Methods of producing carboxylic acids

Patent metadata

Field	Value
Publication number	US-9334508-B2
Application number	US-201213525034-A
Country	US
Kind code	B2
Filing date	Jun 15, 2012
Priority date	Jun 17, 2011
Publication date	May 10, 2016
Grant date	May 10, 2016

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.

First claim

The invention claimed is:

1. A method for enriching monomer content in a cycloalkane oxidation process mixed organic waste stream, comprising:
(a) combining a biocatalyst with a mixed organic waste stream from a cycloalkane oxidation process, wherein the biocatalyst is 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), 1,4-lactonase (EC 3.1.1.25), or gluconolactonases (EC 3.1.1.17), or combinations thereof; and
(b) enzymatically converting lactone, dimeric and/or oligomeric components of said mixed organic waste stream into monomeric components.

2. The method according to claim 1 , further comprising treating said mixed organic waste stream with at least one hydrolase enzyme, a naturally or non-naturally occurring host cell which:
a. hydrolyzes oligomeric esters into monomers, and
b. increases the amount of monomer components.

3. The method according to claim 2 , wherein treatment with the hydrolase reduces the viscosity of the mixed organic waste stream to improve the efficiency of burning the stream and/or prepare the stream for further chemical or biological treatment.

4. The method according to claim 3 , further comprising burning the treated mixed organic waste stream for fuel value or to produce a syngas.

5. The method according to claim 3 , further comprising performing an esterification to produce mixed esters or polyols, hydrogenation to produce diols, oxidation to produce diacids, reductive amination, sulfonation, or treating with NH 4 OH or polyamines.

6. The method according to claim 2 , wherein the hydrolyzing oligomeric esters into monomers is performed concurrently with additional separation, chemical conversion, or enzymatic conversion by a biocatalyst.

7. The method according to claim 1 , further comprising:
treating said mixed organic waste stream with a naturally or non-naturally occurring host cell which:
a. hydrolyzes at least a portion of oligomeric esters into monomers;
b. hydrolyzes at least a portion of lactones into hydroxy-acids; or
c. oxidizes at least a portion of linear C4-C6 monoacids, hydroxy-acids and oxo-acids to the corresponding diacids, and
increasing the amount of diacids.

8. The method according to claim 7 , further comprising esterifying the diacids prior to separation into C4, C5, or C6 diacids.

9. The method according to claim 1 , further comprising:
treating said mixed organic waste stream with a non-naturally occurring host cell, which:
a. hydrolyzes at least a portion of oligomeric esters into monomers;
b. hydrolyzes at least a portion of ε-caprolactone to 6-hydroxy-caproic acid;
c. oxidizes at least a portion of caproic acid, 6-hydroxycaproic acid and 6-oxocaproic acid to adipic acid;
d. converts at least a portion of the cyclic C6 components to adipic acid;
e. catabolizes at least a portion of C3, C4 and C5 components; or
f. catabolizes C6 components at a lower rate than C3, C4 and C5 components, and increasing the concentration of adipic acid and reducing the amount of mono-acids and hydroxyacids.

10. The method according to claim 1 , further comprising:
treating said mixed organic waste stream with a non-naturally occurring host cell which:
a. hydrolyzes at least a portion of oligomeric esters into monomers;
b. oxidizes at least a portion of caproic acid to 6-hydroxycaproic acid;
c. converts at least a portion of the cyclic C6 components to 6-hydroxycaproic acid or 6-oxocaproic acid;
d. catabolizes at least a portion of C3, C4 and C5 components; or
e. catabolizes C6 components at a lower rate than C3, C4 and C5 components; and expressing at least one biosynthetic pathway enzyme to convert adipic acid, 6-hydroxycaproic acid or 6-oxohexanoic acid to 1,6-hexanediol, 6-aminocaproic acid, ε-caprolactam or hexamethylenediamine, and
converting C6 components and precursors present in said stream to α, ω-difunctional C6 alkanes.

11. The method according to claim 10 , wherein the non-naturally occurring host cell which converts oligomeric esters, caproic acid, and cyclic C6 compounds to 6-hydroxycaproic acid, 6-oxohexanoic acid, and adipic acid also produces 1,6-hexanediol.

12. The method according to claim 11 , where the non-naturally occurring host cell producing 1,6-hexanediol expresses an aldehyde dehydrogenase catalyzing the conversion of 6-oxohexanoic acid to 6-hydroxycaproic acid, and an alcohol dehydrogenase catalyzing the conversion of 6-hydroxycaproic acid to 1,6-hexanediol.

13. The method according to claim 10 , wherein the non-naturally occurring host cell which converts oligomeric esters, caproic acid, and cyclic C6 compounds to 6-hydroxycaproic acid, 6-oxohexanoic acid, or adipic acid also produces 6-aminocaproic acid.

14. The method according to claim 13 , where the non-naturally occurring host cell producing 6-aminocaproic acid expresses an aminotransferase which converts 6-oxohexanoic acid to 6-aminocaproic acid.

15. The method according to claim 14 , where the non-naturally occurring host cell producing 6-aminocaproic acid also expresses an amidohydrolase which converts 6-aminocaproic acid to ε-caprolactam.

16. The method according to claim 14 , where the non-naturally host cell producing 6-aminocaproic acid also produces hexamethylenediamine via an aldehyde dehydrogenase which converts 6-aminocaproic acid to 6-aminohexanal, and a 1-aminotransferase which converts 6-aminohexanal to hexamethylenediamine.

17. The method according to claim 1 , wherein the mixed organic waste stream from a cycloalkane oxidation process further comprises a non-volatile residue (NVR), water wash, a concentrated water extract (COP acid), a caustic wash stream, or combinations thereof.

18. The method according to claim 1 , further comprising adding an isolated enzyme or an enzyme secreted by a naturally occurring or non-naturally occurring host cell, and said enzyme is a P450 cytochrome oxidase, an w-hydroxylase, w-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; or a carboxylesterase from the α,β-hydrolase fold family (EC 3.1.1.-).

19. The method according to claim 1 , further comprising adding an isolated enzyme or an enzyme secreted by a naturally occurring or non-naturally occurring host cell, wherein said 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.

20. The method according to claim 2 , 7 , 9 , or 10 , further comprising hydrolyzing of oligomeric esters into monomers by an isolated or immobilized hydrolase, or an endogenous or heterologous hydrolase secreted by a naturally or non-naturally occurring host cell during fermentation and bioconversion.

21. The method according to claim 2 , 7 , 9 , or 10 , further comprising catalyzing hydrolysis of oligomeric esters into monomers by a hydrolase that is active at acidic pH, a physiological pH, or an alkaline pH.

22. The method according to claim 7 , 9 or 10 , where the naturally or non-naturally

Assignees

• Pearlman Paul S
• Chen Changlin
• Botes Adriana L
• Invista North America Sarl

Inventors

• Pearlman Paul S
• Chen Changlin
• Botes Adriana L

Classifications

• C12Y301/01076

  Poly(3-hydroxyoctanoate) depolymerase (3.1.1.76) · CPC title

• C12Y301/01075

  Poly(3-hydroxybutyrate) depolymerase (3.1.1.75) · CPC title

• C12Y301/01074

  Cutinase (3.1.1.74) · CPC title

• C12Y301/01017

  Gluconolactonase (3.1.1.17) · CPC title

• C12Y301/01003

  Triacylglycerol lipase (3.1.1.3) · CPC title