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Preparation method of 2-isopropyl thioxanthone and derivatives thereof

A technology of isopropylthioxanthone and derivatives is applied in the field of preparation of 2-isopropylthioxanthone and derivatives thereof, and can solve the problem that the acylation raw material 4-isopropylanisole is expensive, The tetralin solvent is expensive and complicated to operate, so as to achieve the effect of low price, low cost and high purity

Inactive Publication Date: 2010-09-01
TIANJIN JIURI NEW MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the tetralin solvent is expensive, pollutes the environment, and is complicated to operate
There are many disadvantages in this reaction, such as expensive acylation raw material 4-isopropylanisole, difficult recovery of N,N-dimethylformamide solvent, and low yield.

Method used

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  • Preparation method of 2-isopropyl thioxanthone and derivatives thereof
  • Preparation method of 2-isopropyl thioxanthone and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Preparation of 2-isopropylthioxanthone

[0020] Mix 130g (0.83mol) o-chlorobenzoic acid, 120g (0.79mol) 4-isopropylthiophenol, 68g (1.70mol) sodium hydroxide, 50mL water, heat to 80°C and stir for 0.5 hours, add 520mL toluene , Heat reflux for dehydration. The resulting solution is protected with nitrogen, sealed and pressurized at 1MPa, heated to 210°C, reacted for 10 hours, cooled down to 90°C, adjusted to pH 2 with 33% industrial hydrochloric acid, separated the water layer, maintained the temperature, and the organic phase Wash with water until neutral.

[0021] Add 300mL 98% concentrated sulfuric acid to the organic phase, stir, heat the reaction for 10h, add water, stir for 0.5h, stand still, divide the water phase, wash the organic phase with 500mL water to neutrality, decompose under reduced pressure, and use 150mL absolute ethanol Recrystallized to obtain 160 g of light yellow solid, namely: 2-isopropylthioxanthone with a content of 99.5%.

[0022] Melti...

Embodiment 2

[0024] Example 2: Preparation of 2-isopropylthioxanthone

[0025] Mix 130g (0.83mol) o-chlorobenzoic acid, 120g (0.79mol) 4-isopropylthiophenol, 68g (1.70mol) sodium hydroxide, 50mL of water, heat to 80℃ and stir for 0.5 hours, add mineral spirits 520mL, heated to reflux for dehydration, the resulting solution was protected with nitrogen, sealed and pressurized at 1MPa, heated to 200°C, and reacted for 12 hours. Cool down to 80°C, adjust the pH of the solution to 3 with 33% industrial hydrochloric acid, separate the water layer, maintain the temperature, and wash the organic phase with water to neutrality.

[0026] Add 300mL 98% concentrated sulfuric acid to the organic phase, stir, heat the reaction for 8h, add water, stir for 0.5h, stand still, divide the water phase, wash the organic phase with 500mL water to neutrality, de-solve under reduced pressure, use 150mL absolute ethanol Recrystallized to obtain 164g of light yellow solid, namely: 2-isopropylthioxanthone with a content...

Embodiment 3

[0027] Example 3: Preparation of 2-isopropylthioxanthone

[0028] Mix 130g (0.83mol) o-chlorobenzoic acid, 120g (0.79mol) 4-isopropylthiophenol, 68g (1.70mol) sodium hydroxide, 50mL water, heat to 80℃ and stir for 1 hour, add 520mL diesel oil , Heated to reflux for dehydration, the solution obtained for 1 hour was protected with nitrogen, sealed and pressurized at 1MPa, heated to 190°C, and reacted for 11 hours. Cool down to 90°C, adjust the pH of the solution to 2 with 33% industrial hydrochloric acid, separate the water layer, maintain the temperature, and wash the organic phase with water to neutrality.

[0029] Add 300mL 98% concentrated sulfuric acid to the organic phase, stir, heat the reaction for 10h, add water, stir for 0.5h, stand still, divide the water phase, wash the organic phase with 500mL water to neutrality, decompose under reduced pressure, and use 150mL absolute ethanol Recrystallized to obtain 157 g of light yellow solid, namely: 2-isopropylthioxanthone with a ...

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Abstract

The invention relates to a preparation method of 2-isopropyl thioxanthone and derivatives thereof, comprising the following steps of: carrying out condensation reaction on a derivative of o-chlorobenzoic acid (C7H5ClO2) and a derivative of 4-isopropyl thiophenol (C9H12S) in an organic solvent, and carrying out dehydration cyclization reaction on condensation products under the catalysis of concentrated sulfuric acid. The 2-isopropyl thioxanthone prepared by the invention can be used as a high-efficiency radical II-type photo initiator. The invention has easy operation, low cost, environmental protection and high purity; the purity of the product can reach more than 99 percent; the product can be commercially prepared and produced on a large scale to meet the current ever-increasing market demand.

Description

Technical field [0001] The invention relates to a preparation method of 2-isopropyl thioxanthone and its derivatives. Background technique [0002] 2-Isopropyl thioxanthone is a kind of high-efficiency free radical type II photoinitiator, suitable for unsaturated polyester, acrylic monomer and other light curing materials, and can be used for colorless or colored UV curing inks, decorative coatings, Adhesives, automotive metal parts coatings, optical fiber manufacturing, printed materials, etc. US4902826 reported the condensation reaction of o-chlorobenzoic acid, 4-isopropylthiophenol and lithium hydroxide in a tetralin solvent, and the condensation product was combined to obtain 2-isopropylthioxanthone. The disadvantage of this method is that the tetralin solvent is expensive, pollutes the environment, and the operation is complicated. US4094900 reported the condensation reaction of o-chlorobenzoic acid, 4-isopropylthiophenol, and sodium iodide in a 50% sodium hydroxide soluti...

Claims

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Application Information

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IPC IPC(8): C07D335/16
Inventor 赵国锋毛桂红吴正昆马红雨
Owner TIANJIN JIURI NEW MATERIALS CO LTD
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