DOI: https://doi.org/10.15587/1729-4061.2015.47732

Investigation of interaction of aminoethylethylenediamine with sunflower oil

Анатолий Павлович Мельник, Ольга Петровна Чумак, Сергей Григорьевич Малик, Алишер Евадиллович Хусанов

Abstract


The interaction reaction of sunflower oil with hydroxyethylethylenediamine at molar ratios of reactants of from 1: 1 to 1: 3, and temperatures of 393 K – 433 K by changes in the amine concentration over time was investigated, based on which the rate constants, activation energy and entropy were calculated. Using a kinetic first-order reaction model, the estimated thermodynamic parameters, changes in the amine concentration over time were calculated and compared with the experimental values. Analysis of variance between concentrations indicates that the amine concentration can be used for the sunflower oil amidation reaction control only at the initial stage. This is caused by the fact that both nitrogen and oxygen-containing products that also react with amine are formed in the oil amidation.


Keywords


sunflower oil; amidation; hydroxyethylethylenediamine; composition; kinetics; model; adequacy

References


Ivanskii, V. I. (1978). Chemistry of geterocyclyc compounds. High school, 560.

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

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

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

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

Faingold, S. I., Kuusk, A. E. (1984). Chemistry of anion and ampholityc nitrogen containing surface-active substances. Valgus, 290.

Linfield, W. M. (1984). Fatty oxazolines and imidazolines. Journal of the American Oil Chemists’ Society, 61 (2), 437–441. doi: 10.1007/bf02678810

Belov, P. S., Frolov, V. I. Chistyakov, B. E. (1975). New surface-active substances based on substituted imidazolines, 54.

Elster, C. H., Gibs, G. J. (1979). Pat. 4161604 USA. Process for making 1-hydroxyerhyl-2-undecyl-2-imidazoline. USA; LONZA AG; decl. 1.10.78; publ. 7.17.79.

Gabriel, R. (1984). Selective amidation of fatty methyl esters with N-(2-aminoethyl)-ethanolamine under base catalysis. Surfactants and detergents, 61 (5), 965–971.

Bon, R. S., Hong, C., Bouma, M. J., Schmitz, R. F., de Kanter, F. J. J., Lutz, M. et. al. (2004). Novel Multicomponent Reaction for the Combinatorial Synthesis of 2-Imidazolines. ChemInform, 35 (5), 3542–3553. doi: 10.1002/chin.200405056

Togo, H., Ishihara, M. (2006). An Efficient Preparation of 2-Imidazolines and Imidazoles from Aldehydes with Molecular Iodine and (Diacetoxyiodo)benzene. Synlett, 2, 227–230. doi: 10.1055/s-2005-923604

Watts, M. M. (1990). Imidazoline hydrolysis in alkaline and acidic media—A review. Journal of the American Oil Chemists’ Society, 67 (12), 993–995. doi: 10.1007/bf02541864

Serebryakov, B. R., Masagutov, R. M., Pravdin, V. H. (1989). New process of organic synthesis. Moscow:Chemistry, 400.

Phillips, B. M., Lace, R. B., Lambie, A. J. (1980). Pat. 4212983 USA. Manufacture of imidazoline compounds. USA; Albright & Wilson Limit Co; decl. 20.12.78; publ. 15.07.80.

Siggia, S., Khanna, J. (1983). Quantitative organic analysis by the functional groups. Мoscow: Chemistry, 672.

Shmid, R., Sapunov, V. N. (1985). Informal kinetics. In the quest for chemical reactions. Мoscow: Mir, 264.

Melnik, A. P., Matveeva, T. V., Papchenko, V. Yu. (2013). Obtaining of mono- diacylglycerols and ethanolamides by amidation oils. LLAP, 268.


GOST Style Citations


1. Иванский, В. И. Химия гетероциклических соединений [Текст] / Иванский В. И. – М.: Высшая школа, 1978. – 560 с.

2. Tyagi, R., Imidazoline and its derivatives: an overview [Text] / R. Tyagi, V. K. Tyagi, S. K. Pandey // Journal of oleo science. – 2007. – Vol. 56, Issue 5. – P. 211–222. doi: 10.5650/jos.56.211 

3. Bajpai, D. Fatty imidazolines: chemistry, synthesis, properties and their industrial application [Text] / D. Bajpai, V. K. Tyagi // Journal of oleo science. – 2006. – Vol. 55, Issue 7. – P. 319–329. doi: 10.5650/jos.55.319 

4. Wu, Y. Thermal Reactions of fatty acids with diethylenetriamine [Text] / Y. Wu, P. R. Herrington // Journal of the American Oil Chemists' Society. – 1997. – Vol. 74, Vol. 1. – Р. 61–64. doi: 10.1007/s11746-997-0120-2 

5. Bistline, R. G. Synthesis and properties of fatty imidazolines and their N-(2-aminoethyl) derivatives [Text] / R. G. Bistline, J. W. Hampson, W. M. LinField // Journal of the American Oil Chemists' Society. – 1983. – Vol. 60, Issue 4. – Р. 823–828. doi: 10.1007/bf02787436 

6 Файнгольд, С. И. Химия анионных и амфолитних азотсодержащих поверхностно-активных веществ [Текст] / С. И. Файнгольд, А. Э. Кууск, Х. Э. Кийк. – Таллин: Валгус, 1984. – 290 с.

7. Linfield, W. M. Fatty oxazolines and imidazolines [Text] / W. M. Linfield // Journal of the American Oil Chemists' Society. – 1984. – Vol 61, Issue 2. – Р. 437–441. doi: 10.1007/bf02678810 

8. Белов, П. С. Новые поверхностно-активные вещества на основе замещенных имидазолинов [Текст] / П. С. Белов, В. И. Фролов, Б. Ею Чистяков. – М.: ЦНИИТЭнефтехим, 1975. – 54 с.

9. Patent 4161604 USA. Process for making 1-hydroxyerhyl-2-undecyl-2-imidazoline [Text] / Elster C. H., Gibs G. J. – USA; LONZA AG; applied 1.10.78; published.7.17.79.

10. Gabriel, R. Selective amidation of fatty methyl esters with N-(2-aminoethyl)-ethanolamine under base catalysis [Text] / R. Gabriel // Surfactants and detergents. – 1984. – Vol. 61, Issue 5. – Р. 965–971.

11. Bon, R. S. Multicomponent synthesis of 2-imidazolines [Text] / R. S. Bon, C. Hong, M. J. Bouma, R. F. Schmitz, F. J. J. de Kanter, M. Lutz et. al. // Journal of organic chemistry. – 2005. – Vol. 70. – Р. 3542–3553. doi: 10.1002/chin.200405056 

12. Togo, H. An efficient preperation of 2-imidazolines and imidazoles from aldehydes with molecular iodine and (diacetoxyido)benzene [Text] / H. Togo, M. Ishihara // Synlett. – 2006. – Issue 2. – P. 227–230. doi: 10.1055/s-2005-923604 

13. Watts, M. M. Imidazoline hydrolysis in alkaline and acidic media – a review [Text] / M. M. Watts // Surfactants and detergents. – 1990. – Vol. 67, Issue 12. – P. 993–995. doi: 10.1007/bf02541864 

14. Серебряков, Б. Р. Новые процессы органического синтеза [Текст] / Б. Р. Серебряков, Р. М. Масагутов, В. Г. Правдин. – М: Химия, 1989. – 400 с.

15. Patent 4212983 USA. Manufacture of imidazoline compounds [Text] / Phillips B. M., Lace R. B., Lambie A. J. – USA; Albright & Wilson Limit Co; applied 20.12.78; published 15.07.80.

16. Сиггиа, C. Количественный органический анализ по функциональным группам [Текст] / С. Сиггиа, Дж. Х. – М.: Химия, 1983. – 672 с.

17. Шмид, Р. Неформальная кинетика. В поисках путей химических реакций [Текст] / Р. Шмид, В. Н. Сапунов; пер. с англ. – М.: Мир, 1985. – 264 с.

18. Мельник, А. П. Получение моно-, диацилглицеринов и этаноламидов амидированием масел [Текст] / А. П. Мельник, Т. В. Матвеева, В. Ю. Папченко. – LLAP, 2013. – 268 c.






Copyright (c) 2015 Анатолий Павлович Мельник, Ольга Петровна Чумак, Сергей Григорьевич Малик, Алишер Евадиллович Хусанов

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ISSN (print) 1729-3774, ISSN (on-line) 1729-4061