PMID- 36364264
OWN - NLM
STAT- MEDLINE
DCOM- 20221114
LR  - 20221117
IS  - 1420-3049 (Electronic)
IS  - 1420-3049 (Linking)
VI  - 27
IP  - 21
DP  - 2022 Nov 1
TI  - Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for 
      Quaternization Reactions.
LID - 10.3390/molecules27217429 [doi]
LID - 7429
AB  - The Menshutkin reaction represents the alkylation of tertiary amines by alkyl 
      halide where the reactants are neutral and the products, quaternary ammonium 
      salts, are two ions with opposite signs. The most commonly used organic solvents 
      in quaternization reactions are volatile organic solvents (VOSs), namely acetone, 
      anhydrous benzene, dry dichloromethane (DCM), dimethylformamide (DMF) and 
      acetonitrile (ACN). The purpose of this work was to examine eutectic solvents as 
      a "greener" alternative to conventional solvents so that quaternization reactions 
      take place in accordance with the principles of green chemistry. Herein, sixteen 
      eutectic solvents were used as replacements for volatile organic ones in 
      quaternization reactions of isonicotinamide with substituted phenacyl bromides. 
      The reactions were carried out at 80  degrees C by three synthetic approaches: 
      conventional (4-6 h), microwave (20 min) and ultrasound (3 h). Microwave-assisted 
      organic reactions produced the highest yields, where in several reactions, the 
      yield was almost quantitative. The most suitable eutectic solvents were based on 
      choline chloride (ChCl) as the hydrogen bond acceptor (HBA) and glycerol, oxalic 
      or levulinic acid as hydrogen bond donors (HBDs). The benefits of these three 
      deep eutectic solvents (DESs) as a medium for quaternization reactions are the 
      simplicity of their preparation for large-scale production, with inexpensive, 
      available and nontoxic starting materials, as well as their biodegradability.
FAU - Busic, Valentina
AU  - Busic V
AD  - Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, 
      Josip Juraj Strossmayer University of Osijek, 31000 Osijek, Croatia.
FAU - Molnar, Maja
AU  - Molnar M
AUID- ORCID: 0000-0002-1258-9962
AD  - Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, 
      Josip Juraj Strossmayer University of Osijek, 31000 Osijek, Croatia.
FAU - Tomicic, Vice
AU  - Tomicic V
AD  - Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, 
      Josip Juraj Strossmayer University of Osijek, 31000 Osijek, Croatia.
FAU - Bozanovic, Dalia
AU  - Bozanovic D
AD  - Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, 
      Josip Juraj Strossmayer University of Osijek, 31000 Osijek, Croatia.
FAU - Jerkovic, Igor
AU  - Jerkovic I
AUID- ORCID: 0000-0002-0727-6662
AD  - Faculty of Chemistry and Technology, University of Split, 21000 Split, Croatia.
FAU - Gaso-Sokac, Dajana
AU  - Gaso-Sokac D
AD  - Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, 
      Josip Juraj Strossmayer University of Osijek, 31000 Osijek, Croatia.
LA  - eng
GR  - UIP-2017-05-6593/Croatian Science Foundation and the Green Technologies in 
      Synthesis of Heterocyclic Compounds Project/
PT  - Journal Article
DEP - 20221101
PL  - Switzerland
TA  - Molecules
JT  - Molecules (Basel, Switzerland)
JID - 100964009
RN  - N91BDP6H0X (Choline)
RN  - 0 (Deep Eutectic Solvents)
RN  - 0 (Solvents)
RN  - PDC6A3C0OX (Glycerol)
SB  - IM
MH  - *Choline/chemistry
MH  - *Deep Eutectic Solvents
MH  - Solvents/chemistry
MH  - Glycerol/chemistry
MH  - Hydrogen Bonding
PMC - PMC9655353
OTO - NOTNLM
OT  - deep eutectic solvents
OT  - isonicotinamide salts
OT  - microwave synthesis
OT  - ultrasound synthesis
COIS- The authors declare no conflict of interest.
EDAT- 2022/11/12 06:00
MHDA- 2022/11/15 06:00
PMCR- 2022/11/01
CRDT- 2022/11/11 01:41
PHST- 2022/09/06 00:00 [received]
PHST- 2022/10/28 00:00 [revised]
PHST- 2022/10/29 00:00 [accepted]
PHST- 2022/11/11 01:41 [entrez]
PHST- 2022/11/12 06:00 [pubmed]
PHST- 2022/11/15 06:00 [medline]
PHST- 2022/11/01 00:00 [pmc-release]
AID - molecules27217429 [pii]
AID - molecules-27-07429 [pii]
AID - 10.3390/molecules27217429 [doi]
PST - epublish
SO  - Molecules. 2022 Nov 1;27(21):7429. doi: 10.3390/molecules27217429.