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New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid

Novi postupak sinteze N-alkil- i N,N-dialkil-O-etil- i O-izopropiltiokarbamata oksidacijom aminskih soli ksantogene kiseline

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2010
0367-598X1000049M.pdf (363.2Kb)
Authors
Milisavljević, Smiljka S.
Marinković, Aleksandar
Milosavljević, Milutin M.
Article (Published version)
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Abstract
Syntheses of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates by oxidation of ammonium salts of ethyl- and isopropylxanthogenic acid in the presence of sodium hypochlorite and hydrogen peroxide were performed. Ammonium salts of ethyl - and isopropylxanthogenic acid was obtained by the reaction of alkylammonium sulfate and sodium ethyl and isopropyl xanthate. Dependence of N-ethyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters (reaction time, molar ratio of oxidant and ethylamonium salt of isopropylxanthogenic acid) were studied. Optimal reaction conditions for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates were established. The synthesized compounds have been fully characterized by FTIR, 1H-NMR and MS data, while purities have been determined by GC method. A plausible pathway for the N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates synthesis in the presence of the oxidative agents sodium hypochlorit...e and hydrogen peroxide was proposed. The presented synthetic method has been developed at laboratory and applied at semi-industrial level. The developed optimal method provides a powerful and versatile means for the preparation of N-alkyl and N,N-dialkyl- O-ethyl and O-isopropyl thiocarbamates, offering several benefits, namely, simple operation, mild reaction conditions, bypass of hazardous organic solvents, moderately toxic and inexpensive reagents, and also short reaction times and high product yields.

U ovom radu prikazana je sinteza, novim optimizovanim postupkom, N-alkil - i N,N-dialkil- O-etil- i O-izopropiltiokarbamata oksidacijom aminskih soli etil- i izopropilksantogene kiseline pomoću natrijum-hipohlorita i vodonik-peroksida. Alkilaminske soli etil- i izopropilksantogene kiseline dobijene su reakcijom između alkilamonijumsulfata i natrijum-etilksantata ili natrijum-izopropilksantata. Struktura sintetisanih jedinjenja potvrđena je IR, 1H-NMR i MS instrumentalnim metodama, a čistoća je određena gasnom hromatografskom metodom. Postupak sinteze opisan u ovom radu daje velike prednosti u odnosu na poznate postupke sinteze koji se primenjuju u laboratoriji i u industrijskim uslovima. Postupak karakteriše visok stepen konverzije reaktanata u proizvod, visok stepen čistoće, bez sporednih proizvoda, a tehnološki je primenljiv na industrijskom nivou proizvodnje. Sintetisana jedinjenja se primenjuju kao selektivni reagensi za flotaciju ruda bakra i cinka.
Keywords:
N-Alkyl-O-isopropylthiocarbamate / N-Alkyl-O-ethyl thiocarbamate / hydrogen peroxide / sodium hypochlorite / synthesis / N-Alkil-O-izopropiltiokarbamat / N-Alkil-O-etiltiokarbamat / vodonik-peroksid / natrijum-hipohlorit / sinteza
Source:
Hemijska industrija, 2010, 64, 5, 401-409
Publisher:
  • Association of Chemical Engineers of Serbia

DOI: 10.2298/HEMIND100527049M

ISSN: 0367-598X

WoS: 000285175800005

Scopus: 2-s2.0-78449275775
[ Google Scholar ]
6
6
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1657
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Milisavljević, Smiljka S.
AU  - Marinković, Aleksandar
AU  - Milosavljević, Milutin M.
PY  - 2010
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1657
AB  - Syntheses of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates by oxidation of ammonium salts of ethyl- and isopropylxanthogenic acid in the presence of sodium hypochlorite and hydrogen peroxide were performed. Ammonium salts of ethyl - and isopropylxanthogenic acid was obtained by the reaction of alkylammonium sulfate and sodium ethyl and isopropyl xanthate. Dependence of N-ethyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters (reaction time, molar ratio of oxidant and ethylamonium salt of isopropylxanthogenic acid) were studied. Optimal reaction conditions for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates were established. The synthesized compounds have been fully characterized by FTIR, 1H-NMR and MS data, while purities have been determined by GC method. A plausible pathway for the N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates synthesis in the presence of the oxidative agents sodium hypochlorite and hydrogen peroxide was proposed. The presented synthetic method has been developed at laboratory and applied at semi-industrial level. The developed optimal method provides a powerful and versatile means for the preparation of N-alkyl and N,N-dialkyl- O-ethyl and O-isopropyl thiocarbamates, offering several benefits, namely, simple operation, mild reaction conditions, bypass of hazardous organic solvents, moderately toxic and inexpensive reagents, and also short reaction times and high product yields.
AB  - U ovom radu prikazana je sinteza, novim optimizovanim postupkom, N-alkil - i N,N-dialkil- O-etil- i O-izopropiltiokarbamata oksidacijom aminskih soli etil- i izopropilksantogene kiseline pomoću natrijum-hipohlorita i vodonik-peroksida. Alkilaminske soli etil- i izopropilksantogene kiseline dobijene su reakcijom između alkilamonijumsulfata i natrijum-etilksantata ili natrijum-izopropilksantata. Struktura sintetisanih jedinjenja potvrđena je IR, 1H-NMR i MS instrumentalnim metodama, a čistoća je određena gasnom hromatografskom metodom. Postupak sinteze opisan u ovom radu daje velike prednosti u odnosu na poznate postupke sinteze koji se primenjuju u laboratoriji i u industrijskim uslovima. Postupak karakteriše visok stepen konverzije reaktanata u proizvod, visok stepen čistoće, bez sporednih proizvoda, a tehnološki je primenljiv na industrijskom nivou proizvodnje. Sintetisana jedinjenja se primenjuju kao selektivni reagensi za flotaciju ruda bakra i cinka.
PB  - Association of Chemical Engineers of Serbia
T2  - Hemijska industrija
T1  - New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid
T1  - Novi postupak sinteze N-alkil- i N,N-dialkil-O-etil- i O-izopropiltiokarbamata oksidacijom aminskih soli ksantogene kiseline
EP  - 409
IS  - 5
SP  - 401
VL  - 64
DO  - 10.2298/HEMIND100527049M
ER  - 
@article{
author = "Milisavljević, Smiljka S. and Marinković, Aleksandar and Milosavljević, Milutin M.",
year = "2010",
abstract = "Syntheses of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates by oxidation of ammonium salts of ethyl- and isopropylxanthogenic acid in the presence of sodium hypochlorite and hydrogen peroxide were performed. Ammonium salts of ethyl - and isopropylxanthogenic acid was obtained by the reaction of alkylammonium sulfate and sodium ethyl and isopropyl xanthate. Dependence of N-ethyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters (reaction time, molar ratio of oxidant and ethylamonium salt of isopropylxanthogenic acid) were studied. Optimal reaction conditions for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates were established. The synthesized compounds have been fully characterized by FTIR, 1H-NMR and MS data, while purities have been determined by GC method. A plausible pathway for the N-alkyl and N,N-dialkyl-O-ethyl and O-isopropyl thiocarbamates synthesis in the presence of the oxidative agents sodium hypochlorite and hydrogen peroxide was proposed. The presented synthetic method has been developed at laboratory and applied at semi-industrial level. The developed optimal method provides a powerful and versatile means for the preparation of N-alkyl and N,N-dialkyl- O-ethyl and O-isopropyl thiocarbamates, offering several benefits, namely, simple operation, mild reaction conditions, bypass of hazardous organic solvents, moderately toxic and inexpensive reagents, and also short reaction times and high product yields., U ovom radu prikazana je sinteza, novim optimizovanim postupkom, N-alkil - i N,N-dialkil- O-etil- i O-izopropiltiokarbamata oksidacijom aminskih soli etil- i izopropilksantogene kiseline pomoću natrijum-hipohlorita i vodonik-peroksida. Alkilaminske soli etil- i izopropilksantogene kiseline dobijene su reakcijom između alkilamonijumsulfata i natrijum-etilksantata ili natrijum-izopropilksantata. Struktura sintetisanih jedinjenja potvrđena je IR, 1H-NMR i MS instrumentalnim metodama, a čistoća je određena gasnom hromatografskom metodom. Postupak sinteze opisan u ovom radu daje velike prednosti u odnosu na poznate postupke sinteze koji se primenjuju u laboratoriji i u industrijskim uslovima. Postupak karakteriše visok stepen konverzije reaktanata u proizvod, visok stepen čistoće, bez sporednih proizvoda, a tehnološki je primenljiv na industrijskom nivou proizvodnje. Sintetisana jedinjenja se primenjuju kao selektivni reagensi za flotaciju ruda bakra i cinka.",
publisher = "Association of Chemical Engineers of Serbia",
journal = "Hemijska industrija",
title = "New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid, Novi postupak sinteze N-alkil- i N,N-dialkil-O-etil- i O-izopropiltiokarbamata oksidacijom aminskih soli ksantogene kiseline",
pages = "409-401",
number = "5",
volume = "64",
doi = "10.2298/HEMIND100527049M"
}
Milisavljević, S. S., Marinković, A.,& Milosavljević, M. M.. (2010). New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid. in Hemijska industrija
Association of Chemical Engineers of Serbia., 64(5), 401-409.
https://doi.org/10.2298/HEMIND100527049M
Milisavljević SS, Marinković A, Milosavljević MM. New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid. in Hemijska industrija. 2010;64(5):401-409.
doi:10.2298/HEMIND100527049M .
Milisavljević, Smiljka S., Marinković, Aleksandar, Milosavljević, Milutin M., "New method for synthesis of N-alkyl and N,N-dialkyl-O-ethyl and O-isopropylthiocarbamates by oxidation of ammonium salt of xhantogenic acid" in Hemijska industrija, 64, no. 5 (2010):401-409,
https://doi.org/10.2298/HEMIND100527049M . .

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