Amorphous fluorinated copolymer gas separation membranes
Abstract
Membranes having a permselective active layer of a copolymerized perfluorinated monomer and an non-fluorinated alkylvinylester monomer demonstrate superior selective permeability performance for separating gas mixtures compared to membranes of exclusively perfluorinated polymers. Preferred active layer compositions are copolymers of perfluoro-2,2-dimethyl-1,3 dioxole (PDD) copolymerized with an alkylvinyl ester such as vinyl acetate, and vinyl pivalate, and with alkylvinyl esters that are substantially hydrolyzed to provide copolymerized vinyl alcohol functionality. The membranes can have a thin, high diffusion rate, “gutter layer” of a fluorinated polymer highly permeable to nitrogen positioned between the active layer and a porous support layer. A novel copolymer effective in selectively permeable membranes is a copolymer of PDD and an alkylvinyl ester compound having the formula H2C═CHOC(O)R1 in which R1 is a linear or branched alkyl group of from 2 to 5 carbon atoms.
- Inventors:
- Issue Date:
- Research Org.:
- Compact Membrane Systems, Inc., Newport, DE (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1637783
- Patent Number(s):
- 10596527
- Application Number:
- 15/574,408
- Assignee:
- Compact Membrane Systems, Inc. (Newport, DE)
- Patent Classifications (CPCs):
-
B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01D - SEPARATION
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
- DOE Contract Number:
- SC0011989
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 06/10/2016
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Shangguan, Ning, Feiring, Andrew Edward, and Majumdar, Sudipto. Amorphous fluorinated copolymer gas separation membranes. United States: N. p., 2020.
Web.
Shangguan, Ning, Feiring, Andrew Edward, & Majumdar, Sudipto. Amorphous fluorinated copolymer gas separation membranes. United States.
Shangguan, Ning, Feiring, Andrew Edward, and Majumdar, Sudipto. Tue .
"Amorphous fluorinated copolymer gas separation membranes". United States. https://www.osti.gov/servlets/purl/1637783.
@article{osti_1637783,
title = {Amorphous fluorinated copolymer gas separation membranes},
author = {Shangguan, Ning and Feiring, Andrew Edward and Majumdar, Sudipto},
abstractNote = {Membranes having a permselective active layer of a copolymerized perfluorinated monomer and an non-fluorinated alkylvinylester monomer demonstrate superior selective permeability performance for separating gas mixtures compared to membranes of exclusively perfluorinated polymers. Preferred active layer compositions are copolymers of perfluoro-2,2-dimethyl-1,3 dioxole (PDD) copolymerized with an alkylvinyl ester such as vinyl acetate, and vinyl pivalate, and with alkylvinyl esters that are substantially hydrolyzed to provide copolymerized vinyl alcohol functionality. The membranes can have a thin, high diffusion rate, “gutter layer” of a fluorinated polymer highly permeable to nitrogen positioned between the active layer and a porous support layer. A novel copolymer effective in selectively permeable membranes is a copolymer of PDD and an alkylvinyl ester compound having the formula H2C═CHOC(O)R1 in which R1 is a linear or branched alkyl group of from 2 to 5 carbon atoms.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Mar 24 00:00:00 EDT 2020},
month = {Tue Mar 24 00:00:00 EDT 2020}
}
Works referenced in this record:
Gas Separation Using Organic-Vapor-Resistant Membranes and PSA
patent-application, February 2003
- Pinnau, Ingo; He, Zhenjie; Da Costa, Andre R.
- US Patent Application 10/105923; 20030033929
Shaped articles which are composed of a copolymer containing fluorine groups and which are selectively permeable to liquids and gases and are simultaneously oleophobic and oleophilic
patent, December 1985
- Walch, Axel; Seifried, Walter; Michel, Wolfgang
- US Patent Document 4,557,955
Perfluorovinyl Ether Monomer Having a Sulfonamido Group
patent-application, April 2007
- Iked, Masanori; Hoshi, Nobuto; Uematsu, Nobuyuki
- US Patent Application 11/537376; 20070088142
Polymeric membrane and process for separation of aliphatically unsaturated hydrocarbons
patent, November 1991
- Ho, W. S. Winston
- US Patent Document 5,062,866
Methods for manufacturing olefins from lower alkans by oxidative dehydrogenation
patent, February 2003
- Culp, Gary; Stricker, Vincent J.; Nelson, James R.
- US Patent Document 6,518,476
Process for Separation of Unsaturated Hydrocarbons
patent, September 1973
- Steigelmann, Edward F.; Hughes, Robert D.
- US Patent Document 3758603
Use of silver-exchanged ionomer membranes for gas separation
patent, March 1993
- Eriksen, Odd Ivar; Aksnes, Elin; Dahl, Ivar M.
- US Patent Document 5,191,151
Fluoropolymer-Based Conductive Composition
patent-application, June 2003
- Bonnet, Anthony; Court, Francois; Leibler, Ludwik
- US Patent Application 09/998932; 20030104150
Polymerization of Olefins
patent-application, May 2004
- Brookhart, Maurice S.; Johnson, Lynda Kaye; Killian, Christopher Moore
- US Patent Application 10/689301; 20040102591
Organic Fluid Permeation through Fluoropolymer Membranes
patent-application, April 2012
- Nemser, Stuart M.; Kosaraju, Praveen; Bowser, John
- US Patent Application 13/279904; 20120097612
Silver nanoparticle/polymer nanocomposite membranes for olefin/paraffin separation and method of preparing the same
patent, February 2009
- Kang, Yong Soo; Char, Kook Heon; Kang, Sang-Wook
- US Patent Document 7,491,262
Method for Forming Fluorinated Ionomers
patent-application, August 2004
- Bekiarian, Paul Gregory; Farnham, William Brown
- US Patent Application 10/478617; 20040167289
Perfluorodioxole membranes
patent, September 1991
- Nemser, Stuart M.; Roman, Ian C.
- US Patent Document 5,051,114
Process for the separation of olefins from paraffins using membranes
patent, April 2008
- Herrera, Patricio S.; Feng, Xianshe; Payzant, John Donald
- US Patent Document 7,361,800
High Toughness Hollow Fiber Membranes Based on Vinylidene Fluoride Polymers
patent-application, August 2017
- Kosar, Walter P.; Reber, Roderick; O'Brien, Gregory S.
- US Patent Application 15/328115; 20170216780
Separations with Highly Selective Fluoropolymer Membranes
patent-application, November 2011
- Campos, Daniel; Lazzeri, Jonathan; Nemser, Stuart M.
- US Patent Application 13/143081; 20110266220
Method of manufacturing fluoropolymers
patent, September 1999
- McCarthy, Thomas F.; Chen, Yan; Rainal, Eric
- US Patent Document 5,955,556
Method for producing silver salt-containing facilitated transport membrane for olefin separation having improved stability
patent, April 2005
- Kim, Hoon; Kang, Yong Soo; Lee, Byung Gwon
- US Patent Document 6,878,409
Facilitated transport membranes comprising a porous support and a solid polymer electrolyte consisting of a transition metal salt and a polymer having phthalic structure
patent, February 2007
- Kang, Yong Soo; Kim, Hoon; Kim, Jong Hak
- US Patent Document 7,179,321
The removal of hydrogen sulfide from gas streams using an aqueous metal sulfate absorbentPart I. The absorption of hydrogen sulfide in metal sulfate solutions
journal, June 2005
- Termaat, H.; Hogendoorn, J.; Versteeg, G.
- Separation and Purification Technology, Vol. 43, Issue 3
Polymeric membrane and process for separating aliphatically unsaturated hydrocarbons
patent, May 1991
- Ho, W. S. Winston
- US Patent Document 5,015,268
Silver salt-containing facilitated transport membrane for olefin separation having improved stability and method for producing the same
patent, March 2004
- Kim, Hoon; Kang, Yong Soo; Lee, Byung Gwon
- US Patent Document 6,706,771
Poly(Chlorotrifluoroethylene/Vinylidenefluoride/Vinylester) Copolymers with Excellent Long Term Ultraviolet Light Resistance
patent-application, January 2003
- McCarthy, Thomas F.
- US Patent Application 10/061674; 20030008990
Method for the preparation of ionomer films
patent, March 1988
- Martin, Charles R.; Moore, Robert B.
- US Patent Document 4,731,263
Osmotic Distillation Process
patent-application, October 2001
- Bowser, John J.
- US Patent Application 09/835550; 20010025819
Member Separation of Olefin and Paraffin Mixtures
patent-application, January 2015
- Feiring, Andrew Edward; Lazzeri, Jonathan; Majumdar, Sudipto
- US Patent Application 14/334,605; 2015/0025293 Al
Amorphous Perfluorinated Copolymers
patent-application, January 2005
- Apostolo, Marco; Triulzi, Francesco; Arcella, Vincenzo
- US Patent Application 10/913539; 20050009944
Solid state facilitated transport separation membranes using polymer electrolytes for alkene separation
patent, October 2002
- Kang, Yong Soo; Won, Jong Ok; Hong, Seong Uk
- US Patent Document 6,468,331
Membrane Separation of Ionic Liquid Solutions
patent-application, April 2015
- Campos, Daniel; Feiring, Andrew Edward; Majumdar, SUdipto
- US Patent Application 14/527732; 20150119577
Gas Separation Using Coated Membranes
patent-application, March 2004
- Pinnau, Inog; He, Zhenjie; Blanc, Rolande J.
- US Patent Application 10/612807; 20040050250
Solid polymer electrolyte material, liquid composition, solid polymer fuel cell and fluoropolymer
patent, May 2007
- Watakabe, Atsushi; Eriguchi, Takeshi; Tanuma, Toshihiro
- US Patent Document 7,220,508
Color concentrates and polymer compositions containing the same, and methods of making the same
patent, September 1997
- Scheibelhoffer, Anthony S.; Abrams, Richard L.; Dusek, Dianna B.
- US Patent Document 5,670,561
Process for Producing Fluoroionomer, Method for Purification and Concentration of the Ionomer, and Method of Film Formation
patent-application, January 2003
- Tatemoto, Masayoshi; Ino, Tadashi; Ishii, Kenji
- US Patent Application 10/182737; 20030023015
Water-free hydrocarbon separation membrane and process
patent, September 1986
- Kraus, Menahem
- US Patent Document 4,614,524