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WO2010098695A1 - Membrane liquide supportée et procédé de récupération de composés organiques de solutions aqueuses - Google Patents

Membrane liquide supportée et procédé de récupération de composés organiques de solutions aqueuses Download PDF

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Publication number
WO2010098695A1
WO2010098695A1 PCT/RU2010/000054 RU2010000054W WO2010098695A1 WO 2010098695 A1 WO2010098695 A1 WO 2010098695A1 RU 2010000054 W RU2010000054 W RU 2010000054W WO 2010098695 A1 WO2010098695 A1 WO 2010098695A1
Authority
WO
WIPO (PCT)
Prior art keywords
membrane
liquid
organic compounds
recovery
aqueous solutions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/RU2010/000054
Other languages
English (en)
Inventor
Evgeniy Rubenovich Davidov
Petr Sergeevich Kanygin
Oleg Anatolievich Frakin
Igor Vladimirovich Cheremnov
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.)
"PROF BUSINESS" LLC
Original Assignee
"PROF BUSINESS" LLC
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
Application filed by "PROF BUSINESS" LLC filed Critical "PROF BUSINESS" LLC
Publication of WO2010098695A1 publication Critical patent/WO2010098695A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/36—Pervaporation; Membrane distillation; Liquid permeation
    • B01D61/362—Pervaporation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/38—Liquid-membrane separation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation

Definitions

  • the present invention relates to a membrane process for recovery of organic compounds from organic/water solutions. More particularly, it relates to a liquid membrane for separation of alcohols, esters and other organic compounds from water and a method of using such membrane.
  • Pervaporation is a method for the separation of mixtures of liquids by vaporization through a membrane.
  • the membrane acts as a selective barrier between the two phases, the liquid phase feed and the vapor phase permeate. Pervaporation differs from all other membrane processes because of the permeate phase change.
  • the driving force for transport of different components is provided by a chemical potential difference between the liquid feed/retentate and vapor permeate at each side of the membrane.
  • the upstream side of the membrane is at ambient pressure and the downstream side is under vacuum (or by using sweep gas) to allow the evaporation of the selective component after permeation through the membrane.
  • US 5755967 discloses a pervaporation process for the selective removal of acetone and/or butanol from an aqueous solution comprising acetone or butanol, or mixtures thereof.
  • the silicalite, silicalite filled polymer membrane is suited to the removal of acetone and butanol from the aqueous solution.
  • the driving force of the process is a pressure differential across the membrane, it comprises a vacuum on the permeate side of the membrane.
  • EP 0470704 discloses a membrane comprising a porous support and a non-porous separating layer of a polyimine polymer for use in separating water from an aqueous charge mixture of organic oxygenate, for example isopropanol by pervaporation.
  • a polyimine polymer for use in separating water from an aqueous charge mixture of organic oxygenate, for example isopropanol by pervaporation.
  • Various materials can be used as membranes.
  • Polymeric, ceramic, and liquid membranes have been used in the pervaporation process for removing organic compounds.
  • Liquid membrane is a liquid phase existing either in supported or unsupported form that serves as a membrane barrier between two phases (Terminology for membranes and membrane processes (IUPAC Recommendations 1996, page 1486). In supported liquid membranes the organic phase is immobilized in the pores of a porous polymer.
  • the polymeric support usually consists of ultra- or microporous membranes in the form of a sheet or hollow fiber or tube
  • Liquid membranes generally provide high solvent selectivity compared with polymeric membranes and ceramic membranes and it makes liquid membranes an area of significant interest for the recovery of dilute amounts of solvents from aqueous solutions.
  • US 5637224 relates to the removal of volatile organic compounds from aqueous solutions using a hollow fiber contained liquid membrane. Hollow fiber supported liquid membranes and plasma polymerized non-porous silicone coatings are disclosed.
  • WO 0156933 discloses a supported liquid membrane immobilized in a microporous support material, particularly, polypropylene, polytetrafluoroethylene, polyethylene and like for the removal and recovery of one or more target species, for example penicillin, organic acids.
  • liquid membranes have a tendency to degrade rapidly.
  • the instability of liquid membranes presents a major problem and drawback with respect to their use.
  • two significant problems arise because of the instability and degradation of liquid membranes.
  • membrane selectivity significantly decreases, resulting in a permeation of water through the membrane.
  • liquid membrane for recovery of organic compounds from aqueous solutions by diffuse evaporation through membrane by applying vacuum or gas wherein the liquid membrane is a layer of hydrophobic liquid on the surface of the aqueous solution.
  • the hydrophobic liquid is synthetic and/or vegetable oil and/or higher alcohols.
  • the present invention also relates to a method for recovery of organic compounds from aqueous solutions by diffuse evaporation through membrane by applying vacuum or gas wherein the membrane is a layer of hydrophobic liquid on the surface of the aqueous solution.
  • the organic compounds are alcohols
  • the hydrophobic liquid is synthetic and/or vegetable oil and/or higher alcohols.
  • the thickness of the layer of the hydrophobic liquid is about 3-30 mm on the surface of the aqueous solution.
  • the different oils such as synthetic oils, for example silicone oil, paraffin oil; vegetable oils, for example, corn oil, soy oil; some higher alcohols, higher fatty acids are used as the hydrophobic liquid. It is possible to use a mixture of the different oils.
  • the use of the liquid membrane in such process is based on that the molecules of the organic solvents are diphilic, as they consist of hydrophilic (has affinity for polar media - water, for example hydroxyl - group in alcohols) and hydrophobic (has affinity for non-polar media, hydrocarbon radical) units.
  • the diphilic molecules are oriented at the interface in a way that the hydrocarbon parts are in the hydrophobic phase and polar groups are in the aqueous solution.
  • the layer of the hydrophobic liquid is an insuperable barrier for the molecules of water; hence the vapor pressure for water over the layer is negligible as opposed to the vapor pressure for the solvents.
  • the molecules of the organic solvents When vacuum is applied to overhead of the layer of the hydrophobic liquid, the molecules of the organic solvents start to abandon the layer and are directed into a cooling device wherein the solvents are condensed.
  • the difference of solvent concentration in the aqueous solution and gas (vacuum) results in the concentration gradient and the continuous flow of the molecules of the solvents take place from the aqueous solution through the layer into vacuuming overhead space.
  • the advantages of the present invention are in providing a simple and economical, energy efficient method for recovery of organic compounds through the liquid membrane.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

L'invention concerne une membrane liquide destinée à la récupération de composés organiques de solutions aqueuses par évaporation diffuse à travers une membrane, sous vide ou sous pression gazeuse, la membrane liquide étant une nappe de liquide hydrophobe à la surface de la solution aqueuse. L'invention porte également sur un procédé de récupération de composés organiques de solutions aqueuses par évaporation diffuse à travers une membrane liquide, sous vide ou sous pression gazeuse
PCT/RU2010/000054 2009-02-25 2010-02-09 Membrane liquide supportée et procédé de récupération de composés organiques de solutions aqueuses Ceased WO2010098695A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2009106236 2009-02-25
RU2009106236/05A RU2409414C2 (ru) 2009-02-25 2009-02-25 Жидкая мембрана для выделения спиртов или эфиров из водных растворов и способ выделения спиртов или эфиров

Publications (1)

Publication Number Publication Date
WO2010098695A1 true WO2010098695A1 (fr) 2010-09-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/RU2010/000054 Ceased WO2010098695A1 (fr) 2009-02-25 2010-02-09 Membrane liquide supportée et procédé de récupération de composés organiques de solutions aqueuses

Country Status (2)

Country Link
RU (1) RU2409414C2 (fr)
WO (1) WO2010098695A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5013447A (en) * 1989-07-19 1991-05-07 Sepracor Process of treating alcoholic beverages by vapor-arbitrated pervaporation
WO2008143704A2 (fr) * 2006-12-01 2008-11-27 Gevo, Inc. Microorganismes élaborés pour produire du n-butanol et procédés correspondants

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2040798A1 (fr) * 1990-05-25 1991-11-26 Dean T. Tsou Membrane liquides favorisant la separation des olefines contenues dans des veines de gaz et procede connexe
RU2080162C1 (ru) * 1994-04-27 1997-05-27 Акционерное общество открытого типа "Научно-исследовательский и проектный институт азотной промышленности и продуктов органического синтеза" Аппарат для разделения веществ с помощью жидких мембран
RU2144075C1 (ru) * 1997-10-21 2000-01-10 Закрытое акционерное общество "Проектно-строительное предприятие ИНСЕРВ" Способ изготовления алкогольных напитков
WO2001056933A2 (fr) * 2000-02-04 2001-08-09 Commodore Separation Technologies, Inc. Procedes combinant une dispersion d'epuration et des membranes liquides sur support, et agents d'extraction
US6485650B1 (en) * 2000-08-28 2002-11-26 Facilichem, Inc. Liquid membrane separation of enantiomers
RU2270487C1 (ru) * 2004-06-11 2006-02-20 Российская Федерация в лице Министерства Российской Федерации по атомной энергии Способ экстракционной переработки жидких радиоактивных отходов
RU2297975C1 (ru) * 2005-08-25 2007-04-27 Институт нефтехимического синтеза им. А.В. Топчиева РАН (ИНХС РАН) Способ нанофильтрационного разделения жидких органических смесей

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5013447A (en) * 1989-07-19 1991-05-07 Sepracor Process of treating alcoholic beverages by vapor-arbitrated pervaporation
WO2008143704A2 (fr) * 2006-12-01 2008-11-27 Gevo, Inc. Microorganismes élaborés pour produire du n-butanol et procédés correspondants

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
MATSUMURA: "Energy saving effect of pervaporation using oleyl alcohol liquid membrane in butanol purification", BIOPROCESS ENGINEERING, SPRINGER VERLAG, DE, vol. 3, 1 January 1988 (1988-01-01), pages 93 - 100, XP009135942, ISSN: 0178-515X *
TERMINOLOGY FOR MEMBRANES AND MEMBRANE PROCESSES (IUPAC RECOMMENDATIONS, 1996, pages 1486
WEILNHAMMER ET AL: "Continuous fermentation with product recovery by in-situ extraction", CHEMICAL ENGINEERING AND TECHNOLOGY, WEINHEIM, DE, vol. 17, no. 6, 1 January 1994 (1994-01-01), pages 365 - 373, XP009135992, ISSN: 0930-7516 *
ZHONGPING SHI ET AL: "Performance evaluation of acetone-butanol continuous flash extractive fermentation process", BIOPROCESS AND BIOSYSTEMS ENGINEERING, SPRINGER, BERLIN, DE LNKD- DOI:10.1007/S00449-004-0396-7, vol. 27, no. 3, 1 May 2005 (2005-05-01), pages 175 - 183, XP019347336, ISSN: 1615-7605 *

Also Published As

Publication number Publication date
RU2009106236A (ru) 2010-08-27
RU2409414C2 (ru) 2011-01-20

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