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On the synthesis of 3-cyano-6-hydroxy-4-methyl-2-pyridone at room temperature

O sintezi 3-cijano-6-hidroksi-4-metil-2-piridona na sobnoj temperaturi

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2019
0351-94651903229Z.pdf (291.4Kb)
Authors
Zdujić, Miodrag
Petrović, Slobodan
Valentić, Nataša
Mijin, Dušan
Article (Published version)
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Abstract
Milling of cyanoacetamide and acetoacetic ester as reactants, in the presence of KOH as the catalyst and ethanol as a viscous control agent (VCA) was performed in a planetary ball mill with the goal of investigating the effect of mechanochemical treatment for the synthesis of 3-cyano-6hydroxy-4-methyl-2-pyridone at room temperature. The mechanochemical synthesis was performed under various milling parameters, i.e. milling time up to 4 h, number and size of balls, angular velocity as well as molar ratio of reactants and the amount of catalyst. The obtained product was characterized by m.p., UV, IR and NMR data. It was fond that the dominant process parameter is the milling time while others are of less importance. The highest isolated yield after milling was up to 56%. The combination of milling and aging increase yield over 60%.
Mlevenje cijanoacetoamida (2) i acetsirćetnog estra (1) kao reaktanata, u prisustvu KOH kao katalizatora i etanola kao agensa kojim se kontroliše viskoznost, izvedeno je u planetarnom mlinu radi ispitivanja mogućnosti mehanohemijske sinteze 3-cijano-6-hidroksi-4-metil-2-piridona (3) na sobnoj temperaturi. Mehanohemijski tretman je izveden sa različitim parametrima mlevenja: vremenom mlevenja do 4 h, različitom veličinom i brojem kuglica, različitom brzinom obrtanja, kao i različitim molarnim odnosom reaktanata i katalizatora. Dobijeni proizvod je okarakterisan određivanjem temperature topljenja, UV, IR i NMR analizama. Nađeno je da je dominantni procesni parametar vreme mlevenja, dok su ostali od manjeg uticaja. Najveći prinos izolovanog proizvoda je oko 56%, dok se naknadnim "odležavanjem" prinos povećava preko 60%.
Keywords:
cyanoacetamide / acetoacetic ester / mechanochemical synthesis / planetary ball mill / optimization / cijanoacetamid / acetsirćetni estar / mehanohemijska sinteza / planetarni mlin sa kuglama / optimizacija
Source:
Zaštita materijala, 2019, 60, 3, 229-236
Publisher:
  • Engineering Society for Corrosion, Belgrade, Serbia
Funding / projects:
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
  • Nanostructured Functional and Composite Materials in Catalytic and Sorption Processes (RS-45001)

DOI: 10.5937/zasmat1903229Z

ISSN: 0351-9465

[ Google Scholar ]
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4278
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Zdujić, Miodrag
AU  - Petrović, Slobodan
AU  - Valentić, Nataša
AU  - Mijin, Dušan
PY  - 2019
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4278
AB  - Milling of cyanoacetamide and acetoacetic ester as reactants, in the presence of KOH as the catalyst and ethanol as a viscous control agent (VCA) was performed in a planetary ball mill with the goal of investigating the effect of mechanochemical treatment for the synthesis of 3-cyano-6hydroxy-4-methyl-2-pyridone at room temperature. The mechanochemical synthesis was performed under various milling parameters, i.e. milling time up to 4 h, number and size of balls, angular velocity as well as molar ratio of reactants and the amount of catalyst. The obtained product was characterized by m.p., UV, IR and NMR data. It was fond that the dominant process parameter is the milling time while others are of less importance. The highest isolated yield after milling was up to 56%. The combination of milling and aging increase yield over 60%.
AB  - Mlevenje cijanoacetoamida (2) i acetsirćetnog estra (1) kao reaktanata, u prisustvu KOH kao katalizatora i etanola kao agensa kojim se kontroliše viskoznost, izvedeno je u planetarnom mlinu radi ispitivanja mogućnosti mehanohemijske sinteze 3-cijano-6-hidroksi-4-metil-2-piridona (3) na sobnoj temperaturi. Mehanohemijski tretman je izveden sa različitim parametrima mlevenja: vremenom mlevenja do 4 h, različitom veličinom i brojem kuglica, različitom brzinom obrtanja, kao i različitim molarnim odnosom reaktanata i katalizatora. Dobijeni proizvod je okarakterisan određivanjem temperature topljenja, UV, IR i NMR analizama. Nađeno je da je dominantni procesni parametar vreme mlevenja, dok su ostali od manjeg uticaja. Najveći prinos izolovanog proizvoda je oko 56%, dok se naknadnim "odležavanjem" prinos povećava preko 60%.
PB  - Engineering Society for Corrosion, Belgrade, Serbia
T2  - Zaštita materijala
T1  - On the synthesis of 3-cyano-6-hydroxy-4-methyl-2-pyridone at room temperature
T1  - O sintezi 3-cijano-6-hidroksi-4-metil-2-piridona na sobnoj temperaturi
EP  - 236
IS  - 3
SP  - 229
VL  - 60
DO  - 10.5937/zasmat1903229Z
ER  - 
@article{
author = "Zdujić, Miodrag and Petrović, Slobodan and Valentić, Nataša and Mijin, Dušan",
year = "2019",
abstract = "Milling of cyanoacetamide and acetoacetic ester as reactants, in the presence of KOH as the catalyst and ethanol as a viscous control agent (VCA) was performed in a planetary ball mill with the goal of investigating the effect of mechanochemical treatment for the synthesis of 3-cyano-6hydroxy-4-methyl-2-pyridone at room temperature. The mechanochemical synthesis was performed under various milling parameters, i.e. milling time up to 4 h, number and size of balls, angular velocity as well as molar ratio of reactants and the amount of catalyst. The obtained product was characterized by m.p., UV, IR and NMR data. It was fond that the dominant process parameter is the milling time while others are of less importance. The highest isolated yield after milling was up to 56%. The combination of milling and aging increase yield over 60%., Mlevenje cijanoacetoamida (2) i acetsirćetnog estra (1) kao reaktanata, u prisustvu KOH kao katalizatora i etanola kao agensa kojim se kontroliše viskoznost, izvedeno je u planetarnom mlinu radi ispitivanja mogućnosti mehanohemijske sinteze 3-cijano-6-hidroksi-4-metil-2-piridona (3) na sobnoj temperaturi. Mehanohemijski tretman je izveden sa različitim parametrima mlevenja: vremenom mlevenja do 4 h, različitom veličinom i brojem kuglica, različitom brzinom obrtanja, kao i različitim molarnim odnosom reaktanata i katalizatora. Dobijeni proizvod je okarakterisan određivanjem temperature topljenja, UV, IR i NMR analizama. Nađeno je da je dominantni procesni parametar vreme mlevenja, dok su ostali od manjeg uticaja. Najveći prinos izolovanog proizvoda je oko 56%, dok se naknadnim "odležavanjem" prinos povećava preko 60%.",
publisher = "Engineering Society for Corrosion, Belgrade, Serbia",
journal = "Zaštita materijala",
title = "On the synthesis of 3-cyano-6-hydroxy-4-methyl-2-pyridone at room temperature, O sintezi 3-cijano-6-hidroksi-4-metil-2-piridona na sobnoj temperaturi",
pages = "236-229",
number = "3",
volume = "60",
doi = "10.5937/zasmat1903229Z"
}
Zdujić, M., Petrović, S., Valentić, N.,& Mijin, D.. (2019). On the synthesis of 3-cyano-6-hydroxy-4-methyl-2-pyridone at room temperature. in Zaštita materijala
Engineering Society for Corrosion, Belgrade, Serbia., 60(3), 229-236.
https://doi.org/10.5937/zasmat1903229Z
Zdujić M, Petrović S, Valentić N, Mijin D. On the synthesis of 3-cyano-6-hydroxy-4-methyl-2-pyridone at room temperature. in Zaštita materijala. 2019;60(3):229-236.
doi:10.5937/zasmat1903229Z .
Zdujić, Miodrag, Petrović, Slobodan, Valentić, Nataša, Mijin, Dušan, "On the synthesis of 3-cyano-6-hydroxy-4-methyl-2-pyridone at room temperature" in Zaštita materijala, 60, no. 3 (2019):229-236,
https://doi.org/10.5937/zasmat1903229Z . .

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