Production of 2-hydroxymuconic semialdehyde
AssigneeCelanese Corporation
InventorScott Hagedorn
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Abstract
This invention provides a process for the bioconversion of a non-growth aromatic feed to an accumulated quantity of 2-hydroxymuconic semialdehyde metabolite. 2-Hydroxysemialdehyde is a useful intermediate for subsequent conversions to picolinic acid and pyridine.
Claims12
A process for the production of 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semiladehyde comprising
- (1) Reacting toluene or substituted toluene with a Pseudomonad bacterial culture in the presence of molecular oxygen, said bacterial culture exhibiting catechol 2,3-oxygenase activity that is not inhibited in the presence of less than about 0.1 gram of 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semialdehyde per liter of bioconversion medium, and which exhibits no enzymatic activity that metabolizes 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semialdehyde
- (2) Allowing the 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semialdehyde to accumulate in the bioconversion medium
- (3) recovering the 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semialdehyde.
A process for the production of a 2-hydroxymuconic semialdehyde type metabolite which comprises reacting an aromatic hydrocarbon corresponding to the formula:
- ##STR5## where R is hydrogen or an alkyl group containing between about 1-4 carbon atoms, with Pseodomonad bacterial culture in the presence of molecular oxygen, said culture exhibiting catechol 2,3-oxygenase activity that is not inhibited in the presence of less than about 0.1 gram of a 2-hydroxymuconic semialdehyde metabolite per liter of bioconversion medium, and which lacks active catechol 1,2-oxygenase, 2-hydroxymuconic semialdehyde hydrolase and 2-hydroxymuconic semialdehyde dehydrogenase, wherein the metabolite which is produced to the formulas:
- ##STR6## where R is as previously defined, (3) Allowing said 2-hydroxymuconic semialdehyde type metabolite to accumulate in the bioconversion medium, and
- (4) Recovering said 2-hydroxymuconic semialdehyde product.
A process for the production and accumulation of 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semialdehyde which comprises (1) Reacting catechol or substituted catechol with a Pseudomonad bacterial culture in the presence of molecular oxygen, said culture exhibiting catechol 2,3-oxygenase activity that is not inhibited in the presence of less than about 0.1 gram of 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semialdehyde per liter of bioconversion medium, and which exhibits no enyzmatic activity that metabolizes 2-hydroxymuconic semialdehyde or substitute 2-hydroxymuconic semialdehyde,
- (2) Allowing said 2-hydroxymuconic semialkehyde or substituted 2-hydroxymuconic semialdehyde to accumulate, and
- (3) recovering the 2-hydroxymuconic semialdehyde or substituted 2-hydroxymuconic semialdehyde.
Dependencies are inferred from the claim text.