CN110183308B - Nonmetal catalyst for preparing phenol by directly oxidizing benzene, preparation method and application - Google Patents
Nonmetal catalyst for preparing phenol by directly oxidizing benzene, preparation method and application Download PDFInfo
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Abstract
A nonmetal catalyst for preparing phenol by directly oxidizing benzene is prepared by dissolving p-benzoquinone and diamine in methanol respectively; then, after the two solutions are uniformly mixed, dropwise adding hydrogen peroxide into the mixed solution; transferring the mixture into a high-pressure reaction kettle, reacting for 4-12 h at 120-160 ℃, and filtering to obtain a nonmetal catalyst; the nonmetal catalyst can catalyze oxygen to oxidize benzene to prepare phenol at 120-150 ℃ under the conditions that acetic acid aqueous solution is used as a solvent and acetate is used as an additive, so that better phenol yield is obtained. The nonmetal catalyst prepared by the method can catalyze oxygen to oxidize benzene to prepare phenol, so that the use of a catalyst containing heavy metal is avoided.
Description
Technical Field
The invention belongs to the technical field of novel catalyst preparation and energy chemical industry, and particularly relates to a preparation method and application of a nonmetal catalyst for preparing phenol by directly oxidizing benzene.
Background
Phenol is an important chemical intermediate and bulk basic raw material for petrochemical industry. At present, the industrial production method of phenol is mainly an isopropyl benzene method, and has the defects of long reaction process, low atom utilization rate and low total yield (< 5%). Therefore, in recent years, various countries around the world have been devoted to research on a green process for producing phenol, in which direct oxidation of benzene to produce phenol is receiving wide attention as a new economical green process for producing phenol. The oxygen as a green oxidant has the advantages of wide source, low price and the like, and the oxidation product is water, so that a byproduct polluting the environment is not generated. Therefore, the method for preparing phenol by directly oxidizing benzene by using oxygen as an oxidant has important theoretical and practical application significance.
Catalysts generally used in the reaction of benzene oxidation to produce phenol are transition metal-containing catalysts. In patent CN102921419A, supported catalyst containing copper is used for catalyzing benzene oxidation to prepare phenol; in patent CN102228833A, a porous material containing cobalt is used as a catalyst to catalyze benzene oxidation to prepare phenol; in patent CN104926614A, a metal organic framework compound HKUST-1 containing copper is used as a catalyst to catalyze benzene for oxidation to prepare phenol; the literature reports that catalysts containing transition metals such as vanadium, iron, palladium and the like catalyze the oxygen oxidation of benzene to produce phenol [ (a) Wang WT, Li N, Tang H, et al Molecular catalysis, 2018,453,113-120; (b) Qin Q, Liu YQ, Shann WJ, et al Industrial & Engineering Chemistry Research, 2017, 56 (43), 12289-12296; Shang SS, Yang H, Li J, et al Chemplus 2014, 79 (5), 680-683 ]. The reaction for oxidizing benzene with oxygen to produce phenol is generally carried out in an acidic reaction solvent. The metal catalyst is easy to have active center loss in an acid solvent, so that the problems of reduction of catalytic activity, pollution caused by heavy metal ions and the like are caused, the stability of the catalyst is difficult to ensure, the production cost of phenol is increased, and people pay attention to the economy and environmental protection. Therefore, the nonmetal catalyst is promoted to be developed and applied to the research of green phenol preparation. So far, no literature is reported on the preparation of a nonmetal catalyst by using p-benzoquinone and diamine and the preparation of phenol by using the nonmetal catalyst as a catalyst to catalyze the oxygen oxidation of benzene.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a preparation method and an application method of a nonmetal catalyst for preparing phenol by directly oxidizing benzene, so that the use of a metal-containing catalyst in the reaction of preparing phenol by directly oxidizing benzene is avoided, the problem of metal loss is avoided, the stability of the catalyst is improved, and the prepared catalyst shows better phenol yield in the reaction of preparing phenol by catalyzing oxygen to oxidize benzene.
In order to achieve the purpose, the invention adopts the technical scheme that:
the catalyst is a nonmetal catalyst prepared by taking p-benzoquinone and diamine as raw materials, and the active centers of the catalyst are benzoquinone and hydroquinone, so that nonmetal catalysis of preparing phenol by directly oxidizing benzene with oxygen is realized.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of a nonmetal catalyst for preparing phenol by directly oxidizing benzene comprises the following steps:
the method comprises the following steps: respectively dissolving p-benzoquinone and diamine in a methanol solution according to a molar ratio of 6: 1-1.5: 1 to obtain a methanol solution A of the p-benzoquinone and a methanol solution B of the diamine;
step two: adding the solution A obtained in the step one into the solution B, and uniformly stirring to obtain a solution C;
step three: dropwise adding 1-3 mL of hydrogen peroxide into the solution C obtained in the step two, uniformly stirring, and transferring the solution into a high-pressure reaction kettle;
step four: and adding the high-pressure autoclave at 120-160 ℃ for 4-12 h, filtering the obtained solid product, washing the solid product with methanol and distilled water until the filtrate is colorless and transparent, and drying to obtain the non-metal catalyst.
Further, the molar ratio of the p-benzoquinone to the diamine is 6: 1-1.5: 1.
Further, the diamine comprises ethylenediamine, propylenediamine, hexamethylenediamine, o-phenylenediamine and melamine.
Furthermore, the hydrogen peroxide is 10-30% in mass concentration and 1-3 mL in dosage.
Further, the four heating steps are carried out at the temperature of 120-160 ℃ for 4-12 hours.
A non-metal catalyst for preparing phenol by directly oxidizing benzene is prepared by the preparation method of the solid acid catalyst.
A catalytic application method based on the nonmetal catalyst comprises the following steps:
the method comprises the following steps: adding 0.025-0.2 g of the nonmetal catalyst, 0.5-1.0 mL of benzene, 0.2-0.8 g of acetate and 3.0mL of acetic acid water solution with the volume fraction of 50% -100% into a high-pressure reaction kettle;
step two: filling oxygen pressure of 1.0-4.0 MPa into the reaction kettle;
step three: and stirring the reaction kettle at the temperature of between 120 and 150 ℃ for reaction for 12 to 24 hours to obtain the product phenol.
Further, the acetate in the first step is lithium acetate and sodium acetate, and the using amount of the acetate is 0.2-0.8 g.
Further, the reaction solvent in the step one is an acetic acid aqueous solution with the volume concentration of 50-100%.
Further, the oxygen pressure in the second step is 1.0-4.0 MPa.
Further, the reaction temperature in the third step is 120-150 ℃.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention uses benzoquinone and diamine as simple raw materials, and can prepare the nonmetal catalyst through simple polymerization reaction, and the active center of the nonmetal catalyst is mainly the contained quinone-hydroquinone functional group. The nonmetal catalyst can be directly used as a catalyst for catalyzing oxygen to oxidize benzene to prepare phenol, so that the pollution of the use of the metal catalyst and the loss of heavy metals to the environment is avoided; the yield of the phenol prepared by catalyzing oxygen to oxidize benzene can reach the same level as that of the phenol prepared by catalyzing benzene by using a metal catalyst, and the catalyst has better catalytic activity; in addition, the preparation method of the catalyst is simple, efficient and convenient, and has the advantages of high catalytic activity, high yield and the like.
Drawings
FIG. 1 is a FT-IR plot of quinone amine polymers prepared from different amine sources. In the figure, (a) ethylenediamine, (b) propylenediamine, (c) hexamethylenediamine, (d) o-phenylenediamine, and (e) melamine.
FIG. 2 is an SEM spectrum of the non-metal catalyst obtained by the present invention.
Detailed Description
The present invention will be further illustrated with reference to the following examples.
Example 1
Respectively dissolving 30mmol of p-benzoquinone and 10mmol of ethylenediamine in methanol, adding the p-benzoquinone solution into the ethylenediamine solution, stirring uniformly, and slowly dropwise adding 1 mL of 30% (wt.) H2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 3 MPa of O at room temperature2Reaction at 120 deg.c for 24 hr to obtain phenol in 13.1% yield.
Example 2
Respectively dissolving 20mmol of p-benzoquinone and 10mmol of ethylenediamine in methanol, adding the p-benzoquinone solution into the ethylenediamine solution, stirring uniformly, and slowly dropwise adding 1 mL of 30% (wt.) H2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 3 MPa of O at room temperature2Reaction at 120 deg.c for 12 hr gave phenol in 5.4% yield.
Example 3
Respectively dissolving 30mmol of p-benzoquinone and 10mmol of propylenediamine in methanol, adding the p-benzoquinone solution into the ethylenediamine solution, stirring uniformly, and slowly dropwise adding 1 mL of 30% (wt.) H2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 3 MPa of O at room temperature2Reaction at 120 deg.c for 12 hr gave phenol in 15.9% yield.
Example 4
Respectively dissolving 30mmol of p-benzoquinone and 10mmol of hexamethylenediamine in methanol, adding the p-benzoquinone solution into the ethylenediamine solution, stirring uniformly, and slowly dropwise adding 1 mL of 30% (wt.) H2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 2 MPa of O at room temperature2Reaction at 120 deg.c for 12 hr to obtain phenol in 15% yield.
Example 5
Respectively dissolving 30mmol of p-benzoquinone and 10mmol of o-phenylenediamine in methanol, adding the p-benzoquinone solution into the ethylenediamine solution, stirring uniformly, and slowly dropwise adding 1 mL of 30% (wt.) H2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 2 MPa of O at room temperature2Reaction at 120 deg.c for 12 hr gave phenol in 5.1% yield.
Example 6
Respectively dissolving 30mmol of p-benzoquinone and 10mmol of ethylenediamine in methanol, and adding the p-benzoquinone solution to the ethyleneAfter stirring the diamine solution uniformly, slowly adding 2 mL of 20% (wt.) H dropwise2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 130 ℃ for 7 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 3 MPa of O at room temperature2Reaction at 120 deg.c for 12 hr gave phenol in 5.2% yield.
Example 7
Respectively dissolving 30mmol of p-benzoquinone and 10mmol of ethylenediamine in methanol, adding the p-benzoquinone solution into the ethylenediamine solution, stirring uniformly, and slowly dropwise adding 1 mL of 30% (wt.) H2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.2g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 3 MPa of O at room temperature2Reaction at 120 deg.c for 24 hr to obtain phenol in 6.4% yield.
Example 8
Respectively dissolving 30mmol of p-benzoquinone and 10mmol of ethylenediamine in methanol, adding the p-benzoquinone solution into the ethylenediamine solution, stirring uniformly, and slowly dropwise adding 1 mL of 30% (wt.) H2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of lithium acetate into 70% by volume of acetic acid solution, and charging 2 MPa of O at room temperature2Reaction at 140 deg.c for 24 hr to obtain phenol in 12.9% yield.
Example 9
30mmol of p-benzeneDissolving quinone and 10mmol ethylenediamine in methanol respectively, adding p-benzoquinone solution into ethylenediamine solution, stirring, and slowly adding 1 mL of 30% (wt.) H dropwise2O2. The solution was stirred to mix thoroughly and transferred to a high pressure autoclave equipped with a teflon liner and heated at 120 ℃ for 5 h. The resulting product was filtered, washed with 30 mL of methanol, and dried overnight at 80 ℃ to give a non-metallic catalyst.
Adding 0.1 g of catalyst, 0.5mL of benzene and 0.4 g of sodium acetate into 70% by volume of acetic acid solution, and charging 2 MPa O at room temperature2Reaction at 120 deg.c for 12 hr gave 14.3% yield of phenol.
Claims (6)
1. The application of the nonmetal catalyst in the preparation of phenol is characterized by comprising the following steps:
placing a dispersion containing benzene, acetate, 50-100% volume concentration acetic acid aqueous solution and a nonmetal catalyst in a high-pressure container; charging oxygen gas with pressure of more than 1.0MPa into the high-pressure container; fully reacting the reaction system at 120-150 ℃ to obtain phenol;
the acetate is one or more of lithium acetate and sodium acetate;
the nonmetal catalyst is obtained by dispersing p-benzoquinone, diamine organic matters and hydrogen peroxide in sufficient organic solvent and carrying out solvothermal reaction at 120-160 ℃;
the diamine organic matter is one or more of ethylenediamine, propylenediamine, hexamethylenediamine and o-phenylenediamine.
2. The use according to claim 1, wherein the molar ratio of p-benzoquinone to organic diamine is (6-1.5): 1.
3. The application of claim 1, wherein the mass concentration of the hydrogen peroxide is 10-30% when the nonmetal catalyst is prepared.
4. The application of claim 1, wherein when the nonmetal catalyst is prepared, the solvent used in the solvothermal reaction is methanol, the reaction temperature is 120-160 ℃, and the reaction time is 4-12 hours.
5. The use according to any one of claims 1 to 4, wherein the preparation of the non-metallic catalyst comprises the following specific steps:
the method comprises the following steps: respectively dissolving p-benzoquinone and diamine organic matters in a methanol solution according to a molar ratio of 6: 1-1.5: 1 to obtain a methanol solution A of the p-benzoquinone and a methanol solution B of the diamine organic matters;
step two: adding the solution A obtained in the step one into the solution B, and uniformly stirring to obtain a solution C;
step three: dropwise adding 1-3 mL of hydrogen peroxide with the mass concentration of 10% -30% into the solution C obtained in the step two, uniformly stirring, and transferring the solution into a high-pressure reaction kettle;
step four: and (3) reacting the high-pressure kettle at 120-160 ℃ for 4-12 h, filtering to obtain a solid product, washing the solid product with methanol and distilled water until the filtrate is colorless and transparent, and drying to obtain the non-metal catalyst.
6. The use according to claim 1, characterized in that the specific steps comprise:
the method comprises the following steps: adding 0.025-0.2 g of the nonmetal catalyst, 0.5-1.0 mL of benzene, 0.2-0.8 g of acetate and 3.0mL of acetic acid water solution with the volume concentration of 50% -100% into a high-pressure reaction kettle;
step two: filling oxygen pressure of 1.0-4.0 MPa into the reaction kettle;
step three: and stirring the reaction kettle at the temperature of between 120 and 150 ℃ for reaction for 12 to 24 hours to obtain the product phenol.
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CN106831352A (en) * | 2016-12-19 | 2017-06-13 | 江苏师范大学 | A kind of method of the direct phenol processed of dioxygen oxidation benzene |
CN107519910A (en) * | 2017-09-12 | 2017-12-29 | 陕西科技大学 | It is a kind of to prepare support type vanadic acid Zr catalyst of phenol and preparation method thereof for oxygen direct oxidation benzene |
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CN106831352A (en) * | 2016-12-19 | 2017-06-13 | 江苏师范大学 | A kind of method of the direct phenol processed of dioxygen oxidation benzene |
CN107519910A (en) * | 2017-09-12 | 2017-12-29 | 陕西科技大学 | It is a kind of to prepare support type vanadic acid Zr catalyst of phenol and preparation method thereof for oxygen direct oxidation benzene |
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