کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1390216 1500865 2014 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Mechanism of 1-(1-propylsulfonic)-3-methylimidazolium chloride catalyzed transformation of d-glucose to 5-hydroxymethylfurfural in DMSO: an NMR study
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Mechanism of 1-(1-propylsulfonic)-3-methylimidazolium chloride catalyzed transformation of d-glucose to 5-hydroxymethylfurfural in DMSO: an NMR study
چکیده انگلیسی


• d-Glucose to HMF conversion in DMSO was studied using 1H and 13C NMR methods.
• An imidazolium cation-open chain sugar complex was identified as an intermediate.
• HMF formation slows down after first 100 min due to increase in humin formation.

The conversion of d-glucose to 5-hydroxymethylfurfural (HMF) in the presence of 5.48 mol % 1-(1-propylsulfonic)-3-methylimidazolium chloride acidic ionic liquid catalyst in DMSO at 150 °C was studied using 1H, 13C NMR, and visible spectroscopy. The HMF yield rapidly increases in the first 100 min of reaction, however yield drops beyond 100 min and levels off to a maximum yield of about 15.7% around 600 min. The visible spectroscopy study of the reaction mixture suggests that rate of HMF formation slows down after 100 min due to increase in the rate of humin formation after first 100 min. A mechanism has been proposed and key intermediates in the pathway could be identified by studying the 13C NMR spectra of acidic ionic liquid catalyzed transformations of C-1 and C-2 13C labeled d-glucose under identical conditions. The proposed mechanism involves the isomerization of d-glucose to d-fructose via the complexation of the open chain sugar with the imidazolium cation of the acidic ionic liquid catalyst.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 386, 11 March 2014, Pages 86–91
نویسندگان
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