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Preparation method of 2,5-diacyl furan compound

A technology of diacylfuran and compound is applied in the field of preparation of 2,5-diacylfuran compound, can solve the problems of difficulty in large-scale industrial application, complicated 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: 2016-07-06
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are few reports on the synthesis of 2,5-diacyl furan compounds, mainly UchiyamaM 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-diacyl furan compound
  • Preparation method of 2,5-diacyl furan compound
  • Preparation method of 2,5-diacyl furan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] In a 500ml reactor, add 68.0g furan, 78.5g maleic anhydride, 100ml toluene, react at 50°C for 10h, cool and crystallize, 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%. Obtained by 1H-NMR (400MHz, CDCl3), there are three peaks of CH and 2H on the ring, which are respectively δ (3.18, 5.46, 6.58), such as figure 1 shown.

[0054] Take 16.6g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene monomer into a 100ml reactor, add 20.4g of acetic anhydride, and react with 0.02mol concentrated sulfuric acid at 160°C for 2h After the reaction was completed, it was lowered to room temperature, acetic anhydride was distilled off under reduced pressure, and sublimed to obtain white crystal 2,5-diacetylfuran, the yield was 86%, and the melting point was 135-136 ° C. Liquid phase mass spectrometry (LC-MS) The measured molecular weight is 152.1, and the 1H-NMR (400MHz, CDCl3) test is o...

Embodiment 2

[0056] 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).

[0057] 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

[0059] 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).

[0060] 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).

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Abstract

The application discloses a preparation method of a 2,5-diacyl furan compound, which simply and high efficiently prepares the 2,5-diacyl furan compound by carrying out acylation reaction on a 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hepta-5-ene and / or a furan and an acylation agent. The preparation method is simple and high efficient, and has short flow and less by-products. The purity of the 2,5-diacyl furan compound prepared by the method is high. The 2,5-diacyl furan compound can satisfy requirements as raw materials of engineering plastics such as high-performance polyester, epoxy resin, polyamide, and polyurethane and as chemical raw materials and medical intermediate raw materials.

Description

technical field [0001] 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 [0002] 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 the fields of medicine and chemical industry is also limited. [0003] 2,5-diacylfuran compound contains a rigid furan ring and a para-position diacyl structure. After oxidation and reduction, furan dioic acid and...

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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