JPH022956B2 - - Google Patents
Info
- Publication number
- JPH022956B2 JPH022956B2 JP59171514A JP17151484A JPH022956B2 JP H022956 B2 JPH022956 B2 JP H022956B2 JP 59171514 A JP59171514 A JP 59171514A JP 17151484 A JP17151484 A JP 17151484A JP H022956 B2 JPH022956 B2 JP H022956B2
- Authority
- JP
- Japan
- Prior art keywords
- oxidation
- reaction
- ions
- reaction tower
- electrolytic
- Prior art date
- 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
Links
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 238000007254 oxidation reaction Methods 0.000 claims description 44
- 230000003647 oxidation Effects 0.000 claims description 42
- 150000002500 ions Chemical class 0.000 claims description 38
- -1 quinone compound Chemical class 0.000 claims description 30
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 28
- 150000001491 aromatic compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 25
- 239000003960 organic solvent Substances 0.000 claims description 8
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical group O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 16
- 230000008569 process Effects 0.000 description 16
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 14
- 229910052684 Cerium Inorganic materials 0.000 description 13
- 238000000605 extraction Methods 0.000 description 12
- 150000004053 quinones Chemical class 0.000 description 12
- 229930192627 Naphthoquinone Natural products 0.000 description 11
- 150000002791 naphthoquinones Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 8
- 230000028161 membrane depolarization Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000005868 electrolysis reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- KOZLSUVHLWGFGS-UHFFFAOYSA-N CC1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 Chemical compound CC1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 KOZLSUVHLWGFGS-UHFFFAOYSA-N 0.000 description 1
- 108091006149 Electron carriers Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59171514A JPS6152382A (ja) | 1984-08-20 | 1984-08-20 | 芳香族化合物の酸化方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59171514A JPS6152382A (ja) | 1984-08-20 | 1984-08-20 | 芳香族化合物の酸化方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6152382A JPS6152382A (ja) | 1986-03-15 |
| JPH022956B2 true JPH022956B2 (en]) | 1990-01-19 |
Family
ID=15924530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59171514A Granted JPS6152382A (ja) | 1984-08-20 | 1984-08-20 | 芳香族化合物の酸化方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6152382A (en]) |
-
1984
- 1984-08-20 JP JP59171514A patent/JPS6152382A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6152382A (ja) | 1986-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3745180A (en) | Oxidation of organic materials | |
| JPH0356683A (ja) | エチレングリコールの同時製造と対の電気化学合成法 | |
| US4639298A (en) | Oxidation of organic compounds using ceric ions in aqueous methanesulfonic acid | |
| US3147203A (en) | Process for the production of carbonyl compounds | |
| FI80256B (fi) | Foerfarande foer oxidering av en organisk foerening. | |
| US4530745A (en) | Method for electrolyzing cerous sulfate | |
| JP2618389B2 (ja) | 水性トリフルオロメタンスルホン酸中でセリウムイオンを使用する有機化合物の酸化 | |
| JP2633244B2 (ja) | 水性有機溶液中でメタンスルホン酸セリウムを使用する有機化合物の酸化 | |
| CN112626547B (zh) | 利用超声辅助间接电合成醌类化合物的方法 | |
| EP0075828A1 (en) | Oxidizing fused ring compounds to quinones with aqueous acidic solutions of cerium | |
| JP2588695B2 (ja) | カルボニル基含有化合物の製造方法 | |
| US5213665A (en) | Process for producing 1-aminoanthraquinones | |
| US3509031A (en) | Electrochemical oxidation of phenol | |
| JPH0394085A (ja) | １―アミノアントラキノン類の製造方法 | |
| JPH022956B2 (en]) | ||
| CA2100930A1 (en) | Process for preparing a ceric ion-containing aqueous acid solution | |
| HU203110B (en) | Process for producing d-arabinose | |
| US2477579A (en) | Electrolytic process for the production of cyclohexadiene dicarboxylic acids | |
| US5149848A (en) | Process for producing 1-aminoanthraquinones | |
| JPS63270635A (ja) | １，４−ナフトキノンの製造法 | |
| JPS6157818B2 (en]) | ||
| JPS63190850A (ja) | １，４，４ａ，９ａ−テトラヒドロアントラキノンの製造法 | |
| US4457814A (en) | Process for electrochemical reduction of terephthalic acid | |
| EP0244812B1 (en) | Oxidation of organic compounds | |
| US3418224A (en) | Preparation of sulfones by electrolytic oxidation |