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US 12,715,835 B2Granted
Biorenewable synthesis of hydroxy-hexanoate esters
AssigneeWisconsin Alumni Research Foundation
InventorsGeorge Huber, Marco Nazareno Dell Anna
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Abstract
A method to make mono- or di-hydroxy-hexanoates. Triacetic acid lactone is converted to a δ-hexalactone or a 4-hydroxy-δ-hexalactone intermediate. The intermediate is treated with an acid in the presence of an alcohol to yield a 5-hydroxy-hexanoate or 4,5-dihydroxy-hexanoate.
Claims19
A method to make mono- or di-hydroxy-hexanoates, the method comprising:
- (a) converting triacetic acid lactone to δ-hexalactone and/or 4-hydroxy-δ-hexalactone;
- and
- (b) treating the δ-hexalactone and/or 4-hydroxy-δ-hexalactone with an acid in the presence of an alcohol to yield 5-hydroxy-hexanoate and/or 4,5-dihydroxy-hexanoate.
A method to make mono- or di-hydroxy-hexanoates, the method comprising:
- (a) hydrogenating triacetic acid lactone to 4-hydroxy-δ-hexalactone in the presence of a catalyst comprising a metal selected from the group consisting of Ni, Nb, Ru, Rh, Pd, Ag, Os, Ir, Pt, and Au;
- and
- (b) treating the 4-hydroxy-δ-hexalactone with an acid in the presence of an alcohol such that at least a portion of the 4-hydroxy-δ-hexalactone is converted to 4,5-dihydroxy-hexanoate.
A method to make mono- or di-hydroxy-hexanoates, the method comprising:
- (a) hydrogenating triacetic acid lactone to 4-hydroxy-δ-hexalactone in the presence of a catalyst comprising a metal selected from the group consisting of Ni, Nb, Ru, Rh, Pd, Ag, Os, Ir, Pt, and Au;
- and;
- and
- (b) converting at least a portion of the 4-hydroxy-δ-hexalactone to δ-hexalactone;
- and
- (c) treating the δ-hexalactone with an acid in the presence of an alcohol such that at least a portion of the δ-hexalactone is converted to 5-hydroxy-hexanoate.
3 more elements
Dependencies are inferred from the claim text.