Methods of producing carboxylic acids

Abstract

The invention relates to methods for enriching monomer content in a cycloalkane oxidation process mixed organic waste stream. In particular, the methods involve combining a biocatalyst with a mixed organic waste stream from a cycloalkane oxidation process, and enzymatically converting dimeric and/or oligomeric components of said waste stream into monomeric components. The methods may enrich the content of diacids, adipic acid, and/or other α,ω-difunctional C6 alkanes in the mixed organic waste stream. Additionally, the treated mixed organic waste streams may have improved burning efficiency.

1 .- 39 . (canceled) 
     
     
         40 . A composition comprising a mixed organic waste stream of a cycloalkane oxidation process and a biocatalyst. 
     
     
         41 . The composition of  claim 40 , wherein the mixed organic waste stream is non-volatile residue NVR, water wash, concentrated water extract stream COP acid, a caustic wash stream, or combinations thereof. 
     
     
         42 . The composition of  claim 40 , wherein the biocatalyst is an isolated enzyme or an enzyme secreted by a naturally occurring or non-naturally occurring host cell. 
     
     
         43 . The composition of  claim 42 , wherein the host cell is tolerant to NVR. 
     
     
         44 . The composition of  claim 43 , wherein the host cell is tolerant to at least 1% of the mixed organic waste stream by volume. 
     
     
         45 . The composition of  claim 42 , wherein the naturally or non-naturally occurring host cell comprises an endogenous or heterologous ω-oxidation pathway that converts aliphatic fatty acids to diacids via hydroxyl-acids and oxo-acids, and wherein the naturally or non-naturally occurring host cell is an n-alkane utilizing yeast or bacterium. 
     
     
         46 . The composition of  claim 45 , where the n-alkane utilizing yeast is  Yarrowia lipolytica, Candida tropicalis, C. albicans, C. cloacae, C. guillermondii, C. intermedia, C. maltosa, C. parapsilosis, C. zeylenoides , or combinations thereof, or yeasts of the  Rhodotonda, Rhizopus, Trichosporon, Debaryomyces  and  Lipomyces  genera or combinations thereof; and wherein the n-alkane utilizing bacteria is  Pseudomonas fluorescens, P. putida, P. aeroginosa, P. oleoverans, Marinobacter hydrocarbonoclasticus, Acinetobacter venetianus, Oleiphilus messinensis, Arthrobacter viscosus, Cupriavidus metallidurans, Rhodococcus erythropolis, Sphingomona spaucimobilis, Burkholderia cepacia, Delftia acidovorans, Alcanivorax diesolei , or combinations thereof. 
     
     
         47 . The composition of  42 , wherein the enzyme is a hydrolase. 
     
     
         48 . The composition of  claim 47 , wherein the hydrolase is a lipase (EC 3.1.1.3), esterase (EC 3.1.1.1), cutinase (EC 3.1.1.74), polyhydroxyalkanoate (PHA) depolymerase (EC 3.1.1.75 & EC 3.1.1.76), lactone hydrolase; gluconolactonases (EC 3.1.1.17), a laccase (EC 1.10.3.2), or combinations thereof. 
     
     
         49 . The composition of  claim 48 , wherein the lactone hydrolase is 1,4-lactonase (EC 3.1.1.25). 
     
     
         50 . The composition of  claim 42 , wherein said enzyme is a P450 cytochrome oxidase, an ω-hydroxylase, ω-oxygenase enzyme or alkane-1-monooxygenase from the class EC 1.14.15.3; a fatty alcohol oxidase; an alcohol dehydrogenase from the class EC 1.1.1.-; a Baeyer-Villiger monooxygenase; a caprolactone lactonohydrolase; a fatty alcohol oxidase; an alcohol dehydrogenase; a cyclohexane-1,2-diol dehydrogenase; a cyclohexane-1,2-dione acylhydrolase; a carboxylesterase from the α,β-hydrolase fold family (EC 3.1.1.-); or combinations thereof. 
     
     
         51 . The composition of  claim 42 , wherein the enzyme is a cyclohexanol dehydrogenase/ChnA from the class EC 1.1.1.245; cyclohexanone monooxygenase/ChnB from the class EC 1.14.13.22; gluconolactonase/ChnC from the class EC 3.1.1.17; ChnD from the class EC 1.1.1.2; cyclohexane-1,2-diol dehydrogenase from EC 1.1.1.174; cyclohexane-1,2-dione acylhydrolase from EC 3.7.1.10 or EC 3.7.1.11; or combinations thereof. 
     
     
         52 .- 58 . (canceled)