Acid-Catalyzed Conversion of Cellulose Into Levulinic Acid With Biphasic Solvent System

Ma, Changyue; Cai, Bo; Zhang, Le; Feng, Junfeng; Pan, Hui

doi:10.3389/fpls.2021.630807

Cited by 12 publications

(7 citation statements)

References 55 publications

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“…30−32 On the other hand, formic acid and LA can be obtained by the chemo-catalytic deconstruction of cellulosic biomass. 33 The formate and levulinate esters of HMF, namely, 3a (Table 1, entry 1) and 3e (Table 1, entry 5), were obtained in 86 and 88% yields, respectively. Stearic acid and oleic acid, obtained from triglycerides in oils and fats, 34 are used for synthesizing 3o (Table 1, entry 15) and 3p (Table 1, entry 16), respectively.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Some of the HMF-esters reported in this work are biorenewable in their entirety. For example, AcOH and propionic acid employed to synthesize 3b and 3c , respectively, can be produced from biomass via an enzymatic pathway. − On the other hand, formic acid and LA can be obtained by the chemo-catalytic deconstruction of cellulosic biomass . The formate and levulinate esters of HMF, namely, 3a (Table , entry 1) and 3e (Table , entry 5), were obtained in 86 and 88% yields, respectively.…”

Section: Resultsmentioning

confidence: 99%

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Efficient Synthesis of 5-(Hydroxymethyl)furfural Esters from Polymeric Carbohydrates Using 5-(Chloromethyl)furfural as a Reactive Intermediate

Bhat

Hegde

Dutta

et al. 2022

ACS Sustainable Chem. Eng.

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This work reports an efficient, gram-scale synthesis of 5-(hydroxymethyl)furfural (HMF) esters using biomassderived 5-(chloromethyl)furfural (CMF) as a reactive intermediate. The HMF-esters have potential applications as chemical intermediates, fuel additives, and bioactive compounds. Initially, CMF was prepared in good yields directly from polymeric carbohydrates (starch, inulin, and cellulose) and cellulosic materials (cotton and filter paper) using a biphasic batch reaction system, consisting of aqueous hydrochloric acid and 1,2-dichloroethane. The use of ZnCl 2 as an additive allowed the reaction to proceed under milder conditions while significantly improving the isolated yield of CMF. The effects of reaction temperature, reaction time, extracting solvent, and ZnCl 2 loading on CMF yield were investigated. Microcrystalline cellulose was converted into CMF with a 72% isolated yield under optimized reaction conditions (80 °C, 2 h). After that, CMF was transformed into various novel esters of HMF in excellent isolated yields (>85%) by reacting with a slight excess amount of the triethylammonium salt of various alkyl/aryl carboxylic acids under solvent-free conditions.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of 5-(Hydroxymethyl)furfural Esters from Polymeric Carbohydrates Using 5-(Chloromethyl)furfural as a Reactive Intermediate

Bhat

Hegde

Dutta

et al. 2022

ACS Sustainable Chem. Eng.

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“…The reaction time is an important parameter to improve the process productivity . In several cases, prolonged reaction time leads to formation of undesired side products . Thus, to examine the effect of reaction time on the rice straw conversion and LA yield, experiments were conducted with variable reaction time from 30 to 180 min.…”

Section: Resultsmentioning

confidence: 99%

PolyE-IL, an Efficient and Recyclable Bronsted Acid Catalyst for Conversion of Rice Straw into Levulinic and Other Organic Acids

Ukarde

Pawar

2022

Energy Fuels

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The lignocellulosic biomass has been identified as a potential renewable feedstock for production of levulinic acid (LA). In the present study, the catalytic thermo liquefaction (CTL) process for liquefaction of rice straw into LA was studied by integrating the polyethyleneimine functionalized acidic ionic liquid (PolyE-IL) catalyst. The screening of various PolyE-IL catalysts with variable counter ions showed the remarkable formation of carbohydrates, LA, formic acid, and acetic acid (AA). Among the tested PolyE-IL catalysts, PolyE-IL with a [HSO4]− counter ion showed the maximum conversion efficiency. The process intensification study to evaluate the influence of reaction parameters such as catalyst concentration, reaction temperature, time, and slurry concentrations was conducted to achieve the maximum conversion and yield of organic acids. Moreover, the influence of feedstock pretreatment was also studied. The pretreated rice straw provided maximum yields of LA and FA. The intensified CTL process for untreated rice straw resulted in 49.8% LA, 50.5% FA, and 100% AA, while CTL of pretreated rice straw resulted in 65.5% LA, 75.8% FA, and 26.7% AA of the theoretical maximum at 210 °C for 120 min. The separation of the catalyst and other liquefaction products was achieved using adsorption followed by membrane separation processes. The adsorption process leads to separation of the undesired polymeric side products, while membrane separation provides efficient separation of the catalyst and organic acids with >98% efficiency. The undesired side products separated in the adsorption process were concentrated as CTL-Oil and characterized for physiochemical properties. CTL-Oil is C-, H-, and O-rich feedstock with a caloric value of 24–26 MJ/Kg and thus could be explored for multiple fuel and energy applications. Thus, an efficient valorization of rice straw was achieved using a recyclable, robust, and efficient catalyst.

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“…In recent years, researchers are constantly developing new heterogeneous catalytic technologies to produce levulinic acid from cellulose by introducing suitable solvent system to improve the interaction between cellulose and the solid acid catalyst, and tuning pore structure and acid sites (Ma et al 2021;Sun et al 2018a).…”

Section: Dehydrationmentioning

confidence: 99%

Heterogeneous strategies for selective conversion of lignocellulosic polysaccharides

et al. 2022

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Lignocellulosic biomass is the most abundant renewable carbon resource on earth, for which many efforts have been made to convert it using various chemocatalytic processes. Heterogeneously chemocatalytic conversion conducted based on reusable solid catalysts is the process with the greatest potential studied presently. This review provides insights into the representative achievements in the research area of heterogeneous chemical catalysis technologies for the production of value-added chemicals from lignocellulosic polysaccharides (cellulose and hemicellulose). Popular approaches for the conversion of lignocellulosic polysaccharides into chemicals, including hydrolyzation (glucose, xylose 2 and arabinose), dehydration (5-hydroxymethylfurfuran, furfural and levulinic acid), hydrogenation/hydrogenolysis (sorbitol, mannitol, xylitol, 1,2-propylene glycol, ethlyene glycol and ethanol), selective oxidation (gluconic acid and lactic acid), have been comprehensively reviewed.However, technological barriers still exist, which have to be overcome to further integrate hydrolysis with the refinery processes based on multifunctional solid catalysts, and convert ligncellulosic polysaccharides into value-added fine chemicals. In general, the approaches and technologies are discussed and critically evaluated in terms of the possibilities and potential for further industrial implementation.

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Acid-Catalyzed Conversion of Cellulose Into Levulinic Acid With Biphasic Solvent System

Cited by 12 publications

References 55 publications

Efficient Synthesis of 5-(Hydroxymethyl)furfural Esters from Polymeric Carbohydrates Using 5-(Chloromethyl)furfural as a Reactive Intermediate

Efficient Synthesis of 5-(Hydroxymethyl)furfural Esters from Polymeric Carbohydrates Using 5-(Chloromethyl)furfural as a Reactive Intermediate

PolyE-IL, an Efficient and Recyclable Bronsted Acid Catalyst for Conversion of Rice Straw into Levulinic and Other Organic Acids

Heterogeneous strategies for selective conversion of lignocellulosic polysaccharides

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