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Process for producing trimellitic anhydride phenyl ester

A technology of trimellitic anhydride phenyl ester and trimellitic anhydride benzene, which is applied in the field of trimellitic anhydride phenyl esters, can solve the problems of low reaction speed, expensive catalyst, insufficient reaction selectivity, etc., and achieve increased yield, increased reaction selectivity, and selectivity. Excellent rate of effect

Inactive Publication Date: 2013-02-27
HONSHU CHEM INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] For example, a method of transesterifying phenolic acetate and trimellitic anhydride in the presence of a phase transfer catalyst is known (Patent Document 2), but the reaction selectivity is not sufficient
[0006] In addition, a method of transesterifying phenolic acetate and trimellitic anhydride in the presence of a silica-alumina catalyst or an inorganic compound catalyst composed of an alkali metal or an alkaline earth metal is known (Patent Document 3), but The reaction selectivity of inorganic compounds composed of alkali metals and alkaline earth metals is insufficient, and the reaction selectivity of silica-alumina catalysts is also insufficient, and the catalyst itself is expensive
[0007] In addition, there is known a method of performing a transesterification reaction of a lower alkanoic acid ester of an aromatic diol and trimellitic anhydride in a solvent such as triethylbiphenyl or diphenyl ether without a catalyst (Patent Document 4), but The reaction rate is low and the reaction selectivity is not sufficient
[0008] Furthermore, there is known a method of transesterifying phenol acetates and trimellitic anhydride in the presence of a sodium acetate catalyst without using a solvent (Patent Document 5), but the reaction selectivity is not sufficient

Method used

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  • Process for producing trimellitic anhydride phenyl ester
  • Process for producing trimellitic anhydride phenyl ester
  • Process for producing trimellitic anhydride phenyl ester

Examples

Experimental program
Comparison scheme
Effect test

reference example 1）

[0102] Add 675.0g (6.6 moles) of acetic anhydride and 342.0g (1.5 moles) of 2,2-bis(4-hydroxyphenyl)propane into a 3L 4-neck flask equipped with a thermometer, a reflux device, and a stirring blade. After heating up to 130° C. with stirring, the reaction was further carried out at the same temperature for 2.5 hours while stirring.

[0103] After the reaction was terminated, 703 g of toluene was added and cooled, then water was added, stirred, and washed with water.

[0104] Thereafter, the water layer was separated and removed, and toluene was distilled and removed from the obtained oil layer, and 937 g of heptane was added, crystallized and filtered to obtain 2,2-bis(4 -Acetoxyphenyl) propane (hereinafter referred to as BPA-DA) crystals.

Embodiment 1）

[0106] After the 300ml four-necked flask equipped with stirrer, thermometer, Dean-Stark device, and reflux condenser was replaced with nitrogen, 25.0g (0.080 moles) of BPA-DA, 46.2g ( 0.241 mol) of trimellitic anhydride, 0.25 g (relative to BPA-DA: 4.7 mol %) of lithium acetate, and 54.5 g of diphenyl ether.

[0107] Thereafter, the temperature was raised to 210° C. under normal-pressure nitrogen flow, and the reaction was performed for 7 hours while maintaining 210° C. with stirring. The reaction was carried out while distilling off the generated acetic acid under a nitrogen stream at normal pressure. The reaction liquid after 4 hours and 7 hours after heating up to 210 degreeC was extracted, and it analyzed by GPC (gel permeation chromatography). The results are shown in Table 1.

[0108] Reaction of 2,2-bis{4-(1,3-dioxo-1,3-dihydroisobenzofuran-5-ylcarbonyloxy)phenyl}propane as target (ditrimellitic anhydride ester) The selectivity rate was 96.7%.

Embodiment 2～4）

[0114] The reaction was carried out in the same manner as in Example 1, except that the catalysts described in Table 2 were used in an amount of 4.7 mol % to BPA-DA instead of lithium acetate in Example 1. Table 2 shows the GPC analysis results of the reaction solution after the temperature was raised to 210° C. for 4 hours and 7 hours.

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Abstract

Provided is a process for efficiently producing a trimellitic anhydride phenyl ester in high yield. The process for producing a trimellitic anhydride phenyl ester comprises subjecting a carboxylic acid phenyl ester and trimellitic anhydride or an analogue thereof to transesterification to produce a trimellitic anhydride phenyl ester, and is characterized in that the starting materials are reacted in an aromatic hydrocarbon solvent in the presence of a catalyst comprising an alkali metal salt of a carboxylic acid.

Description

technical field [0001] The present invention relates to the manufacture method of trimellitic anhydride phenyl esters. [0002] In addition, in detail, the present invention relates to a method for producing trimellitic anhydride phenyl esters with high efficiency and high yield. Background technique [0003] Trimellitic anhydride phenyl esters are useful as raw materials for heat-resistant resins such as polyester imide resins, curing agents or modifiers for epoxy resins or polyurethane resins, especially polyester acyl esters produced from bis(trimellitic anhydride) esters In addition to imparting low moisture absorption and low water absorption, imide resin can also impart low thermal expansion, heat resistance, and flexibility depending on the structure, so it is expected to be used in applications such as flexible printed circuit boards (flexible print circuit) , looking for bis(trimellitic anhydride) phenyl esters with higher purity and higher quality. [0004] Some ...

Claims

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Application Information

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IPC IPC(8): C07D307/89C07B61/00
CPCC07D307/89Y02P20/582
Inventor 山本智也村垣耕司川野诚司
Owner HONSHU CHEM INDAL
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