645-67-0Relevant academic research and scientific papers
Efficient alcoholysis of furfuryl alcohol to n-butyl levulinate catalyzed by 5-sulfosalicylic acid
Zhao, Wenguang,Ding, Hui,Tian, Yi,Xu, Qiong,Liu, Xianxiang
, p. 1339 - 1345 (2021/02/26)
It is urgent to study the utilization of biomass energy to solve the environmental problems caused by the excessive use of fossil fuels. In this study, a rapid and efficient route for the conversion of furfuryl alcohol (FA) into n-butyl levulinate (BL) has been catalyzed by 5-sulfosalicylic acid. The nearly complete conversion of FA and a considerable 99.7% selectivity of BL are obtained under the optimal conditions. Based on the experimental results, a possible mechanism for the alcoholysis of FA is proposed. The present study provided a promising way for alkyl levulinates synthesis over economical and environmentally benign catalysts.
Utilization of renewable resources: Investigation on role of active sites in zeolite catalyst for transformation of furfuryl alcohol into alkyl levulinate
Vaishnavi,Sujith,Kulal, Nagendra,Manjunathan, Pandian,Shanbhag, Ganapati V.
, (2021/01/18)
A bio-derived furfuryl alcohol transformation into various high-value chemicals is a growing field of interest among researchers. This study reports an exclusive investigation of the porosity and active sites responsible for the efficient alcoholysis of furfuryl alcohol to alkyl levulinate by the aid of zeolite catalyst. Alkyl levulinate is a promising platform chemical potentially used as a fuel additive and also for the production of chemicals. A detailed study using well-characterized HZSM-5 catalyst on the influence of acidity and post synthesis modification like desilication, dealumination, metal ion exchange and phosphate modification revealed the most desired type of acid sites required to catalyze this reaction. Among the HZSM-5 catalysts tested, HZSM-5 (SAR 95) showed the best performance of ≥ 99 % furfuryl alcohol conversion and 85 % butyl levulinate selectivity under optimum conditions. The catalyst exhibited good recyclability additionally addressing all the challenges reported in the previous literature fulfilling the green chemistry principles.
Esterification of levulinic acid over Sn(II) exchanged Keggin heteropolyacid salts: An efficient route to obtain bioaditives
Da Silva, Márcio José,Chaves, Diego Morais,Teixeira, Milena Galdino,Oliveira Bruziquesi, Carlos Giovani
, (2021/03/04)
In this paper, we describe a process to add value to the biomass derivatives (i.e., levulinic acid), converting it to bioadditives over solid Sn(II) exchanged Keggin heteropolyacid salts. These solid catalysts are an attractive alternative to the traditional soluble and corrosive Br?nsted acid catalysts. Among Sn(II) heteropoly salts, the Sn1.5PW12O40 was the most active and selective catalyst, achieving high conversions (ca. 90 %) and selectivity (90–97 %) for alkyl esters and angelica lactone, the main reaction products. The impacts of the main reaction parameters (i.e., catalyst load, temperature, and the molar ratio of alcohol to acid) were investigated. The use of renewable raw material, and an efficient and recyclable catalyst are the main positive features of this process. The Sn1.5PW12O40 catalyst was easily recovered and reused without loss activity.
Encapsulation of heteropolyacids within hollow microporous polymer nanospheres for sustainable esterification reaction
He, Zhiwei,Huang, Kun,Song, Chunmei,Wang, Huaqing,Yu, Haitao,Zhang, Li
, (2021/10/25)
Herein, the Keggin structural phosphotungstic acid (HPW) has been successfully encapsulated within hollow microporous polymer nanospheres (H-MPNs) by a “ship-in-bottle” approach. The H-MPNs are formed by self-assembly induced by hyper-crosslinking of polylactide-b-polystyrene (PLA-b-PS). The obtained catalysts (HPW@H-MPNs) exhibit more sustainable availability than the previously reported HPW-supported catalysts in esterification reaction. This excellent sustainability can be attributed to the stable microporous channels in H-MPNs which are smaller than the molecular size of HPW, thereby effectively preventing the HPW from leaking out. Moreover, such catalysts also perform well in terms of catalytic activity and universality because of the combination of a hollow structure in the interior and permeable pore channels in the shells. This type of polymer carrier and general encapsulation method may provide a new strategy for developing more sustainable catalysts for various chemical reactions.
Eco-Friendly Natural Clay: Montmorillonite Modified with Nickel or Ruthenium as an Effective Catalyst in Gamma-Valerolactone Synthesis
?erveny, Libor,Trejbal, Ji?í,Vaňková, Michaela,Vrbková, Eva,Vysko?ilová, Eli?ka
, (2021/07/25)
Ni/Ru metals supported on cheap and available support montmorillonite K10 were used for the selective hydrogenation of levulinic acid to γ-valerolactone. Different loadings of the metals were applied by the impregnation method, and detailed characterization was performed (UV–VIS, XRD, TPR, TPD, particle size distribution, SEM, XRF). Metals’ homogeneous distribution on the surface was confirmed. The selectivity to the desired product was almost independent on the used material. A detailed study of the influence of solvents on the studied reaction was also performed—protic alcohol-based solvents caused the formation of levulinic and valeric acid esters in the reaction mixture. The selectivity was influenced mainly by the alcohol structure (the highest selectivity obtained using isopropyl alcohol and sec-butanol). Mainly the solvent’s donor number (except ethanol) influenced the reaction rate. The prepared catalysts are promising, available, and cheap materials for the studied reaction. Solvent may significantly influence the yield of γ-valerolactone. Graphic Abstract: [Figure not available: see fulltext.].
Method for preparing alkyl levulinate by regulating water content
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Paragraph 0054-0057, (2020/04/17)
The invention discloses a method for preparing alkyl levulinate by regulating water content. The method comprises the following steps: at least mixing furfuryl alcohol, alkyl alcohol and an acidic catalyst to form a reaction system, carrying out a reaction under the conditions of continuous stirring and reflux condensation, regulating the content of water in the reaction system to enable a mol ratio of the furfuryl alcohol to the water to be 1: (0.1-5), and carrying out aftertreatment to obtain alkyl levulinate. The structural formula of the alkyl levulinate is as shown in the specification. In the structural formula, R is any one selected from the group consisting of -CH3, -C2H5, -C3H7, -C4H9 and -C5H11. Compared with the prior art, the method provided by the invention has the advantagesthat the alkyl levulinate is prepared by regulating the water content; process is simple and feasible; conditions are mild; cost is low; few byproducts are produced; maximum yield reaches 99.8%; and the problem of low yield of alkyl levulinate in conventional synthesis methods is solved.
Carbon nanotube/PTFE as a hybrid platform for lipase B fromCandida antarcticain transformation of α-angelica lactone into alkyl levulinates
Boncel, Slawomir,Chrobok, Anna,Jurczyk, Sebastian,Kolanowska, Anna,Latos, Piotr,Szelwicka, Anna
, p. 3255 - 3264 (2020/06/17)
In this work an enzymatic method for the synthesis of alkyl levulinates from α-angelica lactone has been reported for the first time. Lipase B fromCandida antarcticawas immobilizedviainterfacial activation on the surface of a hybrid support, consisting of commercially available multi-walled carbon nanotubes (MWCNTs) and polytetrafluoroethylene (PTFE). Among the biocatalysts with various contents of PTFE in the support, the CALB/MWCNT-PTFE (0.10 wt%) biocatalyst with 22.5 wt% CALB loading was determined as the most active one in the model synthesis of then-butyl levulinate in toluene.n-Butyl levulinate was obtained quantitively after 120 min of the reaction under the selected reaction conditions (2-fold molar excess ofn-butanol, 0.150 g of biocatalyst per 1 mmol of α-angelica lactone, 20 °C). The yield ofn-butyl levulinate was found to be higher than that in the presence of accurate amounts of sulfuric acid or Novozyme-435. Additionally, the unique stability of the developed biocatalyst was demonstrated over 6 reaction cycles at 20 °C. The biocatalyst remained stable over 3 reaction cycles at 60 °C as well. The essence of the proposed approach lies in the possibility to overcome the equilibrium limitations occurring in the conventional Fisher esterification. The activity of the elaborated hybrid biocatalyst in the reactions non-specific for lipases is a clear proof of the versatility of the novel system.
Preparation method of alkyl levulinate under mild conditions
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Paragraph 0051-0052, (2020/04/01)
The invention discloses a preparation method of alkyl levulinate under mild conditions. The preparation method comprises the following steps: uniformly mixing furfuryl alcohol, alkyl alcohol and a solid catalyst, carrying out a reaction under the conditions of continuous stirring and condensation reflux, and carrying out post-treatment to obtain alkyl levulinate, wherein the alkyl levulinate has astructural formula represented by a formula I, and R is selected from any one of -CH3, -C2H5, -C3H7 and -C4H9. Compared with the method in the prior art, the preparation method of the invention is simple and easy to implement, mild in condition and few in by-product, has the yield of alkyl levulinate of up to 99.8%, can directly obtain a pure product, and solves the problem of high temperature condition required for the high yield of alkyl levulinate in the existing synthesis method.
Catalytic conversions of isocyanate to urea and glucose to levulinate esters over mesoporous α-Ti(HPO4)2·H2O in green media
Hazra Chowdhury, Arpita,Hazra Chowdhury, Ipsita,Biswas, Surajit,Chakrabortty, Pekham,Islam, Sk. Manirul
, p. 16452 - 16460 (2020/10/14)
We have described a facile solvothermal synthesis of a sheet-like α-Ti(HPO4)2·H2O nanomaterial. The material comprises 10.7 nm nanoparticles along with ordered mesopores throughout its hexagonal building blocks. The material possesses a bandgap of 3.86 eV and works as an efficient catalyst for the selective synthesis of ureas from a broad range of isocyanates in the presence of H2O at room temperature with a high product yield (up to 93%) and a TOF value up to 15.25 h-1. The α-Ti(HPO4)2·H2O nanomaterial also catalytically converts glucose to levulinic acid (LA) and subsequently LA to alkyl levulinates in the presence of different alcohols with a high product yield (up to 98%) and a TOF value up to 43.00 h-1. Furthermore, all the reactions are performed under green and facile catalytic conditions without using any hazardous solvent. The α-Ti(HPO4)2·H2O catalyst material was also found to be reusable for manifold cycles for all the reactions, keeping its catalytic efficiency along with its structural and morphological characteristics unaffected, supporting its industrial relevance.
Inexpensive and tuneable protic ionic liquids based on sulfuric acid for the biphasic synthesis of alkyl levulinates
Chrobok, Anna,Gillner, Danuta,Matuszek, Karolina,Przypis, Marta,Swad?ba-Kwa?ny, Ma?gorzata
, (2020/04/23)
Alkyl levulinates are bio-derived chemicals, increasingly popular for their uses as solvents, additives and intermediates. However, efficient and recyclable catalysts for their synthesis are still the subject of intensive research. In this study, a wide range of alkyl levulinates was synthesized under mild conditions (room temperature, atmospheric pressure), using inexpensive and efficient Br?nsted acidic ionic liquids (ILs) based on sulfuric acid and off-the-shelf bases. Acidity of the ILs was closely related to their activity. The ILs could be easy separated and recycled, without significant changes in conversion or selectivity over 10 cycles (yields ca. 90–95%). Under optimized conditions, a 99% yield of pentyl levulinate (model reaction) was achieved. The method was demonstrated to be efficient in the synthesis of levulinates of C1-C16 linear, branched and cyclic alcohols. This innovative, green route to alkyl levulinates fits well within the sustainable development strategy.
