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Theoretical Elucidation of beta-O-4 Bond Cleavage of Lignin Model Compound Promoted by Sulfonic Acid-Functionalized Ionic Liquid
Zhang, Yaqin; Huo, Feng; Wang, Yanlei; Xia, Yu; Tan, Xin; Zhang, Suojiang; He, Hongyan
2019-02-15
Source PublicationFRONTIERS IN CHEMISTRY
ISSN2296-2646
Volume7Pages:11
AbstractWhile the depolymerization of lignin to chemicals catalyzed by ionic liquids has attracted significant attention, the relevant molecular mechanism, especially the cleavage of specific bonds related to efficient depolymerization, still needs to be deeply understood for the complexity of this natural aromatic polymer. This work presents a detailed understanding of the cleavage of the most abundant beta-O-4 bond in the model system, guaiacylglycerol beta-guaiacyl ether, by a Bronsted acidic IL (1-methyl-3-(propyl-3-sulfonate) imidazolium bisulfate ([C(3)SO(3)Hmim][HSO4]) using density functional theory calculation and molecular dynamics simulation. It has been found that [C(3)SO(3)Hmim][HSO4] generates zwitterion/H2SO4 via proton transfer with an energy barrier of 0.38 kcal/mol, which plays a dominant role in the lignin depolymerization process. Subsequently, the reaction can be carried out via three potential pathways, including (1) the dehydration of alpha-C-OH, (2) dehydration of gamma-C-OH, and (3) the protonation beta-O. The electrophilic attack of H2SO4 and the hydrogen-bonding interaction between GG and zwitterion are the two most important factors to promote the depolymerization reaction. In all steps, the dehydration of alpha-C-OH route is computed to be favored for the experiment. The relatively higher energy barrier for beta-O-4 bond dissociation among these reaction steps is attributed to the hindrance of the self-assembled clusters of GG in the mixed system. Further, the dense distribution of H13([C(3)SO(3)Hmimi) surrounding O21(GG), indicated by sharp peaks in RDFs, reveals that -SO3H in cations plays a substantial role in solvating lignin. Hopefully, this work will demonstrate new insights into lignin depolymerization by functionalized ILs in biomass conversion chemistry.
Keywordlignin ionic liquid DFT molecular dynamics beta-O-4 bond reaction mechanism
DOI10.3389/fchem.2019.00078
Language英语
WOS KeywordLIGNOCELLULOSIC BIOMASS ; MOLECULAR-DYNAMICS ; FORCE-FIELD ; DEPOLYMERIZATION ; CONVERSION ; EFFICIENT ; CELLULOSE ; MECHANISM ; CATALYST ; DFT
Funding ProjectNational Natural Science Foundation of China[21406230] ; National Natural Science Foundation of China[21736003] ; National Natural Science Foundation of China[2176278] ; Beijing Natural Science Foundation[2182068] ; Youth Innovation Promotion Association of CAS[2017066]
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
Funding OrganizationNational Natural Science Foundation of China ; Beijing Natural Science Foundation ; Youth Innovation Promotion Association of CAS
WOS IDWOS:000458772100001
PublisherFRONTIERS MEDIA SA
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/27978
Collection中国科学院过程工程研究所
Corresponding AuthorHe, Hongyan
AffiliationChinese Acad Sci, Inst Proc Engn, Beijing Key Lab Ion Liquids Clean Proc, CAS Key Lab Green Proc & Engn,State Key Lab Multi, Beijing, Peoples R China
Recommended Citation
GB/T 7714
Zhang, Yaqin,Huo, Feng,Wang, Yanlei,et al. Theoretical Elucidation of beta-O-4 Bond Cleavage of Lignin Model Compound Promoted by Sulfonic Acid-Functionalized Ionic Liquid[J]. FRONTIERS IN CHEMISTRY,2019,7:11.
APA Zhang, Yaqin.,Huo, Feng.,Wang, Yanlei.,Xia, Yu.,Tan, Xin.,...&He, Hongyan.(2019).Theoretical Elucidation of beta-O-4 Bond Cleavage of Lignin Model Compound Promoted by Sulfonic Acid-Functionalized Ionic Liquid.FRONTIERS IN CHEMISTRY,7,11.
MLA Zhang, Yaqin,et al."Theoretical Elucidation of beta-O-4 Bond Cleavage of Lignin Model Compound Promoted by Sulfonic Acid-Functionalized Ionic Liquid".FRONTIERS IN CHEMISTRY 7(2019):11.
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