Efficient Sustainable Tool for Monitoring Chemical Reactions and Structure Determination in Ionic Liquids by ESI‐MS

Khemchyan, Levon L.; Khokhlova, E. A.; Seitkalieva, Marina M.; Ananikov, Valentine P.

doi:10.1002/open.201300022

Cited by 7 publications

(7 citation statements)

References 90 publications

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“…The MS spectrometer was equipped with an electrospray-ionization (ESI) source. The operating parameters the following: the ion-spray voltage was 5500 V, the capillary voltage was 40 V, and the capillary temperature was 250 °C. − Mass spectra within a mass range of 100–2000 m / z were acquired in positive-ion mode. The compositions of the polyglycerols were identified by measuring their m / z values.…”

Section: Methodsmentioning

confidence: 99%

Enzymatic Synthesis of Polyglycerol Fatty Acid Esters and Their Application as Emulsion Stabilizers

Peng

Xiong

Hui-yuan

et al. 2018

J. Agric. Food Chem.

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Polyglycerol ester is considered an excellent kind of food emulsifier. The aim of the current study was to synthesize polyglycerol fatty acid esters (PGFEs) with different-sized long-chain fatty acids (i.e. long-carbon fatty acid polyglycerol esters, L-PGFEs; medium-carbon fatty acid polyglycerol esters, M-PGFEs; and short-carbon fatty acid polyglycerol esters, S-PGFEs), using Lipozyme 435 as a catalyst in a solvent-free system. Thereafter, the physicochemical properties of the newly synthesized PGFEs and their potential applications as food emulsifiers were investigated. The maximum esterification efficiencies of L-PGFEs, M-PGFEs, and S-PGFEs were 69.37, 67.34, and 71.68%, respectively, at the optimum conditions: a reaction temperature of 84.48 °C, a reaction time of 6 h, a molar ratio of polyglycerol to fatty acid of 1.35:1, and 1.41 wt % enzyme usage (based on the total substrate mass). A high-performance liquid chromatograph equipped with an evaporative light-scattering detector (HPLC-ELSD) and an electrospray-ionization mass spectrometer (ESI-MS) were employed to identify the synthesized products. The results demonstrated that the main components of these PGFEs were dimeric glycerides (68.3%), triglycerides (13.13%), and a small amount of tetraglycerides (3.18%). The properties of the PGFEs were characterized by physical and chemical methods. Compared with M-PGFEs and S-PGFEs, L-PGFEs had the best physicochemical properties without any obvious odor. Further, the emulsion capabilities of these different long-chain PGFEs were evaluated via examining the particle sizes and storage stabilities and comparing them with those of glycerin monostearate (GMS). The results showed that the emulsions prepared with L-PGFEs had the best stability and the smallest particle sizes (16.8 nm) compared with those of M-PGFEs, S-PGFEs, and GMS, and they were not prone to oil-droplet coalescence or the separation of oil and water. From the current study, the newly synthesized PGFEs with long-chain fatty acids showed the best advantages as a food emulsifier compared with M-PGFEs, S-PGFEs, and even glycerin monostearate.

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Section: Methodsmentioning

confidence: 99%

Enzymatic Synthesis of Polyglycerol Fatty Acid Esters and Their Application as Emulsion Stabilizers

Peng

Xiong

Hui-yuan

et al. 2018

J. Agric. Food Chem.

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“…Because of their unique and flexible properties, ionic liquids find application in numerous fields, including those related to chemical analysis. ILs are employed in electrophoresis, 80,81,815 extraction, 81,85,87,[488][489][490]816,817 gas and liquid chromatography, 80,81,818,819 UV−visible, IR, Raman, and fluorescence spectroscopy, 80,81 NMR, 81,164,165,[167][168][169]820 and mass spectrometry, 80,81,170,821,822 as well as in various sensor systems (Figure 24). 80−82,823−825 Several comprehensive reviews have been published on the topic recently.…”

Section: Ionic Liquids In Biomedical Analyticsmentioning

confidence: 99%

“…835 Among other analytical methods, NMR and mass spectrometry are highly demanded. 164,165,168,170 Thus, UV-light absorbing IL-based matrices were efficiently used in matrix-assisted desorption/ionization mass spectrometry (MALDI-MS) for biosensing bacterial toxins without preliminary separation and purification. 836 As in many other scientific and industrial areas, the tunability of ILs has won them an important place in the field of electrochemical sensors.…”

Section: Ionic Liquids In Biomedical Analyticsmentioning

confidence: 99%

“…Recent progress in analytical studies of ILs using NMR, ,− mass spectrometry, − thermal techniques, − theoretical modeling, ,,,− and other analytical approaches − has revealed an important mechanistic picture. As expected, ILs fully realize the potential of tunable interactions at the molecular level, as discussed above (Figure ).…”

Section: Introductionmentioning

confidence: 99%

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Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine

2017

Self Cite

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Ionic liquids are remarkable chemical compounds, which find applications in many areas of modern science. Because of their highly tunable nature and exceptional properties, ionic liquids have become essential players in the fields of synthesis and catalysis, extraction, electrochemistry, analytics, biotechnology, etc. Apart from physical and chemical features of ionic liquids, their high biological activity has been attracting significant attention from biochemists, ecologists, and medical scientists. This Review is dedicated to biological activities of ionic liquids, with a special emphasis on their potential employment in pharmaceutics and medicine. The accumulated data on the biological activity of ionic liquids, including their antimicrobial and cytotoxic properties, are discussed in view of possible applications in drug synthesis and drug delivery systems. Dedicated attention is given to a novel active pharmaceutical ingredient-ionic liquid (API-IL) concept, which suggests using traditional drugs in the form of ionic liquid species. The main aim of this Review is to attract a broad audience of chemical, biological, and medical scientists to study advantages of ionic liquid pharmaceutics. Overall, the discussed data highlight the importance of the research direction defined as "Ioliomics", studies of ions in liquids in modern chemistry, biology, and medicine.

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“…The operational stability of Lipozyme 435 under pilot-scale conditions was also investigated by reusing it in the BCR. Electrospray ionization mass spectrum (ESI-MS) which was considered as a quick and convenient tool for a qualitative analysis was employed to analyze the composition of esterification products (Khemchyan et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Optimization of oligoglycerol fatty acid esters preparation catalyzed by Lipozyme 435

Wan¹,

Teng²,

Wang³

et al. 2015

Grasas y Aceites

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Oli goglycerol fatty acid esters (OGEs) are an important kind of polyglycerol fatty acid esters (PGEs) which have been widely used as emulsifiers in food, medicine and cosmetic industries. The aim of this study was to investigate the preparation of OGEs by the esterification of olig oglycerol with linoleic acid in a solvent-free system using Lipozyme 435 as the catalyst. The effects of substrate molar ratio, reaction time, reaction temperature, enzyme dosage, and water addition on the efficiency of esterification (EE) were studied. Single factor experiments and response surface methodology (RSM) were employed to optimize the reaction parameters. The optimum conditions were obtained as follows: reaction time 4.52 h, reaction temperature 90 °C, enzyme dosage 2 wt% (based on the total substrate mass), the molar ratio of oligoglycerol to linoleic acid 1.59:1 and no water addition. Under these conditions, the experimental EE (95.82±0.22%) fitted well with that predicted by RSM (96.15%). Similar results were obtained when the process was scaled up to a production of 500 g in a pilot bubble column reactor (BCR). The enzyme maintained 98.2% of the relative activity after 10 batches of reaction in the BCR. Electro spray ionization mass spectrum was employed to rapidly analyze the esterification products, and most species of OGEs have been identified. KEYWORDS: Biocat alysis; Bubble column reactor; Esterification; Immobilized enzyme; Lipase; Oligoglycerol fatty acid estersRESUMEN: Optimización de la preparación de ésteres grasos de oligoglicerol catalizada por Lipozyme 435. Los ésteres grasos de oligoglicerol (OGEs) son una clase importante de ésteres de ácidos grasos de poliglicerol (PGE) que han sido ampliamente utilizados como emulsionantes en alimentación, medicina y en la industria cosmé-tica. El objetivo de este estudio fue investigar la preparación de OGEs mediante la esterificación de oligoglicerol con ácido linoleico en un sistema libre de disolvente utilizando Lipozyme 435 como catalizador. Se estudiaron los efectos en la eficiencia de esterificación (EE) de la relación molar de sustratos, de los tiempos de reacción, las temperaturas de reacción, la dosis de la enzima, y de la adición de agua. Se realizaron ensayos factoriales individuales y metodología de superficie de respuesta (RSM) para optimizar los parámetros de la reacción. Las condiciones óptimas se obtuvieron como sigue: tiempo de reacción 4,52 h, temperatura de reacción 90 °C, dosis de enzima 2% en peso (basado en la masa total del sustrato), la relación molar de ácido linoleico:oligoglicerol fue de 1,59:1 sin adición de agua. Bajo estas condiciones, el EE experimental (95,82±0,22%) se corresponde bien con lo predicho mediante RSM (96,15%). Se obtiene un resultado similar cuando el proceso se escaló a una producción piloto de hasta 500 g en un reactor de columna de burbujas (BCR). La enzima mantiene el 98,2% de su actividad relativa después de 10 lotes de reacción en el BCR. Se empleó un espectrómetro de masas de ionización mediante electrosp...

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Efficient Sustainable Tool for Monitoring Chemical Reactions and Structure Determination in Ionic Liquids by ESI‐MS

Cited by 7 publications

References 90 publications

Enzymatic Synthesis of Polyglycerol Fatty Acid Esters and Their Application as Emulsion Stabilizers

Enzymatic Synthesis of Polyglycerol Fatty Acid Esters and Their Application as Emulsion Stabilizers

Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine

Optimization of oligoglycerol fatty acid esters preparation catalyzed by Lipozyme 435

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