CN102838518A - Preparation method of triphenyl sulfonium salt - Google Patents
Preparation method of triphenyl sulfonium salt Download PDFInfo
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- CN102838518A CN102838518A CN201210334606XA CN201210334606A CN102838518A CN 102838518 A CN102838518 A CN 102838518A CN 201210334606X A CN201210334606X A CN 201210334606XA CN 201210334606 A CN201210334606 A CN 201210334606A CN 102838518 A CN102838518 A CN 102838518A
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Abstract
The invention discloses a preparation method of triphenyl sulfonium salt. Triphenyl sulfonium is prepared from benzene, thionyl chloride and alchlor, and the reaction formula is described in the specification, wherein M is alkali metal or hydrogen, alkali metal can be K or Na, and X<-> is halogen anion or composite anion. According to the method, the used raw materials are chip and easily-obtained basic chemical raw materials, the cost of the raw materials is low, the production cost can be reduced greatly, the reaction conditions are moderate, and the method is easy to operate and realize industrialization.
Description
Technical field
The invention belongs to the fine chemical technology field, be specifically related to a kind of triphenyl sulfosalt novel preparation method.
Background technology
The triphenyl sulfosalt is used widely in 248nm and the photic resist of following deep ultraviolet in unicircuit, semi-conductor industry as a kind of New Photoinduced acidogenic agent.In addition, the triphenyl sulfosalt can also be applied in macromolecular material industry as the initiator of radical, cationoid polymerisation.
Synthetic about the triphenyl sulfosalt, public reported mainly contain 5 kinds of methods:
(1) aluminum chloride or alchlor catalysis method
The Journal of Organic Chemistry, 1968,33 (7): 2671-2675, reported that under big excessive aluminum chloride or alchlor catalysis thionyl benzene and benzene reaction obtain the triphenyl sulfosalt.
With triphenyl sulphur bromine salt is example, and reaction yield is 55%.This method lattice yield is moderate, but raw material thionyl benzene, alchlor price are more expensive, and total cost is high.
(2) Grignard reagent method
Journal of the American Chemical Society, 1951,73 (5): 1965-1967. has reported the synthetic route of aryl grignard reagent and thionyl benzene reaction, shown in the following equation:
With triphenyl sulphur bromine salt is example, and reaction yield is 49.4%.This method reaction needed is carried out severe reaction conditions under absolute anhydrous and oxygen-free condition; And raw material reagent price is more expensive, and total cost is high.
(3) Grignard reagent improved method
Synthesis2004, (10): reported the synthetic route of improved aryl grignard reagent and thionyl benzene reaction among the 1648-1654, shown in the following equation:
This method has been simplified Grignard reagent preparation technology, is catalyzer with the trimethylchlorosilane, has improved the nucleophilicity of reaction reagent, and reaction yield is higher.But still exist raw material reagent price more expensive, the shortcoming that total cost is high.
(4) diaryl group iodized salt method
The Journal of Organic Chemistry, 1978,43 (15): reported among the 3055-3058. being starting raw material with the diaryl group iodized salt, under mantoquita catalysis, prepared the method for triaryl sulfonium salts with diphenyl sulfide, shown in the following equation:
Though though this method products obtained therefrom yield is higher, the diaryl group iodized salt price is high, so present method shortcoming is that preparation cost is too high.
(5) methylsulfonic acid-Vanadium Pentoxide in FLAKES catalysis method
Though this method products obtained therefrom yield is higher, the thionyl benzene price is more expensive, so present method shortcoming is that preparation cost is too high.
Above-described several method all has significant disadvantage, is difficult to realize suitability for industrialized production.
Summary of the invention
Defective or deficiency to prior art exists the objective of the invention is to, and a kind of easy, novel preparation method cheaply of triphenyl sulfosalt is provided.
In order to realize above-mentioned task, the present invention takes following technical solution:
A kind of triphenyl sulfosalt preparation method is characterized in that this method is a raw material with benzene, sulfur oxychloride, aluminum chloride, and reaction formula is as follows:
In the formula, M is basic metal or hydrogen, and wherein, basic metal is selected K or Na; X is halide anion or composite anion.
Method of the present invention has the following advantages:
1, raw materials used all is cheap and easy basic chemical industry raw materials that get, and material cost is low, can reduce production costs significantly.
2, reaction conditions is gentle, easy handling and realization industriallization.
Embodiment
Below in conjunction with specific embodiment the present invention is explained further details.
According to technical scheme of the present invention, in following embodiment, adopting extremely cheap and easy benzene, sulfur oxychloride, the aluminum chloride that gets of price is raw material, and reaction obtains the triphenyl sulfosalt.Shown in the following reaction formula of technological line that adopts:
In the formula, M is basic metal or hydrogen, and wherein, basic metal is selected K or Na; X is halide anion or composite anion.
Below be the embodiment that the contriver provides, the invention is not restricted to these embodiment, the present invention can also amplify production, and its reaction conditions is gentle, and easy handling possesses fabulous industrial applications prospect.
Embodiment 1:
Accurately weighing aluminum trichloride (anhydrous) 52.74 grams, benzene 177ml join in the 500ml there-necked flask; Stirring and using ice-water bath to be cooled to system temperature is 10 ℃; Begin to drip the 11.9g sulfur oxychloride, drip the process reaction liquid temp and remain on about 20 ℃, about 15min dropwises.
After sulfur oxychloride dropwises, be warming up to 60 ~ 70 ℃, continue stirring reaction 10h.Question response liquid is cooled to room temperature, and it is added drop-wise in the 300ml water, and standing demix divides water-yielding stratum, and water layer washs with 100ml benzene, and benzene is discarded.
Add the 100ml mass concentration prepare in advance in the water layer after the washing again and be 33% potassium iodide aqueous solution, stirring reaction 2h separates out white solid.With 100ml dichloromethane extraction 2 times, concentrate evaporate to dryness.The gained solid is used the Virahol recrystallization, obtains white crystal 25.7g, and it is 99% that LC detects purity, and yield is 66%.
Embodiment 2:
Different is for present embodiment and embodiment 1, substitutes potassium iodide aqueous solution with the kbr aqueous solution of equivalent, and all the other are with embodiment 1.The gained solid is used the Virahol recrystallization, obtains white crystal 25.7g, and it is 99% that LC detects purity, yield 45%.
Claims (1)
1. a triphenyl sulfosalt preparation method is characterized in that, this method is a raw material with benzene, sulfur oxychloride, aluminum chloride, and reaction formula is as follows:
In the formula, M is basic metal or hydrogen, and wherein, basic metal is selected K or Na; X
-Be halide anion or composite anion.
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| CN201210334606XA CN102838518A (en) | 2012-09-11 | 2012-09-11 | Preparation method of triphenyl sulfonium salt |
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| CN201210334606XA CN102838518A (en) | 2012-09-11 | 2012-09-11 | Preparation method of triphenyl sulfonium salt |
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| CN102838518A true CN102838518A (en) | 2012-12-26 |
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| CN201210334606XA Pending CN102838518A (en) | 2012-09-11 | 2012-09-11 | Preparation method of triphenyl sulfonium salt |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354565A (en) * | 2021-05-06 | 2021-09-07 | 宁波南大光电材料有限公司 | Method for purifying magnesium ions in triphenyl sulfonium salt |
| CN114262286A (en) * | 2021-12-28 | 2022-04-01 | 宁波南大光电材料有限公司 | One-pot synthesis method of triphenyl sulfonium salt |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB794066A (en) * | 1955-01-17 | 1958-04-30 | Bayer Ag | New aromatic sulphonium compounds and a process for their production |
| CN101153016A (en) * | 2006-09-30 | 2008-04-02 | 北京英力科技发展有限公司 | Method for producing 3-(substituted phenyl) sulfur onium chloride salt |
| EP2042487A2 (en) * | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Production method of sulfonium salt compound |
| JP4921022B2 (en) * | 2006-04-20 | 2012-04-18 | 富士フイルム株式会社 | Method for producing sulfonium salt |
-
2012
- 2012-09-11 CN CN201210334606XA patent/CN102838518A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB794066A (en) * | 1955-01-17 | 1958-04-30 | Bayer Ag | New aromatic sulphonium compounds and a process for their production |
| JP4921022B2 (en) * | 2006-04-20 | 2012-04-18 | 富士フイルム株式会社 | Method for producing sulfonium salt |
| CN101153016A (en) * | 2006-09-30 | 2008-04-02 | 北京英力科技发展有限公司 | Method for producing 3-(substituted phenyl) sulfur onium chloride salt |
| EP2042487A2 (en) * | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Production method of sulfonium salt compound |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354565A (en) * | 2021-05-06 | 2021-09-07 | 宁波南大光电材料有限公司 | Method for purifying magnesium ions in triphenyl sulfonium salt |
| CN114262286A (en) * | 2021-12-28 | 2022-04-01 | 宁波南大光电材料有限公司 | One-pot synthesis method of triphenyl sulfonium salt |
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Application publication date: 20121226 |