CA2037018C - Methode pour separer l'hydrogene de melanges gazeux grace a une membrane semi-permeable constituee principalement de polycarbonates derives de tetrahalogenobisphenols - Google Patents

Methode pour separer l'hydrogene de melanges gazeux grace a une membrane semi-permeable constituee principalement de polycarbonates derives de tetrahalogenobisphenols Download PDF

Info

Publication number: CA2037018C
Authority: CA; Canada
Prior art keywords: membrane; hydrogen; weight percent; bisphenol; pressure side
Prior art date: 1991-02-25
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.): Expired - Fee Related

Application number

CA 2037018

Other languages

English (en)

Other versions

CA2037018A1 (fr

Inventor

Edgar S. Sanders, Jr.

Dana C. Overman, Iii

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.)

MG Generon Inc

Original Assignee

Dow Chemical Co

MG Generon Inc

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.)

1991-02-25

Filing date

1991-02-25

Publication date

2000-11-14

1991-02-25 Application filed by Dow Chemical Co, MG Generon Inc filed Critical Dow Chemical Co

1991-02-25 Priority to CA 2037018 priority Critical patent/CA2037018C/fr

1992-08-26 Publication of CA2037018A1 publication Critical patent/CA2037018A1/fr

2000-11-14 Application granted granted Critical

2000-11-14 Publication of CA2037018C publication Critical patent/CA2037018C/fr

2011-02-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000012528 membrane Substances 0.000 title claims abstract description 146
239000007789 gas Substances 0.000 title claims abstract description 55
239000001257 hydrogen Substances 0.000 title claims abstract description 46
229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 46
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 34
239000000203 mixture Substances 0.000 title claims abstract description 34
238000000034 method Methods 0.000 title claims abstract description 29
239000004417 polycarbonate Substances 0.000 title claims abstract description 29
229920000515 polycarbonate Polymers 0.000 title claims abstract description 28
230000008569 process Effects 0.000 title claims abstract description 25
238000000926 separation method Methods 0.000 claims description 37
229930185605 Bisphenol Natural products 0.000 claims description 31
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 25
229920000642 polymer Polymers 0.000 claims description 24
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
229910052794 bromium Inorganic materials 0.000 claims description 23
229930195733 hydrocarbon Natural products 0.000 claims description 22
230000035699 permeability Effects 0.000 claims description 21
239000000460 chlorine Substances 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
239000012466 permeate Substances 0.000 claims description 14
150000002430 hydrocarbons Chemical class 0.000 claims description 13
239000004215 Carbon black (E152) Substances 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 abstract 1
239000012510 hollow fiber Substances 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
239000002131 composite material Substances 0.000 description 9
230000004907 flux Effects 0.000 description 9
239000002904 solvent Substances 0.000 description 9
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 8
238000012360 testing method Methods 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
238000005266 casting Methods 0.000 description 6
239000012530 fluid Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000000835 fiber Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000001294 propane Substances 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
229920002492 poly(sulfone) Polymers 0.000 description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
238000001125 extrusion Methods 0.000 description 3
238000009432 framing Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000011148 porous material Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
230000006978 adaptation Effects 0.000 description 2
238000000137 annealing Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
-1 polyim.ides Polymers 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229920003235 aromatic polyamide Polymers 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000009749 continuous casting Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920005597 polymer membrane Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Landscapes

Separation Using Semi-Permeable Membranes (AREA)

CA 2037018 1991-02-25 1991-02-25 Methode pour separer l'hydrogene de melanges gazeux grace a une membrane semi-permeable constituee principalement de polycarbonates derives de tetrahalogenobisphenols Expired - Fee Related CA2037018C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2037018 CA2037018C (fr)	1991-02-25	1991-02-25	Methode pour separer l'hydrogene de melanges gazeux grace a une membrane semi-permeable constituee principalement de polycarbonates derives de tetrahalogenobisphenols

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2037018 CA2037018C (fr)	1991-02-25	1991-02-25	Methode pour separer l'hydrogene de melanges gazeux grace a une membrane semi-permeable constituee principalement de polycarbonates derives de tetrahalogenobisphenols

Publications (2)

Publication Number	Publication Date
CA2037018A1 CA2037018A1 (fr)	1992-08-26
CA2037018C true CA2037018C (fr)	2000-11-14

Family

ID=4147057

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2037018 Expired - Fee Related CA2037018C (fr)	1991-02-25	1991-02-25	Methode pour separer l'hydrogene de melanges gazeux grace a une membrane semi-permeable constituee principalement de polycarbonates derives de tetrahalogenobisphenols

Country Status (1)

Country	Link
CA (1)	CA2037018C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114370596B (zh) *	2021-12-08	2023-07-14	中国航空工业集团公司北京长城计量测试技术研究所	一种提升碱金属纯度的气室及实现方法

1991
- 1991-02-25 CA CA 2037018 patent/CA2037018C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2037018A1 (fr)	1992-08-26

Legal Events

Date	Code	Title	Description
1998-01-13	EEER	Examination request
2006-02-27	MKLA	Lapsed

Publication	Publication Date	Title
EP0422885B1 (fr)	1994-08-31	Membranes de séparation de gaz à base de polyimides renfermant un motif phénylindane
Robeson et al.	1994	High performance polymers for membrane separation
US7025804B2 (en)	2006-04-11	Method for separating hydrocarbon-containing gas mixtures using hydrocarbon-resistant membranes
US4818254A (en)	1989-04-04	Semi-permeable membranes consisting predominantly of polycarbonates derived from tetrahalobisphenols
US4874401A (en)	1989-10-17	Gas separation membranes from bisphenol AF polycarbonates and polyestercarbonates
EP0336535A1 (fr)	1989-10-11	Séparation de gaz au moyen de membranes composites gonflées de solvant
US4717395A (en)	1988-01-05	Gas separations using membranes comprising sulphonated polyether sulphone
US4631075A (en)	1986-12-23	Composite membrane for gas separation
US4710204A (en)	1987-12-01	Polyphosphazene gas separation membranes
EP0500974B1 (fr)	1995-08-09	Procédé pour la séparation d'hydrogène de mixtures de gaz utilisant une membrane semi-perméable composée principalement de polycarbonates dérivés de tétrahalobisphénols
US20040025689A1 (en)	2004-02-12	Novel block polyester-ether gas separation membranes
EP0242147B1 (fr)	1992-09-02	L'application de membranes semiperméables, contenant un polycarbonate, dans la séparation d'un produit gazeux.
US4783202A (en)	1988-11-08	Polyphosphazene membrane separation of polar from non-polar fluids
US5393323A (en)	1995-02-28	Aromatic polyethersulfone gas separation membranes
US5030252A (en)	1991-07-09	Novel benzotrifluoride aryl ether gas separation membranes
EP0427897A1 (fr)	1991-05-22	Séparation de gaz
US5688307A (en)	1997-11-18	Separation of low-boiling gases using super-glassy membranes
CA2037018C (fr)	2000-11-14	Methode pour separer l'hydrogene de melanges gazeux grace a une membrane semi-permeable constituee principalement de polycarbonates derives de tetrahalogenobisphenols
US5209848A (en)	1993-05-11	Xylylene based polyether membranes for gas separation
US5034034A (en)	1991-07-23	Novel aryl carbonate cyanoaryl ether gas separation membranes
US5152811A (en)	1992-10-06	Meta, para-bisphenol based polymer gas separation membranes
JP4494222B2 (ja)	2010-06-30	パラフィンとの混合物からオレフィンを分離する方法
US5178649A (en)	1993-01-12	Poly(arylene ether ketimine) gas separation membranes
DE69112023T2 (de)	1996-01-04	Verfahren zur Abtrennung von Wasserstoff aus Gasgemischen unter Verwendung einer teildurchlässigen Membran, die vorwiegend aus von Tetrahalobisphenolen stammenden Polykarbonaten besteht.
EP0652043A2 (fr)	1995-05-10	Membranes de séparation de gaz en polyéthercétone aromatique