37112-31-5Relevant articles and documents
Catalytic dehydration of levoglucosan to levoglucosenone using Br?nsted solid acid catalysts in tetrahydrofuran
Oyola-Rivera, Oscar,He, Jiayue,Huber, George W.,Dumesic, James A.,Cardona-Martínez, Nelson
, p. 4988 - 4999 (2019)
We studied the production of levoglucosenone (LGO) via levoglucosan (LGA) dehydration using Br?nsted solid acid catalysts in tetrahydrofuran (THF). The use of propylsulfonic acid functionalized silica catalysts increased the production of LGO by a factor of two compared to the use of homogeneous acid catalysts. We obtained LGO selectivities of up to 59% at 100% LGA conversion using solid Br?nsted acid catalysts. Water produced during the reaction promotes the solvation of the acid proton reducing the activity and the LGO production. Using solid acid catalysts functionalized with propylsulfonic acid reduces this effect. The hydrophilicity of the catalyst surface seems to have an effect on reducing the interaction of water with the acid site, improving the catalyst stability.
Leather-Promoted Transformation of Glucose into 5-Hydroxymethylfurfural and Levoglucosenone
Bobbink, Felix D.,Huang, Zhangjun,Menoud, Florent,Dyson, Paul J.
, p. 1437 - 1442 (2019)
The search for efficient catalysts frequently leads to new homogeneous and heterogeneous catalysts of increasing complexity, and sometimes common, natural, or hybrid natural/synthetic materials that could be used in catalysis are overlooked. For example, the leather industry has produced robust Cr-containing materials for centuries by chemical treatment of animal hides with chromium salts. Herein, the use of chromium-tanned leather as a heterogeneous catalyst for glucose dehydration to 5-hydroxymethylfurfural (5-HMF) and levoglucosenone (LGO) is reported. Four pieces of waste leather were obtained from shoe soles and a belt, characterized by a range of techniques including FTIR spectroscopy, SEM, BET surface area measurements, XRD, and X-ray photoelectron spectroscopy, and their catalytic activity was evaluated. The activity of the scrap leather pieces compares favorably to those of many recently reported catalysts for the preparation of 5-HMF, but additionally results in significant quantities of LGO. Overall, the results demonstrate that waste leather is an outstanding material for use in catalysis.
Production of levoglucosenone and 5-hydroxymethylfurfural from cellulose in polar aprotic solvent-water mixtures
He, Jiayue,Liu, Mingjie,Huang, Kefeng,Walker, Theodore W.,Maravelias, Christos T.,Dumesic, James A.,Huber, George W.
, p. 3642 - 3653 (2017)
We demonstrate a process to produce levoglucosenone (LGO) and 5-hydroxymethylfurfural (HMF) from cellulose in up to 65% carbon yield using sulfuric acid as catalyst and a solvent consisting of a mixture of tetrahydrofuran (THF) with water. In pure THF, LGO is the major product of cellulose dehydration, passing through levoglucosan as an intermediate. Increasing the water content (up to 5 wt%) results in HMF as the major product. HMF is formed both by glucose dehydration and direct dehydration of LGA. The maximum combined yield of LGO and HMF (～65 carbon%) is achieved in the presence of 1-2.5 wt% H2O, such that comparable amounts of these two co-products are formed. THF gave the highest total yields of LGO and HMF among the solvents investigated in this study (i.e., THF, diglyme, tetraglyme, gamma-valerolactone (GVL), cyclopentyl methyl ether (CPME), 1,4-dioxane, and dimethyl sulfoxide (DMSO)). Furthermore, the rate of LGO and HMF degradation in THF was lower than in the other solvents. LGO/HMF yields increased with increased strength of the acid catalyst (H2SO4 > H3PO4 > HCOOH), and HMF was produced more selectively than LGO in the presence of hydrochloric acid. Techno-economic analysis for LGO and HMF production from cellulose shows that the lowest LGO/HMF production costs are less than $3.00 per kg and occur at a cellulose loading and water content of 2-3% and 1.5-2.5% respectively.
