Ionic Liquids: A New Strategy in Pharmaceutical Synthesis

Siódmiak, Tomasz; Marszałł, Michał Piotr; Proszowska, Anna

doi:10.2174/157019312800604698

Cited by 48 publications

(16 citation statements)

References 36 publications

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“…ILs have already been well studied as novel solvents for cellulose dissolution and biomass processing (Swatloski et al 2002;Lasse et al 2013;Holding et al 2014Holding et al , 2016Holding et al , 2017. ILs are often defined as 'molten organic salts' with melting points below 100°C (Skoda-Földes 2014; Chowdhury et al 2007;Siódmiak et al 2012), whose chemical and physical properties can be tuned by varying the cations, homologous substituents and anions. Having essentially no vapor pressure, they are non-flammable and in contrast to traditional volatile organic compounds, they are often spuriously described as 'green' solvents (Zhu et al 2006).…”

Section: Introductionmentioning

confidence: 99%

Crystallinity reduction and enhancement in the chemical reactivity of cellulose by non-dissolving pre-treatment with tetrabutylphosphonium acetate

et al. 2020

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Herein, we demonstrate the activation of commercial chemical cellulose pulps towards chemical modification by a pre-treatment step with tetrabutylphosphonium acetate ([P 4444 ][OAc]). A heterogeneous (non-dissolving) pre-treatment was applied allowing for a significant reduction in crystallinity, without concomitant formation of the thermodynamically stable cellulose II. An increase in chemical reactivity was demonstrated using two model reactions; (1) acetylation (organic swelling conditions), where high degrees of substitution (DS) were obtained without the need for a catalyst, and (2) 4-acetamido-TEMPO oxidation (aqueous swelling conditions), where significant degrees of oxidation (DO) were obtained, beyond those for the untreated pulps. In both tests a notable improvement in cellulose reactivity was observed. Regioselectivity of acetylation was assessed using 2D NMR for one low and one high DS sample. The low DS showed a small degree of acetylation of the 6-OH, whereas, the high DS from the pre-treated sample showed mainly mixtures of triacetate and diacetates. Important mechanistic information is attained for future development of aqueous and organic-based reactions involving this ionic liquid pre-treatment.

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Section: Introductionmentioning

confidence: 99%

Crystallinity reduction and enhancement in the chemical reactivity of cellulose by non-dissolving pre-treatment with tetrabutylphosphonium acetate

et al. 2020

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“…Furthermore, IL is also known as 'green solvent' due to negligible vapour pressure [2]. A growing trend has been seen in the development of IL in various applications such as organic synthesis, biocatalysis [3], electrochemistry [4], extraction [5] and in pharmaceutical [6]. IL can be classified into two classes; aprotic and protic ionic liquids.…”

Section: Introductionmentioning

confidence: 99%

Salicylate-Based Protic Ionic Liquids as a Potential Antioxidant

2019

MJAS

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Salicylate-based protic ionic liquids (PILs) were synthesised, characterised and assessed in this study for potential antioxidant in drug design. The synthesised PILs were known as 3-dimethylamino-1-propanol salicylate (3DMAPS) and 3-diethylamino-1propanol salicylate (3DEAPS). Proton nuclear magnetic resonance ( 1 HNMR), Fourier transformation infrared spectroscopy (FTIR) and thermogravimetric analysis (TGA) were used to characterise the synthesised PILs. Furthermore, the antioxidant activity of the synthesised PILs was determined using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical assay. Both 3DMAPS and 3DEAPS showed a good antioxidant activity compared to parent acid (salicylic acid) as these two compounds could scavenge 20% of DPPH free radical at a concentration of 66.76 ± 0.09 µM and 27.27 ± 0.10 µM, respectively. AbstrakCecair ionik protik (PILs) berasaskan salisilat disintesis, dicirikan dan dinilai untuk potensi antioksidan dalam reka bentuk dadah. Dua PILs iaitu 3-dimetilamino-1-propanol salisilat (3DMAPS) dan 3-diethilamino-1-propanol salisilat (3DEAPS) telah berjaya disintesis. Proton resonans magnetik nuklear ( 1 HNMR), spektroskopi transformasi inframerah (FTIR) dan analisis termogravimetrik (TGA) digunakan untuk pencirian PIL yang di sintesis. Tambahan pula, aktiviti antioksidan PIL ditentukan dengan menggunakan ujian radikal bebas 2,2-difenil-1-pikrilhidrazil (DPPH). Kedua-dua 3DMAPS dan 3DEAPS menunjukkan aktiviti antioksidan yang baik berbanding dengan asid induk (asid salisilat) kerana kedua-dua sebatian ini boleh membakar 20% radikal bebas DPPH masing-masing pada kepekatan 66.76 ± 0.09 μM dan 27.27 ± 0.10 μM.Kata kunci: cecair ionic protik, asid salisilik, perangkap radikal, radikal bebas, ujian DPPH

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“…Successfully used in various fields such as organic chemistry synthesis and catalysis [1], electrodeposition [2,3], energy storage [1], separation technologies [4], protein crystallization [1,5,6] the ionic liquids at ambient temperature (RTILs) currently present an increasingly interest especially for the pharmaceutical industry [7][8][9][10][11][12][13]. The growing interest for the applications of RTILs in the industrial synthesis of pharmaceutical compounds can be explained by a number of physicochemical properties highly attractive of RTILs [1,14,15], compared with those of organic solvents used routinely.…”

mentioning

confidence: 99%

Study of Benzoic Acid Solubility in Imidazolium Formate as Pure Ionic Liquid and Its Binary Aqueous Mixtures

Stefan¹,

Chiriac²,

Dragostin³

et al. 2017

Rev. Chim.

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The determination of benzoic acid (BAc) solubility in pure imidazolium formate (ImForm) and their aqueous mixtures of [ImForm/water], was performed by the acid-base titration of the saturated solutions. [ImForm/water] solutions were tested using an ImForm concentration ranging from 1.66-4.33 g/L. The BAc solubility in pure ionic liquid was compared with that of some common organic solvents reported in literature, such as: ethanol, chloroform, cyclohexane. The highest solubility of BAc was for pure ImForm (from 1073 g/L at 293 K up to 2200 g/L at 323 K), the determined values being superior to BAc solubility in organic solvents mentioned. The results confirm that the polar solvents, such as ImForm and ethanol, present the highest BAc solubility values. At 293 K, the mole fraction of BAc in pure ImForm was 2.8 times higher than the mole fraction of BAc in ethanol. The BAc solubility in binary mixtures [ImForm/water] was compared with that determined in [NaCl/water] mixtures. At the same salt concentration, ranging from 1.66 to 4.33 g/L, at a constant working temperature (323 K), the increasing concentration of NaCl lowers the solubility of BAc. In opposite, the increasing of ImForm concentration determines a considerable increase in BAc solubility into the [ImForm/water] mixture. At 277 K, for 1.66 g/L salt concentration in water, the BAc solubility in [salt/water] solvents shows very similar values (~1.3 g/L) for both [ImForm/water] and [NaCl/water]. If the temperature increases to 323 K, the BAc solubility in [ImForm/water] mixture is about 1.5 times higher than that of solubility in distillated water and 2.5 times higher compared to that in [NaCl/water]. It was concluded that the benzoic acid presents a great solubility in pure ImForm and in its [ImForm/water] aqueous mixture.

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Ionic Liquids: A New Strategy in Pharmaceutical Synthesis

Cited by 48 publications

References 36 publications

Crystallinity reduction and enhancement in the chemical reactivity of cellulose by non-dissolving pre-treatment with tetrabutylphosphonium acetate

Crystallinity reduction and enhancement in the chemical reactivity of cellulose by non-dissolving pre-treatment with tetrabutylphosphonium acetate

Salicylate-Based Protic Ionic Liquids as a Potential Antioxidant

Study of Benzoic Acid Solubility in Imidazolium Formate as Pure Ionic Liquid and Its Binary Aqueous Mixtures

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