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Preparation method of 2-isopropylthioxanthone

A technology of isopropylthioxanthone and cumene, which is applied in the field of photoinitiator preparation, achieves the effects of less waste, convenient post-processing, and high conversion rate

Inactive Publication Date: 2013-01-09
浙江凯普化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The application of transition metals and their modified tin-based solid superacids to synthesize thioxanthones by Friedel-Crafts acylation has not yet been reported.

Method used

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  • Preparation method of 2-isopropylthioxanthone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a 250 ml three-necked flask, add 122 grams (1 mole) of benzoic acid and 120 grams (1 mole) of cumene, S 2 o 8 2- / SnO 2 -Fe 2 o 3 Catalyst (Fe / Sn molar ratio is 1:9) 15 grams and sulfur 36 grams (1.1 mol), react at 80 ° C for 5 hours, after the reaction is completed, the reaction liquid is cooled to room temperature (25 ° C), and the reaction liquid Add 200 milliliters of toluene to it for extraction, filter, the filter cake is the recovery of solid superacid, and the filtrate is washed with 150 milliliters of saturated brine, dried with anhydrous magnesium sulfate, concentrated under reduced pressure to remove toluene, and the concentrated solution is subjected to silica gel column chromatography ( Petroleum ether: ethyl acetate = 10:1 (volume ratio)), TLC tracking detection, collecting the eluate containing the target component, drying to obtain 181 grams of light yellow solid product, namely 2-isopropylthioxanthone , the yield is 71%, the melting point is 73-...

Embodiment 2

[0027] In a 250 ml three-necked flask, add 122 g (1 mole) of benzoic acid and 120 g (1 mole) of cumene, SO 4 2- / SnO 2 -Fe 2 o 3 Catalyst (Fe / Sn molar ratio is 1:4) 36 grams, sulfur 36 grams (1.1 mol), react at 150 ° C for 1 hour, after the reaction is completed, the reaction liquid is cooled to room temperature, and toluene 200 is added to the reaction liquid milliliters for extraction, filtering, the filter cake is the recovery of solid super acid, the filtrate is washed with 150 milliliters of saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to remove toluene, and the concentrated solution is subjected to silica gel column chromatography (petroleum ether: acetic acid Ethyl ester = 10:1), TLC follow-up detection, collect the eluate containing the target component, and dry to obtain 178 grams of light yellow solid product, namely 2-isopropylthioxanthone, with a yield of 70% and a melting point of 73 ~75°C, the purity of the prod...

Embodiment 3

[0029] In a 250 ml three-necked flask, add 122 g (1 mole) of benzoic acid and 120 g (1 mole) of cumene, SO 4 2- / SnO 2 - 13 grams of ZnO catalyst (Zn / Sn molar ratio is 1:9), 36 grams of sulfur (1.1 moles), reacted at 100 ° C for 10 hours, after the reaction was completed, the reaction liquid was cooled to room temperature, and then added to the reaction liquid Extract with 200 ml of toluene, filter, and the filter cake is the recovery of solid superacid. The filtrate is washed with 150 ml of saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to remove toluene, and the concentrated solution is subjected to silica gel column chromatography (petroleum ether : ethyl acetate = 10:1), TLC tracking detection, collect the eluate containing the target component, dry to obtain 180 grams of light yellow solid product, namely 2-isopropylthioxanthone, yield 71%, The melting point is 73-75°C, and the purity of the product detected by HPLC reaches ...

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Abstract

The invention discloses a preparation method of 2-isopropylthioxanthone. The method comprises the following steps of: reacting benzoic acid serving as a raw material with cumene and sulfur by taking a solid super-acid as a catalyst at the temperature of 80-150 DEG C; after complete reaction, cooling a reaction liquid to the room temperature, and adding toluene for extracting; filtering; recovering a filter cake serving as a solid super-acid catalyst for reuse; washing a filtrate with a saturated saline solution, and drying with absolute magnesium sulfate; concentrating under reduced pressure for removing toluene; and performing silica gel column chromatography on a concentrated solution to obtain the 2-isopropyl thioxanthone. In the method, the solid super-acid is taken as a catalyst, a technology is easy to operate, high transformation ratio is achieved, a small quantity of three wastes are produced, convenience is brought to post-treatment, and the solid acid can be used repeatedly; and the method is an economical, practical and environment-friendly technology.

Description

(1) Technical field [0001] The invention relates to a preparation method of a photoinitiator, in particular to a preparation method of 2-isopropylthioxanthone by using a solid superacid one-pot method. (2) Background technology [0002] Thioxanthone compounds are a class of better photoinitiators with excellent optical properties, and can be used as synthetic intermediates of UV-curable materials, DNA fluorescent probes, and initiators in free radical polymerization reactions. The molecular weight of the polymer is controlled during the polymerization reaction. In addition, these compounds also have biological activities such as antitumor. At present, the synthesis methods of thioxanthone can be summarized as follows: 1) Polyphosphoric acid catalyzes the synthesis of thioxanthone compounds; 2) Utilizes concentrated sulfuric acid to catalyze the synthesis of thioxanthone compounds; 3) Synthesis of sulfur Xanthone compounds; 4) Synthesis of thioxanthone compounds through ben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/16
Inventor 孙莉裴文胡卫雅潘镇浩全嘉铭
Owner 浙江凯普化工有限公司
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