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Preparation method of photoinitiator 1-chloro-4-propoxythioxanthone

A technology of propoxythioxanthone and photoinitiator, applied in organic chemistry and other directions, can solve problems such as low yield and dark product color, and achieve the effects of simple post-processing, reduced raw material cost, and mild reaction conditions

Inactive Publication Date: 2018-08-24
JIAN DONGQING FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These processes need to be completed in two steps, the yield is low, and the product color is dark

Method used

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  • Preparation method of photoinitiator 1-chloro-4-propoxythioxanthone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Condensation ring reaction: Add 48 grams of p-chlorophenol and 40 grams of 2-mercaptobenzoic acid into a 1000ml four-necked bottle filled with 240 grams of 88-90% concentrated sulfuric acid, heat up to 60°C and react for 6-10 hours After the reaction, the reaction solution was cooled to room temperature, poured into 300 grams of ice water and 200 grams of methyl ethyl ketone, mixed and stirred, left to stand to obtain a layered solution, and the upper aqueous layer was removed to obtain the lower organic layer.

[0026] (2) Etherification reaction: Add 27 grams of potassium carbonate and 38 grams of bromopropane to the above organic layer, heat up to 80° C. and react for more than 5 hours under stirring, and cool down to 40° C. after HPLC detection until the intermediate reaction is complete.

[0027] (3) 260 g of water was added to the above reaction system for washing, and the layers were separated after standing, and the obtained organic layer was subjected to des...

Embodiment 2

[0030] (1) Condensation ring reaction: Add 20 grams of p-chlorophenol and 20 grams of 2-mercaptobenzoic acid into a 1000ml four-necked bottle filled with 200 grams of 88-90% concentrated sulfuric acid, heat up to 70°C and react for 6-10 hours After the reaction, the reaction solution was cooled to room temperature, poured into 300 grams of ice water and 140 grams of methyl ethyl ketone, mixed and stirred, left to stand to obtain a layered solution, and the upper aqueous layer was removed to obtain the lower organic layer.

[0031] (2) Etherification reaction: Add 20 grams of potassium carbonate and 24 grams of bromopropane to the above organic layer, heat up to 80° C. and react for more than 5 hours under stirring, and cool down to 40° C. after HPLC detection until the intermediate reaction is complete.

[0032] (3) Add 250 g of water to the above reaction system for washing, let stand to separate the layers, and carry out desolvation of the obtained organic layer under reduced...

Embodiment 3

[0035] (1) Condensation ring reaction: 35 grams of p-chlorophenol and 30 grams of 2-mercaptobenzoic acid are added to a 1000ml four-necked bottle of 400 grams of 88-90% concentrated sulfuric acid, and the temperature is raised to 70°C for 6-10 hours. After the reaction, the reaction solution was cooled to room temperature, poured into 400 g of ice water and 300 g of methyl ethyl ketone, mixed and stirred, and allowed to stand to obtain a layered solution. The upper aqueous layer was removed to obtain the lower organic layer.

[0036] (2) Etherification reaction: Add 29 grams of potassium carbonate and 33 grams of bromopropane to the above organic layer, heat up to 80° C. and react for more than 5 hours under stirring. After the intermediate reaction is completely detected by HPLC, the temperature is lowered to 40° C.

[0037] (3) 340 g of water was added to the above reaction system for washing, and the layers were separated after standing, and the obtained organic layer was su...

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Abstract

The invention discloses a preparation method of a photoinitiator 1-chloro-4-propoxythioxanthone. The method comprises the following steps: step 1, carrying out condensation ring formation reaction: adding 2-mercaptobenzoic acid and p-chlorophenol into concentrated sulfuric acid and extracting to obtain a corresponding organic product; step 2, directly carrying out etherification reaction, withoutthe need of separation and purification: adding 1-halogenated propane and alkali into an obtained organic layer; finally, carrying out decompression and desolvation, de-coloring, filtering and vacuumdrying on an etherified product to obtain a final product, i.e., the photoinitiator 1-chloro-4-propoxythioxanthone. Compared with the prior art, the yield is greatly improved, reaction conditions aremoderate and post-treatment is simple; the preparation method is a production method suitable for industrialization.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of a photoinitiator 1-chloro-4-propoxythioxanthone. Background technique [0002] 1-Chloro-4-propoxythioxanthone, English name 1-Chloro-4-Propoxy Thioxanthone (CPTX for short), molecular formula: C16H13ClO2S, molecular weight: 304.79, CAS registration number: [142770-42-1]. 1-Chloro-4-propoxythioxanthone was first successfully developed by British Great Lakes Company. Because of its longer UV absorption wavelength and faster photocuring speed, it is widely used in UV-curable coatings and inks. [0003] The synthetic technique of 1-chloro-4-propoxythioxanthone is basically similar at present, all is to use dithiosalicylic acid or 2-mercaptobenzoic acid as raw material, first carries out condensation with p-chlorophenol to form a ring, and then Etherification with 1-bromopropane or 1-chloropropane under alkaline conditions to finally obtain the target...

Claims

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Application Information

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IPC IPC(8): C07D335/16C08F2/48
CPCC07D335/16C08F2/48
Inventor 曾孝军
Owner JIAN DONGQING FINE CHEM
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