CN102351758A - New preparation method of 4,4-dichlorodiphenyl sulfone - Google Patents
New preparation method of 4,4-dichlorodiphenyl sulfone Download PDFInfo
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- CN102351758A CN102351758A CN2011102459507A CN201110245950A CN102351758A CN 102351758 A CN102351758 A CN 102351758A CN 2011102459507 A CN2011102459507 A CN 2011102459507A CN 201110245950 A CN201110245950 A CN 201110245950A CN 102351758 A CN102351758 A CN 102351758A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 10
- 230000001590 oxidative effect Effects 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 9
- 239000012074 organic phase Substances 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 7
- 239000012452 mother liquor Substances 0.000 claims abstract description 6
- 239000007800 oxidant agent Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 19
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000035484 reaction time Effects 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 3
- 230000007935 neutral effect Effects 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000001816 cooling Methods 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- KJGYFISADIZFEL-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfinylbenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)C1=CC=C(Cl)C=C1 KJGYFISADIZFEL-UHFFFAOYSA-N 0.000 abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a new preparation method of 4,4-dichlorodiphenyl sulfone. The method comprises the following steps: 1) through using AlCl3 as a catalyst, and chlorobenzene and thionyl chloride as reaction raw materials, performing a Friedel-Crafts reaction at 25-35 DEG C, then hydrolyzing the mother liquor obtained through the Friedel-Crafts reaction, refluxing at 95-100 DEG C for 45-60 minutes, cooling the obtained mother liquor to less than 20 DEG C after refluxing to obtain an organic phase and an aqueous phase; 2) performing reduced pressure distillation on the organic phase, centrifuging, washing the obtained product to be neutral and be used as a product A for later use, wherein the main component of the product A is 4,4-dichlorodiphenyl sulfoxide; and 3) through using the product A and the oxidant hydrogen peroxide as raw materials and acetic acid as satalytic solvent, carrying out an oxidation reaction on the main component 4,4-dichlorodiphenyl sulfoxide of the product A to obtain crude 4,4-dichlorodiphenyl sulfone. Therefore, the existing synthesis method of 4,4-dichlorodiphenyl sulfone is changed, the production cost of 4,4-dichlorodiphenyl sulfone is low, the product quality is good and the reaction time is short.
Description
Technical field
The present invention relates to a kind of preparation method of 4.4 – dichloro diphenyl sulfones.
Background technology
4.4 the – dichloro diphenyl sulfone is called for short DDS, is white crystal, can distil, and is soluble in organic solvents such as benzene, chlorobenzene, DMF; Be slightly soluble in ethanol, methyl alcohol; Water insoluble.Its flash-point is 233 ℃, and boiling point then is 397 ℃.
4.4 the – dichloro diphenyl sulfone has purposes widely at engineering plastics and field of fine chemical, is the main raw material of engineering plastics such as preparation polysulfones, polyethersulfone, also is the intermediate of medicine, dyestuff, agricultural chemicals.
At present, the synthesis method of Chang Yong 4.4 – dichloro diphenyl sulfones has: chlorsulfonic acid method, sulfuric acid process and sulphur trioxide method; Wherein, the production cost that the chlorsulfonic acid legal system is equipped with 4.4 – dichloro diphenyl sulfones is high, serious three wastes, and quality product is poor, is difficult to reach the specification of quality of polysulfones and polyethersulfone production defined; The sulfuric acid process temperature of reaction is high, and long reaction time is serious to equipment corrosion, poor product quality, and yield is low; The whole operational path of sulphur trioxide method is long, and the friedel-crafts reaction temperature is high, long reaction time, and the process for refining route is complicated.
Summary of the invention
The present invention is directed to the deficiency of prior art, a kind of new preparation process of 4.4 – dichloro diphenyl sulfones is provided, it is low that it has a production cost, good product quality, the advantage that the reaction times is short.
For realizing above technical purpose, the present invention will take following technical scheme:
A kind of new preparation process of 4.4 – dichloro diphenyl sulfones; May further comprise the steps: at first; With AlCl3 is catalyzer; Chlorobenzene, thionyl chloride are reaction raw materials, between 25-35 degree centigrade, carry out friedel-crafts reaction, then; Mother liquor after the friedel-crafts reaction end is hydrolyzed; Hydrolysis finishes the back at 95-100 degree centigrade of refluxed 45-60min, reflux finish after, be cooled to and be divided into organic phase and water below 20 ℃; To neutrality, subsequent use as products A, the main composition in the products A is 4.4 – dichloro thionyl benzenes to organic phase through underpressure distillation, centrifuge washing; Then, be raw material with products A, oxidant hydrogen peroxide, acetate is that the catalysis solvent carries out oxidizing reaction to the 4.4 – dichloro thionyl benzenes of the main composition in the products A, synthetic 4.4 – dichloro diphenyl sulfone crude products.
According to above technical scheme, can realize following beneficial effect:
It is reaction raw materials that the present invention adopts chlorobenzene, thionyl chloride earlier; With AlCl3 is catalyzer; Preparing main composition is the products A of 4.4 – dichloro thionyl benzenes, adopts oxidant hydrogen peroxide, oxide catalyst acetate that 4.4 – dichloro thionyl benzenes are carried out oxidation again, obtains 4.4 – dichloro diphenyl sulfone crude products; Hence one can see that, and the present invention changes the synthesis method of existing 4.4 – dichloro diphenyl sulfones, causes the production cost of 4.4 – dichloro diphenyl sulfones low, good product quality, and the reaction times is short.
Embodiment
Below will combine embodiment that technical scheme of the present invention at length is described.
The new preparation process of 4.4 – dichloro diphenyl sulfones of the present invention, the pharmaceutical chemicals of employing has: catalyst A lCl3, chlorobenzene, thionyl chloride, oxidant hydrogen peroxide and catalysis solvent acetic acid; Specifically may further comprise the steps:
The preparation of (1) 4.4 – dichloro thionyl benzene
With AlCl3 is catalyzer; Chlorobenzene, thionyl chloride are reaction raw materials; Between 25-35 degree centigrade, carry out friedel-crafts reaction; Then; Mother liquor after the friedel-crafts reaction end is hydrolyzed; Hydrolysis finishes the back at 95-100 degree centigrade of refluxed 45-60min, reflux finish after, be cooled to and be divided into organic phase and water below 20 ℃; To neutrality, subsequent use as products A, the main composition in the products A is 4.4 – dichloro thionyl benzenes to organic phase through underpressure distillation, centrifuge washing.
1, in the reaction kettle of the dry cleansing that disposes device for absorbing tail gas, metering drops into Benzene Chloride, and stirs cooling;
2, in reaction kettle, drip an amount of sulfur oxychloride earlier, behind the stirring 10min, add required lewis acid alchlor, closed reactor stirs 20min;
3, when reacting liquid temperature during, drip the sulfur oxychloride of metering at 25 degrees centigrade; In this step, need in the whole dropping process of control, reacting liquid temperature is all the time between 25-35 degree centigrade, and the dropping time was controlled between 3.4-4.5 hour;
4, after step 3 finishes, be incubated 40min down at 35-45 degree centigrade, the speed with 1 degree centigrade/min is warming up to 70-80 ℃ then, prepares hydrolysis;
5, in hydrolysis kettle, be metered into tap water, the material that step 4 reaction is good slowly adds in this hydrolysis kettle that fills tap water, behind reinforced the finishing, is warming up to 100 ℃, and backflow 60min allows its abundant hydrolysis; Reflux after the end, be cooled to below 20 ℃, follow blowing, and will tell organic layer in the mother liquor suction separatory still, do distillation and handle, alchlor wastewater collection sale;
6, material carries out centrifugal, washing to neutral, packing.Washing water are made hydrolysis kettle hydrolysis water in next circulation.The product sampling analysis, and put on lot number.This product is 4.4 – dichloro thionyl benzene crude products.
The preparation of (2) 4.4 – dichloro diphenyl sulfones
With products A, oxidant hydrogen peroxide is raw material, and acetate is that the catalysis solvent carries out oxidizing reaction to the 4.4 – dichloro thionyl benzenes of the main composition in the products A, synthetic 4.4 – dichloro diphenyl sulfone crude products; After oxidizing reaction finishes, blowing, suction filtration, tell organic layer, organic layer washing to neutral after drying, packing are got final product.
Claims (1)
1. the new preparation process of a – dichloro diphenyl sulfone; It is characterized in that; May further comprise the steps: at first, be catalyzer with AlCl3, chlorobenzene, thionyl chloride are reaction raw materials; Between 25-35 degree centigrade, carry out friedel-crafts reaction; Then, the mother liquor after the friedel-crafts reaction end is hydrolyzed, hydrolysis finishes the back at 95-100 degree centigrade of refluxed 45-60min; After reflux finishing, be cooled to and be divided into organic phase and water below 20 ℃; To neutrality, subsequent use as products A, the main composition in the products A is 4.4 – dichloro thionyl benzenes to organic phase through underpressure distillation, centrifuge washing; Then, be raw material with products A, oxidant hydrogen peroxide, acetate is that the catalysis solvent carries out oxidizing reaction to the 4.4 – dichloro thionyl benzenes of the main composition in the products A, synthetic 4.4 – dichloro diphenyl sulfone crude products.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011102459507A CN102351758A (en) | 2011-08-25 | 2011-08-25 | New preparation method of 4,4-dichlorodiphenyl sulfone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011102459507A CN102351758A (en) | 2011-08-25 | 2011-08-25 | New preparation method of 4,4-dichlorodiphenyl sulfone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102351758A true CN102351758A (en) | 2012-02-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011102459507A Pending CN102351758A (en) | 2011-08-25 | 2011-08-25 | New preparation method of 4,4-dichlorodiphenyl sulfone |
Country Status (1)
| Country | Link |
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| CN (1) | CN102351758A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104402780A (en) * | 2014-12-12 | 2015-03-11 | 山东凯盛新材料有限公司 | Synthesis process of 4, 4'-dichlorodiphenyl sulfone |
| CN104557626A (en) * | 2014-12-12 | 2015-04-29 | 山东凯盛新材料有限公司 | Process for preparing 4,4'-dichlorodiphenylsulfone employing sulfoxide oxidation method |
| CN105348155A (en) * | 2015-12-14 | 2016-02-24 | 山东凯盛新材料有限公司 | Synthesis process of 4,4'-dichlorodiphenyl sulfone |
| CN106349126A (en) * | 2016-08-25 | 2017-01-25 | 江西金海新能源科技有限公司 | Method for preparing 4,4'-dichloro sulfobenzide |
| CN108047101A (en) * | 2017-12-07 | 2018-05-18 | 九江中星医药化工有限公司 | A kind of synthesis technology of high-efficiency and continuous production 4,4- dichloro diphenyl sulfones |
| CN110642762A (en) * | 2019-09-13 | 2020-01-03 | 辽宁君荣化工有限公司 | Preparation method of 4, 4-dichlorodiphenyl sulfone |
| WO2020161225A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | Process for purifying 4,4'-dichlorodiphenyl sulfoxide |
| WO2020161232A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | Process for producing 4,4'-dichlorodiphenyl sulfoxide |
| WO2020161226A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | A process for obtaining 4,4'-dichlorodiphenyl sulfoxide |
| WO2020161228A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | Process for producing 4,4`-dichlorodiphenyl sulfoxide |
| WO2020207929A1 (en) | 2019-04-09 | 2020-10-15 | Basf Se | Process for working up a composition comprising solid 4,4'-dichlorodiphenyl sulfoxide and a solvent |
| WO2021037683A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for purifying 4,4'-dichlorodiphenyl sulfone |
| WO2021037680A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for obtaining 4,4'-dichlorodiphenyl sulfone |
| WO2021037672A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for producing 4,4'-dichlorodiphenyl sulfone |
| WO2021037675A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | Process for producing 4,4'-dichlorodiphenyl sulfone |
| WO2021037682A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for purifying crude 4,4'-dichlorodiphenyl sulfone |
| DE102020113957A1 (en) | 2020-05-25 | 2021-11-25 | Basf Se | Process for working up carboxylic acid-moist 4,4-dichlorodiphenyl sulfone |
| CN114507165A (en) * | 2022-04-20 | 2022-05-17 | 富海(东营)新材料科技有限公司 | Method for synthesizing 4, 4' -dichlorodiphenyl sulfone by solid acid catalysis |
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Cited By (22)
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| CN104402780A (en) * | 2014-12-12 | 2015-03-11 | 山东凯盛新材料有限公司 | Synthesis process of 4, 4'-dichlorodiphenyl sulfone |
| CN104557626A (en) * | 2014-12-12 | 2015-04-29 | 山东凯盛新材料有限公司 | Process for preparing 4,4'-dichlorodiphenylsulfone employing sulfoxide oxidation method |
| CN104402780B (en) * | 2014-12-12 | 2016-04-27 | 山东凯盛新材料有限公司 | 4, the synthesis technique of 4 '-dichloro diphenyl sulfone |
| CN105348155A (en) * | 2015-12-14 | 2016-02-24 | 山东凯盛新材料有限公司 | Synthesis process of 4,4'-dichlorodiphenyl sulfone |
| CN106349126A (en) * | 2016-08-25 | 2017-01-25 | 江西金海新能源科技有限公司 | Method for preparing 4,4'-dichloro sulfobenzide |
| CN106349126B (en) * | 2016-08-25 | 2018-06-01 | 江西金海新能源科技有限公司 | The method for preparing 4,4 '-dichloro diphenyl sulfone |
| CN108047101A (en) * | 2017-12-07 | 2018-05-18 | 九江中星医药化工有限公司 | A kind of synthesis technology of high-efficiency and continuous production 4,4- dichloro diphenyl sulfones |
| WO2020161226A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | A process for obtaining 4,4'-dichlorodiphenyl sulfoxide |
| WO2020161225A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | Process for purifying 4,4'-dichlorodiphenyl sulfoxide |
| WO2020161232A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | Process for producing 4,4'-dichlorodiphenyl sulfoxide |
| US12168642B2 (en) | 2019-02-08 | 2024-12-17 | Basf Se | Process for producing 4,4′-dichlorodiphenyl sulfoxide |
| WO2020161228A1 (en) | 2019-02-08 | 2020-08-13 | Basf Se | Process for producing 4,4`-dichlorodiphenyl sulfoxide |
| WO2020207929A1 (en) | 2019-04-09 | 2020-10-15 | Basf Se | Process for working up a composition comprising solid 4,4'-dichlorodiphenyl sulfoxide and a solvent |
| WO2021037680A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for obtaining 4,4'-dichlorodiphenyl sulfone |
| WO2021037683A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for purifying 4,4'-dichlorodiphenyl sulfone |
| WO2021037672A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for producing 4,4'-dichlorodiphenyl sulfone |
| WO2021037675A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | Process for producing 4,4'-dichlorodiphenyl sulfone |
| WO2021037682A1 (en) | 2019-08-27 | 2021-03-04 | Basf Se | A process for purifying crude 4,4'-dichlorodiphenyl sulfone |
| CN110642762A (en) * | 2019-09-13 | 2020-01-03 | 辽宁君荣化工有限公司 | Preparation method of 4, 4-dichlorodiphenyl sulfone |
| DE102020113957A1 (en) | 2020-05-25 | 2021-11-25 | Basf Se | Process for working up carboxylic acid-moist 4,4-dichlorodiphenyl sulfone |
| CN114507165A (en) * | 2022-04-20 | 2022-05-17 | 富海(东营)新材料科技有限公司 | Method for synthesizing 4, 4' -dichlorodiphenyl sulfone by solid acid catalysis |
| CN114507165B (en) * | 2022-04-20 | 2022-07-19 | 富海(东营)新材料科技有限公司 | Method for synthesizing 4, 4' -dichlorodiphenyl sulfone by solid acid catalysis |
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Application publication date: 20120215 |