Insight into the role of piperazine in the thermodynamics and nucleation kinetics of the triethylenediamine–methyl tertiary butyl ether system

Quan, Yufeng; Yang, Yang; Xu, Shijie; Zhu, Peipei; Liu, Shiyuan; Jia, Lina; Gong, Junbo

doi:10.1039/c8ce01179f

Cited by 23 publications

(24 citation statements)

References 34 publications

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“…To simplify the complicated units of nucleation constant in Nývlt's equation, Sangwal derived a self‐consistent Nývlt‐like equation [ 9 ] by defining nucleation rate as a power‐law function of supersaturation ratio. Combined with the regular solution theory, it can be described as followed

\begin{matrix} true \\ right \ln ((), \frac{Δ T_{normalmax}}{T_{0}}) & = & left \frac{1 - m}{m} \ln ((), \frac{Δ H_{normald}}{R_{normalG} T_{normallim}}) + \frac{1}{m} \ln ((), \frac{f}{K}) \\ left - \frac{1}{m} normalln T_{0} + \frac{1}{m} normalln R \end{matrix}

…”

Section: Methodsmentioning

confidence: 99%

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Effect of Sodium Sulfate on Nucleation Behavior and the Crystal Morphology of Taurine

Zhang

Luo

et al. 2020

Crystal Research and Technology

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Two theoretical methods, self‐consistent Nývlt‐like approach and Sangwal's classical 3D nucleation theory‐based method, are employed to analyze the effects of additives (sodium sulfate) on the nucleation behavior of taurine. By correlating the measured metastable zone width of taurine containing different sodium sulfate concentrations, with saturation temperature and cooling rate, nucleation kinetic parameters in both two methods are determined. Fitting results demonstrate that higher sodium sulfate concentration results in the increase of solid–liquid interfacial energy γ, contrarily higher saturation temperature has the opposite effect thus changing of nucleation rate. The molecular modeling techniques are then applied to investigate the changes in the morphology of taurine which caused by the presence of sodium sulfate. Through molecular dynamic simulations, the interaction energy of sodium sulfate with taurine crystal faces are obviously larger than those of taurine and these differences on the (011) and (11‐1) are more significant than those on (021) and (111) faces. As a result, the growth of (011) and (11‐1) faces is inhibited and the morphology of taurine crystal is modified from needle to columnar. The influence of sodium sulfate on taurine studied in this work provides theoretical guidance for industrial production.

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\begin{matrix} true \\ right \ln ((), \frac{Δ T_{normalmax}}{T_{0}}) & = & left \frac{1 - m}{m} \ln ((), \frac{Δ H_{normald}}{R_{normalG} T_{normallim}}) + \frac{1}{m} \ln ((), \frac{f}{K}) \\ left - \frac{1}{m} normalln T_{0} + \frac{1}{m} normalln R \end{matrix}

…”

Section: Methodsmentioning

confidence: 99%

“…To get further study on crystallization nucleation behavior, several models [ 8,9 ] have been reported for the determination and theoretical prediction of the MSZW of different systems. Nývlt [ 10 ] proposed a method which is based on the assumption of the linear relationship between MSZW and cooling rate.…”

Section: Introductionmentioning

confidence: 99%

Effect of Sodium Sulfate on Nucleation Behavior and the Crystal Morphology of Taurine

Zhang

Luo

et al. 2020

Crystal Research and Technology

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“…The amorphous cells were subjected to geometry and dynamics simulation using Dreiding force field [27]. In dynamics simulation, an NVT (fixed number of particles, volume, and temperature) ensemble method was selected at a temperature of 298.15 K. The time step was 1.0 fs with a total simulation time of 500 ps, controlled by Andersen thermostat [28]. Then, the RDF was computed using the O atom of DMSO and the N atom of -NH 2 from Tautomer A or the N atom of =NH from Tautomer B.…”

Section: Molecular Dynamics Simulationmentioning

confidence: 99%

“…On the basis of the result of ESP analysis, the O atom of DMSO and the N atom of -NH 2 from Tautomer A or the N atom of =NH from Tautomer B were chosen for RDF analysis (Fig. 6), which can be used to evaluate the interaction strength in solution [28]. In RDF results, chemical bonds or hydrogen bonds usually contribute to a sharp peak within 3.5 Å, while van der Waals interactions contribute to a peak between 3.5 and 5.0 Å [38].…”

Section: Rdf Analysismentioning

confidence: 99%

The Role of Solvent in Tautomer Solvate Crystallization: A Case of 6-Amino-1,3-Dimethyl-5-Nitrosouracil

Jin²,

et al. 2020

Trans. Tianjin Univ.

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Tautomers are structural isomers that readily interconvert and may exhibit different properties. The effect of solvent on tautomeric equilibria in solution has been a subject of some research. Tautomer solvate is less common, and the role of solvent in the crystallization of tautomer solvate remains an interesting topic. In this work, we used 6-amino-1,3-dimethyl-5-nitrosouracil (NAU) as the tautomeric model material, which can present in nitrone-enamine form (Tautomer A) or oxime-imine form (Tautomer B). A solvate with NAU/DMSO ratio of 1:1 was discovered and characterized using single/ powder X-ray diffraction and thermogravimetry. The crystal structure of NAU•DMSO was determined for the first time, where only Tautomer A was formed in the tautomeric crystal. Quantum chemical calculation and molecular dynamics simulation were conducted to determine the tautomeric form in DMSO solution. Electrostatic potential analysis, radial distribution function analysis, and binding energy suggested possible DMSO-NAU interaction modes and stable tautomer complexes in solution. Tautomer A-containing complexes were found to dominate in solution, as verified by comparing predicted and experimental 1 H NMR spectra. Findings reveal that the hydrogen bonding between DMSO and NAU is similar in solution and in NAU-DMSO solvate crystal, which helps preserve the form of Tautomer A during solvate crystallization.

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“…36 It has higher nucleophilic reaction activity than the primary amine, which makes it easier to react with isocyanate and the produced urea is thus more stable. At the same time, the amino groups of piperazine are located on the six-membered ring, 37 which bear a high steric hindrance. Therefore, the reaction between piperazines and isocyanate may have high binding constants as well as high counter reaction speed constants.…”

Section: Introductionmentioning

confidence: 99%

Reducing the reprocessing and healing temperature of polyurea with piperazine-based hindered urea bonds

Wang

Gao

et al. 2022

Mater. Chem. Front.

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Insight into the role of piperazine in the thermodynamics and nucleation kinetics of the triethylenediamine–methyl tertiary butyl ether system

Abstract: Considering the role of piperazine in the TEDA–MTBE system, we investigate how to control the crystal size distribution.

Cited by 23 publications

References 34 publications

Effect of Sodium Sulfate on Nucleation Behavior and the Crystal Morphology of Taurine

Effect of Sodium Sulfate on Nucleation Behavior and the Crystal Morphology of Taurine

The Role of Solvent in Tautomer Solvate Crystallization: A Case of 6-Amino-1,3-Dimethyl-5-Nitrosouracil

Reducing the reprocessing and healing temperature of polyurea with piperazine-based hindered urea bonds

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