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Synthetic method of 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene

A hydroxyethylsulfone-based, synthetic method technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of increasing the difficulty of post-processing, reducing the quality of recovered products, and long reaction time, avoiding high temperature The effect of concentration operation, reduction of raw material input cost, and simplification of post-processing operations

Inactive Publication Date: 2014-02-05
ZHEJIANG RUNTU INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] But, when adopting the method of above-mentioned patent document, there is following technical problem: when carrying out reaction at less than or equal to 80 ℃, even if the alkali that adds is greatly excessive, reaction can not react completely all the time, needs to be heated up to more than 90 ℃; During the reaction, if there is a slight excess of strong base, the pH value will easily exceed the required range, thereby forming a black oily by-product. If the amount of strong base is insufficient, the raw materials cannot be completely reacted. , will make the local pH value of the material too high, and will also quickly generate a large amount of black oil, which increases the difficulty of post-processing, reduces the quality of recycled products, and is not conducive to the recycling of products
However, the use of a single weak base salt and "double sulfone" reaction will affect the reaction rate on the one hand, and the reaction time will be longer. , resulting in unnecessary waste

Method used

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  • Synthetic method of 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene
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  • Synthetic method of 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene

Examples

Experimental program
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Effect test

Embodiment 1

[0025]In a 2000mL flask, add 360g of sodium 3-nitrobenzenesulfinate, 1000mL of water, dropwise add 160g of ethylene oxide, neutralize with dilute sulfuric acid throughout the dropping process, control the pH range of 7.0-7.5, at 60°C Reacted for 10 hours. After the reaction was completed, it was vacuum filtered through a Buchner funnel and washed with water to obtain 395 g of filter cake 3-(β-hydroxyethylsulfone)-nitrobenzene, which was extracted with methanol to obtain "bissulfone" (2-bis( 3'-nitrophenylsulfone) ethane) 38g, prepare 1000g of 2-bis(3'-nitrophenylsulfone)ethane according to the same method, for the following hydrolysis reaction.

Embodiment 2

[0027] In a 1000mL flask, add 400g of clear water, 13g of liquid caustic soda with a concentration of 30% by mass, 1.5g of sodium carbonate, 44.4g of 2-bis(3′-nitrophenylsulfone)ethane, and the pH value of the system is greater than 14, stir and heat At 70°C, heat-retain for 1 hour. At this time, the bissulfone has been partially hydrolyzed. The pH value of the reaction system measured at the end of the heat-preservation is 9.6. Add 2 g of sodium carbonate to adjust the pH value to 11. Continue to heat up to 98°C. After 3 hours of heat preservation The bissulfone is completely hydrolyzed, there is no oil layer at the bottom of the flask, the reaction liquid is bright yellow, and there is basically no white insoluble matter. Cool down to 80°C, add 0.3g activated carbon for decolorization, stir for 0.5h, filter, stir the filtrate and cool down to 20°C, filter, solid Dry to obtain 21.5g of 3-(β-hydroxyethylsulfonyl)-nitrobenzene, the yield is 83.8%, the purity is 98.7%, the filtra...

Embodiment 3

[0029] In a 1000mL three-necked flask, add 400mL of the mother liquor of Example 2, add 12g of liquid caustic soda and 2g of soda ash with a mass percentage concentration of 30%, and 44.4g of 2-bis(3'-nitrophenylsulfone)ethane, the first Section heat preservation reaction temperature is 75 DEG C, other adopts the same method as embodiment 2 to operate, the pH value is 10.9 after the first hour heat preservation finishes, continue to heat up to 100 DEG C, heat preservation 3h, phenomenon is consistent with embodiment 1, there is no Black oil layer. After a series of operations such as cooling, decolorization and filtration, 20.8 g of dry product 3-(β-hydroxyethylsulfone group)-nitrobenzene was obtained, the purity was 98.3%, and the yield was 81.1%; the filtrate was 422 g, and the mass content of sodium sulfinate was measured as 9.5%, namely 40.1g, the filtrate continues to apply mechanically to the next batch of hydrolysis. After applying mechanically to the third batch, the ...

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Abstract

The invention discloses a synthetic method of 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene, comprising the following steps: carrying out an addition reaction between sodium 3-nitrobenzenesulfinate and oxirane to obtain 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene and a by-product 1,2-bis(3'-nitrobenzolsulfonyl)ethane; adding the by-product into an alkali-mixed solution to react at the temperature of being less than or equal to 80 DEG C until pH value of the system is below 11, heating a liquid of the system to 90 DEG C or over to carry out an reaction so as to obtain a product a mixed liquor of 3-(beta-hydroxyethyl sulfonyl)-nitrobenzene and sodium 3-nitrobenzenesulfinate; and returning the mixed liquor to a hydrolysis step or addition step for recycling use. With the combination of the alkali-mixed system and two stages of heating reaction, complete hydrolysis of 1,2-bis(3'-nitrobenzolsulfonyl)ethane is guaranteed, side reaction is avoided, product quality is raised, total usage amount of alkali is minimized, postprocessing operation is simplified, and preparation cost is reduced.

Description

technical field [0001] The invention belongs to the field of preparation of dye intermediates, in particular to a preparation method of vinylsulfone-type reactive dye intermediate 3-(β-hydroxyethylsulfone)-nitrobenzene. Background technique [0002] Vinyl sulfone reactive dyes (i.e. domestically produced KN reactive dyes) have many varieties and complete chromatograms. They are the second largest type of reactive dyes after chlorotriazine reactive dyes. They are widely used in the dye industry. 3- (β-hydroxyethylsulfone)-nitrobenzene is one of the main raw materials for the synthesis of vinylsulfone-type reactive dyes, and 3-(β-hydroxyethylsulfone)-nitrobenzene is obtained through sodium 3-nitrobenzenesulfinate It is prepared by addition reaction with ethylene oxide under certain conditions. During the preparation process, some intermediate product 3-vinylsulfone-nitrobenzene (compound shown in formula (I)) and unreacted raw material 3- Sodium nitrobenzenesulfinate (compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/22C07C315/00C07C315/04
Inventor 何江伟赵国生阮海兴高立江
Owner ZHEJIANG RUNTU INST
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