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Method for producing 4,4'-bicyclohexanedione monoketal

A technology of cyclohexyldione monoketal and cyclohexyldione, applied in the direction of organic chemistry and the like, can solve the problems of low yield, complicated chemical operation of separation, tedious operation and the like

Inactive Publication Date: 2011-10-12
HONSHU CHEM INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, according to this method, cumbersome operations are also required when the target monoketal is finally separated from the reaction mixture containing unreacted raw materials and monoketal and diketal, and the yield (40%) is low.
[0004] Like this, in the known method in the past, because unreacted raw material, by-product diketal, object product monoketal are mixed in the reaction mixed solution after the reaction finishes, so separation, refining object product monoketal need complicated chemical process. operation, so the yield is also reduced, so it needs to be improved as an industrial manufacturing method

Method used

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  • Method for producing 4,4'-bicyclohexanedione monoketal
  • Method for producing 4,4'-bicyclohexanedione monoketal
  • Method for producing 4,4'-bicyclohexanedione monoketal

Examples

Experimental program
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Effect test

Embodiment 1

[0058] Add 37.5g (0.193 mole) 4,4'-dicyclohexyl diketone, 225.0g n-pentane and 1.26g (9.64×10 -3 mol) 75% phosphoric acid. After replacing the inside of the flask with nitrogen, the temperature was raised to 37°C with stirring, and while the n-pentane was refluxed, the Dean-Stark separator was used for 1.0 hour dehydration pretreatment to obtain a slurry of 4,4'-bicyclohexyldione. Then at the same temperature, 1.5 g of monoethylene glycol ketal crystals were added thereto, and then, under the condition of n-pentane reflux, while removing the generated water through a Dean-Stark separator, 13.29 (0.214 mole ) Ethylene glycol. After dripping, at the same temperature and under the condition of n-pentane reflux, the generated water was removed by the Dean-Stark separator, and the subsequent stirring was carried out for 0.5 hours. As a result, with the precipitation of monoketal crystals, it became a reaction liquid The whiteness of the slurry increases significantly. Afterwards...

Embodiment 2

[0061] Add 37.5g (0.193 moles) 4,4'-bicyclohexyl diketone, 225.0g n-pentane and 0.76g (5.82×10 -3 mol) 75% phosphoric acid. After replacing the inside of the flask with nitrogen, the temperature was raised to 37° C. with stirring, and a dehydration pretreatment was performed for 1.0 hour while n-pentane was refluxed. Then, 13.29 g (0.214 mol) of ethylene glycol was added dropwise to the white slurry over 1 hour while removing generated water through a Dean-Stark separator at the same temperature under the condition of n-pentane reflux. 25 minutes after the start of the dropping, the reaction liquid became a slurry in which the whiteness of the reaction liquid was significantly increased along with the precipitation of crystals of the monoketal.

[0062] After dripping, at the same temperature and under the condition of reflux of n-pentane, the Dean-Stark separator removed the generated water and reacted for 40 minutes, then the internal temperature was reduced to 26-31° C., a...

Embodiment 3

[0065] Add 37.5g (0.193 mole) 4,4'-dicyclohexyl diketone, 225.0g n-pentane and 0.76g (5.82×10 -3 mol) 75% phosphoric acid. After replacing the inside of the flask with nitrogen, the temperature was raised to 37° C. with stirring, and while n-pentane was refluxed, a dehydration pretreatment was performed for 1.0 hour with a Dean-Stark separator. Then, 13.29 g (0.214 mol) of ethylene glycol was added dropwise to the white slurry over 1 hour while removing generated water through a Dean-Stark separator at the same temperature under the condition of n-pentane reflux. 25 minutes after the start of the dropping, the reaction liquid became a slurry in which the whiteness of the reaction liquid was significantly increased along with the precipitation of crystals of the monoketal.

[0066] After dripping, at the same temperature and under the condition of reflux of n-pentane, while removing the generated water through the Dean-Stark separator, react for 40 minutes, then lower the temp...

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Abstract

The present invention provides a method for producing a 4,4'-bicyclohexanedione monoketal represented by the formula (2) with high yield by a simple operation. In this method, 4,4'-bicyclohexanedione and a diol are reacted in the liquid phase in the presence of an acid catalyst while precipitating a 4,4'-bicyclohexanedione monoketal produced thereof.

Description

technical field [0001] The present invention relates to a method for producing 4,4'-bicyclohexyldiketone monoketals that can be effectively used as raw materials for pharmaceuticals, raw materials for industrial chemicals, or raw materials for liquid crystal compounds used in display devices. Background technique [0002] Conventionally, as a method for producing 4,4'-bicyclohexyl diketone monoketals, for example, a method is known in which 4, 4'-dicyclohexyl diketone and ethylene glycol class ketalization agent carry out dehydration condensation reaction, obtain the reaction mixture containing unreacted raw material and monoketal as reaction product, diketal simultaneously, then from this reaction mixture A method for obtaining the monoketal of the target product (Japanese Patent Laid-Open Publication No. 01-156935). However, according to this method, the process of isolating and purifying the monoketal of interest from the above-mentioned reaction mixture is complicated, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/72
CPCC07D317/72
Inventor 平岭正里见亨史
Owner HONSHU CHEM INDAL