1,4-Cyclohexanedimethanol:Biosynthesis and Uses

1,4-Cyclohexanedimethanol(CHDM) is a colorless low-melting solid used in the production of polyester resins. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups.

Biosynthesis

A method for producing 1,4-cyclohexanedimethanol, comprising culturing a non-naturally occurring microbial organism having a 1,4-cyclohexanedimethanol pathway, wherein said microbial organism comprises at least one exogenous nucleic acid encoding a 1,4-cyclohexanedimethanol pathway enzyme expressed in a sufficient amount to produce 1,4-cyclohexanedimethanol, under conditions and for a sufficient period of time to produce 1,4-cyclohexanedimethanol, said 1,4-cyclohexanedimethanol pathway comprising an enzyme set selected from the group consisting of:

(1) a p-toluate monooxygenase, and a p-hydroxymethyl benzoate reductase, a dihydroxymethyl benzene dehydrogenase;

(2) a p-toluate kinase, a (p-methylbenzoyloxy)phosphonate reductase (dephosphorylating), a p-methylbenzyl alcohol dehydrogenase, and a p-methylbenzyl alcohol monooxygenase;

(3) a p-methylbenzoyl-CoA synthetase, transferase and/or hydrolase, a phosphotrans-p-methylbenzoylase, a (p-methylbenzoyloxy)phosphonate reductase (dephosphorylating), a p-methylbenzyl alcohol dehydrogenase, and a p-methylbenzyl alcohol monooxygenase;

(4) a p-methylbenzoyl-CoA synthetase, transferase and/or hydrolase, a p-methylbenzoyl-CoA reductase, a p-methylbenzyl alcohol dehydrogenase, and a p-methylbenzyl alcohol monooxygenase;

(5) a p-toluate reductase, a p-methylbenzyl alcohol dehydrogenase, and a p-methylbenzyl alcohol monooxygenase;

(6) a p-toluate monooxygenase, a p-hydroxymethyl benzoyl-CoA synthetase, transferase and/or hydrolase, a p-hydroxymethyl benzoyl-CoA reductase, a dihydroxymethyl benzene dehydrogenase, and chemical reduction;

(7) a p-toluate monooxygenase, a p-hydroxymethyl benzoate kinase, a (p-hydroxymethylbenzoyloxy)phosphonate reductase (dephosphorylating), a dihydroxymethyl benzene dehydrogenase, and chemical reduction;

(8) a p-toluate monooxygenase, a p-hydroxymethyl benzoate kinase, a phosphotrans-p-hydroxymethylbenzoylase, a p-hydroxymethyl benzoyl-CoA reductase, a dihydroxymethyl benzene dehydrogenase, and chemical reduction;

(9) a p-toluate monooxygenase, a p-hydroxymethyl benzoate kinase, a phosphotrans-p-hydroxymethylbenzoylase, a p-hydroxymethyl benzoyl-CoA reductase, a 4-hydroxymethyl cyclohex-1,5-diene carboxyl CoA reductase, a 4-hydroxymethyl cyclohex-1-ene carboxyl-CoA reductase, a 4-hydroxymethylcyclohexanoyl-CoA reductase, and a 4-hydroxymethyl cyclohexane carbaldehyde reductase; and

(10) a p-toluate monooxygenase, a p-hydroxymethyl benzoyl-CoA synthetase, transferase and/or hydrolase, a p-hydroxymethyl benzoyl-CoA reductase, a 4-hydroxymethyl cyclohex-1,5-diene carboxyl CoA reductase, a 4-hydroxymethyl cyclohex-1-ene carboxyl-CoA reductase, a 4-hydroxymethylcyclohexanoyl-CoA reductase, and a 4-hydroxymethyl cyclohexane carbaldehyde reductase.

Uses

1,4-cyclohexanedimethanol (CHDM) is a glycol used for the production of polyesters. Polyester polymers derived from a diol composition utilizing 1,4-cyclohexanedimethanol have low melt viscosities and can be easily processed at acceptable glass transition temperatures for the preparation of powder coatings with a useful balance of chemical resistance, hardness and flexibility together with excellent appearance.

References

US20120156740A1

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