Recent progress in antisolvent crystallization

Jia, Shengzhe; Yang, Peng; Gao, Zhenguo; Li, Zhonghua; Chen, Fang; Gong, Junbo

doi:10.1039/d2ce00059h

Cited by 21 publications

(18 citation statements)

References 126 publications

(132 reference statements)

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“…Gas antisolvent precipitation (GAP) is a popular method to crystallize pharmaceutical compounds. 30 In GAP, the solution of an organic solvent containing the product is gradually pressurized with a gas (e.g., supercritical CO 2 ), which expands the solution and decreases the solvent power, causing precipitation of the product. The suitability of GAP for OA crystallization depends on the gas− liquid miscibility, the product concentration, and the solubility of OA in PC.…”

Section: ■ Process Design and Modelingmentioning

confidence: 99%

Electrochemical Reduction of CO₂ to Oxalic Acid: Experiments, Process Modeling, and Economics

Boor

Frijns

Pérez‐Gallent³

et al. 2022

Ind. Eng. Chem. Res.

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We performed H-cell and flow cell experiments to study the electrochemical reduction of CO2 to oxalic acid (OA) on a lead (Pb) cathode in various nonaqueous solvents. The effects of anolyte, catholyte, supporting electrolyte, temperature, water content, and cathode potential on the Faraday efficiency (FE), current density (CD), and product concentration were investigated. We show that a high FE for OA can be achieved (up to 90%) at a cathode potential of −2.5 V vs Ag/AgCl but at relatively low CDs (10–20 mA/cm2). The FE of OA decreases significantly with increasing water content of the catholyte, which causes byproduct formation (e.g., formate, glycolic acid, and glyoxylic acid). A process design and techno-economic evaluation of the electrochemical conversion of CO2 to OA is presented. The results show that the electrochemical route for OA production can compete with the fossil-fuel based route for the base case scenario (CD of 100 mA/cm2, OA FE of 80%, cell voltage of 4 V, electrolyzer CAPEX of $20000/m2, electricity price of $30/MWh, and OA price of $1000/ton). A sensitivity analysis shows that the market price of OA has a huge influence on the economics. A market price of at least $700/ton is required to have a positive net present value and a payback time of less than 10 years. The performance and economics of the process can be further improved by increasing the CD and FE of OA by using gas diffusion electrodes and eliminating water from the cathode, lowering the cell voltage by increasing the conductivity of the electrolyte solutions, and developing better OA separation methods.

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Section: ■ Process Design and Modelingmentioning

confidence: 99%

Electrochemical Reduction of CO₂ to Oxalic Acid: Experiments, Process Modeling, and Economics

Boor

Frijns

Pérez‐Gallent³

et al. 2022

Ind. Eng. Chem. Res.

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“…Antisolvent crystallization as an important unit process for the pharmaceutical industry was appropriate for temperature-sensitive systems, which was selected for the direct crystallization resolution experiments in this work, resulting in the avoiding of the limitations of the high viscosity of solvents at low temperatures. Before the direct crystallization resolution experiments, the solubilities of the three Thr species at 298.15 K and 101.3 kPa in the mixed solvents of water + methanol and CCM-0.3 + methanol were similarly measured as described above, respectively .…”

Section: Methodsmentioning

confidence: 99%

Enhanced Direct Crystallization Resolution of Racemates Mediated in Chiral Ionic Liquid Cosolvent Mixtures: Experimental, Statistical, and QM Simulation Studies

Qin

Lou

et al. 2023

Crystal Growth & Design

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Four chiral ionic liquids (CILs) of 1-hexyl-3-methylimidazolium-l-2-aminobutyrate ([Hmim][l-2-AbA]), 1-hexyl-3-methylimidazolium-d-2-aminobutyrate ([Hmim][d-2-AbA]), di-1-hexyl-3-methylimidazolium-l-malate ([Hmim]2[l-MA]), and di-1-hexyl-3-methylimidazolium-d-malate ([Hmim]2[d-MA]) were first prepared by a neutralization method and adequately characterized. In light of a gravimetric method, the molar fraction solubilities of dl- and d- together with l-threonine (Thr) were then acquired in the binary cosolvent mixtures (CM) of CILs and water, with different mass fractions (ω) of CILs under 101.3 kPa from 283.15 to 333.15 K. In CIL cosolvent mixtures (CCM), a cosolvency phenomenon was observed with the biggest solubilization and discrepant solubilities of Thr enantiomers, with ω of 0.3. Meanwhile, the asymmetry phenomenon was also found from the ternary phase diagram of Thr enantiomers and CCM, in which the enantiomeric excess values at the eutectic point (eeeut) were sensitive to temperature. Subsequently, the nucleation experiments and appearance probability statistics confirmed that CCM with ω of 0.3 (CCM-0.3) can act as excellent nucleation inhibitors which preferred to suppress the nucleation of enantiomeric crystals with the opposite chirality to them, leading to the preferential nucleation of enantiomeric crystals with the same chirality. Furthermore, by coupling seeds and CCM-0.3, the yield and yield ratio of l-Thr products through a direct antisolvent crystallization resolution were improved greatly compared with that in water, where the largest yield ratio was up to 27.47%. At the same time, isosurface diagrams and binding energy calculations by quantum mechanics (QM) revealed that the higher chiral recognition ability of [Hmim]2[l-MA] than [Hmim][l-2-AbA] stemmed from the stronger weak interactions. Particularly, the enhanced direct crystallization resolution can be feasibly recycled owing to the stability and recyclability of the CILs.

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“…However, the stochastic nature of crystallization in solutions makes it difficult to have desirable product properties such as the crystal form and morphology. It affects the potential application of crystals in many various fields, including materials science, pharmaceutical engineering, and bioengineering . Apart from that, chirality is a property that exists widely in nature and organisms.…”

Section: Introductionmentioning

confidence: 99%

Role of Tailor-Made Additives in Crystallization from Solution: A Review

Zhu

Gao

et al. 2023

Ind. Eng. Chem. Res.

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Additives which share a similar molecular structure with the crystallizing parent molecule are called tailor-made additives (TMAs). The inclusion of well-chosen TMAs often has a significant impact on crystallization behaviors. However, how TMAs affect the solution crystallization has seldom been systematically summarized in recent years. Herein this paper reviews the role of TMAs in solution crystallization. First, the effects and action mechanisms of TMAs on crystal nucleation and growth are discussed, respectively. Next, the applications of TMAs in the regulation of crystal properties including the polymorphism, crystal habit, crystal size, and chirality are introduced. Then the recent progress of molecular simulation in predicting the role of TMAs is discussed. Finally, we analyze the existing problems in this field and give an outlook on the future development. This paper is helpful and useful to readers interested in the use of TMAs to control crystallization and design crystals with desired properties.

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Recent progress in antisolvent crystallization

Abstract: Antisolvent crystallization is a significant unit operation in the pharmaceutical industry, especially on drug crystal properties optimization. This paper firstly highlights the applications of antisolvent crystallization in crystal engineering. Antisolvent...

Cited by 21 publications

References 126 publications

Electrochemical Reduction of CO₂ to Oxalic Acid: Experiments, Process Modeling, and Economics

Electrochemical Reduction of CO₂ to Oxalic Acid: Experiments, Process Modeling, and Economics

Enhanced Direct Crystallization Resolution of Racemates Mediated in Chiral Ionic Liquid Cosolvent Mixtures: Experimental, Statistical, and QM Simulation Studies

Role of Tailor-Made Additives in Crystallization from Solution: A Review

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Recent progress in antisolvent crystallization

Abstract: Antisolvent crystallization is a significant unit operation in the pharmaceutical industry, especially on drug crystal properties optimization. This paper firstly highlights the applications of antisolvent crystallization in crystal engineering. Antisolvent...

Cited by 21 publications

References 126 publications

Electrochemical Reduction of CO2 to Oxalic Acid: Experiments, Process Modeling, and Economics

Electrochemical Reduction of CO2 to Oxalic Acid: Experiments, Process Modeling, and Economics

Enhanced Direct Crystallization Resolution of Racemates Mediated in Chiral Ionic Liquid Cosolvent Mixtures: Experimental, Statistical, and QM Simulation Studies

Role of Tailor-Made Additives in Crystallization from Solution: A Review

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Electrochemical Reduction of CO₂ to Oxalic Acid: Experiments, Process Modeling, and Economics

Electrochemical Reduction of CO₂ to Oxalic Acid: Experiments, Process Modeling, and Economics