TY - JOUR
T1 - New bis-di-organotin compounds derived from aminoacid-imine-hexadentate ligands. Multifunctional evaluation as corrosion inhibitors, antibacterials and asphaltene dispersants/inhibitors
AU - Hernández-Altamirano, Raúl
AU - Mena-Cervantes, Violeta Y.
AU - Chávez-Miyauchi, Tomás Eduardo
AU - Nieto-Álvarez, David Aarón
AU - Domínguez-Aguilar, Marco A.
AU - Zamudio-Rivera, Luis S.
AU - Barba, Victor
AU - Fernández-Perrino, Francisco José
AU - Pérez-Miranda, Sandra
AU - Beltrán, Hiram I.
N1 - Funding Information:
This work was supported by Instituto Mexicano del Petróleo.
PY - 2013/3/22
Y1 - 2013/3/22
N2 - A new class of bis-di-organotin (IV) compounds were synthesized in good yields (ca. 80%) by a one-step five molecules reaction in which intervene two molecular equivalents of leucine, one of 5,5′-methylene-bis- salicylaldehyde and either two of di-n-butyltin (IV) or diphenyltin (IV) oxides, that independently provided two bis-di-organotin derivatives. The structures of these two compounds were established by 1H, 13C and 119Sn NMR, as well as by IR and elemental analysis. In both cases the 119Sn chemical shifts are characteristic of pentacoordinated atoms in solution of non-coordinating solvent (CDCl3). Once characterized, the novel compounds were tested as corrosion inhibitors at 25, 50 and 100 mg L-1 on mild steel surfaces in sour brine by linear polarization resistance and potentiodynamic curves. These experiments prove that these derivatives present top efficiencies of 54% and 68% for butyl and phenyl moieties, respectively. In addition, these two compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5) and Pseudomonas fluorescens strains to assess their bactericidal activities, being more effective for the E. coli strain, at concentrations as low as 25 mg L-1. Moreover, in order to correlate different activities and ascertain homologous action mechanisms, the two derivatives were tested for their asphaltene inhibition/dispersion activity. The results suggest that the presence of the four n-butyl moieties provide the needed amphiphillic balance to obtain better efficiencies in the tested activities.
AB - A new class of bis-di-organotin (IV) compounds were synthesized in good yields (ca. 80%) by a one-step five molecules reaction in which intervene two molecular equivalents of leucine, one of 5,5′-methylene-bis- salicylaldehyde and either two of di-n-butyltin (IV) or diphenyltin (IV) oxides, that independently provided two bis-di-organotin derivatives. The structures of these two compounds were established by 1H, 13C and 119Sn NMR, as well as by IR and elemental analysis. In both cases the 119Sn chemical shifts are characteristic of pentacoordinated atoms in solution of non-coordinating solvent (CDCl3). Once characterized, the novel compounds were tested as corrosion inhibitors at 25, 50 and 100 mg L-1 on mild steel surfaces in sour brine by linear polarization resistance and potentiodynamic curves. These experiments prove that these derivatives present top efficiencies of 54% and 68% for butyl and phenyl moieties, respectively. In addition, these two compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5) and Pseudomonas fluorescens strains to assess their bactericidal activities, being more effective for the E. coli strain, at concentrations as low as 25 mg L-1. Moreover, in order to correlate different activities and ascertain homologous action mechanisms, the two derivatives were tested for their asphaltene inhibition/dispersion activity. The results suggest that the presence of the four n-butyl moieties provide the needed amphiphillic balance to obtain better efficiencies in the tested activities.
KW - Aminoacid
KW - Antibacterial agents
KW - Asphaltenes stabilization
KW - Corrosion inhibitors
KW - Organotin
UR - http://www.scopus.com/inward/record.url?scp=84875480596&partnerID=8YFLogxK
U2 - 10.1016/j.poly.2012.09.022
DO - 10.1016/j.poly.2012.09.022
M3 - Artículo
SN - 0277-5387
VL - 52
SP - 301
EP - 307
JO - Polyhedron
JF - Polyhedron
ER -