New synthesis method for aromatic alpha-hydroxy ketone compounds

A synthetic method and technology of hydroxy ketones, applied in the field of ultraviolet light curing photoinitiators, can solve the problems of uncompetitiveness in industrial production, difficulties in equipment maintenance, and difficulties in the treatment of three wastes, and achieve low overall cost of raw materials, low equipment requirements, The effect of saving equipment cost

Inactive Publication Date: 2014-08-27
岳阳凯门科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] 1. The reaction is complex, and there are 4 main reactions;
[0011] 2. There are many by-products of the reaction, which need to be discharged externally
Under the increasingly stringent environmental protection conditions, there are great difficulties in the treatment of these three wastes
[0012] 3. A large amount of acid-resistant equipment is especially needed in the reaction process, and it is difficult to maintain the equipment
[0018] The above two methods all need to carry out an oxidation reaction on the added product, the equipment cost is high and the reaction has certain risks. Compared with the traditional synthetic route, it is not industrialized in terms of operating conditions or economic cost. Production competition, therefore, a large number of hydroxyketone compounds are still produced by the first method

Method used

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  • New synthesis method for aromatic alpha-hydroxy ketone compounds
  • New synthesis method for aromatic alpha-hydroxy ketone compounds
  • New synthesis method for aromatic alpha-hydroxy ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] 1.1 Add 106g benzaldehyde (1mol), 113g propanedithiol (1.05mol), 2L acetonitrile to a 5000ml four-neck flask, add catalyst Al2O3-SO3H (50g, 0.15mol H+), stir at room temperature until the reaction is complete (GC tracking ). After shrinking the reaction system to dryness, add dichloromethane to dissolve, filter, wash the catalyst with a small amount of dichloromethane, dry and activate it, and use it mechanically. The organic phase is sequentially filled with 2L of 10% sodium hydroxide solution, 2L of water, and 1L of saturated brine. After washing, drying with anhydrous sodium sulfate and shrinking to dryness, the product 2-phenyl-1,3-dithiane was obtained with a melting point of 68-70° C. and a yield of 98%.

[0061] 1.2 Add 0.5mol 2-phenyl-1,3-dithiane and 1.5L dried tetrahydrofuran to the bottle under nitrogen protection, stir, cool down to -30°C, add 218ml of n-butyl lithium solution (2.3M) dropwise, Keep warm at -30°C and stir for 1 hour, add 54 g of cyclohexanon...

Embodiment 2

[0064] 2.1 Add 106g benzaldehyde (1mol), 113g propanedithiol (1.05mol), 2L acetonitrile to a 5000ml bottle, add catalyst Al2O3-SO3H (50g, 0.15mol H+), stir at room temperature until the reaction is complete (GC tracking). After shrinking the reaction system to dryness, add dichloromethane to dissolve, filter, wash the catalyst with a small amount of dichloromethane, dry and activate it, and use it mechanically. The organic phase is washed successively with 2L of 10% sodium hydroxide solution, 2L of water and 1L of saturated brine , dried over anhydrous sodium sulfate, and shrunk to give the product 2-phenyl-1, 3-dithiane. The melting point is 68-70°C, and the yield is 98%.

[0065] 2.2 Add 0.5mol 2-phenyl-1,3-dithiane and 1.5L dried tetrahydrofuran to the bottle under nitrogen protection, stir, cool down to -30°C, add 218ml of n-butyl lithium solution (2.3M) dropwise, Keep warm at -30°C and stir for 1 hour, add 32g of acetone to the system, after the addition is complete, the...

Embodiment 3

[0068] 3.1 Add 106g benzaldehyde (1mol), 113g propanedithiol (1.05mol), 2L acetonitrile to a 5000ml bottle, add catalyst Al2O3-SO3H (50g, 0.15mol H+), stir at room temperature until the reaction is complete (GC tracking). After shrinking the reaction system to dryness, add dichloromethane to dissolve, filter, wash the catalyst with a small amount of dichloromethane, dry and activate it, and use it mechanically. The organic phase is washed successively with 2L of 10% sodium hydroxide solution, 2L of water and 1L of saturated brine , dried over anhydrous sodium sulfate, and shrunk to give the product 2-phenyl-1, 3-dithiane. The melting point is 68-70°C, and the yield is 98%.

[0069] 3.2 Add 0.5mol 2-phenyl-1,3-dithiane and 1.5L dried tetrahydrofuran to the bottle under nitrogen protection, stir, cool down to -30°C, add 218ml of n-butyl lithium solution (2.3M) dropwise, Keep warm at -30°C and stir for 1h, add 46g of cyclopentanone to the system, after the addition is complete, ...

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Abstract

The invention discloses a novel synthesis method for aromatic alpha-hydroxy ketone compounds. The method comprises three steps of reactions of condensation protection, addition and deprotection on aromatic aldehyde which is used as a raw material, i.e., firstly, the aromatic aldehyde reacts with mercaptan to obtain substituted thiophene alkane which reacts with butyl lithium to obtain lithium salt, the lithium salt is subjected to an addition reaction with ketone to obtain hydroxy compounds, and finally, the hydroxy compounds are deprotected under heavy metal catalysis to obtain target products of the aromatic alpha-hydroxy ketone compounds. When the method provided by the invention is compared with a traditional method, the catalyst can be repeatedly used many times, the emission of various wastes is greatly reduced, an oxidation step is omitted, and reaction risks are reduced. The aromatic alpha-hydroxy ketone compounds prepared through reactions can be used as ultraviolet curing photoinitiators for massive use.

Description

technical field [0001] The invention relates to a new synthesis method of an aromatic α-hydroxy ketone compound, which can be used in the field of ultraviolet curing photoinitiators. Background technique [0002] Aromatic α-hydroxyketone compounds are a very important class of UV-curable photoinitiators, and their representative products mainly have the following two structures: [0003] Ciba's two products: [0004] [0005] Traditionally, such compounds have been synthesized as follows: [0006] 1. R 1 CHCOOH+PCl 3 →R 1 CHCOCl+H 3 PO 3 [0007] [0008] The product 1173 was obtained when isobutyric acid was used as the starting material according to the above procedure, and 184 was obtained when cyclohexanecarboxylic acid was used as the starting material. US Patent No. 4,861,916 comprehensively summarizes the synthesis methods of the above-mentioned aromatic α-hydroxy ketone compounds. [0009] There is following major shortcoming in the synthetic route of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/83C07C45/56C07C49/82
CPCC07C45/567C07C2601/08C07C2601/14C07D339/08C07C49/83C07C49/82
Inventor 张正波卓耀文杨朝辉
Owner 岳阳凯门科技有限公司
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