DIRECT SYNTHESIS OF BIO-BASED ALKYL & FURANIC DIOL ETHERS, ACETATES, ETHER-ACETATES, AND CARBONATES

摘要

A method of preparing a glycol mono-ether or mono-acetate, or carbonate involving either one of two pathways from alkylene glycols, HMF or its reduction derivative products (i.e., FDM, bHMTHFs), is provided. In particular, according to one pathway, the alkylene glycol, HMF or FDM, bHMTHFs are reacted with a dialkyl carbonate in the presence of a deprotonating agent, in substantial absence of an extrinsic catalyst, to produce an ether, and subsequently reacting the ether with an acid base. According to the other pathway, alkylene glycols are reacted with an acetate donor in the presence of an acid, base, to generate an alkylene monoacetate, and etherified with a carbonate in the presence of a deprotonating agent.

主权项

1. A method of preparing a mono-ether from a diol compound, comprising either a first pathway or second pathway, wherein:
in the first pathway, the diol compound is contacted with an R1 organic acid in the presence of a Brønsted acid at a temperature and for time sufficient to form a R1 mono ester of the diol compound, then the R1 mono ester of the diol compound is contacted with a R2 alkyl diester of the formula R2(CO3)R2 in the presence of a deprotonating agent at a temperature and for a time sufficient to form the monoester ether; or in the second pathway, the diol compound is contacted with the an R2 alkyl diester of the formula R2(CO3)R2 in the presence of a deprotonating agent at a temperature and for a time sufficient to form a mono ester of the diol compound, then the mono ester of the diol compound is contacted with an R1 organic acid in the presence of a Brønsted acid at a temperature and for time sufficient to form the monoester ether; wherein R1 and R2 are the same or different alkyl, cyclo-alkyl or aromatic moieties.