Method for producing cyclobutane tetracarboxylic acid derivative

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: 2016-08-31
NISSAN CHEM IND LTD
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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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  • Method for producing cyclobutane tetracarboxylic acid derivative
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  • Method for producing cyclobutane tetracarboxylic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0073]The following examples are given to illustrate the present invention in more detail, but the present invention is not limited to these examples. In addition, the analysis method used in the Example is as follows.

[0074]

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

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

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

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

[0081]

[0082] Device: D...

Embodiment 10

[0101]

[0102] Under a nitrogen atmosphere, 3.5 g (31.2 mmol) of citraconic anhydride (CA) and 0.70 g (3.23 mmol) of 4-chlorobenzophenone (ClBP) were charged into a 300 mL Pyrex (registered trademark) glass five-necked flask. Conic anhydride (CA) is 10 mol%) and dimethyl carbonate 136.5 g (1515 mmol, 39.0 wt times relative to citraconic anhydride (CA)) were stirred and dissolved with a magnetic stirrer.

[0103] Next, stirring at 10-15 degreeC, it irradiated with the 100W high-pressure mercury lamp for 1 hour. As a result of quantitative analysis of the reaction solution 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 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=44.6:55.4).

Embodiment 11～13

[0105] A series of operations were performed in the same manner as in Example 10, and the types of sensitizers were set to the values ​​shown in the table below. In addition, the residual rate of citraconic anhydride, the reaction rate, and the production ratio of 1,3-DM-CBDA and 1,2-DM-CBDA were calculated in the reaction solution obtained here, and are shown together with the results obtained in Example 10. in the table. It should be noted that the reaction rates in the table were calculated from the number of moles of citraconic acid used and the residual rate of citraconic acid at the point of reaction for 1 hour.

[0106] [Table 2]

[0107]

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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) under the presence of a benzophenone substituted with an electron-attracting group, an acetophenone substituted with an electron-attracting group, or a benzaldehyde substituted with an electron-attracting group. (1) (2) (In the formula, R is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.)

Description

technical field [0001] The present invention relates to a novel production method of cyclobutane tetracarboxylic acid derivatives useful as raw materials for polyimide and the like. Background technique [0002] Cyclobutane tetracarboxylic acid derivatives are useful compounds as raw materials for polyimides and the like. As a method for producing this compound, photodimerization of a maleic anhydride derivative is known (Patent Documents 1 to 5). [0003] Among them, Patent Document 1 discloses a solvent having a carbonyl group in ketones or the like as a method for producing 1,2,3,4-cyclobutanetetracarboxylic acid-1,2:3,4-dianhydride (CBDA). Photodimerization of maleic anhydride in . 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 when they do not exist (Patent Document 1, No. (2) the last line of the lower right...

Claims

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Application Information

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