CN112645855A - Purification method and application of 4, 4-dichlorodiphenyl sulfone - Google Patents
Purification method and application of 4, 4-dichlorodiphenyl sulfone Download PDFInfo
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- CN112645855A CN112645855A CN202011554192.2A CN202011554192A CN112645855A CN 112645855 A CN112645855 A CN 112645855A CN 202011554192 A CN202011554192 A CN 202011554192A CN 112645855 A CN112645855 A CN 112645855A
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- dichlorodiphenyl sulfone
- elution
- purification
- dichlorodiphenyl
- sulfone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a purification method of 4, 4-dichlorodiphenyl sulfone and application thereof, wherein the purification method comprises the following steps: dissolving the 4, 4-dichlorodiphenyl sulfone crude product by using an eluent, feeding, and sending into a chromatographic column for elution to obtain a 4, 4-dichlorodiphenyl sulfone pure product; the adsorbent in the chromatographic column comprises silica gel or a molecular sieve. The purification method provided by the invention has the advantages of high purity, simple operation and no pollution to the environment.
Description
Technical Field
The invention belongs to the field of analytical chemistry, and particularly relates to a purification method and application of 4, 4-dichlorodiphenyl sulfone, in particular to a purification method and application of high-purity 4, 4-dichlorodiphenyl sulfone.
Background
4, 4-dichlorodiphenyl sulfone, DDS for short, has white monoclinic crystal appearance, is a main intermediate of engineering plastic polysulfone, is used for organic synthesis and drug synthesis, and can be used for synthesizing anti-infective drug acetidisulfone, such as 4,4' -diaminodiphenyl sulfone for treating leprosy. It is the main raw material for preparing engineering plastics such as polysulfone, polyethersulfone and the like; also is an intermediate of dye, auxiliary agent, pesticide and the like, and has very wide application in the fields of engineering plastics, medicine and health, electronic and electric appliances, aerospace and the like.
CN103601659A discloses a preparation method of 4, 4-dichlorodiphenyl sulfone, which proposes that chlorobenzene and p-chlorobenzenesulfonyl chloride are used as raw materials, and 4, 4-dichlorodiphenyl sulfone is obtained under the action of a catalyst and a small amount of polymerization inhibitor.
CN102351760A improves the chlorosulfonic acid method of 4, 4-dichlorodiphenyl sulfone, chlorobenzene, chlorosulfonic acid and dichloromethane react for 2 hours under the stirring of 25 ℃, then batch solid sodium chloride is added to continue the reaction for 2 hours, the obtained crude product of p-chlorobenzenesulfonyl chloride is dissolved in tetrachloroethylene solution, and reacts with chlorobenzene for 3 hours under the action of antimony pentachloride catalyst at room temperature, and then white 4, 4-dichlorodiphenyl sulfone is obtained.
At present, 4, 4-dichlorodiphenyl sulfone has immeasurable application in the fields of engineering plastics and fine chemical engineering, and a great number of preparation processes and method routes related to 4, 4-dichlorodiphenyl sulfone are developed. The researches all obtain good results, the industrial production is mature gradually, but an important problem is that how to obtain the high-purity 4, 4-dichlorodiphenyl sulfone so as to ensure the quality of the product. Therefore, how to provide a high-purity purification method of 4, 4-dichlorodiphenyl sulfone becomes a problem to be solved urgently.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for purifying 4, 4-dichlorodiphenyl sulfone and application thereof, in particular to a method for purifying high-purity 4, 4-dichlorodiphenyl sulfone and application thereof. The purification method provided by the invention has the advantages of high purity, simple operation and no pollution to the environment.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a method for purifying 4, 4-dichlorodiphenyl sulfone, comprising the steps of: dissolving the 4, 4-dichlorodiphenyl sulfone crude product by using an eluent, feeding, and sending into a chromatographic column for elution to obtain a 4, 4-dichlorodiphenyl sulfone pure product.
The adsorbent in the chromatographic column comprises silica gel or a molecular sieve.
The method purifies the 4, 4-dichlorodiphenyl sulfone crude product by selecting a specific adsorbent, an eluent and elution conditions, so that the purity of the obtained 4, 4-dichlorodiphenyl sulfone pure product can reach more than 98 percent, and the method is simple to operate and free of pollution to the environment.
Preferably, the silica gel comprises reverse phase silica gel comprising C18.
Preferably, the molecular sieve comprises an X-type molecular sieve or a Y-type molecular sieve.
The special adsorbent can sufficiently separate 4, 4-dichlorodiphenyl sulfone from other impurities.
Preferably, the eluting eluent comprises ethanol and/or acetonitrile.
Preferably, the rate of elution is from 0.1 to 5 mL/min.
Preferably, the rate of feed is from 0.1 to 10mL/min, preferably from 0.1 to 5 mL/min.
Preferably, the temperature of the elution is 0-100 ℃, preferably 20-80 ℃.
Preferably, the pressure of the elution is from 0.1 to 5MPa, preferably from 0.1 to 2 MPa.
Wherein the elution rate may be 0.1mL/min, 0.2mL/min, 0.3mL/min, 0.5mL/min, 1mL/min, 2mL/min, 3mL/min, 4mL/min or 5mL/min, etc., the feeding rate may be 0.1mL/min, 0.2mL/min, 0.3mL/min, 0.5mL/min, 1mL/min, 2mL/min, 3mL/min, 4mL/min, 5mL/min, 6mL/min, 7mL/min, 8mL/min, 9mL/min or 10mL/min, etc., the elution temperature is 0 ℃, 10 ℃, 20 ℃, 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃, 80 ℃, 90 ℃ or 100 ℃, etc., the elution pressure is 0.1MPa, 0.2MPa, 0.3, 0.5MPa, 1MPa, 1.5MPa, 2MPa, 2.5MPa, 3.5MPa, etc., the elution pressure is 0.1MPa, 1MPa, 1.5MPa, 2MPa, 3.5MPa, 3MPa, etc, 4MPa, 4.5MPa or 5MPa, but the above-mentioned values are not limited thereto, and other values not listed in the above-mentioned numerical range are also applicable.
The above specific feed rate and elution rate enable control of the purification effect such that 4, 4-dichlorodiphenyl sulfone is sufficiently separated from impurities.
Preferably, the impurities in the crude 4, 4-dichlorodiphenyl sulfone comprise 2, 4-dichlorodiphenyl sulfone and/or 2, 2-dichlorodiphenyl sulfone.
Preferably, the total mass fraction of the 2, 4-dichlorodiphenyl sulfone and 2, 2-dichlorodiphenyl sulfone is 0 to 25%, such as 0, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24% or 25%, etc., but not limited to the above-listed values, and other non-listed values within the above-mentioned range of values are equally applicable, preferably 0 to 15%, and more preferably 0 to 5%.
As a preferred technical scheme of the invention, the purification method comprises the following steps: dissolving the 4, 4-dichlorodiphenyl sulfone crude product with eluent, feeding, and feeding into a chromatographic column for elution under the conditions of 0-100 ℃ of temperature, 0.1-5MPa of pressure and 0.1-5mL/min of elution rate to obtain the 4, 4-dichlorodiphenyl sulfone pure product.
In another aspect, the invention also provides the application of the purification method of 4, 4-dichlorodiphenyl sulfone in the purification of 4, 4-dichlorodiphenyl sulfone.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a method for purifying 4, 4-dichlorodiphenyl sulfone, which can ensure that the purity of the obtained 4, 4-dichlorodiphenyl sulfone pure product reaches more than 98 percent by selecting a specific adsorbent, an eluent and elution conditions to purify a 4, 4-dichlorodiphenyl sulfone crude product, and has the advantages of simple operation and no environmental pollution.
Detailed Description
To further illustrate the technical means and effects of the present invention, the following further describes the technical solution of the present invention with reference to the preferred embodiments of the present invention, but the present invention is not limited to the scope of the embodiments.
In the following examples, the column is a column having a column length of 60cm and an inner diameter of 15 mm.
Introducing a solution with the weight content of target 4, 4-dichlorodiphenyl sulfone of 85 percent and the sum of the weight contents of 2, 4-dichlorodiphenyl sulfone and 2, 2-dichlorodiphenyl sulfone of 15 percent into a chromatographic column, and purifying according to the following conditions:
then, 4-dichlorodiphenyl sulfone crude products with different concentrations are purified at the temperature of 80 ℃, the pressure of 0.3MPa, the feeding rate of 0.5mL/min and the elution rate of 0.3mL/min, and the results are as follows:
the data show that the purification method of 4, 4-dichlorodiphenyl sulfone provided by the invention can be used for simply and conveniently purifying a 4, 4-dichlorodiphenyl sulfone crude product within the condition range provided by the invention, the purity of the purified product reaches more than 98%, and meanwhile, the purification method is free from environmental pollution and shows an excellent purification effect.
The applicant states that the present invention is illustrated by the above examples of the purification method of 4, 4-dichlorodiphenyl sulfone and the application thereof, but the present invention is not limited to the above examples, i.e. it does not mean that the present invention must be implemented by the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
Claims (10)
1. A purification method of 4, 4-dichlorodiphenyl sulfone, which is characterized by comprising the following steps: dissolving the 4, 4-dichlorodiphenyl sulfone crude product by using an eluent, feeding, and sending into a chromatographic column for elution to obtain a 4, 4-dichlorodiphenyl sulfone pure product;
the adsorbent in the chromatographic column comprises silica gel or a molecular sieve.
2. The method of purifying 4, 4-dichlorodiphenyl sulfone of claim 1 wherein the silica gel comprises reverse phase silica gel comprising C18;
preferably, the molecular sieve comprises an X-type molecular sieve or a Y-type molecular sieve.
3. The method for purifying 4, 4-dichlorodiphenyl sulfone according to claim 1 or 2, wherein the eluting solvent comprises ethanol and/or acetonitrile.
4. 4, 4-dichlorodiphenyl sulfone purification process according to any one of claims 1 to 3, characterized in that the elution rate is from 0.1 to 5 mL/min.
5. The process for the purification of 4, 4-dichlorodiphenyl sulfone according to any one of claims 1 to 4, wherein the rate of the feeding is 0.1 to 10mL/min, preferably 0.1 to 5 mL/min.
6. Process for the purification of 4, 4-dichlorodiphenyl sulfone according to any one of claims 1 to 5, characterized in that the temperature of elution is from 0 to 100 ℃, preferably from 20 to 80 ℃.
7. Process for the purification of 4, 4-dichlorodiphenyl sulfone according to any one of claims 1 to 6, characterized in that the pressure of elution is from 0.1 to 5MPa, preferably from 0.1 to 2 MPa.
8. The method for purifying 4, 4-dichlorodiphenyl sulfone according to any one of claims 1 to 7, wherein the impurities in the crude 4, 4-dichlorodiphenyl sulfone comprise 2, 4-dichlorodiphenyl sulfone and/or 2, 2-dichlorodiphenyl sulfone;
preferably, the total mass fraction of the 2, 4-dichlorodiphenyl sulfone and the 2, 2-dichlorodiphenyl sulfone is 0 to 25%, preferably 0 to 15%, and further preferably 0 to 5%.
9. The purification process of 4, 4-dichlorodiphenyl sulfone according to any one of claims 1 to 8, characterized in that it comprises the following steps: dissolving the 4, 4-dichlorodiphenyl sulfone crude product with eluent, feeding, and feeding into a chromatographic column for elution under the conditions of 0-100 ℃ of temperature, 0.1-5MPa of pressure and 0.1-5mL/min of elution rate to obtain the 4, 4-dichlorodiphenyl sulfone pure product.
10. Use of a method of purifying 4, 4-dichlorodiphenyl sulfone according to any one of claims 1 to 9 in the purification of 4, 4-dichlorodiphenyl sulfone.
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| CN202011554192.2A CN112645855A (en) | 2020-12-24 | 2020-12-24 | Purification method and application of 4, 4-dichlorodiphenyl sulfone |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104016892A (en) * | 2014-06-13 | 2014-09-03 | 吉林大学 | Difluoro-sulfone monomer containing double biphenyl structure and preparation method thereof |
| CN104710342A (en) * | 2014-10-28 | 2015-06-17 | 南京工业大学 | Synthetic method and application of diphenyl sulfone derivatives |
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2020
- 2020-12-24 CN CN202011554192.2A patent/CN112645855A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104016892A (en) * | 2014-06-13 | 2014-09-03 | 吉林大学 | Difluoro-sulfone monomer containing double biphenyl structure and preparation method thereof |
| CN104710342A (en) * | 2014-10-28 | 2015-06-17 | 南京工业大学 | Synthetic method and application of diphenyl sulfone derivatives |
Non-Patent Citations (2)
| Title |
|---|
| 沈淑予 等: "4,4’-二氯二苯砜单体的新合成方法研究", 《化学世界》 * |
| 赵临襄 主编: "《中国医药科技出版社》", 31 August 2015, 中国医药科技出版社 * |
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