CN113813993B - High selectivity Ag 2 C 2 O 4 /Ag 2 Preparation of O composite catalyst and application thereof in ethylbenzene oxidation - Google Patents
High selectivity Ag 2 C 2 O 4 /Ag 2 Preparation of O composite catalyst and application thereof in ethylbenzene oxidation Download PDFInfo
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- CN113813993B CN113813993B CN202111186139.6A CN202111186139A CN113813993B CN 113813993 B CN113813993 B CN 113813993B CN 202111186139 A CN202111186139 A CN 202111186139A CN 113813993 B CN113813993 B CN 113813993B
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
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Abstract
The application discloses a high-selectivity Ag 2 C 2 O 4 /Ag 2 The preparation method of the O composite catalyst and the application thereof in ethylbenzene oxidation comprises the following steps: s1: dissolving silver salt in deionized water to form a solution A; s2: oxalic acid is dissolved in deionized water to form solution B; s3: at room temperature, slowly adding the solution B in the S2 into the solution A under stirring to react, and continuously generating white precipitate in the reaction process. After the reaction is finished, keeping the mixture in a stirring state, standing and ageing the mixture for 4 hours, and obtaining Ag after suction filtration, washing and drying 2 C 2 O 4 A material; s4: ag obtained in S3 2 C 2 O 4 Calcining in a tubular reaction furnace at 120-180 ℃ to obtain Ag 2 C 2 O 4 /Ag 2 O composite catalyst. The catalyst of the application has the advantages of high acetophenone selectivity, recycling and the like in the preparation of acetophenone.
Description
Technical Field
The application relates to the technical field of acetophenone preparation, in particular to high-selectivity Ag 2 C 2 O 4 /Ag 2 Preparation of O composite catalyst and application in ethylbenzene oxidation.
Background
Acetophenone is an important intermediate in organic synthesis. Generally, air and oxygen are commonly used in industry as oxidants, and acetophenone is produced by high-temperature catalytic oxidation of ethylbenzene. The catalyst used in the method is mostly cobalt-based catalyst such as cobalt acetate, cobalt nitrate, etc. However, cobalt-based catalysts are not efficient in catalysis, especially with low product selectivity (typically with alpha-phenylethanol by-product, resulting in acetophenone selectivity below 85%). Moreover, the cobalt-based catalyst cannot be recycled, resulting in increased industrial cost.
Considering silver-based catalysts (such as elemental silver, silver nitrate, silver oxide, silver oxalate, silver phosphate, silver sulfate, silver carbonate and the like) and complexes thereof, the generation of peroxy radicals can be accelerated in the ethylbenzene catalytic oxidation process, and the high-efficiency conversion of ethylbenzene is realized; in addition, the silver-based catalyst and the compound thereof have better reaction capacity and electron transfer capacity under the action of heat, can effectively realize the side chain reaction of benzene rings and improve the selectivity of acetophenone. Thus, the present application provides an Ag 2 C 2 O 4 /Ag 2 The preparation method of the O composite catalyst and the O composite catalyst are applied to a system for preparing acetophenone by ethylbenzene catalytic oxidation. Ag according to the present application 2 C 2 O 4 /Ag 2 The O composite catalyst has the characteristics of high selectivity and recyclability, and has a wide industrial application prospect.
Disclosure of Invention
The application provides Ag with high selectivity 2 C 2 O 4 /Ag 2 The O composite catalyst has the advantages of high acetophenone selectivity, recycling and the like in the preparation of acetophenone.
The application provides high-selectivity Ag 2 C 2 O 4 /Ag 2 The preparation method of the O composite catalyst comprises the following steps:
s1: dissolving silver salt in deionized water to form a solution A;
s2: oxalic acid is dissolved in deionized water to form solution B;
s3: and (3) adding the solution B in the step (S2) into the solution A under stirring at room temperature, reacting, and standing and aging the mixture for 3-5h while keeping the stirring state after the reaction is finished. Then filtering, washing and drying to obtain Ag 2 C 2 O 4 ；
S4: ag in S3 2 C 2 O 4 Calcining the material in a tubular reaction furnace to obtain Ag 2 C 2 O 4 /Ag 2 O composite catalyst.
Preferably, the silver salt is silver nitrate, and the concentration of the solution A is 1-4mol/L.
Preferably, the molar concentration of the oxalic acid in the solution B is 0.5-2mol/L.
Preferably, the reaction time in S3 is 25-35min.
Preferably, the calcination condition in the step S4 is pyrolysis reaction under air atmosphere, and the heating rate is 2-5 ℃/min. The pyrolysis temperature is 120-180 ℃, and the heat preservation time is 1.8-2.2h. Cooling for 1.5-2.5h to room temperature after the reaction is finished to obtain Ag 2 C 2 O 4 /Ag 2 O composite catalyst.
The high-selectivity Ag prepared by the method provided by the application 2 C 2 O 4 /Ag 2 O composite catalyst.
The application provides the high-selectivity Ag 2 C 2 O 4 /Ag 2 The application of the O composite catalyst in preparing acetophenone by ethylbenzene oxidation.
Preferably, the method for preparing acetophenone by ethylbenzene oxidation catalyzed by the composite catalyst comprises the following steps: ethylbenzene and Ag 2 C 2 O 4 /Ag 2 Adding the O composite catalyst into a reactor for reaction, filtering the mixture at normal temperature and normal pressure after the reaction is finished, performing alkali washing and liquid separation on the filtrate, and distilling the upper liquid to obtain acetophenone.
Preferably, the Ag 2 C 2 O 4 /Ag 2 The dosage of the O composite catalyst is 2-3% of the molar quantity of ethylbenzene.
Preferably, the conditions of the reaction are: stirring speed is 250rpm, air is used as an oxygen source, gas flow rate is kept at 100mL/min, reaction temperature is 120 ℃, and reaction time is 24 hours.
Mechanism of action
Generally speaking, ag 2 Catalytic performance of O compared with Ag 2 C 2 O 4 Poor and therefore directly bind Ag 2 C 2 O 4 With Ag 2 The use of O in combination results in a decrease in the catalytic performance of the catalyst. However, for the present application, the catalytic performance of the prepared composite catalyst in preparing acetophenone by ethylbenzene oxidation is rather improved to some extent, because of the Ag prepared in the present application 2 C 2 O 4 /Ag 2 The O composite catalyst plays a key role in promoting the generation of free radicals. The peroxy radical formed on the surface of the catalyst can abstract hydrogen in the substrate to accelerate the reaction process of the radical, so that the reaction can be promoted. Ag (silver) 2 C 2 O 4 /Ag 2 The mechanism of the enhancement of the catalytic efficiency of the O composite material is as follows: (1) Under heating condition, ag 2 The electrons in O are excited and transferred to Ag 2 C 2 O 4 Surface, composite catalyst activates O adsorbed on the surface 2 And accelerates the formation of active oxygen. Next, ag 2 C 2 O 4 Electrons on the surface are captured by active oxygen to form peroxy radicals; when the peroxide radical contacts ethylbenzene, hydrogen in the ethylbenzene is abstracted, corresponding hydroperoxide and ethylbenzene radical products are generated, and oxidation reaction can be effectively carried out. (2) Ag (silver) 2 C 2 O 4 /Ag 2 The O catalyst effectively reduces the reaction energy barrier, so that the ethylbenzene can be converted efficiently under mild conditions. (3) Ag (silver) 2 C 2 O 4 Ag formed after calcination 2 C 2 O 4 /Ag 2 The O composite catalyst has enhanced porosity, so that the selectivity of acetophenone is improved.
The beneficial technical effects of the application
(1) In the application, the prepared Ag 2 C 2 O 4 Calcining the material at high temperature, and controlling pyrolysis temperature and time to enable part of Ag 2 C 2 O 4 Decompose to form Ag 2 C 2 O 4 /Ag 2 O composite catalyst. The method improves Ag 2 C 2 O 4 The catalyst is unstable at high temperature, and the specific surface area of the calcined material is increased, which is beneficial to the contact reaction between the substrate and the catalyst. The catalyst has the characteristics of high activity, high selectivity and high stability, and has good industrial application prospect.
(2) Ag used in the present application 2 C 2 O 4 /Ag 2 The O composite catalyst has good stability and difficult deactivation in the ethylbenzene catalytic oxidation reaction process, thus realizing the recycling of the catalyst and Ag 2 C 2 O 4 /Ag 2 The retention rate of the acetophenone yield after the O composite catalyst is circulated for 5 times is over 96 percent.
Drawings
FIG. 1 shows Ag according to this application 2 C 2 O 4 TG plot under air atmosphere;
FIG. 2 shows the Ag obtained by calcining at different temperatures according to this application 2 C 2 O 4 /Ag 2 XRD pattern of O composite catalyst;
a-e in fig. 3 are the gas chromatograms of examples 1-3 and comparative examples 1-2, respectively.
Detailed Description
The detection method of ethylbenzene conversion and acetophenone selectivity in the application adopts gas chromatography quantitative analysis (Agilent 6890N gas chromatograph). The chromatographic conditions were: the temperature of the gasification chamber is 280 ℃; FID detection, wherein the detector temperature is 260 ℃; the column temperature was raised by programming to an initial temperature of 80℃and at a rate of 25℃per minute to 130 ℃. And quantitatively analyzing characteristic peaks of ethylbenzene and acetophenone according to the detection result, and calculating to obtain the ethylbenzene conversion rate and the acetophenone selectivity. Silver nitrate, oxalic acid and the like are all commercially available in the present application.
Example 1
The preparation method of the high-selectivity silver composite catalyst and the application thereof in ethylbenzene oxidation, which are provided by the application, comprises the following steps:
s1: dissolving silver nitrate into deionized water to form a solution A, wherein the concentration of the solution A is 2mol/L;
s2: oxalic acid is dissolved in deionized water to form a solution B, and the concentration of an oxalic acid aqueous solution is 1mol/L;
s3: solution B in S2 was slowly added to solution A at room temperature with stirring, at which time precipitation continued. After the reaction, keeping the mixture in a stirring state, and standing and aging the mixture for 4 hours. Then carrying out suction filtration and washing, and finally drying in a constant-temperature blast drying oven at 90 ℃ to obtain Ag 2 C 2 O 4 A material;
s4: and (3) carrying out pyrolysis reaction on the material in the step (S3) in the air atmosphere of the tubular reaction furnace, wherein the heating rate is 3 ℃/min. The pyrolysis temperature is 160 ℃, the heat preservation time is 2.0h, and Ag is obtained after calcination 2 C 2 O 4 /Ag 2 O composite catalyst.
The method for applying the high-selectivity silver composite catalyst to preparing acetophenone by ethylbenzene oxidation comprises the following steps: 100mL of ethylbenzene and 2.4% Ag by mole of ethylbenzene were used 2 C 2 O 4 /Ag 2 And adding the O composite catalyst into a reactor for reaction. The reaction conditions are as follows: the stirring speed is 250rpm, air is used as an oxygen source, the gas flow rate is kept at 100mL/min, the reaction temperature is 120 ℃, and the reaction time is 24 hours. Filtering the mixture at normal temperature and normal pressure after the reaction is finished, performing alkali washing and liquid separation on the filtrate, taking upper liquid for distillation, collecting ethylbenzene fraction at about 140 ℃, and collecting acetophenone fraction at about 202 ℃. The product is analyzed and detected by gas chromatography, and the result shows that the ethylbenzene conversion rate is 56.7%, the acetophenone selectivity is 96.5%, and the acetophenone yield retention rate reaches 96.2% after 5 times of circulation.
Example 2
The preparation method of the high-selectivity silver composite catalyst and the application thereof in ethylbenzene oxidation, which are provided by the application, comprises the following steps:
the preparation method of the high-selectivity silver composite catalyst and the application thereof in ethylbenzene oxidation, which are provided by the application, comprises the following steps:
s1: dissolving silver nitrate into deionized water to form solution A, wherein the concentration of the silver nitrate is 4mol/L;
s2: oxalic acid is dissolved in deionized water under the condition of slight heat to form solution B, and the concentration of an oxalic acid aqueous solution is 2mol/L;
s3: solution B in S2 was slowly added to solution A with stirring, at which time precipitation continued to occur. After the reaction, keeping the mixture in a stirring state, and standing and aging the mixture for 4 hours. Then carrying out suction filtration and washing, and finally drying in a constant-temperature blast drying oven at 90 ℃ to obtain Ag 2 C 2 O 4 A material;
s4: and (3) carrying out pyrolysis reaction on the material in the step (S3) in the air atmosphere of the tubular reaction furnace, wherein the heating rate is 2 ℃/min. The pyrolysis temperature is 180 ℃, the heat preservation time is 2.0h, and Ag is obtained after calcination 2 C 2 O 4 /Ag 2 O composite catalyst.
The method for applying the high-selectivity silver composite catalyst to preparing acetophenone by ethylbenzene oxidation comprises the following steps: 100mL of ethylbenzene and 2.4% Ag by mole of ethylbenzene were used 2 C 2 O 4 /Ag 2 The O composite catalyst is added into a reactor for reaction, and the reaction conditions are as follows: stirring at 250rpm, taking air as an oxygen source, maintaining the gas flow rate at 100mL/min at the reaction temperature of 120 ℃ for 24 hours, filtering the mixture at normal temperature and normal pressure after the reaction is finished, performing alkali washing and liquid separation on the filtrate, taking the upper liquid for distillation, collecting ethylbenzene fraction at about 140 ℃, and collecting acetophenone fraction at about 202 ℃. The product is analyzed and detected by gas chromatography, and the result shows that the ethylbenzene conversion rate is 61.8%, the acetophenone selectivity is 97.2%, and the acetophenone yield retention rate reaches 97.5% after 5 times of circulation.
Example 3
The application provides high-selectivity Ag 2 C 2 O 4 /Ag 2 The preparation method of the O composite catalyst and the application thereof in ethylbenzene oxidation comprises the following steps:
the application provides high-selectivity Ag 2 C 2 O 4 /Ag 2 The preparation method of the O composite catalyst and the application thereof in ethylbenzene oxidation comprises the following steps:
s1: dissolving silver nitrate into deionized water to form a solution A, wherein the concentration of the silver nitrate is 3mol/L;
s2: oxalic acid is dissolved in deionized water to form solution B, and the concentration of an oxalic acid aqueous solution is 1.5mol/L;
s3: solution B in S2 was slowly added to solution A at room temperature with stirring, at which time precipitation continued. After the reaction, keeping the mixture in a stirring state, and standing and aging the mixture for 4 hours. Then carrying out suction filtration and washing, and finally drying in a constant-temperature blast drying oven at 90 ℃ to obtain Ag 2 C 2 O 4 A material;
s4: and (3) carrying out pyrolysis reaction on the material in the step (S3) in the air atmosphere of the tubular reaction furnace, wherein the heating rate is 5 ℃/min. The pyrolysis temperature is 140 ℃, the heat preservation time is 2.0h, and Ag is obtained after calcination 2 C 2 O 4 /Ag 2 And (3) an O catalyst.
The method for applying the high-selectivity silver composite catalyst to preparing acetophenone by ethylbenzene oxidation comprises the following steps: 100mL of ethylbenzene and 2.4% Ag by mole of ethylbenzene were used 2 C 2 O 4 /Ag 2 The O composite catalyst is added into a reactor for reaction, and the reaction conditions are as follows: stirring at 250rpm, taking air as an oxygen source, maintaining the gas flow rate at 100mL/min at the reaction temperature of 120 ℃ for 24 hours, filtering the mixture at normal temperature and normal pressure after the reaction is finished, performing alkali washing and liquid separation on the filtrate, taking the upper liquid for distillation, collecting ethylbenzene fraction at about 140 ℃, and collecting acetophenone fraction at about 202 ℃. The product is analyzed and detected by gas chromatography, and the result shows that the ethylbenzene conversion rate is 48.7%, the acetophenone selectivity is 94.5%, and the acetophenone yield retention rate reaches 94.6% after 5 times of circulation.
Comparative example 1
Ag is obtained in the step S3 2 C 2 O 4 The material was directly used in ethylbenzene oxidation reaction under the same conditions as in example 3, and the result showed that the ethylbenzene conversion was 43.6% and the acetophenone selectivity was 92.4%.
Comparative example 2
Ag is obtained in the step S3 2 C 2 O 4 Calcining the material at 170 ℃ for 6 hours to obtain Ag 2 O material, which is subsequently used in ethylbenzene oxidationThe other conditions were the same as in example 3, and the result showed that the ethylbenzene conversion was 22.5% and the acetophenone selectivity was 80.2%.
FIG. 1 is Ag 2 C 2 O 4 As can be seen from the graph, ag shows a thermal decomposition curve under an air atmosphere 2 C 2 O 4 The thermal decomposition in the air only has one weight loss process, the weight loss temperature range is 164.8-238.2 ℃, and the weight loss rate is 28.8%. The whole weightlessness process is more severe, and corresponds to Ag 2 C 2 O 4 Decomposing to form Ag 2 O。
FIG. 2 shows Ag produced at different pyrolysis temperatures 2 C 2 O 4 /Ag 2 XRD pattern of O composite. As can be seen from the graph, when the pyrolysis temperature is lower (less than or equal to 120 ℃), the diffraction peaks are stronger at the positions of 17.27 DEG, 29.81 DEG, 32.46 DEG, 51.68 DEG and the like of 2 theta, and are basically consistent with the standard PDF- #22-1335 of silver oxalate (marked by # in the graph); along with the increase of the pyrolysis temperature, the original Ag is removed 2 C 2 O 4 In addition to diffraction peaks, the sample shows new strong diffraction peaks at 38.68 degrees, 50.43 degrees, 60.50 degrees, 66.83 degrees and the like of 2 theta, and the sample is matched with Ag 2 The standard PDF- #19-1155 for O was substantially identical (identified in the figure), demonstrating that Ag was obtained by pyrolysis 2 C 2 O 4 /Ag 2 O composite material.
FIG. 3 shows gas chromatograms of examples 1-3 and comparative examples 1-2, wherein the peak order of each substance in the chromatograms is ethylbenzene, acetophenone and phenethyl alcohol in sequence, and the separation degree of each peak is good.
The foregoing description of the preferred embodiments of the application is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the application.
Claims (8)
1. High selectivity Ag 2 C 2 O 4 /Ag 2 The application of the O composite catalyst in preparing acetophenone by ethylbenzene oxidation is characterized in that the preparation method of the composite catalyst comprises the following steps:
s1: dissolving silver salt in deionized water to form a solution A;
s2: oxalic acid is dissolved in deionized water to form solution B;
s3: at room temperature, adding the solution B in the S2 into the solution A under stirring to react, keeping the mixture under stirring for aging for 3-5h after the reaction is finished, and obtaining Ag after suction filtration, washing and drying 2 C 2 O 4 ；
S4: ag in S3 2 C 2 O 4 Calcining the material in a tubular reaction furnace to obtain Ag 2 C 2 O 4 /Ag 2 O composite catalyst.
2. The high selectivity Ag of claim 1 2 C 2 O 4 /Ag 2 The application of the O composite catalyst in preparing acetophenone by ethylbenzene oxidation is characterized in that silver salt is silver nitrate, and the concentration of solution A is 1-4mol/L.
3. The use of the high selectivity Ag2C2O4/Ag2O composite catalyst according to claim 1 for the preparation of acetophenone by ethylbenzene oxidation, wherein the molar concentration of oxalic acid in solution B is 0.5-2mol/L.
4. The use of the high selectivity Ag2C2O4/Ag2O composite catalyst according to claim 1 for the preparation of acetophenone by ethylbenzene oxidation, wherein the reaction time in S3 is 25-35min.
5. The application of the high-selectivity Ag2C2O4/Ag2O composite catalyst according to claim 1 in preparing acetophenone by ethylbenzene oxidation, wherein the calcination condition in S4 is pyrolysis reaction under air atmosphere, the heating rate is 2-5 ℃/min, the pyrolysis temperature is 120-180 ℃, the heat preservation time is 1.8-2.2h, and after the reaction is finished, the temperature is reduced for 1.5-2.5h to room temperature to obtain Ag 2 C 2 O 4 /Ag 2 O composite catalyst.
6. The high selectivity Ag of claim 1 2 C 2 O 4 /Ag 2 The application of the O composite catalyst in preparing acetophenone by ethylbenzene oxidation is characterized in that the method for preparing acetophenone by ethylbenzene oxidation catalyzed by the composite catalyst comprises the following steps: ethylbenzene and Ag 2 C 2 O 4 /Ag 2 Adding the O composite catalyst into a reactor for reaction, filtering the mixture at normal temperature and normal pressure after the reaction is finished, performing alkali washing and liquid separation on the filtrate, and distilling the upper liquid to obtain acetophenone.
7. The high-selectivity Ag of claim 6 2 C 2 O 4 /Ag 2 The application of the O composite catalyst in preparing acetophenone by ethylbenzene oxidation is characterized in that the Ag 2 C 2 O 4 /Ag 2 The dosage of the O composite catalyst is 2-3% of the molar quantity of ethylbenzene.
8. The high-selectivity Ag of claim 6 2 C 2 O 4 /Ag 2 The application of the O composite catalyst in preparing acetophenone by ethylbenzene oxidation is characterized in that the reaction conditions are as follows: stirring speed is 250rpm, air is used as an oxygen source, gas flow rate is kept at 100mL/min, reaction temperature is 120 ℃, and reaction time is 24 hours.
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| CN1762584A (en) * | 2005-09-09 | 2006-04-26 | 天津大学 | Integrated silver-supported catalyst, its preparation method and application in ethylene epoxy process |
| JP2014139291A (en) * | 2012-12-21 | 2014-07-31 | Fect Inc | Silver mirror film layer forming composition liquid, method of producing silver mirror film layer forming composition liquid and method of forming silver mirror film coating surface |
| CN108607556A (en) * | 2016-12-09 | 2018-10-02 | 中国石油化工股份有限公司 | A kind of preparation method and applications of silver catalyst |
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| CN1762584A (en) * | 2005-09-09 | 2006-04-26 | 天津大学 | Integrated silver-supported catalyst, its preparation method and application in ethylene epoxy process |
| JP2014139291A (en) * | 2012-12-21 | 2014-07-31 | Fect Inc | Silver mirror film layer forming composition liquid, method of producing silver mirror film layer forming composition liquid and method of forming silver mirror film coating surface |
| CN108607556A (en) * | 2016-12-09 | 2018-10-02 | 中国石油化工股份有限公司 | A kind of preparation method and applications of silver catalyst |
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