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High-Boiling By-Products of the Synthesis of Trimethylolpropane and Their Processing into Esters

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

According to the data of 1H NMR spectroscopy, trimethylolpropane, di(trimethylolpropane), linear formals, and structures including a fragment of a cyclic formal are the main components of the bottom residue after vacuum distillation of raw trimethylolpropane yielded in the technological process of n-butyral condensation with formaldehyde proceeding by the Cannizzaro–Tishchenko reaction. The content of other impurities is minor. The heavy bottoms can be converted in high yield to a mixture of esters of trimethylolpropane and di(trimethylolpropane) by esterification with n-pentanoic acid. Such esters are characterized by a low pour point, high chemical resistance, thermal stability, and good viscosity-temperature properties, as well as sufficient compatibility with various plastic materials, and therefore, can be employed as lubricants, polymer plasticizers, and other products.

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Authors and Affiliations

  1. LLC “United Research and Development Center”, 119333, Moscow, Russia

    D. V. Marochkin, O. G. Karchevskaya, T. E. Kron, F. V. Ryzhkov, G. A. Korneeva & Yu. G. Noskov

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  1. D. V. Marochkin
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  2. O. G. Karchevskaya
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  3. T. E. Kron
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  4. F. V. Ryzhkov
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  5. G. A. Korneeva
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  6. Yu. G. Noskov
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Contributions

D.V. Marochkin: collection and analysis of scientific and technical information on the synthesis and isolation of trimethylolpropane, synthesis of trimethylolpropane, vacuum distillation of crude trimethylolpropane, isolation of distillation residue, development of conditions for gas-liquid chromatographic analysis; O.G. Karchevskaya: development of methods for the synthesis of the monocyclic formal form of trimethylolpropane, chromatographic analysis of the bottom residue; T.E. Kron: interpretation of nuclear magnetic resonance spectra, analysis and systematization of the results of the work; F.V. Ryzhkov: development of methods and carrying out esterification reactions of the bottom residue, carrying out chromatographic analysis of esters; G.A. Korneeva: collection and analysis of literature (including patent) data on by-products of the synthesis of trimethylolpropane, interpretation of the results of the work; Yu.G. Noskov: formulation of methods for the synthesis and chromatographic analysis of trimethylopropane and trimethylolpropane monocyclic formal, esterification methods, interpretation of spectral data, results of gas-liquid chromatographic analysis.

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Correspondence to D. V. Marochkin.

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The authors declare no conflict of interest requiring disclosure in this article.

Additional information

Translated from Zhurnal Prikladnoi Khimii, No. 5, pp. 656–665, May, 2022 https://doi.org/10.31857/S0044461822050127

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Marochkin, D.V., Karchevskaya, O.G., Kron, T.E. et al. High-Boiling By-Products of the Synthesis of Trimethylolpropane and Their Processing into Esters. Russ J Appl Chem 95, 717–725 (2022). https://doi.org/10.1134/S1070427222050123

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  • DOI: https://doi.org/10.1134/S1070427222050123

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