Zr-DBS with Sulfonic Group: A Green and Highly Efficient Catalyst for Alcoholysis of Furfuryl Alcohol to Ethyl Levulinate

Li, Xiaoning; Li, Yehui; Wang, Xiang; Peng, Qingrui; Hui, Wei; Hu, Anzhong; Wang, Haijun

doi:10.1007/s10562-020-03516-1

Cited by 10 publications

(3 citation statements)

References 44 publications

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“…According to previous studies, 21 the mechanism of DES catalysis of the alcoholysis of FA to form EL is proposed, as shown in Scheme 1 . In DES and 5-SSA, the reaction starts with the hydroxyl group on the FA connecting to the acid center in the solution.…”

Section: Resultsmentioning

confidence: 99%

Alcoholysis of Furfuryl Alcohol to Ethyl Levulinate Catalyzed by a Deep Eutectic Solvent

Wang

Ding

2022

ACS Omega

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In this study, the alcoholysis of furfuryl alcohol (FA) into ethyl levulinate (EL) using a deep eutectic solvent (DES) composed of choline chloride (ChCl) and ethanol was investigated by experiments and calculations. Experimental results reveal that the addition of 5-sulfonic acid salicylic acid (5-SSA) can catalyze the alcoholysis of FA to produce EL. The combined presence of ChCl and 5-SSA significantly improved the selectivity for EL. The mechanism of the alcoholysis of FA to EL in acidic DES was investigated by density functional theory (DFT) calculations in Gaussian 03. It was found that hydrogen-bond acceptor ChCl is coupled with hydrogen-bond donor ethanol to form a structure similar to HCl and ethoxy, which facilitates the alcoholysis of FA into EL.

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Section: Resultsmentioning

confidence: 99%

Alcoholysis of Furfuryl Alcohol to Ethyl Levulinate Catalyzed by a Deep Eutectic Solvent

Wang

Ding

2022

ACS Omega

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“…The sulfonic acid-based solid catalysts usually contain high acidity. For example, Wang et al synthesized Zr-DBS solid catalyst containing a sulfonic group with sodium dodecyl benzene sulfonate and ZrOCl 2 , which was used for the alcoholysis of FA to EL (95.27% yield) [21]. Guo et al reported an aminosulfonated carbon and evaluated the alcoholysis/esterification properties of FA and LA [9].…”

Section: Introductionmentioning

confidence: 99%

Lignin-Derived Ternary Polymeric Carbon as a Green Catalyst for Ethyl Levulinate Upgrading from Fructose

Liu

Luo

et al. 2022

Catalysts

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Currently, the utilization of lignocellulose mainly focuses on the conversion of polysaccharide components to value-added chemicals, such as ethyl levulinate (EL). Lignin is an important component of lignocellulosic biomass that is often neglected. Herein, ternary polymeric carbon (TPC–S) was synthesized by polymerization of mixed monomers (4-methylphenol, 4-ethylphenol, and 4-propylphenol) derived from lignin and subsequent sulfonation, which was used as a heterogeneous catalyst for the transformation of fructose to EL. Through a series of characterization methods, it was illustrated that the prepared catalyst had a layered porous structure. The calculated carbon layer spacing is 0.413 nm, and the average pore size is 5.1 nm. This structure greatly increases the specific surface area (165.2 m2/g) of the catalyst, which makes it possible to introduce more –SO3H species in the process of sulfonation, thus furnishing EL with increased yield. The effects of reaction temperature, time, catalyst dosage, and fructose initial concentration on the production of EL were investigated. It was found that 70.3% EL yield was detected at 130 °C for 10 h. In addition, the catalyst had good stability and could obtain 65.6% yield of EL in the fourth cycle. The obtained catalyst has the advantages of low cost, easy preparation, and high catalytic efficiency, which is expected to achieve efficient utilization of lignin and provide a potential solution for the future production of EL.

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“…Initial studies focused on the use of homogeneous catalysts such as strong mineral acids or metal salts. [26] However, the difficult product separation, catalyst toxicity, and reaction container corrosion led to the exploitation of heterogeneous catalysts, including acidic ion exchange resins [27][28][29], zeolites [30][31][32], (sulfated) zirconia-based catalysts [33][34][35], (supported) heteropolyacids [36][37][38][39], activated carbon [40][41][42], functionalized organosilica materials [43][44][45][46][47][48], ionic liquids [49,50], and several sulfonic acid functionalized materials [51][52][53][54]. Some studies were also conducted employing continuous-flow apparatus [32,44] or microwave-assisted procedures [26,42].…”

Section: Introductionmentioning

confidence: 99%

Alkyl Levulinates from Furfuryl Alcohol Using CT151 Purolite as Heterogenous Catalyst: Optimization, Purification, and Recycling

Annatelli

Trapasso

Lena

et al. 2021

Sustainable Chemistry

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Commercially available Purolite CT151 demonstrated to be an efficient acid catalyst for the synthesis of alkyl levulinates via alcoholysis of furfuryl alcohol (FA) at mild temperatures (80–120 °C) and short reaction time (5 h). Reaction conditions were first optimized for the synthesis of ethyl levulinate and then tested for the preparation of methyl-, propyl-, isopropyl-, butyl, sec-butyl- and allyl levulinate. Preliminary scale-up tests were carried out for most of the alkyl levulinates (starting from 5.0 g of FA) and the resulting products were isolated as pure by distillation in good yields (up to 63%). Furthermore, recycling experiments, conducted for the preparation of ethyl levulinate, showed that both the Purolite CT151 and the exceeding ethanol can be recovered and reused for four consecutive runs without any noticeable loss in the catalyst activity.

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Zr-DBS with Sulfonic Group: A Green and Highly Efficient Catalyst for Alcoholysis of Furfuryl Alcohol to Ethyl Levulinate

Cited by 10 publications

References 44 publications

Alcoholysis of Furfuryl Alcohol to Ethyl Levulinate Catalyzed by a Deep Eutectic Solvent

Alcoholysis of Furfuryl Alcohol to Ethyl Levulinate Catalyzed by a Deep Eutectic Solvent

Lignin-Derived Ternary Polymeric Carbon as a Green Catalyst for Ethyl Levulinate Upgrading from Fructose

Alkyl Levulinates from Furfuryl Alcohol Using CT151 Purolite as Heterogenous Catalyst: Optimization, Purification, and Recycling

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