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Lignin to Adipic Acid in a High-Yield Chemical and Biological Redox Process

Journal Article · · Nature
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  1. National Laboratory of the Rockies, Golden, CO (United States)
  2. Oak Ridge National Laboratory
  3. Massachusetts Institute of Technology
  4. University of Wisconsin-Madison
+ Show Author Affiliations
Viable manufacturing pathways to produce bio-based chemicals from renewable feedstocks, such as lignin derived from plant biomass, are needed to decarbonize the chemicals manufacturing sector. Converting the recalcitrant lignin polymer to valuable bioproducts remains a longstanding challenge in biorefining, with the highest reported single-product yield from lignin currently around 20 wt% (refs. 1,2,3,4). Most existing lignin depolymerization strategies target aryl-ether bond cleavage, which can produce aromatic monomers in yields of only about 30 wt%, and still as complex mixtures with C-C-linked dimers and oligomers5,6. The recalcitrance of these C-C linkages between aromatic moieties fundamentally limits single-product yields from lignin, prompting the development of strategies to efficiently cleave these C-C bonds3,7,8,9. Here we show how reductive processing of lignin from poplar accesses a hydrocarbon mixture of alkyl-aromatic monomers and oligomers that is privileged for oxidative conversion to monomeric aromatic carboxylic acids, comprising mostly benzoic acid and phthalic acid isomers in up to 73 wt% monomer yields, using a Co/Mn/Br catalyst. The soil bacterium Pseudomonas putida KT2440 was engineered to convert this mixture of aromatic carboxylic acids to muconolactone, a precursor to bio-based nylons, enabling final adipic acid yields up to 26 wt% (gram adipic acid per gram lignin) with a maximum theoretical yield of 57 wt%. This pairing of reductive and oxidative steps with lignin resembles processes in petrochemical refining and shows how lignin may be converted into a single, valuable bioproduct in high yields.
Research Organization:
National Laboratory of the Rockies (NLR), Golden, CO (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Bioenergy Technologies Office; USDOE Office of Science (SC), Biological and Environmental Research (BER)
Grant/Contract Number:
AC36-08GO28308
OSTI ID:
3376125
Report Number(s):
NLR/JA-2A00-96426
Journal Information:
Nature, Journal Name: Nature Vol. 654
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
aromatic carboxylic acid
biological redox
muconolactone
nylon