Identification of Known and Novel Monomers for Poly(hydroxyurethanes) from Biobased Materials

Wang, Guanhua; Lopez, Lauren; Coile, Matthew; Chen, Yixuan; Torkelson, John M.; Broadbelt, Linda J.

doi:10.1021/acs.iecr.0c06351

Identification of Known and Novel Monomers for Poly(hydroxyurethanes) from Biobased Materials

Journal Article · Wed Mar 10 00:00:00 EST 2021 · Industrial and Engineering Chemistry Research

DOI:https://doi.org/10.1021/acs.iecr.0c06351· OSTI ID:1772855

Wang, Guanhua ^[1]; Lopez, Lauren ^[2]; Coile, Matthew ^[2]; Chen, Yixuan ^[2]; ^[2]; ^[2]

Northwestern Univ., Evanston, IL (United States); Northwestern University
Northwestern Univ., Evanston, IL (United States)

Sourcing polymers from biobased materials is desirable for a transition to a more sustainable world. However, finding new monomers sourced from biobased molecules requires extensive experimental effort, due to the fact that most biomolecules lack the functional groups or properties needed to serve as a monomer in a particular polymeric system without chemical modification. In this work, we demonstrate a computational screening method to obtain monomers of a non-isocyanate polyurethane (NIPU), polyhydroxyurethane (PHU), from biomolecules. Our method generates candidate monomers from a list of 15 selected biobased starting molecules by performing chemical transformations that are standard to chemical catalysis and organic synthesis on these starting molecules and then screening the results for molecules with moieties that can be used as monomers for a PHU. Product molecules from two generations of reaction, a total number of 20,057, were analyzed automatically to identify molecules that have two or more epoxy or cyclic carbonate functional groups as candidates for further derivatization. These 21 candidate molecules were then subjected to another two generations of reaction, producing a set of 17,913 additional molecules. Further scrutiny of this set for desired functional groups characterizing PHUs and querying against the PubChem database was carried out, and 15 known molecules that are commercially available were identified, with the desirable features that they are predicted to be derived from biobased starting molecules in four or fewer steps. Moreover, molecule space generated from this process was primarily comprised of molecules that were not known to PubChem, indicating the framework also has the ability to generate novel candidate monomers that originate from biobased starting points.

View Accepted Manuscript (DOE)

Research Organization:: Northwestern Univ., Evanston, IL (United States); Northwestern University, Evanston, IL (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Bioenergy Technologies Office

Grant/Contract Number:: EE0008928

OSTI ID:: 1772855

Alternate ID(s):: OSTI ID: 2370069
OSTI ID: 1784319

Journal Information:: Industrial and Engineering Chemistry Research, Journal Name: Industrial and Engineering Chemistry Research Journal Issue: 18 Vol. 60; ISSN 0888-5885

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (62)

Enzymatic Oxidation of Methyl Groups on Aromatic Heterocycles: A Versatile Method for the Preparation of Heteroaromatic Carboxylic Acids Kiener, Andreas Angewandte Chemie International Edition in English, Vol. 31, Issue 6 https://doi.org/10.1002/anie.199207741	journal	June 1992
Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation Giri, Ramesh; Liang, Jue; Lei, Jian-Guang Angewandte Chemie International Edition, Vol. 44, Issue 45 https://doi.org/10.1002/anie.200502767	journal	November 2005
Incorporation of carbon dioxide into soybean oil and subsequent preparation and studies of nonisocyanate polyurethane networks Tamami, B.; Sohn, S.; Wilkes, G. L. Journal of Applied Polymer Science, Vol. 92, Issue 2 https://doi.org/10.1002/app.20049	journal	January 2004
Hydrogen bonds prevent obtaining high molar mass PHUs Blain, Marine; Cornille, Adrien; Boutevin, Bernard Journal of Applied Polymer Science, Vol. 134, Issue 45 https://doi.org/10.1002/app.44958	journal	February 2017
Structural effects on the reprocessability and stress relaxation of crosslinked polyhydroxyurethanes: ARTICLE Fortman, David J.; Brutman, Jacob P.; Hillmyer, Marc A. Journal of Applied Polymer Science, Vol. 134, Issue 45 https://doi.org/10.1002/app.44984	journal	March 2017
Recent Advances in Sustainable Plastic Upcycling and Biopolymers Sohn, Yu Jung; Kim, Hee Taek; Baritugo, Kei‐Anne Biotechnology Journal, Vol. 15, Issue 6 https://doi.org/10.1002/biot.201900489	journal	April 2020
Computational framework for predictive biodegradation Finley, Stacey D.; Broadbelt, Linda J.; Hatzimanikatis, Vassily Biotechnology and Bioengineering, Vol. 104, Issue 6 https://doi.org/10.1002/bit.22489	journal	December 2009
Discovery and analysis of novel metabolic pathways for the biosynthesis of industrial chemicals: 3-hydroxypropanoate Henry, Christopher S.; Broadbelt, Linda J.; Hatzimanikatis, Vassily Biotechnology and Bioengineering https://doi.org/10.1002/bit.22673	journal	January 2010
Exploring De Novo metabolic pathways from pyruvate to propionic acid Stine, Andrew; Zhang, Miaomin; Ro, Soo Biotechnology Progress, Vol. 32, Issue 2 https://doi.org/10.1002/btpr.2233	journal	March 2016
Thermochemical Data of Organic Compounds Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Springer Dordrecht https://doi.org/10.1007/978-94-009-4099-4	book	January 1986
Prediction of the enthalpy of vaporization by the group contribution method Basařová, Pavlína; Svoboda, Václav Fluid Phase Equilibria, Vol. 105, Issue 1 https://doi.org/10.1016/0378-3812(94)02599-V	journal	March 1995
An improved Williamson ether synthesis using phase transfer catalysis Freedman, H. H.; Dubois, R. A. Tetrahedron Letters, Vol. 16, Issue 38 https://doi.org/10.1016/S0040-4039(00)91417-5	journal	January 1975
Biomass resource facilities and biomass conversion processing for fuels and chemicals Demirbaş, Ayhan Energy Conversion and Management, Vol. 42, Issue 11 https://doi.org/10.1016/S0196-8904(00)00137-0	journal	July 2001
New diol processes: 1,3-propanediol and 1,4-butanediol Haas, T.; Jaeger, B.; Weber, R. Applied Catalysis A: General, Vol. 280, Issue 1 https://doi.org/10.1016/j.apcata.2004.08.027	journal	February 2005
Efficient decolorization and deproteinization using uniform polymer microspheres in the succinic acid biorefinery from bio-waste cotton (Gossypium hirsutum L.) stalks Li, Qiang; Lei, Jiandu; Zhang, Rongyue Bioresource Technology, Vol. 135 https://doi.org/10.1016/j.biortech.2012.06.101	journal	May 2013
Biowaste-to-bioenergy using biological methods – A mini-review Bhatia, Shashi Kant; Joo, Hwang-Soo; Yang, Yung-Hun Energy Conversion and Management, Vol. 177 https://doi.org/10.1016/j.enconman.2018.09.090	journal	December 2018
Food versus fuel: What do prices tell us? Zhang, Zibin; Lohr, Luanne; Escalante, Cesar Energy Policy, Vol. 38, Issue 1 https://doi.org/10.1016/j.enpol.2009.09.034	journal	January 2010
Poly(hydroxy urethane)s based on renewable diglycerol dicarbonate van Velthoven, Juliën L. J.; Gootjes, Linda; van Es, Daan S. European Polymer Journal, Vol. 70 https://doi.org/10.1016/j.eurpolymj.2015.07.011	journal	September 2015
An overview of the chemical composition of biomass Vassilev, Stanislav V.; Baxter, David; Andersen, Lars K. Fuel, Vol. 89, Issue 5 https://doi.org/10.1016/j.fuel.2009.10.022	journal	May 2010
A new amino-alcohol originated from carbon dioxide and its application as chain extender in the preparation of polyurethane Li, Xiaoyun; Ke, Jiexi; Wang, Junwei Journal of CO2 Utilization, Vol. 26 https://doi.org/10.1016/j.jcou.2018.04.018	journal	July 2018
Chemical equilibrium of glycerol carbonate synthesis from glycerol Li, Jiabo; Wang, Tao The Journal of Chemical Thermodynamics, Vol. 43, Issue 5 https://doi.org/10.1016/j.jct.2010.12.013	journal	May 2011
Food versus fuel? Going beyond biofuels Tomei, Julia; Helliwell, Richard Land Use Policy, Vol. 56 https://doi.org/10.1016/j.landusepol.2015.11.015	journal	November 2016
A study on the carboxylation of glycerol to glycerol carbonate with carbon dioxide: The role of the catalyst, solvent and reaction conditions Aresta, Michele; Dibenedetto, Angela; Nocito, Francesco Journal of Molecular Catalysis A: Chemical, Vol. 257, Issue 1-2 https://doi.org/10.1016/j.molcata.2006.05.021	journal	September 2006
Combustion characteristics of different biomass fuels Demirbas, A. Progress in Energy and Combustion Science, Vol. 30, Issue 2 https://doi.org/10.1016/j.pecs.2003.10.004	journal	January 2004
A review on biomass as a fuel for boilers Saidur, R.; Abdelaziz, E. A.; Demirbas, A. Renewable and Sustainable Energy Reviews, Vol. 15, Issue 5 https://doi.org/10.1016/j.rser.2011.02.015	journal	June 2011
Zinc-catalyzed Williamson ether synthesis in the absence of base Paul, Satya; Gupta, Monika Tetrahedron Letters, Vol. 45, Issue 48 https://doi.org/10.1016/j.tetlet.2004.10.009	journal	November 2004
Group Additivity Determination for Oxygenates, Oxonium Ions, and Oxygen-Containing Carbenium Ions Dellon, Lauren D.; Sung, Chun-Yi; Robichaud, David J. Industrial & Engineering Chemistry Research, Vol. 56, Issue 37 https://doi.org/10.1021/acs.iecr.7b02605	journal	September 2017
Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock Schmidt, Stanislaus; Ritter, Benjamin S.; Kratzert, D. Macromolecules, Vol. 49, Issue 19 https://doi.org/10.1021/acs.macromol.6b01485	journal	September 2016
Erythritol Dicarbonate as Intermediate for Solvent- and Isocyanate-Free Tailoring of Bio-Based Polyhydroxyurethane Thermoplastics and Thermoplastic Elastomers Schmidt, Stanislaus; Gatti, Felix J.; Luitz, Manuel Macromolecules, Vol. 50, Issue 6 https://doi.org/10.1021/acs.macromol.6b02787	journal	March 2017
Computational Framework for the Identification of Bioprivileged Molecules Zhou, Xiaowei; Brentzel, Zachary J.; Kraus, George A. ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 2 https://doi.org/10.1021/acssuschemeng.8b05275	journal	December 2018
Transformation of Carbon Dioxide Sakakura, Toshiyasu; Choi, Jun-Chul; Yasuda, Hiroyuki Chemical Reviews, Vol. 107, Issue 6 https://doi.org/10.1021/cr068357u	journal	June 2007
High-temperature stabilities of hydrocarbons Stein, Stephen E.; Fahr, A. The Journal of Physical Chemistry, Vol. 89, Issue 17 https://doi.org/10.1021/j100263a027	journal	August 1985
Catalytic activity of various salts in the reaction of 2,3-epoxypropyl phenyl ether and carbon dioxide under atmospheric pressure Kihara, Nobuhiro; Hara, Nobutaka; Endo, Takeshi The Journal of Organic Chemistry, Vol. 58, Issue 23 https://doi.org/10.1021/jo00075a011	journal	November 1993
Thermodynamic Properties of Ketenes: Group Additivity Values from Quantum Chemical Calculations Sumathi, Raman; Green, William H. The Journal of Physical Chemistry A, Vol. 106, Issue 34 https://doi.org/10.1021/jp021179y	journal	August 2002
Group Additive Values for the Gas Phase Standard Enthalpy of Formation of Hydrocarbons and Hydrocarbon Radicals Sabbe, Maarten K.; Saeys, Mark; Reyniers, Marie-Françoise The Journal of Physical Chemistry A, Vol. 109, Issue 33 https://doi.org/10.1021/jp050484r	journal	August 2005
Thermodynamic Properties (Enthalpy, Bond Energy, Entropy, and Heat Capacity) and Internal Rotor Potentials of Vinyl Alcohol, Methyl Vinyl Ether, and Their Corresponding Radicals da Silva, Gabriel; Kim, Chol-Han; Bozzelli, Joseph W. The Journal of Physical Chemistry A, Vol. 110, Issue 25 https://doi.org/10.1021/jp0602878	journal	June 2006
Thermochemical Properties and Group Values for Nitrogen-Containing Molecules Ashcraft, Robert W.; Green, William H. The Journal of Physical Chemistry A, Vol. 112, Issue 38 https://doi.org/10.1021/jp803759m	journal	September 2008
First Principles Based Group Additive Values for the Gas Phase Standard Entropy and Heat Capacity of Hydrocarbons and Hydrocarbon Radicals Sabbe, Maarten K.; De Vleeschouwer, Freija; Reyniers, Marie-Françoise The Journal of Physical Chemistry A, Vol. 112, Issue 47 https://doi.org/10.1021/jp807526n	journal	November 2008
Synthesis of Alkyl Aryl Ethers by Catalytic Williamson Ether Synthesis with Weak Alkylation Agents Fuhrmann, Edgar; Talbiersky, Jörg Organic Process Research & Development, Vol. 9, Issue 2 https://doi.org/10.1021/op050001h	journal	March 2005
Agriculture: Beyond food versus fuel Graham-Rowe, Duncan Nature, Vol. 474, Issue 7352 https://doi.org/10.1038/474S06a	journal	June 2011
Sugar substitutes, chewing gum and dental caries--a review Edgar, W. M. British Dental Journal, Vol. 184, Issue 1 https://doi.org/10.1038/sj.bdj.4809535	journal	January 1998
Oxygenate, oxyalkyl and alkoxycarbonyl thermochemistry and rates for hydrogen abstraction from oxygenates Sumathi, R.; Green, Jr., William H. Phys. Chem. Chem. Phys., Vol. 5, Issue 16 https://doi.org/10.1039/B307050F	journal	January 2003
Conversion of biomass to selected chemical products Gallezot, Pierre Chem. Soc. Rev., Vol. 41, Issue 4 https://doi.org/10.1039/C1CS15147A	journal	January 2012
α,ω-Di(glycerol carbonate) telechelic polyesters and polyolefins as precursors to polyhydroxyurethanes: an isocyanate-free approach Annunziata, Liana; Diallo, Abdou K.; Fouquay, Stéphane Green Chem., Vol. 16, Issue 4 https://doi.org/10.1039/C3GC41821A	journal	January 2014
Quantitative synthesis of bis(cyclic carbonate)s by iron catalyst for non-isocyanate polyurethane synthesis Sheng, Xingfeng; Ren, Guanjie; Qin, Yusheng Green Chemistry, Vol. 17, Issue 1 https://doi.org/10.1039/C4GC01294A	journal	January 2015
Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s Maisonneuve, Lise; More, Arvind S.; Foltran, Stéphanie RSC Adv., Vol. 4, Issue 49 https://doi.org/10.1039/C4RA03675A	journal	January 2014
Multifunctional β-amino alcohols as bio-based amine curing agents for the isocyanate- and phosgene-free synthesis of 100% bio-based polyhydroxyurethane thermosets Blattmann, H.; Mülhaupt, R. Green Chemistry, Vol. 18, Issue 8 https://doi.org/10.1039/C5GC02563J	journal	January 2016
Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency Sousa, Andreia F.; Vilela, Carla; Fonseca, Ana C. Polymer Chemistry, Vol. 6, Issue 33 https://doi.org/10.1039/C5PY00686D	journal	January 2015
Reprocessable polyhydroxyurethane networks exhibiting full property recovery and concurrent associative and dissociative dynamic chemistry via transcarbamoylation and reversible cyclic carbonate aminolysis Chen, Xi; Li, Lingqiao; Jin, Kailong Polym. Chem., Vol. 8, Issue 41 https://doi.org/10.1039/C7PY01160A	journal	January 2017
Utilisation of CO2 as a chemical feedstock: opportunities and challenges Aresta, Michele; Dibenedetto, Angela Dalton Transactions, Issue 28 https://doi.org/10.1039/b700658f	journal	January 2007
Physisorption and chemisorption of alkanes and alkenes in H-FAU: a combined ab initio–statistical thermodynamics study De Moor, Bart A.; Reyniers, Marie-Françoise; Marin, Guy B. Physical Chemistry Chemical Physics, Vol. 11, Issue 16 https://doi.org/10.1039/b819435c	journal	January 2009
Biomass to biodegradable polymer (PLA) Singhvi, Mamata; Gokhale, Digambar RSC Advances, Vol. 3, Issue 33 https://doi.org/10.1039/c3ra41592a	journal	January 2013
Chemical Kinetic Data Base for Combustion Chemistry. Part I. Methane and Related Compounds Tsang, W.; Hampson, R. F. Journal of Physical and Chemical Reference Data, Vol. 15, Issue 3 https://doi.org/10.1063/1.555759	journal	July 1986
Revised Group Additivity Values for Enthalpies of Formation (at 298 K) of Carbon–Hydrogen and Carbon–Hydrogen–Oxygen Compounds Cohen, N. Journal of Physical and Chemical Reference Data, Vol. 25, Issue 6 https://doi.org/10.1063/1.555988	journal	November 1996
Estimation of Pure-Component Properties from Group-Contributions Joback, K. G.; Reid, R. C. Chemical Engineering Communications, Vol. 57, Issue 1-6 https://doi.org/10.1080/00986448708960487	journal	July 1987
Demand for biomass to meet renewable energy targets in the United States: implications for land use Oliver, Anthony; Khanna, Madhu GCB Bioenergy, Vol. 9, Issue 9 https://doi.org/10.1111/gcbb.12437	journal	April 2017
Oxidation of Methyl-Substituted Naphthalenes: Pathways in a Versatile Sphingomonas paucimobilisStrain Dutta, Tapan K.; Selifonov, Sergey A.; Gunsalus, Irwin C. Applied and Environmental Microbiology, Vol. 64, Issue 5 https://doi.org/10.1128/AEM.64.5.1884-1889.1998	journal	May 1998
Hydrocarbon Bond Dissociation Energies McMillen, D. F.; Golden, D. M. Annual Review of Physical Chemistry, Vol. 33, Issue 1 https://doi.org/10.1146/annurev.pc.33.100182.002425	journal	October 1982
In silico feasibility of novel biodegradation pathways for 1,2,4-trichlorobenzene Finley, Stacey D.; Broadbelt, Linda J.; Hatzimanikatis, Vassily BMC Systems Biology, Vol. 4, Issue 1 https://doi.org/10.1186/1752-0509-4-7	journal	January 2010
Food vs. Fuel: Diversion of Crops Could Cause More Hunger Tenenbaum, David J. Environmental Health Perspectives, Vol. 116, Issue 6 https://doi.org/10.1289/ehp.116-a254	journal	June 2008
Chemicals from Biomass: A Market Assessment of Bioproducts with Near-Term Potential Biddy, Mary J.; Scarlata, Christopher; Kinchin, Christopher https://doi.org/10.2172/1244312	report	March 2016
Analysis of Fossil Fuel Energy Consumption and Environmental Impacts in European Countries Martins, Florinda; Felgueiras, Carlos; Smitkova, Miroslava Energies, Vol. 12, Issue 6 https://doi.org/10.3390/en12060964	journal	March 2019

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