Method for synthesizing (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate

A technology of methylbenzylsulfonium hexafluoroantimonate and methylbenzylsulfonium, which is applied in the field of organic chemical industry synthesis, can solve the problem of difficult separation and high purity of 4-hydroxyanisole, 4-hydroxyanisole and 4-hydroxyanisole. The problems such as the difficulty of obtaining the raw materials of anisole sulfide can achieve the effects of simple process, high purity and easy availability of raw materials

Inactive Publication Date: 2016-05-04
WUHAN INSTITUTE OF TECHNOLOGY
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Problems solved by technology

JP2013100237 reported a preparation of (4-hydroxyphenyl)methylbenzylsulfonium hexafluoroantimonate by reacting 4-hydroxyanisole sulfide as raw material with benzyl chloride. The method has simple process and high yield , but the 4-hydroxyanisole sulfide raw material is not easy to get, the document JPH08245558 and the Journal of Chemical Engineering of Universities, 2003, 17 (2) Shi Jiehua et al. reported that phenol is used as a raw material, and it is obtained by reacting with dimethyl disulfide under the action of concentrated sulfuric acid 4-hydroxyanisole sulfide, but at the same time there is 2-hydroxyanisole sulfide as a by-product, the ratio of 4-hydroxyanisole sulfide to 2-hydroxyanisole sulfide is between 85:15-70:30, Because the boiling points of the two are very close, it is difficult to separate, and the boiling point of 4-hydroxyanisole sulfide (20mmHg): 153-156 ° C, melting point: 83-85 ° C, it is difficult to obtain high-purity 4-hydroxy anisole sulfide
Therefore, this method is difficult to achieve large-scale industrial production

Method used

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  • Method for synthesizing (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate

Examples

Experimental program
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Effect test

Embodiment 1

[0027] 1, the preparation of 4-(benzylthio)phenol:

[0028] Add 12.6g (0.1mol) of 4-mercaptophenol and 12.12g (0.12mol) of triethylamine into a three-necked reaction flask with a thermometer and an electric stirrer, and dropwise add 12.6 (0.1mol) of benzyl chloride between 10°C 100ml of chloroform solution, the dropwise addition time is 2h. Then warm up to reflux for 6h. After the reaction is complete, pour it into 150ml of water, separate several layers, wash with 3×100ml of water, dry over anhydrous sodium sulfate, concentrate to obtain a yellow solid 4-(benzylthio)phenol, and then recrystallize with anhydrous methanol to obtain a yellow Solid 20.7g yield 96%. 1 HNMR (400MHz, CDCl 3 )δ7.20-7.05(m,7H),6.66-6.58(m,2H),5.34(s,1H),3.89(s,2H);

[0029] 2. Preparation of (4-hydroxyphenyl)methylbenzylsulfonium sulfate:

[0030] Add 21.6g (0.1mol) of 4-(benzylthio)phenol into a three-necked reaction flask with a thermometer and an electric stirrer, add 150ml of toluene, and add...

Embodiment 2

[0034] 1, the preparation of 4-(benzylthio)phenol:

[0035] Add 12.6g (0.1mol) of 4-mercaptophenol and 16.56g (0.12mol) of potassium carbonate into a three-necked reaction flask with a thermometer and an electric stirrer, and add 100ml of benzyl bromide 17.0 (0.1mol) dropwise between 10°C Toluene solution, the dropwise addition time is 2h. Then warm up to reflux for 6h. After the reaction is complete, pour it into 150ml of water, separate several layers, wash with 3×100ml of water, dry over anhydrous sodium sulfate, concentrate to obtain a yellow solid 4-(benzylthio)phenol, and then recrystallize with anhydrous methanol to obtain a yellow Solid 20.3g yield 94%.

[0036] 2. Preparation of (4-hydroxyphenyl)methylbenzylsulfonium iodide:

[0037] Weigh 21.6g (0.1mol) of 4-(benzylthio)phenol into a three-necked reaction flask with a thermometer and an electric stirrer, add 150ml of toluene, and drop 50ml of 20.02g (0.12mol) of potassium iodide below 15°C Toluene solution was ad...

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Abstract

The invention relates to a method for synthesizing (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate. The method includes the following steps that in a solvent, 4-mercaptophenol or benzyl chloride or benzyl bromide serves as a raw material, and 4-(benzylthio) phenol is prepared under the action of triethylamine or potassium carbonate or sodium carbonate; in a toluene or cyclohexane or chloroform or dichloroethane solution, 4-(benzylthio) phenol and dimethyl sulfate or potassium iodide are methylated to obtain (4-hydroxyphenyl) methyl benzyl sulfonium sulfate or (4-hydroxyphenyl) methyl benzyl sulfonium iodate; in a methanol or alcohol or isopropanol solution, (4-hydroxyphenyl) methyl benzyl sulfonium sulfate and sodium hexafluoroantimonate are subjected to ion exchange to obtain the target product (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate. The method has the advantages that the raw materials are easy to obtain, the technology is simple, the prepared 4-(benzylthio) phenol is high in purity and does not need to be refined, and the requirement for large-scale industrial production of (4-hydroxyphenyl) methyl benzyl sulfonium hexafluoroantimonate can be met.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a synthesis method of a cationic photoinitiator, in particular to a synthesis method of (4-hydroxyphenyl)methylbenzylsulfonium hexafluoroantimonate. Background technique [0002] With people's general attention to environmental protection, traditional curing is greatly restricted because it needs to use more volatile organic solvents that pollute the environment. Photocuring is widely used for its remarkable advantages such as low curing temperature, fast curing speed, and low pollution. favor. As one of the main components of photocuring composition, photoinitiator has naturally become a hotter research object. The cationic photoinitiator sulfonium salt has the advantages of photolysis to generate long-lived cations, can continue to initiate polymerization after removing radiation, and is insensitive to O2 without N2 protection. Devices prepared by sulfonium sa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/12
CPCC07C381/12C07C319/14C07C321/28
Inventor 刘安昌余彩虹张树康
Owner WUHAN INSTITUTE OF TECHNOLOGY
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