Ethyl Lactate: A Green Solvent for Olefin Metathesis

Abstract

Compatibility of selected, commercially available ruthenium olefin metathesis catalysts with ethyl lactate as solvent was evaluated using a range of substrates and conditions. In addition, the preparation of a metathesis catalyst in simplified manner by using the advantages of ethyl lactate was accomplished. The application of ethyl lactate facilitates product isolation (also allowing for lower ruthenium contamination in crude metathesis products) and improves the overall green angle of olefin metathesis.

Kinetics of Alkyl Lactate Formation from the Alcoholysis of Poly(Lactic Acid)

“…Studies have also shown the possibility of using EtLa for the recovery of phenolics and carotenoids (phytonutrients) from fruits and vegetables including palm oil [11][12][13]. More recently, Planer, et al [14] have demonstrated the use of EtLa as a solvent in olefin metathesis. Its application as an entrainer in the reactive distillation of azeotropic mixtures of methyl acetate and methanol has also been exhibited [15].…”

Organocatalysis for versatile polymer degradation

“…21 For example, by transesterification, PLA can be degraded into lactic acid or alkyl lactate (A-La), the former being a platform chemical and the latter having uses as solvent. [23][24][25][26][27] Both degradation products can also be transformed to lactide, which is the first step towards polymer synthesis. [28][29][30] For some polymers, chemical recycling can be achieved thermally by pyrolysis, depolymerising the material directly back to monomers.…”

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

“…Here, the WMS calculation, performed with Molpro, 21,22 has a complex series of steps and was initially based on geometries optimized at CCSD(T)/cc-pV(Q+d)Z or QCISD/MG3, but in our case these have been replaced by M06-2X/6-311++G(d,p) geometries. Isodesmic reaction enthalpies were determined using the five composite atomizations in order to compute the average,̄, and its uncertainty 23 defined as the standard deviation [Σ 5 1 ( −̄) 2 ∕( − 1)] 1∕2 .…”

“…A combination of very low toxicity which renders it suitable for food use and the fact that it can be produced quite simply by fermentation 4 means that sustainable green production of natural ethyl lactate is feasible. It has also been shown that it performs in practice, for example, olefin metathesis reactions conducted in ethyl lactate gave good yields and allowed reductions of the ruthenium catalyst loading required 5 …”

“…It has also been shown that it performs in practice, for example, olefin metathesis reactions conducted in ethyl lactate gave good yields and allowed reductions of the ruthenium catalyst loading required. 5 Measurements of the relative rate of reaction of ethyl lactate with theȮH radical in a Teflon chamber by Kwok et al could be interpreted 6 to predict a trophospheric lifetime of 3.7 days, indicating that it would not prove to be problematic if evaporative spills were to occur. A flashpoint of 46 • C means that it is classified as a combustible (37.8 • C < flashpoint < 93.3 • C) rather than a flammable (flashpoint < 37.8 • C) liquid.…”