Hydrochloric acid-catalyzed coproduction of furfural and 5-(chloromethyl)furfural assisted by a phase transfer catalyst

Bhat, Navya Subray; Vinod, Nivedha; Onkarappa, Sharath Bandibairanahalli; Dutta, Saikat

doi:10.1016/j.carres.2020.108105

Cited by 9 publications

(5 citation statements)

References 31 publications

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“…Humin was obtained as the side product during the dehydration of xylose into FUR in an aqueous–organic biphasic batch reaction setup. 31 A round-bottomed glass pressure reactor fitted with a Teflon screw-top was charged with xylose (2.00 g), aq. HCl (20 mL, 20.2%), and a magnetic bead.…”

Section: Methodsmentioning

confidence: 99%

Renewable synthesis of γ-butyrolactone from biomass-derived 2-furanone using palladium supported on humin-derived activated carbon (Pd/HAC) as a heterogeneous catalyst

Vinod

Dutta

2023

RSC Adv.

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Section: Methodsmentioning

confidence: 99%

Renewable synthesis of γ-butyrolactone from biomass-derived 2-furanone using palladium supported on humin-derived activated carbon (Pd/HAC) as a heterogeneous catalyst

Vinod

Dutta

2023

RSC Adv.

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“…Glucose as a starting feedstock delivers lower yields than those with fructose using the same catalyst (HCl) and DCE extraction phase. This reduction is attributed to the initial isomerisation of glucose to fructose monomers that must occur before subsequent dehydration steps can occur, with reported yields of 64%, 17%, and 38% [55][56][57].…”

Section: Cmf Production From Sugar Monomers and Dimersmentioning

confidence: 99%

Production and Synthetic Possibilities of 5-Chloromethylfurfural as Alternative Biobased Furan

Soukup-Carne,

Bragagnolo,

Soleo Funari

et al. 2024

Catalysts

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As fossil-based resource depletion intensifies and the use of lignocellulosic biomass gains more and more momentum for the development of biorefineries, the production of furans has received a great deal of attention considering their outstanding synthetic possibilities. The production of 5-hydroxymethylfurfural (HMF) is quite established in the recent scientific literature, with a large number of studies having been published in the last few years. Lately, there has been a growing interest in the synthesis of 5-chloromethylfurfural (CMF) as a novel building block of similar molecular structure to that of HMF. CMF has some advantages, such as its production taking place at milder reaction conditions, a lower polarity that enables easier separation with the aid of organic media, and the presence of chlorine as a better leaving group in synthesis. Precisely the latter aspect has given rise to several interesting products to be obtained therefrom, including 2,5-dimethylfuran, 2,5-furandicarboxylic acid, and 5-methylfurfural, to name a few. This work covers the most relevant aspects related to the production of CMF and an array of synthetic possibilities. Through varied catalysts and reaction conditions, value-added products can be obtained from this chemical, thus highlighting the advances in the production and use of this chemical in recent years.

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“…17,18 Some variations of the process have been reported, such as the addition of CrCl 3 /ZnCl 2 as a metal catalyst, 19 the use of microwave heating, 20 and the addition of benzyl tributyl ammonium as a phase transfer catalyst. 21 Nevertheless, the use of concentrated HCl can be problematic due to its high corrosiveness and possible health issues if inhaled or spilled. As an alternative, other studies have reported blends of metal chlorides as part of eutectic solvents for the synthesis of 5-CMF from glucose and starch, 22 showing that these are effective both for the isomerization of glucose and for the halogenation of 5-HMF together with choline chloride.…”

Section: Introductionmentioning

confidence: 99%

“…However, only a few studies focusing on the synthesis of 5-CMF have been published and most of them are limited to the use of concentrated HCl for its preparation, as proposed by Mascal and co-workers. , Some variations of the process have been reported, such as the addition of CrCl 3 /ZnCl 2 as a metal catalyst, the use of microwave heating, and the addition of benzyl tributyl ammonium as a phase transfer catalyst . Nevertheless, the use of concentrated HCl can be problematic due to its high corrosiveness and possible health issues if inhaled or spilled.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Conversion of Starch into 5-Chloromethylfurfural and 5-Hydroxymethylfurfural in a Low-Transition Temperature Mixture

Lecona-Vargas,

Pandey,

Orsat

et al. 2024

Ind. Eng. Chem. Res.

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The synthesis of platform molecules from food wastes is a topic of interest for the development of sustainable biorefineries. Starchy food wastes can serve as feedstocks to produce fine chemicals, fuels, and polymers by the hydrolysis of starch and further conversion into platform molecules such as 5-hydroxymethylfurfural (5-HMF) and 5-chloromethylfurfural (5-CMF). Conventionally, the synthesis of 5-CMF has relied on the use of concentrated hydrochloric acid (HCl) as a catalyst. However, recent studies have explored alternative methods, including eutectic solvents containing metal chlorides, which have facilitated 5-CMF production. This study presents a novel approach to synthesizing 5-CMF from starch using eutectic solvents without the need for either HCl or metal chloride additives. The synthesis was conducted using a low transition temperature mixture of choline chloride, citric acid, and boric acid in a biphasic system with dichloromethane as the extracting solvent. The synthesis was optimized using the response surface methodology through a Box−Behnken design. At 100 °C and 90 min of reaction time, up to 17 mol % 5-HMF and 13 mol % 5-CMF were produced, and in the optimized conditions of 120 °C and 135 min, up to 33 mol % 5-CMF with less than 1 mol % 5-HMF was obtained from starch. Moreover, it was shown that the low transition temperature mixture used in this study could be reused at least five times.

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Hydrochloric acid-catalyzed coproduction of furfural and 5-(chloromethyl)furfural assisted by a phase transfer catalyst

Cited by 9 publications

References 31 publications

Renewable synthesis of γ-butyrolactone from biomass-derived 2-furanone using palladium supported on humin-derived activated carbon (Pd/HAC) as a heterogeneous catalyst

Renewable synthesis of γ-butyrolactone from biomass-derived 2-furanone using palladium supported on humin-derived activated carbon (Pd/HAC) as a heterogeneous catalyst

Production and Synthetic Possibilities of 5-Chloromethylfurfural as Alternative Biobased Furan

One-Pot Conversion of Starch into 5-Chloromethylfurfural and 5-Hydroxymethylfurfural in a Low-Transition Temperature Mixture

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