JPS6247517B2 - - Google Patents

Info

Publication number: JPS6247517B2
Authority: JP; Japan
Prior art keywords: reaction; hydroquinone; phenol; benzene; methanol
Prior art date: 1984-09-26
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

JP19954284A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6178394A (ja

Inventor

Akira Yoshikawa

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.)

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

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.)

1984-09-26

Filing date

1984-09-26

Publication date

1987-10-08

1984-09-26 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1984-09-26 Priority to JP19954284A priority Critical patent/JPS6178394A/ja

1986-04-21 Publication of JPS6178394A publication Critical patent/JPS6178394A/ja

1987-10-08 Publication of JPS6247517B2 publication Critical patent/JPS6247517B2/ja

Status Granted legal-status Critical Current

Links

QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 44
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
230000001580 bacterial effect Effects 0.000 claims description 15
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
238000012258 culturing Methods 0.000 claims description 7
244000005700 microbiome Species 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
102000004190 Enzymes Human genes 0.000 claims description 5
108090000790 Enzymes Proteins 0.000 claims description 5
230000001590 oxidative effect Effects 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 33
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
238000000034 method Methods 0.000 description 9
239000006228 supernatant Substances 0.000 description 7
241000894006 Bacteria Species 0.000 description 6
239000006227 byproduct Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
239000000758 substrate Substances 0.000 description 6
238000005119 centrifugation Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000007787 solid Substances 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
241000589349 Methylosinus sporium Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000012136 culture method Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material 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
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000589346 Methylococcus capsulatus Species 0.000 description 1
241000589354 Methylosinus Species 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
JERCPDZTVRGVSH-UHFFFAOYSA-N benzene-1,2-diol;benzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1.OC1=CC=CC=C1O JERCPDZTVRGVSH-UHFFFAOYSA-N 0.000 description 1
238000002306 biochemical method Methods 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229960002413 ferric citrate Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
238000009630 liquid culture Methods 0.000 description 1
239000013028 medium composition Substances 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000002525 ultrasonication Methods 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

JP19954284A 1984-09-26 1984-09-26 ハイドロキノンの製造方法 Granted JPS6178394A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP19954284A JPS6178394A (ja)	1984-09-26	1984-09-26	ハイドロキノンの製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP19954284A JPS6178394A (ja)	1984-09-26	1984-09-26	ハイドロキノンの製造方法

Publications (2)

Publication Number	Publication Date
JPS6178394A JPS6178394A (ja)	1986-04-21
JPS6247517B2 true JPS6247517B2 (ko)	1987-10-08

Family

ID=16409553

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP19954284A Granted JPS6178394A (ja)	1984-09-26	1984-09-26	ハイドロキノンの製造方法

Country Status (1)

Country	Link
JP (1)	JPS6178394A (ko)

1984
- 1984-09-26 JP JP19954284A patent/JPS6178394A/ja active Granted

Also Published As

Publication number	Publication date
JPS6178394A (ja)	1986-04-21

Legal Events

Date	Code	Title	Description
2004-09-26	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
JP2676568B2 (ja)	1997-11-17	Ｒ（−）−マンデル酸およびその誘導体の製造法
JP4197754B2 (ja)	2008-12-17	乳酸又はコハク酸の製造方法
KR100274552B1 (ko)	2000-12-15	피루브산의 제조 방법
IE832505L (en)	1984-04-27	Microbial production of indigo
JPH06237789A (ja)	1994-08-30	フェニル基を有する光学活性α−ヒドロキシカルボン酸の製造法
FI86889B (fi)	1992-07-15	Foerfarande foer framstaellning av l-karnitin pao mikrobiologiskt saett.
JPH0342074B2 (ko)	1991-06-26
AU2008249370B2 (en)	2013-09-05	Method for producing glucuronic acid by glucuronic acid fermentation
FR2461753A1 (fr)	1981-02-06	Procede de preparation d'une cephalosporine par fermentation et micro-organisme destine a la mise en oeuvre de ce procede
JPS6247517B2 (ko)	1987-10-08
US4824780A (en)	1989-04-25	Method for producing hydroquinone
JPH0588105B2 (ko)	1993-12-21
JPS6246157B2 (ko)	1987-09-30
JPH03191795A (ja)	1991-08-21	微生物処理によるｓ―（＋）―３―ハロゲノ―１，２―プロパンジオールの製法
JPH04218385A (ja)	1992-08-07	Ｒ（−）−マンデル酸の製造法
US3297545A (en)	1967-01-10	Preparation and recovery of hydrogen
JPH0475760B2 (ko)	1992-12-01
JPS6246158B2 (ko)	1987-09-30
JPS58116690A (ja)	1983-07-11	Ｄ−β−ヒドロキシアミノ酸の製造法
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JPS6125492A (ja)	1986-02-04	エポキシ有機酸またはそのエステルの製造方法
JPH02207793A (ja)	1990-08-17	Ｄ―β―ヒドロキシアミノ酸の製造法