Fermentation route for the production of levulinic acid, levulinate esters and valerolactone and derivatives thereof
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Publication Number
US-10246727-B2
Publication Date
2019-04-02
Expiration Date
Abstract
The invention provides processes for the conversion of pyruvate obtained from sugars or other carbon sources, to valuable C5 materials such as levulinic acid, levulinate esters, valerolactone, and derivatives thereof.
Core Innovation
The invention provides a method for producing 2-oxo-4-valerolactone. The method comprises converting pyruvate to 4-hydroxy-2-oxo-pentanoic acid by aldol addition, and converting 4-hydroxy-2-oxo-pentanoic acid to 2-oxo-4-valerolactone through lactonization.
The described conversion chain uses aldol addition followed by lactonization to form 2-oxo-4-valerolactone from pyruvate-derived intermediates. The document also includes conversions involving 2-hydroxy-4-valerolactone, angelica lactone, 4-valerolactone, and methylene-methyl butyrolactone.
The document emphasizes integration into metabolic pathways and conversion processes that produce C5 platform chemicals from sugar-derived or other feedstock-derived pyruvate, with redox balancing for levulinic acid and 4-valerolactone. It describes producing levulinic acid and levulinate esters and references CoA attachment and sequential reduction, oxidation, dehydration, and lactonization to produce lactones such as 4-valerolactone (γ-valerolactone), 2-oxo-4-valerolactone, 2-hydroxy-4-valerolactone, and angelica lactones.
Claims Coverage
The independent claim is directed to producing 2-oxo-4-valerolactone via two core chemical transformations. The dependent claims refine the sequence by further converting specific lactone intermediates into related named lactones, adding additional conversion steps or specifying particular downstream targets.
Producing 2-oxo-4-valerolactone via aldol addition and lactonization
A method for producing 2-oxo-4-valerolactone by converting pyruvate to 4-hydroxy-2-oxo-pentanoic acid by aldol addition, and converting 4-hydroxy-2-oxo-pentanoic acid to 2-oxo-4-valerolactone through lactonization.
Converting 2-oxo-4-valerolactone to 2-hydroxy-4-valerolactone
The method further includes converting 2-oxo-4-valerolactone to 2-hydroxy-4-valerolactone.
Converting 2-hydroxy-4-valerolactone to angelica lactone
The method further includes converting 2-hydroxy-4-valerolactone into angelica lactone.
Reducing angelica lactone to 4-valerolactone
The method further reduces angelica lactone to 4-valerolactone.
Converting angelica lactone to methylene-methyl butyrolactone
The method further converts angelica lactone into methylene-methyl butyrolactone.
Converting 4-valerolactone to methylene-methyl butyrolactone
A method according to claim 4 in which 4-valerolactone is converted into methylene-methyl butyrolactone.
Overall, the claim set covers forming 2-oxo-4-valerolactone from pyruvate through aldol addition to a hydroxy-oxo pentanoic acid intermediate followed by lactonization. It further covers additional conversions among named lactones, including 2-hydroxy-4-valerolactone, angelica lactone, 4-valerolactone, and methylene-methyl butyrolactone.
Stated Advantages
Not explicitly described in patent.
Documented Applications
Not explicitly described in patent.
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