Dramatic Advancements in the Saccharide to 5‐(Chloromethyl)furfural Conversion Reaction

Mascal, Mark; Nikitin, Edward B.

doi:10.1002/cssc.200900136

Cited by 213 publications

(153 citation statements)

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“…All the aprotic solvents were found suitable for the investigated reaction [83]. In this regard, another interesting example is that published by Mascal et al who studied a two-step approach, employing 1,2-dichloroethane as solvent in the first step [84]. In this stage, the conversion of glucose into 5-(chloromethyl)furfural was performed employing concentrated HCl as catalyst in 1,2-dichloroethane heating at 100 • C for 1-3 h [84].…”

Section: Homogeneous and Heterogeneous Catalysts In Organic Solventsmentioning

confidence: 99%

“…In this regard, another interesting example is that published by Mascal et al who studied a two-step approach, employing 1,2-dichloroethane as solvent in the first step [84]. In this stage, the conversion of glucose into 5-(chloromethyl)furfural was performed employing concentrated HCl as catalyst in 1,2-dichloroethane heating at 100 • C for 1-3 h [84]. In the second step, the obtained 5-(chloromethyl)furfural was hydrolyzed to LA in water at 190 • C for 20 min [85], allowing a very high LA yield, up to 79 mol % from glucose, corresponding to 51 wt %.…”

Section: Homogeneous and Heterogeneous Catalysts In Organic Solventsmentioning

confidence: 99%

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New Frontiers in the Catalytic Synthesis of Levulinic Acid: From Sugars to Raw and Waste Biomass as Starting Feedstock

et al. 2016

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Levulinic acid (LA) is one of the top bio-based platform molecules that can be converted into many valuable chemicals. It can be produced by acid catalysis from renewable resources, such as sugars, lignocellulosic biomass and waste materials, attractive candidates due to their abundance and environmentally benign nature. The LA transition from niche product to mass-produced chemical, however, requires its production from sustainable biomass feedstocks at low costs, adopting environment-friendly techniques. This review is an up-to-date discussion of the literature on the several catalytic systems that have been developed to produce LA from the different substrates. Special attention has been paid to the recent advancements on starting materials, moving from simple sugars to raw and waste biomasses. This aspect is of paramount importance from a sustainability point of view, transforming wastes needing to be disposed into starting materials for value-added products. This review also discusses the strategies to exploit the solid residues always obtained in the LA production processes, in order to attain a circular economy approach.

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Section: Homogeneous and Heterogeneous Catalysts In Organic Solventsmentioning

confidence: 99%

Section: Homogeneous and Heterogeneous Catalysts In Organic Solventsmentioning

confidence: 99%

New Frontiers in the Catalytic Synthesis of Levulinic Acid: From Sugars to Raw and Waste Biomass as Starting Feedstock

et al. 2016

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“…A patent discloses that NAG can be synthesized by partial hydrolysis of chitin in 45% yield in the presence of concentrated HCl and 1,2-dichloroethane. 5 SnCl 4 catalyst converted chitin to levulinic acid in 11.5% yield in water. 6 A combined use of AlCl 3 and H 3 BO 3 degraded chitin into 5-hydroxymethylfurfural (5-HMF) in 9.0% yield.…”

Section: Introductionmentioning

confidence: 99%

Hydrolytic hydrogenation of chitin to amino sugar alcohol

2017

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Chitin is the second most abundant biomass and characteristically contains nitrogen atoms in its monomer units. These favourable features promote chitin to be a potential resource for renewable organonitrogen compounds. 2-Acetamido-2-deoxysorbitol (ADS) is an attractive target in derivatives of chitin, but the conversion of chitin to ADS has not been reported so far.In this work, we demonstrate the catalytic conversion of chitin to ADS using mechanocatalysis in the presence of H 2 SO 4 and subsequent hydrolytic hydrogenation by H 2 SO 4 and Ru/TiO 2 without purification process. Our study clarified that the yield of ADS is strongly influenced by the reaction temperature and pH. The hydrolysis favourably proceeds at high temperature and low pH (2.0), but hydrogenation needs low temperature and specific pH of 34 to achieve high selectivity. Specifically, in the hydrogenation step, acid causes various side-reactions of amide and hemiacetal groups especially in the presence of Ru catalyst, whereas even a small amount of base drastically accelerates the retro-aldol reaction to form erythritol and N-acetylethanolamine.Therefore, a one-pot but two-step reaction is necessary to optimise both hydrolysis and hydrogenation steps and maximises the overall yield of ADS up to 52%.

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“…3 outlines the results of these analyses. For 4-9, y was determined as 5.9 ¥ 10 -4 (4), 9.1 ¥ 10 -4 (5), 6.4 ¥ 10 -4 (6), 5.6 ¥ 10 -4 (7), 6.5 ¥ 10 -4 (8) and 4.0 ¥ 10 -4 (9). Surprisingly compound 4 was found to be the most soluble requiring less dense (lower P) CO 2 to maintain a single phase.…”

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confidence: 99%