Activity Coefficients for Liquid Organic Reactions: Towards a Better Understanding of True Kinetics with the Synthesis of Jasmin Aldehyde as Showcase
Abstract
:1. Introduction
2. Results and Discussion
3. Methods
3.1. Reaction Mechanism
3.2. In-Silico Data and Parameter Estimation Procedure
4. Conclusions
Supplementary Materials
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
B | benzaldehyde |
CE | continuity equation |
DMF | dimethylformamide |
E1, E2 | end product 1 and 2 (jasmin aldehyde and (Z)-2-pentylnon-2-enal) |
GC-MS | gas chromatography mass spectrometry |
H | heptanal |
HPLC | high pressure liquid chromatography |
NC | number of components |
ODR | orthogonal distance regression |
RSSQ | residual sum of squares |
S | selectivity (mol·mol−1) |
t | reaction time (dep.) |
T | temperature (°C) |
UNIFAC | UNIQUAC (universal quasichemical) functional-group activity coefficients |
W | water |
X | conversion (mol·mol−1) |
* | ‘A*B’ signifies the product of the activity coefficients for compound A and B |
Appendix A
Entry | Conditions | Catalyst | X (%) | S (%) | Ref. |
---|---|---|---|---|---|
1 | B (15.8 mmol), H (7.9 mmol), t = 1 h, T = 125 °C | L-proline (40 mol%) + benzoic acid | 99 | 96 | [14] |
2 | p-chlorobenzaldehyde (0.5 mmol), isobutyraldehyde (dep.), Cs2O3 as base (10 mol%), solvent THF or xylene (5 mL) | N-heterocyclic carbene catalyst (10 mol%) | (1) | (1) | [15] |
3 | aliphatic and aromatic aldehydes (1) | Ti(OR)4 | (1) | (1) | [16] |
4 | B (7–79 mmol), H (2–31.6 mmol), tmax = 6 h, T = 100–180 °C | modified chitosan | (2) | (2) | [12] |
5 | n-heptanal (2.28 g) dropwise (during 30 min) in benzaldehyde (2.12 g), t = 3 h | K2CO3 (2.76 g) and benzyltriethylammonium chloride as phase transfer catalyst (2.5 g) in CH2Cl2 | (3) | 80 | [17] |
6 | B (336 mmol), H (33.6 mmol), t = 2 h, T = 150 °C | Al-MCM-41 supported MgO (0.2 g) | 9.4–96.7 | 40.7–56.2 | [44] |
7 | B and H(4), t = 15 min, T = 120 °C | pyrrolidine (30 mol%) | (3) | 93 | [45] |
8 | (B/H)0 = 2/1, T = 120 °C, solvent = DMF | MgO | 94 | 68 | [46] |
9 | benzaldehyde with C3–C8 linear aldehydes | K2CO3/Al2O3, KOH/Al2O3 | (1) | (1) | [47] |
10 | (B/H)0 = 2/1, T = 80–140 °C, t < 7 h | Zn modified mixed Mg/Al Oxides | (1) | (1) | [48] |
11 | (B/H)0 = 2/1, T = 100 °C, no solvent | industrially prepared Mg–Al mixed oxides | <70 | <66 | [49] |
Appendix B
References
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(B/H)0 | T (In °C) | B*H | H*H | E1*W | E2*W |
---|---|---|---|---|---|
2 | 80 | 2.752 ± 0.048 | 1.900 ± 0.022 | 8.251 ± 0.107 | 9.947 ± 0.049 |
100 | 2.740 ± 0.045 | 1.903 ± 0.022 | 7.996 ± 0.104 | 9.537 ± 0.048 | |
120 | 2.680 ± 0.042 | 1.885 ± 0.021 | 7.726 ± 0.098 | 9.182 ± 0.048 | |
140 | 2.603 ± 0.039 | 1.856 ± 0.021 | 7.450 ± 0.093 | 8.836 ± 0.047 | |
1 | 80 | 2.722 ± 0.069 | 1.763 ± 0.036 | 8.101 ± 0.152 | 9.155 ± 0.050 |
100 | 2.720 ± 0.064 | 1.774 ± 0.035 | 7.850 ± 0.148 | 8.788 ± 0.048 | |
120 | 2.649 ± 0.058 | 1.756 ± 0.033 | 7.574 ± 0.140 | 8.479 ± 0.048 | |
140 | 2.556 ± 0.054 | 1.725 ± 0.032 | 7.295 ± 0.132 | 8.185 ± 0.048 | |
0.5 | 80 | 2.676 ± 0.080 | 1.669 ± 0.045 | 8.097 ± 0.180 | 8.811 ± 0.051 |
100 | 2.683 ± 0.074 | 1.686 ± 0.043 | 7.838 ± 0.177 | 8.451 ± 0.050 | |
120 | 2.610 ± 0.067 | 1.669 ± 0.040 | 7.553 ± 0.168 | 8.155 ± 0.049 | |
140 | 2.515 ± 0.062 | 1.646 ± 0.041 | 7.267 ± 0.155 | 7.910 ± 0.049 |
Parameter | Unit | Without Correction | With Correction |
---|---|---|---|
k1,∞ | M−1·s−1 | (1.36 ± 0.01) × 104 (1.70) | (7.62 ± 0.12) × 103 (1.05) |
E1 | kJ·mol−1 | 40.8 ± 0.6 | 40.0 ± 0.9 |
k2,∞ | s−1 | (4.36 ± 0.16) × 107 (31.4) | (4.71 ± 0.10) × 106 (3.39) |
E2 | kJ·mol−1 | 66.4 ± 2.4 | 64.2 ± 1.4 |
k3,∞ | M−1·s−1 | (2.89 ± 0.02) × 104 (1.25) | (2.84 ± 0.03) × 104 (1.27) |
E3 | kJ·mol−1 | 46.8 ± 0.5 | 47.3 ± 0.6 |
k4,∞ | s−1 | (4.44 ± 0.26) × 106 (3.13) | (4.91 ± 0.23) × 106 (2.85) |
E4 | kJ·mol−1 | 60.1 ± 4.4 | 65.9 ± 3.5 |
RSSQ | μM2 | 0.470 | 0.342 |
Parameter | Unit | Without Correction | With Correction |
---|---|---|---|
k1,∞ | M−1·s−1 | (1.69 ± 0.01) × 104 (2.11) | (1.01 ± 0.01) × 104 (1.26) |
E1 | kJ·mol−1 | 39.6 ± 0.3 | 41.0 ± 0.5 |
k2,∞ | s−1 | (1.32 ± 0.02) × 107 (9.54) | (3.82 ± 0.04) × 106 (2.75) |
E2 | kJ·mol−1 | 61.2 ± 0.8 | 63.8 ± 0.7 |
k3,∞ | M−1·s−1 | (8.31 ± 0.11) × 104 (2.30) | (5.35 ± 0.09) × 104 (1.48) |
E3 | kJ·mol−1 | 49.1 ± 0.8 | 49.4 ± 1.1 |
k4,∞ | s−1 | (1.32 ± 0.04) × 108 (9.52) | (4.06 ± 0.12) × 107 (2.92) |
E4 | kJ·mol−1 | 70.8 ± 2.8 | 73.9 ± 2.5 |
RSSQ | μM2 | 0.298 | 0.287 |
Parameter | Unit | Without Correction | With Correction |
---|---|---|---|
k1,∞ | M−1·s−1 | (1.87 ± 0.04) × 104 (2.34) | (1.14 ± 0.03) × 104 (1.42) |
E1 | kJ·mol−1 | 40.0 ± 1.1 | 41.4 ± 1.5 |
k2,∞ | S−1 | (1.31 ± 0.01) × 107 (9.44) | (3.48 ± 0.04) × 106 (2.51) |
E2 | kJ·mol−1 | 61.1 ± 0.6 | 63.5 ± 0.8 |
k3,∞ | M−1·s−1 | (8.72 ± 0.14) × 104 (2.41) | (5.94 ± 0.07) × 104 (1.65) |
E3 | kJ·mol-1 | 49.6 ± 1.0 | 49.8 ± 0.7 |
k4,∞ | s−1 | (7.27 ± 0.19) × 107 (5.24) | (1.39 ± 0.05) × 107 (1.00) |
E4 | kJ·mol−1 | 69.0 ± 2.1 | 70.5 ± 2.7 |
RSSQ | μM2 | 0.276 | 0.265 |
Parameter | Unit | Without Correction | With Correction |
---|---|---|---|
k1,∞ | M−1·s−1 | (1.98 ± 0.03) × 104 (2.48) | (8.98 ± 0.27) × 103 (1.12) |
E1 | kJ·mol−1 | 40.3 ± 0.7 | 40.5 ± 1.6 |
k2,∞ | s−1 | (2.72 ± 0.03) × 107 (19.6) | (3.79 ± 0.02) × 106 (2.73) |
E2 | kJ·mol−1 | 63.3 ± 0.7 | 63.6 ± 0.3 |
k3,∞ | M−1 s−1 | (3.69 ± 0.07) × 104 (1.02) | (2.56 ± 0.06) × 104 (1.41) |
E3 | kJ·mol−1 | 47.0 ± 1.0 | 49.8 ± 0.7 |
k4,∞ | s−1 | (4.06 ± 0.03) × 106 (3.43) | (1.24 ± 0.03) × 107 (1.12) |
E4 | kJ·mol−1 | 59.4 ± 6.2 | 70.0 ± 2.0 |
RSSQ | μM2 | 0.201 | 0.197 |
Kinetic Coefficient | Unit | Reported Range | Ballpark Value |
---|---|---|---|
k1,∞ | M−1·s−1 | 8.2 × 103 [31] | 8.0 × 103 |
E1 | kJ·mol−1 | 20–40 [32], 48.5 [31], 39.7–49.9 [33] | 40 |
k2,∞ | s−1 | 1.4 × 106 | |
E2 | kJ·mol−1 | 60 | |
k3,∞ | M−1·s−1 | 1.35 × 103–1.0 × 106 [34] | 3.6 × 104 |
E3 | kJ·mol−1 | 42.7–53.8 [34] | 48 |
k4,∞ | s−1 | 1.4 × 107 | |
E4 | kJ·mol−1 | 70 |
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Heynderickx, P.M. Activity Coefficients for Liquid Organic Reactions: Towards a Better Understanding of True Kinetics with the Synthesis of Jasmin Aldehyde as Showcase. Int. J. Mol. Sci. 2019, 20, 3819. https://doi.org/10.3390/ijms20153819
Heynderickx PM. Activity Coefficients for Liquid Organic Reactions: Towards a Better Understanding of True Kinetics with the Synthesis of Jasmin Aldehyde as Showcase. International Journal of Molecular Sciences. 2019; 20(15):3819. https://doi.org/10.3390/ijms20153819
Chicago/Turabian StyleHeynderickx, Philippe M. 2019. "Activity Coefficients for Liquid Organic Reactions: Towards a Better Understanding of True Kinetics with the Synthesis of Jasmin Aldehyde as Showcase" International Journal of Molecular Sciences 20, no. 15: 3819. https://doi.org/10.3390/ijms20153819