Solubility Measurement and Thermodynamic Correlation of 4-(Hydroxymethyl) Benzoic Acid in Nine Pure Solvents and Two Binary Solvent Mixtures at (283.15–323.15) K

Kang, Xiang; Li, Mengya; Li, Jiahui; Kuo, Way; Han, Dandan; Gong, Junbo

doi:10.1021/acs.jced.1c00035

Cited by 4 publications

(5 citation statements)

References 24 publications

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“…This behavior is quite common, and it is manifested by the appearance of a maximum on the molar fraction solubility plotted as a function of binary solvent composition. Some recent examples reported in the literature of such behavior include aqueous binary mixtures of nicotinamide in dimethyl sulfoxide (DMSO) [11], theophylline in 1-butanol [12], phenacetin in 1,4-dioxane [13,14], sulfanilamide in 1,4-dioxane [15], paracetamol in ethanol and propylene glycol [16], 4-(hydroxymethyl)benzoic acid in ethanol [17], and piroxicam in ethanol [18].…”

Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Screening for Green Solvents Improving Sulfamethizole Solubility

2021

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Solubility enhancement of poorly soluble active pharmaceutical ingredients is of crucial importance for drug development and processing. Extensive experimental screening is limited due to the vast number of potential solvent combinations. Hence, theoretical models can offer valuable hints for guiding experiments aimed at providing solubility data. In this paper, we explore the possibility of applying quantum-chemistry-derived molecular descriptors, adequate for development of an ensemble of neural networks model (ENNM), for solubility computations of sulfamethizole (SMT) in neat and aqueous binary solvent mixtures. The machine learning procedure utilized information encoded in σ-potential profiles computed using the COSMO-RS approach. The resulting nonlinear model is accurate in backcomputing SMT solubility and allowed for extensive screening of green solvents. Since the experimental characteristics of SMT solubility are limited, the data pool was extended by new solubility measurements in water, five neat organic solvents (acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, and methanol), and their aqueous binary mixtures at 298.15, 303.15, 308.15, and 313.15 K. Experimentally determined order of decreasing SMT solubility in neat solvents is the following: N,N-dimethylformamide > dimethyl sulfoxide > methanol > acetonitrile > 1,4dioxane >> water, in all studied temperatures. Similar trends are observed for aqueous binary mixtures. Since N,N-dimethylformamide is not considered as a green solvent, the more acceptable replacers were searched for using the developed model. This step led to the conclusion that 4-formylmorpholine is a real alternative to N,N-dimethylformamide, fulfilling all requirements of both high dissolution potential and environmental friendliness.

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Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Screening for Green Solvents Improving Sulfamethizole Solubility

2021

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“…Further studies into yghA may yield capabilities for higher production of 4HMBA, which is an important intermediate in the synthetic process of the antihypertensive drug Eprosartan. 54,55 Given what previous literature suggests, our work highlights the ability of RNA-seq to reveal potential ADH and AKR that otherwise would not have been clear targets for gene inactivation for TPAL stability. We selected gpr for deletion as it had the highest log 2 fold change (1.55) of any ADH or AKR class enzymes identified by RNAseq after a TPAL challenge.…”

Section: Discussionmentioning

confidence: 66%

“…Besides the oxidoreductase capabilities highlighted previously, little is known about this enzyme that may yield 4HMBA production. Further studies into yghA may yield capabilities for higher production of 4HMBA, which is an important intermediate in the synthetic process of the antihypertensive drug Eprosartan 54,55 …”

Section: Discussionmentioning

confidence: 99%

Genome engineering allows selective conversions of terephthalaldehyde to multiple valorized products in bacterial cells

Dickey,

Jones,

Butler

et al. 2023

AIChE Journal

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Deconstruction of polyethylene terephthalate (PET) plastic waste generates opportunities for valorization to alternative products. We recently designed an enzymatic cascade that could produce terephthalaldehyde (TPAL) from terephthalic acid. Here, we showed that the addition of TPAL to growing cultures of Escherichia coli wild‐type strain MG1655 and an engineered strain for reduced aromatic aldehyde reduction (RARE) strain resulted in substantial reduction. We then investigated if we could mitigate this reduction using multiplex automatable genome engineering (MAGE) to create an E. coli strain with 10 additional knockouts in RARE. Encouragingly, we found this newly engineered strain enabled a 2.5‐fold higher retention of TPAL over RARE after 24 h. We applied this new strain for the production of para‐xylylenediamine (pXYL) and observed a 6.8‐fold increase in pXYL titer compared with RARE. Overall, our study demonstrates the potential of TPAL as a versatile intermediate in microbial biosynthesis of chemicals that derived from waste PET.

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“…In contrary to the solvent–solute interactions, the solvent–solvent intermolecular interactions could basically reduce the solubility of solute, which can be quantitatively characterized by the cohesive energy density of solvent in solid–liquid equilibrium. As usual, the higher the cohesive energy density of solvent, the stronger the intermolecular interactions between solvent and solvent molecules, which may result in a lower solubility. ,− In addition to the solvent–solute and solvent–solvent intermolecular interactions, the dissolution behavior of sulfinpyrazone could also be influenced by the molecular structures of solvents and solute, which involves the effects of molecular size , and groups with special properties on solubility.…”

Section: Resultsmentioning

confidence: 99%

Solubility Behavior and Data Correlation of Sulfinpyrazone in Thirteen Pure Solvents from 283.15 to 323.15 K

Qiu,

Zhao,

Liu

et al. 2023

J. Chem. Eng. Data

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This present work is the investigation of the solubility for sulfinpyrazone in 13 monosolvents, water, methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, acetone, acetonitrile, 2-butanone, methyl acetate, ethyl acetate, and npentanol, via a static gravimetric method at temperatures ranging from 283.15 to 323.15 K under atmospheric pressure. The solubility magnitudes are in positive correlation with the absolute temperature in each solvent. Within the experimental temperature range, the solubility is the highest in acetonitrile (103.286 × 10 −3 at 323.15 K) and lowest in water (0.03597 × 10 −3 at 283.15 K). The rough sequences of solubility values in different solvents are methanol > n-pentanol > n-propanol > n-butanol > sec-butanol > ethanol > isopropanol and acetonitrile > acetone > 2-butanone > methyl acetate > ethyl acetate > water in alcohols and nonalcohol solvents, respectively. The results demonstrate that the solubility behaviors of sulfinpyrazone are affected by the combined effects of several factors involving solvent polarity, solvent−solvent intermolecular interactions (quantitatively characterized by cohesive energy density), and molecular structures (molecular sizes and properties of functional groups) of solvents and solutes. Additionally, the Apelblat equation and Yaws equation were employed to correlate the experimental solubility data of sulfinpyrazone in each investigated solvent. The results of average relative deviations and root-mean-square deviations as well as the values of Akaike Information Criterion and Akaike weights reveal that the calculated solubility values by the Apelblat equation are more consistent with the experimental data compared to those by the Yaws equation.

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Solubility Measurement and Thermodynamic Correlation of 4-(Hydroxymethyl) Benzoic Acid in Nine Pure Solvents and Two Binary Solvent Mixtures at (283.15–323.15) K

Cited by 4 publications

References 24 publications

Experimental and Theoretical Screening for Green Solvents Improving Sulfamethizole Solubility

Experimental and Theoretical Screening for Green Solvents Improving Sulfamethizole Solubility

Genome engineering allows selective conversions of terephthalaldehyde to multiple valorized products in bacterial cells

Solubility Behavior and Data Correlation of Sulfinpyrazone in Thirteen Pure Solvents from 283.15 to 323.15 K

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