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Title: Electrochemical Conversion of Biologically Produced Muconic Acid: Key Considerations for Scale-Up and Corresponding Technoeconomic Analysis

We present muconic acid, an unsaturated diacid that can be produced from cellulosic sugars and lignin monomers by fermentation, emerges as a promising intermediate for the sustainable manufacture of commodity polyamides and polyesters including Nylon-6,6 and polyethylene terephthalate (PET). Current conversion schemes consist in the biological production of cis,cis-muconic acid using metabolically engineered yeasts and bacteria, and the subsequent diversification to adipic acid, terephthalic acid, and their derivatives using chemical catalysts. In some instances, conventional precious metal catalysts can be advantageously replaced by base metal electrocatalysts. Here, we show the economic relevance of utilizing a hybrid biological–electrochemical conversion scheme to convert glucose to trans-3-hexenedioic acid (t3HDA), a monomer used for the synthesis of bioadvantaged Nylon-6,6. Potential roadblocks to biological and electrochemical integration in a single reactor, including electrocatalyst deactivation due to biogenic impurities and low faradaic efficiency inherent to side reactions in complex media, have been studied and addressed. In this study, t3HDA was produced with 94% yield and 100% faradaic efficiency. With consideration of the high t3HDA yield and faradaic efficiency, a technoeconomic analysis was developed on the basis of the current yield and titer achieved for muconic acid, the figures of merit defined for industrial electrochemical processes, andmore » the separation of the desired product from the medium. On the basis of this analysis, t3HDA could be produced for approximately $2.00 kg –1. The low cost for t3HDA is a primary factor of the electrochemical route being able to cascade biological catalysis and electrocatalysis in one pot without separation of the muconic acid intermediate from the fermentation broth.« less
Authors:
 [1] ;  [2] ;  [2] ;  [3] ;  [4] ;  [2] ;  [2] ;  [5] ;  [4] ;  [3] ;  [1] ;  [1]
  1. Iowa State Univ., Ames, IA (United States). Department of Chemical and Biological Engineering; NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States); Ames Lab., Ames, IA (United States)
  2. Iowa State Univ., Ames, IA (United States). Department of Chemical and Biological Engineering; NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States)
  3. NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States); Iowa State Univ., Ames, IA (United States). Department of Agricultural and Biosystems Engineering
  4. Iowa State Univ., Ames, IA (United States). Department of Chemistry; NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States)
  5. NSF Engineering Research Center for Biorenewable Chemicals (CBiRC), Ames, IA (United States)
Publication Date:
Report Number(s):
IS-J-9181
Journal ID: ISSN 2168-0485
Grant/Contract Number:
AC02-07CH11358; 1101284; EEC-0813570; CBET-1512126
Type:
Accepted Manuscript
Journal Name:
ACS Sustainable Chemistry & Engineering
Additional Journal Information:
Journal Volume: 4; Journal Issue: 12; Journal ID: ISSN 2168-0485
Publisher:
American Chemical Society (ACS)
Research Org:
Ames Laboratory (AMES), Ames, IA (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 3-Hexenedioic acid; Biorenewable chemicals; Cascade catalysis; Electrocatalysis; Electrochemical hydrogenation; Hydromuconic acid; Muconic acid; Nylon
OSTI Identifier:
1355400

Matthiesen, John E., Suástegui, Miguel, Wu, Yutong, Viswanathan, Mothi, Qu, Yang, Cao, Mingfeng, Rodriguez-Quiroz, Natalia, Okerlund, Adam, Kraus, George, Raman, D. Raj, Shao, Zengyi, and Tessonnier, Jean-Philippe. Electrochemical Conversion of Biologically Produced Muconic Acid: Key Considerations for Scale-Up and Corresponding Technoeconomic Analysis. United States: N. p., Web. doi:10.1021/acssuschemeng.6b01981.
Matthiesen, John E., Suástegui, Miguel, Wu, Yutong, Viswanathan, Mothi, Qu, Yang, Cao, Mingfeng, Rodriguez-Quiroz, Natalia, Okerlund, Adam, Kraus, George, Raman, D. Raj, Shao, Zengyi, & Tessonnier, Jean-Philippe. Electrochemical Conversion of Biologically Produced Muconic Acid: Key Considerations for Scale-Up and Corresponding Technoeconomic Analysis. United States. doi:10.1021/acssuschemeng.6b01981.
Matthiesen, John E., Suástegui, Miguel, Wu, Yutong, Viswanathan, Mothi, Qu, Yang, Cao, Mingfeng, Rodriguez-Quiroz, Natalia, Okerlund, Adam, Kraus, George, Raman, D. Raj, Shao, Zengyi, and Tessonnier, Jean-Philippe. 2016. "Electrochemical Conversion of Biologically Produced Muconic Acid: Key Considerations for Scale-Up and Corresponding Technoeconomic Analysis". United States. doi:10.1021/acssuschemeng.6b01981. https://www.osti.gov/servlets/purl/1355400.
@article{osti_1355400,
title = {Electrochemical Conversion of Biologically Produced Muconic Acid: Key Considerations for Scale-Up and Corresponding Technoeconomic Analysis},
author = {Matthiesen, John E. and Suástegui, Miguel and Wu, Yutong and Viswanathan, Mothi and Qu, Yang and Cao, Mingfeng and Rodriguez-Quiroz, Natalia and Okerlund, Adam and Kraus, George and Raman, D. Raj and Shao, Zengyi and Tessonnier, Jean-Philippe},
abstractNote = {We present muconic acid, an unsaturated diacid that can be produced from cellulosic sugars and lignin monomers by fermentation, emerges as a promising intermediate for the sustainable manufacture of commodity polyamides and polyesters including Nylon-6,6 and polyethylene terephthalate (PET). Current conversion schemes consist in the biological production of cis,cis-muconic acid using metabolically engineered yeasts and bacteria, and the subsequent diversification to adipic acid, terephthalic acid, and their derivatives using chemical catalysts. In some instances, conventional precious metal catalysts can be advantageously replaced by base metal electrocatalysts. Here, we show the economic relevance of utilizing a hybrid biological–electrochemical conversion scheme to convert glucose to trans-3-hexenedioic acid (t3HDA), a monomer used for the synthesis of bioadvantaged Nylon-6,6. Potential roadblocks to biological and electrochemical integration in a single reactor, including electrocatalyst deactivation due to biogenic impurities and low faradaic efficiency inherent to side reactions in complex media, have been studied and addressed. In this study, t3HDA was produced with 94% yield and 100% faradaic efficiency. With consideration of the high t3HDA yield and faradaic efficiency, a technoeconomic analysis was developed on the basis of the current yield and titer achieved for muconic acid, the figures of merit defined for industrial electrochemical processes, and the separation of the desired product from the medium. On the basis of this analysis, t3HDA could be produced for approximately $2.00 kg–1. The low cost for t3HDA is a primary factor of the electrochemical route being able to cascade biological catalysis and electrocatalysis in one pot without separation of the muconic acid intermediate from the fermentation broth.},
doi = {10.1021/acssuschemeng.6b01981},
journal = {ACS Sustainable Chemistry & Engineering},
number = 12,
volume = 4,
place = {United States},
year = {2016},
month = {10}
}