Small scale production and some reactions of 2-methylfuran

Holdren, Robert
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Methylfuran has been produced from furfural in the laboratory in 91% overall yield by vapor phase hydrogenation over a copper chromite catalyst at atmospheric pressure;A small pilot plant has been constructed for vapor phase hydrogenation of furfural to methylfuran. Methylfuran has been produced in 80% overall yield in this unit;In the laboratory 23 g of methylfuran were produced per gram of copper chromite used, while in the pilot plant 23 pounds of methylfuran were produced per pound of catalyst;The complex copper-ammonium chromate should be decomposed at temperatures below 350° in order to obtain a copper chromite catalyst that is active for the vapor phase hydrogenation of furfural to methylfuran;Small amounts of metals such as calcium or barium are necessary to stabilize the chromite catalyst against reduction;The mol ratio of hydrogen to furfural should be greater than 10:1 in order to obtain good conversion of furfural to methylfuran with one pass of the furfural over the catalyst;The catalyst bed temperature is not a critical factor in the hydrogenation of furfural to methylfuran as long as it is maintained in the range of 200--230°;The vapor pressures of methylfuran have been measured at 15°, 25° and 30°;The total vapor pressures of the furfural-methylfuran system have been determined at 20°, 25.6°, and 30°;The vapor-liquid equilibria of the furfural-methylfuran system have been determined at 738 mm;The reaction of methylfuran with formaldehyde and a wide variety of primary and secondary amine hydrochlorides has been found to give the corresponding Mannich bases. The synthesis of 17 new furfuryl amines by this reaction has been described;The reaction of methylfuran or furfuryl alcohol, with formaldehydes and ammonium chloride has been found to give a nitrogen containing polymer which may find uses as an ion exchange resin;Methods have been described for producing light colored resins from methylfuran by uses of acid catalysts.

Methylfuran, Heterocyclic compounds, Heterocyclic chemistry, Rubber, Artificial, Plant chemistry