Methyl vinyl glycolate (MVG) is a chemical compound that can be produced in bulk through a catalytic process from carbohydrates. MVG (also called methyl 2-hydroxybut-3-enoate) is thus a new substance in the series of bio-derived and renewable compounds that can help to reduce the dependence on chemicals from the petrochemical industry and thereby contribute to the climate change mitigation. This is particularly relevant in the production of polymers, the vast majority of which are still produced from oil-based products. The thesis describes the transformation of MVG into a number of new compounds that have potential as building blocks for the production of polymers.
The reactions involve the alkene and the alcohol in MVG, both of which are reactive functional groups for different transformations. The alkene has been reacted in a metathesis reaction, an epoxidation, a cyclocarbonylation and an allylic rearrangement, the latter having been studied in detail with a palladium catalyst to understand the mechanism. The alcohol has been reacted with various electrophiles to form ethers, esters and carbonates. In addition, the alcohol has been oxidized under mild conditions to the corresponding ketone, which is a very unusual and reactive molecule.
The ketone of MVG reacts readily in a Diels-Alder reaction with dienes, thus forming new carbocyclic compounds. A number of these reactions with MVG have been carried out on a large scale, and the compounds have then been investigated as monomers for the preparation of polymers by copolymerization with various reactive substrates. This diverse set of products may support the implementation of MVG on the marked as an alternative to petrochemicals.
Downstream products from MVG, the value tree of MVG.