Process for producing cyclobutane tetracarboxylic acid derivatives

A technology of cyclobutane tetracarboxylic acid and its manufacturing method, which is applied in organic chemistry and other fields, can solve problems such as insufficient photoreaction efficiency, and achieve high photoreaction efficiency

Active Publication Date: 2018-07-06
NISSAN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the method for producing 1,2,3,4-cyclobutanetetracarboxylic acid-1,2:3,4-dianhydride (CBDA) by the photodimerization reaction of maleic anhydride described in Patent Document 1, as a raw material Maleic anhydride is relatively cheap, and is simple and useful as a production method, but the photoreaction efficiency is not sufficient, and there is a problem in the yield of the target product

Method used

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  • Process for producing cyclobutane tetracarboxylic acid derivatives
  • Process for producing cyclobutane tetracarboxylic acid derivatives
  • Process for producing cyclobutane tetracarboxylic acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0073] Examples are listed below to explain the present invention in more detail, but the present invention is not limited to these examples. It should be noted that the analysis methods used in the examples are as follows.

[0074]

[0075] Device: GC-2010Plus (manufactured by Shimadzu Corporation),

[0076] Column: DB-1 (manufactured by Agilent Technologies, Ltd.) 0.25 mm in diameter × 30 m in length, 0.25 μm in film thickness,

[0077] 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.

[0078] 1 H NMR analysis conditions>

[0079] Device: Fourier transform type superconducting nuclear magnetic resonance device (FT-NMR) INOVA-400 (manufactured by Varian) 400MHz,

[0080] Solvent: DMSO-d6, internal standard substance: tetramethylsilane (TMS).

[0081]

[0082] Device: DSC1 (manufactured by Me...

Embodiment 10

[0101]

[0102] In a nitrogen atmosphere, in a 300mlLPyrex (registered trademark) glass five-necked flask was put 3.5g (31.2mmol) of citraconic anhydride (CA), 0.70g (3.23mmol) of 4-chlorobenzophenone (ClBP), Conic anhydride (CA) (10 mol%) and 136.5 g (1515 mmol, 39.0 wt times of citraconic anhydride (CA)) and dimethyl carbonate were stirred and dissolved with a magnetic stirrer.

[0103] Then, while stirring at 10-15°C, a 100W high-pressure mercury lamp was irradiated for 1 hour. As a result of the quantitative analysis of the reaction liquid by gas chromatography after irradiation, the residual rate of citraconic anhydride (CA) was 69.1%. In addition, 0.2 g of the reaction liquid in the reactor was taken, and the solvent was distilled off at 70-80 Torr with an evaporator. by 1 H NMR analysis confirmed 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=44.6:55.4).

Embodiment 11～13

[0105] A series of operations were performed in the same manner as in Example 10, and it was implemented so that the type of sensitizer became the value shown in the following table. In addition, the residual rate of citraconic anhydride, the reaction rate, and the production ratio of 1,3-DM-CBDA to 1,2-DM-CBDA in the reaction solution obtained here were calculated, and the results are shown together with the results obtained in Example 10. In the table. It should be noted that the reaction rate in the table is calculated from the number of moles of citraconic acid used and the residual rate of citraconic acid at the time of the reaction for 1 hour.

[0106] [Table 2]

[0107]

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Abstract

To provide an efficient method for producing 1,2,3,4-cyclobutanetetracarboxylic acid-1,2:3,4-dianhydride derivatives useful as raw materials for polyimides and the like. Make the maleic anhydride compound represented by formula (1) in the presence of benzophenone substituted with electron-withdrawing groups, acetophenone substituted with electron-withdrawing groups or benzaldehyde substituted with electron-withdrawing groups The photodimerization reaction takes place to produce the method for 1,2,3,4-cyclobutanetetracarboxylic acid-1,2:3,4-dianhydride derivatives shown in formula (2). (In the formula, R represents a hydrogen atom or an alkyl group having 1 to 20 carbons.)

Description

Technical field [0001] The present invention relates to a novel method for producing a cyclobutanetetracarboxylic acid derivative useful as a raw material for polyimide and the like. Background technique [0002] Cyclobutane tetracarboxylic acid derivatives are compounds useful as raw materials for polyimides and the like. As a method for producing this compound, a photodimerization reaction of a maleic anhydride derivative is known (Patent Documents 1 to 5). [0003] Among them, in Patent Document 1, as a method for producing 1,2,3,4-cyclobutanetetracarboxylic acid-1,2:3,4-dianhydride (CBDA), a solvent having a carbonyl group such as ketones is disclosed The photodimerization reaction of maleic anhydride. However, there is a description that in this reaction, the use of acetophenone, benzophenone, anthraquinone, etc., which are generally used as photosensitizers, is ineffective, and instead gives good results in the absence of it (Patent Document 1 No. (2) The last line of the ...

Claims

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Application Information

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