Low temperature hydrogenation of pyrolytic lignin over Ru/TiO2: 2D HSQC and 13C NMR study of reactants and products

Chen, Wen; McClelland, Daniel J.; Azarpira, Ali; Ralph, John; Luo, Zhongyang; Huber, George W.

doi:10.1039/C5GC02286J

Title: Low temperature hydrogenation of pyrolytic lignin over Ru/TiO₂: 2D HSQC and ¹³C NMR study of reactants and products

Journal Article · Thu Oct 15 00:00:00 EDT 2015 · Green Chemistry

DOI:https://doi.org/10.1039/C5GC02286J· OSTI ID:1475424

Chen, Wen ^[1]; McClelland, Daniel J. ^[2]; Azarpira, Ali ^[3]; Ralph, John ^[3]; Luo, Zhongyang ^[4]; Huber, George W. ^[2]

Zhejiang Univ., Hangzhou (China). State Key Lab. of Clean Energy Utilization; Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering
Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering
Univ. of Wisconsin, Madison, WI (United States). Dept. of Biochemistry. DOE Great Lakes Bioenergy Research Center. Dept. of Biological Systems Engineering
Zhejiang Univ., Hangzhou (China). State Key Lab. of Clean Energy Utilization

In this paper, pyrolytic lignin and hydrogenated pyrolytic lignin were characterized by 2D ¹H–¹³C HSQC and quantitative ¹³C NMR techniques. The pyrolytic lignin was produced from a mixed maple wood feedstock and separated from the bio-oil by water extraction. p-Hydroxyphenyl (H), guaiacyl (G), and syringyl (S) aromatics were the basic units of pyrolytic lignin. The native lignin β-aryl ether, phenylcoumaran and resinol structures were not present in the pyrolytic lignin. The hydrogenation was conducted with a Ru/TiO₂ catalyst at temperatures ranging from 25–150 °C with higher temperatures exhibiting higher levels of hydrogenation. Solid coke formed on the catalyst surface (1% coke yield) even for hydrogenation at 25 °C. The carbon yield of pyrolytic lignin to coke increased from 1% to 5% as the hydrogenation temperature increased from 25 to 150 °C. A single-step hydrogenation at 150 °C resulted in a reduction from 65% to 39% aromatic carbons. A three-step hydrogenation scheme at this same temperature resulted in a reduction of aromatic carbons from 65% to 17%. The decrease in the aromatic carbon corresponded with an increase in the aliphatic carbon. Coke formation reduced from a 5% carbon yield of pyrolytic lignin in the first hydrogenation step to a 1% carbon yield in each of the second and third hydrogenation steps. The pyrolytic lignin could be separated into a high and low molecular weight fraction. Finally, the coke yield from the high molecular weight fraction was twice as much as that from the low molecular weight fraction.

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Research Organization:: Univ. of Wisconsin, Madison, WI (United States); Zhejiang Univ., Hangzhou (China)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER); National Natural Science Foundation of China (NSFC); Major State Basic Research Development Program of China; China Scholarship Council

Grant/Contract Number:: FC02-07ER64494; 51336008; 2013CB228100

OSTI ID:: 1475424

Journal Information:: Green Chemistry, Vol. 18, Issue 1; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 64 works

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Title: Low temperature hydrogenation of pyrolytic lignin over Ru/TiO₂: 2D HSQC and ¹³C NMR study of reactants and products