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Microwave Synthesis and Antibacterial Activity of 1,4-Bis (5-aryl-1,3,4-oxadiazole-2-yl) Benzene Derivatives from Terephthalic Dihydrazide Obtained Through Aminolysis of PET Bottle Waste

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Abstract

Recycling of waste PET bottles was attempted using aminolytic depolymerization with hydrazine monohydrate in the presence of NiCl2 and MgCl2 as catalysts, under reflux. The reaction was carried out in a domestic microwave oven of 700 W with suitable modification. Terephthalic dihydrazide (TPDH) was obtained in only 10 min as a pure product with 86 % yield as compared to 4 h by conventional heating. Various 1,4-bis(5-aryl-1,3,4-oxadiazole-2-yl) benzene (2a–f) derivatives were prepared from TPDH by treatment with appropriate aromatic acids in the presence of phosphoryl chloride and thionyl chloride, under microwave irradiation, which required only 20 min. The structures of the synthesized compounds were confirmed by FTIR, melting point and NMR. These compounds were found to possess antibacterial activity comparable to commercial products.

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Acknowledgments

The authors acknowledge the financial support received from the Council of Scientific and Industrial Research (CSIR), New Delhi, India.

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Authors and Affiliations

  1. Department of Fibres and Textile Processing Technology, Institute of Chemical Technology (University Under Section-3 of UGC Act 1956), N. Parekh Marg, Matunga, Mumbai, 400019, India

    Yogesh S. Parab & Sanjeev R. Shukla

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  1. Yogesh S. Parab
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  2. Sanjeev R. Shukla
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Correspondence to Sanjeev R. Shukla.

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Figure 1

Spectra of Terephthalic dihydrazide (TPDH) (a) FTIR (b) proton NMR (TIFF 662 kb)

Figure 2

Spectra of 1, 4-bis (5- phenyl- 1, 3, 4- oxadiazol- 2- yl) benzene (a) FTIR (b) proton NMR (TIFF 590 kb)

Figure 3

Spectra of 1, 4- bis (5- (4- nitrophenyl) -1, 3, 4- oxadiazol- 2- yl) benzene, (a) FTIR (b) proton NMR (TIFF 467 kb)

Figure 4

Spectra of 1, 4- bis (5- (4- chlorophenyl) -1, 3, 4- oxadiazol- 2- yl) benzene (a) FTIR (b) proton NMR (TIFF 478 kb)

Figure 5

Spectra of 1, 4- bis (5- (4- hydroxyphenyl) - 1, 3, 4- oxadiazol- 2- yl) benzene (a) FTIR (b) proton NMR (TIFF 536 kb)

Figure 6

Spectra of 1, 4- bis (5- (4- methoxyphenyl) - 1, 3, 4- oxadiazol- 2- yl) benzene (a) FTIR (b) proton NMR (TIFF 611 kb)

Figure 7

Spectra of 1, 4- bis (5- (4- aminophenyl) - 1, 3, 4- oxadiazol- 2- yl) benzene (a) FTIR (b) proton NMR (TIFF 532 kb)

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Parab, Y.S., Shukla, S.R. Microwave Synthesis and Antibacterial Activity of 1,4-Bis (5-aryl-1,3,4-oxadiazole-2-yl) Benzene Derivatives from Terephthalic Dihydrazide Obtained Through Aminolysis of PET Bottle Waste. Waste Biomass Valor 4, 23–27 (2013). https://doi.org/10.1007/s12649-012-9128-4

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