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Methoxymethylfurfural
Methoxymethylfurfural (MMF), also 5-methoxymethylfuran-2-carbaldehyde, is an organic compound derived from dehydration of sugars and subsequent etherification with methanol.〔van Putten, R-J., van der Waal J.C. de Jong, E., Rasrendra C.B., Heeres, E.J. and de Vries HG. (2011) Furan-based platform chemicals of the future. Dehydration of hexoses as biosustainable product route. Chemical Reviews submitted.〕 This colorless liquid is soluble in a wide range of solvents including lower alcohols. The molecule is a derivative of furan, containing both aldehyde and ether (methoxymethyl) functional groups. MMF has been detected in the leaves and roots of Chilean ''Jaborosa magellanica'' (Solanaceae) and is a component of mammary and uterus care herb tea.〔(Health King Mammary and Uterus Care Herb Tea )〕 It has a typical odor suggestive of maraschino cherries.〔Hind, J.D. and Crayton, F.H. (1963) Tobacco flavorants. US 3,095,882〕 MMF can be made from a wide range of carbohydrate containing feedstocks including sugar, starch and cellulose using a chemical catalytic process and is a potential "carbon-neutral" feedstock for fuels and chemicals. The company Avantium is currently building a pilot plant to upscale the continuous production of this key YXY building block.〔(Avantium builds YXY pilot plant for green materials and fuels )〕
== Production ==
Related to the production of furfural, MMF can be produced from C-6 sugars hexoses such as glucose and fructose. It is formed via the dehydration of the hexoses and subsequent etherification of HMF.〔 Already in 1936 a batch process was patented for the production of MMF and methyl levulinate.〔Sprengler, O., Weidenhagen, R. and Korotkyj, B. DE632322 Verfahren zur Herstellung von Alkoxymethylfurfurolen und Lävulinsäurealkylestern〕 Bicker reported first order kinetics for the dehydration of fructose, etherification of HMF into 5-methoxymethyl-2-furfural (MMF) and by-products formation in methanol.〔Bicker, M., Kaiser, D., Ott, L. and Vogel, H. (2005) J. of Supercritical Fluids 36, 118-126.〕 An MMF yield of 78% at 99% conversion was obtained at 240 °C and a residence time of 2 s. At short residence times, especially at lower temperatures significant amounts of HMF were observed and smaller amount of MMF. The amount of MMF increased with residence time at the cost of the amount of HMF, which indicates that MMF formation goes through HMF. Reactions in various alcohols by Brown et al. led to the formation of the appropriate HMF ether and levulinic acid ester.〔Brown, D.W., Floyd, A. J., Kinsman, R. G., Roshan-Ali, Y. (19ė82) J. Chem. Tech. Biotechnol. 32, 920-924.〕 A number of primary and secondary alcohols was tested, from methanol to 2-butanol. In methanol a yield of 43% MMF was reported in combination with 47% methyl levulinate. Garves has shown that also cellulose is efficiently degraded by alcohols and strong acid-catalysts at 180 °C to 200 °C within minutes. In methanol methylglucosides, MMF and methyl levulinates plus methyl formates are formed in consecutive reactions, accompanied by some humic residues. Avantium, a high throughput company from the Netherlands announced last year that it is building a pilot plant for the upscaling of its YXY components of which MMF is a key molecule.
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