Abstract
The production of bio-diesel fuels from carbohydrates is a promising alternative to fossil fuels with regard to the growing severity of the environmental problem and energy crisis. Potential bio-diesel candidates or additives, such as 5-(hydroxymethyl)-2-(dimethoxymethyl) furan (HDMF), 2-(dimethoxymethyl)-5-(methoxymethyl) furan (DMMF), and 5-(methoxymethyl)-2-furaldehyde (MMF) could be produced from the alcoholic solutions of both 5-HMF and fructose in the presence of solid acid catalysts. In the present study, a readily prepared, silica, gel-supported nitric acid (SiO2-HNO3) catalyst was found to be exceptionally reactive for the production of HDMF from fructose. A DMSO-methanol biphasic solvent system was developed and HDMF, DMMF, and MMF were observed at 150 °C, with maximum yields of 34%, 34%, and 25%, respectively. Meanwhile, a maximum HDMF yield of 77% was obtained from 5-HMF in methanol. Moreover, a sequential, one-pot, two-step dehydration/acetalization process, involving the dehydration of fructose to 5-HMF in dimethylsulfoxide (DMSO) at 150 °C, and followed by adding a certain amount of methanol to react with the formed 5-HMF to HDMF at 100 °C, was developed to promote the yield of HDMF. The optimum yield of HDMF reached 70% with the complete conversion of fructose. The reaction mechanisms of dehydration and acetalization have been proposed for the conversion of 5-HMF to HDMF. The two-step design allows for facile catalyst recycling while supplying as a promising method for the production of biodiesel from complex carbohydrates.
Highlights
Biomass represents an ideal substitute for fossil fuels and is considered as a potential renewable resource of energy and organic compounds [1,2]
5-(hydroxymethyl)-2-(dimethoxymethyl) furan (HDMF), 2-(dimethoxymethyl)-5-(methoxymethyl) furan (DMMF), and 5-(methoxymethyl)-2-furaldehyde (MMF); they are recognized as excellent additives for diesel due to their energy density and blending properties [5,6]
Due to the bifunctionality of 5-HMF, a large number of competitive reactions such as oxidation, etherification, and polymerization might occur in the system [15]; the use of a selective catalyst to promote the acetalization of 5-HMF is an essential part of the research
Summary
Biomass represents an ideal substitute for fossil fuels and is considered as a potential renewable resource of energy and organic compounds [1,2]. 5-Hydroxymethylfurfural (5-HMF) is one of the most important biomass-derived platform compounds and can be used to produce various chemicals [3,4]. The acetals of 5-HMF have been obtained during the conversion of 5-HMF into derivatives with alcohols in acid mediums, including. It was found that both the conversion of 5-HMF and the yield of the corresponding acetals were low when using long-chain alcohols as reactants and solvents simultaneously, possibly due to long chain alcohols’. The short-chain alcohol methanol was employed as a reactant during the acetalization of 5-HMF to reduce the passivation rate of the catalyst and allow easy removal of the solvent
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