skip to main content

DOE PAGESDOE PAGES

Title: Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification

Lignin structural studies play an essential role both in understanding the development of plant cell walls and for valorizing lignocellulosics as renewable biomaterials. Dimeric products released by selectively cleaving β–aryl ether linkages between lignin units reflect the distribution of recalcitrant lignin units, but have been neither absolutely defined nor quantitatively determined. Here in this work, 12 guaiacyl-type thioacidolysis dimers were identified and quantified using newly synthesized standards. One product previously attributed to deriving from β–1-coupled units was established as resulting from β–5 units, correcting an analytical quandary. Another longstanding dilemma, that no β–β dimers were recognized in thioacidolysis products from gymnosperms, was resolved with the discovery of two such authenticated compounds. Finally, individual GC response factors for each standard compound allowed rigorous quantification of dimeric products released from softwood lignins, affording insight into the various interunit-linkage distributions in lignins and thereby guiding the valorization of lignocellulosics.
Authors:
ORCiD logo [1] ; ORCiD logo [1] ; ORCiD logo [2] ; ORCiD logo [3] ; ORCiD logo [2]
  1. South China University of Technology, Tianhe District, Guangzhou (China). State Key Laboratory of Pulp and Paper Engineering; Univ. of Wisconsin, Madison, WI (United States). Department of Biochemistry and DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute
  2. Univ. of Wisconsin, Madison, WI (United States). Department of Biochemistry and DOE Great Lakes Bioenergy Research Center, Wisconsin Energy Institute
  3. Beijing Forestry University, Haidian District, Beijing (China). Beijing Key Laboratory of Lignocellulosic Chemistry
Publication Date:
Grant/Contract Number:
FC02-07ER64494; FC02- 07ER64494
Type:
Published Article
Journal Name:
ChemSusChem
Additional Journal Information:
Journal Volume: 10; Journal Issue: 5; Journal ID: ISSN 1864-5631
Publisher:
ChemPubSoc Europe
Research Org:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; analytical methods; GC-FID; lignin dimers; response factor; synthesis design
OSTI Identifier:
1346254
Alternate Identifier(s):
OSTI ID: 1346255; OSTI ID: 1427629

Yue, Fengxia, Lu, Fachuang, Regner, Matt, Sun, Runcang, and Ralph, John. Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification. United States: N. p., Web. doi:10.1002/cssc.201700101.
Yue, Fengxia, Lu, Fachuang, Regner, Matt, Sun, Runcang, & Ralph, John. Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification. United States. doi:10.1002/cssc.201700101.
Yue, Fengxia, Lu, Fachuang, Regner, Matt, Sun, Runcang, and Ralph, John. 2017. "Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification". United States. doi:10.1002/cssc.201700101.
@article{osti_1346254,
title = {Lignin-Derived Thioacidolysis Dimers: Reevaluation, New Products, Authentication, and Quantification},
author = {Yue, Fengxia and Lu, Fachuang and Regner, Matt and Sun, Runcang and Ralph, John},
abstractNote = {Lignin structural studies play an essential role both in understanding the development of plant cell walls and for valorizing lignocellulosics as renewable biomaterials. Dimeric products released by selectively cleaving β–aryl ether linkages between lignin units reflect the distribution of recalcitrant lignin units, but have been neither absolutely defined nor quantitatively determined. Here in this work, 12 guaiacyl-type thioacidolysis dimers were identified and quantified using newly synthesized standards. One product previously attributed to deriving from β–1-coupled units was established as resulting from β–5 units, correcting an analytical quandary. Another longstanding dilemma, that no β–β dimers were recognized in thioacidolysis products from gymnosperms, was resolved with the discovery of two such authenticated compounds. Finally, individual GC response factors for each standard compound allowed rigorous quantification of dimeric products released from softwood lignins, affording insight into the various interunit-linkage distributions in lignins and thereby guiding the valorization of lignocellulosics.},
doi = {10.1002/cssc.201700101},
journal = {ChemSusChem},
number = 5,
volume = 10,
place = {United States},
year = {2017},
month = {1}
}

Works referenced in this record:

Lignin primary structures and dirigent sites
journal, August 2005

Catalytic Transformation of Lignin for the Production of Chemicals and Fuels
journal, October 2015

Strategies for the Conversion of Lignin to High-Value Polymeric Materials: Review and Perspective
journal, December 2015

Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenyl- propanoids
journal, January 2004