The DOI matches its Crossref record; 65 of the 65 references it cites were found in a registry or an index.
Synthesis of Polyurethanes Using Organocatalysis: A Perspective
Open accessAbstract
Abstract Organocatalysis has become an invaluable tool for polymer synthesis, and its utility has been demonstrated in ring-opening, anionic, zwitterionic, and group-transfer polymerizations. Despite this, the use of organocatalysis in other polymerization reactions such as step-growth polymerizations remains underexplored, relative to more traditional metal-based polymerizations. Recently, the use of organic bases such as guanidines, amidines, N-heterocyclic carbenes, and organic “strong or super-strong” Brønsted acids to catalyze the synthesis of metal-free polyurethanes has shown to be competitive to commercially widely used dibutyltin dilaurate and dibutyltin diacetate catalysts. This Perspective article highlights recent advances in organocatalyst design for isocyanate-based polyurethane synthesis with the aim of comparing the activity and selectivity of each of the new catalytic reactions to each other and the traditional metal-based catalysts. The article also draws attention to new trends in isocyanate-free polyurethane synthesis and the key role that organocatalysis is playing in these innovative polymerization processes.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Hehre, W. J., Ditchfield, R., & Pople, J. A. (1972) · The Journal of Chemical Physics · doi:10.1063/1.1677527 · Cited by 15,855
Ditchfield, R., Hehre, W. J., & Pople, J. A. (1971) · The Journal of Chemical Physics · doi:10.1063/1.1674902 · Cited by 10,612
An overview of N-heterocyclic carbenes
Hopkinson, M. N., Richter, C., Schedler, M., & Glorius, F. (2014) · Nature · doi:10.1038/nature13384 · Cited by 4,264
Bourissou, D., Guerret, O., Gabbaï, F. P., & Bertrand, G. (2000) · Chemical Reviews · doi:10.1021/cr940472u · Cited by 3,633
Organocatalysis by N-Heterocyclic Carbenes
Enders, D., Niemeier, O., & Henseler, A. (2007) · Chemical Reviews · doi:10.1021/cr068372z · Cited by 3,059
Structural engineering of polyurethane coatings for high performance applications
Chattopadhyay, D. K., & Raju, K. V. S. N. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.05.003 · Cited by 1,836
Thermal stability and flame retardancy of polyurethanes
Chattopadhyay, D. K., & Webster, D. C. (2009) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2009.06.002 · Cited by 1,748
Synthesis of cyclic carbonates from epoxides and CO2
North, M., Pasquale, R., & Young, C. (2010) · Green Chemistry · doi:10.1039/c0gc00065e · Cited by 1,361
Delebecq, E., Pascault, J.-P., Boutevin, B., & Ganachaud, F. (2013) · Chemical Reviews · doi:10.1021/cr300195n · Cited by 1,326
Polyurethanes: Versatile Materials and Sustainable Problem Solvers for Today’s Challenges
Engels, H., Pirkl, H., Albers, R., Albach, R. W., Krause, J., Hoffmann, A., Casselmann, H., & Dormish, J. (2013) · Angewandte Chemie International Edition · doi:10.1002/anie.201302766 · Cited by 1,234
Kaljurand, I., Kütt, A., Sooväli, L., Rodima, T., Mäemets, V., Leito, I., & Koppel, I. A. (2005) · The Journal of Organic Chemistry · doi:10.1021/jo048252w · Cited by 962
Organocatalysis: Opportunities and Challenges for Polymer Synthesis
Kiesewetter, M. K., Shin, E. J., Hedrick, J. L., & Waymouth, R. M. (2010) · Macromolecules · doi:10.1021/ma9025948 · Cited by 907
Self-citationOrganic Catalysis for Ring-Opening Polymerization
Dove, A. P. (2012) · ACS Macro Letters · doi:10.1021/mz3005956 · Cited by 541
Fèvre, M., Pinaud, J., Gnanou, Y., Vignolle, J., & Taton, D. (2013) · Chemical Society Reviews · doi:10.1039/c2cs35383k · Cited by 532
Self-citationSustainable routes to polyurethane precursors
Kreye, O., Mutlu, H., & Meier, M. A. R. (2013) · Green Chemistry · doi:10.1039/c3gc40440d · Cited by 416
Non-isocyanate polyurethanes: from chemistry to applications
Kathalewar, M. S., Joshi, P. B., Sabnis, A. S., & Malshe, V. C. (2013) · RSC Advances · doi:10.1039/c2ra21938g · Cited by 414
von der Assen, N., & Bardow, A. (2014) · Green Chem. · doi:10.1039/c4gc00513a · Cited by 399
From Petrochemical Polyurethanes to Biobased Polyhydroxyurethanes
Nohra, B., Candy, L., Blanco, J.-F., Guerin, C., Raoul, Y., & Mouloungui, Z. (2013) · Macromolecules · doi:10.1021/ma400197c · Cited by 395
Carbon dioxide (CO 2 ) as sustainable feedstock for polyurethane production
Langanke, J., Wolf, A., Hofmann, J., Böhm, K., Subhani, M. A., Müller, T. E., Leitner, W., & Gürtler, C. (2014) · Green Chem. · doi:10.1039/c3gc41788c · Cited by 361
Blattmann, H., Fleischer, M., Bähr, M., & Mülhaupt, R. (2014) · Macromolecular Rapid Communications · doi:10.1002/marc.201400209 · Cited by 339
Green synthesis of flexible polyurethane foams from liquefied lignin
Cinelli, P., Anguillesi, I., & Lazzeri, A. (2013) · European Polymer Journal · doi:10.1016/j.eurpolymj.2013.04.005 · Cited by 282
Rational investigations in the ring opening of cyclic carbonates by amines
Blain, M., Jean-Gérard, L., Auvergne, R., Benazet, D., Caillol, S., & Andrioletti, B. (2014) · Green Chem. · doi:10.1039/c4gc01032a · Cited by 220
Cyclic Guanidine Organic Catalysts: What Is Magic About Triazabicyclodecene?
Kiesewetter, M. K., Scholten, M. D., Kirn, N., Weber, R. L., Hedrick, J. L., & Waymouth, R. M. (2009) · The Journal of Organic Chemistry · doi:10.1021/jo902369g · Cited by 215
Self-citationMespouille, L., Coulembier, O., Kawalec, M., Dove, A. P., & Dubois, P. (2014) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2014.02.003 · Cited by 209
Mechanistic considerations of guanidine-catalyzed reactions
Fu, X., & Tan, C. (2011) · Chemical Communications · doi:10.1039/c0cc03691a · Cited by 201
Synthesis of isosorbide based polyurethanes: An isocyanate free method
Besse, V., Auvergne, R., Carlotti, S., Boutevin, G., Otazaghine, B., Caillol, S., Pascault, J.-P., & Boutevin, B. (2013) · Reactive and Functional Polymers · doi:10.1016/j.reactfunctpolym.2013.01.002 · Cited by 194
Polyaddition behavior of bis(five- and six-membered cyclic carbonate)s with diamine
Tomita, H., Sanda, F., & Endo, T. (2001) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/1099-0518(20010315)39:6<860::aid-pola1059>3.0.co;2-2 · Cited by 184
Novel fatty acid based di-isocyanates towards the synthesis of thermoplastic polyurethanes
More, A. S., Lebarbé, T., Maisonneuve, L., Gadenne, B., Alfos, C., & Cramail, H. (2013) · European Polymer Journal · doi:10.1016/j.eurpolymj.2012.12.013 · Cited by 171
Self-citationOrganocatalytic synthesis of (poly)hydroxyurethanes from cyclic carbonates and amines
Lambeth, R. H., & Henderson, T. J. (2013) · Polymer · doi:10.1016/j.polymer.2013.08.053 · Cited by 166
Sardón, H., Irusta, L., Fernandez-Berridi, M. J., Lansalot, M., & Bourgeat‐Lami, É. (2010) · Polymer · doi:10.1016/j.polymer.2010.08.035 · Cited by 151
N-Heterocyclic carbenes as organocatalysts for polymerizations: trends and frontiers
Naumann, S., & Dove, A. P. (2015) · Polymer Chemistry · doi:10.1039/c5py00145e · Cited by 146
Reactivity of secondary amines for the synthesis of non-isocyanate polyurethanes
Camara, F., Benyahya, S., Besse, V., Boutevin, G., Auvergne, R., Boutevin, B., & Caillol, S. (2014) · European Polymer Journal · doi:10.1016/j.eurpolymj.2014.03.011 · Cited by 145
Unverferth, M., Kreye, O., Prohammer, A., & Meier, M. A. R. (2013) · Macromolecular Rapid Communications · doi:10.1002/marc.201300503 · Cited by 143
Organocatalysis Paradigm Revisited: Are Metal-Free Catalysts Really Harmless?
Nachtergael, A., Coulembier, O., Dúbois, P., Helvenstein, M., Duez, P., Blankert, B., & Mespouille, L. (2014) · Biomacromolecules · doi:10.1021/bm5015443 · Cited by 143
Hélou, M., Carpentier, J., & Guillaume, S. M. (2010) · Green Chemistry · doi:10.1039/c0gc00686f · Cited by 129
Naumann, S., & Buchmeiser, M. R. (2014) · Catalysis Science & Technology · doi:10.1039/c4cy00344f · Cited by 129
Maisonneuve, L., Wirotius, A., Alfos, C., Grau, É., & Cramail, H. (2014) · Polymer Chemistry · doi:10.1039/c4py00922c · Cited by 119
Self-citationThe role of catalysis in the synthesis of polyurethane foams based on renewable raw materials
Dworakowska, S., Bogdał, D., Zaccheria, F., & Ravasio, N. (2013) · Catalysis Today · doi:10.1016/j.cattod.2013.11.054 · Cited by 117
Unexpected efficiency of cyclic amidine catalysts in depolymerizing poly(ethylene terephthalate)
Fukushima, K., Coady, D. J., Jones, G. O., Al‐Megren, H. A., Alabdulrahman, A. M., Alsewailem, F. D., Horn, H. W., Rice, J. E., & Hedrick, J. L. (2013) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.26530 · Cited by 115
Self-citationSusperrégui, N., Delcroix, D., Martín-Vaca, B. M., Bourissou, D., & Maron, L. (2010) · The Journal of Organic Chemistry · doi:10.1021/jo101346t · Cited by 113
Sardón, H., Engler, A. C., Chan, J. M. W., García, J. M., Coady, D. J., Pascual, A., Mecerreyes, D., Jones, G. O., Rice, J. E., Horn, H. W., et al. (2013) · Journal of the American Chemical Society · doi:10.1021/ja408641g · Cited by 113
Self-citationMaisonneuve, L., More, A. S., Foltran, S., Alfos, C., Robert, F., Landais, Y., Tassaing, T., Grau, É., & Cramail, H. (2014) · RSC Advances · doi:10.1039/c4ra03675a · Cited by 111
Self-citationWell‐defined Biobased Segmented Polyureas Synthesis via a TBD‐catalyzed Isocyanate‐free Route
Tang, D., Mulder, D. J., Noordover, B. A. J., & Koning, C. E. (2011) · Macromolecular Rapid Communications · doi:10.1002/marc.201100223 · Cited by 110
Latent and Delayed Action Polymerization Systems
Naumann, S., & Buchmeiser, M. R. (2014) · Macromolecular Rapid Communications · doi:10.1002/marc.201300898 · Cited by 98
Polymerizing Base Sensitive Cyclic Carbonates Using Acid Catalysis
Coady, D. J., Horn, H. W., Jones, G. O., Sardón, H., Engler, A. C., Waymouth, R. M., Rice, J. E., Yang, Y. Y., & Hedrick, J. L. (2013) · ACS Macro Letters · doi:10.1021/mz3006523 · Cited by 97
Self-citationCyclic Guanidines as Efficient Organocatalysts for the Synthesis of Polyurethanes
Alsarraf, J., Ammar, Y. A., Robert, F., Cloutet, É., Cramail, H., & Landais, Y. (2012) · Macromolecules · doi:10.1021/ma2026258 · Cited by 96
Self-citationEngler, A. C., Chan, J. M. W., Coady, D. J., O’Brien, J. M., Sardón, H., Nelson, A., Sanders, D. P., Yang, Y. Y., & Hedrick, J. L. (2013) · Macromolecules · doi:10.1021/ma4001258 · Cited by 86
Self-citationAccess to nonisocyanate poly(thio)urethanes: A comparative study
Besse, V., Foyer, G., Auvergne, R., Caillol, S., & Boutevin, B. (2013) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.26722 · Cited by 79
Schwetlick, K., Noack, R., & Stebner, F. (1994) · Journal of the Chemical Society Perkin Transactions 2 · doi:10.1039/p29940000599 · Cited by 68
Cationic Ring-Opening Polymerization of Tetramethylene Urethane
Kušan, J., Keul, H., & Höcker, H. (2001) · Macromolecules · doi:10.1021/ma000535c · Cited by 66
Cationic Ring-Opening Polymerization of Trimethylene Urethane: A Mechanistic Study
Neffgen, S., Keul, H., & Höcker, H. (1997) · Macromolecules · doi:10.1021/ma9610774 · Cited by 65
Neffgen, S., Keul, H., & Höcker, H. (1996) · Macromolecular Rapid Communications · doi:10.1002/marc.1996.030170602 · Cited by 65
Bio‐Based Aliphatic Polyurethanes Through ADMET Polymerization in Bulk and Green Solvent
Lebarbé, T., More, A. S., Sane, P. S., Grau, É., Alfos, C., & Cramail, H. (2013) · Macromolecular Rapid Communications · doi:10.1002/marc.201300695 · Cited by 65
Self-citationVanparijs, N., Maji, S., Louage, B., Voorhaar, L., Laplace, D., Zhang, Q., Shi, Y., Hennink, W. E., Hoogenboom, R., & Geest, B. G. D. (2014) · Polymer Chemistry · doi:10.1039/c4py01224k · Cited by 64
Cooke, G. M., Forsyth, D. S., Bondy, G. S., Tachon, R., Tague, B., & Coady, L. (2008) · Journal of Toxicology and Environmental Health · doi:10.1080/15287390701801653 · Cited by 58
N-Heterocyclic carbene-catalysed synthesis of polyurethanes
Coutelier, O., Ezzi, M. E., Destarac, M., Bonnette, F., Kato, T., Baceiredo, A., Sivasankarapillai, G., Gnanou, Y., & Taton, D. (2012) · Polymer Chemistry · doi:10.1039/c2py00477a · Cited by 58
Self-citationHomogeneous isocyanate- and catalyst-free synthesis of polyurethanes in aqueous media
Sardón, H., Engler, A. C., Chan, J. M. W., Coady, D. J., O’Brien, J. M., Mecerreyes, D., Yang, Y. Y., & Hedrick, J. L. (2013) · Green Chemistry · doi:10.1039/c3gc40319j · Cited by 58
Self-citationPolycarbonate-Based Brush Polymers with Detachable Disulfide-Linked Side Chains
Engler, A. C., Chan, J. M. W., Fukushima, K., Coady, D. J., Yang, Y. Y., & Hedrick, J. L. (2013) · ACS Macro Letters · doi:10.1021/mz400069u · Cited by 52
Self-citationSardón, H., Chan, J. M. W., Ono, R. J., Mecerreyes, D., & Hedrick, J. L. (2014) · Polymer Chemistry · doi:10.1039/c4py00262h · Cited by 49
Self-citationOrganocatalyzed Ring-Opening Polymerizations
Fevre, M., Vignolle, J., Gnanou, Y., & Taton, D. (2012) · Elsevier eBooks · doi:10.1016/b978-0-444-53349-4.00119-9 · Cited by 42
Self-citationChan, J. M. W., Sardón, H., Engler, A. C., García, J. M., & Hedrick, J. L. (2013) · ACS Macro Letters · doi:10.1021/mz400334j · Cited by 33
Self-citationSanders, D. P., Coady, D. J., Yasumoto, M., Fujiwara, M., Sardón, H., & Hedrick, J. L. (2013) · Polymer Chemistry · doi:10.1039/c3py01128c · Cited by 28
Self-citationThe reaction of o-hydroxybenzyl alcohol with phenyl isocyanate in polar solvents
Han, Y. D., Yang, P., Li, J. Y., Qiao, C. D., & Li, T. D. (2010) · Reaction Kinetics Mechanisms and Catalysis · doi:10.1007/s11144-010-0202-2 · Cited by 27
Polyurethane-coated silica particles with broad-spectrum antibacterial properties
Xu, Q., Sardón, H., Chan, J. M. W., Hedrick, J. L., & Yang, Y. Y. (2015) · Polymer Chemistry · doi:10.1039/c4py01455c · Cited by 23
Self-citationSmith, C. A., Cramail, H., & Tassaing, T. (2014) · ChemCatChem · doi:10.1002/cctc.201301002 · Cited by 9
Self-citation
Cited by
Approaches to Sustainable and Continually Recyclable Cross-Linked Polymers
Fortman, D. J., Brutman, J. P., De Hoe, G. X., Snyder, R. L., Dichtel, W. R., & Hillmyer, M. A. (2018) · ACS Sustainable Chemistry & Engineering · doi:10.1021/acssuschemeng.8b02355 · Cited by 559
A perspective approach to sustainable routes for non-isocyanate polyurethanes
Cornille, A., Auvergne, R., Figovsky, O., Boutevin, B., & Caillol, S. (2017) · European Polymer Journal · doi:10.1016/j.eurpolymj.2016.11.027 · Cited by 531
Polymerization of Polar Monomers Mediated by Main-Group Lewis Acid–Base Pairs
Hong, M., Chen, J., & Chen, E. Y.-X. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00352 · Cited by 320
Hong, M., & Chen, E. Y. ‐. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201601092 · Cited by 259
Design, printing, and engineering of regenerative biomaterials for personalized bone healthcare
Jia, Z., Xu, X., Zhu, D., & Zheng, Y. (2023) · Progress in Materials Science · doi:10.1016/j.pmatsci.2023.101072 · Cited by 176
Metadata
- Authors
- Sardon, H., Pascual, A., Mecerreyes, D., Taton, D., Cramail, H., & Hedrick, J. L.
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2015-05-06
- Volume
- 48
- Issue
- 10
- Pages
- 3153-3165
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W2283770533
- Cited by
- 326
- References
- 65
- FWCI
- 14.68
- Type
- journal article
- Language
- en
- Open access
- hybrid
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.