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Preparation method of 2,4-diethylthioxanthone

A technology of diethylsulfur and diethylthiophenol, which is applied in the field of compound preparation, can solve the problems of increased waste water discharge, complex preparation process, and difficult storage, and achieves reduced usage, cheap and easy-to-obtain raw materials, and post-production Handle with convenient effects

Inactive Publication Date: 2018-05-25
TIANJIN RUILING CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, only the patent CN 102250060 reports the method for preparing 2,4-diethylthioxanthone with m-diethylbenzene and dithiosalicylic acid as raw materials and sulfuric acid as a solvent. The main raw material used in this method is dithioxanthone The preparation process of salicylic acid is complicated, the cost is high, and its chemical properties are active, it is easy to react with water vapor and oxygen in the air, and it is not easy to preserve; A large amount of waste acid solution; the reaction cycle is as long as 12-20 hours, and the post-treatment requires extraction operations, which further increases the amount of wastewater discharge
In addition, the patent CN101817812 reports a method for the industrial production of a similar compound 2-isopropylthioxanthone. This method uses high temperature and high pressure reaction, the conditions are harsh, and it is not suitable for 2,4-diethylthioxanthone preparation of

Method used

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  • Preparation method of 2,4-diethylthioxanthone
  • Preparation method of 2,4-diethylthioxanthone
  • Preparation method of 2,4-diethylthioxanthone

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Add 33.2g (0.20mol) of 2,4-diethylthiophenol, 60mL of N,N-dimethylformamide and 14.16g (0.24mol) of potassium hydroxide into a 500mL four-necked flask, heat to make 2, Completely convert 4-diethylthiophenol into 2,4-diethylthiophenate potassium, then add 33.0g (0.24mol) o-chlorobenzonitrile, heat up to 130°C under stirring, keep warm for reaction, and monitor the reaction by TLC or gas phase After the reaction, the solvent was distilled off under reduced pressure to obtain crude 2-(2,4-diethylthiophenol)benzonitrile. Add the crude product to 70mL of toluene, cool down to below 5°C in an ice bath, slowly add 25mL of 95% sulfuric acid dropwise, after dropping, heat slowly, raise the temperature to 90°C and keep it warm for reaction, monitor the reaction by TLC or gas phase, after the reaction, cool down to room temperature, Add water to the reaction system, stir for 1 hour, let stand, separate the water phase, wash the organic phase with water until neutral, and recover t...

Embodiment 2

[0032] Add 33.2g (0.20mol) of 2,4-diethylthiophenol, 60mL of N,N-diethylformamide and 14.96g (0.22mol) of sodium ethoxide into a 500mL four-necked flask, heat to make 2,4 -Diethylthiophenol is completely converted into 2,4-diethylthiophenate sodium, then add 33.0g (0.24mol) o-chlorobenzonitrile, heat up to 135°C under stirring, keep warm for reaction, TLC or gas phase monitoring reaction, After the reaction, the solvent was distilled off under reduced pressure to obtain crude 2-(2,4-diethylthiophenol)benzonitrile. Add the crude product to 70mL of toluene, cool down to below 5°C in an ice bath, slowly add 30mL of 95% sulfuric acid dropwise, after dropping, heat slowly, raise the temperature to 105°C and keep it warm for reaction, monitor the reaction by TLC or gas phase, after the reaction, cool down to room temperature, Add water to the reaction system, stir for 0.5 hours, let stand, separate the water phase, wash the organic phase with water until neutral, and recover toluene...

Embodiment 3

[0034]Add 33.2g (0.20mol) of 2,4-diethylthiophenol, 30mL of dimethyl sulfoxide, 30mL of m-diethylbenzene and 9.6g (0.24mol) of sodium hydroxide into a 500mL four-neck flask, heat Completely convert 2,4-diethylthiophenol into sodium 2,4-diethylthiophenate, then add 33.0g (0.24mol) o-chlorobenzonitrile, heat up to 135°C under stirring, keep warm for reaction, TLC or The reaction was monitored by gas phase. After the reaction, the solvent was distilled off under reduced pressure to obtain crude 2-(2,4-diethylthiophenol)benzonitrile. Add the crude product to 70mL of toluene, cool down to below 5°C in an ice bath, slowly add 30mL of 95% sulfuric acid dropwise, after dropping, heat slowly, raise the temperature to 100°C and keep it warm for reaction, monitor the reaction by TLC or gas phase, after the reaction, cool down to room temperature, Add water to the reaction system, stir for 0.8 hours, let stand, separate the water phase, wash the organic phase with water until neutral, and...

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Abstract

The invention provides a preparation method of 2,4-diethylthioxanthone. By optimally using a solvent which has good solubility to a substrate, the reaction of 2,4-diethylbenzene sulfur phenolate and phthalonitrile is accelerated under the condition of homogeneous phase, and the reaction period is shortened by 70 percent or above when being compared with that of a traditional process; the cyclization reaction has mild conditions, the use amount of concentrated sulfuric acid in the reaction is reduced by about 80 percent compared with that of a traditional process, and the discharge of waste acid and waste water is greatly compressed, so that the aims of energy saving and emission reduction are achieved. The two-stage reaction can be accurately controlled by thin-layer chromatography, the operation is simple and convenient, the post process is convenient, and the total yield reaches 85 percent or above; the preparation method of the 2,4-diethylthioxanthone is suitable for industrializedproduction.

Description

technical field [0001] The invention relates to a preparation method of a compound, especially a preparation method of 2,4-diethylthioxanthone. Background technique [0002] 2,4-Diethylthioxanthone (DETX) is a high-efficiency free radical type II photoinitiator, suitable for photocuring systems composed of various oligomers and reactive diluents, etc., in UV wood coatings, It is widely used in offset printing ink, photoresist, adhesive, automotive metal coating and other fields. At present, only the patent CN 102250060 reports the method for preparing 2,4-diethylthioxanthone with m-diethylbenzene and dithiosalicylic acid as raw materials and sulfuric acid as a solvent. The main raw material used in this method is dithioxanthone The preparation process of salicylic acid is complicated, the cost is high, and its chemical properties are active, it is easy to react with water vapor and oxygen in the air, and it is not easy to preserve; A large amount of waste acid solution; th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/16
CPCC07D335/16
Inventor 卢博为胡新龙谢志强
Owner TIANJIN RUILING CHEM CO LTD
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