Preparation of halogenated furfurals as intermediates in the carbohydrates to biofuel process

Meller, Elad; Aviv, Avishay; Aizenshtat, Zeev; Sasson, Yoel

doi:10.1039/c6ra06050a

Cited by 6 publications

(1 citation statement)

References 31 publications

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“…So, the above‐reported method is cumbersome for the quantification of CMF yield. Yet other reports have employed a NMR‐based method and an UV–vis spectroscopy based method for the quantification of CMF 20,21 . Consequently, the development of a sensitive, specific, and valid analytical method for the routine analysis of CMF remains a primary requisite.…”

Section: Introductionmentioning

confidence: 99%

5‐(Chloromethyl)furfural production from glucose: A pioneer kinetic model development exploring the mechanism

Antonyraj

Chennattussery

Haridas

2021

Int J of Chemical Kinetics

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Conversion of glucose to 5-(chloromethyl)furfural (CMF) is one of the wellknown high yield unit processes in lignocellulosic biomass valorization. A kinetic modeling study was not reported for the reaction, owing to the complexity in quantification of CMF. Herein we have successfully developed a rapid, sensitive, and specific HPLC method (reverse phase) to quantify the generated CMF (range: 10-650 μg/mL) in a dichloroethane solvent. The Box-Behnken design of experiment method employed for the statistical optimization. A kinetic model was developed based on the homogeneous first-order kinetic model, and the results are in good agreement with the experiment data. The formation of CMF, 5-(hydroxymethyl)furfural, formic acid, levulinic acid, and humins from glucose and HCl were modeled using a serial parallel reaction mechanism. The apparent activation energy (E a ) for glucose decomposition and CMF formation is 99 and 31 kJ/mol. K E Y W O R D S5-(chloromethyl)furfural, design of experiment, glucose dehydration, kinetic model, nonlinear least-squares method

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Section: Introductionmentioning

confidence: 99%

5‐(Chloromethyl)furfural production from glucose: A pioneer kinetic model development exploring the mechanism

Antonyraj

Chennattussery

Haridas

2021

Int J of Chemical Kinetics

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Industrial Routes from Sugars and Biomass to CMF and Other 5‐(Halomethyl)furfurals

Bueno Morón,

Arbore,

van Klink

et al. 2024

ChemSusChem

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The synthesis of 5‐(halomethyl)furfurals (XMFs, X = F, Cl, Br, I), including 5‐(chloromethyl)furfural (CMF), 5‐(bromomethyl)furfural (BMF), 5‐(iodomethyl)furfural (IMF), and 5‐(fluoromethyl)furfural (FMF), from biomass represents a pivotal advancement in renewable chemistry and engineering. Harnessing waste biomass as a raw material offers a sustainable alternative to fossil‐based resources, mitigating environmental degradation and addressing pressing energy needs. CMF and BMF, characterized by their enhanced stability over the hydroxyl analog, 5‐(hydroxymethyl)furfural (HMF), exhibit promise as renewable building blocks for scale‐up and commercialization. The surge in research interest, particularly from 2010 to 2024, reflects a growing recognition of XMFs' potential as novel platform chemicals. This review highlights the evolution of XMF synthesis methods, focusing on their transformation from saccharides and lignocellulosic biomass. Mechanistic insights and experimental setups are scrutinized for industrial feasibility and scalability, shedding light on technical challenges and avenues for further research. The analysis underscores the burgeoning significance of XMFs in the transition towards sustainable chemical production, emphasizing the importance of process optimization and mechanistic understanding for commercial deployment.

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Phase Transfer Catalyst Assisted One‐Pot Synthesis of 5‐(Chloromethyl)furfural from Biomass‐Derived Carbohydrates in a Biphasic Batch Reactor

Onkarappa

Dutta

2019

ChemistrySelect

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5‐(Chloromethyl)furfural (CMF), a bio‐renewable chemical building block, has been produced in good isolated yields from biomass‐derived carbohydrates within a closed aqueous HCl‐1,2‐dichloroethane biphasic reactor in the presence of benzyltributylammonium chloride (BTBAC) as a phase transfer catalyst (PTC). The solvent‐economic, one‐pot strategy afforded CMF in 73% isolated yield (90 °C, 3 h) from sucrose with a combined yield of 84% for CMF and levulinic acid. The process was optimized on temperature, duration, solvent, type, and loading of PTC. Use of BTBAC led to nearly 10% increase in yield of CMF for all substrates when compared to control reactions.

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Preparation of halogenated furfurals as intermediates in the carbohydrates to biofuel process

Abstract: Efficient processe for the production of CMF and BMF is demonstrated in a biphasic system of aqueous acid and 1,2-dichloroethane.

Cited by 6 publications

References 31 publications

5‐(Chloromethyl)furfural production from glucose: A pioneer kinetic model development exploring the mechanism

5‐(Chloromethyl)furfural production from glucose: A pioneer kinetic model development exploring the mechanism

Industrial Routes from Sugars and Biomass to CMF and Other 5‐(Halomethyl)furfurals

Phase Transfer Catalyst Assisted One‐Pot Synthesis of 5‐(Chloromethyl)furfural from Biomass‐Derived Carbohydrates in a Biphasic Batch Reactor

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