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Acylation of Resorcinol with Pyromellitic Dianhydride

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

A procedure was developed for preparing resorcinolpyromellitein [3,3,7,7-tetrakis(4-hydroxy-2,2ʹ-oxydiphenyl)pyromellitide] by acylation of resorcinol with pyromellitic dianhydride using tin tetrachloride as a catalyst (120–210°С, 30 h, reactant ratio pyromellitic dianhydride : SnCl4 : resorcinol = 1.0 : 2.5 : 5.0). The structure of the target product was proved by elemental analysis, thin-layer chromatography, UV and IR spectroscopy, 1H NMR spectroscopy, differential scanning calorimetry, and high-performance liquid chromatography with mass-spectrometric detection. The synthesized product exhibits increased hydrophilicity and imparts fluorescence properties to aqueous solutions when dissolved in a small amount (5 × 10–4 wt %), which allows it to be recommended as a chemical marker in tracer exploration of oil strata at oil fields.

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Funding

The study was supported by the Government of the Khanty-Mansi autonomous okrug—Yugra (order no. 1234 of August 11, 2017 on the competition of scientific projects in the field of basic and applied research) and was performed within the framework of the government assignment for the Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences.

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Correspondence to V. P. Nekhoroshev.

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Translated from Zhurnal Prikladnoi Khimii, No. 2, pp. 233–239, January, 2021 https://doi.org/10.31857/S0044461821020110

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Nekhoroshev, V.P., Nifant’ev, I.E. Acylation of Resorcinol with Pyromellitic Dianhydride. Russ J Appl Chem 94, 217–222 (2021). https://doi.org/10.1134/S1070427221020117

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  • DOI: https://doi.org/10.1134/S1070427221020117

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