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A class of camphor-based imidazole type ionic liquid and its preparation method and application

An ionic liquid and imidazole-based technology, which is used in the application of catalyzed aldehyde-alcohol oxidative esterification, camphor-based imidazole-based ionic liquid and its preparation field, can solve the problem of tolerance of low-efficiency functional groups, severe reaction conditions, and atom economy Low-level problems, to achieve the effect of good practicability, high catalytic efficiency, safe and easy operation

Active Publication Date: 2021-08-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Common methods for synthesizing ester compounds include: 1) carboxylic acid and alcohol are dehydrated and esterified under the action of strong acid, which has the disadvantages of low efficiency and poor functional group tolerance; 2) first activate carboxylic acid into acid halide, Acid anhydrides or active esters are subsequently prepared by nucleophilic reaction of alcohols. This method has poor atom economy and severe reaction conditions, especially in the acid halide stage; 3) Activate carboxylic acids by condensation reagents such as DCC. This method is also atomic Disadvantages of low economy

Method used

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  • A class of camphor-based imidazole type ionic liquid and its preparation method and application
  • A class of camphor-based imidazole type ionic liquid and its preparation method and application
  • A class of camphor-based imidazole type ionic liquid and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0032] The preparation of embodiment 1 camphor-based imidazole type ionic liquid catalyst

[0033] 1) The structural formula of the camphor-based imidazole type ionic liquid catalyst is:

[0034]

[0035] The preparation process is: 3-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methyl-1-(2,4,6-trimethyl)phenyl- Preparation of 1H-imidazole-3-iodide salt: 18.6g 1-(2,4,6-trimethyl)phenyl-1H-imidazole, 27.8g 10-iodocamphor and 50mLN,N-dimethylformazol Amides were sequentially added to a three-necked flask equipped with a stirrer, a thermometer, and a condensing reflux device, and reacted at 130°C for about 4 hours until one of the raw materials was completely reacted. After cooling, 50 mL of ethyl acetate was added to precipitate the product, and the camphor was obtained by filtration. The crude product of imidazolium iodide salt was recrystallized from ethanol to obtain the target compound. Product characterization data are as follows: yield 81%, 1 H NMR (400MHz, CDCl 3 )δ:...

Embodiment 2

[0060] Example 2 Using the camphor-based imidazole type ionic liquid catalyst prepared in Example 1 to catalyze aldehyde-alcohol oxidative esterification

[0061] 1) Preparation of ethyl benzoate: Accurately weigh 0.1mol benzaldehyde, add it to a 500mL round bottom flask, then add 0.5mol ethanol, 0.005mol 3-(7,7-dimethyl-2-oxobicyclo[ 2.2.1] Hept-1-yl)methyl-1-(2,4,6trimethyl)phenyl-1H-imidazole-3-iodide salt, 0.05mol of cesium carbonate, 150mL of toluene, covered with air Balloon, stirred at 60°C for 3h. After the reaction was completed, it was cooled to room temperature, washed with saturated brine until neutral, concentrated under reduced pressure, and purified by column chromatography to obtain ethyl benzoate with a yield of 98%. Product characterization data are as follows: 1 H NMR (400MHz, CDCl 3 )δ: 8.12-7.96(m, 2H), 7.55-7.46(m, 1H), 7.40(t, J=7.7Hz, 2H), 4.36(q, J=7.1Hz, 2H), 1.37(t, J =7.1Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ: 166.5, 132.7, 130.5, 129.5, 128.2, ...

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Abstract

The invention discloses a class of camphor-based imidazole type ionic liquid, its preparation method and application. The present invention uses camphorsulfonic acid, a derivative of camphor, which is a natural renewable resource, as a raw material to prepare 10-iodated camphor; 10-iodated camphor reacts with aryl imidazole in a quaternization reaction to obtain camphor-based imidazole iodized salt; camphor Ion-exchange imidazole iodide salt with sodium hexafluorophosphate, sodium tetrafluoroborate, bis(trifluoromethanesulfonimide) lithium, etc. to obtain camphor-imidazole hexafluorophosphate and camphor-imidazole tetrafluoroborate , Camphor-based imidazole bis (trifluoromethanesulfonimide) salt plasma liquid. Camphor-based imidazole-based ionic liquids exhibit good catalytic activity for the oxidative esterification of aldehyde-alcohols, and have the advantages of short reaction time, good reaction selectivity, and high product yield, and have good application prospects.

Description

technical field [0001] The invention belongs to the technical field of green synthesis, and specifically relates to a novel camphor-based imidazole-type ionic liquid, a preparation method thereof, and an application in catalyzing aldehyde-alcohol oxidative esterification. Background technique [0002] Esters are an important class of organic compounds with broad application fields. Common methods for synthesizing ester compounds include: 1) carboxylic acid and alcohol are dehydrated and esterified under the action of strong acid, which has the disadvantages of inefficiency and poor functional group tolerance; 2) first activate carboxylic acid into acid halide, Acid anhydrides or active esters are subsequently prepared by nucleophilic reaction with alcohols. This method has poor atom economy and severe reaction conditions, especially in the acid halide stage; 3) Activate carboxylic acids by condensation reagents such as DCC. This method is also atomic The disadvantage of low...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/39C07C69/78C07C201/12C07C205/57C07C69/76C07C253/30C07C255/57C07C69/92C07C69/24B01J31/02
CPCB01J31/0284B01J31/0285B01J2231/70C07C67/39C07C201/12C07C253/30C07D233/60C07C69/78C07C205/57C07C69/76C07C255/57C07C69/92C07C69/24
Inventor 王石发卞天岑赵雨珣徐徐杨益琴谷文
Owner NANJING FORESTRY UNIV
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