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Keywords = 5-acetoxymethyl-2-furfural (AMF)

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13 pages, 4611 KiB  
Article
Eco-Friendly Catalytic Synthesis of Top Value Chemicals from Valorization of Cellulose Waste
by Onofrio Losito, Michele Casiello, Caterina Fusco, Helena Mateos Cuadrado, Antonio Monopoli, Angelo Nacci and Lucia D’Accolti
Polymers 2023, 15(6), 1501; https://doi.org/10.3390/polym15061501 - 17 Mar 2023
Cited by 4 | Viewed by 2481
Abstract
The total amount of cellulose from paper, wood, food, and other human activity waste produced in the EU is in the order of 900 million tons per year. This resource represents a sizable opportunity to produce renewable chemicals and energy. This paper reports, [...] Read more.
The total amount of cellulose from paper, wood, food, and other human activity waste produced in the EU is in the order of 900 million tons per year. This resource represents a sizable opportunity to produce renewable chemicals and energy. This paper reports, unprecedently in the literature, the usage of four different urban wastes such as cigarette butts, sanitary pant diapers, newspapers, and soybean peels as cellulose fonts to produce valuable industrial intermediates such as levulinic acid (LA), 5-acetoxymethyl-2-furaldehyde (AMF), 5-(hydroxymethyl)furfural (HMF), and furfural. The process is accomplished by the hydrothermal treatment of cellulosic waste using both Brønsted and Lewis acid catalysts such as CH3COOH (2.5–5.7 M), H3PO4 (15%), and Sc(OTf)3 (20% w:w), thus obtaining HMF (22%), AMF (38%), LA (25–46%), and furfural (22%) with good selectivity and under relatively mild conditions (T = 200 °C, time = 2 h). These final products can be employed in several chemical sectors, for example, as solvents, fuels, and for new materials as a monomer precursor. The characterization of matrices was accomplished by FTIR and LCSM analyses, demonstrating the influence of morphology on reactivity. The low e-factor values and the easy scale up render this protocol suitable for industrial applications. Full article
(This article belongs to the Special Issue Bioresource-Derived Composites for Diverse Applications)
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11 pages, 988 KiB  
Article
Step-by-Step Hybrid Conversion of Glucose to 5-acetoxymethyl-2-furfural Using Immobilized Enzymes and Cation Exchange Resin
by Kyung Won Lee, Jin Ku Cho, Chulhwan Park and Baek-Jin Kim
Processes 2022, 10(10), 2086; https://doi.org/10.3390/pr10102086 - 14 Oct 2022
Cited by 3 | Viewed by 2370
Abstract
An alternative to 5-hydroxymethyl-2-furfural (HMF), which is a promising furan derivative that can be used as a starting material for the preparation of non-petroleum-derived polymeric materials from sugars, is 5-acetoxymethyl-2-furfural (AMF). The less-hydrophilic acetyl group of AMF has advantages over the hydroxy group [...] Read more.
An alternative to 5-hydroxymethyl-2-furfural (HMF), which is a promising furan derivative that can be used as a starting material for the preparation of non-petroleum-derived polymeric materials from sugars, is 5-acetoxymethyl-2-furfural (AMF). The less-hydrophilic acetyl group of AMF has advantages over the hydroxy group of HMF in terms of thermal stability and isolation. In previous studies, fructose has been used as a starting material along with lipases for the enzymatic synthesis of AMF. In this study, we designed a hybrid synthesis system that includes the isomerization and esterification of glucose into AMF. For the step-by-step conversion of glucose to 1,6-diacetylfructose (DAF), glucose-isomerase and immobilized lipase (Novozym 435) were used as enzymes. Furthermore, for the synthesis of AMF, the direct dehydration of DAF was performed using a cation exchange resin (Amberlyst 15), combined with several industrial solvents, such as dimethylsulfoxide (DMSO), acetonitrile (AN) and dimethylformamide (DMF) for the synthesis of AMF. In order to improve the final yield of AMF, we determined the best solvent conditions. While the AMF yield after the direct dehydration of DAF in a single solvent was maximum 24%, an AMF and HMF yield in the mixed solvent such as dioxane and DMS (9:1) was achieved each 65% and 15%. According to these results, we found that the addition of dioxane in aprotic polar solvents could affect the dehydration reaction and dramatically improve the formation of AMF and HMF. Full article
(This article belongs to the Special Issue Bioprocess Design and Optimization)
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15 pages, 1671 KiB  
Article
Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin
by Nhan Thanh Thien Huynh, Kyung Won Lee, Jin Ku Cho, Yong Jin Kim, Se Won Bae, Jong Shik Shin and Seunghan Shin
Molecules 2019, 24(24), 4623; https://doi.org/10.3390/molecules24244623 - 17 Dec 2019
Cited by 7 | Viewed by 4016
Abstract
5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while soluble H2SO [...] Read more.
5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while soluble H2SO4 was found to be the best acidic catalyst (yielding 86.6% AMF), we opted to utilize heterogeneous cation exchange resin (Amberlyst 15) together with recyclable industrial solvents (1,4-dioxane) for a more sustainable AMF synthesis procedure. Although the total yield of AMF was a little lower, both the enzyme and the solid acid catalyst could be recycled for five cycles without a significant loss of activity, which has a major contribution to the cost-efficient aspect of the entire process. Full article
(This article belongs to the Section Natural Products Chemistry)
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