Process for preparing an alpha, omega-alkanediol
View Patent ↗The invention relates to a process for preparing an α,ω-alkanediol comprising the steps of a) reacting an alkanoic acid with an alkanol to give an ester, b) oxidizing at least one terminal carbon atom of the ester by contacting with a whole-cell catalyst, which expresses an alkane hydroxylase, in aqueous solution and in the presence of molecular oxygen, to give an oxidized ester, c) hydrogenating the oxidized ester to form the alkanediol and alkanol, and d) removing the alkanol by distillation, forming a reaction mixture depleted with respect to the alkanol, and recycling the alkanol in step b).
1. A process for producing an α,ω-alkanediol comprising:
a) reacting an alkanoic acid with an alkanol to give an ester,
b) oxidizing at least one terminal carbon atom of the ester by contacting with a whole-cell catalyst, which expresses an alkane hydroxylase, in aqueous solution and in the presence of molecular oxygen, to give an oxidized ester,
c) hydrogenating the oxidized ester to form an α,ω-alkanediol and alkanol, and
d) removing the alkanol by distillation, forming a reaction mixture depleted with respect to the alkanol, and
e) recycling the alkanol in a).
2. Process according to claim 1 , wherein the alkanoic acid in a) is an alkanoic acid of the formula H 3 C—(CH 2 ) n —COOH, and where n>0.
3. Process according to claim 1 , wherein the alkanoic acid is butanoic acid.
4. Process according to claim 1 , wherein the alkanoic acid in a) is a carboxylated cycloalkane of the formula C n H 2n−1 COOH, where n>4.
5. Process according to claim 1 , wherein the alkanol is an alkanol of the formula C n OH 2n+2 and n>0.
6. Process according to claim 1 , wherein the alkanoic acid and the alkanol in a) have the same carbon skeleton.
7. Process according to claim 1 , wherein the whole-cell catalyst in b) expresses at least one alkane hydroxylase selected from the group consisting of AlkB from Pseudomonas putida comprising the sequence of SEQ ID NO: 1, a variant having at least 70% identity to SEQ ID NO: 1, CYP153 from Alcanivorans borkumen SK2 comprising the sequence of SEQ ID NO: 2, and a variant having at least 70% identity to SEQ ID NO: 2.
8. Process according to claim 1 , wherein a) is carried out by acid-catalysed ester formation.
9. Process according to claim 1 , wherein a) is carried out in aqueous solution by contacting the alkanoic acid and alkanol with an esterase, protease or lipase.
10. Process according to claim 1 , wherein the alkanoic acid in a) is provided by oxidizing an alkane to the alkanoic acid.
11. Process according to claim 2 , wherein n is 2 to 16.
12. Process according to claim 4 , wherein n is 5 to 8.
13. Process according to claim 8 , wherein a) is carried out in the presence of an organic solvent.
14. Process according to claim 9 , wherein a) is carried out in aqueous solution by contacting with an esterase, protease or lipase in the form of a whole-cell catalyst expressing the esterase or lipase.
15. The process of claim 1 , wherein the whole cell catalyst expresses an alkane hydroxylase that is AlkB from Pseudomonas putida comprising the sequence of SEQ ID NO: 1 or a variant having at least 95% identity to SEQ ID NO: 1.
16. The process of claim 1 , wherein the whole cell catalyst expresses an alkane hydroxylase that is CYP153 from Alcanivorans borkumensis SK2 comprising the sequence of SEQ ID NO: 2 or a variant having at least 95% identity to SEQ ID NO: 2.