Exploring Divergent Green Reaction Media for the Copolymerization of Biobased Monomers in the Teaching Laboratory
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 it...
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| Veröffentlicht in: | Journal of chemical education 2021-02, Vol.98 (2), p.559-566 |
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| creator | Gormong, Ethan A Wentzel, Michael T Cao, Boen Kundel, Laura N Reineke, Theresa M Wissinger, Jane E |
| description | 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 (M n), 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. |
| doi_str_mv | 10.1021/acs.jchemed.0c00688 |
| format | Article |
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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 (M n), 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.</description><identifier>ISSN: 0021-9584</identifier><identifier>EISSN: 1938-1328</identifier><identifier>DOI: 10.1021/acs.jchemed.0c00688</identifier><language>eng</language><publisher>Easton: American Chemical Society and Division of Chemical Education, Inc</publisher><subject>Bulk polymerization ; Chemical synthesis ; College Science ; Concept Formation ; Copolymerization ; Copolymers ; Crosslinking ; Elastomers ; Experiments ; Green chemistry ; Inhalants ; Laboratory Experiments ; Laboratory tests ; Monomers ; NMR spectroscopy ; Organic Chemistry ; Organic solvents ; Physical properties ; Plastics ; Polarity ; Polymerization ; Polymers ; Quantitative analysis ; Science Experiments ; Science Instruction ; Science Laboratories ; Scientific Concepts ; Solvents ; Spectroscopy ; Swelling ; Undergraduate Study ; Writing instruction</subject><ispartof>Journal of chemical education, 2021-02, Vol.98 (2), p.559-566</ispartof><rights>2020 American Chemical Society and Division of Chemical Education, Inc.</rights><rights>Copyright American Chemical Society Feb 9, 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a339t-9fcf2b9dc68b390f5464f350fdb9f5daabc61e08b4d153ee0f0f85727883adfd3</citedby><cites>FETCH-LOGICAL-a339t-9fcf2b9dc68b390f5464f350fdb9f5daabc61e08b4d153ee0f0f85727883adfd3</cites><orcidid>0000-0001-7020-3450 ; 0000-0002-1148-2717 ; 0000-0002-9240-3629</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jchemed.0c00688$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jchemed.0c00688$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttp://eric.ed.gov/ERICWebPortal/detail?accno=EJ1287124$$DView record in ERIC$$Hfree_for_read</backlink></links><search><creatorcontrib>Gormong, Ethan A</creatorcontrib><creatorcontrib>Wentzel, Michael T</creatorcontrib><creatorcontrib>Cao, Boen</creatorcontrib><creatorcontrib>Kundel, Laura N</creatorcontrib><creatorcontrib>Reineke, Theresa M</creatorcontrib><creatorcontrib>Wissinger, Jane E</creatorcontrib><title>Exploring Divergent Green Reaction Media for the Copolymerization of Biobased Monomers in the Teaching Laboratory</title><title>Journal of chemical education</title><addtitle>J. Chem. Educ</addtitle><description>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 (M n), 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.</description><subject>Bulk polymerization</subject><subject>Chemical synthesis</subject><subject>College Science</subject><subject>Concept Formation</subject><subject>Copolymerization</subject><subject>Copolymers</subject><subject>Crosslinking</subject><subject>Elastomers</subject><subject>Experiments</subject><subject>Green chemistry</subject><subject>Inhalants</subject><subject>Laboratory Experiments</subject><subject>Laboratory tests</subject><subject>Monomers</subject><subject>NMR spectroscopy</subject><subject>Organic Chemistry</subject><subject>Organic solvents</subject><subject>Physical properties</subject><subject>Plastics</subject><subject>Polarity</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Quantitative analysis</subject><subject>Science Experiments</subject><subject>Science Instruction</subject><subject>Science Laboratories</subject><subject>Scientific Concepts</subject><subject>Solvents</subject><subject>Spectroscopy</subject><subject>Swelling</subject><subject>Undergraduate Study</subject><subject>Writing instruction</subject><issn>0021-9584</issn><issn>1938-1328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kE1PAjEURRujiYj-AmPSxPVAP2aYdqmIqIGYGFxPOu0rDIEptoMRf72FQZeu3uLec19yELqmpEcJo32lQ2-pF7AG0yOakIEQJ6hDJRcJ5Uycog6JtURmIj1HFyEsCaEsk6KDPkZfm5XzVT3HD9Un-DnUDR57gBq_gdJN5Wo8BVMpbJ3HzQLw0G3carcGX32rQ-wsvq9cqQIYPHW1i1HAVX0oz-LGYj8-UaXzqnF-d4nOrFoFuDreLnp_HM2GT8nkdfw8vJskinPZJNJqy0pp9ECUXBKbpYPU8oxYU0qbGaVKPaBARJkamnEAYokVWc5yIbgy1vAuum13N959bCE0xdJtfR1fFiyVOaOCkDy2eNvS3oXgwRYbX62V3xWUFHu3RXRbHN0WR7eRummpaEH_EaMXykROWRrzfpsf4N-3_y3-AAwli1k</recordid><startdate>20210209</startdate><enddate>20210209</enddate><creator>Gormong, Ethan A</creator><creator>Wentzel, Michael T</creator><creator>Cao, Boen</creator><creator>Kundel, Laura N</creator><creator>Reineke, Theresa M</creator><creator>Wissinger, Jane E</creator><general>American Chemical Society and Division of Chemical Education, Inc</general><general>Division of Chemical Education, Inc</general><general>American Chemical Society</general><scope>7SW</scope><scope>BJH</scope><scope>BNH</scope><scope>BNI</scope><scope>BNJ</scope><scope>BNO</scope><scope>ERI</scope><scope>PET</scope><scope>REK</scope><scope>WWN</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><orcidid>https://orcid.org/0000-0001-7020-3450</orcidid><orcidid>https://orcid.org/0000-0002-1148-2717</orcidid><orcidid>https://orcid.org/0000-0002-9240-3629</orcidid></search><sort><creationdate>20210209</creationdate><title>Exploring Divergent Green Reaction Media for the Copolymerization of Biobased Monomers in the Teaching Laboratory</title><author>Gormong, Ethan A ; 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Chem. Educ</addtitle><date>2021-02-09</date><risdate>2021</risdate><volume>98</volume><issue>2</issue><spage>559</spage><epage>566</epage><pages>559-566</pages><issn>0021-9584</issn><eissn>1938-1328</eissn><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. 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| subjects | Bulk polymerization Chemical synthesis College Science Concept Formation Copolymerization Copolymers Crosslinking Elastomers Experiments Green chemistry Inhalants Laboratory Experiments Laboratory tests Monomers NMR spectroscopy Organic Chemistry Organic solvents Physical properties Plastics Polarity Polymerization Polymers Quantitative analysis Science Experiments Science Instruction Science Laboratories Scientific Concepts Solvents Spectroscopy Swelling Undergraduate Study Writing instruction |
| title | Exploring Divergent Green Reaction Media for the Copolymerization of Biobased Monomers in the Teaching Laboratory |
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