(+)-Limonene-Lactam: Synthesis of a Sustainable Monomer for Ring-Opening Polymerization to Novel, Biobased Polyamides.
limonene
polyamides
ring-opening polymerizations (ROP)
sustainable polymers
terpenes
Journal
Macromolecular rapid communications
ISSN: 1521-3927
Titre abrégé: Macromol Rapid Commun
Pays: Germany
ID NLM: 9888239
Informations de publication
Date de publication:
Sep 2022
Sep 2022
Historique:
revised:
22
04
2022
received:
25
02
2022
pubmed:
10
5
2022
medline:
9
9
2022
entrez:
9
5
2022
Statut:
ppublish
Résumé
In this work, the synthesis of limonene lactam starting from limonene epoxide and its subsequent ring-opening polymerization (ROP) to novel polyamides is presented. Sustainable, biobased materials are gaining interest as replacements of conventional, petroleum-based materials, and even more important, as high-performance materials for new applications. Terpenes-structurally advanced biobased compounds-are therefore of great interest. In this research, limonene lactam, a novel biobased monomer for preparing sustainable polyamides via ROP, can be synthesized. Limonene lactam possesses an isopropylene and a methyl side group, thus stereocenters posing special challenges and requirements for synthesis, analysis and polymerization. However, these difficult-to-synthesize structural elements can generate novel polymers with unique properties, e.g., functionalizability. In this work, a sustainable monomer synthesis is established, and simplified to industrial needs. For the sterically demanding in-bulk ROP to limonene polyamides, various initiators and conditions are tested. Polyamides with more than 100 monomer units are successfully synthesized and confirmed via nuclear magnetic resonance (NMR) spectroscopy and gel permeations chromatography (GPC). Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) are used to analyze its thermal properties. In summary, a sustainable monomer synthesis is established, and promising polyamides with intact double bond and interesting thermal properties are achieved.
Identifiants
pubmed: 35531966
doi: 10.1002/marc.202200185
doi:
Substances chimiques
Lactams
0
Nylons
0
Terpenes
0
Limonene
9MC3I34447
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2200185Subventions
Organisme : Deutsche Forschungsgemeinschaft
Organisme : 445011287
Informations de copyright
© 2022 The Authors. Macromolecular Rapid Communications published by Wiley-VCH GmbH.
Références
P. T. Anastas, J. C. Warner, J. C. Warner, Green Chemistry. Theory and Practice, Oxford University Press, Oxford 1998.
P. Anastas, N. Eghbali, Chem. Soc. Rev. 2010, 39, 301.
R. A. Sheldon, Green Chem. 2014, 16, 950.
S. A. Miller, ACS Macro Lett. 2013, 2, 550.
M. Winnacker, B. Rieger, Macromol. Rapid Commun. 2016, 37, 1391.
R. Mülhaupt, Macromol. Chem. Phys. 2013, 214, 159.
M. Richter, L. Vieira, V. Sieber, Chem Sus Chem. 2021, 14, 251.
R. M. Cywar, N. A. Rorrer, C. B. Hoyt, G. T. Beckham, E. Y.-X. Chen, Nat. Rev. Mater. 2022, 7, 83.
K. Yao, C. Tang, Macromolecules 2013, 46, 1689.
M. R. Thomsett, T. E. Storr, O. R. Monaghan, R. A. Stockman, S. M. Howdle, Green Mater. 2016, 4, 115.
J. Zhao, H. Schlaad, Adv. Polym. Sci. 2013, 253, 151.
D. H. Lamparelli, M. Winnacker, C. Capacchione, ChemPlusChem 2021, 87, 202100366.
M. Winnacker, B. Rieger, ChemSusChem 2015, 8, 2455.
F. Della Monica, A. W. Kleij, Polym. Chem. 2020, 11, 5109.
A. J. Silvestre, A. Gandini, in Monomers, Polymers and Composites from Renewable Resources (Eds: M. N. Belgacem, A. Gandini), Elsevier, Oxford 2008, p. 17-38.
K. Satoh, A. Nakahara, K. Mukunoki, H. Sugiyama, H. Saito, M. Kamigaito, Polym. Chem. 2014, 5, 3222.
M. A. Hillmyer, W. B. Tolman, Acc. Chem. Res. 2014, 47, 2390.
A. Stamm, J. Öhlin, C. Mosbech, P. Olsén, B. Guo, E. Söderberg, A. Biundo, L. Fogelström, S. Bhattacharyya, U. T. Bornscheuer, E. Malmström, P.-O. Syrén, JACS Au 2021, 1, 1949.
Merchant Research & Consulting Ltd, D-Limonene Is a Prospective Substitute for Some Petroleum-Based Chemicals, 2015, can be found under https://mcgroup.co.uk/news/20151224/dlimonene-prospective-substitute-petroleumbased-chemicals.html
A. Causero, C. Troll, B. Rieger, Ind. Eng. Chem. Res. 2020, 59, 15464.
O. Hauenstein, M. Reiter, S. Agarwal, B. Rieger, A. Greiner, Green Chem. 2016, 18, 760.
F. Auriemma, C. De Rosa, M. R. Di Caprio, R. Di Girolamo, W. C. Ellis, G. W. Coates, Angew. Chem., Int. Ed. 2015, 54, 1215.
O. Hauenstein, S. Agarwal, A. Greiner, Nat. Commun. 2016, 7, 11862.
M. Firdaus, M. A. R. Meier, Green Chem. 2013, 15, 370.
M. R. Thomsett, J. C. Moore, A. Buchard, R. A. Stockman, S. M. Howdle, Green Chem. 2019, 21, 149.
A. Gandini, T. M. Lacerda, A. J. F. Carvalho, E. Trovatti, Chem. Rev. 2016, 116, 1637.
P. Wu, X. Wang, R. Shi, H. Cheng, F. Zhao, Green Chem. 2022, 24, 1561.
K. Marchildon, Macromol. React. Eng. 2011, 5, 22.
M. Kyulavska, N. Toncheva-Moncheva, J. Rydz, Handbook of Ecomaterials, Springer, Berlin, Heidelberg 2019, p. 2901.
S. Russo, E. Casazza, Polymer Science: A Comprehensive Overview (Eds: M. Moeller, K. Matyjaszewski), Elsevier, Amsterdam, 2012, p. 4.
M. Winnacker, M. Neumeier, X. Zhang, C. M. Papadakis, B. Rieger, Macromol. Rapid Commun. 2016, 37, 851.
M. Winnacker, S. Vagin, V. Auer, B. Rieger, Macromol. Chem. Phys. 2014, 215, 1654.
M. Winnacker, A. Tischner, M. Neumeier, B. Rieger, RSC Adv. 2015, 5, 77699.
M. Winnacker, J. Sag, Chem. Commun. 2018, 54, 841.
M. Winnacker, A. J. G. Beringer, T. F. Gronauer, H. H. Güngör, L. Reinschlüssel, B. Rieger, S. A. Sieber, Macromol. Rapid Commun. 2019, 40, 1900091.
H. K. Hall, J. Org. Chem. 1963, 28, 3213.
P. N. Stockmann, D. L. Pastoetter, M. Woelbing, C. Falcke, M. Winnacker, H. Strittmatter, V. Sieber, Macromol. Rapid Commun. 2019, 40, 1800903.
P. N. Stockmann, D. Van Opdenbosch, A. Poethig, D. L. Pastoetter, M. Hoehenberger, S. Lessig, J. Raab, M. Woelbing, C. Falcke, M. Winnacker, C. Zollfrank, H. Strittmatter, V. Sieber, Nat. Commun. 2020, 11, 509.
M. M. Kleybolte, M. Winnacker, Macromol. Rapid Commun. 2021, 42, 2100065.
P. S. Löser, P. Rauthe, M. A. R. Meier, A. Llevot, Philos. Trans. R. Soc. A 2020, 378, 20190267.
S. S. Stradling, D. Hornick, J. Lee, J. Riley, J. Chem. Educ. 1983, 60, 502.
A. Zabźa, C. Wawrzeńczyk, H. Kuczyński, Bull. Acad. Pol. Sci. 1972, 1972, 631.
M. Winnacker, A. Tischner, M. Neumeier, B. Rieger, in New Insights into Synthesis and Oligomerization of e-Lactams Derived from the Ketone (-)-Menthone., vol. 5, RSC Advances 2015, p. 77699-77705.
M. Winnacker, J. Sag, A. Tischner, B. Rieger, Macromol. Rapid Commun. 2017, 38, 1600787.
S. Neumann, S. B. Däbritz, S. E. Fritze, L.-C. Leitner, A. Anand, A. Greiner, S. Agarwal, Polym. Chem. 2021, 12, 903.
C. Dauwe, Chromatographic Science Series, 91, Dekker, New York, 2004.
S. Y. Tang, R. A. Bourne, R. L. Smith, M. Poliakoff, Green Chem. 2008, 10, 268.
M. J.-L. Tschan, R. M. Gauvin, C. M. Thomas, Chem. Soc. Rev. 2021, 50, 13587.