Exploring Divergent Green Reaction Media for the Copolymerization of Biobased Monomers in the Teaching Laboratory

Ethan A Gormong; Michael T. Wentzel; Boen Cao; Laura N. Kundel; Theresa M. Reineke; Jane E. Wissinger

doi:10.1021/acs.jchemed.0c00688

Exploring Divergent Green Reaction Media for the Copolymerization of Biobased Monomers in the Teaching Laboratory

Ethan A Gormong, Michael T. Wentzel, Boen Cao, Laura N. Kundel, Theresa M. Reineke, Jane E. Wissinger

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Polymerization reaction media can have a profound effect on the physical properties of the resultant polymer. This phenomenon is showcased in a new experiment for the organic chemistry and polymer science teaching laboratories wherein the radical copolymerization of biobased β-myrcene and dibutyl itaconate is performed using a nonhazardous aqueous emulsion solvent and compared to a bulk reaction. Both procedures demonstrate multiple green chemistry principles and application to sustainable polymer synthesis. The emulsion copolymerization produces a tacky, elastomeric cross-linked material, capable of swelling to many times its original volume in organic solvents, setting the stage for the exploration of the relationship between solvent polarity and swelling capacity. Conversely, the polymerization of β-myrcene and dibutyl itaconate in the bulk yields a viscous non-cross-linked polymer whose 1H NMR spectrum is suitable for student analysis and estimation of polymer number-average molar mass (Mn), monomer conversion, and copolymer composition. This inexpensive experiment models the use of renewable feedstocks, the effect of reaction medium on polymer architecture, the unique properties of cross-linked organogels, and the quantitative analysis of polymer structure using 1H NMR spectroscopy.

Original language	English (US)
Pages (from-to)	559-566
Number of pages	8
Journal	Journal of Chemical Education
Volume	98
Issue number	2
DOIs	https://doi.org/10.1021/acs.jchemed.0c00688
State	Published - Feb 9 2021

Bibliographical note

Funding Information:
This work was funded by the NSF Center for Sustainable Polymers (CHE-1901635). The authors would like to thank Letitia Yao for her assistance in NMR spectra acquisition. The authors would also like to thank Mckenna Hanson for her suggestions and assistance in the spring 2020 polymer course trial.

Publisher Copyright:
© 2021 American Chemical Society. All rights reserved.

Keywords

Green Chemistry
Hands-On Learning/Manipulatives
Laboratory Instruction
Materials Science
NMR Spectroscopy
Organic Chemistry
Polymer Chemistry
Polymerization
Second-Year Undergraduate
Upper-Division Undergraduate

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10.1021/acs.jchemed.0c00688

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abstract = "Polymerization reaction media can have a profound effect on the physical properties of the resultant polymer. This phenomenon is showcased in a new experiment for the organic chemistry and polymer science teaching laboratories wherein the radical copolymerization of biobased β-myrcene and dibutyl itaconate is performed using a nonhazardous aqueous emulsion solvent and compared to a bulk reaction. Both procedures demonstrate multiple green chemistry principles and application to sustainable polymer synthesis. The emulsion copolymerization produces a tacky, elastomeric cross-linked material, capable of swelling to many times its original volume in organic solvents, setting the stage for the exploration of the relationship between solvent polarity and swelling capacity. Conversely, the polymerization of β-myrcene and dibutyl itaconate in the bulk yields a viscous non-cross-linked polymer whose 1H NMR spectrum is suitable for student analysis and estimation of polymer number-average molar mass (Mn), monomer conversion, and copolymer composition. This inexpensive experiment models the use of renewable feedstocks, the effect of reaction medium on polymer architecture, the unique properties of cross-linked organogels, and the quantitative analysis of polymer structure using 1H NMR spectroscopy.",

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note = "Funding Information: This work was funded by the NSF Center for Sustainable Polymers (CHE-1901635). The authors would like to thank Letitia Yao for her assistance in NMR spectra acquisition. The authors would also like to thank Mckenna Hanson for her suggestions and assistance in the spring 2020 polymer course trial. Publisher Copyright: {\textcopyright} 2021 American Chemical Society. All rights reserved.",

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N2 - Polymerization reaction media can have a profound effect on the physical properties of the resultant polymer. This phenomenon is showcased in a new experiment for the organic chemistry and polymer science teaching laboratories wherein the radical copolymerization of biobased β-myrcene and dibutyl itaconate is performed using a nonhazardous aqueous emulsion solvent and compared to a bulk reaction. Both procedures demonstrate multiple green chemistry principles and application to sustainable polymer synthesis. The emulsion copolymerization produces a tacky, elastomeric cross-linked material, capable of swelling to many times its original volume in organic solvents, setting the stage for the exploration of the relationship between solvent polarity and swelling capacity. Conversely, the polymerization of β-myrcene and dibutyl itaconate in the bulk yields a viscous non-cross-linked polymer whose 1H NMR spectrum is suitable for student analysis and estimation of polymer number-average molar mass (Mn), monomer conversion, and copolymer composition. This inexpensive experiment models the use of renewable feedstocks, the effect of reaction medium on polymer architecture, the unique properties of cross-linked organogels, and the quantitative analysis of polymer structure using 1H NMR spectroscopy.

AB - Polymerization reaction media can have a profound effect on the physical properties of the resultant polymer. This phenomenon is showcased in a new experiment for the organic chemistry and polymer science teaching laboratories wherein the radical copolymerization of biobased β-myrcene and dibutyl itaconate is performed using a nonhazardous aqueous emulsion solvent and compared to a bulk reaction. Both procedures demonstrate multiple green chemistry principles and application to sustainable polymer synthesis. The emulsion copolymerization produces a tacky, elastomeric cross-linked material, capable of swelling to many times its original volume in organic solvents, setting the stage for the exploration of the relationship between solvent polarity and swelling capacity. Conversely, the polymerization of β-myrcene and dibutyl itaconate in the bulk yields a viscous non-cross-linked polymer whose 1H NMR spectrum is suitable for student analysis and estimation of polymer number-average molar mass (Mn), monomer conversion, and copolymer composition. This inexpensive experiment models the use of renewable feedstocks, the effect of reaction medium on polymer architecture, the unique properties of cross-linked organogels, and the quantitative analysis of polymer structure using 1H NMR spectroscopy.

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Exploring Divergent Green Reaction Media for the Copolymerization of Biobased Monomers in the Teaching Laboratory

Abstract

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