CN113952948A - Molybdenum oxide catalyst for preparing cyclohexanediol by oxidizing cyclohexene and preparation method and application thereof - Google Patents
Molybdenum oxide catalyst for preparing cyclohexanediol by oxidizing cyclohexene and preparation method and application thereof Download PDFInfo
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- CN113952948A CN113952948A CN202111384553.8A CN202111384553A CN113952948A CN 113952948 A CN113952948 A CN 113952948A CN 202111384553 A CN202111384553 A CN 202111384553A CN 113952948 A CN113952948 A CN 113952948A
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- 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/28—Molybdenum
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/082—Decomposition and pyrolysis
- B01J37/088—Decomposition of a metal salt
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
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- C—CHEMISTRY; METALLURGY
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
The invention relates to a heterogeneous catalyst, in particular to molybdenum oxide (MoO) for preparing cyclohexanediol by oxidizing cyclohexene3) The preparation method of the catalyst comprises the steps of calcining ammonium molybdate tetrahydrate in air, nitrogen or hydrogen atmosphere, and preserving heat for 1-4 hours at the calcining temperature of 350-550 ℃ to obtain MoO3A catalyst. MoO prepared by using cyclohexene as substrate, acetonitrile as reaction solvent and hydrogen peroxide solution as oxidant3Cyclohexene is oxidized under the action of a catalyst to prepare cyclohexanediol. The reaction has high conversion rate and selectivity, short reaction time, easy temperature control, and post-reaction treatmentSimple, safe and pollution-free, and is beneficial to large-scale production and application.
Description
Technical Field
The invention relates to a heterogeneous catalyst, in particular to a reaction catalyst for preparing cyclohexanediol by catalytic oxidation of cyclohexene, and a preparation method and application thereof.
Background
The selective oxidation of olefin is an important method for synthesizing fine chemical intermediates, and is a very important chemical reaction process with wide application in the fields of petrochemical industry and fine chemical industry. Taking cyclohexene as an example, the selective oxidation is one of the most important and studied oxidation reactions in the chemical industry, mainly because the unsaturated C ═ C bond and a plurality of active α -H bonds exist in cyclohexene molecule, and the reaction can occur under the same oxidation conditions to generate a plurality of oxidation products, for example, oxidation of C ═ C double bond can generate cyclohexene oxide, oxidation of allyl (α -H) can generate cyclohexenone and cyclohexenol, etc., as shown in fig. 1. They are very important chemical intermediates, and can react with various functional groups such as amine, carboxylic acid, alcohol and the like to generate fine chemicals with high added value. However, the target product selectivity is poor and the yield is not ideal due to more reaction paths and complex process in the cyclohexene oxidation process. Therefore, designing and preparing an oxidation catalyst with high activity and high selectivity to realize the efficient selective catalytic oxidation of cyclohexene to generate a single target product with a high added value is an important research topic.
Taking 1, 2-cyclohexanediol as an example, the compound is one of products of cyclohexene oxidation, is also a very important organic synthesis raw material, and can be used for preparing various organic intermediates. The epoxy resin diluent is mainly used in the industries of medicines, pesticides, rubber auxiliaries, plasticizers, liquid crystal materials and the like, and is also a raw material of an epoxy resin high-grade diluent. With the rapid development of petrochemical industry, the method can also be used for preparing catechol by dehydrogenation, and has wide application.
Disclosure of Invention
The invention aims to provide high-activity and high-selectivity MoO for preparing cyclohexanediol by oxidizing cyclohexene3A catalyst, a preparation method and application thereof. Preparation of MoO in the invention3The catalyst adopts a simple high-temperature calcination method, and does not need to be added in the reaction for preparing the 1, 2-cyclohexanediol by oxidizing the cyclohexeneAnd (3) an additive.
The technical scheme adopted by the invention is as follows: MoO for preparing cyclohexanediol by oxidizing cyclohexene3The preparation method of the catalyst comprises the following steps: calcining ammonium molybdate tetrahydrate in air, nitrogen or hydrogen atmosphere, and preserving heat for 1-4 hours at the calcining temperature of 350-550 ℃ to obtain MoO3A catalyst.
Preferably, the calcination procedure is to heat the mixture from room temperature to 100 ℃ at a heating rate of 5 ℃/min, then heat the mixture from 100 ℃ to 350-550 ℃ at 3 ℃/min, and then keep the temperature for 1-4 hours.
Preferably, the holding temperature is 450 ℃ and the holding time is 2 h.
Preferably, the calcination atmosphere is air.
The catalyst prepared by the method is used for preparing cyclohexanediol by epoxidation of cyclohexene, and comprises the following steps: MoO prepared by using cyclohexene as substrate, acetonitrile as reaction solvent and hydrogen peroxide solution as oxidant through the method3Cyclohexene is oxidized under the action of a catalyst to prepare cyclohexanediol.
Compared with the prior art, the application has the following beneficial effects: the invention aims to prepare MoO by the simplest and most efficient high-temperature calcination method3The catalyst finished product is used for catalyzing and oxidizing cyclohexene to synthesize trans-1, 2-cyclohexanediol, the reaction has high conversion rate and selectivity, the time in the reaction process is short, the temperature is easy to control, the post-reaction treatment is simple, safe and pollution-free, and the large-scale production and application are facilitated.
Drawings
FIG. 1 shows the oxidation products that may be formed by catalytic oxidation of cyclohexene.
FIG. 2 shows MoO obtained in example 33XRD diffractogram of the catalyst.
Detailed Description
The present invention is not limited to the following embodiments, and those skilled in the art can implement the present invention in other embodiments according to the disclosure of the present invention, or make simple changes or modifications on the design structure and idea of the present invention, and fall into the protection scope of the present invention. It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The invention is described in more detail below with reference to the following examples:
in the context of the present specification, including the following examples and comparative examples, the evaluation of catalytic reaction performance was carried out by analyzing each composition in the reaction system by gas chromatography and quantifying by peak area normalization, and the evaluation indexes such as conversion of the reactant and selectivity of the product were calculated based on the analysis results by the conventional techniques.
In the invention, the calculation formula of the conversion rate of cyclohexene is as follows:
calculation formula of cyclohexene conversion:
the selectivity of 1, 2-cyclohexanediol is calculated as follows:
is the conversion of cyclohexene, SiAs a selectivity to the product 1, 2-cyclohexanediol, n0Is the initial molar amount (mol), n, of cyclohexene charged1Is the molar amount (mol) of unreacted cyclohexene, niIs the molar weight (mol) of the product 1, 2-cyclohexanediol.
Examples 1-6 MoO3Screening of preparation calcination time
Example 1
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 450 ℃ at the temperature of 3 ℃/min, and the calcining temperature is kept for 1h at the temperature of 450 ℃. To obtain MoO3Catalyst, recorded as MoO3-1。
Example 2
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 450 ℃ at the temperature of 3 ℃/min, and the calcining temperature is kept for 1.5h at the temperature of 450 ℃. To obtain MoO3Catalyst, recorded as MoO3-2。
Example 3
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 450 ℃ at the temperature of 3 ℃/min, and the calcining temperature is kept for 2h at the temperature of 450 ℃. To obtain MoO3Catalyst, recorded as MoO3-3。
Example 4
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 450 ℃ at the temperature of 3 ℃/min, and the calcining temperature is kept for 2.5h at the temperature of 450 ℃. To obtain MoO3Catalyst, recorded as MoO3-4。
Example 5
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 450 ℃ at the temperature of 3 ℃/min, and the calcining temperature is kept for 3h at the temperature of 450 ℃. To obtain MoO3Catalyst, recorded as MoO3-5。
Example 6
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is raised from room temperature to 100 ℃ at a heating rate of 5 ℃/min, then the calcination temperature is raised from 100 ℃ to 450 ℃ at 3 ℃/min, and the calcination temperature is kept at 450 ℃ for 4 h. To obtain MoO3Catalyst, recorded as MoO3-6。
Examples 7-8 MoO3Screening for preparing a roasting atmosphere
Example 7
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2And placing the O in a porcelain boat, and calcining the O in a muffle furnace in a nitrogen atmosphere, wherein the muffle furnace calcining procedure is to raise the temperature from room temperature to 100 ℃ at a heating rate of 5 ℃/min, then raise the calcining temperature from 100 ℃ to 450 ℃ at 3 ℃/min, and keep the calcining temperature at 450 ℃ for 2 h. To obtain MoO3Catalyst, recorded as MoO3-7。
Example 8
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in a muffle furnace in a hydrogen atmosphere, wherein the muffle furnace calcining procedure is as follows: the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 450 ℃ at the temperature of 3 ℃/min, and the calcining temperature is kept for 2h at the temperature of 450 ℃. To obtain MoO3Catalyst, recorded as MoO3-8。
Examples 9-12 MoO3Screening of preparation calcination temperature
Example 9
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 350 ℃ at the temperature of 3 ℃/min, and the calcining temperature is kept for 2h at the temperature of 350 ℃. To obtain MoO3Catalyst, recorded as MoO3-9。
Example 10
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is raised from room temperature to 100 ℃ at a heating rate of 5 ℃/min, then the calcination temperature is raised from 100 ℃ to 400 ℃ at 3 ℃/min, and the calcination temperature is kept at 400 ℃ for 2 h. To obtain MoO3Catalyst, recorded as MoO3-10。
Example 11
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is raised from room temperature to 100 ℃ at a heating rate of 5 ℃/min, then the calcination temperature is raised from 100 ℃ to 500 ℃ at 3 ℃/min, and the calcination temperature is kept at 500 ℃ for 2 h. To obtain MoO3Catalyst, recorded as MoO3-11。
Example 12
3.0g (NH) are weighed on a weighing balance4)6Mo7O24·4H2Placing O in a porcelain boat, and calcining in an air atmosphere by using a muffle furnace, wherein the muffle furnace calcining procedure is as follows: the temperature is raised from room temperature to 100 ℃ at a heating rate of 5 ℃/min, then the calcination temperature is raised from 100 ℃ to 550 ℃ at 3 ℃/min, and the calcination temperature is kept at 550 ℃ for 2 h. To obtain MoO3Catalyst, recorded as MoO3-12。
Example 13
1.0mL of acetonitrile solvent, 0.1mL of cyclohexene reactant, and 0.1mL of hydrogen peroxide solution were sequentially added to a reaction tube having a volume of 10mL, and finally 0.1g of the catalyst used in examples 1 to 6 was added thereto, and after sealing, the reaction temperature was set to 60 ℃ and the reaction time was set to 2 hours while stirring. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
The results of the catalytic performances are summarized in Table 1, from which it can be seen that the catalyst MoO3And the calcination time of-3 is 2h, so that the catalytic activity and the epoxide yield are higher.
Table 1: examples 1-6 catalyst preparation-calcination time vs. catalyst Performance test results
Example 14
1.0mL of acetonitrile solvent, 0.1mL of cyclohexene reactant, and 0.1mL of hydrogen peroxide solution were sequentially added to a reaction tube having a volume of 10mL, and finally 0.1g of the catalyst used in examples 7 and 8 was added thereto, and after sealing, the reaction temperature was set to 60 ℃ and the reaction time was set to 2 hours while stirring. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
The results of the catalytic performances are summarized in Table 2, from which it can be seen that the catalyst MoO3And 3, the catalyst has higher catalytic activity and epoxide yield under the air atmosphere.
Table 2: examples 3, 7, 8 catalyst preparation-calcination atmosphere vs. Performance test results
Example 15
1.0mL of acetonitrile solvent, 0.1mL of cyclohexene reactant, and 0.1mL of hydrogen peroxide solution were sequentially added to a reaction tube having a volume of 10mL, and finally 0.1g of the catalyst used in examples 9 to 12 was added thereto, and after sealing, the reaction temperature was set to 60 ℃ and the reaction time was set to 2 hours while stirring. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
The results of the catalytic performances are summarized in Table 3, from which it can be seen that the catalyst MoO3-3 calcination at 450 ℃ has higher catalytic activity and epoxide yield.
Table 3: examples 3, 9-12 catalyst preparation-calcination temperature vs. Performance test results
EXAMPLES 16-20 screening of reaction solvents
Example 16
1.0mL of methanol solvent, 0.1mL of reactant cyclohexene, and 0.1mL of hydrogen peroxide solution were sequentially added to a reaction tube having a volume of 10mL, and finally MoO was added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 17
In a reaction tube with a volume of 10mL, 1.0mL of ethanol solvent, 0.1mL of reactant cyclohexene and 0.1mL of hydrogen peroxide solution are sequentially added, and finally MoO is added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 18
1.0mL of dimethyl sulfoxide solvent, 0.1mL of reactant cyclohexene and 0.1mL of hydrogen peroxide solution are sequentially added into a reaction tube with the volume of 10mL, and finally MoO is added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 19
1.0mL of 1, 2-dichloroethane solvent, 0.1mL of cyclohexene reactant, and 0.1mL of hydrogen peroxide solution were sequentially added to a reaction tube having a volume of 10mL, and finally MoO was added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 20
In a reaction tube with a volume of 10mL, 1.0mL of acetonitrile solvent, 0.1mL of reactant cyclohexene, and 0.1mL of hydrogen peroxide solution were sequentially added, and finally MoO was added3-3 catalyst 0.1g, after sealing, setting the reaction temperature to be 60 ℃ and the reaction time to be 2h under the stirring state. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
The results of the catalytic performances of examples 16 to 20 are summarized in Table 4, from which it is clear that the catalyst MoO3-3 has higher catalytic activity and epoxide yield in acetonitrile solvent.
Table 4: examples 16-20 test results of reaction solvent vs. catalyst Performance
EXAMPLES 21-26 screening of oxidizing Agents
Example 21
In a reaction tube with a volume of 10mL, 1.0mL of acetonitrile solvent, 0.1mL of reactant cyclohexene, and 0.1mL of hydrogen peroxide solution were sequentially added, and finally MoO was added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 22
In a reaction tube with a volume of 10mL, 1.0mL of acetonitrile solvent, 0.1mL of reactant cyclohexene, and 0.1mL of di-tert-butyl peroxide are sequentially added, and finally MoO is added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 23
In a reaction tube with a volume of 10mL, 1.0mL of acetonitrile solvent, 0.1mL of reactant cyclohexene, and 0.1mL of tert-butyl peroxide were sequentially added, and finally MoO was added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 24
In a reaction tube with a volume of 10mL, 1.0mL of acetonitrile solvent, 0.1mL of reactant cyclohexene, and 0.1mL of benzoyl peroxide are sequentially added, and finally MoO is added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 25
In a reaction tube with a volume of 10mL, 1.0mL of acetonitrile solvent, 0.1mL of reactant cyclohexene, and 0.1mL of dicumyl peroxide are sequentially added, and finally MoO is added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
Example 26
In a reaction tube with a volume of 10mL, 1.0mL of acetonitrile solvent, 0.1mL of reactant cyclohexene, and 0.1mL of m-chloroperoxybenzoic acid were sequentially added, and finally MoO was added3-3 catalyst 0.1g, sealing, and stirring at 60 deg.C for 2 h. After the reaction was completed, the conversion, selectivity and yield were analyzed by gas chromatography.
The results of the catalytic performances of examples 21 to 26 are summarized in Table 5, from which it is clear that the catalyst MoO3-3 has higher catalytic activity and epoxide yield in the case of using hydrogen peroxide as an oxide.
Table 5: examples 21-26 results of oxidant to catalyst Performance testing
In addition to the catalytic results of several other common transition metal oxides: as shown in Table 6, the catalytic performance was lower than that of the MoO of the present application3Catalyst (in MoO)3-3 as an example), and the selectivity of cyclohexanediols is much lower than that of MoO3A catalyst.
TABLE 6 catalytic Properties of several common transition metal oxides
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and their concepts should be equivalent or changed within the technical scope of the present invention.
Claims (5)
1. Molybdenum oxide (MoO) for preparing cyclohexanediol by oxidizing cyclohexene3) The preparation method of the catalyst is characterized by comprising the following steps: the method comprises the following steps: calcining ammonium molybdate tetrahydrate in air, nitrogen or hydrogen atmosphere, and preserving heat for 1-4 hours at the calcining temperature of 350-550 ℃ to obtain MoO3A catalyst.
2. MoO for cyclohexene oxidation preparation of cyclohexanediols according to claim 13The preparation method of the catalyst is characterized by comprising the following steps: the calcining procedure is that the temperature is increased from room temperature to 100 ℃ at the temperature increasing rate of 5 ℃/min, then the calcining temperature is increased from 100 ℃ to 350-550 ℃ at the speed of 3 ℃/min, and the temperature is kept for 1-4 hours at the temperature.
3. MoO for cyclohexene oxidation preparation of cyclohexanediols according to claim 13The preparation method of the catalyst is characterized by comprising the following steps: the heat preservation temperature is 450 ℃, and the heat preservation time is 2 hours.
4. MoO for cyclohexene oxidation preparation of cyclohexanediols according to claim 13The preparation method of the catalyst is characterized by comprising the following steps: the calcination atmosphere was air.
5. MoO for cyclohexene oxidation to cyclohexanediol according to any of claims 1 to 43The catalyst prepared by the preparation method of the catalyst is used for preparing cyclohexanediol by oxidizing cyclohexene, and is characterized in that: the method comprises the following steps: MoO prepared by using cyclohexene as substrate, acetonitrile as reaction solvent and hydrogen peroxide solution as oxidant through the method3Cyclohexene is oxidized under the action of a catalyst to prepare cyclohexanediol.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101279892A (en) * | 2007-04-03 | 2008-10-08 | 微宏科技（湖州）有限公司 | Method for preparing 1,2-cyclohexanediol by catalytic oxidation of cyclohexene |
| CN102850205A (en) * | 2011-06-30 | 2013-01-02 | 中国石油化工股份有限公司 | Method for producing 1,2-cyclohexanediol and adipic acid |
| WO2016078673A1 (en) * | 2014-11-20 | 2016-05-26 | Danmarks Tekniske Universitet | Process for reducing the oxygen content of biomass using molybdenum-based catalysts |
| CN106315741A (en) * | 2016-10-17 | 2017-01-11 | 青岛科技大学 | Method for removing methylene blue from dye wastewater |
-
2021
- 2021-11-19 CN CN202111384553.8A patent/CN113952948A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101279892A (en) * | 2007-04-03 | 2008-10-08 | 微宏科技（湖州）有限公司 | Method for preparing 1,2-cyclohexanediol by catalytic oxidation of cyclohexene |
| CN102850205A (en) * | 2011-06-30 | 2013-01-02 | 中国石油化工股份有限公司 | Method for producing 1,2-cyclohexanediol and adipic acid |
| WO2016078673A1 (en) * | 2014-11-20 | 2016-05-26 | Danmarks Tekniske Universitet | Process for reducing the oxygen content of biomass using molybdenum-based catalysts |
| CN106315741A (en) * | 2016-10-17 | 2017-01-11 | 青岛科技大学 | Method for removing methylene blue from dye wastewater |
Non-Patent Citations (1)
| Title |
|---|
| QI NENG ZHANG ET AL.: "The oxidation of olefins by t-butyl hydrogen peroxide to prepare 1, 2-diols over metal oxide catalysts", 《CATALYSIS COMMUNICATIONS》, vol. 10, pages 1279 - 1280 * |
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