TY  - JOUR
AU  - Milentijević, Goran
AU  - Milošević, Milena
AU  - Milojević, Svetomir
AU  - Marković, Smiljana
AU  - Rančić, Milica
AU  - Marinković, Aleksandar
AU  - Milosavljević, Milutin
PY  - 2023
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/1427
AB  - Styrene-butadiene (SBR) and acrylonitrile-butadiene (NBR) rubber blends with tetramethyl thiuram disulfide (TMTD) and tetramethyl thiuram monosulfide (TMTS) accelerators and environmentally friendly plasticizers, obtained from PET recycling and biobased resources (LA/PG/PET/EG/LA), were prepared. The mechanical properties of the obtained rubber products were tested and compared with those of commercial dioctyl terephthalate (DOTP). TMTS was prepared by simple and efficient one-pot synthesis from dimethylamine, carbon disulfide, potassium cyanide, and ammonium chloride as catalysts in recycled isopropanol/water azeotrope as solvent. In a comparative study, methoxide, ethoxide, iodide, and amide ions were also used. The two-step reaction mechanism of TMTS synthesis involves the oxidation of the amine salt of dimethyldithiocarbamic acid to TMTD by hydrogen peroxide and sulfur elimination from the TMTD disulfide bond. Potassium cyanide appears to be the most efficient nucleophile. The simplicity of operation, mild reaction conditions, solvent recycling, high yields, and applicability to the industrial level are the advantages of this process. Shore hardness, tensile strength, and compression test results of vulcanized blends before and after aging showed similar properties for both accelerators, while somewhat better results were obtained with LA/PG/PET/EG/LA plasticizer.
T2  - Processes
T1  - One-Pot Syntheses of PET-Based Plasticizer and Tetramethyl Thiuram Monosulfide (TMTS) as Vulcanization Accelerator for Rubber Production
IS  - 4
VL  - 11
DO  - 10.3390/pr11041033
UR  - conv_1699
ER  - 

@article{
author = "Milentijević, Goran and Milošević, Milena and Milojević, Svetomir and Marković, Smiljana and Rančić, Milica and Marinković, Aleksandar and Milosavljević, Milutin",
year = "2023",
abstract = "Styrene-butadiene (SBR) and acrylonitrile-butadiene (NBR) rubber blends with tetramethyl thiuram disulfide (TMTD) and tetramethyl thiuram monosulfide (TMTS) accelerators and environmentally friendly plasticizers, obtained from PET recycling and biobased resources (LA/PG/PET/EG/LA), were prepared. The mechanical properties of the obtained rubber products were tested and compared with those of commercial dioctyl terephthalate (DOTP). TMTS was prepared by simple and efficient one-pot synthesis from dimethylamine, carbon disulfide, potassium cyanide, and ammonium chloride as catalysts in recycled isopropanol/water azeotrope as solvent. In a comparative study, methoxide, ethoxide, iodide, and amide ions were also used. The two-step reaction mechanism of TMTS synthesis involves the oxidation of the amine salt of dimethyldithiocarbamic acid to TMTD by hydrogen peroxide and sulfur elimination from the TMTD disulfide bond. Potassium cyanide appears to be the most efficient nucleophile. The simplicity of operation, mild reaction conditions, solvent recycling, high yields, and applicability to the industrial level are the advantages of this process. Shore hardness, tensile strength, and compression test results of vulcanized blends before and after aging showed similar properties for both accelerators, while somewhat better results were obtained with LA/PG/PET/EG/LA plasticizer.",
journal = "Processes",
title = "One-Pot Syntheses of PET-Based Plasticizer and Tetramethyl Thiuram Monosulfide (TMTS) as Vulcanization Accelerator for Rubber Production",
number = "4",
volume = "11",
doi = "10.3390/pr11041033",
url = "conv_1699"
}

Milentijević, G., Milošević, M., Milojević, S., Marković, S., Rančić, M., Marinković, A.,& Milosavljević, M.. (2023). One-Pot Syntheses of PET-Based Plasticizer and Tetramethyl Thiuram Monosulfide (TMTS) as Vulcanization Accelerator for Rubber Production. in Processes, 11(4).
https://doi.org/10.3390/pr11041033
conv_1699

Milentijević G, Milošević M, Milojević S, Marković S, Rančić M, Marinković A, Milosavljević M. One-Pot Syntheses of PET-Based Plasticizer and Tetramethyl Thiuram Monosulfide (TMTS) as Vulcanization Accelerator for Rubber Production. in Processes. 2023;11(4).
doi:10.3390/pr11041033
conv_1699 .

Milentijević, Goran, Milošević, Milena, Milojević, Svetomir, Marković, Smiljana, Rančić, Milica, Marinković, Aleksandar, Milosavljević, Milutin, "One-Pot Syntheses of PET-Based Plasticizer and Tetramethyl Thiuram Monosulfide (TMTS) as Vulcanization Accelerator for Rubber Production" in Processes, 11, no. 4 (2023),
https://doi.org/10.3390/pr11041033 .,
conv_1699 .

TY  - JOUR
AU  - Milentijević, Goran
AU  - Marinković, Aleksandar D.
AU  - Rančić, Milica
AU  - Bogdanović, Aleksandra
AU  - Prlainović, Nevena
AU  - Marković, Smiljana
AU  - Milosavljević, Milutin
PY  - 2021
UR  - https://omorika.sfb.bg.ac.rs/handle/123456789/1193
AB  - The specific objectives of the presented study were related to the optimization of the production process of N-alkyl-, N,N-dialkyl-, and N-cycloalkyl-O-isobutyl thiocarbamate; trial industrial production of N-ethyl-O-isobutyl thiocarbamate; and the evaluation of flotation efficiency of N-ethyl-O-isobutyl thiocarbamate using a real ore sample. The optimization of thiocarbamate syntheses were performed by varying the molar ratio of isobutyl alcohol, carbon disulfide, potassium hydroxide, reaction time, and reaction temperature. In the first step, one-pot reaction took place to produce alkyl xanthate and was followed with chlorination to give alkyl chloroformate (O-alkyl carbonochloridothioate); finally, thiocarbamates were obtained by the reaction with corresponding amines. N-alkyl-O-ethyl thiocarbamate was synthesized as a comparative flotation agent. The structure of the synthesized compounds was confirmed by IR, H-1 and C-13 NMR, and MS instrumental methods, and the purity was determined by gas chromatographic method and elemental analysis. The optimized methods gave high-purity products in a significant yield that was also confirmed by semi-industrial production of N-ethyl-O-isobutyl thiocarbamate. The optimized thiocarbamate synthesis, without isolation of intermediates, is of great importance from the aspect of green technologies. Flotation efficiency test results, using real copper and zinc ores, showed the highest activity of N-ethyl-O-isobutyl thiocarbamate. The optimal one-pot thiocarbamate synthesis provides a simple procedure with a high conversion degree, and, thus, offers valuable technology applicable at the industrial scale.
T2  - Minerals
T1  - New Facile One-Pot Synthesis of Isobutyl Thiocarbamate in Recycling Solvent Mixture
IS  - 12
VL  - 11
DO  - 10.3390/min11121346
UR  - conv_1605
ER  - 

@article{
author = "Milentijević, Goran and Marinković, Aleksandar D. and Rančić, Milica and Bogdanović, Aleksandra and Prlainović, Nevena and Marković, Smiljana and Milosavljević, Milutin",
year = "2021",
abstract = "The specific objectives of the presented study were related to the optimization of the production process of N-alkyl-, N,N-dialkyl-, and N-cycloalkyl-O-isobutyl thiocarbamate; trial industrial production of N-ethyl-O-isobutyl thiocarbamate; and the evaluation of flotation efficiency of N-ethyl-O-isobutyl thiocarbamate using a real ore sample. The optimization of thiocarbamate syntheses were performed by varying the molar ratio of isobutyl alcohol, carbon disulfide, potassium hydroxide, reaction time, and reaction temperature. In the first step, one-pot reaction took place to produce alkyl xanthate and was followed with chlorination to give alkyl chloroformate (O-alkyl carbonochloridothioate); finally, thiocarbamates were obtained by the reaction with corresponding amines. N-alkyl-O-ethyl thiocarbamate was synthesized as a comparative flotation agent. The structure of the synthesized compounds was confirmed by IR, H-1 and C-13 NMR, and MS instrumental methods, and the purity was determined by gas chromatographic method and elemental analysis. The optimized methods gave high-purity products in a significant yield that was also confirmed by semi-industrial production of N-ethyl-O-isobutyl thiocarbamate. The optimized thiocarbamate synthesis, without isolation of intermediates, is of great importance from the aspect of green technologies. Flotation efficiency test results, using real copper and zinc ores, showed the highest activity of N-ethyl-O-isobutyl thiocarbamate. The optimal one-pot thiocarbamate synthesis provides a simple procedure with a high conversion degree, and, thus, offers valuable technology applicable at the industrial scale.",
journal = "Minerals",
title = "New Facile One-Pot Synthesis of Isobutyl Thiocarbamate in Recycling Solvent Mixture",
number = "12",
volume = "11",
doi = "10.3390/min11121346",
url = "conv_1605"
}

Milentijević, G., Marinković, A. D., Rančić, M., Bogdanović, A., Prlainović, N., Marković, S.,& Milosavljević, M.. (2021). New Facile One-Pot Synthesis of Isobutyl Thiocarbamate in Recycling Solvent Mixture. in Minerals, 11(12).
https://doi.org/10.3390/min11121346
conv_1605

Milentijević G, Marinković AD, Rančić M, Bogdanović A, Prlainović N, Marković S, Milosavljević M. New Facile One-Pot Synthesis of Isobutyl Thiocarbamate in Recycling Solvent Mixture. in Minerals. 2021;11(12).
doi:10.3390/min11121346
conv_1605 .

Milentijević, Goran, Marinković, Aleksandar D., Rančić, Milica, Bogdanović, Aleksandra, Prlainović, Nevena, Marković, Smiljana, Milosavljević, Milutin, "New Facile One-Pot Synthesis of Isobutyl Thiocarbamate in Recycling Solvent Mixture" in Minerals, 11, no. 12 (2021),
https://doi.org/10.3390/min11121346 .,
conv_1605 .