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Molecules 2020, 25, 5572 10 of 26 whether it emerges for β’ and α polymorphs. Altough the odd-even alternation for enthalpies of fusion is not mentioned by Malkin [24] and Lutton [15], it has been observed by Ravotti et al. [44] in the case of saturated fatty esters. The specific causes behind this behaviour are not clear, but it could potentially be due to the lower degree of symmetry present in odd-numbered molecules. Nevertheless, the presence of missing or incomplete data in the case of enthalpies of fusion makes it difficult to draw general conclusions on possible trends 3.2. Unsaturated Symmetrical Triglycerides (UST) Table 2 summarizes the data collected for the peak melting temperatures of UST. The UST are abbreviated in a similar way to SST, but with additional information on the number and location of the unsaturation. For example, trilinolein is derived from glycerol and three linoleic acid molecules, whose carbon number is 18 and that have 2 double bonds in the cis configuration at the carbon numbers 9 and 12. Therefore, trilinolein is indicated as 18.18.18:2 cis 9-12 (Figure 10). Figure 10. Chemical structure of trilinolein. Since trilinolein presents 2 cis double bonds at position 9 and 12 of each alkyl chain, tristearin is abbreviated as 18.18.18:2 9-12. The studies conducted on unsaturated triglycerides are far less extensive than they are for saturated triglycerides. Several data are still missing, especially with regard to the enthalpies of fusion. Most data collected concerns the main constituents of olive oil and vegetable oils in general, such as triolein and trilinolein. Additionally, no data could be found for most of the odd-numbered UST. Although it is difficult to draw conclusions given the lack of data, some broad observations can be made. In general, compared to SST of equal chain length, UST show lower melting points and enthalpies of fusion. Similarly to what was observed for SST, the highest phase change enthalpy seems to arise for the 18 carbon-numbered compound, tripetroselaidin (18.18.18:1 trans 6), with 179.9 J/g. The reasons behind the lower enthalpy of fusion are unclear, but could be due to an easier disruption of the crystal lattice caused by the presence of unsaturated bonds brought on by a lower degree of symmetry. While UST with double bonds in the trans configuration still present similar characteristics to SST with melting temperatures above 0 ◦C and enthalpies of fusion ≥150 J/g, most of the UST in the cis configuration show the opposite behaviour with melting temperatures below 0 ◦C and enthalpies of fusion ≤150 J/g. Such difference becomes more marked in the presence of increasing number of double bonds in the cis configuration. This is due to the bend that the aliphatic chain undergoes in the presence of cis-double bonds as shown in Figure 11a–d, which contributes in generating wider long spacings and lowering the overall symmetry and crystal packing compactness [23,24].PDF Image | Triglycerides as Novel Phase-Change Materials
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