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Synthesis, Characterization, and Optimum Reaction Conditions of Oligo-Benzylidene-3′-Hydroxyaniline

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Abstract:

In this study, the oxidative polycondensation reactions of benzylidene-3′-hydroxyaniline(B-3′-HA)with air, H 2 O 2 , and NaOCl were studied in an aqueous alkaline medium at 40–90°C. Oligobenzylidene-3′-hydroxyaniline O-B-3′-HA)was characterized by 1 H-NMR, 13 C-NMR, FT-IR, UV-Vis, size exclusion chromatography(SEC), and elemental analysis. With NaOCl oxidant, the conversion of B-3′-HA was 98.0%under optimum conditions such as[B–3′–HA] 0 =[NaOCl] 0 =[KOH] 0 =0.1015mol/L at 50°C for 5h. H 2 O 2 was less active than O 2 and NaOCl. According to the SEC analysis, the number-average molecular weight(M n ), weight-average molecular weight(M w ), and polydispersity index(PDI)values were found to be 2640g mol −1 , 5130g mol −1 , and 1.942 using NaOCl, and 1960g mol −1 , 3170g mol −1 , and 1.615 using air, and 2370g mol −1 , 4720g mol −1 , and 1.990 using H 2 O 2 , respectively. Thermal analyses indicate that O-B-3′-HA is stable against thermo-oxidative decomposition.

Keywords: Air oxidation; H 2 O 2; NaOCl; Oligo-benzylidene-3′-hydroxyaniline; Oxidative polycondensation; Thermal analysis

Document Type: Research Article

DOI: https://doi.org/10.1080/1023660490890529

Affiliations: Department of Chemistry, Çanakkale Onsekiz Mart University, Çanakkale, Turkey

Publication date: 2004-01-01

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