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Method for synthesizing heterocyclic acetylized compound by composite catalysis of ionic liquid and phosphoric acid

A technology catalyzed by ionic liquids and phosphoric acid, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve the problem of high prices and increasing Use costs, serious environmental pollution and other issues, to reduce the possibility of side reactions, save costs, and reduce pollution effects

Active Publication Date: 2012-05-30
JIANGSU QINGQUAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the price of trifluoromethanesulfonic acid transition metal salt is high, and toxic solvents such as nitromethane must be used at the same time, and excess acetic anhydride needs to be recovered, so the synthesis cost is relatively high, and the environmental pollution is relatively serious.
[0010] In summary, the existing catalysts used for the acylation reaction of heterocyclic compounds such as furan and thiophene either have the disadvantages of low yield and many side reactions; or the reaction conditions are relatively harsh, such as high reaction temperature and large amount of raw materials; Or in the process of using the existing catalyst, a large amount of organic solvents with relatively high toxicity and relatively high price are used to assist the reaction, thus increasing the cost of use and causing greater environmental pollution

Method used

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  • Method for synthesizing heterocyclic acetylized compound by composite catalysis of ionic liquid and phosphoric acid
  • Method for synthesizing heterocyclic acetylized compound by composite catalysis of ionic liquid and phosphoric acid
  • Method for synthesizing heterocyclic acetylized compound by composite catalysis of ionic liquid and phosphoric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 1.2g of ionic liquid [Bmim]PF to a 100mL flask equipped with an electric stirrer, a thermometer and a condenser tube at room temperature 6 , 1.2g polyphosphoric acid, stir and disperse for 2min, then add 12.3g (0.12mol) of acetic anhydride to stir and disperse, the temperature is 25°C when stirring and dispersing; add 6.8g ( 0.10mol) of furan was added dropwise for about 1 hour, and then the temperature was raised to 50°C for 8 hours. Cool naturally after the reaction is complete, add 200 mL of water, stir for 0.5 h, then extract three times with 100 mL of chloroform (guarantee that the temperature at this time is below 30 ° C), and combine the extracts (organic layer). The extract was adjusted to about pH 6.5 with 30% liquid caustic soda (sodium hydroxide), the organic layer was separated, and the organic layer was washed with water until neutral. Wash with water until the neutral organic layer is recovered by normal pressure distillation to recover chloroform, an...

Embodiment 2

[0041] The catalyst was changed to 1.2g ionic liquid [Bmim]PF 6 And 0.7g polyphosphoric acid, other with embodiment 1, obtains product 2-acetylfuran 10.2g, yield 92.7%, gas phase purity 99.2%. The mass spectrogram of product is as embodiment 1.

Embodiment 3

[0043] The catalyst was changed to 3.6g ionic liquid [Bmim]PF 6 And 1.2g polyphosphoric acid, other are with embodiment 1, obtain product 2-acetylfuran 10.3g, yield 93.6%, gas phase purity 99.1%. The mass spectrogram of product is as embodiment 1.

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Abstract

The invention discloses a method for synthesizing a heterocyclic acetylized compound by the composite catalysis of ionic liquid and a phosphoric acid. The ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate and the phosphoric acid are taken as catalysts to perform acetylation reaction. The method comprises the following steps of: adding the phosphoric acid and the 1-butyl-3-methylimidazolium hexafluorophosphate into a reaction vessel, adding acetic anhydride, and after uniform stirring and dispersion, adding dropwise a heterocyclic compound into the reaction system, wherein the molarratio of the acetic anhydride to the heterocyclic compound is 1.1-1.3:1, and the using amount of the phosphoric acid is 5 to 15 weight percent based on the weight of the acetic anhydride; rising the temperature of the reaction system to 30 to 60 DEG C and performing reaction for 5 to 15 hours; and obtaining the target product by the conventional steps of extracting, washing, distilling and the like. The method has the advantages of not using a large amount of organic solvent in the preparation process, reducing the addition of excessive raw materials, improving the activity of the catalyst atlower temperature and reducing the generation of secondary reaction of the heterocyclic compound to improve the yield, save the cost and improve an operational environment.

Description

technical field [0001] The present invention relates to the technical field of catalyst application, particularly ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([Bmim]PF 6 ) compound phosphoric acid is applied to the method of acetylating heterocyclic compounds such as furan, thiophene and its derivatives with acetic anhydride to synthesize acetylated products, and specifically relates to the method for synthesizing heterocyclic acetylated compounds catalyzed by ionic liquid compound phosphoric acid. Background technique [0002] Heterocyclic acetylated compounds, especially acetylated products of furan, thiophene, pyrrole, indole, etc., such as 2-acetylfuran, are important intermediates of drugs, spices, pesticides, and food additives. Heterocyclic acetylation products are generally obtained through heterocyclic acetylation reactions. [0003] A common heterocyclic acetylation method is to use a heterocyclic compound as a substrate, and then use different ac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/46C07D333/22C07B41/06B01J31/02
Inventor 刘建华张胜建杨荣强聂振中周美丽陈欣荣潘志伟张增礼
Owner JIANGSU QINGQUAN CHEM CO LTD