Plant Oil‐Based Long‐Chain C26 Monomers and Their Polymers
Abstract
The self‐metathesis of erucic acid with ruthenium‐based catalysts, followed by the hydrogenation of the double bond, yielded 1,26‐hexacosanedioic acid (AA). Polycondensation of this biobased long‐chain α,ω‐dicarboxylic acid with hexacosane‐1,26‐diol (BB), generated from the former by reduction, yielded the polyester 26,26. Monomer AA was also polymerized with short‐chain alkanediols, namely dodecane‐1,12‐diol and butane‐1,4‐diol, generating polyesters 12,26 and 4,26, respectively. The properties of these aliphatic polyesters were investigated by various techniques, revealing high crystallinity, melting, and degradation temperatures, depending on the monomers used. These materials are an attractive alternative to fossil resource‐based polymeric materials.
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SGP of plant oils derived diols and diacids with > 20 methylene sequences generates polyesters with structures and thermal properties reminiscent of PE.
“For example, SGP of plant oils derived diols and diacids with > 20 methylene sequences generates polyesters with structures and thermal properties reminiscent of PE. 213”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [213]
A few studies using Bi(OTf)3 to polymerize plant oil- and suberin-derived long-chain fatty acids generated highly crystalline polyesters with high melting and degradation temperatures as attractive alternatives to petroleum-based polyolefins.
“A few studies using Bi(OTf)3 to polymerize plant oil-237 and suberin-derived 238 long-chain fatty acids generated highly crystalline polyesters with high melting and degradation temperatures as attractive alternatives to petroleum-based polyolefins.”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [237]
Cites
Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts
Garber, S. B., Kingsbury, J. S., Gray, B. L., & Hoveyda, A. H. (2000) · Journal of the American Chemical Society · doi:10.1021/ja001179g · Cited by 2,020 · see citing works
Plant oil renewable resources as green alternatives in polymer science
Meier, M. A. R., Metzger, J. O., & Schubert, U. S. (2007) · Chemical Society Reviews · doi:10.1039/b703294c · Cited by 1,487 · see citing works
Self-citationPolyurethanes from Vegetable Oils
Petrovìć, Z. S. (2008) · Journal of macromolecular science. Part C, Reviews in macromolecular chemistry and physics/Journal of macromolecular science. Reviews in macromolecular chemistry and physics · doi:10.1080/15583720701834224 · Cited by 933 · see citing works
Vegetable oil-based polymeric materials: synthesis, properties, and applications
Xia, Y., & Larock, R. C. (2010) · Green Chemistry · doi:10.1039/c0gc00264j · Cited by 864 · see citing works
Polymers from triglyceride oils
Güner, F. S., Yağcı, Y., & Erciyes, A. T. (2006) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.07.001 · Cited by 787 · see citing works
Gandini, A. (2011) · Green Chemistry · doi:10.1039/c0gc00789g · Cited by 695 · see citing works
Prevention of Undesirable Isomerization during Olefin Metathesis
Hong, S. H., Sanders, D. P., Lee, C. W., & Grubbs, R. H. (2005) · Journal of the American Chemical Society · doi:10.1021/ja052939w · Cited by 648 · see citing works
Plant oils: The perfect renewable resource for polymer science?!
de Espinosa, L. M., & Meier, M. A. R. (2010) · European Polymer Journal · doi:10.1016/j.eurpolymj.2010.11.020 · Cited by 646 · see citing works
Self-citationModern Polyesters: Chemistry and Technology of Polyesters and Copolyesters
(2004) · Wiley eBooks · doi:10.1002/0470090685 · Cited by 590 · see citing works
Plant Oils as Platform Chemicals for Polyurethane Synthesis: Current State-of-the-Art
Lligadas, G., Ronda, J. C., Galià, M., & Cádiz, V. (2010) · Biomacromolecules · doi:10.1021/bm100839x · Cited by 436 · see citing works
Lu, Y., & Larock, R. C. (2009) · ChemSusChem · doi:10.1002/cssc.200800241 · Cited by 324 · see citing works
Condensation polymers from natural oils
Sharma, V. K., & Kundu, P. P. (2008) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2008.07.004 · Cited by 299 · see citing works
Acyclic dienemetathesis: a versatile tool for the construction of defined polymer architectures
Mutlu, H., de Espinosa, L. M., & Meier, M. A. R. (2010) · Chemical Society Reviews · doi:10.1039/b924852h · Cited by 296 · see citing works
Self-citationTEM Studies of Platinum Nanowires Fabricated in Mesoporous Silica MCM-41
Liu, Z. P., Sakamoto, Y., Ohsuna, T., Hiraga, K., Terasaki, O., Ko, C. H., Shin, H. J., & Ryoo, R. (2000) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20000901)39:17 · Cited by 232 · see citing works
Linear Semicrystalline Polyesters from Fatty Acids by Complete Feedstock Molecule Utilization
Quinzler, D., & Mecking, S. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.201001510 · Cited by 211 · see citing works
Application of olefin metathesis in oleochemistry: an example of green chemistry
Mol, J. C. (2002) · Green Chemistry · doi:10.1039/b109896a · Cited by 207 · see citing works
Stempfle, F., Quinzler, D., Heckler, I., & Mecking, S. (2011) · Macromolecules · doi:10.1021/ma200627e · Cited by 203 · see citing works
Fats and oils as renewable feedstock for chemistry
Metzger, J. O. (2009) · European Journal of Lipid Science and Technology · doi:10.1002/ejlt.200900130 · Cited by 195 · see citing works
Vegetable oil‐based thermosetting polymers
Galià, M., de Espinosa, L. M., Ronda, J. C., Lligadas, G., & Cádiz, V. (2009) · European Journal of Lipid Science and Technology · doi:10.1002/ejlt.200900096 · Cited by 195 · see citing works
Polymers and surfactants on the basis of renewable resources
Warwel, S., Brüse, F., Demes, C., Kunz, M., & Klaas, M. R. G. (2001) · Chemosphere · doi:10.1016/s0045-6535(00)00322-2 · Cited by 183 · see citing works
Metathesis as a versatile tool in oleochemistry
Rybak, A., Fokou, P. A., & Meier, M. A. R. (2008) · European Journal of Lipid Science and Technology · doi:10.1002/ejlt.200800027 · Cited by 174 · see citing works
Self-citationMeier, M. A. R. (2009) · Macromolecular Chemistry and Physics · doi:10.1002/macp.200900168 · Cited by 157 · see citing works
Self-citationBiodegradable products by lipase biocatalysis
Linko, Y., Lämsä, M., Wu, X., Uosukainen, E., Seppälä, J. V., & Linko, P. (1998) · Journal of Biotechnology · doi:10.1016/s0168-1656(98)00155-2 · Cited by 156 · see citing works
Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils
Mol, J. C. (2004) · Topics in Catalysis · doi:10.1023/b:toca.0000013544.89226.c4 · Cited by 135 · see citing works
Unsaturated PA X,20 from Renewable Resources via Metathesis and Catalytic Amidation
Mutlu, H., & Meier, M. A. R. (2009) · Macromolecular Chemistry and Physics · doi:10.1002/macp.200900045 · Cited by 116 · see citing works
Self-citationMaterials from Vegetable Oils: Major Sources, Properties and Applications
Belgacem, M. N., & Gandini, A. (2008) · Elsevier eBooks · doi:10.1016/b978-0-08-045316-3.00003-x · Cited by 116 · see citing works
Metathesis of unsaturated fatty acids: Synthesis of long‐chain unsaturated‐α,ω‐dicarboxylic acids
Ngo, H. L., Jones, K. C., & Foglia, T. A. (2006) · Journal of the American Oil Chemists Society · doi:10.1007/s11746-006-1249-0 · Cited by 110 · see citing works
Lipophilic Extractives of the Inner and Outer Barks of Eucalyptus globulus
Freire, C. S. R., Silvestre, A. J. D., Neto, C. P., et al. (2002) · Holzforschung · doi:10.1515/hf.2002.059 · Cited by 102 · see citing works
Self-citationTwo-Step Biocatalytic Route to Biobased Functional Polyesters from ω-Carboxy Fatty Acids and Diols
Yang, Y., Lu, W., Zhang, X., Xie, W., Cai, M., & Gross, R. A. (2009) · Biomacromolecules · doi:10.1021/bm901112m · Cited by 96 · see citing works
Aliphatic Long‐Chain C20 Polyesters from Olefin Metathesis
Trzaskowski, J., Quinzler, D., Bährle, C., & Mecking, S. (2011) · Macromolecular Rapid Communications · doi:10.1002/marc.201100319 · Cited by 96 · see citing works
Anwer, M. K., Sherman, D., Roney, J. G., et al. (1989) · The Journal of Organic Chemistry · doi:10.1021/jo00267a012 · Cited by 85 · see citing works
A Chemical Route to High Molecular Weight Vegetable Oil-Based Polyhydroxyalkanoate
Petrovìć, Z. S., Milić, J., Xu, Y., & Cvetković, I. (2010) · Macromolecules · doi:10.1021/ma100294r · Cited by 65 · see citing works
Warwel, S., Demes, C., & Steinke, G. (2001) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.1137 · Cited by 62 · see citing works
Dam, P. B. V., Mittelmeijer, M. C., & Boelhouwer, C. (1974) · Journal of the American Oil Chemists Society · doi:10.1007/bf02635013 · Cited by 61 · see citing works
Discovery of Carbohydrate Sulfotransferase Inhibitors from a Kinase-Directed Library
Armstrong, J. I., Portley, A. R., Chang, Y., Nierengarten, D. M., Cook, B. N., Bowman, K. G., Bishop, A., Gray, N. S., Shokat, K. M., Schultz, P. G., et al. (2000) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(20000403)39:7 · Cited by 61 · see citing works
Buzin, P., Lahcini, M., Schwarz, G., & Kricheldorf, H. R. (2008) · Macromolecules · doi:10.1021/ma8017662 · Cited by 59 · see citing works
Djigoué, G. B., & Meier, M. A. R. (2009) · Applied Catalysis A General · doi:10.1016/j.apcata.2009.08.025 · Cited by 55 · see citing works
Self-citationNovel suberin‐based biopolyesters: From synthesis to properties
Sousa, A. F., Gandini, A., Silvestre, A. J. D., Neto, C. P., Cruz Pinto, J. J. C., Eckerman, C., & Holmbom, B. (2011) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/pola.24661 · Cited by 53 · see citing works
Self-citationDevelopment of Biobased Unsaturated Polyester Containing Functionalized Linseed Oil
Miyagawa, H., Mohanty, A. K., Burgueño, R., et al. (2006) · Industrial & Engineering Chemistry Research · doi:10.1021/ie050902e · Cited by 50 · see citing works
Polyethylene like polymers. Aliphatic polyesters of dodecanedioic acid
Barbiroli, G., Lorenzetti, C., Berti, C., Fiorini, M., & Manaresi, P. (2003) · European Polymer Journal · doi:10.1016/s0014-3057(02)00280-x · Cited by 42 · see citing works
Tortosa, K., Hamaide, T., Boisson, C., & Spitz, R. (2001) · Macromolecular Chemistry and Physics · doi:10.1002/1521-3935(20010401)202:7 · Cited by 42 · see citing works
Caminiti, R., PANDOLFI, L., & Ballirano, P. (2000) · Journal of Macromolecular Science Part B · doi:10.1081/mb-100100400 · Cited by 35 · see citing works
Synthesis of aliphatic suberin-like polyesters by ecofriendly catalytic systems
Sousa, A. F., Silvestre, A. J. D., Gandini, A., & Neto, C. P. (2012) · High Performance Polymers · doi:10.1177/0954008311431114 · Cited by 29 · see citing works
Self-citationCho, I., & Lee, K. (1997) · Macromolecular Chemistry and Physics · doi:10.1002/macp.1997.021980316 · Cited by 22 · see citing works
Temperature‐induced phase transition of poly(N,N‐dimethylaminoethyl methacrylate‐co‐acrylamide)
Cho, S. H., Jhon, M. S., Yuk, S. H., et al. (1997) · Journal of Polymer Science Part B Polymer Physics · doi:10.1002/(sici)1099-0488(199703)35:4 · Cited by 2 · see citing works
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Zhang, X., Fevre, M., Jones, G. O., & Waymouth, R. M. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00329 · Cited by 936 · see citing works
The quest for sustainable polyesters – insights into the future
Vilela, C., Sousa, A. F., Fonseca, A. C., Serra, A. C., Coelho, J. F. J., Freire, C. S. R., & Silvestre, A. J. D. (2014) · Polym. Chem. · doi:10.1039/c3py01213a · Cited by 527 · see citing works
Self-citationBio-based polyesters: Recent progress and future prospects
Zhang, Q., Song, M., Xu, Y., Wang, W., Wang, Z., & Zhang, L. (2021) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2021.101430 · Cited by 433 · see citing works
Stempfle, F., Ortmann, P., & Mecking, S. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00705 · Cited by 397 · see citing works
Structure–properties relationship of fatty acid-based thermoplastics as synthetic polymer mimics
Maisonneuve, L., Lebarbé, T., Grau, E., & Cramail, H. (2013) · Polymer Chemistry · doi:10.1039/c3py00791j · Cited by 220 · see citing works
From Polyethylene to Polyester: Influence of Ester Groups on the Physical Properties
Pepels, M. P. F., Hansen, M. R., Goossens, H., & Duchateau, R. (2013) · Macromolecules · doi:10.1021/ma401403x · Cited by 113 · see citing works
Self-metathesis of fatty acid methyl esters: full conversion by choosing the appropriate plant oil
Mutlu, H., Hofsäß, R., Montenegro, R. E., & Meier, M. A. R. (2013) · RSC Advances · doi:10.1039/c3ra40330k · Cited by 77 · see citing works
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- Authors
- Vilela, C., Silvestre, A. J. D., & Meier, M. A. R.
- Affiliations
- Karlsruhe Institute of Technology (DE)
- University of Aveiro (PT)
- Venue
- Macromolecular Chemistry and Physics
- Publisher
- Wiley
- Published
- 2012-08-31
- Volume
- 213
- Issue
- 21
- Pages
- 2220-2227
- ISSN
- 1022-1352 (ISSN-L)
- 1521-3935
- OpenAlex
- W2067049331
- Cited by
- 85
- References
- 45
- Citations by year
- 2026: 2 · 2025: 5 · 2024: 9 · 2023: 1 · 2022: 2 · 2021: 8 · 2020: 2 · 2019: 4 · 2018: 4 · 2017: 7 · 2016: 7 · 2015: 10 · 2014: 13 · 2013: 10 · 2012: 1
- FWCI
- 4.41
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Macromolecular Chemistry and Physics (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
- Keywords
- erucic acid, self-metathesis, ruthenium catalysts, aliphatic polyesters, polycondensation, alkanediols, crystallinity, thermal degradation, bio-based polymers
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