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Title: Valorization of aqueous waste streams from thermochemical biorefineries

Abstract

Thermochemical conversion of lignocellulosic biomass is an enticing route to produce fuels and oxygenated chemicals and could enable circular carbon utilization. In most thermochemical conversion processes, however, some chemical co-products are lost in aqueous waste streams that are both dilute and heterogeneous. Cost-competitive isolation of these chemical co-products is challenging due to the high-purity requirements typically necessary for bulk chemical production. In this work, we show the production and isolation of two biomass-derived monomers, phenol and catechol, from a comprehensively characterized aqueous waste stream generated via catalytic fast pyrolysis. Specifically, we separate phenol and catechol to 97 wt% purity using the industrially relevant processes of liquid-liquid extraction, distillation, and recrystallization. Techno-economic analysis predicts that a mixed phenolics stream can be produced from the waste stream at a minimum selling price of $1.06 kg-1. Overall, this work demonstrates an approach to high-purity oxygenated aromatic compounds that is potentially economically feasible and technically achievable which increases the atom efficiency of thermochemical conversion through waste stream valorization.

Authors:
ORCiD logo [1];  [1]; ORCiD logo [2]; ORCiD logo [1];  [1]; ORCiD logo [1];  [2]; ORCiD logo [1]; ORCiD logo [1]
  1. National Bioenergy Center; National Renewable Energy Laboratory; Golden; USA
  2. Biosciences Center; National Renewable Energy Laboratory; Golden; USA
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B)
OSTI Identifier:
1543354
Alternate Identifier(s):
OSTI ID: 1550784
Report Number(s):
NREL/JA-5100-74540
Journal ID: ISSN 1463-9262; GRCHFJ
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Published Article
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Name: Green Chemistry Journal Volume: 21 Journal Issue: 15; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry
Country of Publication:
United Kingdom
Language:
English
Subject:
09 BIOMASS FUELS; thermochemical conversion; lignocellulosic biomass; biomass fuels; biorefineries; carbon utilization

Citation Formats

Wilson, A. Nolan, Dutta, Abhijit, Black, Brenna A., Mukarakate, Calvin, Magrini, Kim, Schaidle, Joshua A., Michener, William E., Beckham, Gregg T., and Nimlos, Mark R. Valorization of aqueous waste streams from thermochemical biorefineries. United Kingdom: N. p., 2019. Web. doi:10.1039/C9GC00902G.
Wilson, A. Nolan, Dutta, Abhijit, Black, Brenna A., Mukarakate, Calvin, Magrini, Kim, Schaidle, Joshua A., Michener, William E., Beckham, Gregg T., & Nimlos, Mark R. Valorization of aqueous waste streams from thermochemical biorefineries. United Kingdom. doi:10.1039/C9GC00902G.
Wilson, A. Nolan, Dutta, Abhijit, Black, Brenna A., Mukarakate, Calvin, Magrini, Kim, Schaidle, Joshua A., Michener, William E., Beckham, Gregg T., and Nimlos, Mark R. Tue . "Valorization of aqueous waste streams from thermochemical biorefineries". United Kingdom. doi:10.1039/C9GC00902G.
@article{osti_1543354,
title = {Valorization of aqueous waste streams from thermochemical biorefineries},
author = {Wilson, A. Nolan and Dutta, Abhijit and Black, Brenna A. and Mukarakate, Calvin and Magrini, Kim and Schaidle, Joshua A. and Michener, William E. and Beckham, Gregg T. and Nimlos, Mark R.},
abstractNote = {Thermochemical conversion of lignocellulosic biomass is an enticing route to produce fuels and oxygenated chemicals and could enable circular carbon utilization. In most thermochemical conversion processes, however, some chemical co-products are lost in aqueous waste streams that are both dilute and heterogeneous. Cost-competitive isolation of these chemical co-products is challenging due to the high-purity requirements typically necessary for bulk chemical production. In this work, we show the production and isolation of two biomass-derived monomers, phenol and catechol, from a comprehensively characterized aqueous waste stream generated via catalytic fast pyrolysis. Specifically, we separate phenol and catechol to 97 wt% purity using the industrially relevant processes of liquid-liquid extraction, distillation, and recrystallization. Techno-economic analysis predicts that a mixed phenolics stream can be produced from the waste stream at a minimum selling price of $1.06 kg-1. Overall, this work demonstrates an approach to high-purity oxygenated aromatic compounds that is potentially economically feasible and technically achievable which increases the atom efficiency of thermochemical conversion through waste stream valorization.},
doi = {10.1039/C9GC00902G},
journal = {Green Chemistry},
number = 15,
volume = 21,
place = {United Kingdom},
year = {2019},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C9GC00902G

Citation Metrics:
Cited by: 2 works
Citation information provided by
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    Works referencing / citing this record:

    Catechol-Based Biomimetic Functional Materials
    journal, November 2012

    • Sedó, Josep; Saiz-Poseu, Javier; Busqué, Felix
    • Advanced Materials, Vol. 25, Issue 5
    • DOI: 10.1002/adma.201202343

    Production of aromatics by catalytic fast pyrolysis of cellulose in a bubbling fluidized bed reactor
    journal, February 2014

    • Karanjkar, Pranav U.; Coolman, Robert J.; Huber, George W.
    • AIChE Journal, Vol. 60, Issue 4
    • DOI: 10.1002/aic.14376

    Beyond ethanol: a techno-economic analysis of an integrated corn biorefinery for the production of hydrocarbon fuels and chemicals
    journal, December 2014

    • Wang, Kaige; Ou, Longwen; Brown, Tristan
    • Biofuels, Bioproducts and Biorefining, Vol. 9, Issue 2
    • DOI: 10.1002/bbb.1529

    [TC2015] applicability of medium boiling fraction of flash pyrolysis condensates in phenolic resins
    journal, March 2017

    • Conrad, Stefan; Westermeyer, Jan; Schulzke, Tim
    • Environmental Progress & Sustainable Energy, Vol. 36, Issue 3
    • DOI: 10.1002/ep.12586

    Formaldehyde-Free Wood Adhesives from Decayed Wood
    journal, April 2005

    • Li, Kaichang; Geng, Xinglian
    • Macromolecular Rapid Communications, Vol. 26, Issue 7
    • DOI: 10.1002/marc.200400594

    Industrial catalytic processes—phenol production
    journal, February 2005


    Production, separation and applications of phenolic-rich bio-oil – A review
    journal, February 2015


    Strategies for recovering phenol from wastewater: thermodynamic evaluation and environmental concerns
    journal, February 2005


    The effect of ZSM-5 catalyst support in catalytic pyrolysis of biomass and compounds abundant in pyrolysis bio-oils
    journal, November 2016

    • Du, Shoucheng; Gamliel, David P.; Valla, Julia A.
    • Journal of Analytical and Applied Pyrolysis, Vol. 122
    • DOI: 10.1016/j.jaap.2016.11.002

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    • Effendi, A.; Gerhauser, H.; Bridgwater, A. V.
    • Renewable and Sustainable Energy Reviews, Vol. 12, Issue 8
    • DOI: 10.1016/j.rser.2007.04.008

    Biomass pyrolysis—A review of modelling, process parameters and catalytic studies
    journal, October 2015

    • Sharma, Abhishek; Pareek, Vishnu; Zhang, Dongke
    • Renewable and Sustainable Energy Reviews, Vol. 50
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    • Stanford, John P.; Hall, Patrick H.; Rover, Marjorie R.
    • Separation and Purification Technology, Vol. 194
    • DOI: 10.1016/j.seppur.2017.11.040

    Reprint of: Pyrolysis technologies for municipal solid waste: A review
    journal, March 2015


    Metabolic engineering of Pseudomonas taiwanensis VLB120 with minimal genomic modifications for high-yield phenol production
    journal, May 2018


    Bright Side of Lignin Depolymerization: Toward New Platform Chemicals
    journal, January 2018


    Catalytic Upgrading of Biomass Pyrolysis Oxygenates with Vacuum Gas Oil Using a Davison Circulating Riser Reactor
    journal, January 2018


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    journal, February 2016


    50th Anniversary Perspective : There Is a Great Future in Sustainable Polymers
    journal, May 2017


    Hydrocarbon Liquid Production via Catalytic Hydroprocessing of Phenolic Oils Fractionated from Fast Pyrolysis of Red Oak and Corn Stover
    journal, April 2015


    The Techno-Economic Basis for Coproduct Manufacturing To Enable Hydrocarbon Fuel Production from Lignocellulosic Biomass
    journal, May 2016


    Aqueous Stream Characterization from Biomass Fast Pyrolysis and Catalytic Fast Pyrolysis
    journal, September 2016

    • Black, Brenna A.; Michener, William E.; Ramirez, Kelsey J.
    • ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 12
    • DOI: 10.1021/acssuschemeng.6b01766

    Integrated Biorefining: Coproduction of Renewable Resol Biopolymer for Aqueous Stream Valorization
    journal, July 2017

    • Wilson, A. Nolan; Price, Mariel J.; Mukarakate, Calvin
    • ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 8
    • DOI: 10.1021/acssuschemeng.7b00864

    Characterization and Catalytic Upgrading of Aqueous Stream Carbon from Catalytic Fast Pyrolysis of Biomass
    journal, November 2017


    Chemical Routes for the Transformation of Biomass into Chemicals
    journal, June 2007

    • Corma, Avelino; Iborra, Sara; Velty, Alexandra
    • Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502
    • DOI: 10.1021/cr050989d

    Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering
    journal, September 2006

    • Huber, George W.; Iborra, Sara; Corma, Avelino
    • Chemical Reviews, Vol. 106, Issue 9, p. 4044-4098
    • DOI: 10.1021/cr068360d

    Hydrogen Production via Steam Reforming of the Aqueous Phase of Bio-Oil in a Fixed Bed Reactor
    journal, September 2006

    • Kechagiopoulos, Panagiotis N.; Voutetakis, Spyros S.; Lemonidou, Angeliki A.
    • Energy & Fuels, Vol. 20, Issue 5
    • DOI: 10.1021/ef060083q

    Physical Data on Some Organic Compounds
    journal, December 1949

    • Dreisbach, R. R.; Martin, R. A.
    • Industrial & Engineering Chemistry, Vol. 41, Issue 12
    • DOI: 10.1021/ie50480a053

    Assessing Safety, Health, and Environmental Impact Early during Process Development
    journal, April 2000

    • Koller, Guntram; Fischer, Ulrich; Hungerbühler, Konrad
    • Industrial & Engineering Chemistry Research, Vol. 39, Issue 4
    • DOI: 10.1021/ie990669i

    Separation of phenol from its mixture with o-cresol by adductive crystallization
    journal, April 1992

    • Jadhav, Vivek K.; Chivate, Madhav R.; Tavare, Narayan S.
    • Journal of Chemical & Engineering Data, Vol. 37, Issue 2
    • DOI: 10.1021/je00006a026

    Opportunities and challenges for a sustainable energy future
    journal, August 2012

    • Chu, Steven; Majumdar, Arun
    • Nature, Vol. 488, Issue 7411, p. 294-303
    • DOI: 10.1038/nature11475

    Catalytic conversion of biomass to biofuels
    journal, January 2010

    • Alonso, David Martin; Bond, Jesse Q.; Dumesic, James A.
    • Green Chemistry, Vol. 12, Issue 9, p. 1493-1513
    • DOI: 10.1039/c004654j

    Product quality and catalyst deactivation in a four day catalytic fast pyrolysis production run
    journal, January 2014

    • Paasikallio, Ville; Lindfors, Christian; Kuoppala, Eeva
    • Green Chemistry, Vol. 16, Issue 7
    • DOI: 10.1039/c4gc00571f

    Phase Transition Enthalpy Measurements of Organic and Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From 1880 to 2015. Part 1. C 1 − C 10
    journal, September 2016

    • Acree, William; Chickos, James S.
    • Journal of Physical and Chemical Reference Data, Vol. 45, Issue 3
    • DOI: 10.1063/1.4948363