Solubility of acetaminophen in (ethanol + propylene glycol + water) mixtures: Measurement, correlation, thermodynamics, and volumetric contribution at saturation

Romdhani, Asma; Martínez, Fleming; Almanza, Ovidio; Jouyban, Abolghasem; Acree, William E.

doi:10.1016/j.molliq.2020.114065

Cited by 24 publications

(10 citation statements)

References 44 publications

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“…Selection of Crystallization Conditions. Crystallization conditions for kinetic screening were chosen based on an approximate solubility of 40 mg/g at 20 °C, 43 with the expectation that the solubility at the crystallization temperature of 10 °C would be lower. Concentration values were initially selected as 50, 60, 70, and 80 mg/g for kinetic screening.…”

Section: ■ Case Study 1: Antisolvent Crystallization Of Acetaminophen...mentioning

confidence: 99%

Automated and Material-Sparing Workflow for the Measurement of Crystal Nucleation and Growth Kinetics

Arruda

Cally

Wylie

et al. 2023

Crystal Growth & Design

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The development of digital twins for model-based crystallization process development is often limited by the associated material-intensive and time-intensive experimental screenings. Methods for measuring primary nucleation rates are well established and common practices for academic studies; however, methods for the measurement of secondary nucleation and crystal growth rates are often inconsistent due to differing strategies in the selection of supersaturation models, particle size measurement techniques, and investigated scales. We hereby provide a workflow of automated methods for the experimental screening, data analysis, and parameter estimation for secondary nucleation and crystal growth kinetics in solution crystallization. The methods have been integrated with common experimental protocols in the determination of induction times for primary nucleation and with the use of commercially available tools that can be found in crystallization laboratories across academia and industry. These tools include a Technobis Crystalline as well as process simulation software, currently tailored to gPROMS FormulatedProducts. The methods have been demonstrated for two well-known model systems: antisolvent crystallization of acetaminophen from ethanol−water mixtures and cooling crystallization of a metastable polymorph of L-glutamic acid from water. The presented workflow will serve as a basis to standardize the analysis of crystallization kinetics for new systems, generating kinetic trends using similar methods that would aid in early process development as well as in academic studies.

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Section: ■ Case Study 1: Antisolvent Crystallization Of Acetaminophen...mentioning

confidence: 99%

Automated and Material-Sparing Workflow for the Measurement of Crystal Nucleation and Growth Kinetics

Arruda

Cally

Wylie

et al. 2023

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…These properties adversely influence its dissolution kinetics thereby limiting the design of its liquid formulations. Propylene glycol can be used as a solvent to study and optimize the solubility behavior of important drugs such as acetaminophen ( Romdhani et al., 2020 ) and sulfacetamide ( Osorio et al., 2020 ).…”

Section: Industrial Applications Of Propylene Glycolmentioning

confidence: 99%

Insights on production mechanism and industrial applications of renewable propylene glycol

Okolie

2022

iScience

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“…The details of all the considered systems are provided in the Supplementary Materials S1 in Tables S1 and S2. The example of the solubility data curation of acetaminophen (A) [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48] and phenacetin (P) [49][50][51] in neat water. Open circles represent data points with percentage deviations from back-computed values higher than 10% and were excluded from the analysis.…”

Section: Solubility Data Collection and Curationmentioning

confidence: 99%

“…Noteworthy, 4FM is considered a green solvent, which can be used instead of DMF [28,[70][71][72][73][74]. All temperature-related solubility profiles measured in this study for pure solvents (acetaminophen in DMSO, DMF and 4FM, phenacetin in 4FM), along with the literature data [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51][75][76][77][78][79][80], were presented in the Supplementary Materials S1 in Tables S1 and S2. The solubility profiles determined for the corresponding aqueous binary mixtures are summarized in the Supplementary Materials S1 in Tables S3 and S4.…”

Section: Experimental Solubility Screeningmentioning

confidence: 99%

Solubility Characteristics of Acetaminophen and Phenacetin in Binary Mixtures of Aqueous Organic Solvents: Experimental and Deep Machine Learning Screening of Green Dissolution Media

et al. 2022

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The solubility of active pharmaceutical ingredients is a mandatory physicochemical characteristic in pharmaceutical practice. However, the number of potential solvents and their mixtures prevents direct measurements of all possible combinations for finding environmentally friendly, operational and cost-effective solubilizers. That is why support from theoretical screening seems to be valuable. Here, a collection of acetaminophen and phenacetin solubility data in neat and binary solvent mixtures was used for the development of a nonlinear deep machine learning model using new intuitive molecular descriptors derived from COSMO-RS computations. The literature dataset was augmented with results of new measurements in aqueous binary mixtures of 4-formylmorpholine, DMSO and DMF. The solubility values back-computed with the developed ensemble of neural networks are in perfect agreement with the experimental data, which enables the extensive screening of many combinations of solvents not studied experimentally within the applicability domain of the trained model. The final predictions were presented not only in the form of the set of optimal hyperparameters but also in a more intuitive way by the set of parameters of the Jouyban–Acree equation often used in the co-solvency domain. This new and effective approach is easily extendible to other systems, enabling the fast and reliable selection of candidates for new solvents and directing the experimental solubility screening of active pharmaceutical ingredients.

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Solubility of acetaminophen in (ethanol + propylene glycol + water) mixtures: Measurement, correlation, thermodynamics, and volumetric contribution at saturation

Cited by 24 publications

References 44 publications

Automated and Material-Sparing Workflow for the Measurement of Crystal Nucleation and Growth Kinetics

Automated and Material-Sparing Workflow for the Measurement of Crystal Nucleation and Growth Kinetics

Insights on production mechanism and industrial applications of renewable propylene glycol

Solubility Characteristics of Acetaminophen and Phenacetin in Binary Mixtures of Aqueous Organic Solvents: Experimental and Deep Machine Learning Screening of Green Dissolution Media

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