CA1059062A - Procede d'electrolyse par membrane d'halogenures alcalino-metalliques - Google Patents

Procede d'electrolyse par membrane d'halogenures alcalino-metalliques

Info

Publication number: CA1059062A
Authority: CA; Canada
Prior art keywords: compound; alkali metal; weight; hydroxystyrene; graft copolymer
Prior art date: 1974-01-11
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

Application number

CA217,759A

Other languages

English (en)

Other versions

CA217759S (en

Inventor

Makoto Mukai

Kaoru Miyoshi

Kinya Tawara

Akio Sugishita

Asao Takahashi

Koichi Asano

Hiroshi Fujiwara

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.)

Cosmo Oil Co Ltd

Original Assignee

Maruzen Oil Co Ltd

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.)

1974-01-11

Filing date

1975-01-10

Publication date

1979-07-24

1974-01-11 Priority claimed from JP637574A external-priority patent/JPS537159B2/ja

1974-10-21 Priority claimed from JP12122974A external-priority patent/JPS5146599A/ja

1975-01-10 Application filed by Maruzen Oil Co Ltd filed Critical Maruzen Oil Co Ltd

1979-07-24 Application granted granted Critical

1979-07-24 Publication of CA1059062A publication Critical patent/CA1059062A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 48
238000005868 electrolysis reaction Methods 0.000 title claims abstract description 42
229910001508 alkali metal halide Inorganic materials 0.000 title claims abstract description 12
150000008045 alkali metal halides Chemical class 0.000 title claims abstract description 12
-1 hydroxystyrene compound Chemical class 0.000 claims abstract description 112
229920000578 graft copolymer Polymers 0.000 claims abstract description 53
229920000098 polyolefin Polymers 0.000 claims abstract description 29
JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims abstract description 24
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 17
239000003014 ion exchange membrane Substances 0.000 claims abstract description 10
239000012528 membrane Substances 0.000 claims description 51
239000000243 solution Substances 0.000 claims description 44
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 43
239000004698 Polyethylene Substances 0.000 claims description 32
229920000573 polyethylene Polymers 0.000 claims description 29
229920000642 polymer Polymers 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 19
239000007864 aqueous solution Substances 0.000 claims description 13
XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 claims description 11
239000004743 Polypropylene Substances 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 7
229920001155 polypropylene Polymers 0.000 claims description 7
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 5
239000004793 Polystyrene Substances 0.000 claims description 5
229920002223 polystyrene Polymers 0.000 claims description 5
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 3
OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 2
VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 claims description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 claims description 2
LUSCNZBJFBNVDT-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxy)cyclohexyl]oxymethyl]oxirane Chemical compound C1OC1COC1(OCC2OC2)CCCCC1 LUSCNZBJFBNVDT-UHFFFAOYSA-N 0.000 claims description 2
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
239000001361 adipic acid Substances 0.000 claims description 2
235000011037 adipic acid Nutrition 0.000 claims description 2
PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 claims description 2
HXTYZWJVMWWWDK-UHFFFAOYSA-N cyclohexane-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1CCC(C(Cl)=O)CC1 HXTYZWJVMWWWDK-UHFFFAOYSA-N 0.000 claims description 2
125000005442 diisocyanate group Chemical group 0.000 claims description 2
239000003822 epoxy resin Substances 0.000 claims description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
229920000647 polyepoxide Polymers 0.000 claims description 2
230000008961 swelling Effects 0.000 claims description 2
LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims 1
BKUZZZJNRDDTRP-UHFFFAOYSA-N 2-phenylethene-1,1-diol Chemical compound OC(O)=CC1=CC=CC=C1 BKUZZZJNRDDTRP-UHFFFAOYSA-N 0.000 claims 1
229920006109 alicyclic polymer Polymers 0.000 claims 1
229910000000 metal hydroxide Inorganic materials 0.000 claims 1
150000004692 metal hydroxides Chemical class 0.000 claims 1
125000001174 sulfone group Chemical group 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 69
210000000188 diaphragm Anatomy 0.000 description 55
239000011780 sodium chloride Substances 0.000 description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
239000000203 mixture Substances 0.000 description 22
239000000178 monomer Substances 0.000 description 20
229940116441 divinylbenzene Drugs 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000010894 electron beam technology Methods 0.000 description 17
FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical group OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
230000005865 ionizing radiation Effects 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
125000002091 cationic group Chemical group 0.000 description 13
230000007062 hydrolysis Effects 0.000 description 13
238000006460 hydrolysis reaction Methods 0.000 description 13
235000019441 ethanol Nutrition 0.000 description 12
FBTSUTGMWBDAAC-UHFFFAOYSA-N 3,4-Dihydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1O FBTSUTGMWBDAAC-UHFFFAOYSA-N 0.000 description 11
239000003708 ampul Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
229920001577 copolymer Polymers 0.000 description 10
239000011521 glass Substances 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
BGDWDFVUSUCDHI-UHFFFAOYSA-N (2-acetyloxy-4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1OC(C)=O BGDWDFVUSUCDHI-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000004132 cross linking Methods 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
150000001768 cations Chemical class 0.000 description 7
238000007334 copolymerization reaction Methods 0.000 description 7
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 7
239000000347 magnesium hydroxide Substances 0.000 description 7
229910001862 magnesium hydroxide Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229910001413 alkali metal ion Inorganic materials 0.000 description 6
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 6
238000005341 cation exchange Methods 0.000 description 6
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
125000000542 sulfonic acid group Chemical group 0.000 description 6
JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
150000005690 diesters Chemical class 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
239000011259 mixed solution Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
230000001133 acceleration Effects 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000010439 graphite Substances 0.000 description 3
229910002804 graphite Inorganic materials 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
229940032007 methylethyl ketone Drugs 0.000 description 3
230000035699 permeability Effects 0.000 description 3
230000008569 process Effects 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000007789 sealing Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
150000007824 aliphatic compounds Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
239000010425 asbestos Substances 0.000 description 2
229920005601 base polymer Polymers 0.000 description 2
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910021645 metal ion Inorganic materials 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000004926 polymethyl methacrylate Substances 0.000 description 2
229910052895 riebeckite Inorganic materials 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000032258 transport Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
ZOHODTKFFQCZBB-UHFFFAOYSA-N (2-benzoyloxy-4-ethenylphenyl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC=1C=C(C=C)C=CC1OC(C1=CC=CC=C1)=O ZOHODTKFFQCZBB-UHFFFAOYSA-N 0.000 description 1
QXGUWGLDQVDRAL-UHFFFAOYSA-N (2-butanoyloxy-4-ethenylphenyl) butanoate Chemical compound C(CCC)(=O)OC=1C=C(C=C)C=CC1OC(CCC)=O QXGUWGLDQVDRAL-UHFFFAOYSA-N 0.000 description 1
OWTJYMHZFCHOBI-UHFFFAOYSA-N (3-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C=C)=C1 OWTJYMHZFCHOBI-UHFFFAOYSA-N 0.000 description 1
XEVHWEXNRLKSEO-UHFFFAOYSA-N (4-ethenyl-2-propanoyloxyphenyl) propanoate Chemical compound C(CC)(=O)OC=1C=C(C=C)C=CC1OC(CC)=O XEVHWEXNRLKSEO-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000001334 alicyclic compounds Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000007872 degassing Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
230000005611 electricity Effects 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000010408 film Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
PUYCICVJCRLABY-UHFFFAOYSA-N heptane;oxolane Chemical compound C1CCOC1.CCCCCCC PUYCICVJCRLABY-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000037427 ion transport Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
YLJRCXSSKLWCDE-UHFFFAOYSA-N methyl ethanesulfonate Chemical compound CCS(=O)(=O)OC YLJRCXSSKLWCDE-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
229910000367 silver sulfate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
- C08J5/2268—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds, and by reactions not involving this type of bond
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
- C08J2333/12—Homopolymers or copolymers of methyl methacrylate

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Manufacturing & Machinery (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Materials Engineering (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)

CA217,759A 1974-01-11 1975-01-10 Procede d'electrolyse par membrane d'halogenures alcalino-metalliques Expired CA1059062A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP637574A JPS537159B2 (fr)	1974-01-11	1974-01-11
JP12122974A JPS5146599A (ja)	1974-10-21	1974-10-21	Kakumakudenkaiho

Publications (1)

Publication Number	Publication Date
CA1059062A true CA1059062A (fr)	1979-07-24

Family

ID=26340495

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA217,759A Expired CA1059062A (fr)	1974-01-11	1975-01-10	Procede d'electrolyse par membrane d'halogenures alcalino-metalliques

Country Status (12)

Country	Link
AR (1)	AR205916A1 (fr)
AU (1)	AU472578B2 (fr)
BR (1)	BR7500166A (fr)
CA (1)	CA1059062A (fr)
DD (1)	DD115639A5 (fr)
DE (1)	DE2500753C3 (fr)
ES (1)	ES433655A1 (fr)
FI (1)	FI380374A7 (fr)
FR (1)	FR2257709B1 (fr)
GB (1)	GB1460400A (fr)
IN (1)	IN140452B (fr)
IT (1)	IT1032201B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5414596B2 (fr) *	1974-02-04	1979-06-08
WO2007127225A2 (fr) *	2006-04-25	2007-11-08	Purdue Research Foundation	Compositions polymériques réticulables
US8759465B2 (en) *	2006-04-25	2014-06-24	Purdue Research Foundation	Cross-linkable polymeric compositions
CN102839389B (zh) *	2012-09-26	2015-06-03	兰州交通大学	一种膜法金属氯化物电积精炼生产方法

1974
- 1974-12-31 FI FI3803/74A patent/FI380374A7/fi unknown
1975
- 1975-01-01 AR AR257245A patent/AR205916A1/es active
- 1975-01-08 GB GB75075A patent/GB1460400A/en not_active Expired
- 1975-01-09 AU AU77206/75A patent/AU472578B2/en not_active Expired
- 1975-01-09 IT IT47590/75A patent/IT1032201B/it active
- 1975-01-09 ES ES433655A patent/ES433655A1/es not_active Expired
- 1975-01-10 BR BR166/75A patent/BR7500166A/pt unknown
- 1975-01-10 FR FR7500738A patent/FR2257709B1/fr not_active Expired
- 1975-01-10 IN IN64/CAL/1975A patent/IN140452B/en unknown
- 1975-01-10 DD DD183596A patent/DD115639A5/xx unknown
- 1975-01-10 CA CA217,759A patent/CA1059062A/fr not_active Expired
- 1975-01-10 DE DE2500753A patent/DE2500753C3/de not_active Expired

Also Published As

Publication number	Publication date
ES433655A1 (es)	1977-02-16
FR2257709B1 (fr)	1980-02-22
IT1032201B (it)	1979-05-30
FI380374A7 (fr)	1975-07-12
DE2500753A1 (de)	1975-07-17
DE2500753C3 (de)	1979-04-26
FR2257709A1 (fr)	1975-08-08
DE2500753B2 (de)	1978-08-24
DD115639A5 (fr)	1975-10-12
GB1460400A (en)	1977-01-06
AU472578B2 (en)	1976-05-27
AU7720675A (en)	1976-05-27
IN140452B (fr)	1976-11-13
BR7500166A (pt)	1975-11-04
AR205916A1 (es)	1976-06-15

Publication	Publication Date	Title
EP0032021B1 (fr)	1985-03-27	Résine échangeuse de cations et sa production, membrane permsélective à base de celle-ci, et procédé de production d'une membrane
US4605685A (en)	1986-08-12	Method for preparation of graft polymeric membranes
US4169023A (en)	1979-09-25	Electrolytic diaphragms, and method of electrolysis using the same
CA1094982A (fr)	1981-02-03	Membrane bipolaire a rendement eleve et a pellicule unique
US4506035A (en)	1985-03-19	Microporous hydrophilic fluoropolymer membranes and method
CA1046457A (fr)	1979-01-16	Diaphragmes electrolytiques et mode d'electrolyse
EP0065547B1 (fr)	1986-01-15	Membrane permselective constituée d'un fluoropolymère et préparation de ladite membrane
CA1180520A (fr)	1985-01-08	Methode de production d'un diaphragme echangeur de cations, et diaphragme ainsi obtenu
US4295952A (en)	1981-10-20	Novel cationic membranes
US3970534A (en)	1976-07-20	Graft copolymer and process for preparation thereof
CA1189018A (fr)	1985-06-18	Membrane d'echange de cations, et methode de fabrication
JPS6134515B2 (fr)	1986-08-08
US4166014A (en)	1979-08-28	Electrolytic diaphragms, and method of electrolysis using the same
EP1421126B1 (fr)	2007-03-14	Procede de preparation de membranes de copolymere greffe
CA1059062A (fr)	1979-07-24	Procede d'electrolyse par membrane d'halogenures alcalino-metalliques
US4154909A (en)	1979-05-15	Process for producing cation exchange membrane by treatment of fluorinated polymer containing sulfonyl halide groups with amine and vinyl monomer
US4025401A (en)	1977-05-24	Method for diaphragm electrolysis of alkali metal halides
EP0057065B1 (fr)	1984-05-16	Fabrication d'une membrane échangeuse de cations et cellule d'électrolyse contenant cette membrane
US4011147A (en)	1977-03-08	Method for diaphragm electrolysis of alkali metal halides
US4481306A (en)	1984-11-06	Polymerization process
US3321388A (en)	1967-05-23	Process for coordinated operation of diaphragm and mercury cathode electrolytic cells
US20040016693A1 (en)	2004-01-29	Process for preparing graft copolymer membranes
KR790001977B1 (ko)	1979-12-30	알카리금속 할로겐화물의 격막 전기분해법
SU845791A3 (ru)	1981-07-07	Способ получени диафрагмы дл элЕКТРОлизА
CA1186277A (fr)	1985-04-30	Membranes fluoropolymeriques obtenues par rayonnement et traitement a l'acide carboxylique fluore