JPS5959642A - フエノ−ルをｐ−ベンゾキノンへ酸化する方法 - Google Patents
フエノ−ルをｐ−ベンゾキノンへ酸化する方法Info
- Publication number
- JPS5959642A JPS5959642A JP58000545A JP54583A JPS5959642A JP S5959642 A JPS5959642 A JP S5959642A JP 58000545 A JP58000545 A JP 58000545A JP 54583 A JP54583 A JP 54583A JP S5959642 A JPS5959642 A JP S5959642A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- benzoquinone
- amine
- phenol
- diethylamine
- 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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 9
- 230000003647 oxidation Effects 0.000 title description 6
- 238000007254 oxidation reaction Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical group Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 229960003280 cupric chloride Drugs 0.000 claims 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000002823 nitrates Chemical class 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 244000055346 Paulownia Species 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Chemical group 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- -1 halogen ions Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000001706 oxygenating effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
- C07C46/08—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring with molecular oxygen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/423,984 US4478752A (en) | 1981-07-20 | 1982-09-27 | Process for oxidizing phenol to p-benzoquinone |
| US423984 | 1982-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5959642A true JPS5959642A (ja) | 1984-04-05 |
| JPH0247975B2 JPH0247975B2 (cg-RX-API-DMAC7.html) | 1990-10-23 |
Family
ID=23681000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58000545A Granted JPS5959642A (ja) | 1982-09-27 | 1983-01-07 | フエノ−ルをｐ−ベンゾキノンへ酸化する方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4478752A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0105067B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5959642A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1192213A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3274545D1 (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4545937A (en) * | 1983-04-18 | 1985-10-08 | University Of Delaware | Binucleating ligand-metal complexes as oxidation catalysts |
| EP0369823B1 (en) * | 1988-11-18 | 1993-06-16 | THE STATE OF JAPAN, as Represented by the DIRECTOR GENERAL of the AGENCY of INDUSTRIAL SCIENCE and TECHNOLOGY | Method for the preparation of 2,3,5-trimethylbenzoquinone |
| US5110995A (en) * | 1991-03-12 | 1992-05-05 | Institute Of Catalysis | Preparation of phenol or phenol derivatives |
| US6872857B1 (en) * | 2003-09-29 | 2005-03-29 | Council Of Scientific And Industrial Research | Process for conversion of phenol to hydroquinone and quinones |
| CN104292096A (zh) * | 2014-09-09 | 2015-01-21 | 中国科学院青岛生物能源与过程研究所 | 一种选择催化氧化苯酚化合物制备对苯醌化合物的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5217432A (en) * | 1975-07-28 | 1977-02-09 | Du Pont | Oxidation of monoohydroxyaryl compound to 1*44quinone |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3134753A (en) * | 1958-06-24 | 1964-05-26 | Gen Electric | Oxidation of aryloxy-substituted phenols |
| US3213114A (en) * | 1962-06-19 | 1965-10-19 | Ethyl Corp | Preparation of quinones and hydroquinones |
| US3210384A (en) * | 1962-11-21 | 1965-10-05 | Gen Electric | Process for the preparation of 3, 3', 5, 5'-tetra-substituted diphenoquinone |
| US3870731A (en) * | 1973-09-28 | 1975-03-11 | Goodyear Tire & Rubber | Oxidation of phenols and alkyl substituted phenols to their corresponding para-benzoquinone |
| FR2408570A1 (fr) * | 1977-06-27 | 1979-06-08 | Rhone Poulenc Ind | Procede de preparation de para-benzoquinone |
| FR2449667A1 (fr) * | 1979-02-21 | 1980-09-19 | Rhone Poulenc Ind | Procede de preparation de para-benzoquinones |
-
1982
- 1982-09-27 US US06/423,984 patent/US4478752A/en not_active Expired - Lifetime
- 1982-11-30 CA CA000416673A patent/CA1192213A/en not_active Expired
- 1982-12-09 EP EP82306572A patent/EP0105067B1/en not_active Expired
- 1982-12-09 DE DE8282306572T patent/DE3274545D1/de not_active Expired
-
1983
- 1983-01-07 JP JP58000545A patent/JPS5959642A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5217432A (en) * | 1975-07-28 | 1977-02-09 | Du Pont | Oxidation of monoohydroxyaryl compound to 1*44quinone |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3274545D1 (en) | 1987-01-15 |
| US4478752A (en) | 1984-10-23 |
| EP0105067B1 (en) | 1986-12-03 |
| EP0105067A3 (en) | 1984-12-05 |
| EP0105067A2 (en) | 1984-04-11 |
| CA1192213A (en) | 1985-08-20 |
| JPH0247975B2 (cg-RX-API-DMAC7.html) | 1990-10-23 |
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