Vapor pressure and thermophysical properties of eugenol and (+)-carvone

Abstract

In this work, vapor pressures, liquid-phase heat capacities, and phase behavior of two monoterpenoids, (þ)-carvone and eugenol were studied. The vapor pressure experiments were performed using a static method over an environmentally relevant range of temperatures, from 258 K to 308 K. Liquid-phase heat capacities were measured by Tian-Calvet calorimetry between 265 K and 355 K. The phase behavior was investigated by heat-flux differential scanning calorimetry from 183 K. Experimental data were supplemented by ideal-gas thermodynamic properties obtained by combining quantum chemical and statistical thermodynamic calculations. Vapor pressures and heat capacities obtained in this work along with selected literature values were treated simultaneously by multi-property correlation in order to obtain a consistent description of thermodynamically linked properties. To our knowledge, liquid-phase heat capacities and phase behavior of eugenol are reported for the first time in this work.

Calculation of the Isobaric Heat Capacities of the Liquid and Solid Phase of Organic Compounds at 298.15K by Means of the Group-Additivity Method

“…In addition, further C p values have been found for the amines hexamethylenetetramine [15], tetra-N-phenylbenzidine and 4,4 -bis (N-carbazolyl)-1,1 -biphenyl [16], 1,3,5-triazine [17], the ethers 1,3,5-trioxane [17], diethylene glycol n-pentyl ether [18], triethylene glycol monopentyl ether [19] and diphenyl ether [20], several alcohols and aldehydes [21], derivatives of glycidol [22], carboxylic acids [23,24], aliphatic esters [24][25][26][27], benzoates [28], haloalkanes [29,30], haloaromatics [31,32], thio ethers, sulfones and sulfoxides [33,34], alkanolamines, [35][36][37] and nitriles [38] For several compounds, more recent publications have been found the following: 4-ethylmorpholine [39], methionine [40], theophylline, and caffeine [41], as well as for (-)-menthone, (+)-pulegone, and (-)-isopulegol [42]. Beyond these, experimental C p values of a number of new compounds have been published: namely 3-amino-4-amidoximinofurazan [43], 3-fluoro-5-(3-pyridinyloxy)-benzenamine and N- [46], eugenol and (+)-carvone [47], indapamide [48], and the explosives EDNH and DNTA [49]. For some silicon-containing compounds, new C p data have been found in [50].…”

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

“…Another idea, which could also provide interesting new perspectives, was to open the seven-membered ring up to allow some flexibility to the double-bonded oxygen (Figure 5) in order to find the key interaction, since, in the benzodioxepinone series, the geometry of the seven-membered ring imposes the spatial orientation of the carbonyl group [199,203,208]. Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209]. Another alternative to preserve the marine-ozone character of the compounds was to reduce the ring size from seven to five atoms.…”

“…More recently, in 2018, two derivatives with isobutyl (13) and isopentyl ( 14) hyrophobic radical groups were discovered (Table 2) and have showed particularly interesting marine olfaction properties. Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209]. Therefore, the analogs of bendioxepinone (6), calcone (7) and aldolone (8) (Figure 6) exhibit an olfactory profile of: "green cresolic", "spicy, isoeugenol, guaiacol, vanillic" and "perspiration, aldehydic, slightly aldehyde muguet, vanillic, slightly metallic, nice, too weak", respectively [209].…”

“…It is measured by diverse methods and is expressed as mmHg, and could be calculated by different equation models. A compilation of studies of the vapor pressure of odoriferous compounds has been reported by innumerable studies including terpenes, which are the largest group of natural smell compounds found in essential oils, among others [6][7][8]. The fragrant compounds are detected, via a complex olfaction mechanism, by terrestrial organisms when transported by air from a distance through an airborne signaling process,…”

Calculation of the Isobaric Heat Capacities of the Liquid and Solid Phase of Organic Compounds at 298.15K by Means of a Generally Applicable Computer Algorithm Based on the Group-Additivity Method

“…For several compounds, more recent publications have been found: in particular for 4-ethylmorpholine [38], methionine [39], theophylline and caffeine [40], as well as for (-)-menthone, (+)-pulegone and (-)-isopulegol [41]. Beyond these, experimental Cp values of a number of new compounds have been published: namely 3-amino-4-amidoximinofurazan [42] [45], eugenol and (+)-carvone [46], indapamide [47] and the explosives EDNH and DNTA [48]. For some silicon compounds, new Cp data have been found in [49].…”