Method of manufacture of octanedioic acid, precursors, and derivatives
OwnerErich J. Molitor, Brian D. Mulleninventors
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Abstract
A method for the manufacture of 1,8-octanedioic acid comprises: reacting gamma-valerolactone with an alcohol in the presence of an acid or a base catalyst to provide an alkyl pentenoate, converting the alkyl pentenoate in the presence of a metathesis initiator to provide the dialkyl octenedioate, reacting the dialkyl octenedioate with hydrogen in the presence of a hydrogenation catalyst to provide a dialkyl 1,8-octanedioate and hydrolyzing the dialkyl 1,8-octanedioate to provide the 1,8-octanedioic acid.
Claims21
A method for the manufacture of a dialkyl octenedioate having the formula (1)
- wherein R is a C1-18 alkyl,
- the method comprising:
- reacting gamma-valerolactone having the formula (2)
- with an alcohol having the formula (3)
- R—OH (3)
- in the presence of an acid or a base catalyst to provide an alkyl pentenoate having the formula (4)
- and
- converting the alkyl pentenoate having the formula (4) in the presence of a metathesis initiator to provide the dialkyl octenedioate having the formula (1),
- wherein in formulas (3) and (4), R is a C1-18 alkyl.
A method for the manufacture of oct-4-ene-1,8-dioic acid having the formula (7)
- the method comprising:
- reacting gamma-valerolactone having the formula (2)
- with an alcohol having the formula (3)
- ROH (3)
- in the presence of an acid or a base catalyst to provide an alkyl pentenoate having the formula (4)
- wherein R is a C1-18 alkyl;
- hydrolyzing the alkyl pentenoate having the formula (4) to provide 4-pentenoic acid having the formula (8)
- and
- converting 4-pentenoic acid having the formula (8) in the presence of a metathesis catalyst to provide oct-4-ene-1,8-dioic acid having the formula (7).
-32. (canceled)
Dependencies are inferred from the claim text.