Facile and high-yield synthesis of methyl levulinate from cellulose

Huang, Yao‐Bing; Yang, Tao; Lin, Yung‐Kuo; Zhu, Ying-Zhi; Li, Licheng; Pan, Hui

doi:10.1039/c7gc02883k

Cited by 85 publications

(68 citation statements)

References 54 publications

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“…Recently, many reports have been published about oxidation of biomass-derived compounds into value-added platform chemicals (Albonetti et al, 2015;Elliott et al, 2015;Huang et al, 2018;Zhang and Huber, 2018). Figure 5 shows that a wide variety of commodity platform chemicals can be produced from the catalytic oxidation of cellulose or carbohydratederived compounds.…”

Section: Oxidationmentioning

confidence: 99%

Recent Advances in Aqueous-Phase Catalytic Conversions of Biomass Platform Chemicals Over Heterogeneous Catalysts

Zhang

Wang

et al. 2020

Front. Chem.

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A series of biomass-derived platform molecules, such as glucose, furans, levulinic acid, 5-hydroxymethylfurfural, and acetic acids, can be converted into a variety of value-added chemicals through catalytic transformations that include dehydration, hydrogenation, oxidation, isomerization, reforming, ketonization, and aldol condensation over heterogeneous catalysts. Aqueous-phase processing is an important issue and a great challenge for the heterogeneous catalytic conversion of biobased chemicals due to the high water content of the biomass and the formation of water during the transformation process. In this paper, heterogeneous catalysts that are applicable to the aqueous-phase conversion process of biomass platform chemicals, including noble metal catalysts, non-noble metal catalysts, bimetallic catalysts, metal oxides, and zeolite, are introduced, and a comprehensive evaluation of the catalyst performance, including the catalytic activity, stability, and regeneration performance of different kinds of heterogeneous catalysts, are made. Besides, we highlighted the effect of water on heterogeneous catalysts and the deactivation mechanism in the aqueous phase. Beyond this, several catalytic mechanisms of aqueous-phase conversion over heterogeneous catalysts are summarized in order to help understand the reaction process on the surface of catalysts in the aqueous phase, so as to design targeted catalysts. At last, a prospect of biobased chemicals and fuels is forecasted.

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Section: Oxidationmentioning

confidence: 99%

Recent Advances in Aqueous-Phase Catalytic Conversions of Biomass Platform Chemicals Over Heterogeneous Catalysts

Zhang

Wang

et al. 2020

Front. Chem.

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“…However, use of such solvents results in a wide range of products and obtaining high yields necessarily limits . Compared with other solvents, methanol has the potential for selective depolymerization; however, it is a highly toxic solvent that should be avoided when possible …”

Section: Introductionmentioning

confidence: 99%

Rapid Depolymerization of Decrystallized Cellulose to Soluble Products via Ethanolysis under Mild Conditions

et al. 2020

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“…Cellulose is a feedstock for the production of platform chemicals such as 5-hydroxymethylfurfural (HMF), 1 levulinic acid (LA), levulinic esters or other chemicals, [2][3][4] which could be transformed into more useful chemicals via hydrogenation or other reactions. 5,6 In this process, cellulose firstly hydrolyzes to break down the macrostructure to form glucose monomers or oligomers.…”

Section: Introductionmentioning

confidence: 99%

“…16 CrCl 2 as a Lewis acid catalyst could facilitate the isomerization of glucose to fructose via a hydride transfer step. 17 Other metal chlorides have also been used for the conversion of carbohydrates, such as ZnCl 2,18 AlCl 3,19 etc. 20,21 Hu et al 22 investigated the use of SnCl 4 for the production of HMF from glucose.…”

Section: Introductionmentioning

confidence: 99%

Conversion of monosaccharides into levulinic acid/esters: impacts of metal sulfate addition and the reaction medium

Sun

Zhang

Shao

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND: Inorganic salts could be used as catalysts for the effective conversion of sugars. In this study, the impacts of various metal sulfates (Na 2 SO 4 , K 2 SO 4 , MnSO 4 , CoSO 4 , NiSO 4 , ZnSO 4 , CuSO 4 , Fe 2 (SO 4 ) 3 , La 2 (SO 4 ) 3 and Ce(SO 4 ) 2 ) on the conversion of glucose/fructose to levulinic acid in varied reaction media were evaluated. RESULTS:The sulfates strongly chelated with the sugars, preventing their dehydration reactions in the presence of sulfuric acid and leading to polymerization of the sugars. The sulfates themselves showed varied activity and selectivity for the conversion of the sugars to levulinic acid/esters or 5-hydroxymethylfurfural (HMF), depending on the coordination with the reaction medium. K 2 SO 4 or Na 2 SO 4 could catalyze the production of HMF from glucose/fructose in water, while in DMSO the yield of HMF was substantially higher. In THF, nevertheless, almost no HMF was formed, while other sulfates such as NiSO 4 in THF could effectively catalyze the conversion of fructose to HMF. In alcohols, Fe 2 (SO 4 ) 3 was the most effective sulfate for the conversion of the sugars to levulinic acid/esters, and the alcohols could effectively suppress the polymerization of the sugars. CONCLUSION:The distinct catalytic performances of the sulfates in the varied reaction media originated from their different coordination or chelation with the sugars and the reaction medium.

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Facile and high-yield synthesis of methyl levulinate from cellulose

Abstract: The production of alkyl levulinates from cellulose was successfully achieved by using a simple and efficient metal salt catalyst, Al2(SO4)3, offering a high yield up to 70.6% under microwave conditions within a short reaction time of 40 minutes.

Cited by 85 publications

References 54 publications

Recent Advances in Aqueous-Phase Catalytic Conversions of Biomass Platform Chemicals Over Heterogeneous Catalysts

Recent Advances in Aqueous-Phase Catalytic Conversions of Biomass Platform Chemicals Over Heterogeneous Catalysts

Rapid Depolymerization of Decrystallized Cellulose to Soluble Products via Ethanolysis under Mild Conditions

Conversion of monosaccharides into levulinic acid/esters: impacts of metal sulfate addition and the reaction medium

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