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Method for producing hydrogenated biphenol

a hydrogenated biphenol and high-purity technology, applied in the field of high-purity hydrogenated biphenol production, can solve the problems of increased cost and complex operation of the method, and achieve the effects of high purity, efficient production and simple operation

Inactive Publication Date: 2015-10-20
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013]According to the method for producing hydrogenated biphenol according to the present invention, hydrogenated biphenol having a very high purity can be efficiently produced by a simple operation. Consequently, the method for producing hydrogenated biphenol according to the present invention can be preferably used when producing high-purity hydrogenated biphenol on an industrial scale.

Problems solved by technology

Although the yield is sufficient, this method suffers from the drawback of complex operation.
However, in this method, since a glycol monoalkyl ether having seven or less carbon atoms, which is a high-boiling point compound, is used as the solvent, the reaction system has to be put under reduced pressure and high temperature for the distillation, and thus as an industrial production method there is a problem of increased costs due to the large amount of energy required and the need to prepare high-performance equipment.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

production example 1

[0049]A 300-mL autoclave equipped with a stirring device was charged with 20 g of 4,4′-biphenol, 1 g of Raney nickel, and 80 g of 2-propanol, and a hydrogenation reaction was carried out for 2 hours at a hydrogen pressure of 6 MPa and a reaction temperature of 150° C. 2-Propanol was added to the obtained reaction solution until the crystals had completely dissolved. Then, filtration was carried out to obtain a reaction product solution from which the catalyst had been removed.

[0050]Then, 21.4 g of crude 4,4′-bicyclohexanol (A) (purity: 96.7%) was obtained by concentrating and drying this reaction product solution.

example 1

[0051]A 100-mL four-necked glass flask equipped with a stirring device and a thermometer was charged with 5.0 g of the crude 4,4′-bicyclohexanol (A) obtained in Production Example 1 and 95 g of toluene, and the resultant mixture was stirred and washed for 4 hours at 95° C. The mixture was then cooled to room temperature (25° C.), and the crystals were filtered and rinsed with toluene. The crystals were then vacuum dried to remove the toluene, whereby 4.75 g of 4,4′-bicyclohexanol (recovery ratio: 95%, purity: 99.6%) was obtained.

example 2

[0056]A 300-mL four-necked glass flask equipped with a stirring device and a thermometer was charged with 10.4 g of crude 4,4′-bicyclohexanol (B) (purity: 98.1%) and 190 g of toluene, and the resultant mixture was stirred and washed for 4 hours at 95° C. The mixture was then cooled to room temperature (25° C.), and the crystals were filtered and rinsed with toluene. The crystals were then vacuum dried to remove the toluene, whereby 4,4′-bicyclohexanol (recover ratio: 96%, purity: 99.8%) was obtained.

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Abstract

Provided is a method for efficiently producing high-purity hydrogenated biphenol based on a simple method that can be industrially utilized using easily-available biphenol as a starting material. The method for producing hydrogenated biphenol according to the present invention is a method for producing hydrogenated biphenol by hydrogenating biphenol represented by the following formula (1):to obtain hydrogenated biphenol represented by the following formula (2):the method including: a reaction step of hydrogenating the biphenol represented by formula (1); and a purification step of washing or crystallizing a reaction product obtained from the reaction step using an aromatic hydrocarbon.

Description

TECHNICAL FIELD[0001]The present invention relates to a method for producing high-purity hydrogenated biphenol that is useful as a fine chemical intermediate for pharmaceuticals, agricultural chemicals, electronic materials, and the like. The present application claims priority on the basis of Japanese Patent Application No. 2012-088136 filed in Japan on Apr. 9, 2012, the contents of which are incorporated herein by reference.BACKGROUND ART[0002]Conventionally, several methods have been known as methods for producing hydrogenated biphenol. In PTL 1, a portion of 4,4′-bicyclohexanol, which is the target hydrogenated bisphenol, is obtained using isopropanol as a solvent by hydrogenating bisphenol in the presence of 5% by weight of a Pd—C catalyst, filtering the reaction mixture, and removing the isopropanol from the filtrate by distillation under reduced pressure. At the same time, 4,4′-bicyclohexanol is also obtained by dissolving the crystals obtained during filtering in 500 mL of t...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C29/20C07C29/60C07C29/78C07C1/24
CPCC07C29/20C07C1/24C07C29/60C07C29/78C07C2101/14C07C2101/16C07C2527/055
Inventor OHNO, MITSURUHASHIZUME, TOMOHIRO
Owner DAICEL CHEM IND LTD