Mechanochemical Treatment Facilitates Two-Step Oxidative Depolymerization of Kraft Lignin

Soledad G. Yao; Justin K. Mobley; John Ralph; Mark Crocker; Sean Parkin; John P. Selegue; Mark S. Meier

doi:10.1021/acssuschemeng.7b04597

Mechanochemical Treatment Facilitates Two-Step Oxidative Depolymerization of Kraft Lignin

Soledad G. Yao
, Justin K. Mobley
, John Ralph
, Mark Crocker
, Sean Parkin
, John P. Selegue
, Mark S. Meier

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

60 Scopus citations

Abstract

Mechanochemical treatment of Indulin AT kraft lignin by ball-milling with KOH and toluene produces significant carbonyl functionality, among other changes. The chemical reactivity of the lignin is increased, resulting in greater lignin degradation from porphyrin oxidation followed by Baeyer-Villiger oxidation. The mechanochemical treatment produces a level of lignin oxidation that is similar to that produced by porphyrin-catalyzed oxidation. Combining mechanochemical treatment with porphyrin oxidation has a synergistic positive effect on the depolymerization of lignin, as demonstrated by a significantly higher yield of monomers. The methyl ester of vanillic acid was obtained as the main monomeric product (after methylation), along with of methyl 5-carbomethoxyvanillate, in a 10% yield, which is among the highest reported from kraft lignin.

Original language	English
Pages (from-to)	5990-5998
Number of pages	9
Journal	ACS Sustainable Chemistry and Engineering
Volume	6
Issue number	5
DOIs	https://doi.org/10.1021/acssuschemeng.7b04597
State	Published - May 7 2018

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

Funding

This material is based on work supported by the National Science Foundation under Cooperative Agreement No. 1355438 and was also funded in part by the DOE Great Lakes Bioenergy Research Center (DOE Office of Science BER DE-FC02-07ER64494). We also thank Mr. Art Sebesta for maintenance of the ball-mill used in this work and Mark McCrary for his assistance in the laboratory.

Funders	Funder number
DOE Great Lakes Bioenergy Research Center
DOE Office of Science BER DE-FC02-07ER64494	BER DE-FC02-07ER64494
National Science Foundation Arctic Social Science Program	1355438
U.S. Department of Energy EPSCoR
Biological and Environmental Research	DE-FC02-07ER64494

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

HSQC
Lignin depolymerization
Lignin oxidation
Vanillic acid

ASJC Scopus subject areas

General Chemistry
Environmental Chemistry
General Chemical Engineering
Renewable Energy, Sustainability and the Environment

Access to Document

10.1021/acssuschemeng.7b04597

Cite this

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title = "Mechanochemical Treatment Facilitates Two-Step Oxidative Depolymerization of Kraft Lignin",

abstract = "Mechanochemical treatment of Indulin AT kraft lignin by ball-milling with KOH and toluene produces significant carbonyl functionality, among other changes. The chemical reactivity of the lignin is increased, resulting in greater lignin degradation from porphyrin oxidation followed by Baeyer-Villiger oxidation. The mechanochemical treatment produces a level of lignin oxidation that is similar to that produced by porphyrin-catalyzed oxidation. Combining mechanochemical treatment with porphyrin oxidation has a synergistic positive effect on the depolymerization of lignin, as demonstrated by a significantly higher yield of monomers. The methyl ester of vanillic acid was obtained as the main monomeric product (after methylation), along with of methyl 5-carbomethoxyvanillate, in a 10\% yield, which is among the highest reported from kraft lignin.",

keywords = "HSQC, Lignin depolymerization, Lignin oxidation, Vanillic acid",

author = "Yao, \{Soledad G.\} and Mobley, \{Justin K.\} and John Ralph and Mark Crocker and Sean Parkin and Selegue, \{John P.\} and Meier, \{Mark S.\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acssuschemeng.7b04597",

language = "English",

volume = "6",

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TY - JOUR

T1 - Mechanochemical Treatment Facilitates Two-Step Oxidative Depolymerization of Kraft Lignin

AU - Yao, Soledad G.

AU - Mobley, Justin K.

AU - Ralph, John

AU - Crocker, Mark

AU - Parkin, Sean

AU - Selegue, John P.

AU - Meier, Mark S.

PY - 2018/5/7

Y1 - 2018/5/7

N2 - Mechanochemical treatment of Indulin AT kraft lignin by ball-milling with KOH and toluene produces significant carbonyl functionality, among other changes. The chemical reactivity of the lignin is increased, resulting in greater lignin degradation from porphyrin oxidation followed by Baeyer-Villiger oxidation. The mechanochemical treatment produces a level of lignin oxidation that is similar to that produced by porphyrin-catalyzed oxidation. Combining mechanochemical treatment with porphyrin oxidation has a synergistic positive effect on the depolymerization of lignin, as demonstrated by a significantly higher yield of monomers. The methyl ester of vanillic acid was obtained as the main monomeric product (after methylation), along with of methyl 5-carbomethoxyvanillate, in a 10% yield, which is among the highest reported from kraft lignin.

AB - Mechanochemical treatment of Indulin AT kraft lignin by ball-milling with KOH and toluene produces significant carbonyl functionality, among other changes. The chemical reactivity of the lignin is increased, resulting in greater lignin degradation from porphyrin oxidation followed by Baeyer-Villiger oxidation. The mechanochemical treatment produces a level of lignin oxidation that is similar to that produced by porphyrin-catalyzed oxidation. Combining mechanochemical treatment with porphyrin oxidation has a synergistic positive effect on the depolymerization of lignin, as demonstrated by a significantly higher yield of monomers. The methyl ester of vanillic acid was obtained as the main monomeric product (after methylation), along with of methyl 5-carbomethoxyvanillate, in a 10% yield, which is among the highest reported from kraft lignin.

KW - HSQC

KW - Lignin depolymerization

KW - Lignin oxidation

KW - Vanillic acid

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U2 - 10.1021/acssuschemeng.7b04597

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Mechanochemical Treatment Facilitates Two-Step Oxidative Depolymerization of Kraft Lignin

Abstract

Bibliographical note

Funding

UN SDGs

Keywords

ASJC Scopus subject areas

Access to Document

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Cite this