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Method for producing 4,4''-dihydroxy-m-terphenyls

A technology of m-terphenyl and its manufacturing method, which is applied in 4 fields and can solve problems such as difficult industrial implementation, high manufacturing cost, and no record

Active Publication Date: 2015-02-25
HONSHU CHEM INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, according to these methods, while using special expensive raw materials such as organometallic compounds, Grignard reaction and the like are also required, so the production cost is very high, and it is difficult to implement industrially.
[0005] In addition, on the other hand, although a method for producing dihydroxy-p-terphenyls from trisphenols is known (Patent Document 4), the method for producing trisphenols from unsaturated ketones, the production of dihydroxy-m-terphenyls method is not yet documented

Method used

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  • Method for producing 4,4''-dihydroxy-m-terphenyls
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  • Method for producing 4,4''-dihydroxy-m-terphenyls

Examples

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Embodiment 1

[0174] [Synthesis of 4,4"-dihydroxy-m-terphenyl]

[0175] Step (A): (Synthesis of 1,1,3-tris(4-hydroxyphenyl)cyclohexane)

[0176] Put 1412g of phenol, 78.2g of 35% hydrochloric acid, 15.2g of dodecyl mercaptan, and 144g of methanol into a four-necked flask with a capacity of 3 liters, and keep the liquid temperature at 30-32°C under a nitrogen atmosphere, while adding 144g of 2- Cyclohexen-1-one was used for 10 hours, and after the dropwise addition was terminated, the mixture was stirred at 30° C. for 46 hours. After the reaction was terminated, an aqueous sodium hydroxide solution was added for neutralization, and then the temperature was raised to distill off methanol. Then, water and methyl isobutyl ketone were added to the oil layer obtained by separating and removing the water layer, stirred and washed with water, and the water layer was separated and removed. Phenol which had not reacted with methyl isobutyl ketone was distilled off from the obtained oil layer under ...

Embodiment 2

[0207] [Synthesis of 4,4"-dihydroxy-m-terphenyl]

[0208] 90g of 1,1,3-tri(4-hydroxyphenyl)cyclohexane and 45g of tetraethylene glycol, 45g of methyl alcohol, 6.3g of 16% sodium hydroxide aqueous solution obtained in the operation (A) of embodiment 1 were dropped into four In the mouth bottle, the pressure was reduced to 10kPa while stirring, and at the same time, the temperature of the liquid was raised to 170°C, and the phenol generated at the same temperature was further distilled off while stirring for 9 hours to carry out the reaction. After completion of the reaction, after cooling, acetic acid was added to neutralize, and then water and methyl isobutyl ketone were added to stir and wash with water [process (B)].

[0209] After separating the water layer, 1,3-bis(4-hydroxyphenyl)-1-cyclohexene and 1,5-bis(4-hydroxyphenyl)-1-cyclohexene in the oil layer were separated by concentration etc. Adjust the concentration of the mixture to 17%. 79.6 g of this solution, 14.8 g o...

Embodiment 3

[0212] [Synthesis of 3,3"-dimethyl-4,4"-dihydroxy-m-terphenyl]

[0213] Step (A): (Synthesis of 1,1,3-tris(3-methyl-4-hydroxyphenyl)cyclohexane)

[0214]Put 1513.4g of o-cresol, 73g of 35% hydrochloric acid, 14.2g of dodecyl mercaptan, and 134.4g of methanol into a four-necked flask with a capacity of 3 liters. 134.5 g of 2-cyclohexen-1-one was added for 3.5 hours, and after the dropwise addition was terminated, the mixture was stirred at 30 to 32° C. for 22 hours. After the reaction was terminated, an aqueous sodium hydroxide solution was added for neutralization, and then the temperature was raised to distill off methanol. Thereafter, methyl isobutyl ketone and water were added to the oil layer obtained by separating and removing the water layer, stirred and washed with water, and the water layer was separated and removed. From the obtained oil layer, o-cresol which had not reacted with methyl isobutyl ketone was distilled off under reduced pressure. After the residue was...

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Abstract

The invention provides a method for producing 4,4''-dihydroxy-m-terphenyls using 2-cyclohexene-1-ones or 3-hydroxycyclohexane-1-ones, and phenols as raw materials.

Description

technical field [0001] The present invention relates to a production method of 4,4"-dihydroxy-m-terphenyls. More specifically, the present invention relates to a production method capable of obtaining 4,4"-dihydroxy-m-terphenyls in the following manner: , using 2-cyclohexene-1-ketones or 3-hydroxycyclohexan-1-ketones and phenols as raw materials, successively go through three steps of step (A), step (B) and step (C) Or, through step (D) and step (C) sequentially, 4,4"- Dihydroxy-terphenyls. Background technique [0002] Conventionally, as a method for producing 4,4"-dihydroxy-m-terphenyls, for example, 1,1,3,3-tetrakis(4- Hydroxyphenyl)-cyclohexane undergoes decomposition and dehydrogenation reaction to synthesize 4,4 "-dihydroxy-m-terphenyls (patent document 1). However, in this method, the yield of the raw material tetraphenol is extremely low or cannot be synthesized at all. [0003] In addition, a method of deprotecting 2-(4-bromophenoxy)tetrahydro-2H-pyran and 1,3-d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/06C07C37/50C07C39/15C07B61/00
CPCC07C37/06C07C37/50C07C37/20C07C37/52C07C2601/14C07C2601/16C07C39/15C07C39/23C07C39/17
Inventor 芦田一仁桥本祐树山本智也路绪旺
Owner HONSHU CHEM INDAL
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