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Title: An “ideal lignin” facilitates full biomass utilization

Abstract

Lignin, a major component of lignocellulosic biomass, is crucial to plant growth and development but is a major impediment to efficient biomass utilization in various processes. Valorizing lignin is increasingly realized as being essential. However, rapid condensation of lignin during acidic extraction leads to the formation of recalcitrant condensed units that, along with similar units and structural heterogeneity in native lignin, drastically limits product yield and selectivity. Catechyl lignin (C-lignin), which is essentially a benzodioxane homopolymer without condensed units, might represent an ideal lignin for valorization, as it circumvents these issues. We discovered that C-lignin is highly acid-resistant. Hydrogenolysis of C-lignin resulted in the cleavage of all benzodioxane structures to produce catechyl-type monomers in near-quantitative yield with a selectivity of 90% to a single monomer.

Authors:
ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [3]; ORCiD logo [4]; ORCiD logo [5];  [5]; ORCiD logo [6]; ORCiD logo [1]; ORCiD logo [1]
  1. Univ. of Wisconsin, Madison, WI (United States)
  2. Univ. of Wisconsin, Madison, WI (United States); Virginia Polytechnic Inst. and State Univ. (Virginia Tech), Blacksburg, VA (United States)
  3. Univ. of Wisconsin, Madison, WI (United States); Kyoto Univ. (Japan)
  4. State Univ. of New Jersey, New Brunswick, NJ (United States); Bakto Flavors LLC, North Brunswick, NJ (United States)
  5. Univ. of North Texas, Denton, TX (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  6. École Polytechnique Fédérale de Lausanne (Switzerland)
Publication Date:
Research Org.:
Great Lakes Bioenergy Research Center, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1543278
Grant/Contract Number:  
SC0018409; FC02-07ER64494; AC05-000R22725
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Science Advances
Additional Journal Information:
Journal Volume: 4; Journal Issue: 9; Journal ID: ISSN 2375-2548
Publisher:
AAAS
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Li, Yanding, Shuai, Li, Kim, Hoon, Motagamwala, Ali Hussain, Mobley, Justin K., Yue, Fengxia, Tobimatsu, Yuki, Havkin-Frenkel, Daphna, Chen, Fang, Dixon, Richard A., Luterbacher, Jeremy S., Dumesic, James A., and Ralph, John. An “ideal lignin” facilitates full biomass utilization. United States: N. p., 2018. Web. doi:10.1126/sciadv.aau2968.
Li, Yanding, Shuai, Li, Kim, Hoon, Motagamwala, Ali Hussain, Mobley, Justin K., Yue, Fengxia, Tobimatsu, Yuki, Havkin-Frenkel, Daphna, Chen, Fang, Dixon, Richard A., Luterbacher, Jeremy S., Dumesic, James A., & Ralph, John. An “ideal lignin” facilitates full biomass utilization. United States. doi:10.1126/sciadv.aau2968.
Li, Yanding, Shuai, Li, Kim, Hoon, Motagamwala, Ali Hussain, Mobley, Justin K., Yue, Fengxia, Tobimatsu, Yuki, Havkin-Frenkel, Daphna, Chen, Fang, Dixon, Richard A., Luterbacher, Jeremy S., Dumesic, James A., and Ralph, John. Fri . "An “ideal lignin” facilitates full biomass utilization". United States. doi:10.1126/sciadv.aau2968. https://www.osti.gov/servlets/purl/1543278.
@article{osti_1543278,
title = {An “ideal lignin” facilitates full biomass utilization},
author = {Li, Yanding and Shuai, Li and Kim, Hoon and Motagamwala, Ali Hussain and Mobley, Justin K. and Yue, Fengxia and Tobimatsu, Yuki and Havkin-Frenkel, Daphna and Chen, Fang and Dixon, Richard A. and Luterbacher, Jeremy S. and Dumesic, James A. and Ralph, John},
abstractNote = {Lignin, a major component of lignocellulosic biomass, is crucial to plant growth and development but is a major impediment to efficient biomass utilization in various processes. Valorizing lignin is increasingly realized as being essential. However, rapid condensation of lignin during acidic extraction leads to the formation of recalcitrant condensed units that, along with similar units and structural heterogeneity in native lignin, drastically limits product yield and selectivity. Catechyl lignin (C-lignin), which is essentially a benzodioxane homopolymer without condensed units, might represent an ideal lignin for valorization, as it circumvents these issues. We discovered that C-lignin is highly acid-resistant. Hydrogenolysis of C-lignin resulted in the cleavage of all benzodioxane structures to produce catechyl-type monomers in near-quantitative yield with a selectivity of 90% to a single monomer.},
doi = {10.1126/sciadv.aau2968},
journal = {Science Advances},
issn = {2375-2548},
number = 9,
volume = 4,
place = {United States},
year = {2018},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 14 works
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Figures / Tables:

Table 1 Table 1: Mass balance and total organic carbon (TOC) on hydrogenolysis of C-LBL and its resulting product oil.

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Works referenced in this record:

Formic-acid-induced depolymerization of oxidized lignin to aromatics
journal, November 2014

  • Rahimi, Alireza; Ulbrich, Arne; Coon, Joshua J.
  • Nature, Vol. 515, Issue 7526, p. 249-252
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Towards Quantitative Catalytic Lignin Depolymerization
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Modified lignin in tobacco and poplar plants over-expressing the Arabidopsis gene encoding ferulate 5-hydroxylase
journal, May 2000


Solvent Effects on the Hydrogenolysis of Diphenyl Ether with Raney Nickel and their Implications for the Conversion of Lignin
journal, April 2012


CCoAOMT suppression modifies lignin composition in Pinus radiata
journal, April 2011


    Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.