Ethyl lactate: a sinister molecule exhibiting high chemical diversity with potential as a “green” solvent

Abstract

A comprehensive study of the properties and reactivity of ethyl(S)‐lactate has been conducted. The conformational landscape, the enthalpy of formation of the ground state, normalΔfH∘−false(00.16emnormalKfalse)=−600.2±2.2 kJ mol−1, the thermochemistry (entropy, specific heat, enthalpy function), adiabatic ionization energy, and the single bond dissociation energies are also mapped out. Unimolecular elimination reactions leading to water and ethyl acrylate or ethene and lactic acid proceed with barriers in excess of 250 kJ mol−1—with the latter always dominant. The chemical kinetics of the abstraction of H‐atoms from primary, secondary, tertiary, and alcoholic sites by the radicals H• and CH3• are calculated as well as the kinetics of addition reactions to the carbonyl bond.

An experimental and kinetic modeling study of auto-ignition and flame propagation of ethyl lactate/air mixtures, a potential octane booster

“…-H-abstraction reactions by H atoms and CH3 radicals have been taken from Wurmel et al [4]. -H-abstraction rate constants by HO2 radicals from carbon (2) were estimated by similarity to isopropanol as in [16] and were multiplied by 4 to take into account the carbonyl group, while the same abstraction by OH has been taken from the calculation of Mendes et al [17] for iso-butanal.…”

“…Ethyl lactate (C5H10O3) is an oxygenated compound, which is used as solvent and food additive [4,5]. Its molecular structure is illustrated in Fig.…”

Abstraction and addition reactions of four γ‐lactones with H‐atoms and methyl radicals

“…The use of oxygenates as biofuels is of interest due to their potential to enhance cleaner combustion and use as "green solvents". 1,2 Compared to all-carbon molecules, oxygenated alternatives can have more favorable physical properties and reduced emissions of CO, NO 𝑥 , unburned hydrocarbons and soot as the overall available carbon is reduced. Zheng et al 3 studied the effect of oxygenated additives with various functional groups on the combustion and emissions under diesel conditions.…”