Conversion of carbohydrate biomass to methyl levulinate with Al2(SO4)3 as a simple, cheap and efficient catalyst

Zhou, Lipeng; Zou, Haojie; Nan, Jiaxu; Wu, Lin; Yang, Xiaomei; Su, Yunlai; Lu, Tianliang; Xu, Jie

doi:10.1016/j.catcom.2014.02.021

Cited by 77 publications

(57 citation statements)

References 33 publications

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“…Analogously, a high levulinic acid yield of 67% was achieved from cellulose catalyzed by CrCl 3 in aqueous medium [27]. Al 2 (SO 4 ) 3 was highly active in the catalytic synthesis of methyl levulinate from carbohydrates in methanol, giving a 64% yield of methyl levulinate from glucose [28]. These metal salts are earth-abundant and commercially available, providing inexpensive and environmentally benign catalyst sources for biomass conversion.…”

Section: Introductionmentioning

confidence: 93%

“…The combination of Cu 2+ and Cl − can afford optimal Lewis and Brønsted acid sites for the synthesis of butyl levulinate from furfuryl alcohol conversion with unique selectivity. Although many metal salts belong to Lewis acids, the existence of metal salts as the catalysts in the reaction solution can afford Brønsted acidity derived from the hydrolysis/alcoholysis of cations, which may be related to the reaction performance [28,29,31]. Taking metal chloride as an example, the possibility of hydrolysis/alcoholysis in the reaction medium to produce active species was presumed [32,33], as illustrated in Figure 3.…”

Section: Relationship Between Reactivity and Acidity Of Reaction Systemmentioning

confidence: 99%

“…Previously, several metal salts such as Al 2 (SO 4 ) 3 [28,29], AlCl 3 [31,37], and In(OTf) 3 [38] were found to be recoverable from the reaction mixture and exhibited fine catalytic stability in multiple cycles of reuse. Herein, the recycle experiments for the selected CuCl 2 catalyst were carried out under the same reaction conditions.…”

Section: Reusability Of Cucl 2 Catalystmentioning

confidence: 99%

“…Although many metal salts belong to Lewis acids, the existence of metal salts as the catalysts in the reaction solution can afford Brønsted acidity derived from the hydrolysis/alcoholysis of cations, which may be related to the reaction performance [28,29,31]. Taking metal chloride as an example, the possibility of hydrolysis/alcoholysis in the reaction medium to produce active species was presumed [32,33], as illustrated in Figure 3 Figure 4 plots the relationship between the butyl levulinate yield (data from Figure 1) and the initial pH value of the n-butanol solution with the employed metal chlorides.…”

Section: Relationship Between Reactivity and Acidity Of Reaction Systemmentioning

confidence: 99%

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Catalytic Upgrading of Biomass-Derived Furfuryl Alcohol to Butyl Levulinate Biofuel over Common Metal Salts

Peng

Tao

2016

Catalysts

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Abstract:Levulinate ester has been identified as a promising renewable fuel additive and platform chemical. Here, the use of a wide range of common metal salts as acid catalysts for catalytic upgrading of biomass-derived furfuryl alcohol to butyl levulinate was explored by conventional heating. Both alkali and alkaline earth metal chlorides did not lead effectively to the conversion of furfuryl alcohol, while several transition metal chlorides (CrCl 3 , FeCl 3 , and CuCl 2 ) and AlCl 3 exhibited catalytic activity for the synthesis of butyl levulinate. For their sulfates (Cr(III), Fe(III), Cu(II), and Al(III)), the catalytic activity was low. The reaction performance was correlated with the Brønsted acidity of the reaction system derived from the hydrolysis/alcoholysis of cations, but was more dependent on the Lewis acidity from the metal salts. Among these investigated metal salts, CuCl 2 was found to be uniquely effective, leading to the conversion of furfuryl alcohol to butyl levulinate with an optimized yield of 95%. Moreover, CuCl 2 could be recovered efficiently from the resulting reaction mixture and remained with almost unchanged catalytic activity in multiple recycling runs.

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Section: Introductionmentioning

confidence: 93%

Section: Relationship Between Reactivity and Acidity Of Reaction Systemmentioning

confidence: 99%

Section: Reusability Of Cucl 2 Catalystmentioning

confidence: 99%

Section: Relationship Between Reactivity and Acidity Of Reaction Systemmentioning

confidence: 99%

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Catalytic Upgrading of Biomass-Derived Furfuryl Alcohol to Butyl Levulinate Biofuel over Common Metal Salts

Peng

Tao

2016

Catalysts

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“…Previously, several admirable findings on the catalytic transformation of glucose to 5-hydroxymethylfurfural (HMF) or other chemicals were presented by using metal salts such as CrCl 2 [21], AlCl 3 [22], and Al 2 (SO 4 ) 3 [23]. These metal salts are earth-abundant and commercially available, providing inexpensive and environmentally benign catalyst sources for carbohydrate conversion.…”

Section: Introductionmentioning

confidence: 99%

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

Gao

Tao

et al. 2017

Catalysts

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Abstract:The use of common metal salts as catalysts for 5-ethoxymethylfurfural (EMF) synthesis from carbohydrate transformation was performed. Initial screening suggested AlCl 3 as an efficient catalyst for EMF synthesis (45.0%) from fructose at 140 • C. Interestingly, CuSO 4 and Fe 2 (SO 4 ) 3 were found to yield comparable EMF at lower temperature of 110 to 120 • C, and high yields of ethyl levulinate (65.4-71.8%) were obtained at 150 • C. However, these sulfate salts were inactive in EMF synthesis from glucose and the major product was ethyl glucoside with around 80% yield, whereas EMF of 15.2% yield could be produced from glucose using CrCl 3 . The conversion of sucrose followed the accumulation of the reaction pathways of fructose and glucose, and a moderate yield of EMF could be achieved.

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Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass

2016

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Levulinic acid is a sustainable platform molecule that can be upgraded to valuable chemicals and fuel additives. This article focuses on the catalytic upgrading of levulinic acid into various chemicals such as levulinate esters, δ-aminolevulinic acid, succinic acid, diphenolic acid, γ-valerolactone, and γ-valerolactone derivatives such valeric esters, 5-nonanone, α-methylene-γ valerolactone, and other various molecular-weight alkanes (C9 and C18-C27 olefins).

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Conversion of carbohydrate biomass to methyl levulinate with Al2(SO4)3 as a simple, cheap and efficient catalyst

Cited by 77 publications

References 33 publications

Catalytic Upgrading of Biomass-Derived Furfuryl Alcohol to Butyl Levulinate Biofuel over Common Metal Salts

Catalytic Upgrading of Biomass-Derived Furfuryl Alcohol to Butyl Levulinate Biofuel over Common Metal Salts

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass

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