Abstract
In this study, we report a detailed experimental and theoretical investigation of three glycol derivatives, namely ethane-1,2-diol, 2-methoxyethan-1-ol and 1,2-dimethoxy ethane. For the first time, the X-ray spectra of the latter two liquids was measured at room temperature, and they were compared with the newly measured spectrum of ethane-1,2-diol. The experimental diffraction patterns were interpreted very satisfactorily with molecular dynamics calculations, and suggest that in liquid ethane-1,2-diol most molecules are found in gauche conformation, with intramolecular hydrogen bonds between the two hydroxyl groups. Intramolecular H-bonds are established in the mono-alkylated diol, but the interaction is weaker. The EDXD study also evidences strong intermolecular hydrogen-bond interactions, with short O···O correlations in both systems, while longer methyl-methyl interactions are found in 1,2-dimethoxy ethane. X-ray studies are complemented by micro Raman investigations at room temperature and at 80 °C, that confirm the conformational analysis predicted by X-ray experiments and simulations.
Highlights
Ethylene glycol and its mono-alkyl ether derivative 2-methoxyethan-1-ol (ME, known as methylcellosolve) have many applications in several fields
Renewed interest in Ethylene glycol (EG) was recently found in the field of solvents for green and sustainable chemistry, where it was reported that EG can be used as a hydrogen bond donor to form
The Energy dispersive X-ray dispersion (EDXD) technique is a variant of X-ray diffraction that exploits the dependence of diffracted intensity on the energy of the radiation, according to the definition of the scattering variable for the Compton scattering between a photon and an electron: 4π sin(θ)
Summary
Ethylene glycol (ethane-1,2-diol; EG) and its mono-alkyl ether derivative 2-methoxyethan-1-ol (ME, known as methylcellosolve) have many applications in several fields. EG is used in engineering and biology, acting as a coolant, an antifreeze, an anti-icing agent in gas pipelines, de-icing solutions for vehicles and runways of airports and a cryo-protectant, in addition to finding widespread application in the synthesis of many polymers [1] and pharmaceuticals [2]. Amongst other uses, it serves as an ingredient of electrolytic capacitors, printer’s inks, and it is used as a solvent. Cellosolves are used as industrial and biological solvents, surfactants, detergents and wetting agents. Renewed interest in EG was recently found in the field of solvents for green and sustainable chemistry, where it was reported that EG can be used as a hydrogen bond donor to form
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