Construction and evaluation of ternary solid-liquid phase diagram of pyraclostrobin (form IV) and its intermediate in ethanol and N,N-dimethylformamide

Du, Cunbin; Dong, Ruimei; Qiao, Bin; Jin, Zhudan; Ye, Tingting; Zhang, Ying; Wang, Mingliang

doi:10.1016/j.jct.2018.07.025

Cited by 8 publications

(3 citation statements)

References 15 publications

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“…The binary equilibrium system was determined by the isothermal saturation method , in the temperature ranging from 278.15 to 318.15 K, and the ternary and quaternary solid–liquid phase equilibrium were determined , at 298.15, 308.15, and 318.15 K. All experiments were performed at atmospheric pressure ( p = 101.3 kPa). The concentrations of uric acid, adenine, and guanine in a binary, ternary, or quaternary phase equilibrium system were analyzed by HPLC.…”

Section: Methodsmentioning

confidence: 99%

Determination, Construction, and Evaluation of Ternary and Quaternary Solid–Liquid Phase Equilibrium of Uric Acid, Adenine, and Guanine in Water

Cong

Wang

et al. 2020

J. Chem. Eng. Data

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In this work, nine ternary phase diagrams and three quaternary phase diagrams of different systems at 298.15, 308.15, and 318.15 K were constructed. The ternary solid–liquid phase equilibrium of (uric acid + adenine + water), (uric acid + guanine + water), and (adenine + guanine + water) and quaternary solid–liquid phase equilibrium of (uric acid + adenine + guanine + water) were determined at atmospheric pressure (p = 101.3 kPa). The binary solubility of uric acid, adenine, and guanine in water at different temperatures was determined and correlated using the modified Apelblat model, and the mole solubility of adenine was about 30 and 180 times that of uric acid and guanine, respectively. The relative average deviation and root-mean-square deviation values were no more than 1.73 × 10–2 and 0.102 × 10–5, respectively. For a ternary system, each phase diagram consisted of one cosaturated point, two cosaturated solubility curves, and three solid-phase regions (two single solid-phase regions and one double solid-phase region). The mutual solubility of uric acid (adenine or guanine) in the systems of (uric acid + adenine + water), (uric acid + guanine + water), or (adenine + guanine + water) increased with increasing temperature. The unsaturated regions enlarged, and the single or double solid-phase regions diminished. For a quaternary system, each Janeck projection of the (uric acid + adenine + guanine + water) system consisted of one cosaturated point, three cosaturated solubility curves, and three solid-phase regions. At the same temperature, the solid-phase regions of three compounds were ranked as guanine > uric acid > adenine. The construction of binary, ternary, and quaternary phase diagrams of uric acid, adenine, and guanine in water was of great significance for studying the deposition of uric acid, and this can also provide reference and basic phase equilibrium data for further study of gout treatment and effects of uric acid on the cardiovascular system.

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Section: Methodsmentioning

confidence: 99%

Determination, Construction, and Evaluation of Ternary and Quaternary Solid–Liquid Phase Equilibrium of Uric Acid, Adenine, and Guanine in Water

Cong

Wang

et al. 2020

J. Chem. Eng. Data

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“…Pyraclostrobin, also known as methyl-{2-[1-(4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]phenyl}, manifests a bright promise in agriculture with the characteristics of abroad spectrum, high efficiency, low toxicity, non-target biosafety, and friendliness to users and the environment due to its ability to inhibit mitochondrial respiration in a novel mode of action. [1][2][3] 1-(4-chlorophenyl)-3-pyrazolol is an essential intermediate for the preparation of pyraclostrobin. 4,5 1-(4-chlorophenyl)-3-pyrazolol is usually made from the oxidation of 1-(4-chlorophenyl)pyrazolidan-3-one.…”

Section: Introductionmentioning

confidence: 99%

A study on the oxidation of 1‐(4‐chlorophenyl) pyrazolidin‐3‐one to 1‐(4‐chlorophenyl)‐3‐pyrazolol by oxygen

Zhu,

Jiang,

Song

et al. 2023

J of Chemical Tech & Biotech

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BACKGROUNDPyraclostrobin manifests a bright promise in agriculture with the characteristics of a broad spectrum, high efficiency, low toxicity, non‐target biosafety, and friendliness to users and the environment due to its ability to inhibit mitochondrial respiration in a novel mode of action. 1‐(4‐chlorophenyl)‐3‐pyrazolol is an essential intermediate for the preparation of pyraclostrobin. The commercial technology for the production of 1‐(4‐chlorophenyl)‐3‐pyrazolol by oxidizing 1‐(4‐chlorophenyl)pyrazolidan‐3‐one with H2O2 in strong an alkali solution is risky and not friendly to the environment.RESULTSA solid Fe/AC catalyst is constructed by loading ferric on commercial activated carbon. The activated carbon and ferric act cooperatively to upgrade the oxidation rate of 1‐(4‐chlorophenyl)pyrazolidan‐3‐one and the yield of 1‐(4‐chlorophenyl)‐3‐pyrazolol with air. The best catalyst is Fe/AC supported with 15% Fe2O3 on activated carbon of 100 ~ 120 mesh without activation.CONCLUSIONThe Fe/AC catalyst is able to not only accelerate the oxidation of 1‐(4‐chlorophenyl) pyrazolidin‐3‐one but also obtain a higher yield of 1‐(4‐chlorophenyl)‐3‐pyrazolol than FeCl3 or activated carbon can in 5%(wt.) NaOH solution. The highest 1‐(4‐chlorophenyl)‐3‐pyrazolol yield is obtained by a gas stream containing 60%(wt.) oxygen with a Fe/AC dosage of 1.25 g L−1. © 2023 Society of Chemical Industry.

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“…Compared with other preparation methods, the dry heat method has no other solvent in the reaction process and belongs to a green synthesis process. After the reaction is complete, the target product is dissolved in distilled water, filtered, and crystallized successively . Nevertheless, due to the large solubility of l -pyroglutamic acid in the water, there is much loss in the process of using this separation method, and the crystallization method cannot completely separate l -glutamic acid and l -pyroglutamic acid. , To improve the purity of the target product and reduce the industrial cost, it is very necessary to efficiently separate l -glutamic acid and l -pyroglutamic acid in the reaction system.…”

Section: Introductionmentioning

confidence: 99%

Determination and Modeling of Solid–Liquid Equilibrium for the Ternary System of l-Pyroglutamic Acid + l-Glutamic Acid + Water at T = 298.15–328.15 K

Zhang

Huang

Guo

et al. 2020

Ind. Eng. Chem. Res.

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The solid−liquid phase equilibrium for the ternary system of L-pyroglutamic acid + L-glutamic acid + water was determined experimentally by the isothermal solution saturation method at temperatures of 298.15, 308.15, 318.15, and 328.15 K under normal atmosphere. According to the obtained solubility data, four ternary phase diagrams and one variable-temperature phase diagram were constructed. Two pure solids, L-pyroglutamic acid and L-glutamic acid, were generated in the L-pyroglutamic acid + L-glutamic acid + water system. In the phase diagrams, there were in all three crystallization zones, two cosaturated solubility curves and one cosaturated point. The variable-temperature phase diagram for the ternary system of L-pyroglutamic acid + L-glutamic acid + water could be used for separation and purification L-pyroglutamic acid and L-glutamic acid from its mixture. The data of solid− liquid phase equilibrium were correlated and computed with the nonrandom two-liquid (NRTL) model and the Wilson model. The root mean square deviation (RMSD) value was no more than 2.12 × 10 −3 for the Wilson model and 40.3 × 10 −3 for the NRTL model; the Wilson model provided better correlation results than the NRTL model for the ternary system at studied temperatures. The mutual solubility data and ternary phase diagrams for the system were of profound significance for optimizing the purification procedure of L-pyroglutamic acid and L-glutamic acid.

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Construction and evaluation of ternary solid-liquid phase diagram of pyraclostrobin (form IV) and its intermediate in ethanol and N,N-dimethylformamide

Cited by 8 publications

References 15 publications

Determination, Construction, and Evaluation of Ternary and Quaternary Solid–Liquid Phase Equilibrium of Uric Acid, Adenine, and Guanine in Water

Determination, Construction, and Evaluation of Ternary and Quaternary Solid–Liquid Phase Equilibrium of Uric Acid, Adenine, and Guanine in Water

A study on the oxidation of 1‐(4‐chlorophenyl) pyrazolidin‐3‐one to 1‐(4‐chlorophenyl)‐3‐pyrazolol by oxygen

Determination and Modeling of Solid–Liquid Equilibrium for the Ternary System of l-Pyroglutamic Acid + l-Glutamic Acid + Water at T = 298.15–328.15 K

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