Investigation of the Thermal Properties of Diesters from Methanol, 1-Pentanol, and 1-Decanol as Sustainable Phase Change Materials
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Characterization
2.1.1. ATR-IR
2.1.2. GC-MS
2.2. Thermal Characterization
3. Materials and Methods
3.1. Synthesis
3.2. Characterization
3.2.1. Differential Scanning Calorimetry (DSC)
3.2.2. Thermal Gravimetric Analysis (TGA)
3.2.3. Attenuated Total Reflectance Infrared Spectroscopy (ATR-IR)
3.2.4. Gas Chromatography Coupled with Mass Spectrometry (GC-MS)
4. Conclusions and Outlook
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
ATR-IR | Attenuated Total Reflectance InfraRed Spectroscopy |
DENSE | Direct contact ENergy StoragE |
DeOH | 1-Decanol (C10) |
DiDeOHOx | Didecyl Oxalate (10.2.10) |
DiDeOHSe | Didecyl Sebacate (10.10.10) |
DiDeOHSub | Didecyl Suberate (10.8.10) |
DiDeOHSu | Didecyl Succinate (10.4.10) |
DiMeOHOx | DiMethyl Oxalate (1.2.1) |
DiMeOHSe | DiMethyl Sebacate (1.10.1) |
DiMeOHSub | DiMethyl Suberate (1.8.1) |
DiMeOHSu | DiMethyl Succinate (1.4.1) |
DiPeOHOx | DiPentyl Oxalate (5.2.5) |
DiPeOHSe | DiPentyl Sebacate (5.10.5) |
DiPeOHSub | DiPentyl Suberate (5.8.5) |
DiPeOHSu | DiPentyl Succinate (5.4.5) |
DiTeOHSe | DiTetradecyl Sebacate (14.10.14) |
DSC | Differential Scanning Calorimetry |
EtOAc | Ethyl Acetate |
GC | Gas Chromatography |
GC-MS | Gas-Chromatography coupled with Mass Spectrometry |
H2SO4 | Sulfuric Acid |
IR | Infrared Spectroscopy |
IUPAC | International Union of Pure and Applied Chemistry |
LHS | Latent Heat Storage |
MeOH | Methanol (C1) |
MS | Mass spectrometry |
MSD | Mass Selective Detector |
Na2SO4 | Sodium Sulfate |
NIST | National Institute of Standards and Technology |
Ox | Oxalic acid (C2) |
PCM | Phase Change Material |
PeOH | 1-Pentanol (C5) |
PFTBA | Perfluorotributylamine |
Se | Sebacic acid (C10) |
SNSF | Swiss National Science Foundation |
Sub | Suberic acid (C8) |
Su | Succinic acid (C4) |
Tc | Crystallization Temperature |
TeOH | 1-Tetradecanol (C14) |
TES | Thermal Energy Storage |
TGA | Thermogravimetric Analysis |
Tm | Melting Temperature |
ΔH | Enthalpy of fusion |
Appendix A
Appendix B
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Compound * | Retention Time GC, min | Molecular Weight (MW), g/mol | Fragmentation Peaks MS, m/z with Relative Intensities (%) |
---|---|---|---|
DiMeOHOx (1.2.1) | 1.84 | 118 | 118 (8), 59 (100), 45 (32) |
DiPeOHOx (5.2.5) | 9.17 | 230 | 161 (1), 117 (5), 115 (8), 99 (1), 87 (3), 71 (100), 70 (55), 55(54) |
DiDeOHOx (10.2.10) | 18.27 | 370 | 281 (1), 207 (4), 191 (3), 169 (1), 164 (3), 140 (2), 133 (3), 124 (2), 112 (1), 97 (4), 85 (8), 83 (9), 71 (14), 69 (17), 57 (85), 55 (100) |
DiMeOHSu (1.4.1) | 2.73 | 146 | 116 (8), 115 (100), 114 (32), 101 (2), 87 (20), 86 (2), 60 (1), 59 (5), 57 (5), 56 (38), 55 (43) |
DiPeOHSu (5.4.5) | 12.12 | 258 | 189 (7), 171 (14), 144 (1), 119 (10), 102 (5), 101 (100), 74 (4), 71 (13), 70 (10), 69 (3), 55 (10) |
DiDeOHSu (10.4.10) | 19.71 | 398 | 259 (24), 241 (4), 207 (2), 141 (17), 119 (62), 111 (2), 101 (100), 97 (5), 85 (35), 83 (15), 71 (36), 69 (27), 57 (50), 55 (38) |
DiMeOHSub (1.8.1) | 7.94 | 202 | 171 (54), 139 (19), 138 (88), 129 (100), 114 (10), 110 (22), 101 (6), 97 (78), 87 (43), 83 (43), 74 (96), 69 (95), 67 (15), 59 (64), 55 (98) |
DiPeOHSub (5.8.5) | 15.30 | 326 | 227 (64), 200 (2), 185 (12), 157 (71), 139 (17), 138 (28), 129 (3), 115 (48), 111 (26), 97 (15), 83 (27), 70 (59), 55 (100) |
DiDeOHSub (10.8.10) | 22.43 | 454 | 327 (1), 297 (27), 281 (1), 253 (2), 209 (1), 157 (49), 140 (10), 115 (16), 111 (15), 97 (20), 83 (32), 70 (43), 69 (65), 57 (58), 56 (67), 55 (100) |
DiMeOHSe (1.10.1) | 10.30 | 230 | 200 (3), 199 (54), 170 (4), 166 (42), 157 (45), 148 (6), 139 (20), 138 (53), 125 (98), 121 (18), 111 (13), 107 (7), 101 (9), 98 (72), 97 (57), 87 (36), 84 (54), 83 (49), 79 (8), 74 (96), 73 (12), 69 (42), 67 (16), 59 (42), 55 (100) |
DiPeOHSe (5.10.5) | 17.00 | 342 | 256 (7), 255 (72), 228 (2), 213 (15), 186 (10), 185 (100), 166 (12), 143 (32), 139 (18), 125 (26), 121 (10), 98 (25), 97 (21), 83 (12), 73 (7), 70 (38), 69 (20), 60 (4), 55 (39) |
DiDeOHSe (10.10.10) | 23.88 | 483 | 325 (50), 283 (4), 253 (2), 207 (5), 186 (6), 185 (100), 166 (4), 143 (10), 139 (8), 125 (10), 111 (4), 97 (18), 83 (18), 70 (29), 69 (38), 57 (43), 55 (50) |
Structure | Carbon Number | MW (g/mol) | Tc * (Onset, °C) | Tm * (Onset, °C) | Supercooling (°C) | ΔH * (J/g) | ΔH (KJ/mol) | Tdegradation * (Start, °C) | Tdegradation * (End, °C) | |
---|---|---|---|---|---|---|---|---|---|---|
DiMeOHOx | C4H6O4 | 4 | 118 | 30.2 ± 2.3 | 46.0 ± 0.7 | 15.7 | 136.1 ± 22.0 | 16.1 | 78 ± 10 | 191 ± 18 |
DiDeOHSe | C30H58O4 | 30 | 483 | 30.1 ± 1.1 | 31.2 ± 1.1 | 1.2 | 159.6 ± 9.1 | 77.1 | 265 ± 21 | 383 ± 15 |
DiDeOHSu | C24H46O4 | 24 | 398 | 17.5 ± 1.2 | 23.8 ± 1.1 | 6.3 | 168.3 ± 26.2 | 67.0 | 228 ± 19 | 342 ± 26 |
DiMeOHSe | C12H22O4 | 12 | 230 | 5.3 ± 3.0 | 23.3 ± 1.3 | 18.0 | 158.3 ± 8.6 | 36.4 | 150 ± 1 | 263 ± 12 |
DiDeOHOx | C22H42O4 | 22 | 370 | 20.5 ± 0.7 | 23.1 ± 0.3 | 2.6 | 151.7 ± 18.8 | 56.1 | 213 ± 3 | 333 ± 3 |
DiDeOHSub | C28H54O4 | 28 | 454 | 18.2 ± 1.6 | 22.1 ± 1.5 | 3.9 | 172.3 ± 22.7 | 78.2 | 223 ± 6 | 350 ± 10 |
DiMeOHSu | C6H10O4 | 6 | 146 | −6.8 ± 6.6 | 10.1 ± 5.5 | 16.9 | 119.6 ± 8.6 | 17.5 | 85 ± 10 | 172 ± 6 |
DiPeOHSe | C20H38O4 | 20 | 342 | −3.3 ± 0.2 | 0.1 ± 0.5 | 3.4 | 155.0 ± 11.4 | 53.0 | 179 ± 10 | 287 ± 21 |
DiPeOHOx | C12H22O4 | 12 | 230 | −36.3 ± 3.0 | −16.1 ± 1.5 | 20.2 | 92.5 ± 4.9 | 21.3 | 143 ± 12 | 270 ± 20 |
DiMeOHSub | C10H18O4 | 10 | 202 | −26.0 ± 2.6 | −16.2 ± 2.3 | 9.8 | 112.2 ± 3.8 | 22.7 | 132 ± 3 | 252 ± 3 |
DiPeOHSub | C18H34O4 | 18 | 326 | −28.4 ± 2.3 | −20.3 ± 3.5 | 8.1 | 108.6 ± 23.4 | 35.4 | 182 ± 3 | 302 ± 3 |
DiPeOHSu | C14H26O4 | 14 | 258 | N.A. | N.A. | N.A. | N.A. | N.A. | 147 ± 24 | 260 ± 18 |
Structure | Carbon Number | MW (g/mol) | Tc (Onset, °C) | Tm (Onset, °C) | Supercooling (°C) | ΔH (J/g) | ΔH (KJ/mol) | Tdegradation (Start, °C) | Tdegradation (End, °C) | |
---|---|---|---|---|---|---|---|---|---|---|
DiDeOHSe | C30H58O4 | 30 | 483 | 30.1 ± 1.1 | 31.2 ± 1.1 | 1.2 | 159.6 ± 9.1 | 77.1 | 265 ± 21 | 383 ± 15 |
DiDeOHSu | C24H46O4 | 24 | 398 | 17.5 ± 1.2 | 23.8 ± 1.1 | 6.3 | 168.3 ± 26.2 | 67.0 | 228 ± 19 | 342 ± 26 |
DiDeOHSub | C28H54O4 | 28 | 454 | 18.2 ± 1.6 | 22.1 ± 1.5 | 3.9 | 172.3 ± 22.7 | 78.2 | 223 ± 6 | 350 ± 10 |
DiDeOHOx | C22H42O4 | 22 | 370 | 20.5 ± 0.7 | 23.1 ± 0.3 | 2.6 | 151.7 ± 18.8 | 56.1 | 213 ± 3 | 333 ± 3 |
DiPeOHSub | C18H34O4 | 18 | 326 | −28.4 ± 2.3 | −20.3 ± 3.5 | 8.1 | 108.6 ± 23.4 | 35.4 | 182 ± 3 | 302 ± 3 |
DiPeOHSe | C20H38O4 | 20 | 342 | −3.3 ± 0.2 | 0.1 ± 0.5 | 3.4 | 155.0 ± 11.4 | 53.0 | 179 ± 10 | 287 ± 21 |
DiPeOHOx | C12H22O4 | 12 | 230 | −36.3 ± 3.0 | −16.1 ± 1.5 | 20.2 | 92.5 ± 4.9 | 21.3 | 143 ± 12 | 270 ± 20 |
DiMeOHSe | C12H22O4 | 12 | 230 | 5.3 ± 3.0 | 23.3 ± 1.3 | 18.0 | 158.3 ± 8.6 | 36.4 | 150 ± 1 | 263 ± 12 |
DiPeOHSu | C14H26O4 | 14 | 258 | N.A. | N.A. | N.A. | N.A. | N.A. | 147 ± 24 | 260 ± 18 |
DiMeOHSub | C10H18O4 | 10 | 202 | −26.0 ± 2.6 | −16.2 ± 2.3 | 9.8 | 112.2 ± 3.8 | 22.7 | 132 ± 3 | 252 ± 3 |
DiMeOHOx | C4H6O4 | 4 | 118 | 30.2 ± 2.3 | 46.0 ± 0.7 | 15.7 | 136.1 ± 22.0 | 16.1 | 78 ± 10 | 191 ± 18 |
DiMeOHSu | C6H10O4 | 6 | 146 | −6.8 ± 6.6 | 10.1 ± 5.5 | 16.9 | 119.6 ± 8.6 | 17.5 | 85 ± 10 | 172 ± 6 |
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Ravotti, R.; Fellmann, O.; Fischer, L.J.; Worlitschek, J.; Stamatiou, A. Investigation of the Thermal Properties of Diesters from Methanol, 1-Pentanol, and 1-Decanol as Sustainable Phase Change Materials. Materials 2020, 13, 810. https://doi.org/10.3390/ma13040810
Ravotti R, Fellmann O, Fischer LJ, Worlitschek J, Stamatiou A. Investigation of the Thermal Properties of Diesters from Methanol, 1-Pentanol, and 1-Decanol as Sustainable Phase Change Materials. Materials. 2020; 13(4):810. https://doi.org/10.3390/ma13040810
Chicago/Turabian StyleRavotti, Rebecca, Oliver Fellmann, Ludger J. Fischer, Jörg Worlitschek, and Anastasia Stamatiou. 2020. "Investigation of the Thermal Properties of Diesters from Methanol, 1-Pentanol, and 1-Decanol as Sustainable Phase Change Materials" Materials 13, no. 4: 810. https://doi.org/10.3390/ma13040810