JPS60252445A - ２−メチル−１，４−ナフトキノンの製造方法 - Google Patents
２−メチル−１，４−ナフトキノンの製造方法Info
- Publication number
- JPS60252445A JPS60252445A JP59106235A JP10623584A JPS60252445A JP S60252445 A JPS60252445 A JP S60252445A JP 59106235 A JP59106235 A JP 59106235A JP 10623584 A JP10623584 A JP 10623584A JP S60252445 A JPS60252445 A JP S60252445A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- naphthoquinone
- solution
- aqueous
- crystals
- 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.)
- Granted
Links
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 claims abstract description 50
- OPKFWRVRCVCMJH-UHFFFAOYSA-N 6-methylnaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC(C)=CC=C21 OPKFWRVRCVCMJH-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000013078 crystal Substances 0.000 claims abstract description 41
- 239000000243 solution Substances 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 19
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 18
- 239000007864 aqueous solution Substances 0.000 claims abstract description 15
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 13
- -1 alicyclic hydrocarbon Chemical class 0.000 claims abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 239000012266 salt solution Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 23
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 12
- 229930192627 Naphthoquinone Natural products 0.000 claims description 9
- 150000002791 naphthoquinones Chemical class 0.000 claims description 9
- 230000001590 oxidative effect Effects 0.000 claims description 9
- 229940079826 hydrogen sulfite Drugs 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 239000011259 mixed solution Substances 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 235000012711 vitamin K3 Nutrition 0.000 abstract 1
- 239000011652 vitamin K3 Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 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 5
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 125000000985 2-methyl-1,4-naphthoquinonyl group Chemical group CC=1C(C2=CC=CC=C2C(C1*)=O)=O 0.000 description 1
- LUQZKEZPFQRRRK-UHFFFAOYSA-N 2-methyl-2-nitrosopropane Chemical compound CC(C)(C)N=O LUQZKEZPFQRRRK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940030225 antihemorrhagics Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002874 hemostatic agent Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- TXRWKMKFNIHNRO-UHFFFAOYSA-M sodium hydrogen sulfite sulfuric acid Chemical compound [Na+].OS([O-])=O.OS(O)(=O)=O TXRWKMKFNIHNRO-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59106235A JPS60252445A (ja) | 1984-05-25 | 1984-05-25 | ２−メチル−１，４−ナフトキノンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59106235A JPS60252445A (ja) | 1984-05-25 | 1984-05-25 | ２−メチル−１，４−ナフトキノンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60252445A true JPS60252445A (ja) | 1985-12-13 |
| JPH0417172B2 JPH0417172B2 (enrdf_load_stackoverflow) | 1992-03-25 |
Family
ID=14428457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59106235A Granted JPS60252445A (ja) | 1984-05-25 | 1984-05-25 | ２−メチル−１，４−ナフトキノンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60252445A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637741A (en) * | 1994-09-27 | 1997-06-10 | Kuraray Co., Ltd. | Process for producing 2-methyl-1,4-naphthoquinone |
| CN1837172B (zh) | 2006-03-16 | 2010-05-12 | 中钢集团鞍山热能研究院 | 制备维生素k3时分离剂的应用 |
| EP2345631A1 (en) | 2010-01-13 | 2011-07-20 | Lonza Ltd. | Yield-efficient process for the production of highly pure 2-methyl-1,4-naphthoquinone and its derivatives |
-
1984
- 1984-05-25 JP JP59106235A patent/JPS60252445A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637741A (en) * | 1994-09-27 | 1997-06-10 | Kuraray Co., Ltd. | Process for producing 2-methyl-1,4-naphthoquinone |
| CN1837172B (zh) | 2006-03-16 | 2010-05-12 | 中钢集团鞍山热能研究院 | 制备维生素k3时分离剂的应用 |
| EP2345631A1 (en) | 2010-01-13 | 2011-07-20 | Lonza Ltd. | Yield-efficient process for the production of highly pure 2-methyl-1,4-naphthoquinone and its derivatives |
| WO2011085945A1 (en) | 2010-01-13 | 2011-07-21 | Lonza Ltd | Yield-efficient process for the production of highly pure 2-methyl-1,4-naphthoquinone and its derivatives |
| US8350089B2 (en) | 2010-01-13 | 2013-01-08 | Lonza Ltd. | Yield-efficient process for the production of highly pure 2-methyl-1,4-naphthoquinone and its derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0417172B2 (enrdf_load_stackoverflow) | 1992-03-25 |
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