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Preparation method of 2, 5-diacylfuran compound

A technology for diacylfuran and compound, which is applied in the field of preparation of 2,5-diacylfuran compounds, can solve the problems of difficulty in large-scale industrial application, complex synthesis route, low total yield and the like, and achieves simple and efficient preparation method, The effect of high purity and few by-products

Inactive Publication Date: 2021-02-26
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on the synthesis of 2,5-diacyl furan compounds, mainly Uchiyama M et al. synthesized 2,5-diacyl furan compounds [Tetrahedron:Asymmetry, 1997,8( 20): 3467-3474.], but this method has complex synthetic route, low total yield, the shortcoming of high cost, it is difficult to realize large-scale industrial application

Method used

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  • Preparation method of 2, 5-diacylfuran compound
  • Preparation method of 2, 5-diacylfuran compound
  • Preparation method of 2, 5-diacylfuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0064] In a 500ml reactor, add 68.0g furan, 19.6g maleic anhydride, 20ml dichloromethane, react at 100°C for 1h, cool and crystallize, and dry to obtain 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2 .1] Hept-5-ene monomer, the product is white crystal, the yield is 90%. through 1 H-NMR (400MHz, CDCl 3 ) test, CH and 2H on the ring have three peaks, which are respectively δ (3.18, 5.46, 6.58).

[0065] Take 16.6g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene monomer and put it into a 250ml reactor, add 102.6g of chloroacetic anhydride, and react with 0.025mol concentrated nitric acid at 200°C 0.5h, after the reaction was completed, it was lowered to room temperature, and chloroacetic anhydride was distilled off under reduced pressure, and sublimated to obtain white crystal 2,5-dichloroacetylfuran, with a yield of 93%, as measured by liquid phase mass spectrometry (LC-MS). Molecular weight 221.0, 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H, δ (7.24)...

Embodiment 3

[0067] In a 500ml reactor, add 68.0g furan, 9.8g maleic anhydride, 10ml chloroform, react at 70°C for 2h, cool and crystallize, and dry to obtain 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2 .1] Hept-5-ene monomer, the product is white crystal, the yield is 96%. through 1 H-NMR (400MHz, CDCl 3 ) test, CH and 2H on the ring have three peaks, which are respectively δ (3.18, 5.46, 6.58).

[0068] Take 8.3g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene monomer and add it to a 250ml reactor, add 57.8g trifluoroacetic anhydride, 0.005mol concentrated hydrochloric acid at 160°C Reacted for 6h, after the reaction was completed, it was lowered to room temperature, trifluoroacetic anhydride was distilled off under reduced pressure, and white crystal 2,5-bis-(trifluoroacetyl)furan was obtained by sublimation, with a yield of 88%, liquid phase mass spectrometry (LC -MS) records molecular weight 260.1, 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H, δ (8.14).

Embodiment 4

[0070] In a 500ml reactor, add 68.0g of furan, 24.5g of maleic anhydride, 60ml of petroleum ether, react at 30°C for 6h, crystallize out, and dry to obtain 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1 ]hept-5-ene monomer, the product is a white crystal, and the yield is 92%. through 1 H-NMR (400MHz, CDCl 3 ) test, CH and 2H on the ring have three peaks, which are respectively δ (3.18, 5.46, 6.58).

[0071] Take 16.6g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene monomer and put it into a 100ml reactor, add 15.5g of heptafluorobutyric anhydride, 0.005mol concentrated phosphoric acid at 100°C After 12 hours of reaction, after the reaction was completed, it was lowered to room temperature, and heptafluorobutyric anhydride was distilled off under reduced pressure, and crystal 2,5-bis-(heptafluorobutyryl) furan was obtained by sublimation, with a yield of 83%, liquid chromatography mass spectrometry (LC- MS) records molecular weight 460.1, 1 H-NMR (400MHz, CDCl ...

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Abstract

The invention discloses a preparation method of a 2, 5-diacylfuran compound. The preparation method comprises the following steps: carrying out acylation reaction on 2, 3-dicarboxylic anhydride-7-oxabicyclo [2.2. 1] heptyl-5-alkene and an acylation reagent to simply, conveniently and efficiently prepare the 2, 5-diacylfuran compound. The preparation method is simple, efficient, short in process and few in by-product, and the 2, 5-diacylfuran compound prepared by the method is high in purity and can meet the requirements of being used as a raw material of engineering plastics such as high-performance polyester, epoxy resin, polyamide and polyurethane and being used as a chemical raw material and a medical intermediate raw material.

Description

[0001] This case is a divisional application with an application date of December 11, 2014, an application number of 201410765238.3, and an invention title of a preparation method for a 2,5-diacylfuran compound. technical field [0002] The application relates to a preparation method of a 2,5-diacyl furan compound, which belongs to the technical field of preparation of polymer monomers such as high-performance polyester, epoxy resin, polyamide and polyurethane, and chemical and pharmaceutical intermediates. Background technique [0003] At present, the raw materials of alcohol, acid and ester monomers containing rigid ring structure used in the synthesis of high-performance engineering plastics such as polyester, epoxy resin, polyamide and polyurethane are single. Furan is an important aromatic monomer. However, because its structure does not contain bifunctional active groups, it cannot be directly used in the preparation of high-performance polymers, and its application in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46
Inventor 王静刚刘小青朱锦那海宁
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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