A comparison of the pyrolysis behavior of selected β-O-4 type lignin model compounds

Jiang, Weikun; Wu, Shubin; Lucia, Lucian A.; Chu, Jiangyong

doi:10.1016/j.jaap.2017.04.003

Cited by 43 publications

(24 citation statements)

References 27 publications

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“…In addition, radical 30 formed from C β –O bond homolytic mechanism can also combine with free H radical and undergo H-abstraction to form product 2 (2-methoxyphenol) [ 20 , 23 , 30 ]. It agrees with the results obtained by He et al [ 22 ] and Jiang et al [ 31 ]. They conducted pyrolysis experiments on a β- O -4 type lignin dimer model compound (guaiacylglycerol-β-guaiacyl ether) which has same functional groups on the alkyl side chain and aromatic ring near the ether bond.…”

Section: Resultssupporting

confidence: 93%

“…Pyrolysis of PPE may follow mechanisms 1, 2 and 11 to decompose, and their competitiveness is in the order of mechanism 2 > mechanism 1 > mechanism 11. α-OH-PPE may undergo pyrolysis reactions through mechanisms 1, 2, 4, 5, 6 and 11, and their competitiveness follows the order of mechanism 2 > mechanism 1 > mechanism 4 > mechanism 11 > mechanism 5 > mechanism 6. β-CH 2 OH-PPE may follow five pyrolysis mechanisms to decompose, whose competitiveness order is mechanism 2 > mechanism 1 > mechanism 7 > mechanism 8 > mechanism 11. o -CH 3 O-PPE also has five possible pyrolysis mehanisms with the competitiveness order of mechanism 2 > mechanism 3 > mechanism 1 > mechanism 10 > mechanism 11. It is important to note that the major pyrolytic products of the four model compounds obtained through DFT calculations shown in the Supplementary Materials agree well with the experimental results [ 18 , 19 , 29 , 31 ], which futher confirms the validity of the pyrolysis model. Based on the results, a similar conclusion can be drawn that most of the concerted mechanisms are prior to homolytic mechanisms, except for mechanism 6.…”

Section: Resultssupporting

confidence: 80%

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A Comprehensive Study on Pyrolysis Mechanism of Substituted β-O-4 Type Lignin Dimers

Jiang

Lü

et al. 2017

IJMS

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In order to understand the pyrolysis mechanism of β-O-4 type lignin dimers, a pyrolysis model is proposed which considers the effects of functional groups (hydroxyl, hydroxymethyl and methoxyl) on the alkyl side chain and aromatic ring. Furthermore, five specific β-O-4 type lignin dimer model compounds are selected to investigate their integrated pyrolysis mechanism by density functional theory (DFT) methods, to further understand and verify the proposed pyrolysis model. The results indicate that a total of 11 pyrolysis mechanisms, including both concerted mechanisms and homolytic mechanisms, might occur for the initial pyrolysis of the β-O-4 type lignin dimers. Concerted mechanisms are predominant as compared with homolytic mechanisms throughout unimolecular decomposition pathways. The competitiveness of the eleven pyrolysis mechanisms are revealed via different model compounds, and the proposed pyrolysis model is ranked in full consideration of functional groups effects. The proposed pyrolysis model can provide a theoretical basis to predict the reaction pathways and products during the pyrolysis process of β-O-4 type lignin dimers.

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Section: Resultssupporting

confidence: 93%

Section: Resultssupporting

confidence: 80%

A Comprehensive Study on Pyrolysis Mechanism of Substituted β-O-4 Type Lignin Dimers

Jiang

Lü

et al. 2017

IJMS

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“…PEV, as a polyester with a β–hydrogen to the ester bond is expected to degrade in a similar manner, but it has a peculiarity; it contains an ether bond in para position to the ester group that is expected to result in a complex degradation mechanism because of the presence of two characteristic groups on its structure. Polymers based on vanillic acid are expected to share common features in their degradation mechanism with woody biomass, which involves homolysis, mainly of the C-O bond, and concerted routes [73,74,75,76,77]. Ethers and subsequently polyethers degrade through radical processes with mechanisms that include homolytic cleavage, disproportionation and abstraction of the formed radicals [78,79].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Thermal Properties and Decomposition Mechanism of Poly(Ethylene Vanillate) Polyester

et al. 2019

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Plastics are perceived as modern and versatile materials, but their use is linked to numerous environmental issues as their production is based on finite raw materials (petroleum or natural gas). Additionally, their low biodegradability results in the accumulation of microplastics. As a result, there is extensive interest in the production of new, environmentally friendly, bio-based and biodegradable polymers. In this context, poly(ethylene vanillate) (PEV) has a great potential as a potentially bio-based alternative to poly(ethylene terephthalate); however, it has not yet been extensively studied. In the present work, the preparation of PEV is reported. The enthalpy and the entropy of fusion of the pure crystalline PEV have been estimated for the first time. Additionally, the equilibrium melting temperature has also been calculated. Furthermore, the isothermal and non-isothermal crystallization behavior are reported in detail, and new insights on the thermal stability and degradation mechanism of PEV are given.

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“…Cleavage of intermolecular linkages in lignin is crucial for the pyrolysis of lignin. Four typical β-O-4 lignin dimer [42] compounds with different substituents at the C α and C β positions ( Figure 2) were synthesized and used to investigate the effect of the substituent group on chemical reactions during lignin pyrolysis. The cleavage of intermolecular linkages dominated reactions during pyrolysis below 300 • C. The presence of the CH 2 OH group at the C β position greatly inhibited the formation of volatile products and promoted char formation.…”

Section: Effect Of Biomass Composition On Bio-oil Propertiesmentioning

confidence: 99%

“…x FOR PEER REVIEW 6 of Molecular structures of four β-O-4 lignin dimer structures with different substituents at the Cα and Cβ positions, reproduced with permission from[42], Copyright Elsevier, 2018.…”

mentioning

confidence: 99%

Catalytic Pyrolysis of Biomass and Polymer Wastes

et al. 2018

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Oil produced by the pyrolysis of biomass and co-pyrolysis of biomass with waste synthetic polymers has significant potential as a substitute for fossil fuels. However, the relatively poor properties found in pyrolysis oil—such as high oxygen content, low caloric value, and physicochemical instability—hampers its practical utilization as a commercial petroleum fuel replacement or additive. This review focuses on pyrolysis catalyst design, impact of using real waste feedstocks, catalyst deactivation and regeneration, and optimization of product distributions to support the production of high value-added products. Co-pyrolysis of two or more feedstock materials is shown to increase oil yield, caloric value, and aromatic hydrocarbon content. In addition, the co-pyrolysis of biomass and polymer waste can contribute to a reduction in production costs, expand waste disposal options, and reduce environmental impacts. Several promising options for catalytic pyrolysis to become industrially viable are also discussed.

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A comparison of the pyrolysis behavior of selected β-O-4 type lignin model compounds

Cited by 43 publications

References 27 publications

A Comprehensive Study on Pyrolysis Mechanism of Substituted β-O-4 Type Lignin Dimers

A Comprehensive Study on Pyrolysis Mechanism of Substituted β-O-4 Type Lignin Dimers

Synthesis, Thermal Properties and Decomposition Mechanism of Poly(Ethylene Vanillate) Polyester

Catalytic Pyrolysis of Biomass and Polymer Wastes

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