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Method for preparing 2,5-diacyl-furan 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: 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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  • Method for preparing 2,5-diacyl-furan compound
  • Method for preparing 2,5-diacyl-furan compound
  • Method for preparing 2,5-diacyl-furan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] 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, the product was white crystals, and the yield was 92%. through 1 H-NMR (400MHz, CDCl 3 ) test, CH on the ring, 2H has three peaks, respectively δ (3.18, 5.46, 6.58), such as figure 1 shown.

[0052] Take 16.6g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene and put it into a 100ml reactor, add 20.4g of acetic anhydride, and react with 0.02mol of concentrated sulfuric acid at 160°C for 4h. After completion, it was lowered to room temperature, acetic anhydride was removed by distillation under reduced pressure, and white crystal 2,5-diacetylfuran was obtained by sublimation, with a yield of 86% and a melting point of 135-136°C, as measured by liquid phase mass spectrometry (LC-MS). Molecular weight 152.1, 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2...

Embodiment 2

[0054] 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, the product is white crystals, 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).

[0055] Take 16.6g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene and add it into a 100ml reactor, add 45.0g of formic anhydride, and react with 0.025mol concentrated nitric acid at 180°C for 2h. After completion, it was lowered to room temperature, acetic anhydride was removed by distillation under reduced pressure, and white crystal 2,5-diformyl furan was obtained by sublimation, with a yield of 92%. The molecular weight was 124.1 as measured by liquid phase mass spectrometry (LC-MS). 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H; δ(7.54), CHO, 2H; δ(9.60). Elementa...

Embodiment 3

[0057] 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, the product is white crystals, 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).

[0058] Take 8.3g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene and add it into a 100ml reactor, add 73.1g of propionic anhydride, and react with 0.005mol concentrated hydrochloric acid at 120°C for 8h. After completion, it was lowered to room temperature, propionic anhydride was removed by distillation under reduced pressure, and white crystal 2,5-dipropionyl furan was obtained by sublimation, with a yield of 88%. The molecular weight was 180.1 as measured by liquid phase mass spectrometry (LC-MS). 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H; δ(7.24), CH 2 , 4H; δ(2.78),...

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Abstract

The present invention discloses a method for preparing a 2,5-diacyl-furan compound, and the 2,5-diacyl-furan compound is simply and efficiently prepared by acylation reaction of 2,3-dicarboxylic anhydride-7-oxabicyclo [2.2.1] heptyl-5-ene and / or furan and an acylating agent. The method is simple and efficient, short in process, and less in by-products, and the 2,5-diacyl-furan compound prepared by the method is high in purity, and can meet requirements as high-performance polyester, epoxy resin, polyamide, polyurethane and other engineering plastic raw materials and as chemical raw materials and pharmaceutical 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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