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Hydroxymethylation of furan and its derivatives in the presence of cation-exchange resins

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Abstract

Reactions of furan, sylvan, and furfuryl alcohol with aqueous formaldehyde in two- and three-phase systems in the presence of various cation-exchange resins in their H+-form or soluble (organic or inorganic) acids have been studied. Both acidity and lipophilicity of the catalysts were found to play roles in hydroxymethylation. By using the strongly acidic cation-exchanger Amberlyst® 15 as catalyst, the following compounds have been prepared: furfuryl alcohol from furan and formaldehyde (yield: 70%), 2,2'-difurylmethane from furfuryl alcohol and furan (yield: 60%), bis(5-methyl-2-furyl)methane from sylvan and formaldehyde (yield: 90%). In the presence of a weakly acidic cation-exchanger (Amberlite IRC-50), 5-methyl-furfuryl alcohol and 2,5-di(hydroxymethyl) furan have been synthesized by reaction of formaldehyde with sylvan and furfuryl alcohol, respectively.

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