One-pot synthesis of levulinic acid from cellulose in ionic liquids

Shen, Yue; Sun, Jiankui; Yi, Yuxuan; Wang, Bo; Xu, Feng; Sun, Run‐Cang

doi:10.1016/j.biortech.2015.05.080

Cited by 81 publications

(28 citation statements)

References 20 publications

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“…Shen et al. showed that a 39.4 % LA yield could be achieved with the acidic IL catalyst [MIMBS]HSO 4 . In our recent work, we also demonstrated that 98.4 % of cellulose could be converted into 31.1 % butyl levulinate (BL) with the SO 3 H‐functionalized [MIMBS]HSO 4 IL catalyst .…”

Section: Introductionsupporting

confidence: 61%

“…[24] Shen et al showed that a3 9.4 %L Ay ield could be achievedw ith the acidic IL catalyst [MIMBS]HSO 4 . [25] In our recent work, we also demonstrated that 98.4 %o fc ellulose could be converted into 31.1 %b utyl levulinate (BL) with the SO 3 H-functionalized [MIMBS]HSO 4 IL catalyst. [26] However,t he yield and selectivity of the target products in the aforementioned processes shouldb eenhanced.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Conversion of Carbohydrates to Levulinate Ester over Heteropolyanion‐Based Ionic Liquids

et al. 2016

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An efficient one-pot approach for the production of levulinate ester from renewable carbohydrates is demonstrated over heteropolyanion-based ionic liquid (IL-POM) catalysts with alcohols as the promoters and solvents. The relationships between the structure, acidic strength, and solubility of the IL-POM in methanol and the catalytic performance were studied intensively. A cellulose conversion of 100 % could be achieved with a 71.4 % yield of methyl levulinate over the catalyst [PyPS] PW O [PyPS=1-(3-sulfopropyl)pyridinium] at 150 °C for 5 h. This high efficiency is ascribed to the reasonably high activity of the ionic liquid (IL) catalyst and reaction coupling with rapid in situ esterification of the generated levulinic acid with the alcohol promoter, which allows the insolubility of cellulose encountered in biomass conversion to be overcome. Furthermore, the present process exhibits high feedstock adaptability for typical carbohydrates and handy catalyst recovery by a simple self-separation procedure through temperature control.

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Section: Introductionsupporting

confidence: 61%

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of Carbohydrates to Levulinate Ester over Heteropolyanion‐Based Ionic Liquids

et al. 2016

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“…Dumont [22] with 55% LA yield from corn starch at 180ºC in 15 min, Jeong [18] with 25% LA yield from glucosamine at 188ºC in 49 min and Shen et al [23] with 39% LA yield from cellulose in 2 h. It should be noted that in the abovementioned studies the starting materials were pure carbohydrates where as in this study biomass was used as received without prior separation of carbohydrates. Thus the LA yields achieved in this study are highly comparable with the yields reported in literature.…”

Section: The Effect Of Lewis Acid Catalyst and The Reaction Time On Lmentioning

confidence: 92%

Microwave-assisted conversion of novel biomass materials into levulinic acid

Lappalainen

Vogeler

Kärkkäinen

et al. 2018

Biomass Conv. Bioref.

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Levulinic acid is considered as one the most important platform chemicals. It is currently produced mainly from lignocellulosic biomasses. However, there are also other abundant biomass materials, which could be used as raw materials for levulinic acid production. In this work levulinic acid was produced from two novel biomasses in the presence of Brønsted (H 2 SO 4) and Lewis acid (CrCl 3. 6H 2 O or AlCl 3. 6H 2 O) catalysts. The studied materials were carbohydrate-rich potato peel waste and sporocarps of the fungus Cortinarius armillatus. Reaction conditions, i.e. time, temperature, H 2 SO 4 and Lewis acid concentrations, were studied by utilizing full 2 4-factorial experimental designs. Microwave irradiation was used as the heating method. Based on the results the reaction temperature and the H 2 SO 4 concentration had the greatest impact on the yield of levulinic acid. The highest yield obtained in this study from potato peel waste was 49% with 180ºC for reaction temperature, 15 min for reaction time and 0.5 and 0.0075 M for the concentrations of H 2 SO 4 and CrCl 3 , respectively. When Cortinarius armillatus was used as the raw material the highest yield was 62% with 180ºC for reaction temperature, 40 min for reaction time and 0.5 and 0.0075 M for the concentrations of H 2 SO 4 and CrCl 3 , respectively.

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“…That many ILs fully dissolve cellulosic material under mild conditions is a primary enabler towards high yields and selectivity, although secondary reasons exist for the success of ILs in this context . Pertinent examples of successful applications of ILs include the transformation of cellulose into low‐molecular‐weight reducing sugars in 99 % yield within 1 h at 100 °C (solvents 1‐methyl‐3‐butylimidazolium chloride and triethyl‐(3‐sulfopropyl)‐ammonium hydrogen sulfate), into 5‐(hydroxymethyl)furfural (HMF) in 79 % yield within 2 h at 120 °C (solvent 1‐butyl‐3‐methylimidazolium chloride), or into levulinic acid in 40 % yield in 2 h at 120 °C (solvent 1‐(4‐sulfobutyl)‐3‐methylimidazolium hydrogen sulfate), all of which are arguably benchmark instances of the chemical processing of cellulose into target platform molecules. Drawbacks of the use of ILs include the complexity of recovery of ionic solvents and products from the reaction media, along with their high cost, and these pose potential hurdles to their widespread acceptance in industrial scale processes .…”

Section: Introductionmentioning

confidence: 99%

Acid‐Catalysed Conversion of Carbohydrates into Furan‐Type Molecules in Zinc Chloride Hydrate

2019

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Acid‐catalysed conversion of biomass, specifically cellulose, holds promise to create value‐added, renewable replacements for many petrochemical products. We investigated an unusual acid‐catalysed transformation of cellulose and cellobiose in the biphasic solvent system zinc chloride hydrate (ionic liquid)/anisole. Here, furyl hydroxymethyl ketone and furfural are obtained as major products, which are valuable but less commonly formed in high yields in transformations of cellulosic substrates. We explored this chemistry in small‐scale model reactions and applied the optimised methods to the conversion of cellulose in bench‐scale processes. The optimum reaction system and preferred reaction conditions are defined to select for highly desirable furanoid products in the highest known yields (up to 46 %) directly from cellulose or cellobiose. The method avoids the use of added catalysts: the ionic solvent zinc chloride hydrate possesses the intrinsic acidity required for the hydrolysis and chemical transformation steps. The process involves inexpensive media for the catalytic conversion of cellulose into high‐value products under mild processing conditions.

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One-pot synthesis of levulinic acid from cellulose in ionic liquids

Cited by 81 publications

References 20 publications

Catalytic Conversion of Carbohydrates to Levulinate Ester over Heteropolyanion‐Based Ionic Liquids

Catalytic Conversion of Carbohydrates to Levulinate Ester over Heteropolyanion‐Based Ionic Liquids

Microwave-assisted conversion of novel biomass materials into levulinic acid

Acid‐Catalysed Conversion of Carbohydrates into Furan‐Type Molecules in Zinc Chloride Hydrate

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