Conversion of fructose into 5-hydroxymethylfurfural and alkyl levulinates catalyzed by sulfonic acid-functionalized carbon materials

Abstract

A series of sulfonic acid-functionalized carbon materials (C-SO 3 H), including poly( p-styrenesulfonic acid)grafted carbon nanotubes (CNT-PSSA), poly(p-styrenesulfonic acid)-grafted carbon nanofibers (CNF-PSSA), benzenesulfonic acid-grafted CMK-5 (CMK-5-BSA), and benzenesulfonic acid-grafted carbon nanotubes (CNT-BSA), have been studied for fructose dehydration to 5-hydroxymethylfurfural (HMF) and fructose alcoholysis to alkyl levulinate. A study for optimizing the reaction conditions such as the catalyst loading, the reaction time, and the temperature has been performed. Under the optimal conditions, high HMF and ethyl levulinate yields of up to 89% and 86%, respectively, are obtained. The catalytic activities of C-SO 3 H for the conversions of fructose into both HMF and ethyl levulinate follow the order of their acid strength. The relationship between the catalytic activity and acid density of C-SO 3 H shows a linear correspondence in the fructose dehydration to HMF. The facile separation, ease of recovery, and high thermal stability make the developed C-SO 3 H efficient and environment-friendly catalytic materials for transforming biomass carbohydrate into fine chemicals. † Electronic supplementary information (ESI) available: See

Conversion of Carbohydrates into Platform Chemicals Catalyzed by Alkaline Ionic Liquids

“…The maximum glucose content was found to be 13.42% at 20 min, followed by a sharp decrease after 20 min. The glucose detected after 60 min was only 2.03%, suggesting that the conversion of glucose into 5-HMF is the committed step compared to the transformation of MCC into glucose-based small molecules in this IL-solvent system, similar to the result reported by Liu et al [37]. Although the change in cellobiose content had a similar trend to that of glucose, as indicated in Figure 2B, the absolute quantity of cellobiose detected was much lower than that of glucose.…”

Progress in the Development of Mesoporous Solid Acid and Base Catalysts for Converting Carbohydrates into Platform Chemicals

“…To overcome this limitation CMK-3 has been developed as an ordered mesoporous carbon material which has a large surface area and excellent accessibility of substrates to the active sites within the well-defi ned mesopores of the carbon materials. Ma et al [ 37 ] selected the ordered mesoporous carbon materials such as CNTs, carbon nanofi bers (CNFs), and hexagonal tube like CMK-5 as supports to prepare a series of sulfonic acid-functionalized carbon materials (C-SO 3 H), such as poly (p-styrenesulfonic acid)-grafted carbon nanotubes (CNT-PSSA), poly(pstyrenesulfonic acid)-grafted carbon nanofi bers (CNF-PSSA), benzene sulfonic acid-grafted CMK-5 (CMK-5-BSA), and benzene sulfonic acid-grafted carbon nanotubes (CNT-BSA). The loadings of -SO 3 H group of the above four C-SO 3 H materials were in the order 5.67, 4.26, 2.89, and 1.75 mmol/g, with the acid strength found to increase with -SO 3 H loading.…”

Functional carbons and carbon nanohybrids for the catalytic conversion of biomass to renewable chemicals in the condensed phase

“…Carbon nanotubes and nanofibers functionalized with poly(p-styrenesulfonic acid) and benzenesulfonic acid groups were tested for the conversion of fructose to 5-HMF [128]. A linear correlation between acid site density and fructose conversion was observed.…”