CN115260023A - Novel synthesis method of 3, 4-dimethoxy-4-chloro-benzophenone - Google Patents
Novel synthesis method of 3, 4-dimethoxy-4-chloro-benzophenone Download PDFInfo
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- CN115260023A CN115260023A CN202210520480.9A CN202210520480A CN115260023A CN 115260023 A CN115260023 A CN 115260023A CN 202210520480 A CN202210520480 A CN 202210520480A CN 115260023 A CN115260023 A CN 115260023A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- 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
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Abstract
The invention discloses a novel method for synthesizing 3, 4-dimethoxy-4-chloro-benzophenone, which particularly relates to the field of chemical production and comprises the following specific synthesis steps: preparing raw materials, namely filling the immobilized catalyst into a fixed bed, and respectively filling the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride into a storage tank; carrying out synthetic reaction, firstly starting a fixed bed heating device, and simultaneously starting three delivery pumps to deliver the o-dimethyl ether and the dichloro-dimethyl ether in three storage tanks when the temperature reaches 40 DEG CFeeding ethane and p-chlorobenzoyl chloride into a fixed bed, respectively, o-phthalic acid and p-chlorobenzoyl chloride in SO4 2‑/ZrO2Carrying out Friedel-crafts reaction under a solid super acidic catalyst; collecting a synthetic product, dissolving the product generated by the Friedel-crafts reaction in a dichloroethane extractant, firstly adding water into a fixed bed reactor for washing, standing and separating the reaction liquid, carrying out atmospheric pressure batch rectification on the lower oil phase, and then collecting an oil layer material from a discharge port, wherein the oil layer material is 3, 4-dimethoxy-4-chloro-benzophenone.
Description
Technical Field
The invention relates to the technical field of chemical production, in particular to a novel synthesis method of 3, 4-dimethoxy-4-chloro-benzophenone.
Background
The pure 3, 4-dimethoxy-4-chloro-benzophenone is a white crystal, is insoluble in water, can be dissolved in organic solvents such as alcohol, ether and chloroform, and has a chemical formula of C15H13ClO3Molecular weight is 276.71492, is an intermediate of bactericide dimethomorph.
Dimethomorph is a cinnamic acid derivative, has unique effect on downy mildew of phycomycetes and phytophthora fungi, is a relatively ideal efficient broad-spectrum bactericide, has relatively high bactericidal power on oomycetes of grapes, potatoes and tomatoes, particularly on downy mildew and phytophthora fungi, and is used for preventing and treating grape phytophthora blight, potato late blight and the like. Has the characteristics of small dosage, long lasting period, safe use and the like, and has good market prospect.
The traditional method for producing and synthesizing 3, 4-dimethoxy-4-chloro-benzophenone generally takes phthalic ether, aluminum chloride and p-chlorobenzoyl chloride as raw materials, and the raw materials are obtained through Friedel-crafts reaction, wherein the aluminum chloride is used as a catalyst (catalyst). The aluminum chloride required by the process is difficult to recover after reaction, a large amount of waste water needs to be treated, and the environmental protection pressure is extremely high.
The pure o-dimethyl ether is colorless liquid or crystal, is soluble in ethanol, diethyl ether and fatty oil, is slightly soluble in water, and has molecular formula C8H10O2And the molecular weight is 138.17.
The p-chlorobenzoyl chloride is a colorless liquid, is insoluble in water, is soluble in ethanol, diethyl ether and acetone, and has a molecular formula of C7H4Cl2O, molecular weight 175.01.
Disclosure of Invention
In order to overcome the above-mentioned drawbacks of the prior art, the embodiments of the present invention provide a novel method for synthesizing 3, 4-dimethoxy-4-chlorobenzophenone by substituting an aluminum chloride catalyst for a sulfate ion acidic metal oxide SO42-/ZrO2Solid superacid and a synthetic method designed to solve the problems set forth in the background art.
In order to achieve the purpose, the invention provides the following technical scheme: comprises o-dimethyl ether, p-chlorobenzoyl chloride, an organic solvent extracting agent and a catalyst, and the specific synthesis steps are as follows:
s1, preparing raw materials, namely filling the immobilized catalyst into a fixed bed, and respectively filling phthalic ether, dichloroethane and p-chlorobenzoyl chloride into storage tanks;
s2, carrying out synthetic reaction, namely firstly starting a fixed bed heating device, starting three conveying pumps at the same time when the temperature reaches 40 ℃, respectively conveying the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride in three storage tanks into the fixed bed, and respectively conveying the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride in SO4 2-/ZrO2Carrying out Friedel-crafts reaction under a solid super acidic catalyst;
and S3, collecting a synthetic product, dissolving 3, 4-dimethoxy-4-chloro-benzophenone generated by the Friedel-crafts reaction in a dichloroethane extracting agent, firstly adding water into a fixed bed reactor for washing, standing reaction liquid to obtain a lower oil phase for liquid separation, carrying out atmospheric pressure batch rectification, then collecting an oil layer material from a discharge port, wherein the oil layer material is the 3, 4-dimethoxy-4-chloro-benzophenone, and finally discharging wastewater to a wastewater pool.
In a preferred embodiment, the supported catalyst is SO in this example4 2-/ZrO2The solid super acidic catalyst has the characteristics of no corrosion to reaction devices, environmental protection and reutilization, and can easily activate C-C bond C-H bond to generate carbonA positive ion.
In a preferred embodiment, the fixed bed reactor comprises a feeding port and a discharging port, the feeding port is connected with three storage tanks, the storage tanks are respectively filled with a phthalic ether solution, a p-chlorobenzoyl chloride solution and an organic solvent, and the solution in the storage tanks is conveyed into the fixed bed reactor through a conveying pump.
In a preferred embodiment, the flow rate of the o-phthalic ether is 100 kg per hour, the flow rate of the p-chlorobenzoyl chloride is 138 kg per hour, the flow rate of the dichloroethane is 400 kg per hour, and the catalyst can be operated continuously for more than 3000 hours.
In a preferred embodiment, the SO4 2-/ZrO2The preparation method of the solid super acidic catalyst has a preparation schematic diagram as shown in figure 3, and comprises the following specific steps:
a1 with the corresponding zirconium salts, e.g. ZrNO3,ZrOCl2Preparing zirconium hydroxide precipitate by the solution and ammonia water, and then washing away impurity ions in the precipitate by using distilled water;
a2, containing SO4 2-H of (A) to (B)2SO4Or (NH)4)SO4The solution is used for treating zirconium hydroxide precipitate, and the zirconium hydroxide precipitate is roasted at a proper temperature to obtain the catalyst.
In a preferred embodiment, said SO4 2-/ZrO2In the preparation process of the solid super acidic catalyst, the PH value is controlled to be 10, the roasting temperature is controlled to be 650 ℃, and normal ZrOCl is removed by selecting zirconium salt2And ZrO (NO)3)2In addition, zrC1 is used4,Zr(NO3)4,Zr(OC3H7)4Other zirconium salts are used as the starting material for the zirconium hydroxide, the choice of which will influence the ZrO support2The phase of (1). For example with ZrC14ZrO formed by precipitation and roasting2The Zr-0 crystal has both monoclinic phase and tetragonal phase structure, and ZrOCI is used as a precipitant to finally form the Zr-0 crystal with only tetragonal phase structure.
The invention has the technical effects and advantages that:
1. the novel synthesis method of the 3, 4-dimethoxy-4-chloro-benzophenone shortens the reaction time by using the fixed bed reactor, has small backmixing and higher selectivity, and effectively inhibits the generation of side reactions;
2. the novel synthesis method of 3, 4-dimethoxy-4-chloro-benzophenone comprises the step of using sulfate ion acidic metal oxide SO capable of being recycled4 2-/ZrO2The solid super acidic catalyst (catalyst) is convenient to prepare, simple and convenient in post-treatment of catalytic reaction, wide in temperature application range, capable of being used under the conditions of low temperature and high temperature, greatly reducing the amount of three wastes, and enabling the process to have good operability, safety and environmental protection.
Drawings
FIG. 1 is a schematic diagram of the synthesis method of the present invention.
FIG. 2 shows the chemical reaction scheme of the synthesis of the present invention.
FIG. 3 is a SO according to the invention4 2-Schematic diagram of the preparation method of ZrO.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention.
The embodiment of the invention provides a schematic diagram of a synthetic method shown in figure 1 and a synthetic chemical reaction formula of 3, 4-dimethoxy-4-chloro-benzophenone shown in figure 2.
Example 1
The materials required by the embodiment of the invention are o-dimethyl ether, p-chlorobenzoyl chloride, an organic solvent extractant and a catalyst, wherein the catalyst is sulfate ion acidic metal oxide SO4 2-/ZrO2Solid super acid, the organic solvent extractant is dichloroethane, which is used for extracting 3, 4-dimethoxy-4-chloro-benzophenone synthesized in the reaction and synthesizing reaction sitesIs a fixed bed reactor.
The embodiment of the invention introduces a synthesis method of 3, 4-dimethoxy-4-chloro-benzophenone, which comprises the following specific synthesis steps:
s1, preparing raw materials, namely loading the immobilized catalyst 1 into a fixed bed reactor, and respectively loading phthalic ether, dichloroethane and p-chlorobenzoyl chloride into a storage tank;
the supported catalyst is SO in this example4 2-/ZrO2The solid super acidic catalyst has the characteristics of no corrosion to a reaction device, environmental friendliness and reusability, and can easily activate C-C bond C-H bond to generate carbocation.
The fixed bed reactor comprises a feed inlet and a discharge outlet, the feed inlet is connected with three storage tanks, a phthalic ether solution, a parachlorobenzoyl chloride solution and an organic solvent are respectively filled in the storage tanks, and the solution in the storage tanks is conveyed into the fixed bed reactor through a conveying pump.
S2, carrying out synthetic reaction, namely firstly starting a fixed bed heating device, starting three conveying pumps simultaneously when the temperature reaches 40 ℃, respectively conveying the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride in the three storage tanks into the fixed bed, and carrying out SO reaction on the o-dimethyl ether, the p-chlorobenzoyl chloride and the p-chlorobenzoyl chloride4 2-/ZrO2Carrying out Friedel-crafts reaction under a solid super acidic catalyst;
the flow rate of the o-phthalic ether is 100 kilograms per hour, the flow rate of the p-chlorobenzoyl chloride is 138 kilograms per hour, the flow rate of the dichloroethane is 400 kilograms per hour, and the catalyst can continuously operate for more than 3000 hours.
And S3, collecting a synthetic product, dissolving 3, 4-dimethoxy-4-chloro-benzophenone generated by the Friedel-crafts reaction in a dichloroethane extracting agent, firstly adding water into a fixed bed reactor for washing, standing reaction liquid to obtain a lower oil phase for liquid separation, carrying out atmospheric pressure batch rectification, then collecting an oil layer material from a discharge port, wherein the oil layer material is the 3, 4-dimethoxy-4-chloro-benzophenone, and finally discharging wastewater to a wastewater pool.
In the embodiment of the invention, SO4 2-/ZrO2Solid superacid catalystProcess for the preparation of Agents, SO4 2-The preparation steps of/ZrO are shown in figure 3, and the specific steps are as follows:
a1 with the corresponding zirconium salts, e.g. ZrNO3,ZrOCl2Preparing zirconium hydroxide precipitate by the solution and ammonia water, and then washing away impurity ions in the precipitate by using distilled water;
a2, will contain SO4 2-H of (A) to (B)2SO4Or (NH)4)SO4The solution is used for treating zirconium hydroxide precipitate, and the zirconium hydroxide precipitate is roasted at a proper temperature to obtain the catalyst.
In the preparation process, the PH value is controlled to be 10, and the roasting temperature is controlled to be 650 ℃.
In the preparation process, the zirconium salt is selected to remove the normal ZrOCl2And ZrO (NO)3)2In addition, zrC1 is used4,Zr(NO3)4，Zr(OC3H7)4Other zirconium salts are used as the starting material for the zirconium hydroxide, the choice of which will influence the ZrO content of the support2The phase of (2). For example with ZrC14ZrO formed by precipitation and roasting2The intermediate has both monoclinic phase and tetragonal phase structure, while ZrOCI is used as a precipitant to finally form Zr0 with only tetragonal phase structure.
Example 2
The embodiment of the invention introduces a method for synthesizing 3, 4-dimethoxy-4-chloro-benzophenone, which comprises the following specific steps:
s1, preparing raw materials, namely filling the immobilized catalyst into a fixed bed, and respectively filling phthalic ether, dichloroethane and p-chlorobenzoyl chloride into storage tanks;
s2, carrying out synthetic reaction, namely firstly starting a fixed bed heating device, starting three conveying pumps at the same time when the temperature reaches 50 ℃, respectively conveying the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride in three storage tanks into the fixed bed, and respectively conveying the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride in SO4 2-/ZrO2Carrying out Friedel-crafts reaction under a solid super acidic catalyst;
the flow rate of the o-phthalic ether is 100 kilograms per hour, the flow rate of the p-chlorobenzoyl chloride is 138 kilograms per hour, the flow rate of the dichloroethane is 400 kilograms per hour, and the catalyst can continuously operate for more than 2400 hours.
And S3, collecting a synthetic product, dissolving 3, 4-dimethoxy-4-chloro-benzophenone generated by the Friedel-crafts reaction in a dichloroethane extractant, firstly adding water into a fixed bed reactor for washing, standing the reaction liquid to obtain a lower oil phase for liquid separation, carrying out normal-pressure intermittent rectification, then collecting an oil layer material from a discharge port, wherein the oil layer material is the 3, 4-dimethoxy-4-chloro-benzophenone, and finally discharging wastewater to a wastewater pool.
SO in the examples of the invention4 2-/ZrO2The preparation method of the solid super acidic catalyst 2 comprises the following specific steps:
a1, with the corresponding zirconium salts, e.g. ZrNO3,ZrOCl2Preparing zirconium hydroxide precipitate by the solution and ammonia water, and then washing away impurity ions in the precipitate by using distilled water;
a2, containing SO4 2-H of (A)2SO4Or (NH)4)SO4The solution is used for treating zirconium hydroxide precipitate, and the zirconium hydroxide precipitate is roasted at a proper temperature to obtain the catalyst.
In the preparation process, the pH value is controlled to be 8, and the roasting temperature is controlled to be 550 ℃.
Example 3
The embodiment of the invention introduces a method for synthesizing 3, 4-dimethoxy-4-chloro-benzophenone, which comprises the following specific steps:
s1, preparing raw materials, namely filling the immobilized catalyst into a fixed bed, and respectively filling the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride into a storage tank;
the supported catalyst is SO in this example4 2-/ZrO2The solid super acidic catalyst has the advantages of no corrosion to reaction equipment, environmental protection and reusability, and can easily activate C-C bond C-H bond to generate carbocation.
S2, carrying out synthetic reaction, namely firstly starting a fixed bed heating device, simultaneously starting three delivery pumps when the temperature is 60 ℃, and respectively delivering the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride in three storage tanksInto a fixed bed, o-phthalic and p-chlorobenzoyl chloride in SO4 2-/ZrO2Carrying out Friedel-crafts reaction under a solid super acidic catalyst;
the flow rate of the o-dimethyl ether is 100 kilograms per hour, the flow rate of the p-chlorobenzoyl chloride is 138 kilograms per hour, the flow rate of the dichloroethane is 400 kilograms per hour, and the catalyst can continuously run for more than 2000 hours.
And S3, collecting a synthetic product, dissolving 3, 4-dimethoxy-4-chloro-benzophenone generated by the Friedel-crafts reaction in a dichloroethane extractant, firstly adding water into a fixed bed reactor for washing, standing the reaction liquid to obtain a lower oil phase for liquid separation, carrying out normal-pressure intermittent rectification, then collecting an oil layer material from a discharge port, wherein the oil layer material is the 3, 4-dimethoxy-4-chloro-benzophenone, and finally discharging wastewater to a wastewater pool.
SO in the examples of the invention4 2-/ZrO2The preparation method of the solid super acidic catalyst comprises the following specific steps:
a1 with the corresponding zirconium salts, e.g. ZrNO3,ZrOCl2Preparing zirconium hydroxide precipitate by the solution and ammonia water, and then washing out impurity ions in the precipitate by distilled water;
a2, containing SO4 2-H of (A)2SO4Or (NH)4)SO4The solution is used for treating zirconium hydroxide precipitate, and the zirconium hydroxide precipitate is roasted at a proper temperature to obtain the catalyst.
In the preparation process, the PH value is controlled to be 9, and the roasting temperature is controlled to be 700 ℃.
Examples of the experiments
By comparing the catalytic performance, catalyst operating time and catalyst state in examples 1, 2 and 3, the highest catalytic activity was obtained when the pH was controlled to 10 and the calcination temperature was controlled to about 650 ℃.
Because of the formation of Zr (OH)4The pH at the time of precipitation influences not only the basic physical properties of the catalyst, such as particle size, specific surface area and pore structure, but also the ZrO content of the support2The phase of (2) and the catalytic performance of the final catalyst, at a pH of 7, cannot be obtainedSO4 2-/ZrO2While when the pH was 10, SO was successfully obtained4 2-/ZrO2Solid acids, if the pH is too low, the precipitation of entrapped harmful ions such as C1-It is difficult to remove.
In the preparation process, the roasting temperature is controlled within 650 ℃, the roasting temperature determines the sulfur content on the surface of the catalyst and the phase of metal oxide, when the roasting temperature is too low, enough strong acid centers cannot be formed, and when the roasting temperature is too high, the catalyst can be decomposed, the surface area is reduced, and the strong acid structure is damaged, through comparative experiments, when the roasting temperature is lower (550 ℃) and higher (700 ℃), the prepared catalyst has lower catalytic activity, and when the roasting temperature is about 650 ℃, the catalytic activity is highest.
And finally: the above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (7)
1. A new synthesis method of 3, 4-dimethoxy-4-chloro-benzophenone comprises the steps of phthalic ether, p-chlorobenzoyl chloride, an organic solvent extractant and a catalyst, and is characterized in that: the specific synthesis steps are as follows:
s1, preparing raw materials, namely filling the immobilized catalyst into a fixed bed, and respectively filling phthalic ether, dichloroethane and p-chlorobenzoyl chloride into storage tanks;
s2, carrying out synthetic reaction, namely firstly starting a fixed bed heating device, starting three conveying pumps simultaneously when the temperature reaches 40 ℃, respectively conveying the o-dimethyl ether, the dichloroethane and the p-chlorobenzoyl chloride in the three storage tanks into the fixed bed, and carrying out SO reaction on the o-dimethyl ether, the p-chlorobenzoyl chloride and the p-chlorobenzoyl chloride4 2-/ZrO2Carrying out Friedel-crafts reaction under a solid super acidic catalyst;
and S3, collecting a synthetic product, dissolving 3, 4-dimethoxy-4-chloro-benzophenone generated by the Friedel-crafts reaction in a dichloroethane extractant, firstly adding water into a fixed bed reactor for washing, standing and separating the reaction liquid, carrying out normal-pressure intermittent rectification on the lower oil phase, then collecting oil layer materials from a discharge port, wherein the oil layer materials are the 3, 4-dimethoxy-4-chloro-benzophenone, and finally discharging the wastewater to a wastewater pool.
2. The novel process for the synthesis of 3, 4-dimethoxy-4-chloro-benzophenone as claimed in claim 1, wherein: the supported catalyst is SO in this example4 2-/ZrO2The solid super acidic catalyst has the characteristics of no corrosion to a reaction device, environmental friendliness and reusability, and can easily activate C-C bond C-H bond to generate carbocation.
3. The novel process for the synthesis of 3, 4-dimethoxy-4-chloro-benzophenone as claimed in claim 1, wherein: the fixed bed reactor comprises a feed inlet and a discharge outlet, the feed inlet is connected with three storage tanks, a phthalic ether solution, a p-chlorobenzoyl chloride solution and an organic solvent are respectively filled in the storage tanks, and the solution in the storage tanks is conveyed into the fixed bed reactor through a conveying pump.
4. The novel process for the synthesis of 3, 4-dimethoxy-4-chloro-benzophenone as claimed in claim 1, wherein: the flow rate of the o-dimethyl ether is 100 kilograms per hour, the flow rate of the p-chlorobenzoyl chloride is 138 kilograms per hour, the flow rate of the dichloroethane is 400 kilograms per hour, and the catalyst can continuously operate for more than 3000 hours.
5. The novel method for synthesizing 3, 4-dimethoxy-4-chloro-benzophenone as claimed in claim 1, wherein: the SO4 2-/ZrO2The preparation method of the solid super acidic catalyst has a preparation schematic diagram as shown in figure 3, and comprises the following specific steps:
a1 with the corresponding zirconium salts, e.g. ZrNO3,ZrOCl2Preparing zirconium hydroxide precipitate by the solution and ammonia water, and then washing out impurity ions in the precipitate by distilled water;
a2, containing SO4 2－H of (A) to (B)2SO4Or (NH)4)SO4The solution is used for treating zirconium hydroxide precipitate, and the zirconium hydroxide precipitate is roasted at a proper temperature to obtain the catalyst.
6. The SO of claim 44 2-/ZrO2The preparation method of the solid super acidic catalyst is characterized by comprising the following steps: in the preparation process, the PH value is controlled to be 10, and the roasting temperature is controlled to be 650 ℃.
7. SO according to claim 44 2-/ZrO2The preparation method of the solid super acidic catalyst is characterized by comprising the following steps: during the preparation process, zrOCl is selectively removed from the zirconium salt2And ZrO (NO)3)2ZrC1 may be used in addition to4,Zr(NO3)4，Zr(OC3H7)4As a raw material of zirconium hydroxide.
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| CN116768766A (en) * | 2023-05-19 | 2023-09-19 | 锦州三丰科技有限公司 | Preparation method of 4,4' -dichlorodiphenyl sulfone |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116768766A (en) * | 2023-05-19 | 2023-09-19 | 锦州三丰科技有限公司 | Preparation method of 4,4' -dichlorodiphenyl sulfone |
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