Method for producing cyclobutane tetracarboxylic acid derivative

A technology of cyclobutane tetracarboxylic acid and its manufacturing method, which can be used in electrical components, circuits, organic chemistry, etc., and can solve the problems of unrecorded isomers, etc.

Active Publication Date: 2016-08-31
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, Patent Document 3 describes that a mixture of 1,3-DMCBDA and 1,2-DMCBDA can be obtained, but does not describe the selective production of the highly useful isomer, that is, the former 1,3-DMCBDA in high yield. -DMCBDA

Method used

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  • Method for producing cyclobutane tetracarboxylic acid derivative
  • Method for producing cyclobutane tetracarboxylic acid derivative
  • Method for producing cyclobutane tetracarboxylic acid derivative

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Embodiment

[0078] Hereinafter, although an Example is given and this invention is demonstrated concretely, this invention is not limited to these Examples.

[0079] In addition, the analysis method used in the Example is as follows.

[0080]

[0081] Device: GC-2010Plus (manufactured by Shimadzu Corporation),

[0082] Column: DB-1 (manufactured by GL Sciences Inc.) 0.25 mm×30 m, film thickness 0.25 μm,

[0083] Carrier gas: He, detector: FID, sample injection volume: 1μL, injection port temperature: 160°C, detector temperature: 220°C, column temperature: 70°C (20min)-40°C / min-220°C (15min) , Split ratio: 1:50, internal standard substance: butyl lactate.

[0084] 1H NMR analysis conditions>

[0085] Apparatus: Fourier transform type superconducting nuclear magnetic resonance apparatus (FT-NMR) INOVA-400 (manufactured by Varian Corporation) 400MHz,

[0086] Solvent: DMSO-d6, internal standard substance: tetramethylsilane (TMS).

[0087]

[0088] Device: DSC1 (manufactured by Mettl...

Embodiment 1

[0096]

[0097] In a nitrogen atmosphere, 0.10 g (0.89 mmol) of citraconic anhydride (CA) and 20 g (222 mmol) of dimethyl carbonate (200 wt. ), stirred with a magnetic stirrer to dissolve it. Then, stirring at 15-20 degreeC, it irradiated with the 100W high-pressure mercury lamp for 4 hours. As a result of quantitative analysis of the reaction solution by gas chromatography after irradiation, the residual rate of citraconic anhydride (CA) was 26.2%. In addition, 2 g of the reaction liquid in the reactor was collected, and the solvent was distilled off at 70-80 Torr with an evaporator. pass 1 It was confirmed by H NMR analysis that the obtained crude product was a mixture containing 1,3-DM-CBDA and 1,2-DM-CBDA (1,3-DM-CBDA:1,2-DM-CBDA=48.3:51.7).

Embodiment 3

[0105]

[0106] Under a nitrogen atmosphere, 35.0 g (312 mmol) of citraconic anhydride (CA) and 152 g (1682 mmol, 4.33 wt. ), stirred with a magnetic stirrer to dissolve it. Then, stirring at 10-15 degreeC, it irradiated with the 100W high-pressure mercury lamp for 48 hours. It was confirmed by gas chromatographic analysis that the residual ratio of raw materials in the reaction liquid was 23.7%. Next, the precipitated white crystals were taken out by filtration at 10-15°C, and the crystals were washed twice with 43.8 g (497 mmol, 1.25 wt times relative to citraconic anhydride (CA)) of ethyl acetate. This was dried under reduced pressure to obtain 8.1 g of white crystals (yield 23.1%). pass 1 It was confirmed by H NMR analysis that the crystal was a mixture containing 1,3-DM-CBDA and 1,2-DM-CBDA (1,3-DM-CBDA:1,2-DM-CBDA=90.3:9.7). In addition, the obtained crystals, filtrate, and cleaning solution were respectively used 1 H NMR analysis and quantitative analysis by gas...

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Abstract

Provided is an efficient method for producing a 1,2,3,4-cyclobutane tetracarboxylic acid-1,2:3,4-dianhydride derivative which is useful as a raw material of polyimide or the like. The present invention is a method for producing a 1,2,3,4-cyclobutane tetracarboxylic acid-1,2:3,4- dianhydride derivative represented by formula (2) by photodimerization of a maleic anhydride compound represented by formula (1) in a diester carbonate solvent. (1) (2) In the formula, R is an alkyl group having 1 to 20 carbon atoms.

Description

technical field [0001] This invention relates to the manufacturing method of the alicyclic tetracarboxylic dianhydride used as a raw material monomer, such as polyamic acid for optical materials, polyimide, etc. Background technique [0002] In general, polyimide resins are widely used as electronic materials such as liquid crystal display elements, protective materials in semiconductors, and insulating materials due to their characteristics, ie, high mechanical strength, heat resistance, insulation, solvent resistance, and the like. In addition, recently, its use as a material for optical communication such as a material for optical waveguides is expected. [0003] In recent years, this field has developed astonishingly, and even higher properties are required for the materials used in it. That is, it is desired not only to be excellent in heat resistance and solvent resistance, but also to have various performances suitable for the intended use. [0004] However, since t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04H10K85/10C08G73/1003C08G73/1007C08G73/1014
Inventor 岛田淳平近藤光正
Owner NISSAN CHEM IND LTD
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