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Tailored production of lignin-containing cellulose nanofibrils from sugarcane bagasse pretreated by acid-catalyzed alcohol solutions.
Carbohydr Polym
September 2022
School of Mechanical, Medical and Process Engineering, Faculty of Engineering, Queensland University of Technology, 2 George St, Brisbane, Queensland 4000, Australia; Centre for Agriculture and the Bioeconomy, Faculty of Science, Queensland University of Technology, 2 George St, Brisbane, Queensland 4000, Australia. Electronic address:
Article Synopsis
- The study explored the effects of acid-catalyzed alcohol pretreatment on sugarcane bagasse for producing lignin-containing cellulose nanofibrils (LCNF) with customized properties.
- AG-LCNF had the highest lignin content but low hydrophobicity, while AE-LCNF had lower lignin content but higher hydrophobicity, highlighting the influence of the pretreatment solvent.
- NMR analyses demonstrated how alcohols modify lignin, impacting LCNF properties and their potential applications in polymer composites and emulsions.
Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.
J Org Chem
March 2022
Department of Chemistry and Biochemistry, School of Green Chemistry and Engineering, The University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, United States.
We disclose here practical strategies toward the synthesis of morpholines and Claisen rearrangement products based on the divergent reactivity of a common halonium intermediate. These reactions employ widely available alkenes in a Lewis acid-catalyzed halo-etherification process that can then transform them into the desired products with exceptional regioselectivity for both activated and unactivated olefins. Our mechanistic probe reveals an interesting regiochemical kinetic resolution process.
View Article and Find Full Text PDFEvolution Process and Controlled Synthesis of Humins with 5-Hydroxymethylfurfural (HMF) as Model Molecule.
ChemSusChem
February 2020
Dalian University of Technology, Dalian, 116024, P.R. China.
Elucidation of the chemical structure and formation mechanism of humins is a requisite to further improve the efficiency of acid-catalyzed biomass conversion. Through a low-temperature approach, the key intermediates resulting in the formation of 5-hydroxymethylfurfural (HMF)-derived humins were captured, revealing multiple elementary reactions such as etherification, esterification, aldol condensation, and acetalization. Through humin characterization, it was found out that the aldol condensation moiety between aldehyde group and levulinic acid is critical to justify the characteristic IR peaks (1620 and 1710 cm ) and aromatic fragments from pyrolysis GC-MS.
View Article and Find Full Text PDFOrganocatalytic Reductive Propargylation: Scope and Applications.
J Org Chem
December 2019
Catalysis Laboratory, School of Chemistry , University of Hyderabad, Hyderabad 500 046 , India.
An amino acid-catalyzed three-component reductive coupling protocol has been developed for the selective high-yielding synthesis of nearly fifty examples of propargylated cyclic/acyclic systems from the various propargyl aldehydes, cyclic/acyclic CH acids, and Hantzsch ester under ambient conditions. It is an economical, efficient, catalytic, metal-free protocol for the quick gram-scale synthesis of propargylated cyclic/acyclic compounds, and many of these coupling compounds were purified by a simple precipitation-filtration technique instead of column chromatography. Functionally rich propargylated cyclic-1,3-diketones were specifically transformed into dihydropyrans found in natural products and drugs through an annulative etherification reaction by using Lewis-acid (AgOTf) catalysis.
View Article and Find Full Text PDFSelective synthesis of spirooxindoles via a two-step reaction of N-phenacylpyridinium bromide, 1,3-indanedione and N-alkylisations.
Org Biomol Chem
April 2019
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
The three-component reaction of 1,3-indanedione and N-alkylisatins with two molecular N-phenacylpyridinium salts in dry acetonitrile in the presence of triethylamine resulted in unique functionalized spiro[indoline-3,4'-naphtho[1,2-b]furan] derivatives in good yields, which were successfully converted to spiro[indoline-3,2'-naphthalen]-4'-yl acetate derivatives by acylation with acetyl chloride in methylene dichloride and alkoxy-substituted spiro[benzo[h]chromene-5,3'-indolines] by acid-catalyzed etherification reaction in alcohol. The reaction mechanism involved the sequential cycloaddition of the in situ-generated pyridinium ylide to dipolarophilic enone, ring-opening of 1,3-indanedione, and selective annulation.
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