Glycerol carbonate as a versatile building block for tomorrow: synthesis, reactivity, properties and applications

Sonnati, Matthieu O.; Amigoni, Sonia; Givenchy, Elisabeth P. Taffin de; Darmanin, Thierry; Choulet, Olivier

doi:10.1039/c2gc36525a

Cited by 448 publications

(343 citation statements)

References 181 publications

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“…4. Glycerol carbonate has a remarkably large range of stability with a high boiling point and a very low melting temperature [3]. From the DSC experiments we detected a glass transition temperature (T g ) at −70.8°C for the pure GC and at −61.3°C for the KF saturated solution.…”

Section: Differential Scanning Calorimetrymentioning

confidence: 88%

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The curious effect of potassium fluoride on glycerol carbonate. How salts can influence the structuredness of organic solvents

Sarri

Tatini

Ambrosi

et al. 2018

Journal of Molecular Liquids

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Glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one, shortly GC) is a dense, viscous, water soluble solvent. The high dielectric constant and dipole moment make it a suitable non-aqueous green solvent for several salts in different applications. GC dissolves significant amounts of inorganic salts such as KF. The saturation of GC with KF leads to the formation of a viscous liquid at room temperature. In this paper, we report on conductivity, rheology, differential scanning calorimetry and infrared spectroscopy experiments that indicate the formation of a glassy liquid where GC molecules and KF ion pairs are intercalated in a firm and ordered bidimensional structure, stabilized by hydrogen bonding and strong ion-dipole interactions.

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Section: Differential Scanning Calorimetrymentioning

confidence: 88%

“…These liquids find remarkable applications in several industrial fields [3,4]. In particular they are excellent solvents for electrolytes, due to their very high dielectric constant and dipole moment that determine the dissociation of ions and promote ion-solvent interactions, respectively.…”

Section: Introductionmentioning

confidence: 99%

The curious effect of potassium fluoride on glycerol carbonate. How salts can influence the structuredness of organic solvents

Sarri

Tatini

Ambrosi

et al. 2018

Journal of Molecular Liquids

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“…Glycerol use is not just limited to cryopreservation. This molecule has been utilized in a wide range of applications in the pharmaceutical and food industry [41][42][43] and more recently as a solvent for green chemistry. 44 While glycerol was the first cryoprotectant molecule to be discovered 45 , the molecular mechanisms by which it acts to prevent freezing damage still remain unclear.…”

mentioning

confidence: 99%

Low-Density Water Structure Observed in a Nanosegregated Cryoprotectant Solution at Low Temperatures from 285 to 238 K

2016

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Liquid water structure is defined by its molecular association through hydrogen bonding. Two different structures have been proposed for liquid water at low temperatures, low density liquid (LDL) and high density liquid (HDL) water. Here we demonstrate a platform which can be exploited to experimentally probe the structure of liquid water in equilibrium at temperatures down to 238 K. We make use of a cryoprotectant molecule, glycerol which when mixed with water lowers the freezing temperature of the solution non-monotonically with glycerol concentration. We use a combination of neutron diffraction and computational modeling to examine the structure of water in glycerolwater liquid mixtures at low temperatures from 285 K to 238 K. We confirm that the mixtures are nano-segregated into regions of glycerol-rich and water-rich clusters. We examine the water structure and reveal that at the temperatures studied here, water forms a low density water structure which is more tetrahedral than that at room temperature. We postulate that nano-segregation allows water to form a low density structure which is protected by an extensive and encapsulating glycerol interface.

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“…Glycerol oligomers may also be considered as superior building blocks for polymerization or polycondensation reactions in comparison to the monomer as the latter leads to low molecular weight reaction products which have a considerable effect on the properties of the macromolecular compounds. The preparation of polymers based on the conversion of oligomerss into macromolecular compounds is emerging as an interesting line of development in the synthesis of polymers [20,21]. Such a method is associated with the synthesis of oligomers with reactive groups at the ends of the molecules.…”

Section: Introductionmentioning

confidence: 99%

Chemo-Enzymatic Synthesis of Oligoglycerol Derivatives

et al. 2016

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Abstract:A cleaner and greener method has been developed and used to synthesize 14 different functionalized oligomer derivatives of glycerol in moderate 29%-39% yields over three steps. After successive regioselective enzymatic acylation of the primary hydroxyl groups, etherification or esterification of the secondary hydroxyl groups and chemoselective enzymatic saponification, the target compounds can efficiently be used as versatile building blocks in organic and supramolecular chemistry.

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Glycerol carbonate as a versatile building block for tomorrow: synthesis, reactivity, properties and applications

Cited by 448 publications

References 181 publications

The curious effect of potassium fluoride on glycerol carbonate. How salts can influence the structuredness of organic solvents

The curious effect of potassium fluoride on glycerol carbonate. How salts can influence the structuredness of organic solvents

Low-Density Water Structure Observed in a Nanosegregated Cryoprotectant Solution at Low Temperatures from 285 to 238 K

Chemo-Enzymatic Synthesis of Oligoglycerol Derivatives

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