on the total mass is about 75%.
  • the pressure of the mixture is increased to about 115-120 bar and intensively mixed for at least two minutes.
  • the desired phase and cell separation sets in the pressure vessel, as shown schematically in Figure 3.
  • the phase IV represents an amount of cells separated from the aqueous phase III.
  • the system obtained can be subjected to a simple separation in one or two settler units and / or the organic phase can be fed directly to a subsequent supercritical extraction with carbon dioxide to get the actual value product out of it.
  • phase separation is maintained even after draining the carbon dioxide. So can subsequently also at atmospheric pressure room temperature a significantly improved and faster phase separation can be observed.
  • the cell constituents formerly in the emulsion (phase I in FIG. 1 and phase II in FIG. 2) are now located at the phase interface between the aqueous phase (phase II in FIG. 1 and phase III in FIG. 2) and organic phase (FIG. Phase I in Fig. 2 and Fig. 3) and can be easily separated (Phase II and for the cells Phase IV in Figure 3).
  • extraction of the valuable substance can be carried out after separation of the emulsion, provided that the valuable substance dissolves in the carbon dioxide under the given conditions.
  • the solid constituents from the respective phases are separated by sedimentation.
  • This process is outlined in FIG.
  • the reaction mixture is added together with carbon dioxide under elevated pressure and elevated temperature in a pressure vessel M1 and thoroughly mixed there.
  • the homogeneous emulsion is placed in container B1, where, with further stirring, a phase separation between organic phase with cell fragments / macromolecules and aqueous phase with cells / biomass sets.
  • the respective phases can then be transferred to the containers B2 - B4.
  • the solids are separated by sedimentation.
  • the batch operation in a single container is also conceivable in which the reaction mixture is first mixed for a certain time with the addition of compressed carbon dioxide and after switching off the stirrer / homogenizer M the gravimetric waits for separation. Again, the respective phases can then be deducted directly (see Figure 6).
  • the reaction mixture is added together with carbon dioxide under elevated pressure and elevated temperature in a pressure vessel and thoroughly mixed for a certain time. Subsequently, the stirrer / homogenizer M is switched off / slowed down, so that a phase separation occurs.
  • the respective phases can then be deducted directly to subject them to further purification.
  • the process illustrated in FIG. 7 offers the advantage that the desired product can be extracted directly from the emulsion.
  • the emulsion is transferred directly to an extraction.
  • the product of value extracts directly.
  • the value product precipitates and the carbon dioxide can be recycled.
  • the remaining emulsion is subjected to the described phase separation with compressed carbon dioxide, whereby in further steps a simple separation of the solid constituents and a recycling of the solvent can take place.
  • the mass flow supplied to the extraction is large.
  • Previous separation of the aqueous phase which typically contains virtually no desired product, can significantly reduce this mass flow, which can lead to more efficient workup, as shown in FIG.
  • the emulsion is subjected to the described phase separation with compressed carbon dioxide, the aqueous phase being separated off with cells / biomass.
  • the remaining organic phase is subjected to a further purification step (e.g., a compressed CO2 extraction) in which the solids contained in the organic phase are separated by sedimentation
  • FIG. 10 shows, by way of example, the extraction behavior of the emulsion when the method according to the invention is used. Plotted is the concentration of the specified substances in the organic phase. It can be seen that the emulsion treated with 75% by mass of CO 2, in contrast to the original emulsion, has a significantly reduced concentration of the valuable substance styrene oxide.
  • a two-phase system was considered after the phase separation according to the previously proposed method.
  • This consisted of an aqueous phase, and bis-2 (ethylhexyl) phthalate as the main constituent of the organic phase, in addition to the desired product styrene oxide and octane, styrene and 2-phenylethanol were present.
  • Both phases were analyzed by gas chromatography before and after treatment with carbon dioxide.
  • the concentration of the valuable substance styrene oxide in the organic phase was greatly reduced by the treatment with carbon dioxide; Styrene oxide could not be detected in the aqueous phase. Styrene oxide was evidently extracted into the carbon dioxide-rich phase.
  • FIG. 11 shows in a table a list of critical data of selected fluids which are used in industrial applications for use in high-pressure process processes and can also be used in the method according to the invention.
  • this table is given by way of example only and does not limit the use of other compressed or supercritical gases in the process of the invention.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Thermal Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mycology (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Le procédé selon l'invention représente une possibilité pour séparer des émulsions issues de biotransformations de cellules complètes. Il est ainsi possible de séparer efficacement, à l'aide d'au moins un gaz comprimé ou supercritique, des émulsions stables qui sont formées lors d'une telle biotransformation à partir de processus biocatalytiques typiques à deux phases. L'utilisation de gaz comprimé ou supercritique comme agent de séparation permet donc de placer ensuite directement une extraction supercritique pour récupérer le produit de valeur. Peu importe alors que le produit de valeur se trouve dans la phase aqueuse ou dans la phase organique. Un recyclage de la phase organique est possible, car les constituants cellulaires tensioactifs qui sont responsables, dans une mesure déterminante, de la formation de l'émulsion stable, peuvent être séparés grâce au traitement par sédimentation. La séparation ainsi obtenue persiste alors, même après dégagement des gaz comprimés ou supercritiques, de sorte que d'autres procédés permettant d'isoler les produits peuvent encore suivre l'extraction, si nécessaire. L'invention décrite comporte donc un énorme potentiel pour exploiter, d'une manière économique aussi bien qu'écologique, des processus biocatalytiques à deux phases qui sont d'un grand intérêt.
EP08784358A 2007-07-21 2008-07-20 Procédé de traitement d'émulsions inhibées par coalescence, issues de biotransformations de cellules complètes, à l'aide de gaz comprimés ou supercritiques, en particulier à l'aide de dioxyde de carbone Withdrawn EP2170481A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102007034258A DE102007034258A1 (de) 2007-07-21 2007-07-21 Verfahren zur Aufarbeitung von koaleszenzgehemmten Emulsionen aus Ganzzell-Biotransformationen mit Kohlendioxid
DE102007059389A DE102007059389A1 (de) 2007-07-21 2007-12-06 Verfahren zur Aufarbeitung von koaleszenzgehemmten Emulsionen aus Ganzzell-Biotransformationen mit komprimierten oder überkritischen Gasen
PCT/DE2008/001177 WO2009012754A2 (fr) 2007-07-21 2008-07-20 Procédé de traitement d'émulsions inhibées par coalescence, issues de biotransformations de cellules complètes, à l'aide de gaz comprimés ou supercritiques, en particulier à l'aide de dioxyde de carbone

Publications (1)

Publication Number Publication Date
EP2170481A2 true EP2170481A2 (fr) 2010-04-07

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EP08784358A Withdrawn EP2170481A2 (fr) 2007-07-21 2008-07-20 Procédé de traitement d'émulsions inhibées par coalescence, issues de biotransformations de cellules complètes, à l'aide de gaz comprimés ou supercritiques, en particulier à l'aide de dioxyde de carbone

Country Status (4)

Country Link
US (1) US8431358B2 (fr)
EP (1) EP2170481A2 (fr)
DE (1) DE102007059389A1 (fr)
WO (1) WO2009012754A2 (fr)

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EP2870988B1 (fr) 2013-11-06 2018-03-28 Technische Universität Dortmund Procédé de traitement d'émulsions stables à partir de biotransformations à cellules entières par inversion de phase
US8961780B1 (en) 2013-12-16 2015-02-24 Saudi Arabian Oil Company Methods for recovering organic heteroatom compounds from hydrocarbon feedstocks
US9169446B2 (en) 2013-12-30 2015-10-27 Saudi Arabian Oil Company Demulsification of emulsified petroleum using carbon dioxide and resin supplement without precipitation of asphaltenes
US9562198B2 (en) 2014-05-05 2017-02-07 Saudi Arabian Oil Company Demulsification and extraction of biochemicals from crude and its fractions using water and subcritical/supercritical carbon dioxide as proton pump with pH tuning without precipitating oil components
US9688923B2 (en) 2014-06-10 2017-06-27 Saudi Arabian Oil Company Integrated methods for separation and extraction of polynuclear aromatic hydrocarbons, heterocyclic compounds, and organometallic compounds from hydrocarbon feedstocks

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EP0492857A1 (fr) * 1990-12-12 1992-07-01 Petrolite Corporation Démulsifiants pour la rupture d'émulsions formées lors de la préparation de produits pharmaceutiques
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DE10114920A1 (de) 2001-03-26 2002-10-10 Joachim Brimmer Ingenieurbuero Verfahren zur kontinuierlichen Extraktion von organischen Monomeren aus einem Reaktionsgemisch
DE102007034258A1 (de) 2007-07-21 2009-01-22 Universität Dortmund Verfahren zur Aufarbeitung von koaleszenzgehemmten Emulsionen aus Ganzzell-Biotransformationen mit Kohlendioxid
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Also Published As

Publication number Publication date
US20100145082A1 (en) 2010-06-10
US8431358B2 (en) 2013-04-30
WO2009012754A3 (fr) 2009-05-07
WO2009012754A2 (fr) 2009-01-29
DE102007059389A1 (de) 2009-06-10

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