JPS60210992A - ハイドロキノンの製造方法 - Google Patents
ハイドロキノンの製造方法Info
- Publication number
- JPS60210992A JPS60210992A JP6515584A JP6515584A JPS60210992A JP S60210992 A JPS60210992 A JP S60210992A JP 6515584 A JP6515584 A JP 6515584A JP 6515584 A JP6515584 A JP 6515584A JP S60210992 A JPS60210992 A JP S60210992A
- Authority
- JP
- Japan
- Prior art keywords
- hydroquinone
- phenol
- reaction
- mycobacterium
- benzene
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title abstract description 52
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 241000186359 Mycobacterium Species 0.000 claims abstract description 16
- 230000001580 bacterial effect Effects 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 10
- 238000012258 culturing Methods 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052799 carbon Inorganic materials 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 6
- 241000583557 Mycobacterium album Species 0.000 abstract description 5
- 230000001590 oxidative effect Effects 0.000 abstract description 5
- 241000894006 Bacteria Species 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- 241000187644 Mycobacterium vaccae Species 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000006228 supernatant Substances 0.000 description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000006285 cell suspension Substances 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241001669680 Dormitator maculatus Species 0.000 description 1
- 241000589354 Methylosinus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- -1 n-butanol Chemical compound 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6515584A JPS60210992A (ja) | 1984-04-03 | 1984-04-03 | ハイドロキノンの製造方法 |
| US06/703,307 US4824780A (en) | 1984-04-03 | 1985-02-20 | Method for producing hydroquinone |
| EP85301262A EP0158424B1 (en) | 1984-04-03 | 1985-02-25 | Method for producing hydroquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6515584A JPS60210992A (ja) | 1984-04-03 | 1984-04-03 | ハイドロキノンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60210992A true JPS60210992A (ja) | 1985-10-23 |
| JPS6246158B2 JPS6246158B2 (enrdf_load_stackoverflow) | 1987-09-30 |
Family
ID=13278703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6515584A Granted JPS60210992A (ja) | 1984-04-03 | 1984-04-03 | ハイドロキノンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60210992A (enrdf_load_stackoverflow) |
-
1984
- 1984-04-03 JP JP6515584A patent/JPS60210992A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6246158B2 (enrdf_load_stackoverflow) | 1987-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS58190394A (ja) | Ｄ−グルコ−ソンの製造方法 | |
| JPS63273486A (ja) | １−（４−メトキシフェニル）−２−アミノプロパンの製法 | |
| JPS6360999B2 (enrdf_load_stackoverflow) | ||
| JPS60210992A (ja) | ハイドロキノンの製造方法 | |
| US4824780A (en) | Method for producing hydroquinone | |
| JPS60145095A (ja) | 固定化微生物によるキシリト−ルの製造法 | |
| JPS6246157B2 (enrdf_load_stackoverflow) | ||
| JPH0424992B2 (enrdf_load_stackoverflow) | ||
| JPH0157959B2 (enrdf_load_stackoverflow) | ||
| JPS5943157B2 (ja) | ピキア属菌によるソルビト−ルの製造法 | |
| JPS6178394A (ja) | ハイドロキノンの製造方法 | |
| JPS5953838B2 (ja) | β−ヒドロキシ吉草酸の製造方法 | |
| JPH04341195A (ja) | 光学活性マンデル酸の製法 | |
| JPH047677B2 (enrdf_load_stackoverflow) | ||
| JPH01228490A (ja) | 糖リン酸の製造方法 | |
| JPH047678B2 (enrdf_load_stackoverflow) | ||
| JPS6125492A (ja) | エポキシ有機酸またはそのエステルの製造方法 | |
| JPH06261777A (ja) | 酵素法によるインジゴの製造方法 | |
| JPS5953839B2 (ja) | （−）−α−ヒドロキシメチル酪酸の製造方法 | |
| JPH0759582A (ja) | 固定化微生物によるパラヒドロキシ安息香酸の製造方法 | |
| JPS5934357B2 (ja) | 微生物によるソルビト−ルの製造法 | |
| JPS5921600B2 (ja) | Ｄ（−）−β−ヒドロキシイソ酪酸の製造方法 | |
| JPS61173789A (ja) | ４−クロロ−３−ヒドロキシ酪酸の製造法 | |
| JPH0665313B2 (ja) | トランス−４−シアノシクロヘキサン−１−カルボン酸を製造する方法 | |
| JPH0633314B2 (ja) | ニコチンアミドアデニンジヌクレオチドのアルキル化法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |