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The Synthesis and Catalytic Appucation of Perfluoroalkylsulfonylimide-Functionalized Ionic Liquids

Author: YangQiuHong
Tutor: MaJingZhong; MaZhongHua
School: Huazhong Agricultural University
Course: Applied Chemistry
Keywords: Perfluoroalkylsulfonylimide Functionalized ionic liquids Cellulose Hydrolysis HMF
CLC: O643.36
Type: Master's thesis
Year: 2013
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Functionalized ionic liquids can greatly enhance the versatility and the usable range of the ordinary ionic liquids which can be used as the reaction medium and reagents.Bis[(perfluoroalkyl)sulfonyl]imides, whose anion has a strong stability since negative charge of nitrogen atom can be highly delocalized onto the whole S-O-N framework due to strongly electron-drawing and steric effects from the perfluorinated alkyl chains, is a new class of fluorine-containing organic superacid.Ionic liquids bearing strongly acidic functional groups is an important research area to prepare efficient, environmentally friendly, and "green" cleaning catalysts.In this work, we attempted to prepare potassium (3-chloropropylsulfonyl perfluoroalkylsulfonyl)imide (3x,3y) by perfluoroalkyl sulfonamide potassium salt and3-chloropropyl sulfonyl chloride. Further,3x,3y reacted with N-methylimidazole respectively, and generated1-(3-(N-(perfluoroalkylsulfonyl)sulfamoyl)propyl)-3-methyl imidazolium (4x,4y), and the synthesis conditions was optimized. The results showed that the optimal synthesis conditions of4x,4y was120℃and48h, which yield up to95%.Then, target ionic liquids ([bCFNHMIM]mXm) were obtained by reaction of4x,4y with a series of small molecule acid respectively, whose structures were confirmed by FT-IR, NMR, LC-MS methods. Hammett index was used to determine the Hammett acidity functions (Ho) of [bCFNHMIM]mXm, whose Ho values were between0.66and-0.93, which were stronger than that of ionic liquids bearing sulfonic acid group (Ho=0.25-1.44).Cellulose transformed into reducing sugars, furfural, ethanol and high value-added chemicals is an important way to solve the energy crisis and environmental pollution. In this paper, we studied the catalytic activity of [bCFNHMIM]mXm for cellulose hydrolysis in l-butyl-3-methylimidazolium ([BMIM]Cl) system. We obtained that the optimal conditions of the hydrolysis of cellulose were:100℃,20mol%catalyst dosage, and3 mol equiv of water to the AGU. In the optimum conditions, we found [CFNHMIM]mXm have an good catalytic activity on cellulose hydrolysis, specially, TRS, HMF yields were as high as62%,34%respectively. The results show that,[bCFNHMIM]mXm with only20mol%dosage have a greater advantage than sulfonic acid-based ionic liquids with87mol%dosage in the catalytic hydrolysis of cellulose.Further, we probed the influence on cellulose hydrolysis of the metal chlorides (Mn2+, Cr3+, Fe3+, Fe2+, Zn2+, La3+) as co-catalysts in [1CFNHMIM]4SiW12O40catalyst system. The study found that the metal chlorides can largely contribute to the degradation of cellulose, and HMF yield up to41%in2h with5mol%MnCl2/[1CFNHMIM]4SiW12O40.

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CLC: > Mathematical sciences and chemical > Chemistry > Physical Chemistry ( theoretical chemistry ),chemical physics > Chemical kinetics,catalysis > Catalytic > Catalyst
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