Thermodynamic Properties of Biogenic Amines and Their Solutions

Abstract

Vapor pressures of the biologically and industrially relevant amines 2-phenylethan-1-amine, 2-amino-1-phenylethanol, α-(methylaminomethyl)benzyl alcohol, 1-phenylmethanamine, and N,N-diethylundecan-1-amine were measured via the transpiration method. Pure-component parameters for the thermodynamic model PC-SAFT were fitted to these vapor pressures and to liquid densities. The pure-component parameters were validated with measured liquid densities of binary mixtures dimethylsulfoxid + 4-(2-aminoethyl)phenol, dimethylsulfoxid + 2-amino-1-phenylethanol, dimethylsulfoxid + α-(methylaminomethyl)benzyl alcohol, and dimethylsulfoxid + 1-phenylmethanamine at 0.102 MPa and temperatures from 298.15 to 343.15 K at different amine mass fractions. Solid−liquid equilibria at 0.1 MPa were measured in binary mixtures of α-(methylaminomethyl)benzyl alcohol + water and 4-(2-aminoethyl)phenol + water at 298.15 and 308.15 K. Finally, the presence of liquid−liquid phase separation for these systems was qualitatively predicted using PC-SAFT based on the solid−liquid equilibria only and validated for the system α-(methylaminomethyl)benzyl alcohol + water by experiments at 293.15 and 323 K at 0.1 MPa.

Application of CP-PC-SAFT and PC-SAFT for Simultaneous Prediction of LLE and High-Pressure VLE with Universal k12 Values in Systems of Gases and n-Alkanes with N-Methyl-2-pyrrolidone and Some Substituted Aromatic Compounds

“…For example, the only available set of parameters for 2-methoxyphenol overestimates UCSTs in its systems of n -dodecane and n -hexadecane but underrates the VLE phase split of the system of methane (Figure S3). Moreover, with the association-considering parameter sets for 2-phenylethanol (Figure S2A), aniline , (Figure S2C), benzylamine (Figure S2E), and phenol − (Figure S2F), the model fails in reproducing the dependencies of UCSTs on the n -alkane carbon numbers. Unsurprisingly, the results of these approaches for the high-pressure VLE in the systems of gases are particularly poor as well (Figures S6 and S10).…”

“…In addition to NMP, van Niekerk et al and Razavi et al proposed parameters for pyridine. Besides that, the PC-SAFT parameters were reported by other studies for the previously considered compounds, namely 2-methoxyphenol, 2-phenylethanol, − acetophenone, aniline, ,, benzaldehyde, − benzylamine, and phenol. − These sets along with the parameters of CP-PC-SAFT are listed in Table S1 of the Supporting Information. All of the calculations performed in Mathematica software and the relevant routines can be obtained from the corresponding author by request.…”

“…Moreover, with the association-considering parameter sets for 2-phenylethanol 49 (Figure S2A), aniline 29,52 (Figure S2C), benzylamine 57 (Figure S2E), and phenol 58−60 (Figure S2F), the model fails in reproducing the dependencies of UCSTs on the n-alkane carbon numbers. Unsurprisingly, the results of these approaches for the high-pressure VLE in the systems of gases are particularly poor as well (Figures S6 and S10).…”

Renewable Platform Chemicals: Evaluation of Experimental Data for Alkyl Benzoates with Complementary Measurements, Structure–Property Correlations, and Quantum Chemical Calculations

“…This contribution is part of a Special Issue in honor of Prof. Dr. Gabriele Sadowski. In the past, there have already been numerous collaborations with her working group. , This current paper has the main task of drawing the attention of Prof. Sadowski to transfer hydrogenation in the great hope of achieving cooperation in this promising field.…”

Predicting Solvent Effects on Homogeneity and Kinetics of the Hydroaminomethylation: A Thermodynamic Approach Using PC-SAFT

“…All reactions were investigated in a TMS of methanol and n-dodecane (DDC), which in recently published works 14−18 was found to be a promising solvent system. The pure-component PC-SAFT parameters and the binary interactions between all components involved in the HAM as well as between these and the solvents were investigated in detail in earlier works, 19,20 providing an almost complete set of PC-SAFT parameters. In this work, the LLE of the multicomponent reaction system is predicted using PC-SAFT.…”