Electrosynthesis of N-tert-Butyl-2-benzothiazolesulfenamide

G. R. Mukminova G. R. Mukminova , M. D. Simonov M. D. Simonov , G. V. Chernykh G. V. Chernykh , V. T. Novikov V. T. Novikov , I. A. Avrutskaya I. A. Avrutskaya
Российский электрохимический журнал
Abstract / Full Text

Conditions for the production of N-tert-butyl-2-benzothiazolesulfenamide (TBBS) in an oxidative condensation of 2-mercaptobenzothiazole and tert-butylamine are determined. The electrosynthesis occurs during electrolysis of a 4.5–5.0 M NaCl solution containing a water-immiscible organic solvent extracting TBBS. The process efficiency is the highest at the following conditions: a 1 : 8 ratio between 2-mercaptobenzothiazole and tert-butylamine, a DSA, a stainless-steel cathode, a current density of 300 A m–2, and a continuous extraction of TBBS into a 3 : 1 mixture of carbon tetrachloride and acetonitrile. Under these conditions, the TBBS yield is 98–100%, the current efficiency is 74%, the process productivity is 0.9 kg m–2 h–1, and the electricity consumption is 1.9 kW h kg–1. Repeated use of the aqueous phase corrected for the source products jeopardizes neither the process characteristics nor the product quality.

Author information
  • Mendeleev University of Chemical Technology, Miusskaya pl. 9, Moscow, 125190, Russia

    G. R. Mukminova, M. D. Simonov, G. V. Chernykh, V. T. Novikov & I. A. Avrutskaya

  1. Mukminova, G.R., Avrutskaya, I.A., and Novikov, V.T., Elektrokhimiya, 1999, vol. 35, p. 948.
  2. GDR Patent 247 351, MKI6 S 07 D 277/80.
  3. Mukminova, G.R., Chernykh, G.V., Novikov, V.T., and Avrutskaya, I.A., Elektrokhimiya, 1998, vol. 34, p. 852.
  4. Yakimenko, L.M. and Seryshev, G.A., Elektrokhimicheskii sintez neorganicheskikh soedinenii (Electrochemical Synthesis of Inorganic Compounds), Moscow: Khimiya, 1984.
  5. Ignatov, V.A., Pirogov, P.A., Zhorkin, N.V., and Akchurina, R.A., Khimiya proizvodnykh sul'fenovykh kislot (The Chemistry of Sulfenic Acid Derivatives), Moscow: NIITEKhim, 1970, p. 42.