TY  - JOUR
AU  - Sovrlić, Milica
AU  - Milosavljević, Milutin M.
AU  - Marinković, Aleksandar
AU  - Đukanović, Jasmina S.
AU  - Brković, Danijela V.
AU  - Konstantinović, Sandra
PY  - 2011
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1795
AB  - An optimized synthesis of N-alkyl, N,N-dialkyl- and N-cycloalkyl-O-isobutyl thioncarbamates by aminolysis of sodium isobutylxanthogenic acid (NaiBXAc) and primary, secondary and cycloalkyl amines was developed at laboratory scale and applied at semi-industrial level. Studies on dependence of N-n-propyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters: reaction time and molar ratio of n-propylamine and NaiBXAc, were performed. In such way, optimal reaction conditions for synthesis of N-alkyl, N,N-dialkyl- and N-cycloalkyl- O-isobutyl thioncarbamates, by aminolysis of NaiBXAc, were established. Also, comparative results of thioncarbamates synthesis starting from potassium isobutyl xanthate (KiBX) and corresponding amines in presence of different oxidants (hydrogen peroxide, sodium hypochlorite and new oxidative agent potassium peroxodisulfate) were evaluated. The synthesized compounds have been fully characterized by FTIR, 1H- and 13C-NMR and MS data, elemental analysis and purity have been determined by gas chromatographic method (GC). To our knowledge, ten synthesized thioncarbamates are here characterized for the first time. The synthesized compounds could be used as selective reagents for flotation of copper and zinc ores. The presented methods offer several benefits, namely, high product yields and purity, simple operation, mild reaction conditions without use of hazardous organic solvents, while some of them could be implemented on industrial scale production.
AB  - U radu je prikazana optimizovana sinteza N-alkil-, N,N-dialkil- i N-cikloalkil-O-izobutiltionkarbamata reakcijom aminolize natrijum-izobutilksantogenacetata (NaiBXAc) i primarnih, sekundarnih i cikloalkilamina. Takođe, dat je pregled uporednih postupaka sinteze tionkarbamata polazeći od kalijum-izobutilksantata (KiBX) i odgovarajućih amina u prisustvu različitih oksidacionih sredstava: vodonik-peroksida, natrijum-hipohlorita i kalijum-peroksodisulfata kao novog oksidacionog sredstva. Struktura sintetisanih jedinjenja potvrđena je FTIR, 1H- i 13C-NMR i MS instrumentalnim metodama i elementarnom analizom, a čistoća je određena gasnom hromatografskom metodom. Deset sintetisanih tionkarbamata su prvi put okarakterisani i predstavljaju nova jedinjenja. Sintetisana jedinjenja mogu naći primenu kao selektivni reagensi za flotaciju rude bakra i cinka. Opisane postupke karakteriše visok stepen konverzije i čistoća proizvoda, blagi reakcioni uslovi bez upotrebe organskih rastvarača kao reakcionog medijuma, a neki su tehnološki primenljivi na industrijskom nivou proizvodnje.
PB  - Association of Chemical Engineers of Serbia
T2  - Hemijska industrija
T1  - Comparative analysis of oxidative synthesis of N-alkyl, N,N-dialkyl and N-cykloalkyl-O-isobutyl thioncarbamate
T1  - Uporedna analiza oksidativnih postupaka sinteze N-alkil, N,N-dialkil i N-cikloalkil-O-izobutil tionkarbamata
EP  - 549
IS  - 5
SP  - 541
VL  - 65
DO  - 10.2298/HEMIND110504038S
ER  - 

@article{
author = "Sovrlić, Milica and Milosavljević, Milutin M. and Marinković, Aleksandar and Đukanović, Jasmina S. and Brković, Danijela V. and Konstantinović, Sandra",
year = "2011",
abstract = "An optimized synthesis of N-alkyl, N,N-dialkyl- and N-cycloalkyl-O-isobutyl thioncarbamates by aminolysis of sodium isobutylxanthogenic acid (NaiBXAc) and primary, secondary and cycloalkyl amines was developed at laboratory scale and applied at semi-industrial level. Studies on dependence of N-n-propyl-O-isopropylthiocarbamate yield and purity with respect to reaction parameters: reaction time and molar ratio of n-propylamine and NaiBXAc, were performed. In such way, optimal reaction conditions for synthesis of N-alkyl, N,N-dialkyl- and N-cycloalkyl- O-isobutyl thioncarbamates, by aminolysis of NaiBXAc, were established. Also, comparative results of thioncarbamates synthesis starting from potassium isobutyl xanthate (KiBX) and corresponding amines in presence of different oxidants (hydrogen peroxide, sodium hypochlorite and new oxidative agent potassium peroxodisulfate) were evaluated. The synthesized compounds have been fully characterized by FTIR, 1H- and 13C-NMR and MS data, elemental analysis and purity have been determined by gas chromatographic method (GC). To our knowledge, ten synthesized thioncarbamates are here characterized for the first time. The synthesized compounds could be used as selective reagents for flotation of copper and zinc ores. The presented methods offer several benefits, namely, high product yields and purity, simple operation, mild reaction conditions without use of hazardous organic solvents, while some of them could be implemented on industrial scale production., U radu je prikazana optimizovana sinteza N-alkil-, N,N-dialkil- i N-cikloalkil-O-izobutiltionkarbamata reakcijom aminolize natrijum-izobutilksantogenacetata (NaiBXAc) i primarnih, sekundarnih i cikloalkilamina. Takođe, dat je pregled uporednih postupaka sinteze tionkarbamata polazeći od kalijum-izobutilksantata (KiBX) i odgovarajućih amina u prisustvu različitih oksidacionih sredstava: vodonik-peroksida, natrijum-hipohlorita i kalijum-peroksodisulfata kao novog oksidacionog sredstva. Struktura sintetisanih jedinjenja potvrđena je FTIR, 1H- i 13C-NMR i MS instrumentalnim metodama i elementarnom analizom, a čistoća je određena gasnom hromatografskom metodom. Deset sintetisanih tionkarbamata su prvi put okarakterisani i predstavljaju nova jedinjenja. Sintetisana jedinjenja mogu naći primenu kao selektivni reagensi za flotaciju rude bakra i cinka. Opisane postupke karakteriše visok stepen konverzije i čistoća proizvoda, blagi reakcioni uslovi bez upotrebe organskih rastvarača kao reakcionog medijuma, a neki su tehnološki primenljivi na industrijskom nivou proizvodnje.",
publisher = "Association of Chemical Engineers of Serbia",
journal = "Hemijska industrija",
title = "Comparative analysis of oxidative synthesis of N-alkyl, N,N-dialkyl and N-cykloalkyl-O-isobutyl thioncarbamate, Uporedna analiza oksidativnih postupaka sinteze N-alkil, N,N-dialkil i N-cikloalkil-O-izobutil tionkarbamata",
pages = "549-541",
number = "5",
volume = "65",
doi = "10.2298/HEMIND110504038S"
}

Sovrlić, M., Milosavljević, M. M., Marinković, A., Đukanović, J. S., Brković, D. V.,& Konstantinović, S.. (2011). Comparative analysis of oxidative synthesis of N-alkyl, N,N-dialkyl and N-cykloalkyl-O-isobutyl thioncarbamate. in Hemijska industrija
Association of Chemical Engineers of Serbia., 65(5), 541-549.
https://doi.org/10.2298/HEMIND110504038S

Sovrlić M, Milosavljević MM, Marinković A, Đukanović JS, Brković DV, Konstantinović S. Comparative analysis of oxidative synthesis of N-alkyl, N,N-dialkyl and N-cykloalkyl-O-isobutyl thioncarbamate. in Hemijska industrija. 2011;65(5):541-549.
doi:10.2298/HEMIND110504038S .

Sovrlić, Milica, Milosavljević, Milutin M., Marinković, Aleksandar, Đukanović, Jasmina S., Brković, Danijela V., Konstantinović, Sandra, "Comparative analysis of oxidative synthesis of N-alkyl, N,N-dialkyl and N-cykloalkyl-O-isobutyl thioncarbamate" in Hemijska industrija, 65, no. 5 (2011):541-549,
https://doi.org/10.2298/HEMIND110504038S . .

TY  - JOUR
AU  - Milosavljević, Milutin M.
AU  - Sovrlić, Milica
AU  - Marinković, Aleksandar
AU  - Milenković, Dragan D.
PY  - 2010
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1660
AB  - A novel synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate and primary and secondary amines, using three oxidizing systems, has been developed on the laboratory scale, and the method using sodium hypochlorite has been applied on a semi-industrial scale. The effect of the oxidizing agents, sodium hypochlorite, in-situ-generated peracetic acid, and the manganese(II) acetate/oxygen system on product purity and yield was studied. The results obtained by use of these three methods were compared with those obtained by reaction of sodium ethyl xanthogenacetate and amines, and of sodium ethyl xanthate with amines in the presence of sulfated nickel zeolite catalyst. The reaction mechanism of sodium hypochlorite oxidation has been established on the basis of isolation of reaction intermediates and determination of their structure by use of Fourier-transform infrared, (1)H and (13)C NMR, and mass spectrometric methods. The suggested sodium hypochlorite and manganese(II) acetate/oxygen systems have many advantages in comparison with commercial and catalytically promoted synthetic methods, because they are new ecologically friendly syntheses.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants
EP  - 755
IS  - 7
SP  - 749
VL  - 141
DO  - 10.1007/s00706-010-0328-y
ER  - 

@article{
author = "Milosavljević, Milutin M. and Sovrlić, Milica and Marinković, Aleksandar and Milenković, Dragan D.",
year = "2010",
abstract = "A novel synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate and primary and secondary amines, using three oxidizing systems, has been developed on the laboratory scale, and the method using sodium hypochlorite has been applied on a semi-industrial scale. The effect of the oxidizing agents, sodium hypochlorite, in-situ-generated peracetic acid, and the manganese(II) acetate/oxygen system on product purity and yield was studied. The results obtained by use of these three methods were compared with those obtained by reaction of sodium ethyl xanthogenacetate and amines, and of sodium ethyl xanthate with amines in the presence of sulfated nickel zeolite catalyst. The reaction mechanism of sodium hypochlorite oxidation has been established on the basis of isolation of reaction intermediates and determination of their structure by use of Fourier-transform infrared, (1)H and (13)C NMR, and mass spectrometric methods. The suggested sodium hypochlorite and manganese(II) acetate/oxygen systems have many advantages in comparison with commercial and catalytically promoted synthetic methods, because they are new ecologically friendly syntheses.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants",
pages = "755-749",
number = "7",
volume = "141",
doi = "10.1007/s00706-010-0328-y"
}

Milosavljević, M. M., Sovrlić, M., Marinković, A.,& Milenković, D. D.. (2010). A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants. in Monatshefte Fur Chemie
Springer Wien, Wien., 141(7), 749-755.
https://doi.org/10.1007/s00706-010-0328-y

Milosavljević MM, Sovrlić M, Marinković A, Milenković DD. A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants. in Monatshefte Fur Chemie. 2010;141(7):749-755.
doi:10.1007/s00706-010-0328-y .

Milosavljević, Milutin M., Sovrlić, Milica, Marinković, Aleksandar, Milenković, Dragan D., "A synthesis of N-alkyl and N,N-dialkyl O-ethyl thiocarbamates from diethyl dixanthogenate using different oxidants" in Monatshefte Fur Chemie, 141, no. 7 (2010):749-755,
https://doi.org/10.1007/s00706-010-0328-y . .

TY  - JOUR
AU  - Milosavljević, Milutin M.
AU  - Marinković, Aleksandar
AU  - Petrović, Slobodan
AU  - Sovrlić, Milica
PY  - 2009
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1448
AB  - A new ecologically friendly synthesis of N-alkyl-O-ethylthioncarbamates from ethyl dixanthogenates, waste material from the xanthate production plant, and monoalkylamines has been performed in this work. Structure determination of the synthesized compounds and also corresponding intermediates has been performed by IR, 1H-NMR and MS spectrometric methods. Residual dixanthogenates and thioncarbamates in waste water have been done by the gas chromatographic method and corresponding standard curve. It was confirmed that the reaction product was not present in water, while the concentration of dixanthogenates has been determined to be under the maximum contamination limit.
PB  - Association of the Chemical Engineers of Serbia
T2  - Chemical Industry & Chemical Engineering Quarterly
T1  - A new ecologically friendly process for the synthesis of selective flotation reagents
EP  - 262
IS  - 4
SP  - 257
VL  - 15
DO  - 10.2298/CICEQ0904257M
ER  - 

@article{
author = "Milosavljević, Milutin M. and Marinković, Aleksandar and Petrović, Slobodan and Sovrlić, Milica",
year = "2009",
abstract = "A new ecologically friendly synthesis of N-alkyl-O-ethylthioncarbamates from ethyl dixanthogenates, waste material from the xanthate production plant, and monoalkylamines has been performed in this work. Structure determination of the synthesized compounds and also corresponding intermediates has been performed by IR, 1H-NMR and MS spectrometric methods. Residual dixanthogenates and thioncarbamates in waste water have been done by the gas chromatographic method and corresponding standard curve. It was confirmed that the reaction product was not present in water, while the concentration of dixanthogenates has been determined to be under the maximum contamination limit.",
publisher = "Association of the Chemical Engineers of Serbia",
journal = "Chemical Industry & Chemical Engineering Quarterly",
title = "A new ecologically friendly process for the synthesis of selective flotation reagents",
pages = "262-257",
number = "4",
volume = "15",
doi = "10.2298/CICEQ0904257M"
}

Milosavljević, M. M., Marinković, A., Petrović, S.,& Sovrlić, M.. (2009). A new ecologically friendly process for the synthesis of selective flotation reagents. in Chemical Industry & Chemical Engineering Quarterly
Association of the Chemical Engineers of Serbia., 15(4), 257-262.
https://doi.org/10.2298/CICEQ0904257M

Milosavljević MM, Marinković A, Petrović S, Sovrlić M. A new ecologically friendly process for the synthesis of selective flotation reagents. in Chemical Industry & Chemical Engineering Quarterly. 2009;15(4):257-262.
doi:10.2298/CICEQ0904257M .

Milosavljević, Milutin M., Marinković, Aleksandar, Petrović, Slobodan, Sovrlić, Milica, "A new ecologically friendly process for the synthesis of selective flotation reagents" in Chemical Industry & Chemical Engineering Quarterly, 15, no. 4 (2009):257-262,
https://doi.org/10.2298/CICEQ0904257M . .