Ionic Liquids Derived from Vitamin C as Multifunctional Active Ingredients for Sustainable Stored-Product Management

Michał Niemczak , Damian Krystian Kaczmarek , Tomasz Klejdysz , Daniela Gwiazdowska , Katarzyna Marchwińska , Juliusz Pernak

Abstract

This study is focused on the utilization of naturally occurring ascorbic acid (vitamin C) in the synthesis of biologically inspired ionic liquids with attractive application potential. The ionic liquids with the ascorbate anion were obtained in high yield (>90%) via a simple, “green” two-step procedure using well-known, cost-effective, and commercially available alkyltrimethylammonium, dialkyldimethylammonium, and alkylmethylbis(2-hydroxyethyl)ammonium cations. Three positive ions in this group used for syntheses are derived from renewable resources, such as vegetable oil or animal fat. The study confirmed the strong influence of the chemical structure of the cation on the stability of the compounds obtained in the air, as well as in aqueous solutions. In addition, the synthesized ionic forms of vitamin C exhibited very good antibacterial and antifungal properties against different microorganisms, including pathogens. The tests also revealed the excellent or good deterrent activity toward common stored-grain insects (granary weevil, confused flour beetle, and khapra beetle), reaching the values determined for azadirachtin, known as the reference antifeedant. The best results were achieved with products containing two long alkyl substituents in the cation (dimethyldioctylammonium and didecyldimethylammonium) that proved to be extremely effective against all the organisms tested. The results of the biological activity indicate that the products synthesized belong to the third generation of ionic liquids. In conclusion, ascorbate-based ionic liquids with multifunctional (antibacterial, antifungal, antifeedant, and antioxidant) properties have substantial potential to be used in the storage of crop protection products.
Author Michał Niemczak - Politechnika Poznańska (PP)
Michał Niemczak,,
-
, Damian Krystian Kaczmarek - Politechnika Poznańska
Damian Krystian Kaczmarek,,
-
, Tomasz Klejdysz - Instytut Ochrony Roślin Państwowego Instytutu Badawczego w Poznaniu
Tomasz Klejdysz,,
-
, Daniela Gwiazdowska (WT / KPPJ)
Daniela Gwiazdowska,,
- Department of Natural Science and Quality Assurance
, Katarzyna Marchwińska (WT / KPPJ)
Katarzyna Marchwińska,,
- Department of Natural Science and Quality Assurance
, Juliusz Pernak - Politechnika Poznańska
Juliusz Pernak,,
-
Journal seriesACS Sustainable Chemistry & Engineering, ISSN 2168-0485, (N/A 140 pkt)
Issue year2019
Vol7
No1
Pages1072-1084
Publication size in sheets0.6
Keywords in EnglishAscorbic acid, Feeding deterrents, Fungicides, Ionic liquids, Stored grain protection
ASJC Classification1500 General Chemical Engineering; 1600 General Chemistry; 2105 Renewable Energy, Sustainability and the Environment; 2304 Environmental Chemistry
DOIDOI:10.1021/acssuschemeng.8b04696
URL https://pubs.acs.org/doi/10.1021/acssuschemeng.8b04696#
Languageen angielski
Score (nominal)140
Score sourcejournalList
ScoreMinisterial score = 140.0, 03-04-2020, ArticleFromJournal
Publication indicators WoS Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 1.371; WoS Impact Factor: 2018 = 6.97 (2) - 2018=7.185 (5)
Citation count*
Additional fields
UwagiFirst online: 30 November 2018
Cite
Share Share

Get link to the record


* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
Back
Confirmation
Are you sure?