Preparation method of 2, 5-diacetyl furan

A technology of diacetylfuran and acylation, applied in directions such as organic chemistry, can solve problems such as difficulty in large-scale industrial application, complex synthesis route, low total yield, etc., and achieves simple and efficient preparation method, high purity, and by-products. less effect

Pending Publication Date: 2021-02-05
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
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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-diacetyl furan
  • Preparation method of 2, 5-diacetyl furan
  • Preparation method of 2, 5-diacetyl furan

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, 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.

[0054] 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 9

[0056] 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 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 into a 100ml reactor, add 15.7g of acetyl chloride, 0.001molSnCl 4 React at 100°C for 6 hours, after the reaction is completed, cool down to room temperature, distill off acetyl chloride under reduced pressure, and sublimate to obtain white crystal 2,5-diacetylfuran, the yield is 88%, the melting point is 135-136°C, liquid phase mass spectrometry (LC-MS) records molecular weight 152.1, 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H; δ(7.24), CH 3 , 6H; δ(2.59). Elemental Analysis C 8 h 8 o 3 Calculate...

Embodiment 10

[0059] 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 and 2H on the ring have three peaks, which are respectively δ (3.18, 5.46, 6.58).

[0060] Take 16.6g of 2,3-diformic anhydride-7-oxabicyclo[2.2.1]hept-5-ene and add it into a 100ml reactor, add 24.6g of acetyl bromide, and add 0.001mol of boron trifluoride etherate complex in Reacted at 100°C for 6h, after the reaction was completed, it was cooled to room temperature, acetyl bromide was removed by distillation under reduced pressure, and white crystal 2,5-diacetylfuran was obtained by sublimation, with a yield of 87% and a melting point of 135-136°C. LC-MS) records molecular weight 152.1, 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H; δ(7.24), CH 3 , 6H; δ(2.59)...

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Abstract

The invention discloses a preparation method of 2, 5-diacetyl furan. The method comprises the following steps: carrying out acylation reaction on 2, 3-phthalic anhydride- 7-oxabicyclo [2.2. 1] heptyl-5-ene and an acylation reagent to simply, conveniently and efficiently prepare the 2, 5-diacetyl furan. The preparation method is simple, efficient, short in process and few in byproducts, and the 2,5-diacetyl furan 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, polyurethane and the like 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 201410763313.2, and an invention name of a preparation method for a 2,5-diacylfuran compound. technical field [0002] The application relates to a preparation method of 2,5-diacetylfuran, 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 the fields ...

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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