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Ionic liquid containing cinnamyl functional groups and preparation method thereof

An ionic liquid and functional-based technology, which is applied in the field of ionic liquid preparation, can solve the problems of unsuitability for large-scale industrial production applications, strong corrosion of equipment, complex synthesis process, etc., and achieve post-processing green environmental protection, simple preparation process, Post-processing simple effects

Inactive Publication Date: 2010-03-17
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The previous preparation of quaternary ammonium salt ionic liquids containing cinnamon groups also has some shortcomings: for example, the synthesis process is complicated, the by-products are more, the equipment is highly corrosive, the post-reaction treatment is complicated, the environment is polluted, and it is not suitable for large-scale production. Disadvantages such as industrial production and application limit its application

Method used

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  • Ionic liquid containing cinnamyl functional groups and preparation method thereof
  • Ionic liquid containing cinnamyl functional groups and preparation method thereof
  • Ionic liquid containing cinnamyl functional groups and preparation method thereof

Examples

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Effect test

example 1

[0043] Synthesis of 1-cinnamyl-3-methylimidazolium chloride salt: mix 8.2g (0.1mol) N-methylimidazole with 15.2g (0.1mol) cinnamyl chloride, stir at room temperature for 3 hours to obtain a light yellow viscous liquid , add 5 mL of acetonitrile or chloroform, continue the reaction for 1 hour, remove the solvent with a rotary evaporator, wash with ethyl acetate (2 × 20 mL), and obtain a light yellow viscous liquid, which is the target product, with a yield of 94%. 1 HNMR (300Hz, D 2 O), δ: 8.55 (s, 1H, NCH=N), 7.37 (d, 2H, NCH=CHN), 7.31-7.25 (m, 5H, C 6 h 5 ), 6.67 (d, 1H, C 6 h 5 CH), 6.27 (m, 1H, CHCH 2 ), 4.77 (d, 2H, CHCH 2 ), 3.73 (s, 3H, NCH 3 ).

example 2

[0045] Synthesis of N-cinnamyl pyridinium chloride salt: 7.9g (0.1mol) pyridine was mixed with 15.2g (0.1mol) cinnamyl chloride, stirred at room temperature for 2 hours, washed with ethyl acetate (2×20mL), and brown viscous was obtained The liquid is the target product, and the yield is 93%. 1 HNMR (300Hz, CDCl 3 )δ: 9.7, 8.41, 8.06 (d, t, t, 5H, C 5 h 5 N), 7.37-7.23 (m, 5H, C 6 h 5 ), 7.14(d, 1H, C 6 h 5 CH), 6.52 (m, 1H, CHCH 2 ), 5.90 (d, 2H, CHCH 2 ).

example 3

[0047] Synthesis of N-methyl-N-cinnamylpyrrolidone chloride salt: 9.9g (0.1mol) N-methylpyrrolidone and 15.2g (0.1mol) cinnamyl chloride were mixed, set the temperature at 30°C, stirred for 2 hours, and dissolved in ethyl acetate The ester was washed (2×20 mL) to obtain a light yellow viscous liquid, which was recrystallized with a mixed solvent of ethanol and ether (volume ratio 2:1) to obtain the target product with a yield of 93%. 1 HNMR (300Hz, CDCl 3 )δ: 7.72-7.38 (m, 5H, C 6 h 5 ), 7.31(d, 1H, C 6 h 5 CH), 7.01(d, 2H, CHCH 2 N), 6.41 (m, 1H, CHCH 2 ), 5.18 (d, 2H, NCH 2 CH 2 ), 4.05 (s, 3H, NCH 3 ), 4.00 (t, 2H, COCH 2 ), 3.71 (m, 2H, CH 2 -CH 2 -CH 2 ).

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Abstract

The invention relates to ionic liquid containing cinnamyl functional groups and a preparation method thereof. The ionic liquid has a general formula of R<+>Y<->, wherein R is substituted or unsubstituted iminazole, pyridine or pyrrolidone containing cinnamyl functional groups, and Y is selected from chlorine, bromine, iodine, acetate radical, sulfate radical, phosphate radical, nitrate radical, thiocyanate radical, tetrafluoroborate radical, hexafluorophosphate racial, toluenesulfonate radical, and the like. The ionic liquid is a favorable novel green chemical material and has wide applicationprospects in the fields of organic synthesis, medicines, new materials, and the like. The preparation method has the advantages of convenient and easily-obtained raw materials, simple preparation process, mild reaction conditions, high production rate, simple after-treatment, green and environmental protection and the like and provides a foundation for researching and developing novel functionalionic liquid and industrial production application thereof.

Description

technical field [0001] The invention relates to the preparation of ionic liquids, in particular to an ionic liquid containing cinnamyl functional groups and a preparation method thereof, specifically imidazole-, pyridine-, and pyrrolidone-based ionic liquids containing cinnamyl-containing ionic liquids and the preparation method of the ionic liquid, which belongs to a novel Chemical materials and their preparation technology. Background technique [0002] Ionic liquids (Ionic liquids) have been a research hotspot in the field of green chemistry in recent years. Due to their superior properties such as large liquid temperature range, wide dissolution range, low vapor pressure, good thermal stability, designability, and recyclability, they have been used in many fields. Many fields such as organic synthesis, catalysis, extraction and separation, functional materials, electrochemistry and life sciences show good application prospects (Angew.Chem.Int.Ed.2004, 45, 1983-1986, Natu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58C07D213/20C07D207/267
Inventor 纪秀杰程博闻宋俊刘超
Owner TIANJIN POLYTECHNIC UNIV
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