Gas chromatographic determination of vapour pressures of pheromone-like compounds IV. Acetates, a reinvestigation

Koutek, Bohumı́r; Hoskovec, Michal; Vrkočová, Pavlı́na; Feltl, L.

doi:10.1016/s0021-9673(96)00775-3

Cited by 13 publications

(13 citation statements)

References 27 publications

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“…In the present article, all experimental data were treated using eq in its simplified version that is, assuming the ratio of activity coefficients γ s ∞ ( T )/γ x ∞ ( T ) is unity and a single standard reference compound is needed (GLC-RT1S). This approach has been used by a number of authors. ,,− It should be stressed that the only difference between exploitation of eq and using the Hamilton approach (eq ) lies in smoothing retention times with a two-parameter equation, as shown in Figures S1 to S4 in the Supporting Information; only eq will be considered in the remainder of this paper. However, previous approaches have typically required serious approximations and/or extrapolations to be made, necessitating a subsequent calibration with more or less related compounds.…”

Section: Results and Discussionmentioning

confidence: 99%

Extracting Vapor Pressure Data from GLC Retention Times. Part 1: Analysis of Single Reference Approach

Koutek

Mahnel²,

Šimáček³

et al. 2017

J. Chem. Eng. Data

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The vapor pressures of 52 compounds including n-alkanes and their monosubstituted derivatives, as well as chloro- and alkylbenzenes were determined exploring the gas chromatographic relative retention time (GLC-RT) technique in its simplest form, that is, using a single reference standard and neglecting the activity coefficient effect (GLC-RT1S). The selection of compounds was limited to those which are in the liquid state under the measurement conditions and for which high-quality vapor pressures obtained by direct methods are available at temperatures of GLC measurements. This approach should eliminate possible secondary error sources (such as data extrapolation or recalculation from supercooled liquid to solid phase or vice versa). On the basis of a thorough comparison of the GLC-RT1S-based and directly measured vapor pressures for the group of (functionalized) n-alkanes and by exploiting n-alkanes as reference solutes it is clear that deviations from direct data are significant (in many tens of percent) when single reference compounds are used. However, when an n-alkane that has a retention time lower than the test compound but close to it is used as the reference, the relative errors do not exceed 20%. Overall, the method has been found to be rather reliable over a wide range of conditions for nonpolar and slightly polar substances. For polar compounds, such as alcohols or nitriles, the results do confirm the need to carefully select standards with the same functionality as the targets to be evaluated. In contrast to homologous series no regular pattern can be observed for functionalized benzenes even if the reference compounds were selected from the same group of substituted benzenes.

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Section: Results and Discussionmentioning

confidence: 99%

Extracting Vapor Pressure Data from GLC Retention Times. Part 1: Analysis of Single Reference Approach

Koutek

Mahnel²,

Šimáček³

et al. 2017

J. Chem. Eng. Data

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“…To account for this effect, we assume that the Q j = f (∆) dependence, whatever its exact form, can be represented as a polynomial series. Based on our previous work concerning the alkenyl acetate series, 18 the second order terms appear to be sufficient to represent the function over the whole range of unsaturation. Consequently, we suggest the simple QSPR model given in eqns.…”

Section: Resultsmentioning

confidence: 99%

“…The vapour pressures and heats of vaporization of C 10 -C 18 alcohols, aldehydes and acetates at 25 ЊC have been taken mostly from our previous GC-based measurements [16][17][18] and completed by available literature values from other sources. It should be noted that some of our previous data for alcohols 16 have been recalculated in this work using new vapour pressure values obtained from simultaneous correlations of vapour pressure and thermal data for our GC reference compounds (12 : OH).…”

Section: Methods and Datamentioning

confidence: 99%

“…A great deal of work has been done using the GC technique by environmental chemists in determining vapour pressures of organic pollutants, 13 and also the literature vapour pressure data of pheromones available so far are based almost exclusively on the GC-based measurements. [14][15][16][17][18] As in the case of vapour pressures, there are two general groups of methods for determining the heat of vaporization. 19a The first is based on calorimetric measurements (direct methods), while the other employs calculation of ∆ vap H either from the vapour pressure vs. temperature dependence or from chromatographic data (indirect methods).…”

Section: Introductionmentioning

confidence: 99%

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Additivity of vaporization properties in pheromone-like homologous series

Koutek¹,

Hoskovec²,

Streinz³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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A simple method of estimating vaporization properties of normal alkyl and (Z)-and (E)-alkenyl homologous series of pheromone-like acetates, alcohols and aldehydes with 10 to 18 carbon atoms in the chain is described. The properties hold for the (subcooled) liquid state and include vapour pressure (p sat ) and heat of vaporization ( vap H) at 25 ЊC. An empirical QSPR model for ln p sat and vap H is developed in terms of three easy-to-calculate structural descriptors related to the number of carbon atoms in the chain (n), the functional group characteristics (I) and the double bond position ( ). The model, covering the property ranges of 2 × 10 ؊4 -2 × 10 1 Pa and 60-120 kJ mol ؊1 , explains over 99.8% of the variance in the experimental data sets containing 295 compounds, with standard errors in ln p sat and vap H of about 0.085 ln unit and 0.62 kJ mol ؊1 , respectively. It is recommended as a useful tool in designing pheromones and in fate-modelling applications in the absence of experimental data.

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“…The acetates, i.e. heptyl acetate, (E)-pent-2-enyl acetate, (E)-hept-2-enyl acetate, (E)-oct-2-enyl acetate, (E)-dec-2-enyl acetate, (E)-undec-2-enyl acetate, and (Z)-dec-3-enyl acetate, were either obtained from the Research Institute for Plant Protection (IPO-DLO, Wageningen, Netherlands) or prepared from the corresponding alcohols previously in our laboratory [33]. Authentic samples of (E)-4-oxohex-2-enal and 5-ethylfuran-2(5H)-one were synthesized according to the described procedures [34,35].…”

Section: Chemicalsmentioning

confidence: 99%

Profiling and characterization of volatile secretions from the European stink bug Graphosoma lineatum (Heteroptera: Pentatomidae) by two-dimensional gas chromatography/time-of-flight mass spectrometry

Šanda

Žáček

Streinz

et al. 2012

Journal of Chromatography B

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Gas chromatographic determination of vapour pressures of pheromone-like compounds IV. Acetates, a reinvestigation

Cited by 13 publications

References 27 publications

Extracting Vapor Pressure Data from GLC Retention Times. Part 1: Analysis of Single Reference Approach

Extracting Vapor Pressure Data from GLC Retention Times. Part 1: Analysis of Single Reference Approach

Additivity of vaporization properties in pheromone-like homologous series

Profiling and characterization of volatile secretions from the European stink bug Graphosoma lineatum (Heteroptera: Pentatomidae) by two-dimensional gas chromatography/time-of-flight mass spectrometry

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