WO2017172824A1 - Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers - Google Patents
Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers Download PDFInfo
- Publication number
- WO2017172824A1 WO2017172824A1 PCT/US2017/024615 US2017024615W WO2017172824A1 WO 2017172824 A1 WO2017172824 A1 WO 2017172824A1 US 2017024615 W US2017024615 W US 2017024615W WO 2017172824 A1 WO2017172824 A1 WO 2017172824A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- membrane
- hydroxide
- piperidinium
- monomer
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 199
- 239000012528 membrane Substances 0.000 title claims abstract description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 title claims abstract description 74
- -1 Poly(aryl piperidinium Chemical compound 0.000 title claims abstract description 70
- 229920000554 ionomer Polymers 0.000 title claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 64
- 229910001868 water Inorganic materials 0.000 claims abstract description 63
- 239000000446 fuel Substances 0.000 claims abstract description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 39
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 239000002904 solvent Substances 0.000 claims abstract description 13
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 61
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 36
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 claims description 34
- 229940087189 2,2,2-trifluoroacetophenone Drugs 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000002222 fluorine compounds Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 18
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 claims description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 229920005597 polymer membrane Polymers 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003011 anion exchange membrane Substances 0.000 claims description 12
- PQVNJXLMQLJOLF-UHFFFAOYSA-N O=C1CC[N+]2(CC1)CCCCC2 Chemical compound O=C1CC[N+]2(CC1)CCCCC2 PQVNJXLMQLJOLF-UHFFFAOYSA-N 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 11
- 239000003792 electrolyte Substances 0.000 claims description 11
- 238000012360 testing method Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- IIENZDKFAYEFGJ-UHFFFAOYSA-M [I-].O=C1CC[N+]2(CC1)CCCCC2 Chemical compound [I-].O=C1CC[N+]2(CC1)CCCCC2 IIENZDKFAYEFGJ-UHFFFAOYSA-M 0.000 claims description 10
- 238000005266 casting Methods 0.000 claims description 10
- 239000002685 polymerization catalyst Substances 0.000 claims description 10
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 9
- 239000004698 Polyethylene Substances 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 9
- 239000002168 alkylating agent Substances 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229920000573 polyethylene Polymers 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000005349 anion exchange Methods 0.000 claims description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 239000012456 homogeneous solution Substances 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 230000008859 change Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- 238000009736 wetting Methods 0.000 claims description 3
- GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 claims description 2
- XBWQFDNGNOOMDZ-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F XBWQFDNGNOOMDZ-UHFFFAOYSA-N 0.000 claims description 2
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 claims description 2
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 claims description 2
- AVSVJSGDSPDFLH-UHFFFAOYSA-N 2,2,2-trifluoroethylbenzene Chemical compound FC(F)(F)CC1=CC=CC=C1 AVSVJSGDSPDFLH-UHFFFAOYSA-N 0.000 claims description 2
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 2
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 10
- 230000003247 decreasing effect Effects 0.000 abstract description 6
- 150000001768 cations Chemical class 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 38
- KINMYBBFQRSVLL-UHFFFAOYSA-N 4-(4-phenoxybutoxy)furo[3,2-g]chromen-7-one Chemical compound C1=2C=COC=2C=C2OC(=O)C=CC2=C1OCCCCOC1=CC=CC=C1 KINMYBBFQRSVLL-UHFFFAOYSA-N 0.000 description 36
- 101001104199 Homo sapiens Retinitis pigmentosa 9 protein Proteins 0.000 description 36
- 101001104198 Mus musculus Retinitis pigmentosa 9 protein homolog Proteins 0.000 description 36
- 102100040073 Retinitis pigmentosa 9 protein Human genes 0.000 description 36
- 239000000243 solution Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 0 C*(C)C(CC1)(CC*1(O)O)C(C)(C)C Chemical compound C*(C)C(CC1)(CC*1(O)O)C(C)(C)C 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229930184652 p-Terphenyl Natural products 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000000429 assembly Methods 0.000 description 2
- 230000000712 assembly Effects 0.000 description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
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- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- 239000002351 wastewater Substances 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
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- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Abstract
Description
Claims
Priority Applications (7)
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KR1020187028658A KR102380604B1 (en) | 2016-03-28 | 2017-03-28 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
EP17776496.6A EP3436186A4 (en) | 2016-03-28 | 2017-03-28 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
CA3019209A CA3019209A1 (en) | 2016-03-28 | 2017-03-28 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
JP2018550323A JP7153561B2 (en) | 2016-03-28 | 2017-03-28 | Poly(arylpiperidinium) polymers for use as hydroxide exchange membranes and hydroxide exchange ionomers |
CN201780021383.2A CN109070022B (en) | 2016-03-28 | 2017-03-28 | Poly (arylpiperidinium) polymers as hydroxide exchange membranes and ionomers |
IL262015A IL262015B (en) | 2016-03-28 | 2018-09-27 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
US16/146,887 US10290890B2 (en) | 2016-03-28 | 2018-09-28 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
Applications Claiming Priority (2)
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US201662314008P | 2016-03-28 | 2016-03-28 | |
US62/314,008 | 2016-03-28 |
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US16/146,887 Continuation US10290890B2 (en) | 2016-03-28 | 2018-09-28 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
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PCT/US2017/024615 WO2017172824A1 (en) | 2016-03-28 | 2017-03-28 | Poly(aryl piperidinium) polymers for use as hydroxide exchange membranes and ionomers |
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US (1) | US10290890B2 (en) |
EP (1) | EP3436186A4 (en) |
JP (1) | JP7153561B2 (en) |
KR (1) | KR102380604B1 (en) |
CN (1) | CN109070022B (en) |
CA (1) | CA3019209A1 (en) |
IL (1) | IL262015B (en) |
WO (1) | WO2017172824A1 (en) |
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IL262015A (en) | 2018-10-31 |
US20190036143A1 (en) | 2019-01-31 |
JP2019518809A (en) | 2019-07-04 |
EP3436186A1 (en) | 2019-02-06 |
CN109070022A (en) | 2018-12-21 |
CA3019209A1 (en) | 2017-10-05 |
KR20180121961A (en) | 2018-11-09 |
KR102380604B1 (en) | 2022-03-30 |
JP7153561B2 (en) | 2022-10-14 |
US10290890B2 (en) | 2019-05-14 |
IL262015B (en) | 2022-06-01 |
EP3436186A4 (en) | 2019-08-14 |
CN109070022B (en) | 2022-09-20 |
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