Synthesis of amides and esters containing furan rings under microwave-assisted conditions

2021 ◽  
Vol 19 (1) ◽  
pp. 265-280
Author(s):  
Łukasz Janczewski ◽  
Dariusz Zieliński ◽  
Beata Kolesińska
Keyword(s):  
Furfuryl Alcohol ◽  
Flash Chromatography ◽  
Effective Coupling ◽  
Coupling Reagents ◽  
Microwave Assisted ◽  
Microwave Reactor ◽  
Amide Derivatives ◽  
Ester Moiety ◽  
Novel Method ◽  
Furandicarboxylic Acid

Abstract In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO− or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl)furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5-dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furandicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.

scholarly journals Microwave-assisted protocol for squalene isolation and conversion from oil-deodoriser distillates

2019 ◽  
Vol 8 (1) ◽  
pp. 856-864
Author(s):  
Fabio Bucciol ◽  
Gertraud Scholz ◽  
Hans Jürgen Scholz ◽  
Giancarlo Cravotto
Keyword(s):  
Fatty Acid Methyl Esters ◽  
Low Cost ◽  
Methyl Esters ◽  
Flash Chromatography ◽  
Production Chain ◽  
Silica Column ◽  
Microwave Assisted ◽  
Microwave Reactor ◽  
Acid Methyl ◽  
Solvent Free Conditions

Abstract Aiming to design a green and efficient protocol for squalane production from low-cost biomasses, a practical and scalable procedure for squalene extraction and hydrogenation to squalane is presented herein. The oil-deodoriser distillates that are produced by the vegetal-oil production chain are a renewable and cheap source of squalene. We were able to isolate an enriched fraction containing 89.0% of pure squalene (yield 55.4%) from a matrix containing about 2% squalene. Efficient microwave- assisted esterification under heterogeneous catalysis enabled the separation of fatty-acid methyl esters (FAME) via vacuum distillation. The residue was purified by flash-chromatography on a C-18 silica column using MeOH/H2O/2-propanol as the mobile phase. Finally, squalene was hydrogenated to the more stable squalane in a pressure-resistant microwave reactor. The reaction was performed over a Pd/C catalyst in EtOH, and even in solvent-free conditions, and was optimised using commercial squalene (5 bar of H2 at 100°C for 1 h).

scholarly journals Microwave-assisted catalytic upgrading of bio-based furfuryl alcohol to alkyl levulinate over commercial non-metal activated carbon

2020 ◽  
Vol 480 ◽  
pp. 110630 ◽  
Author(s):  
Yantao Wang ◽  
Deyang Zhao ◽  
Konstantinos S. Triantafyllidis ◽  
Weiyi Ouyang ◽  
Rafael Luque ◽  
...  
Keyword(s):  
Activated Carbon ◽  
Furfuryl Alcohol ◽  
Catalytic Upgrading ◽  
Microwave Assisted ◽  
Alkyl Levulinate

scholarly journals Back Cover: Microwave-Assisted Selective Hydrogenation of Furfural to Furfuryl Alcohol Employing a Green and Noble Metal-Free Copper Catalyst (ChemSusChem 24/2016)

ChemSusChem ◽  
2016 ◽  
Vol 9 (24) ◽  
pp. 3528-3528 ◽  
Author(s):  
Pedro N. Romano ◽  
João M. A. R. de Almeida ◽  
Yuri Carvalho ◽  
Peter Priecel ◽  
Eduardo Falabella Sousa-Aguiar ◽  
...  
Keyword(s):  
Noble Metal ◽  
Selective Hydrogenation ◽  
Furfuryl Alcohol ◽  
Copper Catalyst ◽  
Metal Free ◽  
Back Cover ◽  
Microwave Assisted

scholarly journals Sonochemical preparation of alumina-spheres loaded with Pd nanoparticles for 2-butyne-1,4-diol semi-hydrogenation in a continuous flow microwave reactor

RSC Advances ◽  
2018 ◽  
Vol 8 (13) ◽  
pp. 7029-7039 ◽  
Author(s):  
Emanuela Calcio Gaudino ◽  
Maela Manzoli ◽  
Diego Carnaroglio ◽  
Zhilin Wu ◽  
Giorgio Grillo ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Continuous Flow ◽  
Flow Reactor ◽  
Pd Nanoparticles ◽  
Microwave Assisted ◽  
Continuous Flow Reactor ◽  
Microwave Reactor

A novel protocol for microwave-assisted alkyne semi-hydrogenation under heterogeneous catalysis in a continuous flow reactor is reported herein.

scholarly journals Further applications of classical amide coupling reagents: Microwave-assisted esterification on solid phase

2018 ◽  
Vol 24 (8-9) ◽  
pp. e3111 ◽  
Author(s):  
Risa Takayama ◽  
Shun Hayakawa ◽  
Hiroshi Hinou ◽  
Fernando Albericio ◽  
Fayna Garcia-Martin
Keyword(s):  
Solid Phase ◽  
Coupling Reagents ◽  
Microwave Assisted ◽  
Amide Coupling

Comparison of Conventional and Microwave Heating for Evaluation of Microwave Effects

2016 ◽  
Vol 69 (8) ◽  
pp. 865 ◽  
Author(s):  
Péter Bana ◽  
István Greiner
Keyword(s):  
Temperature Measurement ◽  
Microwave Heating ◽  
Organic Synthesis ◽  
Convenient Method ◽  
Thermal Effects ◽  
Fibre Optic ◽  
Organic Transformations ◽  
Microwave Assisted ◽  
Microwave Reactor ◽  
Microwave Effects

In microwave-assisted organic synthesis, the question of microwave effects is still debated. Proper examination of these hypothesized phenomena is encumbered by some specific features of microwave heating. We devise a convenient method to eliminate most of the irreproducibility observed in microwave-heated organic transformations by thermal conditioning of the microwave reactor cavity. To show the utility of this approach, we investigated a reaction of 2-chloropyridine, in which microwave conditions were shown to be beneficial by previous studies. Using our method to ensure proper reproducibility together with fibre optic temperature measurement, the observed differences were traced back to large hidden thermal differences, while non-thermal effects could not be detected in the comparison experiments.

Microwave-Assisted Preparation and Physical Characterisation of Iron Oxyhydroxides Adsorbents for Arsenic Removal from Aqueous Solutions

2013 ◽  
Vol 634-638 ◽  
pp. 249-253 ◽  
Author(s):  
Meng Nan Lu ◽  
Aleksandar N. Nikoloski ◽  
Pritam Singh ◽  
Dale Parsonage ◽  
Radhanath Prasad Das ◽  
...  
Keyword(s):  
Adsorption Process ◽  
Arsenic Removal ◽  
Degree Of Crystallinity ◽  
Batch Adsorption ◽  
Microwave Assisted ◽  
Bet Analysis ◽  
Novel Method ◽  
The Degree Of Crystallinity ◽  
Adsorptive Properties

A novel method for preparation of iron oxyhydroxide materials, involving aqueous precipitation followed by microwave assisted aging is investigated. The produced materials are characterized by XRD, SEM, EDX and TEM spectroscopy and BET analysis. The materials show physical characteristics dependent on preparation procedure. The adsorptive properties of the materials for arsenic are studied by batch adsorption techniques. It is found that the rate of arsenic upload depends strongly on the degree of crystallinity of the materials. The adsorption capacity is approximately 55 mg/g. The physical characterization of the arsenic loaded adsorbents show that the adsorption process modifies the morphology of the materials. Over 4% of arsenic atoms are incorporated into the particle matrix.

Sign in / Sign up

Export Citation Format

Share Document