Mechanistic Study of the Acid Degradation of Lignin Model Compounds: Abstract No. CELL-5

Research output: Contribution to conferencePaper


Lignin is a major constituent of biomass, which remains underutilized in selective biomass conversion strategies to renewable fuels and chemicals. Here we are interested in understanding the mechanisms related to the acid deconstruction of lignin with a combined theoretical and experimental approach. Two model dimers with a b-O-4 aryl ether linkage (2-phenoxy-1-phenethanol and2-phenoxy-1-phenyl-1,3 propanediol) and model dimmers with an a-O-4 aryl ether linkage were synthesized and deconstructed in H2SO4. The major products of the acidolysis of the b-O-4 compounds consisted of phenol and two aldehydes, phenylacetaldehyde and benzaldehyde. Quantum mechanical calculations were employed to elucidate possible deconstruction mechanisms with transition state theory. Toconfirm proposed mechanisms several possible intermediates were studied under similar acidolysis conditions. Although the resonance time for cleavage was on the order several hours, we have shown that the cleavage of the aryl ether linkage affords phenol and aldehydes. We would next like to utilize our mechanism of aryl ether cleavage in actual lignin.
Original languageAmerican English
StatePublished - 2012
EventAmerican Chemical Society. 244th ACS National Meeting - Philadelphia, Pennsylvania
Duration: 19 Aug 201223 Aug 2012


ConferenceAmerican Chemical Society. 244th ACS National Meeting
CityPhiladelphia, Pennsylvania

NREL Publication Number

  • NREL/CP-5100-56378


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