Preparation method of 2,5-dialkyl furan compound

A technology of alkyl furan and compound, which is applied in the field of preparation of 2,5-dialkyl furan compound, can solve problems such as inability to directly prepare with high-performance polymers, application limitations, etc., achieve simple and efficient preparation method, and get rid of high dependence , the effect of high purity

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

AI Technical Summary

Problems solved by technology

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.

Method used

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  • Preparation method of 2,5-dialkyl furan compound
  • Preparation method of 2,5-dialkyl furan compound
  • Preparation method of 2,5-dialkyl furan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In a 100ml reactor, add 68.0g furan, 78.5g maleic anhydride, 100ml toluene, react at 50°C for 8h, 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%. 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.

[0041] Take 16.6 g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene monomer and put it into a 250ml reactor, add 28.4 iodomethane, and react with 0.02mol concentrated sulfuric acid at 40°C for 20h. After the reaction was completed, the temperature was lowered to room temperature, and 2,5-dimethylfuran was obtained by distillation under reduced pressure, with a yield of 87% and a boiling point of 92-94°C. 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H; δ(5.81), CH 3 , 6H; δ(2.23), such as figure 2 shown.

Embodiment 2

[0043] In a 500ml reactor, add 68.0g furan, 19.6g maleic anhydride, 20ml dichloromethane, react at 100°C for 0.5h, 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, and 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).

[0044] Take 16.6g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene monomer into a 250ml reactor, add 14.2 iodomethane, and react with 0.005mol concentrated hydrochloric acid at 20°C for 24h. After the reaction was completed, the temperature was lowered to room temperature, and 2,5-dimethylfuran was obtained by distillation under reduced pressure, with a yield of 85% and a boiling point of 92-94°C. 1H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H; δ(5.81), CH 3 , 6H; δ(2.23).

Embodiment 3

[0046] In a 200ml reactor, add 68.0g furan, 196g maleic anhydride, 800ml chloroform, react at 80°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 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).

[0047] Take 8.3g of 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hept-5-ene monomer into a 100ml reactor, add 78.0g iodoethane, and react with 0.005mol concentrated nitric acid at 60°C After 16 hours, after the reaction was completed, it was lowered to room temperature, and distilled under reduced pressure to obtain 2,5-diethylfuran with a yield of 92%. 1 H-NMR (400MHz, CDCl 3 ) test, CH on the furan ring, 2H; δ(5.76), CH 2 , 4H; δ(2.44), CH 3 , 6H; δ(1.24).

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Abstract

The application discloses a preparation method of a 2,5-dialkyl furan compound, which simply and high efficiently prepares the 2,5-dialkyl furan compound by carrying out alkylation reaction on a 2,3-dicarboxylic anhydride-7-oxabicyclo[2.2.1]hepta-5-ene and/or a furan and an alkylation agent. The preparation method is simple and high efficient, and has short flow and less by-products. The purity of the 2,5-dialkyl furan compound prepared by the method is high. The 2,5-dialkyl 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-dialkylfuran compound, which belongs to the technical field of preparation of polymer monomers such as high-performance polyesters, epoxy resins, polyamides and polyurethanes, 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-dialkylfuran compound contains a rigid furan ring and a para-position dialkyl structure, and the furan dioic acid and furan diol obtai...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/36
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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