Assessment of Plant and Microalgal Oil-Derived Nonisocyanate Polyurethane Products for Potential Commercialization

Dong, Tao; Dheressa, Ermias; Wiatrowski, Matthew; Pereira, Andre Prates; Zeller, Ashton; Laurens, Lieve M. L.; Pienkos, Philip T.

doi:10.1021/acssuschemeng.1c03653

Title: Assessment of Plant and Microalgal Oil-Derived Nonisocyanate Polyurethane Products for Potential Commercialization

Journal Article · Wed Sep 15 00:00:00 UTC 2021 · ACS Sustainable Chemistry & Engineering

DOI: https://doi.org/10.1021/acssuschemeng.1c03653 · OSTI ID:1822828

^[1]; Dheressa, Ermias ^[2]; Wiatrowski, Matthew ^[1]; Pereira, Andre Prates ^[3]; Zeller, Ashton ^[4];

^[1]; Pienkos, Philip T. ^[1]

National Renewable Energy Lab. (NREL), Golden, CO (United States)
Intel Corporation, Phoenix, AZ (United States)
University of Bath (United Kingdom)
Algix, Meridian, MI (United States)

Green pathways for nonisocyanate polyurethane (NIPU) production have attracted increasing levels of interest. The reaction between 5-membered cyclic carbonate and polyamines is one of the most promising pathways to produce NIPU polymers. Though promising, major technical hurdles such as slow polymerization rate and poor performance hinder the commercialization of NIPU. In this paper, we screened several commercially available triglyceride oil feedstocks for NIPU products, focusing on polymerization kinetics and product performance for industrial application. The impact of carbonated group density on polymerization rate and mechanical strength was determined. We have demonstrated a remarkably higher reactivity of carbonated oil derived from feedstocks with polyunsaturated fatty acid (PUFA). The NIPU derived from such feedstocks also showed improved performance for industrial application. Unlike traditional polyurethane foam production that uses isocyanate and water to generate CO2 as a blowing reagent, there is no gas formation in NIPU polymerization. We have demonstrated a practical and cost-effective approach to produce NIPU foam material using bicarbonate as a blowing reagent. Furthermore, we conducted the first-ever technoeconomic analysis (TEA), revealing that profitable commercial NIPU production can be achieved when operating at sufficient production capacities.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office; USDOE Office of Technology Transitions (OTT)

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1822828

Report Number(s):: NREL/JA--2800-77638; MainId:29564; UUID:744fe418-1c65-40a2-996b-bcc7cdd2ae05; MainAdminID:62995

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 38 Vol. 9; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (48)

Epoxidation of soybean oil in toluene with peroxoacetic and peroxoformic acids— kinetics and side reactions Petrović, Zoran S.; Zlatanić, Alisa; Lava, Charlene C. European Journal of Lipid Science and Technology, Vol. 104, Issue 5 https://doi.org/10.1002/1438-9312(200205)104:5<293::AID-EJLT293>3.0.CO;2-W	journal	May 2002
Soy-based polyurethanes by nonisocyanate route Javni, Ivan; Hong, Doo Pyo; Petrović, Zoran S. Journal of Applied Polymer Science, Vol. 108, Issue 6 https://doi.org/10.1002/app.27995	journal	January 2008
Polyurethanes from soybean oil, aromatic, and cycloaliphatic diamines by nonisocyanate route Javni, Ivan; Hong, Doo Pyo; Petrović, Zoran S. Journal of Applied Polymer Science, Vol. 128, Issue 1 https://doi.org/10.1002/app.38215	journal	July 2012
The promise and challenges of microalgal-derived biofuels Pienkos, Philip T.; Darzins, Al Biofuels, Bioproducts and Biorefining, Vol. 3, Issue 4 https://doi.org/10.1002/bbb.159	journal	July 2009
From the Synthesis of Biobased Cyclic Carbonate to Polyhydroxyurethanes: A Promising Route towards Renewable Non‐Isocyanate Polyurethanes Carré, Camille; Ecochard, Yvan; Caillol, Sylvain ChemSusChem, Vol. 12, Issue 15 https://doi.org/10.1002/cssc.201900737	journal	June 2019
Synthesis, Characterization, and Selectivity of Bifunctional Couplers: Synthesis, Characterization, and Selectivity … He, Yingchun; Goel, Vishal; Keul, Helmut Macromolecular Chemistry and Physics, Vol. 211, Issue 22 https://doi.org/10.1002/macp.201000340	journal	October 2010
Isocyanate- and Phosgene-Free Routes to Polyfunctional Cyclic Carbonates and Green Polyurethanes by Fixation of Carbon Dioxide Blattmann, Hannes; Fleischer, Maria; Bähr, Moritz Macromolecular Rapid Communications, Vol. 35, Issue 14 https://doi.org/10.1002/marc.201400209	journal	June 2014
Investigation of cooperative kinetics on reactions of functional groups on polymer chains Goldstein, B. N.; Goryunov, A. N.; Gotlib, Yu. Ya. Journal of Polymer Science Part A-2: Polymer Physics, Vol. 9, Issue 5 https://doi.org/10.1002/pol.1971.160090501	journal	May 1971
Model reaction for the synthesis of polyhydroxyurethanes from cyclic carbonates with amines: Substituent effect on the reactivity and selectivity of ring-opening direction in the reaction of five-membered cyclic carbonates with amine Tomita, Hidetoshi; Sanda, Fumio; Endo, Takeshi Journal of Polymer Science Part A: Polymer Chemistry, Vol. 39, Issue 21 https://doi.org/10.1002/pola.10009	journal	January 2001
Polyaddition of bis(seven-membered cyclic carbonate) with diamines: A novel and efficient synthetic method for polyhydroxyurethanes Tomita, Hidetoshi; Sanda, Fumio; Endo, Takeshi Journal of Polymer Science Part A: Polymer Chemistry, Vol. 39, Issue 23 https://doi.org/10.1002/pola.10058	journal	January 2001
Salt effect on polyaddition of bifunctional cyclic carbonate and diamine Ochiai, Bungo; Inoue, Shoko; Endo, Takeshi Journal of Polymer Science Part A: Polymer Chemistry, Vol. 43, Issue 24 https://doi.org/10.1002/pola.21081	journal	January 2005
Accurate and reliable quantification of total microalgal fuel potential as fatty acid methyl esters by in situ transesterification Laurens, Lieve M. L.; Quinn, Matthew; Van Wychen, Stefanie Analytical and Bioanalytical Chemistry, Vol. 403, Issue 1 https://doi.org/10.1007/s00216-012-5814-0	journal	February 2012
Non-isocyanate polyurethane adhesive from sucrose used for particleboard Xi, Xuedong; Wu, Zhigang; Pizzi, Antonio Wood Science and Technology, Vol. 53, Issue 2 https://doi.org/10.1007/s00226-019-01083-2	journal	February 2019
Catalyzed non-isocyanate polyurethane (NIPU) coatings from bio-based poly(cyclic carbonates) Yu, Arvin Z.; Setien, Raul A.; Sahouani, Jonas M. Journal of Coatings Technology and Research, Vol. 16, Issue 1 https://doi.org/10.1007/s11998-018-0135-7	journal	September 2018
Combined algal processing: A novel integrated biorefinery process to produce algal biofuels and bioproducts Dong, Tao; Knoshaug, Eric P.; Davis, Ryan Algal Research, Vol. 19 https://doi.org/10.1016/j.algal.2015.12.021	journal	November 2016
Lipid recovery from wet oleaginous microbial biomass for biofuel production: A critical review Dong, Tao; Knoshaug, Eric P.; Pienkos, Philip T. Applied Energy, Vol. 177 https://doi.org/10.1016/j.apenergy.2016.06.002	journal	September 2016
Green polyurethane from lignin and soybean oil through non-isocyanate reactions Lee, Albert; Deng, Yulin European Polymer Journal, Vol. 63 https://doi.org/10.1016/j.eurpolymj.2014.11.023	journal	February 2015
Novel thermoplastic polyhydroxyurethane elastomers as effective damping materials over broad temperature ranges Beniah, Goliath; Liu, Kun; Heath, William H. European Polymer Journal, Vol. 84 https://doi.org/10.1016/j.eurpolymj.2016.05.031	journal	November 2016
Room temperature flexible isocyanate-free polyurethane foams Cornille, Adrien; Guillet, Camille; Benyahya, Sofia European Polymer Journal, Vol. 84 https://doi.org/10.1016/j.eurpolymj.2016.05.032	journal	November 2016
Promising mechanical and adhesive properties of isocyanate-free poly(hydroxyurethane) Cornille, Adrien; Michaud, Guillaume; Simon, Frédéric European Polymer Journal, Vol. 84 https://doi.org/10.1016/j.eurpolymj.2016.09.048	journal	November 2016
A perspective approach to sustainable routes for non-isocyanate polyurethanes Cornille, Adrien; Auvergne, Rémi; Figovsky, Oleg European Polymer Journal, Vol. 87 https://doi.org/10.1016/j.eurpolymj.2016.11.027	journal	February 2017
Solvent and catalyst-free synthesis of sunflower oil based polyurethane through non-isocyanate route and its coatings properties Doley, Simanta; Dolui, Swapan K. European Polymer Journal, Vol. 102 https://doi.org/10.1016/j.eurpolymj.2018.03.030	journal	May 2018
Condensed tannin-glucose-based NIPU bio-foams of improved fire retardancy Chen, Xinyi; Li, Jinxing; Xi, Xuedong Polymer Degradation and Stability, Vol. 175 https://doi.org/10.1016/j.polymdegradstab.2020.109121	journal	May 2020
Isocyanate-Free Routes to Polyurethanes and Poly(hydroxy Urethane)s Maisonneuve, Lise; Lamarzelle, Océane; Rix, Estelle Chemical Reviews, Vol. 115, Issue 22 https://doi.org/10.1021/acs.chemrev.5b00355	journal	October 2015
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
Non-Isocyanate Polyurethane Thermoplastic Elastomer: Amide-Based Chain Extender Yields Enhanced Nanophase Separation and Properties in Polyhydroxyurethane Beniah, Goliath; Fortman, David J.; Heath, William H. Macromolecules, Vol. 50, Issue 11 https://doi.org/10.1021/acs.macromol.7b00765	journal	May 2017
Poly(hydroxyurethane) Adhesives and Coatings: State-of-the-Art and Future Directions Gomez-Lopez, Alvaro; Panchireddy, Satyannarayana; Grignard, Bruno ACS Sustainable Chemistry & Engineering, Vol. 9, Issue 29 https://doi.org/10.1021/acssuschemeng.1c02558	journal	July 2021
Biobased Reprocessable Polyhydroxyurethane Networks: Full Recovery of Crosslink Density with Three Concurrent Dynamic Chemistries Hu, Sumeng; Chen, Xi; Torkelson, John M. ACS Sustainable Chemistry & Engineering, Vol. 7, Issue 11 https://doi.org/10.1021/acssuschemeng.9b01239	journal	May 2019
On the Versatility of Urethane/Urea Bonds: Reversibility, Blocked Isocyanate, and Non-isocyanate Polyurethane Delebecq, Etienne; Pascault, Jean-Pierre; Boutevin, Bernard Chemical Reviews, Vol. 113, Issue 1 https://doi.org/10.1021/cr300195n	journal	October 2012
Selective esterification to produce microalgal biodiesel and enrich polyunsaturated fatty acid using zeolite as a catalyst Dong, Tao; Yu, Xiaochen; Miao, Chao RSC Advances, Vol. 5, Issue 103 https://doi.org/10.1039/C5RA17512G	journal	January 2015
Non-isocyanate poly(amide-hydroxyurethane)s from sustainable resources Zhang, Keren; Nelson, Ashley M.; Talley, Samantha J. Green Chemistry, Vol. 18, Issue 17 https://doi.org/10.1039/C6GC01096B	journal	January 2016
Linseed and soybean oil-based polyurethanes prepared via the non-isocyanate route and catalytic carbon dioxide conversion Bähr, Moritz; Mülhaupt, Rolf Green Chemistry, Vol. 14, Issue 2 https://doi.org/10.1039/c2gc16230j	journal	January 2012
Cyclic limonene dicarbonate as a new monomer for non-isocyanate oligo- and polyurethanes (NIPU) based upon terpenes Bähr, Moritz; Bitto, Alexandro; Mülhaupt, Rolf Green Chemistry, Vol. 14, Issue 5 https://doi.org/10.1039/c2gc35099h	journal	January 2012
Solubility in CO ₂ and swelling studies by in situIR spectroscopy of vegetable-based epoxidized oils as polyurethane precursors Foltran, Stéphanie; Maisonneuve, Lise; Cloutet, Eric Polym. Chem., Vol. 3, Issue 2 https://doi.org/10.1039/c2py00476c	journal	January 2012
Non-isocyanate polyurethanes: from chemistry to applications Kathalewar, Mukesh S.; Joshi, Padmanabh B.; Sabnis, Anagha S. RSC Advances, Vol. 3, Issue 13 https://doi.org/10.1039/c2ra21938g	journal	January 2013
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
Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors Maisonneuve, Lise; Wirotius, Anne-Laure; Alfos, Carine Polym. Chem., Vol. 5, Issue 21 https://doi.org/10.1039/c4py00922c	journal	January 2014
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
Activated lipidic cyclic carbonates for non-isocyanate polyurethane synthesis Lamarzelle, Océane; Durand, Pierre-Luc; Wirotius, Anne-Laure Polymer Chemistry, Vol. 7, Issue 7 https://doi.org/10.1039/c5py01964h	journal	January 2016
Room temperature synthesis of non-isocyanate polyurethanes (NIPUs) using highly reactive N-substituted 8-membered cyclic carbonates Yuen, Alexander; Bossion, Amaury; Gómez-Bengoa, Enrique Polymer Chemistry, Vol. 7, Issue 11 https://doi.org/10.1039/c6py00264a	journal	January 2016
Waterborne isocyanate-free polyurethane epoxy hybrid coatings synthesized from sustainable fatty acid diamine Zhang, Cheng; Wang, Haoran; Zhou, Qixin Green Chemistry, Vol. 22, Issue 4 https://doi.org/10.1039/c9gc03335a	journal	January 2020
Conceptual Basis and Techno-Economic Modeling for Integrated Algal Biorefinery Conversion of Microalgae to Fuels and Products (2019 NREL TEA Update: Highlighting Paths to Future Cost Goals via a New Pathway for Combined Algal Processing) Davis, Ryan; Wiatrowski, Matthew; Kinchin, Christopher https://doi.org/10.2172/1665822	report	September 2020
Glucose-Biobased Non-Isocyanate Polyurethane Rigid Foams Xi, Xuedong; Pizzi, A.; Gerardin, C. Journal of Renewable Materials, Vol. 7, Issue 3 https://doi.org/10.32604/jrm.2019.04174	journal	January 2019
Organosolv Lignin for Non-Isocyanate Based Polyurethanes (NIPU) as Wood Adhesive Saražin, Jaša; Pizzi, Antonio; Amirou, Siham Journal of Renewable Materials, Vol. 9, Issue 5 https://doi.org/10.32604/jrm.2021.015047	journal	January 2021
Soy Protein Isolate Non-Isocyanates Polyurethanes (NIPU) Wood Adhesives Chen, Xinyi; Pizzi, Antonio; Xi, Xuedong Journal of Renewable Materials, Vol. 9, Issue 6 https://doi.org/10.32604/jrm.2021.015066	journal	January 2021
Isocyanate-Free Polyurethane Coatings and Adhesives from Mono- and Di-Saccharides Xi, Xuedong; Pizzi, Antonio; Delmotte, Luc Polymers, Vol. 10, Issue 4 https://doi.org/10.3390/polym10040402	journal	April 2018
Preparation and Evaluation of Glucose Based Non-Isocyanate Polyurethane Self-Blowing Rigid Foams Xi, Xuedong; Pizzi, Antonio; Gerardin, Christine Polymers, Vol. 11, Issue 11 https://doi.org/10.3390/polym11111802	journal	November 2019
Non-Furanic Humins-Based Non-Isocyanate Polyurethane (NIPU) Thermoset Wood Adhesives Chen, Xinyi; Pizzi, Antonio; Essawy, Hisham Polymers, Vol. 13, Issue 3 https://doi.org/10.3390/polym13030372	journal	January 2021

Similar Records

Developing Microalgae-Based Non-Isocyanate Polyurethane Foam Materials

Conference · Fri Jan 17 00:00:00 UTC 2025 · OSTI ID:2522808

Dong, Tao; Koumans, Helene; Hull, Tobias

Non-isocyanate polyurethane products and methods of making the same

Patent · Tue Nov 21 04:00:00 UTC 2023 · OSTI ID:2293881

Dong, Tao; Pienkos, Philip T.

Control technology overview report: CFC-11 emissions from flexible polyurethane foam manufacturing. Final report, March-October 1986

Technical Report · Fri Jan 01 04:00:00 UTC 1988 · OSTI ID:5482616

Farmer, R W; Nelson, T P

Related Subjects

09 BIOMASS FUELS
algae
biobased polymer
kinetics
non-isocyanate polyurethane
techno economic analysis
vegetable oil

Title: Assessment of Plant and Microalgal Oil-Derived Nonisocyanate Polyurethane Products for Potential Commercialization

Citation Formats

References (48)

Similar Records

Related Subjects