Structural evolution of the butylated hydroxytoluene/menthol hydrophobic eutectic solvent upon methanol and ethanol cosolvent addition

Mannucci, Giorgia; Busato, Matteo; Tofoni, Alessandro; D’Angelo, P.

doi:10.1016/j.molliq.2023.121302

Cited by 6 publications

(4 citation statements)

References 48 publications

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“…Similar to the glycerol/water system, nanostructuring and phase separations are also invoked in DESs . Recent work on understanding the microstructure in DESs has successfully employed combinations of vibrational spectroscopies, X-ray scattering, and theoretical calculations to investigate DES mixtures at different compositions and DES–cosolvent mixtures. , From our perspective, we focus on coupling X-ray spectroscopy (especially NEXAFS) and scattering to vibrational spectroscopy to provide a unique view of the microstructure and dynamics in DES systems. We will start with the classic DES, glyceline (composed of ChCl and glycerol) phase system to understand how the changes in the hydrogen-bond network lead to a eutectic mixture at specific concentrations.…”

Section: Future Directionsmentioning

confidence: 99%

Probing Complex Chemical Processes at the Molecular Level with Vibrational Spectroscopy and X-ray Tools

Ahmed,

2023

J. Phys. Chem. Lett.

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Understanding the origins of structure and bonding at the molecular level in complex chemical systems spanning magnitudes in length and time is of paramount interest in physical chemistry. We have coupled vibrational spectroscopy and X-ray based techniques with a series of microreactors and aerosol beams to tease out intricate and sometimes subtle interactions, such as hydrogen bonding, proton transfer, and noncovalent interactions. This allows for unraveling the self-assembly of arginine-oleic acid complexes in an aqueous solution and growth processes in a metal–organic framework. Terahertz and infrared spectroscopy provide an intimate view of the hydrogen-bond network and associated phase changes with temperature in neopentyl glycol. The hydrogen-bond network in aqueous glycerol aerosols and levels of protonation of nicotine in aqueous aerosols are visualized. Future directions in probing the hydrogen-bond networks in deep eutectic solvents and organic frameworks are described, and we suggest how X-ray scattering coupled to X-ray spectroscopy can offer insight into the reactivity of organic aerosols.

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Section: Future Directionsmentioning

confidence: 99%

Probing Complex Chemical Processes at the Molecular Level with Vibrational Spectroscopy and X-ray Tools

Ahmed,

2023

J. Phys. Chem. Lett.

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“…Table 9 shows an increase in antioxidant activity, dependent on the addition of alcohol, with a maximum of +58.6%. This substantial enhancement is likely dependent on an interference of EtOH with the existing H-bond of ChLA presumably occupied in stabilising the extract bioactive [68,69]. This phenomenon was further studied by submitting the sample "ChLA (+10% w/v EtOH)" to US irradiation (30 min, as the extraction protocol), evaluating the modification caused by cavitation (see "ChLA Degradation Test (+10% w/v EtOH)" in Table 9).…”

Section: Antioxidant Activity Modification: Etoh Addition and Us Degr...mentioning

confidence: 99%

Food-Waste Valorisation: Synergistic Effects of Enabling Technologies and Eutectic Solvents on the Recovery of Bioactives from Violet Potato Peels

Grillo

Tabasso

Capaldi

et al. 2023

Foods

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The recovery of valuable bioactive compounds from the main underutilised by-products of the food industry is one of the greatest challenges to be addressed in circular economy. Potato peels are the largest waste generated during potato processing. However, they could be a potential source of valuable bioactive compounds, such as polyphenols, that can be reused as natural antioxidants. Currently, environmentally benign enabling technologies and new types of non-toxic organic solvents for the extraction of bioactive compounds may dramatically improve the sustainability of these processes. This paper focuses on the potential inherent in the valorisation of violet potato peels (VPPs) by recovering antioxidants using natural deep eutectic solvents (NaDES) under ultrasound (US)- and microwave (MW)-assisted extraction. Both the enabling technologies provided performances that were superior to those of conventional extractions in terms of antioxidant activity determined by the DPPH· (2,2-diphenyl-1-picrylhydrazyl) assay. In particular, the most promising approach using NaDES is proven to be the acoustic cavitation with a Trolox eq. of 1874.0 mmolTE/gExtr (40 °C, 500 W, 30 min), vs. the 510.1 mmolTE/gExtr of hydroalcoholic extraction (80 °C, 4 h). The shelf-life of both hydroalcoholic and NaDES-VPPs extracts have been assessed over a period of 24 months, and found that NaDES granted a 5.6-fold shelf-life extension. Finally, the antiproliferative activity of both hydroalcoholic and NaDES-VPPs extracts was evaluated in vitro using the MTS assay on human tumour Caco-2 cells and normal human keratinocyte cells (HaCaT). In particular, NaDES-VPPs extracts exhibited a significantly more pronounced antiproliferative activity compared to the ethanolic extracts without a noteworthy difference between effects on the two cell lines.

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“…At variance with traditional solvents, which are pure substances, DESs are prepared by mixing at least two precursor compounds, often solid at room temperature. This opens a wide horizon of opportunities since by judicious choice of the precursors and their molar ratio, or through an appropriate functionalization of the parent molecules, one may directly act on the DES chemical-physical properties, so that these media sit by right in the realm of the “designing” solvents. − It is widely accepted that DES classification relies on the chemical nature of the parent compounds and they are divided into five categories (I–V) . Differently from types I–IV, which are composed by at least one ionic component, the more recent type V DESs are formed by neutral molecular compounds, only.…”

Section: Introductionmentioning

confidence: 99%

Predicting the Thermal Behavior in the Design of Type V Deep Eutectic Solvents: The Combined Role of Polarity and Steric Asymmetry

Mannucci,

Teixeira,

Sosa

et al. 2024

ACS Sustainable Chem. Eng.

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The thermal behavior of the hydrophobic eutectic mixtures formed by L-menthol (MEN) with 4-methoxyphenol (4-Met), 2-tert-butyl-4-methoxyphenol (BHA), 2-tert-butyl-4-ethylphenol (TBEP), and tert-butylhydroquinone (TBHQ) has been investigated to elucidate the different factors governing the solid− liquid equilibrium (SLE) at the molecular level. Our comparative study highlights the contribution of hydrogen-bonding (Hbonding) asymmetry of deep eutectic solvent (DES) precursors, i.e., their ability to act as strong H-bond donors and weak H-bond acceptors or vice versa. When deriving from resonance effects, this concept was previously presented as "polarity asymmetry" and introduced to explain the thermal behavior of type V DES. Here, we expand this concept to demonstrate that steric factors led by the insertion of ad hoc functional groups in the precursor molecules also have a dominant role in the deviation from thermodynamic ideality. In this way, an increasing temperature depression is observed starting from the 4-Met/MEN mixtures up to the BHA/MEN, TBHQ/MEN, and TBEP/MEN ones. The SLE prediction has been carried out through an innovative approach combining the COSMO-RS solvation model and density functional tight-binding molecular dynamics simulations, benchmarked against experimental data, and presented here for the first time. The impact of this work is that of providing new tools for a more conscious understanding and design of hydrophobic type V DES as new sustainable media for applicative purposes.

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Structural evolution of the butylated hydroxytoluene/menthol hydrophobic eutectic solvent upon methanol and ethanol cosolvent addition

Cited by 6 publications

References 48 publications

Probing Complex Chemical Processes at the Molecular Level with Vibrational Spectroscopy and X-ray Tools

Probing Complex Chemical Processes at the Molecular Level with Vibrational Spectroscopy and X-ray Tools

Food-Waste Valorisation: Synergistic Effects of Enabling Technologies and Eutectic Solvents on the Recovery of Bioactives from Violet Potato Peels

Predicting the Thermal Behavior in the Design of Type V Deep Eutectic Solvents: The Combined Role of Polarity and Steric Asymmetry

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