1708-42-5Relevant articles and documents
A Solvent-Free Method for Making Dioxolane and Dioxane from the Biorenewables Glycerol and Furfural Catalyzed by Oxorhenium(V) Oxazoline
Wegenhart, Benjamin L.,Abu-Omar, Mahdi M.
, p. 4741 - 4743 (2010)
Low catalyst loading of a cationic oxorhenium(V) oxazoline complex, [2-(2'-hydroxyphenyl)-2-oxazolinato(-2)]oxorhenium(v), condenses diols and aldehydes to give 1,3-dioxolanes in excellent yields under neat conditions and reasonably mild temperatures. The reaction is applicable to biomass-derived furfural and glycerol. The resulting cyclic acetals may find use as value-added chemicals and/or oxygenate fuel additives. Differences in the stereoselectivity of the reaction for epoxides versus diols provide insight into the reaction mechanism.
Investigation in the area of furan acetal compounds. 13. Synthesis and structure of 1,3-dioxacyclanes based on furfural and glycerol
Gromachevskaya,Kvitkovsky,Usova,Kulnevich
, p. 979 - 985 (2004)
The optimum conditions were found for the condensation of glycerol with furfural. It was shown that the reaction of glycerol with furfural gives a mixture of the cis and trans isomers of five- and six-membered furan 1,3-dioxacyclanes. The cis- and trans-5-hydroxy-2-furyl-1,3-dioxanes were isolated by column chromatography, and their stereochemical structure was established by IR and NMR spectroscopy.
Modified boehmite: A choice of catalyst for the selective conversion of glycerol to five-membered dioxolane
Barik, Manas,Chinnaraja, Eswaran,Dabas, Shilpa,Mishra, Jyotiranjan,Subramanian, Palani S.,Subramanian, Saravanan
, p. 695 - 703 (2022/01/22)
The choice of the active site and support matrix decides the activity of a catalyst. Any modifications on these will have a significant impact on the reactivity and selectivity of the catalyst. Here, we have synthesised WO3-loaded boehmite and applied it for the acetalization of a biomass-derived bulk chemical, glycerol. The well-characterized acid catalyst exhibits a selective acetalization of glycerol with good conversions into a five-membered dioxolane product. The cyclability of the catalyst up to six times along with the retention of the catalytic activity ensures the heterogeneity of the material.
A green approach for the preparation of a surfactant embedded sulfonated carbon catalyst towards glycerol acetalization reactions
Auroux, Aline,Chowdhury, Biswajit,Das, Avik,Ghosh, Anindya,Sen, Debasis,Singha, Aniruddha
, p. 4827 - 4844 (2020/08/21)
The green synthesis of heterogeneous catalysts often requires a solid-state reaction pathway. In this work, a cationic surfactant (CTAB) embedded sulfonated carbon catalyst was prepared via a sustainable route with the aim of having controlled surface hydrophobicity and acidity for glycerol acetalization reactions. The main objective of this study was to tune the hydrophobicity and acidic site density, either via adding a cationic surfactant or changing the carbon to sulphur ratio. The as-synthesized catalyst was characterized via XRD, N2 adsorption/desorption, SAXS, FESEM, FTIR, pyridine-IR, high-temperature DR-FTIR, TGA, 13C-NMR, Raman, and XPS techniques. The incorporation of a cationic surfactant (CTAB) reduces the surface area but increases the acidic site density to a greater extent. The bonding between the surfactant (CTAB) and surface hydroxyl groups was elucidated via XPS analysis. DR-FTIR studies implied that the -SO3H groups are strongly bonded to the carbon network, while the lower amount of water mass loss seen from TGA studies showed the substantial improvement in surface hydrophobicity after modification with the surfactant. Moreover, the combination of acidic site density and hydrophobicity played a key role in attaining around 90% glycerol conversion and 98% solketal selectivity under ambient conditions. Notably, characterization of the used catalyst revealed that the loss of activity is mainly related to a drop in hydrophobicity, which occurs due to the loss of surfactant during washing with methanol.
Graphene-promoted acetalisation of glycerol under acid-free conditions
Oger, Nicolas,Lin, Yuting F.,Le Grognec, Erwan,Rataboul, Franck,Felpin, Fran?ois-Xavier
, p. 1531 - 1537 (2016/04/04)
Serendipity led us to unveil unexpected and uncovered properties of graphene for the acetalisation of glycerol with both aldehydes and ketones, furnishing an acid-free process for fuel bio-additive candidates. Mechanistic studies ruled out the intervention of residual acidic species or metallic cations at the surface of graphene, and therefore, the peculiar electronic properties of graphene are most probably responsible for this unforeseen reactivity. Recycling studies revealed the robustness of graphene under the experimental conditions since only a marginal erosion of the reaction yield was observed after six cycles.
