Gas-liquid chromatographic separation of saturated terpene hydrocarbons using glass capillary columns

Bazyl'chick, V.V.; Mistryukov, E. A.; Fedorov, P. I.; Belyaeva, K.V.

doi:10.1016/s0021-9673(00)95051-9

Cited by 3 publications

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“…The reaction is accompanied by formation of picrates when the conversion is carried out in aqueous solution. For this reason, a substantial excess of picryl chloride was used by Eppert and Schinke [2]. In our laboratory, a yellowbrown p r o d k t with poor chromatographic performance has been obtained in this way.…”

Section: Introductionmentioning

confidence: 99%

Picramidopropyl silica gel for “charge‐transfer” HPLC

Nondek

1985

J. High Resol. Chromatogr.

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Perkin Elmer 990 instrument equipped with an FID and an electronic integrator for the retention time measurements. The carrier gas was helium. Glass capillary columns (40 m X 0.25 mm i.d.) were coated using conventional methods [4]. Retention indices were calculated by an HP 9830A desk computer after optimization of the operating conditions as reported previously ~51. Results and DiscussionThe Kovats retention indices (IK) for the series of terpene alcohols at different temperatures and their temperature variations (6116T) and structural increments ( 6 H o~) are listed in Table 1.Retention indices increase with the polarity of the stationary phase (AIpEG.ov -200-250 IU). However, the variation of 1~ with column temperature (6ll6T) is lower for the stationary phase exhibiting higher selectivity for the alcohols (0.695-0.775 for OV-225 and 0.325-0.465 for PEG 20M).The structural incrementsforthe hydroxyl group (6HoH) are of the order of 730 and 550 IU for PEG 20M and OV-225, respectively. In general, the hydroxyl group does not significantly modify the chromatographic behavior of the alcohols with respect to the hydrocarbons. For example, the Al for an endo-exocyclic double bond (AIH.,) is 12 (OV-225) and 26 (PEG) for the alcohols and 18 (OV-225)and28(PEG)forthe hydrocarbons [l],at800C.However, there is one exception, namely, p-menth-3-en-9-01 (J) which gives structural increments ( 6 H o~) 100 and 70 IU lower than the rest of the alcohols. The decrease in polarity of this alcohol, which is the first to elute, can be explained by an intramolecular hydrogen bond between the olefinic hydrogen at C-3 and the hydroxylic oxygen.The resolution of cisltrans-p-menthanol isomers (A-B and F-G) increases with the polarity of the stationary phase as previously observed for the hydrocarbons [l] and is highly temperature dependent (Table 1). The trans isomers are the first to elute and also show lower 6H values, in agreement with their lower polarity.When the cyclohexane ring configuration is modified by a double bond (isomers D-E) the separation is more difficult.In conclusion it can be stated that the close relationship observed between the group of monoterpene alcohols and hydrocarbons relies on the additivity of the Kovats retention index system 161.However, significant deviations are observed when intramolecular interactions occur. Of practical interest is the increase in resolution of alkylcyclohexane cisltrans isomers with the polarity of the stationary phase. References[I] J. Albaiges and X . Guardino, Chromatographia 13 (1980)

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Section: Introductionmentioning

confidence: 99%

Picramidopropyl silica gel for “charge‐transfer” HPLC

Nondek

1985

J. High Resol. Chromatogr.

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“…In contrast to hydrocarbons [1,2], chromatographic data of terpene alcohols has not been systematically reported in the literature. Therefore, Kovats retention indices were calculated for these alcohols on two polar stationary phases, OV-225 and PEG 20M, at different temperatures, in order to understand their chromatographic behavior and extend the correlations previously established [l].…”

Section: Introductionmentioning

confidence: 99%