Glycerol and derived solvents: new sustainable reaction media for organic synthesis

Díaz‐Álvarez, Alba E.; Francos, Javier; Lastra-Barreira, Beatriz; Crochet, Pascale; Cadierno, Victorio

doi:10.1039/c1cc10620a

Cited by 233 publications

(119 citation statements)

References 127 publications

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“…Glycerol has been shown to be an interesting alternative for different organic synthesis [3,4] as for instance selective reduction of aldehydes, ketones and ␤-ketoesters with NaBH 4 [5]. Several other examples have been gathered in a review by Diaz-Alvarez et al [6]. Studies by Jérôme and Gu [7][8][9], have shown that, in some reactions, such as the Aza-Michael reaction of p-anisidine and the Michael reaction of indole, glycerol used as solvent is capable to achieve yields up to 80% under catalyst-free conditions, these yields being higher than those obtained with usual solvents.…”

Section: Introductionmentioning

confidence: 99%

Phase equilibrium of the CO2/glycerol system: Experimental data by in situ FT-IR spectroscopy and thermodynamic modeling

Medina-González

Tassaing

Camy

et al. 2013

The Journal of Supercritical Fluids

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OATAO is an open access repository that collects the work of Toulouse researchers and makes it freely available over the web where possible. This is an author-deposited version published in : http://oatao. a b s t r a c tPhase equilibrium experimental data for the CO 2 /glycerol system are reported in this paper. The measurements were performed using an in situ FT-IR method for temperatures ranging from 40 • C to 200 • C and pressures up to 35.0 MPa, allowing determination of the mutual solubility of both compounds. Concerning the CO 2 rich phase, it was observed that the glycerol solubility in CO 2 was extremely low (in the range of 10 −5 in mole fraction) in the pressure and temperature domains investigated here. Conversely, the glycerol rich phase dissolved CO 2 at mole fractions up to 0.13. Negligible swelling of the glycerol rich phase has been observed. Modeling of the phase equilibrium has been performed using the Peng-Robinson equation of state (PR EoS) with classical van der Waals one fluid and EoS/G E based mixing rules (PSRK and MHV2). Satisfactory agreement was observed between modeling results and experimental measurements when PSRK mixing rules are used in combination with UNIQUAC model, although UNIFAC predictive approach gives unsatisfactory representation of experimental behavior.

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Section: Introductionmentioning

confidence: 99%

Phase equilibrium of the CO2/glycerol system: Experimental data by in situ FT-IR spectroscopy and thermodynamic modeling

Medina-González

Tassaing

Camy

et al. 2013

The Journal of Supercritical Fluids

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“…(Ahluwalia and Varma 2009). Although no perfect green solvent exists that could be applied in all situations, several alternatives have recently been developed (i.e., solvents from biomass, ionic liquids, supercritical fluids, etc.) (Diaz-Alvarez et al 2011). Solvents from biomass can be obtained by enzymatic or esterification and fermentation processes.…”

Section: Introductionmentioning

confidence: 99%

Ecotoxicity studies of the levulinate ester series

et al. 2014

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Abstract:The increasing interest in the development of novel green solvents has led to the synthesis of benign alternative products with minimized environmental impacts.However, most of published studies on green solvents focus primarily on their physicochemical properties, with limited emphasis on absence of ecotoxicological assessment. In this study, we evaluated the acute ecotoxicity of four levulinates (levulinic acid, methyl levulinate, ethyl levulinate and butyl levulinate) on freshwater algae (Chlamydomonas reinhardtii), bacteria (Vibrio fischeri), daphnids (Daphnia magna) and earthworms (Eisenia foetida) using various dose-response tests. As a general trend, the toxicity of levulinate esters in aquatic exposure (assessed as the EC 50 ) increased as a function of increasing alkyl chain length; accordingly, the most toxic compound for the aquatic organisms was butyl levulinate, followed by ethyl levulinate and methyl levulinate. The most toxic compound for Eisenia foetida (terrestrial exposure) was methyl levulinate, followed by ethyl levulinate, butyl levulinate and levulinic acid; in this case, we observed an inverse relationship between toxicity and alkyl chain length. Based on both the lowest EC 50 found in the aquatic media and the ratio between predicted environmental concentration (PEC) and the predicted no-effect concentration (PNEC), we have estimated the maximum allowable values in the 2 environment for these chemicals to be 1.093 mg L -1 for levulinic acid, 2.761 mg L -1 for methyl levulinate, 0.982 mg L -1 for ethyl levulinate and 0.151 mg L -1 for butyl levulinate.

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“…O glicerol possui ainda a vantagem de solubilizar facilmente compostos orgânicos, o que o torna apto para ser utilizado como meio reacional em síntese orgânica. 12 Desde os trabalhos seminais de …”

Section: Introductionunclassified

Glycerol as a Solvent in Organic Synthesis

Lenardão

2017

Rev. Virtual Quim.

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Abstract:Glycerol is the main co-product in the biodiesel production. In 2015 were produced 4 million m 3 of biodiesel from Brazilian biomass, which generated more than 300,000 m 3 of glycerol. There are many traditional uses for glycerol in different industrial areas, such as, pharmaceuticals and food, in cosmetics and toiletries. A new and emerging application for glycerol is as a green solvent in organic reactions. In this review are presented and discussed the recent literature on new methodologies developed in Brazil and abroad that involves the use of glycerol as a solvent in organic synthesis.Keywords: Glycerol; green chemistry; solvent; biomass; organic synthesis; sustainability. ResumoO glicerol é o principal co-produto na produção do biodiesel. Em 2015 foram produzidos 4 milhões de m 3 de biodiesel a partir da biomassa brasileira, o que gerou mais de 300.000 m 3 de glicerol. O glicerol é aplicado há décadas em diferentes segmentos industriais, tais como farmacêutico e alimentício, bem como na indústria de cosméticos e higiene pessoal. Uma aplicação nova para o glicerol, que vem crescendo nos últimos anos, é seu uso como um solvente verde em reações orgânicas. Neste artigo de revisão são apresentados e discutidos os trabalhos recentes desenvolvidos no Brasil e no exterior relacionados ao uso do glicerol como solvente em síntese orgânica.

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Glycerol and derived solvents: new sustainable reaction media for organic synthesis

Cited by 233 publications

References 127 publications

Phase equilibrium of the CO2/glycerol system: Experimental data by in situ FT-IR spectroscopy and thermodynamic modeling

Phase equilibrium of the CO2/glycerol system: Experimental data by in situ FT-IR spectroscopy and thermodynamic modeling

Ecotoxicity studies of the levulinate ester series

Glycerol as a Solvent in Organic Synthesis

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