Skip to main content
SpringerLink
Log in

Synthesis of N-(3- and 4-substituted phenyl)-O-isobutyl thionocarbamates from O-isobutyl xanthate and amines using a nano-platinum multi-walled carbon nanotube catalyst

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Twelve N-(3- and 4-substituted phenyl)-O-isobutyl thionocarbamates, eight of which are novel, were synthesized from O-isobutyl xanthate and 3- and 4-substituted anilines in the presence of a nano-platinum aminophenyl modified multi-walled carbon nanotube catalyst. The nano-Pt catalyst was prepared on a carbon nanotube support modified by diazotization, nitro group reduction, and subsequent microwave-assisted nano-Pt precipitation. The catalyst was characterized by Fourier transform infrared (FT-IR) spectroscopy, elemental analysis, thermogravimetric analysis, and transmission electron microscopy. The nano-platinum/modified carbon nanotube catalyst was compared with a commercial Pt/active carbon catalyst in terms of product purity and yield. The results obtained by the use of the catalysts were additionally compared with those obtained by reaction of sodium isobutyl xanthogenacetate and 3- and 4-substituted anilines. Full structure characterization of the synthesized N-(substituted phenyl)-O-isobutyl thionocarbamates was achieved using FT-IR, 1H and 13C NMR, and mass spectrometric methods, and their purity was proved by elemental analysis and gas chromatography. The new catalytic method offers advantages over the commercial method, such as higher yields and no product purification is required, thus conforming to the principles of ecologically friendly syntheses.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Walter W, Bode KD (1967) Angew Chem 79:281

    Google Scholar 

  2. Glazsrin AB, Denisov AN, Talzi VP, Savin BP (1988) Tiokarbamats, Prommiilennostm po proizvodstvu mineralmnih udobreniy, seriz, Himicheskie sredstva zaoitmi rasteniy. Nauchno-isledovalteski institut Tehniko-ekonomicheskii isledovanii, Moscow

  3. Agrawal PT, Ali YA, Deshmukh SP (2009) Int J Chem Sci 7:775

    CAS  Google Scholar 

  4. Zhou Y, Wang L, Han L, Meng F, Yang C (2009) Carbohydr Res 344:1289

    Article  CAS  Google Scholar 

  5. Zhu B, Marinelli BA, Abbanat D, Foleno BD, Bush K, Macielag MJ (2007) Bioorg Med Chem Lett 17:3900

    Article  CAS  Google Scholar 

  6. Milosavljević MM, Ražić S (2005) Vaprosy himii i himicheskoi tehnologii 3:50

    Google Scholar 

  7. Brink A (2007) Herbicidal gent containing diflufenican. Patent WO2008064787, 5 Jun 2008

  8. Gerstner A (2010) Direktanwendungs-Unkrautvernichtungszusammensetzung. German patent 102008032537, 14 Jan 2010

  9. Rinehart JK (1977) S-Naphthyl N-alkylthiolcarbamates. US patent 4,059,609, 22 Nov 1977

  10. Rinehart JK (1977) Method of controlling pea aphids. US patent 4,055,656, 25 Oct 1977

  11. Kuchikata M, Ikari H, Kuyama H (1979) Metallic salts of polydithiocarbamic acid as microbiocides and algicides. Japanese patent 54028817, 3 Mar 1979

  12. Kunihiko F, Kuniaki S, Haruki O (1978) Germicidal and acaricidal compositions. US patent 4,101,670, 18 Jul 1978

  13. Kisida H, Hatakoshi M (1984) Thiocarbamate compounds, and their use. US patent 4,486,449, 4 Dec 1984

  14. Milisavljević SS, Marinković AD, Milosavljević MM (2010) Hem Ind 64:401

    Article  Google Scholar 

  15. Milosavljević M, Sovrlić M, Marinković AD, Milenković DD (2010) Monatsh Chem 141:749

    Article  Google Scholar 

  16. Bolth FA, Crozier RD, Strow LE (1975) Dialkyl thionocarbamate method. US patent 3,907,854, 23 Sep 1975

  17. Albors-Velaco M, Thorne J, Wain RL (1995) J Agric Food Chem 43:2260

    Article  Google Scholar 

  18. Bishop MD, Gray LA (1991) Catalytic synthesis of thionocarbamates from xanthates and amines. US patent 5,041,599, 20 Aug 1991

  19. Oh HK, Ha JS, Sung DD, Lee I (2004) J Org Chem 69:8219

    Article  CAS  Google Scholar 

  20. Bauman RA (1966) J Chem Eng Data 11:274

    Article  CAS  Google Scholar 

  21. Movassagh B, Zakinezhad Y (2005) Chem Lett 34:1330

    Article  CAS  Google Scholar 

  22. Movassagh B, Soleiman-Beigi M (2008) Monatsh Chem 139:137

    Article  CAS  Google Scholar 

  23. Milosavljević MM, Marinković AD, Đorđević SA (2006) Hem Ind 60:27

    Article  Google Scholar 

  24. Caryl KA, van Rensburg J, Robinson RS (2009) S Afr J Chem 62:143

    Google Scholar 

  25. Movassagh MB, Soleiman-Beigi M (2008) Monatsh Chem 139:927

    Article  CAS  Google Scholar 

  26. Vuković G, Marinković A, Obradović M, Radmilović V, Čolić M, Aleksić R, Uskoković PS (2009) Appl Surf Sci 255:8067

    Article  Google Scholar 

  27. Salipira KL, Mamba BB, Krause RW, Malefetse TJ, Durbach SH (2008) Water SA 34:113

    CAS  Google Scholar 

  28. Vuković GD, Tomić S, Marinković A, Radmilović V, Uskoković PS, Čolić M (2010) Carbon 48:3066

    Article  Google Scholar 

  29. Kakade BA, Pillai VK (2008) Appl Surf Sci 254:4936

    Article  CAS  Google Scholar 

  30. Gorgulho HF, Mesquita JP, Gonçalves F, Pereira MFR, Figueiredo JL (2008) Carbon 46:1544

    Article  CAS  Google Scholar 

  31. Datsyuk V, Kalyva M, Papagelis K, Parthenios J, Tasis D, Siokou A, Kallitsis I, Galiotis C (2008) Carbon 46:833

    Article  CAS  Google Scholar 

  32. Vuković GD, Marinković AD, Čolić M, Ristić MĐ, Aleksić R, Perić-Grujić AA, Uskoković PS (2010) Chem Eng J 157:238

    Article  Google Scholar 

  33. Armarego WLF, Chai CLL (2003) Purification of laboratory chemicals. Elsevier, Amsterdam

    Google Scholar 

  34. Dyke CA, Tour JM (2003) J Am Chem Soc 125:1156

    Article  CAS  Google Scholar 

  35. Hudson JL, Casavant MJ, Tour JM (2004) J Am Chem Soc 126:11158

    Article  CAS  Google Scholar 

  36. Ramanathan T, Fisher FT, Ruoff RS, Brinson LC (2005) Chem Mater 17:1290

    Article  CAS  Google Scholar 

  37. Chen WX, Lee JY, Liu Z (2002) Chem Commun 2588

  38. Li X, Chen WX, Zhao J, Xing W, Xu ZD (2005) Carbon 43:2168

    Article  CAS  Google Scholar 

  39. Trimm DL (2001) Appl Catal A 212:153

    Article  CAS  Google Scholar 

  40. Csuros Z (1944) Magy Chem Foly 50:66

    CAS  Google Scholar 

  41. Bauman RA (1971) Method of preparing thioncarbamate esters. US patent 3,592,835, 13 Jul 1971

  42. Myska J, Stanek J, Bomar M (1968) Collect Czech Chem Comm 33:4416

    CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Ministry of Education and Science of the Republic of Serbia (Project Number 172013 and III45019). Goran Vuković is grateful to the project FP7 REGPOT NANOTECH FTM, GRANT AGREEMENT 245916 for financial support. The authors gratefully thank Professor Velimir Radmilović from the National Centre for Electron Microscopy, Lawrence Berkeley National Laboratory, for the electron microscopy characterization. Electron microscopy characterization was supported by the US Department of Energy, Office of Basic Energy Sciences, Division of Materials Sciences and Engineering under Contract No. DE-AC02 05CH11231.

Author information

Authors and Affiliations

  1. Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11120, Belgrade, Serbia

    Aleksandar D. Marinković, Radoslav Aleksić & Petar S. Uskoković

  2. Economics Institute, Kralja Milana 16, 11000, Belgrade, Serbia

    Milutin M. Milosavljević

  3. Faculty of Technology and Metallurgy, Nanotechnology and Functional Materials Centre, University of Belgrade, Karnegijeva 4, P. O. Box 3503, 11120, Belgrade, Serbia

    Goran D. Vuković

Authors
  1. Milutin M. Milosavljević
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Goran D. Vuković
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Aleksandar D. Marinković
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Radoslav Aleksić
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Petar S. Uskoković
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aleksandar D. Marinković.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Milosavljević, M.M., Vuković, G.D., Marinković, A.D. et al. Synthesis of N-(3- and 4-substituted phenyl)-O-isobutyl thionocarbamates from O-isobutyl xanthate and amines using a nano-platinum multi-walled carbon nanotube catalyst. Monatsh Chem 142, 1045–1053 (2011). https://doi.org/10.1007/s00706-011-0568-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0568-5

Keywords

Search

Navigation