Method of consistently producing diallylbisphenols

A diallyl bisphenol, bisphenol technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of easy handling, reduction of manufacturing processes, and prevention of loss

Active Publication Date: 2014-10-01
KONISHI CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Thus, in the production of diallyl bisphenols, in general, the allylation reaction is often carried out in a polar solvent, and the rearrangement reaction is often carried out in a non-polar solvent, and there is a need to switch solvents, Economic issues such as managing the operation of both solvents and installing separate storage containers

Method used

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  • Method of consistently producing diallylbisphenols

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] In an autoclave equipped with a stirrer, add 3,800 g of ethylene glycol monobutyl ether and 500 g of water to mix, and then add 1,000 g (4.0 moles) of 4,4'-dihydroxydiphenyl sulfone (hereinafter, bisphenol S ), 288 g (7.2 moles) of sodium hydroxide and 170 g (1.6 moles) of sodium carbonate. Next, 670 g (8.8 mol) of allyl chloride was added to form a closed state, and it was made to react by heating and stirring at 95 to 100° C. for 5 hours.

[0094] After the reaction was completed, the pressure was released, and the reaction liquid was further heated to distill off unreacted allyl chloride and the like. The distillate was liquid-separated into an upper layer and a lower layer. The upper layer (recovery solvent A) contained 165 g of ethylene glycol monobutyl ether.

[0095] After cooling the remaining reaction liquid in the still to 100° C., 1300 g of water was poured in, stirred to dissolve the inorganic salt by-product, separated, and the lower layer (water layer) w...

Embodiment 2

[0105] In the mixture of the total amount of recovered solvents A to C and 182 g of recovered solvent D in Example 1, add 145 g of ethylene glycol monobutyl ether, and add bisphenol S, sodium hydroxide and Sodium carbonate was reacted and post-treated in the same manner to obtain 1117 g of a refined product of bis(3-allyl-4-hydroxyphenyl)sulfone (yield to bisphenol S: 84.5%). The obtained purified bis(3-allyl-4-hydroxyphenyl)sulfone had an HPLC composition ratio (area percentage) of 97.1% and a melting point of 154 to 155°C.

Embodiment 3

[0107] In an autoclave equipped with a stirrer, 356 g of ethylene glycol monobutyl ether and 19 g of water were added and mixed, and 150 g (0.657 mol) of 2,2'-bis(4-hydroxyphenyl)propane (hereinafter, Bisphenol A), 53 g (1.325 mol) of sodium hydroxide and 14 g (0.132 mol) of sodium carbonate. Next, 121 g (1.581 mol) of allyl chloride was added to form an airtight state, and it was heated and stirred at 100 to 105° C. for 8 hours to make it react.

[0108] After completion of the reaction, allyl chloride was distilled off in the same manner as in Example 1, and a water solution was carried out. After neutralization, heat filtration was performed to obtain an ethylene glycol monobutyl ether solution of bisphenol A diallyl ether. The Na content of this reaction liquid was about 10 ppm. In addition, the HPLC composition ratio (area percentage) is 95.0% of 2,2-bis(4-allyloxyphenyl)propane, 0.2% of bisphenol A, 4-hydroxyphenyl-4'-allyloxybenzene Propane (hereinafter, bisphenol A m...

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Abstract

The purpose of the present invention is to provide a method of consistently producing high-quality diallylbisphenols with high yields from bisphenols. This method involves steps (1) through (3) below, and enables the consistent production of diallylbisphenols from bisphenols. (1) A step for reacting allyl halides and bisphenols or alkali metal salts thereof in a cellosolve solvent in the presence or absence of basic alkali metal salts, (2) a step for separating inorganic salt by-products from a reaction solution obtained in step (1), and (3) a step for heating and subjecting to a rearrangement reaction the reaction solution obtained in step (2).

Description

technical field [0001] The present invention relates to a method for producing diallyl bisphenols. Background technique [0002] Diallyl bisphenols are substances useful as color developers of thermosensitive recording materials, and various production methods have been tried. For example, the following production method of diallylated bisphenol S (3,3'-diallyl-4,4'-dihydroxydiphenyl sulfone) is well known: making bisphenol S (dihydroxydiphenyl sulfone ) reacts with allyl bromide to carry out allylation reaction, and after taking out the obtained bisphenol S diallyl ether as a powder, the diallyl ether is heated to carry out rearrangement (Claisen rearrangement) reaction (Patent Document 1). [0003] However, in this production method, after the allylation reaction, the obtained bisphenol S diallyl ether is crystallized and taken out as a powder, so about 6% of the yield of bisphenol S diallyl ether It is lost in the filtrate, and as a result, there is a problem that the ...

Claims

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Application Information

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IPC IPC(8): C07C37/18C07C39/21C07C315/04C07C317/22
CPCC07C37/18C07C315/04C07C39/21C07C317/22
Inventor 片山尚纪
Owner KONISHI CHEM IND
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