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. 2019 Nov 20;9(1):17219.
doi: 10.1038/s41598-019-53531-5.

Magnetic nanoantioxidants with improved radical-trapping stoichiometry as stabilizers for inhibition of peroxide formation in ethereal solvents

Caterina Viglianisi  1 , Alessia Scarlini  2 , Lorenzo Tofani  2 , Stefano Menichetti  2 , Andrea Baschieri  3 , Riccardo Amorati  3
Affiliations

Magnetic nanoantioxidants with improved radical-trapping stoichiometry as stabilizers for inhibition of peroxide formation in ethereal solvents

Caterina Viglianisi et al. Sci Rep. .

Abstract

Graphite-coated magnetic cobalt nanoparticles (CoNPs) decorated with hindered phenolic antioxidant analogues of 2,6-di-tert-butyl-4-methylphenol (BHT, E321) provided easily removable nanoantioxidants capable of preventing the autoxidation of organic solvents as tetrahydrofuran (THF).

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Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Schematic preparation, use and removal of nano-magnetic stabilizer systems.
Figure 2
Figure 2
Synthesis of BHT-like derivatives 1 and 2 suitable for the functionalization of CoNPs-N3. (a) 2,6-di-tert-butylphenol, (CF3CO)2O, rt, 3 h; (b) activate Zn, HCl, CH3COOH, EtOH, reflux, 15 h; (c) SOCl2, MeOH, rt, 1 h; (d) MeMgBr, Et2O, rt, 16 h; (e) 2-tert-butyl-4-methylphenol, CH3SO3H, 1,2-DCE, rt, 24 h.
Figure 3
Figure 3
Functionalization of CoNPs-N3 under CuAAC conditions; Left: FT-IR (KBr pellets) spectrum of CoNPs-N3 (curve a) and FT-IR spectra of CoNPs-A80 3 (curve c) and CoNPs-A94 4 (curve b).
Figure 4
Figure 4
Oxygen consumption measured during the autoxidation of cumene (4.3 M) initiated by AIBN (25 mM, rate of initiation (Ri) (2.2 ± 0.1) × 10−9 M−1 s−1 at 30 °C in benzonitrile without antioxidants (dashed line) or in the presence of (a) CoNPs-N3 (0.18 mg/mL); (b) BHT (18 μM), (c) CoNPs-A94 4 and (d) CoNPs-A80 3 (both 0.18 mg/mL, corresponding to 18 μM of linked BHT units). Magnetic nanoparticles adhered to the stir bar (inset A) but were homogeneously dispersed in solution when stirring was switched on (inset B).
Figure 5
Figure 5
CoNPs-Antiox 3 and 4 suspended in THF (inset A) and recovered with a neodymium magnet (inset B), peroxide test strips (QUANTOFIX Peroxide 100, inset C).
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