JPH0317819B2 - - Google Patents
Info
- Publication number
- JPH0317819B2 JPH0317819B2 JP182087A JP182087A JPH0317819B2 JP H0317819 B2 JPH0317819 B2 JP H0317819B2 JP 182087 A JP182087 A JP 182087A JP 182087 A JP182087 A JP 182087A JP H0317819 B2 JPH0317819 B2 JP H0317819B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- ceric
- naphthoquinone
- aqueous solution
- nitronaphthalene
- 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
- 239000007864 aqueous solution Substances 0.000 claims description 31
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 claims description 30
- VSBOSAGJYNRBJN-UHFFFAOYSA-N 5-nitronaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2[N+](=O)[O-] VSBOSAGJYNRBJN-UHFFFAOYSA-N 0.000 claims description 22
- 150000002500 ions Chemical class 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 44
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 230000001376 precipitating effect Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- 229910017604 nitric acid Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229930192627 Naphthoquinone Natural products 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 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 4
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 4
- 150000002791 naphthoquinones Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- -1 Cerium ion Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000000703 Cerium Chemical class 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- CBXWGGFGZDVPNV-UHFFFAOYSA-N so4-so4 Chemical compound OS(O)(=O)=O.OS(O)(=O)=O CBXWGGFGZDVPNV-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- KFIRODWJCYBBHY-UHFFFAOYSA-N 3-nitrophthalic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1C(O)=O KFIRODWJCYBBHY-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- AOFSUBOXJFKGAZ-UHFFFAOYSA-O azanium nitric acid nitrate Chemical compound [NH4+].O[N+]([O-])=O.[O-][N+]([O-])=O AOFSUBOXJFKGAZ-UHFFFAOYSA-O 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LFLZOWIFJOBEPN-UHFFFAOYSA-N nitrate, nitrate Chemical compound O[N+]([O-])=O.O[N+]([O-])=O LFLZOWIFJOBEPN-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/10—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing sonic or ultrasonic vibrations
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP182087A JPS63170340A (ja) | 1987-01-09 | 1987-01-09 | ５−ニトロ−１，４−ナフトキノンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP182087A JPS63170340A (ja) | 1987-01-09 | 1987-01-09 | ５−ニトロ−１，４−ナフトキノンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63170340A JPS63170340A (ja) | 1988-07-14 |
| JPH0317819B2 true JPH0317819B2 (en]) | 1991-03-11 |
Family
ID=11512198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP182087A Granted JPS63170340A (ja) | 1987-01-09 | 1987-01-09 | ５−ニトロ−１，４−ナフトキノンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63170340A (en]) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102560527B (zh) * | 2012-02-22 | 2014-12-10 | 西南大学 | 5-硝基-1, 4-萘醌的直接电化学合成方法 |
-
1987
- 1987-01-09 JP JP182087A patent/JPS63170340A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63170340A (ja) | 1988-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS58192839A (ja) | シクロヘキサノ−ル及びシクロヘキサノンの製造方法 | |
| JP4012568B2 (ja) | ハロ置換芳香族酸の製造方法 | |
| JPH02222731A (ja) | 触媒の回収方法 | |
| JPH0317819B2 (en]) | ||
| US3917719A (en) | Process for the preparation of 4-nitro-m-cresol | |
| JPS5925779B2 (ja) | 立体異性脂環ジアミンの異性化法 | |
| JPH0434980B2 (en]) | ||
| JPH0480011B2 (en]) | ||
| JP4126729B2 (ja) | フタリド類の製造方法 | |
| JPH0417172B2 (en]) | ||
| JPS61118378A (ja) | テトラクロロフタル酸無水物の製造法 | |
| JP3927835B2 (ja) | ヨウ化芳香族化合物ジアセテートの製造方法 | |
| JPS5935907B2 (ja) | 芳香族ポリカルボン酸の製造法 | |
| JP2664761B2 (ja) | アミノベンザントロン類の製造方法 | |
| SU979327A1 (ru) | Способ получени адипиновой кислоты | |
| JPH045252A (ja) | ４，４’‐ジヒドロキシ‐３，３’，５，５’‐テトラメチルジフェニルメタンの製造方法 | |
| JPS63169394A (ja) | １−アミノアントラキノンの製造法 | |
| JPS648608B2 (en]) | ||
| JPH0788340B2 (ja) | 銅の除去法 | |
| JPH07108888B2 (ja) | オキサミドの精製法 | |
| JPH0788337B2 (ja) | ５−アミノ−２，４，６−トリヨ−ドイソフタル酸の製造方法 | |
| JPH023625A (ja) | ３−ニトロフタル酸の製造方法 | |
| JPS61215344A (ja) | モノカルボン酸モリブデンの製造方法 | |
| JPS5852255A (ja) | 不飽和アミドの製造方法 | |
| JPH02264742A (ja) | ビフェニルジカルボン酸の精製法 |