Carbonated water for the separation of carboxylic compounds: a chromatography approach

Yuan, Xilong; Richter, Bruce E.; Jiang, Kunqiang; Boniface, Kyle J.; Cormier, A.; Sanders, Connor A.; Palmer, Calvin H.; Jessop, Philip G.; Cunningham, Michael F.; Oleschuk, Richard D.

doi:10.1039/c7gc02812a

Cited by 7 publications

(4 citation statements)

References 43 publications

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“…The development of new chromatographic methods is consistently interesting because the pharmaceutical industries and academia always require a more sensitive, convenient, fast, reproducible, less expensive, and environmentally friendly method for the separation. Many new green chromatographic methods have been developed − for separation of a variety of organic compounds; however, among them, very few are reported for chiral separation. , The chiral separation of racemic compounds is considered very important for the synthetic laboratories or pharmaceutical industries, with respect to the development of new chiral drugs/compounds, for the establishment of the chirally purity of synthesized products. It is well-known, in a chiral drug, that only one of the enantiomers is responsible for the desired physiological effects while the other enantiomer is less active, or inactive, or sometimes even causing adverse effects.…”

Section: Introductionmentioning

confidence: 95%

In Situ Derivatization of (RS)-Mexiletine and Enantioseparation Using Micellar Liquid Chromatography: A Green Approach

Alwera

2018

ACS Sustainable Chem. Eng.

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Developing surfactant-based aqueous solvents as alternatives to organic solvents for chromatographic enantioseparation is highly desired. Surfactants are inexpensive, nontoxic, environmental friendly, and increase the solubility of organic compounds in aqueous solutions. In this work, the impact of surfactant-based aqueous solvents on RP-HPLC enantioseparation of (RS)-mexiletine is studied. The in situ derivatization of (RS)-mexiletine with chirally pure moieties [(S)-levofloxacin, (S)-ketoprofen, (S)-ibuprofen)] was carried out/performed to reduce consumption of organic solvents and side wastes, and to maintain a green approach. We report the impact of increasing concentration of surfactants on separation of diastereomeric derivatives of (RS)-mexiletine on a C18 column of HPLC. Surfactant in water increased the solubility of a diastereomeric derivative, provided the lowest elution time (t R between 2.152 and 10.87 min), and minimized the consumption of solvent. The use of surfactant-containing aqueous mobile phases in chromatographic separations is a good alternative for replacement of organic solvents. The hydrolysis of the synthesized diastereomeric derivatives was carried out, and native enantiomers of mexiletine were isolated and characterized. In addition, the lowest-energy optimized structures were developed using the Gaussian 09 Rev. A.02 program for determination of elution order, and the method was validated for linearity, accuracy, limit of detection (LOD), and limit of quantitation (LOQ).

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Section: Introductionmentioning

confidence: 95%

In Situ Derivatization of (RS)-Mexiletine and Enantioseparation Using Micellar Liquid Chromatography: A Green Approach

Alwera

2018

ACS Sustainable Chem. Eng.

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“…39 Researchers have proposed several methods for delivery of carbonated MPs, including an online membrane engasser, 40,41 pressurization in stainless steel cylinders prior to use, 25 and simply sparging the solvent(s) with CO 2 . 38,42 We sought to design a system that reliably delivers carbonated water MPs to existing UHPLC instrumentation. Initially, sparging was attempted after bypassing the degasser with moderate success, hindered by two major drawbacks: (i) occasional bubble formation leading to pressure drops in the pump and (ii) no direct control of the p CO 2 .…”

Section: Consideration For Sustainable Carbonated and Noncarbonated E...mentioning

confidence: 99%

Optimization of analytical method greenness scores: a case study of amino acid enantioseparations with carbonated aqueous systems

Handlovic,

Farooq Wahab,

Glass

et al. 2024

Green Chem.

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“…Organic solvents generate large amounts of chemical waste that is harmful to the environment and human health while additionally being costly to dispose of. Green analytical chemistry aims at reducing the use of organic solvents, particularly in chromatographic separations [1]. Chromatographic separations are used in the research of new chemicals and in the production of compounds for both their analysis and purification.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, SWC struggles to analyze non-polar compounds due to their low solubility in water [20] and even when enough eluotropic strength is achieved, selectivity is a major issue. More recently, the separation of carboxylic acid compounds (naproxen, ibuprofen, and ketoprofen) was achieved with an amine functionalized silica particle stationary phase and a CO 2 -modified water mobile phase, demonstrating another type of environmentally friendly chemical analysis [1]. Different approaches used to reduce organic solvents have been the introduction of surfactants [21] or additives to the mobile phase [8].…”

Section: Introductionmentioning

confidence: 99%

Natural deep eutectic solvents as the major mobile phase components in high-performance liquid chromatography—searching for alternatives to organic solvents

et al. 2018

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Over the past six decades, acetonitrile (ACN) has been the most employed organic modifier in reversed-phase high-performance liquid chromatography (RP-HPLC), followed by methanol (MeOH). However, from the growing environmental awareness that leads to the emergence of "green analytical chemistry," new research has emerged that includes finding replacements to problematic ACN because of its low sustainability. Deep eutectic solvents (DES) can be produced from an almost infinite possible combinations of compounds, while being a "greener" alternative to organic solvents in HPLC, especially those prepared from natural compounds called natural DES (NADES). In this work, the use of three NADES as the main organic component in RP-HPLC, rather than simply an additive, was explored and compared to the common organic solvents ACN and MeOH but additionally to the greener ethanol for separating two different mixtures of compounds, one demonstrating the elution of compounds with increasing hydrophobicity and the other comparing molecules of different functionality and molar mass. To utilize NADES as an organic modifier and overcome their high viscosity monolithic columns, temperatures at 50 °C and 5% ethanol in the mobile phase were used. NADES are shown to give chromatographic performances in between those observed for ACN and MeOH when eluotropic strength, resolution, and peak capacity were taken into consideration, while being less environmentally impactful as shown by the HPLC-Environmental Assessment Tool (HPLC-EAT) metric. With the development of proper technologies, DES could open a new class of mobile phases increasing the possibilities of new separation selectivities while reducing the environmental impact of HPLC analyses. Graphical abstract Natural deep eutectic solvents versus traditional solvents in HPLC.

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Carbonated water for the separation of carboxylic compounds: a chromatography approach

Abstract: Amine functionalized silica particles and carbonated water were used for the separation of pharmaceutical compounds with carboxylic groups through an ionic exchange mechanism.

Cited by 7 publications

References 43 publications

In Situ Derivatization of (RS)-Mexiletine and Enantioseparation Using Micellar Liquid Chromatography: A Green Approach

In Situ Derivatization of (RS)-Mexiletine and Enantioseparation Using Micellar Liquid Chromatography: A Green Approach

Optimization of analytical method greenness scores: a case study of amino acid enantioseparations with carbonated aqueous systems

Natural deep eutectic solvents as the major mobile phase components in high-performance liquid chromatography—searching for alternatives to organic solvents

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