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Article


Title

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

Authors

[ 1 ] Wydział Technologii Chemicznej, Politechnika Poznańska | [ 2 ] Instytut Technologii i Inżynierii Chemicznej, Wydział Technologii Chemicznej, Politechnika Poznańska | [ SzD ] doctoral school student | [ P ] employee

Scientific discipline (Law 2.0)

[6.5] Chemical sciences

Year of publication

2022

Published in

Journal of Chemical Education

Journal year: 2022 | Journal volume: vol. 99 | Journal number: iss. 4

Article type

scientific article

Publication language

english

Keywords
EN
  • First-Year Undergraduate/General
  • Second-Year Undergraduate
  • Green Chemistry
  • Problem Solving/Decision Making
  • Alkylation
  • Spectroscopy
  • Precipitation/Solubility
  • Physical Properties
  • Environmental Chemistry
Abstract

EN 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.

Date of online publication

30.03.2022

Pages (from - to)

1604 - 1611

DOI

10.1021/acs.jchemed.1c00995

URL

https://pubs.acs.org/doi/abs/10.1021/acs.jchemed.1c00995

License type

CC BY (attribution alone)

Open Access Mode

publisher's website

Open Access Text Version

final published version

Release date

30.03.2022

Date of Open Access to the publication

at the time of publication

Points of MNiSW / journal

70.0

Impact Factor

2.979 [List 2020]

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