"Bitter" Results: Toward Sustainable Synthesis of the Most Bitter Substances, Denatonium Saccharinate and Denatonium Benzoate, Starting from a Popular Anesthetic, Lidocaine

Autor/inn/en	Stachowiak, Witold; Wysocki, Marcin; Niemczak, Michal
Titel	"Bitter" Results: Toward Sustainable Synthesis of the Most Bitter Substances, Denatonium Saccharinate and Denatonium Benzoate, Starting from a Popular Anesthetic, Lidocaine
Quelle	In: Journal of Chemical Education, 99 (2022) 4, S.1604-1611 (8 Seiten)Infoseite zur Zeitschrift PDF als Volltext Verfügbarkeit
Zusatzinformation	ORCID (Stachowiak, Witold) ORCID (Niemczak, Michal)
Sprache	englisch
Dokumenttyp	gedruckt; online; Zeitschriftenaufsatz
ISSN	0021-9584
DOI	10.1021/acs.jchemed.1c00995
Schlagwörter	Science Instruction; Chemistry; Sustainability; Spectroscopy; Scientific Concepts; Concept Formation + Suchen Sie Ihr Suchwort? Teaching of science; Science education; Natural sciences Lessons; Naturwissenschaftlicher Unterricht; Chemie; Nachhaltigkeit; Spektroskopie; Concept learning; Begriffsbildung
Abstract	One of the most important aspects associated with the modern production of chemicals is sustainability. To teach students and young scientists to design their research in the spirit of "sustainable development," students should be made accustomed to seeking solutions that are not only efficient and cost-effective but also safe and environmentally friendly. However, it is still a great challenge to select appropriate material for a lecture that, in addition to providing educational aspects, will simultaneously attract students' attention. Therefore, to make learning more accessible and inspiring, it is worth using known molecules with interesting properties, such as denatonium salts, as the main product of the developed sustainable process. In this particular project, lidocaine was alkylated with benzyl chloride in the presence of a catalyst and subsequently subjected to an ion exchange reaction. This path resulted in the formation of two organic salts, denatonium benzoate and denatonium saccharinate, which are considered the most bitter substances currently known to mankind. Additionally, their syntheses were optimized according to "green chemistry" principles, and subsequently, the structures of the products were identified via spectroscopic methods (FTIR and NMR spectroscopies). Finally, determination of basic physicochemical parameters (solubility in water and octanol-water partition coefficient), according to OECD guidelines, enabled the assessment of the potential impact of these compounds on the natural environment. (As Provided).
Anmerkungen	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
Erfasst von	ERIC (Education Resources Information Center), Washington, DC
Update	2024/1/01