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Intensification of cyclohexanone purification stage from impurities in caprolactam production using phase transfer catalysis

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

Impurities in the oxidate, which was produced in the oxidation of cyclohexane in an industrial environment, were analyzed and identified. It is found that the amount of esters and ethers is 30% of the impurities produced, among which a cyclohexyl ethers amount is more than 50%. The process of purifying the oxidate from the impurities by hydrolysis in the presence of phase transfer catalysts and without them was studied. It has been shown that the use of trioctylmethyl ammonium chloride (Aliquat-336) in the the stage of saponification of esters enabled a removal of 90–96% of esters with reducing of reaction time in a 1.5-fold, in contrast to non-catalytic process.

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References

  1. Musser, M.T., Cyclohexanol and Cyclohexanone: Ullmann’s Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2000.

    Google Scholar 

  2. Hermans, I., Jacobs, P., and Peeters, J., Chem. Eur. J., 2007, vol. 13, pp. 754–776.

    Article  CAS  Google Scholar 

  3. Lupanov, P.A., Chichagov, V.N., Chadaev, V.P., et al., Khim. Prom-st’, 1975, no. 5, pp. 336–338.

    Google Scholar 

  4. Glazko, I.L., Levanova, S.V., Martynenko, E.A., and Sokolova, A.A., Russ. J. Appl. Chem., 2011, vol. 84, no. 10, pp. 1767–1771.

    Article  CAS  Google Scholar 

  5. Naik, D. and Doraiswamy, L.K., Reactors, Kinetics a. Catalysis, 1998, vol. 44, pp. 612–646.

    CAS  Google Scholar 

  6. Wanga, M.L., Vivekanand, P.A., Yu, M.C., J. Taiwan Inst. Chem. Eng., 2012, vol. 43, pp. 207–214.

    Article  Google Scholar 

  7. Paliwal, N.R. and Mungray, A.K., Polym. Degradation a. Stability, 2013, vol. 98, no. 10, pp. 2094–2101.

    Article  CAS  Google Scholar 

  8. Asai, S., Nakamura, H., and Furuichi, Y., Am. Inst. Chem. Eng. J., 1992, vol. 38, no. 3, pp. 397–404.

    Article  CAS  Google Scholar 

  9. Asai, S., Nakamura, H., Yamada, M., Chem. Eng., 1997, vol. 67, pp. 19–25.

    Article  CAS  Google Scholar 

  10. NIST Chemistry Webbook. http://webbook.nist.gov

  11. Lebedev, A.T., Mass-spektrometriya v organicheskoi khimii (Mass Spectrometry in Organic Chemistry), Moscow: BINOM. Laboratoriya znanii, 2003.

    Google Scholar 

  12. Yufit, S.S., Zh. Vses. Khim. Obshch. im. D.I. Mendeleeva, 1986, vol. 31, no. 2, pp. 134–142.

    CAS  Google Scholar 

Download references

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Correspondence to E. A. Martynenko.

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Original Russian Text © E.A. Martynenko, I.L. Glazko, S.V. Levanova, Yu.V. Portnova, 2014, published in Zhurnal Prikladnoi Khimii, 2014, Vol. 87, No. 7, pp. 907–912.

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Martynenko, E.A., Glazko, I.L., Levanova, S.V. et al. Intensification of cyclohexanone purification stage from impurities in caprolactam production using phase transfer catalysis. Russ J Appl Chem 87, 899–903 (2014). https://doi.org/10.1134/S107042721407009X

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  • DOI: https://doi.org/10.1134/S107042721407009X

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