Mechanism insight into the fast pyrolysis of xylose, xylobiose and xylan by combined theoretical and experimental approaches

Hu, Bin; Lü, Qiang; Zhang, Zhenxi; Wu, Yuting; Li, Kai; Chen, Dong; Yang, Yongping

doi:10.1016/j.combustflame.2019.04.052

Cited by 45 publications

(47 citation statements)

References 32 publications

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“…The last glycosidic bond cleavage investigated involves a ring contraction as mentioned in ref 12,13 . These reactions (TS3 and TS6) involve a complex bicyclic transition state (Scheme 5).…”

Section: Primary Decomposition Of the Mid-chains Ofmentioning

confidence: 99%

“…It is worth noting that the presence of the glycosidic bond in the model molecule is mandatory because it can prevent reactions in the acyclic part. For instance, Hu et al 12 studied the decomposition of xylose and put forward a 5-membered cyclization reaction involving a H-atom shift from the hydroxyl group located on carbon atom #4. At the B3LYP-D3 level of theory, this reaction has a low activation energy of 145.2 kJ mol -1 .…”

Section: Thermal Decomposition Of the Primary Fragmentsmentioning

confidence: 99%

“…In particular, the formation of furfural is often presented in the literature 7, 8, 12, 29 by a sequence of reactions involving successive dehydrations. Moreover, Hu et al 12 experimentally detected furfural, during the fast pyrolysis of xylose and xylobiose, while only smaller amount has been observed with xylan. In our study, furfural formation can be represented by the following reactions (Scheme 15): Scheme 15.…”

Section: Thermal Decomposition Of the Primary Fragmentsmentioning

confidence: 99%

“…All these reactions lead to fragments 1 or 15, already encountered, as well as light species such as prop-2-ene-1,2-diol, glyceraldehyde (C 3 H 6 O 3 ) and its tautomer, the dehydroglycerol (pro-1-ene-1,2,3-triol). Glyceraldehyde has been reported in many flash pyrolysis of xylan or hemicellulose 3,9,12 . However, this species can easily react by a retro-aldol reaction (TS44) to form ethenediol and formaldehyde.…”

Section: Thermal Decomposition Of the Primary Fragmentsmentioning

confidence: 99%

“…In addition, they proposed reaction 2 pathways, based on DFT calculations (M06-2X/def2tzvp//B3LYP/6-31G(d,p)), to explain the main products formed during the pyrolysis of xylose, xylobiose and 4-O-methylglucuronic acid groups. In the same way, Hu et al 12 performed an experimental and theoretical study on the fast pyrolysis of xylose, xylobiose and xylan (from birch wood). Experiments were performed by using a pyroprobe pyrolyser coupled to a GC-MS. At 400°C, hydroxyacetaldehyde (HAA), furfural (FF), dianhydro xylose (DAX) and 1,4-anhydro-D-xylopyranose (ADX) are the main products identified from xylose and xylobiose while for xylan, the predominant products are: HAA, hydroxyacetone (HA), 1-hydroxy-2butanone (HB), and in a lesser extent, furfural.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Theoretical study of the pyrolysis of β-1,4-xylan: a detailed investigation on unimolecular concerted reactions

Goussougli

Sirjean

Glaude

et al. 2021

Phys. Chem. Chem. Phys.

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Section: Primary Decomposition Of the Mid-chains Ofmentioning

confidence: 99%

Section: Thermal Decomposition Of the Primary Fragmentsmentioning

confidence: 99%

Section: Thermal Decomposition Of the Primary Fragmentsmentioning

confidence: 99%

Section: Thermal Decomposition Of the Primary Fragmentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Theoretical study of the pyrolysis of β-1,4-xylan: a detailed investigation on unimolecular concerted reactions

Goussougli

Sirjean

Glaude

et al. 2021

Phys. Chem. Chem. Phys.

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Interaction mechanism between cellulose and hemicellulose during the hydrothermal carbonization of lignocellulosic biomass

Jia

Wang

Chen

et al. 2022

Energy Science & Engineering

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The fuel properties of the solid product obtained from hydrothermal carbonization (HTC) are substantially influenced by the interaction reactions of the lignocellulose components. This study focused on the interaction reactions of cellulose and hemicellulose (represented by glucose and xylose, respectively) and the formation mechanism of the hydrochar through experiments and density functional theory methods. Results indicated that furfural was the main intermediate product of xylose and then converted into benzenes, which were seldom produced from the hydrothermal conversion of glucose. When glucose and xylose were co-carbonized hydrothermally, more benzenes were generated because glucose and xylose exhibited a synergistic effect in forming alkenes, which were then cracked remarkably into C 2 H 2 . Furthermore, C 2 H 2 reacted with furan that transformed from furfural and formed benzenes. The aqueous product of co-HTC also contained a high concentration of 5-hydroxymethylfurfural (5-HMF). The 5-HMF could polymerize with benzenes and furfural to form insoluble furan−benzene polymers, gradually aggregating into organic micronucleus. Subsequently, 5-HMF, furfural, and benzenes in the aqueous phase were immobilized on the surface of the organic micronucleus through surface binding sites, eventually causing the growth of organic micronucleus into hydrochar particles. The polymerization between furan−benzene polymers could also increase the aromatization degree of the hydrochar, thereby enhancing the energy density of the hydrochar.

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Characterization of the degradation products of lignocellulosic biomass by using tandem mass spectrometry experiments, model compounds, and quantum chemical calculations

Guthrie

Rowell

Anyaeche

et al. 2023

Mass Spectrometry Reviews

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Biomass‐derived degraded lignin and cellulose serve as possible alternatives to fossil fuels for energy and chemical resources. Fast pyrolysis of lignocellulosic biomass generates bio‐oil that needs further refinement. However, as pyrolysis causes massive degradation to lignin and cellulose, this process produces very complex mixtures. The same applies to degradation methods other than fast pyrolysis. The ability to identify the degradation products of lignocellulosic biomass is of great importance to be able to optimize methodologies for the conversion of these mixtures to transportation fuels and valuable chemicals. Studies utilizing tandem mass spectrometry have provided invaluable, molecular‐level information regarding the identities of compounds in degraded biomass. This review focuses on the molecular‐level characterization of fast pyrolysis and other degradation products of lignin and cellulose via tandem mass spectrometry based on collision‐activated dissociation (CAD). Many studies discussed here used model compounds to better understand both the ionization chemistry of the degradation products of lignin and cellulose and their ions' CAD reactions in mass spectrometers to develop methods for the structural characterization of the degradation products of lignocellulosic biomass. Further, model compound studies were also carried out to delineate the mechanisms of the fast pyrolysis reactions of lignocellulosic biomass. The above knowledge was used to assign likely structures to many degradation products of lignocellulosic biomass.

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Mechanism insight into the fast pyrolysis of xylose, xylobiose and xylan by combined theoretical and experimental approaches

Cited by 45 publications

References 32 publications

Theoretical study of the pyrolysis of β-1,4-xylan: a detailed investigation on unimolecular concerted reactions

Theoretical study of the pyrolysis of β-1,4-xylan: a detailed investigation on unimolecular concerted reactions

Interaction mechanism between cellulose and hemicellulose during the hydrothermal carbonization of lignocellulosic biomass

Characterization of the degradation products of lignocellulosic biomass by using tandem mass spectrometry experiments, model compounds, and quantum chemical calculations

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