Influence of vacuum on kinetic of low quality rapeseed oil amidation by aminoethylethanolamine

Authors

  • Sergiy Kramarev LLC Chemrise Arkhitektorov str., 32, Kharkiv, Ukraine, 61174, Ukraine https://orcid.org/0000-0002-0076-8664
  • Alisher Husanov Auezov South Kazakhstan State University Tauke-Khan str., 5, Shymkent, Kazakhstan, 160012, Kazakhstan

DOI:

https://doi.org/10.15587/1729-4061.2016.74856

Keywords:

amidation, low­quality oils, alkylimidazolines, surfactants, rate constants

Abstract

The process of direct amidation of low­grade canola oil with high free fatty acids content has been researched. Influence of different technological parameters on consumption of reagents and accumulation of reaction products have been established for the temperature of reaction 160 °С. Concentrations of esters, free fatty acids, alkylimidazolines and amine components have been determined during the reaction time. Application of vacuum during the amidation process has great influence on free fatty acids consumption as well as on alkylimidazoline formation. Effective rate constants have been calculated for reactions of conversion of free fatty acids and esters into amides with and without vacuum. It has been determined that effective rate constant of free fatty acids consumption under atmospheric pressure is three times lower than under vacuum 40–60 mm. Hg. as well as those for esters. Along with an increase in free fatty acids consumption, the speed of alkylimidazolines formation rapidly increases with vacuum applying. Such effect is explained by shifting of equilibrium in reactions of free fatty acids consumption and alkylimidazoline formation by removing of reaction water by vacuum. Formation of amides of fatty acids and alkylimidazolines confirmed by IR­spectroscopy. 

Author Biographies

Sergiy Kramarev, LLC Chemrise Arkhitektorov str., 32, Kharkiv, Ukraine, 61174

PhD

Alisher Husanov, Auezov South Kazakhstan State University Tauke-Khan str., 5, Shymkent, Kazakhstan, 160012

PhD

Head of “Water problems” scientific laboratory

References

  1. Fainerman, V. B., Mobius, D., Miller, R. (2001). Surfactants: chemistry, interfacial properties, applications. Elsevier, 661.
  2. Tyagi, R., Tyagi, V. K., Pandey, S. K. (2007). Imidazoline and Its Derivatives : An Overview. Journal of Oleo Science, 56 (5), 211–222. doi: 10.5650/jos.56.211
  3. Kramarev, S., Melnik, A., Matveeva, T. et. al. (2013). Issledovanie polucheniya azotoproizvodnih zhirnich kislot. Sovremenniy Nauchniy Vestnik, 31 (170), 79–83.
  4. Malik, S., Melnik, A. (2013). Doslidzhennya oderzhannya kysen’ i azotovmisnuh pohidnyh zhirnuh kislot amiduvannyam llyanoyi oliyi. Vestnik NTU “KhPI”, 38, 157–160.
  5. Gomez, L. M., De La Escalera, L. M., Gutierrez, J. A. et. al. (2015). Patent 0315142 USA. Process to obtain imidazoline mixtures from vegetable oils. Declared: 01.07.2014; published: 05.11.2015.
  6. Bajpai, D., Tyagi, V. K. (2006). Fatty Imidazolines: Chemistry, Synthesis, Properties and Their Industrial Applications. Journal of Oleo Science, 55 (7), 319–329. doi: 10.5650/jos.55.319
  7. McKenna, A. L. (1982). Fatty amides, synthesis, properties, reactions and applications. Memphis, Tenn.: Witco Chemical Corporatioon, 225
  8. Bilyk, A., Bistline, R. G., Piazza, G. J., Feairheller, S. H., Haas, M. J. (1992). A novel technique for the preparation of secondary fatty amides. Journal of the American Oil Chemists’ Society, 69 (5), 488–491. doi: 10.1007/bf02540956
  9. Wu, Y., Herrington, P. R. (1997). Thermal reactions of fatty acids with diethylene triamine. Journal of the American Oil Chemists' Society, 74 (1), 61–64. doi: 10.1007/s11746-997-0120-2
  10. Bajpai, D., Tyagi, V. K. (2008). Microwave Synthesis of Cationic Fatty Imidazolines and their Characterization. Journal of Surfactants and Detergents, 11 (1), 79–87. doi: 10.1007/s11743-007-1057-z
  11. Yoo, S.-H., Kim, Y.-W., Chung, K., Baik, S.-Y., Kim, J.-S. (2012). Synthesis and corrosion inhibition behavior of imidazoline derivatives based on vegetable oil. Corrosion Science, 59, 42–54. doi: 10.1016/j.corsci.2012.02.011
  12. Liu, H., Hu, J., Zhou, X., Liu, D., Xu, B., Zhou, Y. (2015). Synthesis, Corrosion Inhibition Performance and Biodegradability of Novel Alkyl Hydroxyethyl Imidazoline Salts. Journal of Surfactants and Detergents, 18 (6), 1025–1031. doi: 10.1007/s11743-015-1725-3
  13. Finšgar, M., Jackson, J. (2014). Application of corrosion inhibitors for steels in acidic media for the oil and gas industry: A review. Corrosion Science, 86, 17–41. doi: 10.1016/j.corsci.2014.04.044
  14. Contreras, J. I. R., Negrete, P. S. D. et. al. (2015). A. Gutierrez et al Patent 0225351 USA. Process to obtain mixtures of imidazolines and corrosion inhibitors from coffee waste. Declared: 20.03.2014; published: 13.08.2015.
  15. Fröhlich, A., Rice, B., Vicente, G. (2010). The Conversion of Low Grade Tallow into Biodiesel-Grade Methyl Ester. Journal of the American Oil Chemists' Society, 87 (7), 825–833. doi: 10.1007/s11746-010-1561-6
  16. Jamal, Y., Rabie, A., Boulanger, B. O. (2014). Determination of methanolysis rate constants for low and high fatty acid oils using heterogeneous surface reaction kinetic models. Reaction Kinetics, Mechanisms and Catalysis, 114 (1), 63–74. doi: 10.1007/s11144-014-0780-5
  17. Rattanaphra, D., Harvey, A., Srinophakun, P. (2010). Simultaneous Conversion of Triglyceride/Free Fatty Acid Mixtures into Biodiesel Using Sulfated Zirconia. Topics in Catalysis, 53 (11-12), 773–782. doi: 10.1007/s11244-010-9463-2
  18. Hayyan, A., Hashim, M. A., Mirghani, M. E. S., Hayyan, M., AlNashef, I. M. (2014). Treatment of industrial low grade palm oil via esterification reaction using sonoreactor. Journal of Industrial and Engineering Chemistry, 20 (4), 2066–2070. doi: 10.1016/j.jiec.2013.09.033
  19. Shawkat, S. M., Demidov, I. (2013) Ispolzovaniye zhirnuh kislot soapstoka dlya polucheniya butilovih efirov zhirnih kislot. Vestnik NTU “KhPI”, 4, 130–134.
  20. Saiks, P. (1971). Mechanizmy reaktsii v organicheskoi himii. Мoscow: Chem, 196–197.
  21. Melnik, A., Matveeva, T., Papchenko, V. (2013). Polucheniye mono-, diacylglicerinov i etanolamidov zhirnuh kislot amidirovaniem podsolnechnogo masla. Lambert academic publishing, 264.
  22. Malik, S. G., Melnyk, A. P., Martseniuk, T. I. (2011). Kinetyka amiduvannia soievoi olii monoetanolaminom. Vestnik NTU “KhPI”, 16–19.
  23. Knorre, D. G., Krilova, L. F., Muzykantov, V. S. (1990). Fizicheskaia himiia. Мoscow: High sch., 416.
  24. Kramarev, S., Malik, S. (2014). Kinetic Regularities of Canola Oil Amidation by Aminoethylethanolamine. Studies in Chemical Process Technology (SCPT), 2, 17–20.
  25. Khusanov, A., Kaldybayeva, B., Kramarev, S., Melnik, A., Abilmagzhanov, A. (2015). Perspectives of low–grade vegetable oils utilization in surfactants production. Industrial technology and engineering, 2 (15), 35–41.
  26. Shmid, R., Sapunov, V. N. (1985). Informal kinetics. In the quest for chemical reactions. Мoscow: Mir, 264.
  27. Lisitskii, V. V., Akhmetchenko, Z. A., Alekhina, I. E., Murinov, Yu. I. (2007). Hydrolysis of 2–substituted and 1,2–disubstituted imidazolines, Russian Journal of Applied Chemistry, 80 (5), 761–766. doi: 10.1134/s107042720705014x
  28. Bistline, R. G., Hampson, J. W., LinField, W. M. (1983). Synthesis and properties of fatty imidazolines and their N-(2-aminoethyl) derivatives. Journal of the American Oil Chemists’ Society, 60 (4), 823–828. doi: 10.1007/bf02787436
  29. ASTM Standard D 2074–92 (1998). Standard test method for total, primary secondary and tertiary amine values of fatty amines by alternative indicator method.
  30. Tarasevich, B. N. (2012). IK spektru osnovnyh klassov organicheskih soedinenii: sprav. materiali. Мoscow, 54.
  31. Kushwaha, N., Saini, R. K., Kushwaha, S. K. (2011). Synthesis of some amide derivatives and their biological activity. International Journal of Chem Tech Research CODEN (USA), 3 (1), 203–209.

Downloads

Published

2016-08-24

How to Cite

Kramarev, S., & Husanov, A. (2016). Influence of vacuum on kinetic of low quality rapeseed oil amidation by aminoethylethanolamine. Eastern-European Journal of Enterprise Technologies, 4(6(82), 12–17. https://doi.org/10.15587/1729-4061.2016.74856

Issue

Section

Technology organic and inorganic substances