Upgraded production of (1R,5S)-1-hydroxy-3,6-dioxa-bicyclo[3.2.1]octan-2-one from cellulose catalytic pyrolysis and its detection in bio-oils by spectroscopic methods

Mancini, Ines; Dosi, Federico; Defant, Andrea; Crea, Fucsia; Miotello, A.

doi:10.1016/j.jaap.2014.09.014

Cited by 13 publications

(12 citation statements)

References 19 publications

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“…The identification of LAC was firstly reported by Furneaux and co‐workers after pyrolysis of cellulose in the presence of chlorides of Fe, Al, Zn, Ni, Co Mn, Sn . This study remained silent for almost twenty years, when the enhanced production of LAC from the catalytic pyrolysis of cellulose was confirmed in a variety of conditions . A few years ago it was reported that zeolite catalysts reduce the yields of anhydrosugars, while all nanopowder oxides, with the exception of silicon oxide, provide higher yields of LAC …”

Section: Introductionmentioning

confidence: 95%

“…who observed that metal‐based nanoparticles, especially Zn and Co, promoted the formation of LAC over levoglucosan in the pyrolysis of eucalyptus at 500 °C . Mesoporous phases of the MCM‐41 type doped with Sn or other metals were found to enhance the yields of LAC . The clay montmorillonite K10 was found to catalyze the production of LAC.…”

Section: Introductionmentioning

confidence: 99%

“…The clay montmorillonite K10 was found to catalyze the production of LAC. Even if the yields are lower with respect to Sn‐MCM‐41 and nanopowder aluminium titanate, montomorillonite has the advantage of being more economical and environmentally sustainable . However, the most substantial yields of LAC in the pyrolysis of cellulose did not reach 10 % (8.6±0.7 with aluminium titanate nanoparticles at 350 °C) .…”

Section: Introductionmentioning

confidence: 99%

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The Reaction Pathway of Cellulose Pyrolysis to a Multifunctional Chiral Building Block: The Role of Water Unveiled by a DFT Computational Investigation

et al. 2016

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LAC (hydroxylactone (1R,5S)-1-hydroxy-3,6-dioxabicyclo[3.2.1]octan-2-one) is one of the most interesting products of the pyrolysis of cellulose and represents a useful chiral building block in organic synthesis. A computational investigation at the DFT level on the mechanism of formation of LAC shows that this species can be obtained following two reaction paths, path A and path B, starting from a well-known pyrolysis product (ascopyrone P). A series of internal rearrangements involving in all cases a proton transfer leads directly to LAC (path B). An alternative path (path A) can be also followed. From this path, via a "gate" connecting the two reaction channels, it is possible to reach path B and form LAC. In both cases, the rate-determining step of the process is the initial keto-enol isomerization. We found that water, which is present in the reaction mixture, "catalyzes" the reaction by assisting the proton transfers present in all the steps of the process. In particular, water lowers the barrier of the rate-determining step that becomes 40.9 kcal mol (79.4 kcal mol in the absence of water). The corresponding computed rate constant is 4.3×10 s at 500 °C, a value which is consistent with the presence of LAC in the absence of metal catalysts. The results of this study on the non-catalyzed process underpin the important role played by water in the formation of pyrolysis products of cellulose where proton transfer is a key mechanistic step.

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Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Reaction Pathway of Cellulose Pyrolysis to a Multifunctional Chiral Building Block: The Role of Water Unveiled by a DFT Computational Investigation

et al. 2016

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“…Therefore, renewable energy sources should be extensively explored to discover alternatives to gasoline and diesel [6,7]. For instance, biomass includes fauna and flora, and biomass resources, such as animal wastes, agricultural crops, short-rotation herbaceous crops, aquatic plants, energy crops, wood, and other biomaterials, are considered potential fuel sources for global production [8][9][10][11][12][13]. In contrast to fossil fuels, biomass-derived fuels can be developed as future fuel sources because they can be produced within a short period and they can provide environmentally friendly benefits [14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Progress on upgrading methods of bio-oil: A review

Lian

Xue

Zhao

et al. 2017

Int. J. Energy Res.

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Summary Bio‐oil is a promising alternative energy source to crude oil for broad application prospects. Bio‐oil can help us avoid over‐reliance on petroleum resources and significantly reduce pollutants and greenhouse gas emissions, improve environment conditions, and protect ecological systems. However, bio‐oil applications have been impeded because of limited technologies, and poor bio‐oil quality has posed a great challenge. As such, considerable research efforts have been made for realizing its potential application value. Scientific and technical advancements on methods of bio‐oil quality improvement to date are reviewed, with an emphasis on advantages and disadvantages of each method. It also points out barriers and gives some recommendations to enhance bio‐oil combustion performance in the future. Copyright © 2017 John Wiley & Sons, Ltd.

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“…Furthermore, Rutkowski (2012) found that the montmorillonite K-10 catalyst also possessed a certain ability to promote LAC formation. Recently, Mancini et al (2014) performed the catalytic pyrolysis of cellulose, using the previously reported catalysts (Sn-MCM-41, montmorillonite K-10, and nanopowder aluminium titanate) to produce LAC-rich bio-oils and then quantitatively determined the LAC yields using 1 H NMR and FT-IR techniques. The highest LAC yield was 7.6 wt.%, obtained using the Sn-MCM-41 catalyst.…”

Section: Introductionmentioning

confidence: 99%

Selective Analytical Production of 1-Hydroxy-3,6-dioxabicyclo[3.2.1]octan-2-one from Catalytic Fast Pyrolysis of Cellulose with Zinc-Aluminium Layered Double Oxide Catalyst

Zhang¹,

Lü²,

Ye³

et al. 2015

BioResources

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Zinc-aluminium layered double oxide (Zn-Al-LDO) catalysts derived from layered double hydroxides (LDHs) were prepared and used for the catalytic fast pyrolysis of cellulose to selectively produce 1-hydroxy-3,6-dioxabicyclo[3.2.1]octan-2-one (LAC), which is a valuable anhydrosugar derivative. Analytical pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) experiments were performed to investigate the LAC production under different reaction conditions. The results indicated that the Zn-Al-LDO catalysts were capable of greatly inhibiting the pyrolytic formation of levoglucosan (LG) and capable of promoting the formation of LAC and certain other products. The catalyst with the Zn/Al molar ratio of 2 exhibited the best catalytic capacity for LAC production. Both pyrolysis temperature and the catalyst-to-cellulose ratio affected the pyrolytic product distribution remarkably. The maximal LAC yield was obtained at the pyrolysis temperature of 350 °C and catalyst-to-cellulose ratio of 4 and featured a peak area percentage of 21.9% (calculated by GC/MS), compared with only 3.0% from the non-catalytic process. In addition, the LDO catalyst performed better than the previously reported montmorillonite K-10 catalyst on the enhancement of LAC production.

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Upgraded production of (1R,5S)-1-hydroxy-3,6-dioxa-bicyclo[3.2.1]octan-2-one from cellulose catalytic pyrolysis and its detection in bio-oils by spectroscopic methods

Cited by 13 publications

References 19 publications

The Reaction Pathway of Cellulose Pyrolysis to a Multifunctional Chiral Building Block: The Role of Water Unveiled by a DFT Computational Investigation

The Reaction Pathway of Cellulose Pyrolysis to a Multifunctional Chiral Building Block: The Role of Water Unveiled by a DFT Computational Investigation

Progress on upgrading methods of bio-oil: A review

Selective Analytical Production of 1-Hydroxy-3,6-dioxabicyclo[3.2.1]octan-2-one from Catalytic Fast Pyrolysis of Cellulose with Zinc-Aluminium Layered Double Oxide Catalyst

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