ERIC Number: EJ1448577
Record Type: Journal
Publication Date: 2024-Nov
Pages: 7
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: EISSN-1938-1328
Triazolinedione-Based Cross-Linking of Plant Oils: An Introductory Organic Reactivity Laboratory Experiment
Diederick Maes; Kevin Bevernaege; Kamil Unal; Elias Denijs; Johan M. Winne
Journal of Chemical Education, v101 n11 p4945-4951 2024
An undergraduate laboratory experiment has been developed for the synthesis of a reactive cross-linker that is useful in various highly visual demonstrations of organic reactivity, click chemistry, and biobased polymer synthesis. A triazolinedione-based cross-linker, which is known as a useful reagent for click chemistry, can be obtained from biobased isophorone diisocyanate (IPDI) in three synthetic steps: two steps to elaborate a urazole precursor, and finally a mild oxidation of this urazole to the highly reactive triazolinedione click reagent. As triazolinediones are strong chromophores, the progress of the oxidation step can be visually monitored by the appearance of a bright red-pink color. Students can perform either all three synthetic operations or just the final oxidation step, starting from a prepared batch of the precursor. Alternatively, for less experienced students, the reactive cross-linker or click reagent can be prepared beforehand by a lab assistant and used as such. Students used the freshly prepared click reagent to covalently cross-link various unsaturated plant oils into a polymer network. The gelation of the plant oil into a "plant foil" can be visually monitored, as the bright red-pink color of the cross-linker disappears over time. The purity of the synthesized cross-linking reagent can also be assessed by students by using a simple titration experiment. Students can rely on various practical first and second year undergraduate lab skills, but at the same time, they arrive at a tangible and visual experience of chemical reactivity.
Descriptors: Organic Chemistry, Laboratory Experiments, Undergraduate Study, Science Education, College Science, Science Experiments, Scientific Concepts, Visual Aids, Plants (Botany)
Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A