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Method for preparing 2-acetylfuran

A technology of acetylfuran and acetylation, applied in the direction of organic chemistry, can solve the problems of cumbersome process, low yield, harsh operating conditions, etc., and achieve the effect of eliminating environmental pollution, reducing process flow, and reducing energy consumption

Active Publication Date: 2014-06-25
四平市精细化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has a higher yield, but the process is cumbersome, and has the following disadvantages: 1. Due to the use of phosphoric acid with a water content of 15%, part of the acetic anhydride is consumed, resulting in a large amount of acetic anhydride, which cannot be recovered, and a large amount of lye is required for neutralization, resulting in a large amount of acetic anhydride. Salt wastewater is very difficult to treat in industrial production; 2. Chloroform is used as the extraction agent for extraction. Chloroform is a carcinogenic solvent, which has been restricted in use and has a great adverse effect on the occupational health of operators and the environment.
[0006] In addition, there are also reports of using acetyl chloride and acetic acid as acylating agents to react with furan, but due to harsh operating conditions, long reaction time, and low yield, there is basically no industrial value

Method used

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  • Method for preparing 2-acetylfuran
  • Method for preparing 2-acetylfuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 53.6g (0.53mol) of acetic anhydride, 12.0g (0.20mol) of acetic acid, and 1.0g of zinc chloride in sequence into a 250mL three-necked flask equipped with a stirring and condenser, start stirring at 25°C, and drop at this temperature Add 34.0 g (0.50 mol) of furan, drop it in about 1 hour, slowly raise the temperature to 50°C, and keep it warm for 3 hours. After gas chromatography detects that there is no raw material furan, cool down to 30°C. Under the vacuum condition of 50mbar, acetic acid was recovered at 44±2°C, and the fraction at 80~110°C was collected as 2-acetylfuran to obtain 59.3g (0.463mol) of the product with a yield of 92.7% and a purity of 99.8%.

Embodiment 2

[0029] Add 53.6g (0.53mol) of acetic anhydride, 3.0g (0.05mol) of acetic acid, and 1.0g of zinc chloride in sequence into a 250mL three-necked flask equipped with a stirring and condenser, start stirring at 25°C, and drop at this temperature Add 34.0 g (0.50 mol) of furan, drop it in about 1 hour, slowly raise the temperature to 80°C, and keep it warm for 3 hours. After gas chromatography detects that there is no furan raw material, cool down to 30°C. Under the vacuum condition of 50mbar, acetic acid was recovered at 44±2°C, and the fraction at 80~110°C was collected as 2-acetylfuran to obtain 50.0g (0.391mol) of the product with a yield of 78.2% and a purity of 99.6%.

Embodiment 3

[0031] Add 53.6g (0.53mol) of acetic anhydride, 33.0g (0.55mol) of acetic acid, and 1.0g of zinc chloride in sequence into a 250mL three-necked flask equipped with a stirring and condenser, start stirring at 25°C, and drop at this temperature Add 34.0 g (0.50 mol) of furan, drop it in about 1 hour, slowly raise the temperature to 110°C, and keep it warm for 3 hours. After gas chromatography detects that there is no furan raw material, cool down to 30°C. Under the vacuum condition of 50mbar, acetic acid was recovered at 44±2°C, and the fraction at 80~110°C was collected as 2-acetylfuran to obtain 59.0g (0.460mol) of the product, with a yield of 92.0% and a purity of 99.8%.

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Abstract

The invention relates to a method for preparing 2-acetylfuran, which comprises the reaction step of furan acetylation. In the acetylation reaction, in the presence of acetic acid, zinc chloride is used as a catalyst, and acetic anhydride and furan are acylated. The anhydrous zinc chloride is used as the catalyst, so that the acylation reaction temperature and the acylation time are reduced, conditions for furan polymerization are reduced, and the yield is increased. The addition of the acetic acid overcomes the defect that furan autopolymer is produced easily when lewis acid is used as the catalyst for the acylation reaction. Because the zinc chloride and the acetic acid are used, the feed ratio of the reaction raw materials furan and the acetic anhydride is reduced from 1:1.5 in the prior art to 1:1.06, i.e. the reaction is complete, and the difficulty in recycling finished products at the later period is reduced. After the acetic acid is recycled, a finished product can be obtained through direct distillation, complex postprocessing steps such as neutralization, extraction, solvent distillation and the like are avoided, the process flows are greatly reduced, the energy consumption is reduced, and environment pollution increased by unorganized emission is eliminated.

Description

technical field [0001] The invention relates to a new method for preparing 2-acetylfuran from acetic anhydride and furan. Background technique [0002] 2-Acetylfuran is widely used in industrial production as an important organic synthesis raw material, pharmaceutical intermediate and food additive. 2-Acetylfuran is an important intermediate in the synthesis of furanamine salts, and is used in the synthesis of cefuroxime, furonicazone and other drugs for the treatment of tuberculosis. In the food industry, it is mainly used as an additive in coffee, meat-flavored food flavors, soups, meat, seasonings and baked foods. [0003] Synthetic 2-acetylfuran mainly contains the following several methods in the prior art: [0004] U.S. Patent No. 6,274,741 uses metal ion exchange clay as a catalyst, furan and acetic anhydride molar ratio is 5:1, reacts at room temperature with furan as a solvent, and the yield is 78.1% in terms of acetic anhydride, and the yield of this method is re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/46
Inventor 薛亮刘长宝刘丽娟王春艳李世龙王保力陈晓民
Owner 四平市精细化学品有限公司