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Method for producing trisphenols and monoester derivatives thereof, and 4-acylaralkylphenol derivatives

一种酰基芳烷基苯酚、制造方法的技术，应用在有机化合物的制备、羧酸酯制备、碳基化合物制备等方向，能够解决保存稳定性不佳、价格高、合成收率低等问题

Active Publication Date: 2012-04-25
HONSHU CHEM INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, since the known raw material isopropenyl acetophenone has an active olefin group, storage stability is not good, there is a problem that it is easy to polymerize and form a polymer due to the mixing of impurities such as heat or acid, and the price is high and The problem of low synthesis yield

Method used

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  • Method for producing trisphenols and monoester derivatives thereof, and 4-acylaralkylphenol derivatives
  • Method for producing trisphenols and monoester derivatives thereof, and 4-acylaralkylphenol derivatives
  • Method for producing trisphenols and monoester derivatives thereof, and 4-acylaralkylphenol derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0183] Synthesis of 4-(1-(4-acetoxyphenyl)-1-methylethyl)acetophenone (Step A1b)

[0184] 70.5 g (0.542 mol) of aluminum chloride and 105.8 g of chloroform (1.5 times the weight of aluminum chloride) were introduced into a 500 ml four-necked flask equipped with a dropping funnel, a cooling tube, and a stirrer, while replacing the inside of the system with nitrogen. Cool to 5 °C. After cooling, 42.3 g (0.542 mol) of acetyl chloride was dropped over 1 hour through the dropping funnel to form a complex. The complex will not dissolve in chloroform at 5°C, and the system will become a slurry solution.

[0185] After the complex was formed, in this solution, while maintaining the temperature in the flask at 5°C, 50.0 g (0.236 mol) of p-cumylphenol dissolved in 75 g of chloroform (relative to p-cumyl phenol) was added dropwise over 3 hours. 1.5 times the weight of cumyl phenol), after the dropwise addition was completed, it was reacted at 20°C for 2 hours.

[0186] After completio...

Embodiment 2

[0194] Synthesis of 4-(1-(4-hydroxyphenyl)-1-methylethyl)acetophenone (step C1)

[0195] 20.1 g of crystals obtained in Example 1 were dissolved in 20 g of toluene, 24.0 g of 16% aqueous sodium hydroxide solution and 2 g of methanol were added, and hydrolysis reaction was carried out at 50° C. for 2.5 hours. After the reaction, it was neutralized with 75% phosphoric acid, and then the water layer was removed.

[0196] From the obtained oil layer, toluene was distilled off at 60° C. to 10 kPa, and 18.0 g of an orange solid having a purity of 99.9% as measured by HPLC was obtained.

[0197] This solid was analyzed by NMR and mass spectrometry, and it was confirmed to be 4-(1-(4-hydroxyphenyl)-1-methylethyl)acetophenone.

[0198] Also, the yield relative to p-cumylphenol was 60.0%.

[0199] 1 H-NMR (400MHz, CDCl 3 , standard substance: tetramethylsilane)

[0200] 7.86 (aromatic H, 2H, doublet, J=8.78Hz, b in the figure), 7.32 (aromatic H, 2H, doublet, J=8.78Hz, c in the figu...

Embodiment 3

[0203] Synthesis of 1-(α,α-bis(4-hydroxyphenyl)ethyl)-4-(α-methyl-α-(4-hydroxyphenyl)ethyl)benzene (Step B1)

[0204] Into a 300 ml 4-necked flask equipped with a dropping funnel, a cooling tube, and a stirrer, 55.6 g of phenol, 1.7 g of toluene (3 wt. mol%), while replacing the inside of the system with nitrogen, the temperature was raised to 40°C.

[0205] After replacing with nitrogen gas, the inside of the system was replaced with hydrogen chloride gas. While maintaining the internal temperature of the flask at 40 to 45° C. while continuously supplying hydrogen chloride gas, the 4-[1-methyl-1-(4-hydroxyphenyl)ethane obtained in Example 2 was added dropwise over 3 hours. Base] Acetophenone 24.6g (0.096mol) dissolved in phenol 24.6g solution.

[0206] After completion of the dropwise addition, the mixture was stirred at 40° C. for 18 hours to continue the reaction. After completion of the reaction, 35.7 g of toluene was added to the reaction-completed mixture, then a 16% ...

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Abstract

Provided are a method for industrially easily producing trisphenols, which are useful as starting materials for polymer compounds such as epoxy resins and polycarbonate resins and starting materials or additives for photoresists, at a high purity and high yield, and 4-acylaralkylphenol derivatives. Specifically, provided are: a method for producing a trisphenol represented by general formula (1) [wherein R1 to R4 independently represent a hydrogen atom, an alkyl group, an alkoxyl group, an aromatic hydrocarbon group, a halogen atom, an acyloxy group or a hydroxyl group; R5 and R6 independently represent a hydrogen atom or an alkyl group; R7 represents a hydrogen atom or an alkyl group; R0 represents an alkyl group, an alkoxyl group or a halogen atom; n represents 0 or an integer of 1 to 4, provided that in the case where n is 2 or greater, R0's may be either the same or different; and R9 to R11 independently represent a hydrogen atom, an alkyl group, an alkoxyl group, an aromatic hydrocarbon group, a halogen atom or a hydroxyl group], which comprises using, as a starting material, a 4-aralkylphenol derivative represented by general formula (2) [wherein R1 to R4, R5 and R6, R0 and n are each as defined in general formula (1); and X represents a hydrogen atom or a leaving group which can be substituted by a hydrogen atom, provided that in the case where n is 1 or greater, R0 does not attach to the 4-position of the phenyl group]; and a 4-acylaralkylphenol derivative.

Description

technical field [0001] The present invention relates to industrially easy, high-yield, high-purity production of trisphenols used as raw materials for high molecular compounds such as epoxy resins and polycarbonate resins, or as raw materials or additives for photoresists At the same time, it relates to novel 4-acyl aralkylphenol derivatives with bisphenyl as the molecular skeleton, wherein one benzene ring has an acyl group, and the other benzene ring has a hydroxyl or acyloxy group. These compounds are useful as various reactive raw materials having improvement effects such as heat resistance, and are particularly useful as intermediate raw materials for reacting with phenols to generate trisphenols, which are used as polycarbonate Raw materials for polymer compounds such as ester resins or raw materials for photoresists. Background technique [0002] As far as trisphenols are concerned, especially trisphenols other than the trisphenol methane type, 1-[1,1-bis(4-hydroxyph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/20C07C39/15C07C45/65C07C49/83C07C67/29C07C69/157
CPCC07C69/157C07C49/83C07C67/08C07C37/0555C07C69/017C07C67/14C07C45/455C07C37/20C07C45/673C07C49/82C07C67/29C07C69/24C07C39/16
Inventor 尾尻明彦辻上隆章丹波孝一
Owner HONSHU CHEM INDAL
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