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Title: Reductive Catalytic Fractionation of C-Lignin

Abstract

Lignin composed solely of caffeyl alcohol units, or C-lignin, was recently discovered in the seed coats of a number of vanilla orchid and cactus species. The caffeyl alcohol monomer polymerizes into a highly uniform benzodioxane backbone, making C-lignin a promising substrate for lignin valorization, where heterogeneity is a key challenge. In this study, we used reductive catalytic fractionation (RCF) on vanilla seeds to investigate the depolymerization of naturally grown C-lignin. To overcome challenges associated with the high extractive content and poor sugar retention in vanilla seeds, the ratio of monomer yield to total lignin yield was used to isolate the depolymerization efficiency of C-lignin from the extraction efficiency of lignin from seeds. This approach allowed us to compare extents of depolymerization across lignin types and biomass feedstocks. C-Lignin RCF generated extents of depolymerization akin to those of hardwoods, despite observing incomplete benzodioxane cleavage due to catalyst deactivation caused by the seed extractives. In addition, depolymerization of C-lignin produced a favorable monomeric product distribution consisting of only propyl and propenyl catechol. These promising results suggest that genetic modification of other plant species to incorporate C-lignin has the potential to yield a single, valuable catechol product via RCF.

Authors:
 [1];  [1];  [2];  [2];  [2];  [3]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [1]
  1. Chemical Engineering, Massachusetts Institute of Technology, 25 Ames Street, Cambridge, Massachusetts 02139, United States
  2. National Renewable Energy Laboratory, 15013 Denver W Parkway, Golden, Colorado 80401, United States
  3. BioDiscovery Institute and Department of Biological Sciences, University of North Texas, 1155 Union Square, Denton, Texas 76203, United States
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1475114
Report Number(s):
NREL/JA-2A00-72505
Journal ID: ISSN 2168-0485
DOE Contract Number:  
AC36-08GO28308
Resource Type:
Journal Article
Journal Name:
ACS Sustainable Chemistry & Engineering
Additional Journal Information:
Journal Volume: 6; Journal Issue: 9; Journal ID: ISSN 2168-0485
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; benzodioxane; biomass conversion; catechol; depolymerization; hydrogenolysis; lignin first; solvolysis; vanilla seed

Citation Formats

Stone, Michael L., Anderson, Eric M., Meek, Kelly M., Reed, Michelle, Katahira, Rui, Chen, Fang, Dixon, Richard A., Beckham, Gregg T., and Román-Leshkov, Yuriy. Reductive Catalytic Fractionation of C-Lignin. United States: N. p., 2018. Web. doi:10.1021/acssuschemeng.8b02741.
Stone, Michael L., Anderson, Eric M., Meek, Kelly M., Reed, Michelle, Katahira, Rui, Chen, Fang, Dixon, Richard A., Beckham, Gregg T., & Román-Leshkov, Yuriy. Reductive Catalytic Fractionation of C-Lignin. United States. doi:10.1021/acssuschemeng.8b02741.
Stone, Michael L., Anderson, Eric M., Meek, Kelly M., Reed, Michelle, Katahira, Rui, Chen, Fang, Dixon, Richard A., Beckham, Gregg T., and Román-Leshkov, Yuriy. Thu . "Reductive Catalytic Fractionation of C-Lignin". United States. doi:10.1021/acssuschemeng.8b02741.
@article{osti_1475114,
title = {Reductive Catalytic Fractionation of C-Lignin},
author = {Stone, Michael L. and Anderson, Eric M. and Meek, Kelly M. and Reed, Michelle and Katahira, Rui and Chen, Fang and Dixon, Richard A. and Beckham, Gregg T. and Román-Leshkov, Yuriy},
abstractNote = {Lignin composed solely of caffeyl alcohol units, or C-lignin, was recently discovered in the seed coats of a number of vanilla orchid and cactus species. The caffeyl alcohol monomer polymerizes into a highly uniform benzodioxane backbone, making C-lignin a promising substrate for lignin valorization, where heterogeneity is a key challenge. In this study, we used reductive catalytic fractionation (RCF) on vanilla seeds to investigate the depolymerization of naturally grown C-lignin. To overcome challenges associated with the high extractive content and poor sugar retention in vanilla seeds, the ratio of monomer yield to total lignin yield was used to isolate the depolymerization efficiency of C-lignin from the extraction efficiency of lignin from seeds. This approach allowed us to compare extents of depolymerization across lignin types and biomass feedstocks. C-Lignin RCF generated extents of depolymerization akin to those of hardwoods, despite observing incomplete benzodioxane cleavage due to catalyst deactivation caused by the seed extractives. In addition, depolymerization of C-lignin produced a favorable monomeric product distribution consisting of only propyl and propenyl catechol. These promising results suggest that genetic modification of other plant species to incorporate C-lignin has the potential to yield a single, valuable catechol product via RCF.},
doi = {10.1021/acssuschemeng.8b02741},
journal = {ACS Sustainable Chemistry & Engineering},
issn = {2168-0485},
number = 9,
volume = 6,
place = {United States},
year = {2018},
month = {8}
}