Chemical transformations of Buddleja davidii lignin during ethanol organosolv pretreatment

Bassem B. Hallac; Yunqiao Pu; Arthur J. Ragauskas

doi:10.1021/ef901556u

Chemical transformations of Buddleja davidii lignin during ethanol organosolv pretreatment

Bassem B. Hallac, Yunqiao Pu, Arthur J. Ragauskas

Research output: Contribution to journal › Article › peer-review

126 Scopus citations

Abstract

Detailed chemical structural elucidation of ethanol organosolv lignin (EOL) of Buddleja davidii was performed to determine the fundamental structure released from an ethanol organosolv pretreatment (EOP). Several nuclear magnetic resonance (NMR) techniques were used to analyze the structure of EOL, including quantitative ¹³C, ³¹P NMR, and qualitative DEPT-135 ¹³C, 2D ¹H-¹³C correlation NMR. As revealed by NMR, the aryl-O-ether linkage (β-O-4′) of lignin was extensively cleaved via homolysis during pretreatment and led to the formation of stilbene structures. Other linkages, such as resinol (β-β′) and phenylcoumaran (β-5′), were resistant to degradation. The high degree of condensation of EOL indicated that condensation reactions occurred but did not impede the delignification efficiency of EOP. Both guaiacyl and syringyl lignin were found to be reactive toward condensation during pretreatment. The results from gel-permeation chromatography showed that the degree of polymerization (DP) of lignin significantly decreased by ∼85%, facilitating lignin solubilization in ethanol.

Original language	English
Pages (from-to)	2723-2732
Number of pages	10
Journal	Energy and Fuels
Volume	24
Issue number	4
DOIs	https://doi.org/10.1021/ef901556u
State	Published - Apr 15 2010
Externally published	Yes

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title = "Chemical transformations of Buddleja davidii lignin during ethanol organosolv pretreatment",

abstract = "Detailed chemical structural elucidation of ethanol organosolv lignin (EOL) of Buddleja davidii was performed to determine the fundamental structure released from an ethanol organosolv pretreatment (EOP). Several nuclear magnetic resonance (NMR) techniques were used to analyze the structure of EOL, including quantitative 13C, 31P NMR, and qualitative DEPT-135 13C, 2D 1H-13C correlation NMR. As revealed by NMR, the aryl-O-ether linkage (β-O-4′) of lignin was extensively cleaved via homolysis during pretreatment and led to the formation of stilbene structures. Other linkages, such as resinol (β-β′) and phenylcoumaran (β-5′), were resistant to degradation. The high degree of condensation of EOL indicated that condensation reactions occurred but did not impede the delignification efficiency of EOP. Both guaiacyl and syringyl lignin were found to be reactive toward condensation during pretreatment. The results from gel-permeation chromatography showed that the degree of polymerization (DP) of lignin significantly decreased by ∼85%, facilitating lignin solubilization in ethanol.",

author = "Hallac, {Bassem B.} and Yunqiao Pu and Ragauskas, {Arthur J.}",

year = "2010",

month = apr,

day = "15",

doi = "10.1021/ef901556u",

language = "English",

volume = "24",

pages = "2723--2732",

journal = "Energy and Fuels",

issn = "0887-0624",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Chemical transformations of Buddleja davidii lignin during ethanol organosolv pretreatment

AU - Hallac, Bassem B.

AU - Pu, Yunqiao

AU - Ragauskas, Arthur J.

PY - 2010/4/15

Y1 - 2010/4/15

N2 - Detailed chemical structural elucidation of ethanol organosolv lignin (EOL) of Buddleja davidii was performed to determine the fundamental structure released from an ethanol organosolv pretreatment (EOP). Several nuclear magnetic resonance (NMR) techniques were used to analyze the structure of EOL, including quantitative 13C, 31P NMR, and qualitative DEPT-135 13C, 2D 1H-13C correlation NMR. As revealed by NMR, the aryl-O-ether linkage (β-O-4′) of lignin was extensively cleaved via homolysis during pretreatment and led to the formation of stilbene structures. Other linkages, such as resinol (β-β′) and phenylcoumaran (β-5′), were resistant to degradation. The high degree of condensation of EOL indicated that condensation reactions occurred but did not impede the delignification efficiency of EOP. Both guaiacyl and syringyl lignin were found to be reactive toward condensation during pretreatment. The results from gel-permeation chromatography showed that the degree of polymerization (DP) of lignin significantly decreased by ∼85%, facilitating lignin solubilization in ethanol.

AB - Detailed chemical structural elucidation of ethanol organosolv lignin (EOL) of Buddleja davidii was performed to determine the fundamental structure released from an ethanol organosolv pretreatment (EOP). Several nuclear magnetic resonance (NMR) techniques were used to analyze the structure of EOL, including quantitative 13C, 31P NMR, and qualitative DEPT-135 13C, 2D 1H-13C correlation NMR. As revealed by NMR, the aryl-O-ether linkage (β-O-4′) of lignin was extensively cleaved via homolysis during pretreatment and led to the formation of stilbene structures. Other linkages, such as resinol (β-β′) and phenylcoumaran (β-5′), were resistant to degradation. The high degree of condensation of EOL indicated that condensation reactions occurred but did not impede the delignification efficiency of EOP. Both guaiacyl and syringyl lignin were found to be reactive toward condensation during pretreatment. The results from gel-permeation chromatography showed that the degree of polymerization (DP) of lignin significantly decreased by ∼85%, facilitating lignin solubilization in ethanol.

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U2 - 10.1021/ef901556u

DO - 10.1021/ef901556u

M3 - Article

AN - SCOPUS:77951098149

SN - 0887-0624

VL - 24

SP - 2723

EP - 2732

JO - Energy and Fuels

JF - Energy and Fuels

IS - 4

ER -

Chemical transformations of Buddleja davidii lignin during ethanol organosolv pretreatment

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