Methods for recovering a solvent from a fluid volume and methods of removing at least one compound from a nonpolar solvent

Ginosar, Daniel M.; Wendt, Daniel S.; Petkovic, Lucia M.

Title: Methods for recovering a solvent from a fluid volume and methods of removing at least one compound from a nonpolar solvent

Abstract

A method of removing a nonpolar solvent from a fluid volume that includes at least one nonpolar compound, such as a fat, an oil or a triglyceride, is provided. The method comprises contacting a fluid volume with an expanding gas to expand the nonpolar solvent and form a gas-expanded solvent. The gas-expanded solvent may have a substantially reduced density in comparison to the at least one nonpolar compound and/or a substantially reduced capacity to solubilize the nonpolar compound, causing the nonpolar compounds to separate from the gas-expanded nonpolar solvent into a separate liquid phase. The liquid phase including the at least one nonpolar compound may be separated from the gas-expanded solvent using conventional techniques. After separation of the liquid phase, at least one of the temperature and pressure may be reduced to separate the nonpolar solvent from the expanding gas such that the nonpolar solvent may be recovered and reused.

Inventors:: Ginosar, Daniel M.; Wendt, Daniel S.; Petkovic, Lucia M.

Issue Date:: Tue Jun 10 00:00:00 EDT 2014

Research Org.:: Idaho National Laboratory (INL), Idaho Falls, ID (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1245978

Patent Number(s):: 8747673

Application Number:: 13/177,962

Assignee:: Battelle Energy Alliance, LLC (Idaho Falls, ID)

Patent Classifications (CPCs):: B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01D - SEPARATION

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B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01D - SEPARATION
B01D11/0292 - {Treatment of the solvent}
B01D17/047 - {with separation aids}

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DOE Contract Number:: AC07-05ID14517

Resource Type:: Patent

Resource Relation:: Patent File Date: 2011 Jul 07

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS

Citation Formats


                    Ginosar, Daniel M., Wendt, Daniel S., and Petkovic, Lucia M. Methods for recovering a solvent from a fluid volume and methods of removing at least one compound from a nonpolar solvent.  United States: N. p., 2014. 
        Web.

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                    Ginosar, Daniel M., Wendt, Daniel S., & Petkovic, Lucia M. Methods for recovering a solvent from a fluid volume and methods of removing at least one compound from a nonpolar solvent.  United States.

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                    Ginosar, Daniel M., Wendt, Daniel S., and Petkovic, Lucia M. Tue .  
        "Methods for recovering a solvent from a fluid volume and methods of removing at least one compound from a nonpolar solvent".  United States.  https://www.osti.gov/servlets/purl/1245978.

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@article{osti_1245978,

  title        = {Methods for recovering a solvent from a fluid volume and methods of removing at least one compound from a nonpolar solvent},

  author       = {Ginosar, Daniel M. and Wendt, Daniel S. and Petkovic, Lucia M.},

  abstractNote = {A method of removing a nonpolar solvent from a fluid volume that includes at least one nonpolar compound, such as a fat, an oil or a triglyceride, is provided. The method comprises contacting a fluid volume with an expanding gas to expand the nonpolar solvent and form a gas-expanded solvent. The gas-expanded solvent may have a substantially reduced density in comparison to the at least one nonpolar compound and/or a substantially reduced capacity to solubilize the nonpolar compound, causing the nonpolar compounds to separate from the gas-expanded nonpolar solvent into a separate liquid phase. The liquid phase including the at least one nonpolar compound may be separated from the gas-expanded solvent using conventional techniques. After separation of the liquid phase, at least one of the temperature and pressure may be reduced to separate the nonpolar solvent from the expanding gas such that the nonpolar solvent may be recovered and reused.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Jun 10 00:00:00 EDT 2014},

  month        = {Tue Jun 10 00:00:00 EDT 2014}

}

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System for use of land fills and recyclable materials
patent, September 2005

Wikstrom, Jon; Schiller, Dan; Turner, Jon R.
US Patent Document 6,938,439
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6938439

Esterification of oleic acid by methanol catalyzed by p-toluenesulfonic acid and the cation-exchange resins K2411 and K1481 in supercritical carbon dioxide
journal, September 1993

Vieville, Corinne; Mouloungui, Zephirin; Gaset, Antoine
Industrial & Engineering Chemistry Research, Vol. 32, Issue 9
https://doi.org/10.1021/ie00021a031

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Title: Methods for recovering a solvent from a fluid volume and methods of removing at least one compound from a nonpolar solvent

Abstract

Citation Formats

Method for producing fatty acid esters patent, April 2001

Process for modifying fats and oils patent, June 1993

Synthesis of Oleic Acid Esters Catalyzed by Immobilized Lipase journal, January 1996

Process for producing biodiesel, lubricants, and fuel and lubricant additives in a critical fluid medium patent, May 2005

Comparison of lipase-catalysed esterification in supercritical carbon dioxide and in n-hexane journal, January 1990

Promotion of a lipase-catalyzed esterification in supercritical carbon dioxide in the near-critical region journal, June 1996

Esterification activity of lipase entrapped in reverse micelles formed in liquefied gas. journal, January 1996

Liquid CO.sub.2 /cosolvent extraction patent, September 1988

Process for the manufacture of esters patent, April 1994

Enzyme catalyzed reactions in dense gases journal, October 1998

Production of biodiesel, lubricants and fuel and lubricant additives patent, February 1998

Enzymic esterification of fatty acid mixtures from milk fat and anhydrous milk fat with canola oil in supercritical carbon dioxide journal, November 1992

Supercritical CO.sub.2 extraction of lipids from lipid-containing materials patent, August 1984

Biocatalytic Esterification in Supercritical Carbon Dioxide by Using a Lipid-coated Lipase journal, September 1998

Supercritical fluid extraction involving hydrofluoroalkanes patent, January 1996

Process for producing lower alcohol esters of fatty acids patent, August 1979

Reactions at supercritical conditions: Applications and fundamentals journal, July 1995

Continuous reaction-separation process for enzymatic esterification in supercritical carbon dioxide journal, March 1994

Process for production of highly enriched fractions of natural compounds from palm oil with supercritical and near critical fluids patent, November 2011

Process for manufacturing a composition of fatty acid esters useful as gas oil substitute motor fuel with hydrated ethyl alcohol and the resultant esters composition patent, September 1987

Process for producing biodiesel fuel products patent, August 2010

Enhancement of Enantioselectivity by Altering Alcohol Concentration for Esterification in Supercritical CO2. journal, January 1999

The role of the reaction medium in lipase-catalyzed esterifications and transesterifications journal, June 1998

Subtilisin-catalyzed transesterification in supercritical carbon dioxide journal, September 1989

Enzymatic method for preparing transesterified oils patent, February 1994

Lipase-catalyzed alcoholysis with supercritical carbon dioxide extraction 2: Phase behavior journal, November 1997

Internal Mass Transfer Limitation During Enzymatic Esterification in Supercritical Carbon Dioxide and Hexane journal, January 1995

Method for producing fatty acid alcohol ester patent, April 2005

Process for production of fatty acid methyl esters from fatty acid triglycerides patent, March 2004

Process for the production of fatty acid alkyl esters patent, June 2002

Process for apparatus for the recovery of fats and oils patent, June 1987

Processes for the separatin of lipids patent, June 1998

Transesterification between triolein and ethylbehenate by immobilized lipase in supercritical carbon dioxide journal, January 1996

Lipase-catalysed esterification in supercritical carbon dioxide and in hexane journal, February 1997

Enzymatic interesterification in supercritical carbon dioxide. journal, January 1988

Promotion of lipase-catalyzed esterification of N-valeric acid and citronellol in supercritical carbon dioxide in the near-critical region. journal, January 1996

Alcoholysis and Glyceride Synthesis with Immobilized Lipase on Controlled-Pore Glass of Varying Hydrophobicity in Supercritical Carbon Dioxide journal, April 1998

Improved process for the production of esters from fatty substances having a natural origin patent, June 1995

Method for purifying alcohol esters patent, June 1995

Continuous synthesis of ethyl myristate by enzymatic reaction in supercritical carbon dioxide journal, June 1993

Supercritical Biocatalysis journal, February 1999

Biodiesel fuel patent, November 1996

Biodiesel fuels from vegetable oils via catalytic and non-catalytic supercritical alcohol transesterifications and other methods: a survey journal, August 2003

Production of biodiesel using expanded gas solvents patent, April 2009

Process for production of esters for use as a diesel fuel substitute using a non-alkaline catalyst patent, June 1996

Simple quantitative transesterification of lipids 1. introduction journal, January 1996

Gas oil composition patent, February 1997

Reactions in supercritical fluids - a review journal, January 1986

Liquid and supercritical carbon dioxide as organic solvents journal, December 1984

Biodiesel fuel from rapeseed oil as prepared in supercritical methanol journal, January 2001

Process for the pre-esterification of free fatty acids in fats and oils patent, October 1987

Biodiesel from vegetable oils via transesterification in supercritical methanol journal, November 2002

Methanolysis of seed oils in flowing supercritical carbon dioxide journal, March 1996

Method for removing impurities from an impurity-containing fluid stream patent, April 2010

Kinetics of transesterification in rapeseed oil to biodiesel fuel as treated in supercritical methanol journal, April 2001

System for use of land fills and recyclable materials patent, January 2009

Ester synthesis in lipase-catalyzed reactions journal, November 1998

Process parameters influencing ethanolysis of cod liver oil in supercritical carbon dioxide journal, March 1998

Enantioselective Esterification of 2-Arylpropionic Acids Catalyzed by Immobilized Rhizomucor miehei Lipase journal, March 1997

Biodiesel production: a review journal, October 1999

Process for regenerating adsorbents with supercritical fluids patent, November 1978

Preparation of secondary ether fatty acids and esters from their hydroxy fatty acid equivalents patent, March 2001

Biodiesel fuel production by transesterification of oils journal, January 2001

Esterification of decanoic acid during supercritical fluid extraction employing either methanol-modified carbon dioxide or a methanol trap journal, October 1999

Fuels as solvents for the conduct of enzymatic reactions patent, December 1997

Process for preparing alkyl esters of fatty acids from fats and oils patent, September 2001

Process for extracting and desolventizing natural oil-containing food products with minimum structural damage patent, July 1998

Enzymatic Reaction in Supercritical Fluid Carbon Dioxide Using Dry-Ice journal, October 1999

Enzymatic catalysis in supercritical carbon dioxide: Comparison of different lipases and a novel esterase journal, January 1996

Enzymatic methods for polyunsaturated fatty acid enrichment patent, March 2003

Heavy oil upgrading process patent, February 2003

Method for fractionating cooking oil patent, October 2004

Method for extraction and reaction using supercritical fluids patent, September 2001

Three-stage process for deasphalting resid, removing fines from decanted oil and apparatus therefor patent, June 1992

Chemical Reactions in Supercritical Fluids. [超臨界流体中における化学反応] journal, January 1995

Lipase Catalysed Esterification at High Pressure journal, January 1994

Enzymatic synthesis of oleyl oleate in dense fluids journal, November 1995

Method for producing fatty acid esters
patent, April 2001

Process for modifying fats and oils
patent, June 1993

Synthesis of Oleic Acid Esters Catalyzed by Immobilized Lipase
journal, January 1996

Process for producing biodiesel, lubricants, and fuel and lubricant additives in a critical fluid medium
patent, May 2005

Comparison of lipase-catalysed esterification in supercritical carbon dioxide and in n-hexane
journal, January 1990

Promotion of a lipase-catalyzed esterification in supercritical carbon dioxide in the near-critical region
journal, June 1996

Esterification activity of lipase entrapped in reverse micelles formed in liquefied gas.
journal, January 1996

Liquid CO.sub.2 /cosolvent extraction
patent, September 1988

Process for the manufacture of esters
patent, April 1994

Enzyme catalyzed reactions in dense gases
journal, October 1998

Production of biodiesel, lubricants and fuel and lubricant additives
patent, February 1998

Enzymic esterification of fatty acid mixtures from milk fat and anhydrous milk fat with canola oil in supercritical carbon dioxide
journal, November 1992

Supercritical CO.sub.2 extraction of lipids from lipid-containing materials
patent, August 1984

Biocatalytic Esterification in Supercritical Carbon Dioxide by Using a Lipid-coated Lipase
journal, September 1998

Supercritical fluid extraction involving hydrofluoroalkanes
patent, January 1996

Process for producing lower alcohol esters of fatty acids
patent, August 1979

Reactions at supercritical conditions: Applications and fundamentals
journal, July 1995

Continuous reaction-separation process for enzymatic esterification in supercritical carbon dioxide
journal, March 1994

Process for production of highly enriched fractions of natural compounds from palm oil with supercritical and near critical fluids
patent, November 2011

Process for manufacturing a composition of fatty acid esters useful as gas oil substitute motor fuel with hydrated ethyl alcohol and the resultant esters composition
patent, September 1987

Process for producing biodiesel fuel products
patent, August 2010

Enhancement of Enantioselectivity by Altering Alcohol Concentration for Esterification in Supercritical CO2.
journal, January 1999

The role of the reaction medium in lipase-catalyzed esterifications and transesterifications
journal, June 1998

Subtilisin-catalyzed transesterification in supercritical carbon dioxide
journal, September 1989

Enzymatic method for preparing transesterified oils
patent, February 1994

Lipase-catalyzed alcoholysis with supercritical carbon dioxide extraction 2: Phase behavior
journal, November 1997

Internal Mass Transfer Limitation During Enzymatic Esterification in Supercritical Carbon Dioxide and Hexane
journal, January 1995

Method for producing fatty acid alcohol ester
patent, April 2005

Process for production of fatty acid methyl esters from fatty acid triglycerides
patent, March 2004

Process for the production of fatty acid alkyl esters
patent, June 2002

Process for apparatus for the recovery of fats and oils
patent, June 1987

Processes for the separatin of lipids
patent, June 1998

Transesterification between triolein and ethylbehenate by immobilized lipase in supercritical carbon dioxide
journal, January 1996

Lipase-catalysed esterification in supercritical carbon dioxide and in hexane
journal, February 1997

Enzymatic interesterification in supercritical carbon dioxide.
journal, January 1988

Promotion of lipase-catalyzed esterification of N-valeric acid and citronellol in supercritical carbon dioxide in the near-critical region.
journal, January 1996

Alcoholysis and Glyceride Synthesis with Immobilized Lipase on Controlled-Pore Glass of Varying Hydrophobicity in Supercritical Carbon Dioxide
journal, April 1998

Improved process for the production of esters from fatty substances having a natural origin
patent, June 1995

Method for purifying alcohol esters
patent, June 1995

Continuous synthesis of ethyl myristate by enzymatic reaction in supercritical carbon dioxide
journal, June 1993

Supercritical Biocatalysis
journal, February 1999

Biodiesel fuel
patent, November 1996

Biodiesel fuels from vegetable oils via catalytic and non-catalytic supercritical alcohol transesterifications and other methods: a survey
journal, August 2003

Production of biodiesel using expanded gas solvents
patent, April 2009

Process for production of esters for use as a diesel fuel substitute using a non-alkaline catalyst
patent, June 1996

Simple quantitative transesterification of lipids 1. introduction
journal, January 1996

Gas oil composition
patent, February 1997

Reactions in supercritical fluids - a review
journal, January 1986

Liquid and supercritical carbon dioxide as organic solvents
journal, December 1984

Biodiesel fuel from rapeseed oil as prepared in supercritical methanol
journal, January 2001

Process for the pre-esterification of free fatty acids in fats and oils
patent, October 1987

Biodiesel from vegetable oils via transesterification in supercritical methanol
journal, November 2002

Methanolysis of seed oils in flowing supercritical carbon dioxide
journal, March 1996

Method for removing impurities from an impurity-containing fluid stream
patent, April 2010

Kinetics of transesterification in rapeseed oil to biodiesel fuel as treated in supercritical methanol
journal, April 2001

System for use of land fills and recyclable materials
patent, January 2009

Ester synthesis in lipase-catalyzed reactions
journal, November 1998

Process parameters influencing ethanolysis of cod liver oil in supercritical carbon dioxide
journal, March 1998

Enantioselective Esterification of 2-Arylpropionic Acids Catalyzed by Immobilized Rhizomucor miehei Lipase
journal, March 1997

Biodiesel production: a review
journal, October 1999

Process for regenerating adsorbents with supercritical fluids
patent, November 1978

Preparation of secondary ether fatty acids and esters from their hydroxy fatty acid equivalents
patent, March 2001

Biodiesel fuel production by transesterification of oils
journal, January 2001

Esterification of decanoic acid during supercritical fluid extraction employing either methanol-modified carbon dioxide or a methanol trap
journal, October 1999

Fuels as solvents for the conduct of enzymatic reactions
patent, December 1997

Process for preparing alkyl esters of fatty acids from fats and oils
patent, September 2001

Process for extracting and desolventizing natural oil-containing food products with minimum structural damage
patent, July 1998

Enzymatic Reaction in Supercritical Fluid Carbon Dioxide Using Dry-Ice
journal, October 1999

Enzymatic catalysis in supercritical carbon dioxide: Comparison of different lipases and a novel esterase
journal, January 1996

Enzymatic methods for polyunsaturated fatty acid enrichment
patent, March 2003

Heavy oil upgrading process
patent, February 2003

Method for fractionating cooking oil
patent, October 2004

Method for extraction and reaction using supercritical fluids
patent, September 2001

Three-stage process for deasphalting resid, removing fines from decanted oil and apparatus therefor
patent, June 1992

Chemical Reactions in Supercritical Fluids. [超臨界流体中における化学反応]
journal, January 1995

Lipase Catalysed Esterification at High Pressure
journal, January 1994

Enzymatic synthesis of oleyl oleate in dense fluids
journal, November 1995

Process for the transesterification of triglycerides in an aqueous microemulsion reaction medium in the presence of lipase enzyme
patent, June 1989

Means for and methods of deasphalting low sulfur and hydrotreated resids
patent, September 1993

Method of extraction and purification of polyunsaturated fatty acids from natural sources
patent, December 1988