Synthesis, spectroscopic and computational investigation of N1,N4-bis(3-oxobutanoyl)benzene-1,4-dicarbohydrazide as a coupling component for azo dyes from waste poly(ethyleneterephthalate) bottle

EYDURAN F., SÜLEYMANOĞLU N., USTABAŞ R.

JOURNAL OF MOLECULAR STRUCTURE, vol.1244, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1244
  • Publication Date: 2021
  • Doi Number: 10.1016/j.molstruc.2021.130985
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: IR and NMR spectroscopy, DFT study, Coupling, PET, TEREPHTHALIC DIHYDRAZIDE, POLY(ETHYLENE-TEREPHTHALATE), DERIVATIVES, AMINOLYSIS, ACID, NMR
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

In order to contribute to the recycling of waste poly (ethylene terephthalate) (PET) in the industry; N1,N4-bis(3-oxobutanoyl)benzene-1,4-dicarbohydrazide (compound 1), a coupling component, was intended to be obtained from the condensation reaction between benzene-1,4-dicarbohydrazide (TPDH) and excess ethyl acetoacetate (EAA), and compound 1 were synthesized in good yield. Compound 1 was characterized by spectroscopic techniques (FTIR and NMR) and micro elemental analysis. Structural parameters, IR and NMR spectral data of compound 1 were obtained by DFT/B3LYP/6-311 ++G(d,p) method, considering two possible stable tautomeric forms as tetraketo and diketo-dienol. For detailed evaluation, theoretical IR and NMR data of compound 1 were compared with experimental ones. Results show that compound 1 predominantly exists in tetraketo form in solid state and DMSO. In this study, for the first time, a coupling component that can be used in the synthesis of azo dyes is obtained from TPDH, a degradation product of PET. This idea can lead to a significant contribution to saving raw materials in the industry and preventing environmental pollution caused by waste PET. (C) 2021 Elsevier B.V. All rights reserved.