CN115569657A - Catalyst for preparing phenanthrene quinone by gas-phase oxidation of phenanthrene - Google Patents
Catalyst for preparing phenanthrene quinone by gas-phase oxidation of phenanthrene Download PDFInfo
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- CN115569657A CN115569657A CN202211283500.1A CN202211283500A CN115569657A CN 115569657 A CN115569657 A CN 115569657A CN 202211283500 A CN202211283500 A CN 202211283500A CN 115569657 A CN115569657 A CN 115569657A
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- sulfate
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- phenanthrene
- pumice
- dissolving
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000003054 catalyst Substances 0.000 title claims abstract description 38
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 230000003647 oxidation Effects 0.000 title claims abstract description 17
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 30
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000008262 pumice Substances 0.000 claims abstract description 26
- KOPBYBDAPCDYFK-UHFFFAOYSA-N caesium oxide Chemical compound [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910001942 caesium oxide Inorganic materials 0.000 claims abstract description 10
- 239000011790 ferrous sulphate Substances 0.000 claims abstract description 10
- 235000003891 ferrous sulphate Nutrition 0.000 claims abstract description 10
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims abstract description 10
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims abstract description 10
- 229940099596 manganese sulfate Drugs 0.000 claims abstract description 10
- 239000011702 manganese sulphate Substances 0.000 claims abstract description 10
- 235000007079 manganese sulphate Nutrition 0.000 claims abstract description 10
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 claims abstract description 10
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims abstract description 10
- 229910052939 potassium sulfate Inorganic materials 0.000 claims abstract description 10
- 235000011151 potassium sulphates Nutrition 0.000 claims abstract description 10
- RCIVOBGSMSSVTR-UHFFFAOYSA-L stannous sulfate Chemical compound [SnH2+2].[O-]S([O-])(=O)=O RCIVOBGSMSSVTR-UHFFFAOYSA-L 0.000 claims abstract description 10
- 229910000375 tin(II) sulfate Inorganic materials 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000012153 distilled water Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 238000005470 impregnation Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 9
- 238000005303 weighing Methods 0.000 claims description 9
- 238000004090 dissolution Methods 0.000 claims description 7
- 239000004575 stone Substances 0.000 claims description 7
- 238000007792 addition Methods 0.000 claims description 6
- 238000000975 co-precipitation Methods 0.000 claims description 6
- 230000004913 activation Effects 0.000 claims description 3
- 238000007598 dipping method Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 5
- 239000012071 phase Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 241000907903 Shorea Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical group OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000000979 synthetic dye Substances 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
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/053—Sulfates
- B01J27/055—Sulfates with alkali metals, copper, gold or silver
-
- 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
- C07C46/04—Preparation of quinones by oxidation giving rise to quinoid structures of unsubstituted ring carbon atoms in six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
Abstract
The invention relates to a catalyst for preparing phenanthrenequinone by gas phase oxidation of phenanthrene, which consists of vanadium pentoxide, potassium hydroxide, cesium oxide, ferrous sulfate, manganese sulfate, potassium sulfate, stannous sulfate and pumice, wherein the vanadium pentoxide is used as a main catalyst, the pumice is used as a carrier, and the balance is a cocatalyst, and the mass ratio of the vanadium pentoxide to the potassium hydroxide to the cesium oxide to the ferrous sulfate to the manganese sulfate to the potassium sulfate to the stannous sulfate to the pumice is = 1: 0.9: 0.3: 2: 0.02: 0.9: 0.1: 20. The catalyst can lead the yield of the phenanthrene quinone to exceed 70 percent in the phenanthrene gas-phase catalytic oxidation process, and is higher than that of the existing catalyst.
Description
Technical Field
The invention relates to a catalyst for preparing phenanthrenequinone by phenanthrene gas-phase oxidation, belonging to the technical field of chemical industry.
Background
Phenanthrenequinone is a basic organic synthetic raw material, and is mainly used as a pesticide, a plant growth regulator, a corrosion inhibitor in a magnetic recording material, a pulp preservative, a photosensitizer in photopolymerization of a high polymer material, a synthetic dye intermediate and the like.
The preparation of phenanthrenequinone by using phenanthrene as a raw material mainly comprises a liquid-phase oxidation method and a gas-phase catalytic oxidation method, wherein the gas-phase catalytic oxidation method is emphasized by many researchers due to low economic cost and environmental protection and has a tendency of replacing the liquid-phase oxidation method.
With respect to the preparation of phenanthrenequinone by gas-phase catalytic oxidation of phenanthrene as a raw material, it is described in "coal tar engineering" (2 nd edition) (P278-279) by shorea, that phenanthreneanthracene is easily oxidized, that phenanthrenequinone is produced at a low yield and by-products are abundant during oxidation, and that, for example, in U.S. patent, the mass ratio of catalyst composition is V 2 O 5 ∶K 2 SO 4 ∶SiO 2 = 10: 68: 22, yield of phenanthrenequinone is 38%. The Huadong chemical industry college adopts industrial phenanthrene as a raw material, and the self-made catalyst comprises the following components in percentage by mass: v 2 O 5 32.8%，MoO 3 10%，K 2 SO 4 7.08%，P 2 O 5 0.0354 percent, cuO0.0354 percent, niO0.24 percent, csO10.61 percent and the balance of pumice, and the yield of the phenanthrenequinone is 27.9 percent. Both catalysts give a low yield of phenanthrenequinone.
Patent zl201010225696.X reports a preparation method of a phenanthrene gas phase oxidation catalyst, wherein the main product is diphenic acid, the yield is 45-50%, and the yield of phenanthrenequinone is only 12-15%.
The yield of phenanthrene quinone prepared by gas-phase catalytic oxidation of phenanthrene is improved, the conversion rate of phenanthrene and the selectivity of phenanthrene quinone need to be considered at the same time, a catalyst needs to have certain activity, phenanthrene is converted as much as possible, deep oxidation is avoided, and the selectivity of phenanthrene quinone is reduced. The invention is a catalyst for phenanthrene gas-phase catalytic oxidation of phenanthrene quinone, which is developed on the basis of comprehensively considering the problems, vanadium pentoxide is used as a main catalyst, a plurality of auxiliary catalysts are compounded, pumice is used as a carrier, the phenanthrene conversion rate is improved, the phenanthrene selectivity is increased, and the phenanthrene quinone yield is further improved. The new catalyst is composed of eight substances of vanadium pentoxide, potassium hydroxide, cesium oxide, ferrous sulfate, manganese sulfate, potassium sulfate, stannous sulfate and pumice, and has strict mass proportion limitation, under proper operation conditions, the catalyst can enable the yield of the phenanthrenequinone to reach more than 70 percent, which is far higher than the yield level of the existing catalyst, and provides convenient conditions for subsequent purification and refining.
Disclosure of Invention
The invention aims to provide a catalyst for preparing phenanthrene quinone by gas phase oxidation of phenanthrene, which consists of eight substances, namely vanadium pentoxide, potassium hydroxide, cesium oxide, ferrous sulfate, manganese sulfate, potassium sulfate, stannous sulfate and pumice, in a mass ratio of vanadium pentoxide to potassium hydroxide to cesium oxide to ferrous sulfate to manganese sulfate to potassium sulfate to stannous sulfate to pumice = 1: 0.9: 0.3: 2: 0.02: 0.9: 0.1: 20.
The preparation steps of the catalyst are as follows:
(1) Preparation of solution # 1: weighing 1 part of vanadium pentoxide by mass, adding 10 parts of distilled water, then adding 0.9 part of potassium hydroxide and 0.3 part of cesium oxide, heating for dissolving, properly stirring for assisting in dissolving, controlling the dissolving temperature to be 60 +/-2 ℃, filtering after complete dissolving, and obtaining filtrate;
(2) Preparation of No. 2 solution: weighing 2 parts of ferrous sulfate and 0.02 part of manganese sulfate, adding 10 parts of distilled water, heating for dissolving, properly stirring for assisting dissolution, controlling the dissolving temperature to be 60 +/-2 ℃, filtering after complete dissolution, and obtaining filtrate;
(3) Coprecipitation: putting the No. 1 filtered solution into a mixer, slowly adding the No. 2 filtered solution into the No. 1 filtered solution under uniform stirring, wherein a black precipitate exists, standing for half an hour after the addition, filtering, washing a filter cake for three times by using distilled water, and then adding 2.5 parts of 60-70 ℃ distilled water to prepare a thin paste;
(4) Preparation of No. 3 solution: weighing 0.9 part of potassium sulfate and 0.1 part of stannous sulfate, adding 8 parts of distilled water, heating the solution, controlling the dissolving temperature at 60 +/-2 ℃, completely dissolving, and filtering to obtain filtrate;
(5) Preparation of an impregnation liquid: slowly adding the No. 3 solution into the coprecipitation paste liquid prepared in the step (3) under stirring to prepare impregnation liquid after the addition is finished;
(6) Dipping: adding 20 parts of dried pumice stone into a frying pan, adding the impregnation liquid onto the pumice stone, pouring while flanging and heating to uniformly impregnate the pumice stone until no impregnation liquid exists in the pan;
(7) And (3) drying: drying the dipped pumice stone in a drying oven for 10 hours, wherein the drying temperature is controlled at 130-140 ℃;
(8) And (3) activation: the dried catalyst loaded on the pumice is arranged in a fixed bed oxidizer, and is activated for 18 hours by introducing hot air with the temperature of 450-480 ℃ to obtain the catalyst.
The catalyst disclosed by the invention takes vanadium pentoxide as a main catalyst, multiple auxiliary catalysts are compounded, and pumice as a carrier, so that the activity of the catalyst is controlled in a proper state, the high conversion rate of phenanthrene is ensured, the high selectivity of phenanthrenequinone is also ensured, and the yield of phenanthrenequinone is effectively improved.
Detailed Description
The invention is further illustrated by the following examples:
example 1
(1) Preparation of No. 1 solution: weighing 1kg of vanadium pentoxide, adding 10kg of distilled water, then adding 0.9kg of potassium hydroxide and 0.3kg of cesium oxide, heating for dissolving, properly stirring for assisting in dissolving, controlling the dissolving temperature to be 60 +/-2 ℃, filtering after complete dissolving, and obtaining filtrate;
(2) Preparation of No. 2 solution: weighing 2kg of ferrous sulfate and 20g of manganese sulfate, adding 10kg of distilled water, heating for dissolving, properly stirring for assisting dissolution, controlling the dissolving temperature to be 60 +/-2 ℃, filtering after complete dissolution, and obtaining filtrate;
(3) Coprecipitation: putting the No. 1 filtered solution into a mixer, slowly adding the No. 2 filtered solution into the No. 1 filtered solution under uniform stirring, standing for half an hour after the addition of the black precipitate, filtering, washing a filter cake for three times by using distilled water, and then adding 2.5kg of distilled water at 65 ℃ to prepare a thin paste;
(4) Preparation of No. 3 solution: weighing 0.9kg of potassium sulfate and 0.1kg of stannous sulfate, adding 8kg of distilled water, heating the solution, controlling the dissolving temperature to be 60 +/-2 ℃, and filtering after complete dissolution to obtain filtrate;
(5) Preparation of an impregnation liquid: slowly adding the No. 3 solution into the coprecipitation paste liquid prepared in the step (3) under stirring to prepare impregnation liquid after the addition is finished;
(6) Dipping: adding 20kg of dried pumice into a frying pan, adding the impregnation liquid onto the pumice, pouring while flanging and heating to uniformly impregnate the pumice until no impregnation liquid exists in the pan;
(7) And (3) drying: drying the immersed pumice in a drying oven for 10h, wherein the drying temperature is controlled at 130-140 ℃;
(8) Activation: the dried catalyst loaded on the pumice is arranged in a fixed bed oxidizer, and is activated for 18 hours by introducing hot air with the temperature of 450-480 ℃ to obtain the catalyst.
Industrial phenanthrene with content of 95.2% as raw material, and catalyst load of 15g/m 3 And s, controlling the reaction temperature to be 340 +/-2 ℃, introducing 20kg of industrial phenanthrene to obtain 19.1kg of product, testing the product to contain 74.4 mass percent of phenanthrenequinone and the balance of impurities such as biphenyldicarboxylic acid, phthalic anhydride, maleic anhydride and the like, wherein the yield is 74.6 percent based on pure phenanthrene in the raw material.
Example 2
The same catalyst as in example 1 was used, starting from industrial phenanthrene with a content of 95.8% and a catalyst loading of 14g/m 3 And s, controlling the reaction temperature to be 340 +/-2 ℃, and introducing 50kg of industrial phenanthrene to obtain 48.6kg of product, wherein the mass fraction of phenanthrenequinone contained in the product is 75.7% through assay, and the yield is 76.8% based on pure phenanthrene in the raw material.
Example 3
Using the same catalyst as in example 1, starting from a commercial phenanthrene having a content of 96.1%, the catalyst loading was 14g/m 3 And s, controlling the reaction temperature to be 340 +/-2 ℃, and introducing 100kg of industrial phenanthrene to obtain 97.5kg of product, wherein the mass fraction of phenanthrenequinone contained in the product is 75.9% through assay, and the yield is 77% based on pure phenanthrene in the raw materials.
Claims (1)
1. A catalyst for preparing phenanthrene quinone by phenanthrene gas-phase oxidation is characterized by comprising the following preparation steps:
(1) Preparation of No. 1 solution: weighing 1 part of vanadium pentoxide by mass, adding 10 parts of distilled water, then adding 0.9 part of potassium hydroxide and 0.3 part of cesium oxide, heating for dissolving, properly stirring for assisting in dissolving, controlling the dissolving temperature to be 60 +/-2 ℃, filtering after complete dissolving, and obtaining filtrate;
(2) Preparation of No. 2 solution: weighing 2 parts of ferrous sulfate and 0.02 part of manganese sulfate, adding 10 parts of distilled water, heating for dissolving, properly stirring for assisting dissolution, controlling the dissolving temperature to be 60 +/-2 ℃, filtering after complete dissolution, and obtaining filtrate;
(3) Coprecipitation: putting the No. 1 filtered solution into a mixer, slowly adding the No. 2 filtered solution into the No. 1 filtered solution under uniform stirring, wherein a black precipitate exists, standing for half an hour after the addition, filtering, washing a filter cake for three times by using distilled water, and then adding 2.5 parts of 60-70 ℃ distilled water to prepare a thin paste;
(4) Preparation of No. 3 solution: weighing 0.9 part of potassium sulfate and 0.1 part of stannous sulfate, adding 8 parts of distilled water, heating the solution, controlling the dissolving temperature at 60 +/-2 ℃, completely dissolving, and filtering to obtain filtrate;
(5) Preparation of an impregnation liquid: slowly adding the No. 3 solution into the coprecipitation paste liquid prepared in the step (3) under stirring to prepare impregnation liquid after the addition is finished;
(6) Dipping: adding 20 parts of dried pumice stone into a frying pan, adding the impregnation liquid onto the pumice stone, pouring while flanging, heating to uniformly impregnate the pumice stone, and heating until no impregnation liquid exists in the pan;
(7) And (3) drying: drying the immersed pumice in a drying oven for 10h, wherein the drying temperature is controlled at 130-140 ℃;
(8) And (3) activation: the dried catalyst loaded on the pumice is arranged in a fixed bed oxidizer, and the catalyst is prepared after the catalyst is activated for 18 hours by introducing hot air with the temperature of 450-480 ℃;
the catalyst consists of vanadium pentoxide, potassium hydroxide, cesium oxide, ferrous sulfate, manganese sulfate, potassium sulfate, stannous sulfate and pumice in a mass ratio of vanadium pentoxide to potassium hydroxide to cesium oxide to ferrous sulfate to manganese sulfate to potassium sulfate to stannous sulfate to pumice = 1: 0.9: 0.3: 2: 0.02: 0.9: 0.1: 20.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211283500.1A CN115569657B (en) | 2022-10-20 | 2022-10-20 | Catalyst for preparing phenanthrenequinone by gas-phase oxidation of phenanthrene |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211283500.1A CN115569657B (en) | 2022-10-20 | 2022-10-20 | Catalyst for preparing phenanthrenequinone by gas-phase oxidation of phenanthrene |
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| Publication Number | Publication Date |
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| CN115569657A true CN115569657A (en) | 2023-01-06 |
| CN115569657B CN115569657B (en) | 2023-08-29 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008133441A1 (en) * | 2007-04-26 | 2008-11-06 | Mazence Inc. | Novel phenanthrenequinone-based compound and pharmaceutical composition containing the same for the treatment or prevention of disease involving metabolic syndrome |
| CN101927159A (en) * | 2010-07-09 | 2010-12-29 | 广西工业职业技术学院 | Method for preparing oxidation catalyst for phenanthrene |
| CN105272837A (en) * | 2014-07-11 | 2016-01-27 | 鞍钢股份有限公司 | Method for preparing phenanthraquinone |
| CN107663149A (en) * | 2016-07-29 | 2018-02-06 | 浙江工业大学 | A kind of preparation method of phenanthrenequione and its derivative |
| CN109092337A (en) * | 2018-09-09 | 2018-12-28 | 辽宁科技学院 | A kind of catalyst for producing Fluorenone for fluorenes gaseous oxidation |
-
2022
- 2022-10-20 CN CN202211283500.1A patent/CN115569657B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008133441A1 (en) * | 2007-04-26 | 2008-11-06 | Mazence Inc. | Novel phenanthrenequinone-based compound and pharmaceutical composition containing the same for the treatment or prevention of disease involving metabolic syndrome |
| CN101927159A (en) * | 2010-07-09 | 2010-12-29 | 广西工业职业技术学院 | Method for preparing oxidation catalyst for phenanthrene |
| CN105272837A (en) * | 2014-07-11 | 2016-01-27 | 鞍钢股份有限公司 | Method for preparing phenanthraquinone |
| CN107663149A (en) * | 2016-07-29 | 2018-02-06 | 浙江工业大学 | A kind of preparation method of phenanthrenequione and its derivative |
| CN109092337A (en) * | 2018-09-09 | 2018-12-28 | 辽宁科技学院 | A kind of catalyst for producing Fluorenone for fluorenes gaseous oxidation |
Non-Patent Citations (1)
| Title |
|---|
| 张二卯等: "空气催化氧化法制备菲醌的研究进展", 《山西化工》, vol. 29, no. 6, pages 31 - 32 * |
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Application publication date: 20230106 Assignee: Benxi Zhonglian Chemical Plant Assignor: LIAONING INSTITUTE OF SCIENCE AND TECHNOLOGY Contract record no.: X2023210000268 Denomination of invention: Catalysts for gas-phase oxidation of phenanthrene to produce phenanthraquinone Granted publication date: 20230829 License type: Common License Record date: 20231130 |