Skip to main content
Log in

Synthesis, Identification, and Isolation of Esters of Pentaerythritol and Linear С4–С7 Carboxylic Acids

Petroleum Chemistry Aims and scope Submit manuscript

Abstract

Various procedures for thermal esterification of individual monobasic С4–С7 carboxylic acids with pentaerythritol in an excess of the corresponding acid in the presence of a solvent or without it in combination with azeotropic distillation of water released in the reaction were studied. Four tetraesters of pentaerythritol (PE) and C4–C7 acids were synthesized, isolated, and purified (to ≥99 wt % purity according to GLC) and were identified by GC–MS. The physicochemical characteristics of the products were determined. The dependence of the induction effect determined by the alkyl chain length in the acid molecule on the esterification rate was studied; at 100–110°C, 90% yield was reached in 30 h for PE tetrabutyrate and in 13–14 h for С5–С7 tetraesters. The purity of the tetraesters was higher than 99 wt % after the purification, and the yield was 78–85%.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.

Similar content being viewed by others

REFERENCES

  1. Nagendramma, P. and Kaul, S., Sustain. Energy Rev., 2012, vol. 16, pp. 764–774. https://doi.org/10.1016/j.rser.2011.09.002

    Article  CAS  Google Scholar 

  2. Campanella, A., Rustoy, E., Baldessari, A., and Baltanás, M.A., Bioresource Technol., 2010, pp. 245– 254. https://doi.org/10.1016/biortech.2009.08.035

  3. Kalam, M.A. and Masjuki, H.H., J. Sci. Ind. Res., 2005, vol. 64, no. 11, pp. 920–927.

    CAS  Google Scholar 

  4. Soni, S. and Agarwal, M., Green Chem. Lett. Rev., 2014, pp. 359–382. https://doi.org/10.1080/17518253.2014.959565

  5. Kalaitan, E.N., Smazochnye masla dlya reaktivnykh dvigatelei (Lubricating Oils for Jet Engines), Moscow: Khimiya, 1968.

  6. Yanovskii, L.S., Dubovkin, N.F., Yanovskii, L.S., Dubovkin, N.F., and Galimov, F.M., Goryuche-smazochnye materialy dlya aviatsionnykh dvigatelei (Fuels and Lubricating Materials for Aviation Engines), Kazan, 2002.

  7. Tonkonogov, B.P., Popova, K.A., and Khurumova, A.F., Tr. Ross. Gos. Univ. Nefti Gaza im. I.M. Gubkina, 2015, no. 1(278), pp. 109–120.

    Google Scholar 

  8. Lin, L. and Kedzierski, M.A., Int. J. Refrig., 2020, vol. 118, pp. 188–201. https://doi.org/10.1016/j.ijrefrig.2020.07.004

    Article  CAS  Google Scholar 

  9. Mancini, G., Imparato, L., and Berti, F., Patent US 4317780, Publ. March 2, 1982.

  10. Martem’yanov, V.S., Report of the All-Union Rersearch Inst. of Oil Refining, 1988.

  11. Bohner, G.E., Krimmel, J.A., Schmidt-Collerus, J.J., and Stacy, R.D., J. Сhem. Еng. Data, 1962, vol. 7, no. 4, pp. 547–553. https://doi.org/10.1021/je60015a035

    Article  CAS  Google Scholar 

  12. Yunus, R., Fakhru’l-Razi, A., Ooi, T.L., Omar, R., and Idriset, A., Ind. Eng. Chem. Res., 2005, vol. 44, pp. 8178–8183. https://doi.org/10.1021/ie050530

    Article  CAS  Google Scholar 

  13. Emel’yanov, V.V., Krasnykh, E.L., and Portnova, S.V., Russ. J. Phys. Chem. A, 2020, vol. 94, no. 10, pp. 2168–2176. https://doi.org/10.1134/S003602442010009X

    Article  Google Scholar 

  14. Nur, A.M.A., Robiah, Y., Umer, R., and Nurin, W.M.Z., Tribol. Int., 2016, vol. 93, pp. 43–49. https://doi.org/10.1016/j.triboint.2015.09.014

    Article  CAS  Google Scholar 

  15. Quinchia, L.A., Delgado, M.A., Reddyhoff, T., Gallegos, C., and Spikes, H.A., Tribol. Int., 2014, vol. 69, pp. 110–117. https://doi.org/10.1016/j.triboint.2013.08.016

    Article  CAS  Google Scholar 

  16. Kishore, K. and Shobha, H.K., J. Phys. Chem., 1992, vol. 96, no. 20, pp. 8161–8168. https://doi.org/10.1021/j100199a063

    Article  CAS  Google Scholar 

  17. Razzouk, A., Mokbel, I., García, J., Fernandez, J., Msakni, N., and Jose, J., Fluid Phase Equil., 2007, vol. 260, no. 2, pp. 248–261. https://doi.org/10.1016/j.fluid.2007.07.029

    Article  CAS  Google Scholar 

  18. Ewen, J.P., Gattinoni, C., Thakkar, F.M., Morgan, N., Spikes, H.A., and Dini, D., Materials (Basel), 2016, vol. 9, no. 8, 651. https://doi.org/10.3390/ma9080651

  19. Bair, S., High Pressure Rheology for Quantitative Elastohydrodynamics, 2019, pp. 1–19. https://doi.org/10.1016/B978-0-444-64156-4.00001-5

  20. El-Magly, I.A., Nagib, H.K., and Mokhtar, W.M., Egypt. J. Petrol., 2013, vol. 22, no. 1, pp. 169–177. https://doi.org/10.1016/j.ejpe.2012.09.008

    Article  Google Scholar 

  21. Breusch, F.L. and Oğuzer, M., Chem. Ber., 1955, vol. 88, pp. 1511–1518.

    Article  CAS  Google Scholar 

  22. Sushkova, S.V., Levanova, S.V., Glazko, I.L., and Aleksandrov, A.Yu., Tonk. Khim. Tekhnol., 2017, vol. 12, no. 3, pp. 28–32. https://doi.org/10.32362/2410-6593-2017-12-3-28-32

    Article  CAS  Google Scholar 

  23. Marochkin, D.V., Noskov, Yu.G., Kron, T.E., Karchevskaya, O.G., and Korneeva, G.A., Nauch.-Tekh.’ Vestn. OAO NK Rosneft’, 2016, no. 45, pp. 74–81

    Google Scholar 

  24. Aleksandrov, A.Yu., Krasnykh, E.L., Levanova, S.V., Glazko, I.L., and Lukina, O.D., Tonk. Khim. Tekhnol., 2019, vol. 14, no. 1, pp. 66–74. https://doi.org/10.32362/2410-6593-2019-14-1-66-74

    Article  CAS  Google Scholar 

  25. Traven’, V.F., Organicheskaya khimiya. Uchebnoe posobie dlya vuzov (Organic Chemistry. Textbook for Higher Schools), Moscow: Laboratoriya Znanii, 2019, vol. 3.

  26. Bohner, G.E., Krimmel, J.A., and Schmidt-Collérus, J.J., J. Chem. Eng. Data, 1962, vol. 7, pp. 547–553.

    Article  CAS  Google Scholar 

Download references

Funding

The study was financially supported by the Russian Foundation for Basic Research (project no. 20-38-90141).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. L. Krasnykh.

Ethics declarations

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

Additional information

Translated from Neftekhimiya, 2021, Vol. 61, No. 5, pp. 652–658 https://doi.org/10.31857/S0028242121050087.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Emelyanov, V.V., Krasnykh, E.L., Fetisov, D.A. et al. Synthesis, Identification, and Isolation of Esters of Pentaerythritol and Linear С4–С7 Carboxylic Acids. Pet. Chem. 61, 1027–1032 (2021). https://doi.org/10.1134/S0965544121090048

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0965544121090048

Keywords:

Navigation