Термодинамические аспекты сорбции и разделения энантиомеров некоторых монотерпенов на капиллярной колонке β-DEX 120
Ключевые слова:
хиральная газовая хроматография, капиллярные колонки, терпены, термодинамика сорбции, комплексообразование «гость-хозяин», разделение энантиомеров
Аннотация
В интервале температур 80-140оС для оптических изомеров монотерпенов (лимонена,
камфена, α-пинена, ментола) определены факторы удерживания на капиллярных колонках типа
WCOT с неподвижными фазами на основе полидифенилдиметилсилоксана с добавкой 20 %
перметилированного β-циклодекстрина (колонка β-DEX 120) и без добавки (колонка DB-35ms).
Определены термодинамические характеристики сорбции монотерпенов из газовой фазы и
комплексообразования "гость - хозяин" в полимерном растворе. Дано термодинамическое
обоснование энантиоселективности и ее температурной зависимости. Рассчитаны температуры
компенсации, выше которых происходит обращение выхода энантиомеров.
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Литература
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carbosilane as stationary phase for GC, Chinese
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Yu.G. Thermodynamics of the adsorption of
volatile organic compounds in a binary
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stationary phase, as measured by gas
chromatography, Russian journal of physical
chemistry A, 2013, Vol. 87, No 5, pp. 861-864.
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polimernoi fazy, soderzhashchei atsetilirovannyi
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phase comprising an acetylated β-cyclodextrin],
Sorbcionnye i khromatograficheskie processy,
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svoistva binarnykh nepodvizhnykh faz na
osnove polidimetilsiloksana i polietilenglikolya
i dobavki geptakis(2,3-O-diatsetil-6-O-tozil)-β-
tsiklodekstrina v usloviyakh gazovoi
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No 36, pp. 912-925.
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opredelenie enantiomerov: Per. s angl. M.: Mir.
1991, 268 p.
14. Onuchak L.A., Kudryashov S.Yu. Using
reverse gas–liquid chromatography to determine
the thermodynamic functions of sorption in a
system of constant volume, Russian Journal of
Physical Chemistry A, 2014, Vol. 88, No 10,
pp. 1785-1789.
15. Asztemborska M., Sybilska D.,
Nowakowski R. et al. Chiral recognition ability
of α-cyclodextrin with regard to some
monoterpenoids under gas-liquid
chromatographic conditions, J. Chromatogr A,
2003, Vol. 1010, pp. 233-242.
16. Skorka M., Asztemborska M., Zukowski
J. Thermodynamic studies of complexation and
enantiorecognition processes of monoterpenoids
by α- and β-cyclodextrin in gas
chromatography, J. Chromatogr. A, 2005, Vol.
1078, pp.136-143.
17. Ma S., Shen S., Haddad N. et al.
Chromatographic and spectroscopic studies on
the chiral recognition of sulfated-β-cyclodextrin
as chiral mobile phase additive enantiomeric
separation of chiral amine, J. Chromatogr. A,
2009, Vol. 1216, pp. 1232-1240.
18. Korol' A.N. Nepodvizhnye fazy v gazozhidkostnoi
khromatografii. Spravochnik. M.:
Khimiya, 1985. 240 p.
19. Caira M.R., Bourne S.A., Dean P.M. et al.
New crystalline forms of permethylated β-
cyclodextrin, Chem. Commun, 2004, pp. 2216-
2217.
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cyclodextrins, Chem. Rew, 2014, No 114 (21),
pp. 10735-10806.
21. Blatov V.A., Shevchenko A.P.,.]
Proserpio D.M. Applied Topological Analysis
of Crystal Structures with the Program Package
ToposPro. Crystal Growth Des, 2014, Vol. 14,
pp. 3576.
22. webbook/nist.gov
23. Stid Dzh.V., Etvud Dzh. L.
Supramolekulyarnaya khimiya. M.: IKTs
«Akademkniga», 2007, 480 p.
pharmaceutics: past, present and future,
Nat. Rew, 2004, No 3, pp. 1023-1035.
2. Schurig V. Chiral separations using gas
chromatography, Trends in analytical chemistry,
2002, Vol. 21, No 9-10, pp. 647-661.
3. Juvancz Z. The role of cyclodextrins in
chiral selective chromatography, Trends in
analytical chemistry, 2002, Vol. 21, No 5, p
p. 379-388.
4. Shitangkoona A., Yanchindaa J.,
Shiowatana J. Thermodynamic study on the gas
chromatographic separation of the enantiomers
of aromatic alcohols using heptakis(2,3-di-Omethyl-6-O-tret-butyldimethylsilyl)-β-cyclodextrin
as a stationary phase, J. Chromatogr. A,
2004, Vol. 1049, pp. 223-226.
5. Tisse S., Peulon-Agasse V., Cardina P. Et
al. Capillary gas chromatographic properties of
three new mono-esterpermethylated β-cyclodextrin
derivatives, Anal. chim. Acta, 2006,
Vol. 560, pp. 207-217.
6. Guo Wen Chen, Chen Zhang, Wen Jie Li et
al. Synthesis and characterization of β-
cyclodextrin modified hyperbranched
carbosilane as stationary phase for GC, Chinese
Chemical Letters, 2012, Vol. 23, pp. 1259-1262.
7. Volker S. Gas chromatographic
enantioseparation of derivatized -amino acids
on chiral stationary phases-Past and present, J.
Chromatog. B, 2011, Vol. 879, pp. 3122-3140.
8. Onuchak L.A., Platonov V.I., Kuraeva
Yu.G. Thermodynamics of the adsorption of
volatile organic compounds in a binary
polydimethylsiloxane-permethylated β-cyclodextrin
stationary phase, as measured by gas
chromatography, Russian journal of physical
chemistry A, 2013, Vol. 87, No 5, pp. 861-864.
9. Asztemborska M., Nowakowski R.,
Sybilska D. Separation ability and stoichiometry
of cyclodextrin complexes, J. Chromatogr. A,
2000, Vol. 902, pp. 381-387.
10. Onuchak L.A., Kuraeva Yu.G., Platonov
V.I. et al. Gazokhromatograficheskoe
Евдокимова и др. / Сорбционные и хроматографические процессы. 2015. Т. 15. Вып. 2
300
issledovanie sorbtsionnykh svoistv smeshannoi
polimernoi fazy, soderzhashchei atsetilirovannyi
β-tsiklodekstrin [Gas chromatographic study of
the sorption properties of the polymer mixed
phase comprising an acetylated β-cyclodextrin],
Sorbcionnye i khromatograficheskie processy,
2012, Vol.12, No 3, pp. 345-354.
11. Kuraeva Yu.G., Onuchak L.A., Voronina
E.Yu. et al. Sorbtsionnye i enantioselektivnye
svoistva binarnykh nepodvizhnykh faz na
osnove polidimetilsiloksana i polietilenglikolya
i dobavki geptakis(2,3-O-diatsetil-6-O-tozil)-β-
tsiklodekstrina v usloviyakh gazovoi
khromatografii, Sorbcionnye i
khromatograficheskie processy, 2014, Vol. 14,
No 36, pp. 912-925.
12. Tyukavkina N.A., Baukov Yu.I.
Bioorganicheskaya khimiya. M: Meditsina,
1991, 473 p.
13. Allenmark S. Khromatograficheskoe
opredelenie enantiomerov: Per. s angl. M.: Mir.
1991, 268 p.
14. Onuchak L.A., Kudryashov S.Yu. Using
reverse gas–liquid chromatography to determine
the thermodynamic functions of sorption in a
system of constant volume, Russian Journal of
Physical Chemistry A, 2014, Vol. 88, No 10,
pp. 1785-1789.
15. Asztemborska M., Sybilska D.,
Nowakowski R. et al. Chiral recognition ability
of α-cyclodextrin with regard to some
monoterpenoids under gas-liquid
chromatographic conditions, J. Chromatogr A,
2003, Vol. 1010, pp. 233-242.
16. Skorka M., Asztemborska M., Zukowski
J. Thermodynamic studies of complexation and
enantiorecognition processes of monoterpenoids
by α- and β-cyclodextrin in gas
chromatography, J. Chromatogr. A, 2005, Vol.
1078, pp.136-143.
17. Ma S., Shen S., Haddad N. et al.
Chromatographic and spectroscopic studies on
the chiral recognition of sulfated-β-cyclodextrin
as chiral mobile phase additive enantiomeric
separation of chiral amine, J. Chromatogr. A,
2009, Vol. 1216, pp. 1232-1240.
18. Korol' A.N. Nepodvizhnye fazy v gazozhidkostnoi
khromatografii. Spravochnik. M.:
Khimiya, 1985. 240 p.
19. Caira M.R., Bourne S.A., Dean P.M. et al.
New crystalline forms of permethylated β-
cyclodextrin, Chem. Commun, 2004, pp. 2216-
2217.
20. Gregorio C. Rewiev: A history of
cyclodextrins, Chem. Rew, 2014, No 114 (21),
pp. 10735-10806.
21. Blatov V.A., Shevchenko A.P.,.]
Proserpio D.M. Applied Topological Analysis
of Crystal Structures with the Program Package
ToposPro. Crystal Growth Des, 2014, Vol. 14,
pp. 3576.
22. webbook/nist.gov
23. Stid Dzh.V., Etvud Dzh. L.
Supramolekulyarnaya khimiya. M.: IKTs
«Akademkniga», 2007, 480 p.
Опубликован
2018-02-19
Как цитировать
Онучак, Л. А., Евдокимова, М. А., Кураева, Ю. Г., & Платонов, В. И. (2018). Термодинамические аспекты сорбции и разделения энантиомеров некоторых монотерпенов на капиллярной колонке β-DEX 120. Сорбционные и хроматографические процессы, 15(2), 288-300. https://doi.org/10.17308/sorpchrom.2015.15/277
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