Downstream processing of fatty alcohol compositions produced by recombinant host cells

Patent metadata

Field	Value
Publication number	US-12516007-B2
Application number	US-202318334745-A
Country	US
Kind code	B2
Filing date	Jun 14, 2023
Priority date	Mar 7, 2013
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

The disclosure relates to downstream processing of fatty alcohol (FALC) and provides a novel purification method that provides FALC at high purity and yield.

First claim

We claim:

1 . A method of purifying a fatty alcohol (FALC) composition, the method comprising:
(a) producing a starting material comprising FALC and saponifiable impurities by fermentation of a microorganism grown in a fermentation broth, and wherein the saponifiable impurities comprise free fatty acids (FFA), fatty-fatty esters (FFE), and carbonyl-containing compounds; (b) adding a strong base to the starting material to generate a first mixture; and (c) evaporating the first mixture to generate a second mixture enriched for FALC;
wherein, prior to adding the strong base, the starting material is optionally evaporated.

2 . The method of claim 1 , wherein the starting material comprises one or more of:
(a) at least 0.1 weight percent of FFA; (b) at least 0.1 weight percent of FFE; (c) at least 0.1 weight percent of carbonyl-containing compounds; (d) less than 1 weight percent of dialcohol compounds; (e) sulfur or at least one sulfur-containing compound; and/or (f) water.

3 . The method of claim 1 , wherein the strong base reduces the amount of the FFA and the FFE by neutralizing the FFA and saponifying the FFE, wherein saponifying the FFE generates additional FFA for neutralization and generates additional FALC, and wherein the strong base further reduces the amount of carbonyl-containing compounds.

4 . The method of claim 3 , wherein an excess of strong base is added; and the strong base is added in an amount that is about 0.01 to 1.0 weight percent (wt %) in addition to the amount of strong base required to neutralize the FFA and saponify the FFE.

5 . The method of claim 1 , wherein:
an excess of a strong base is used, and the strong base is a hydroxide of a Group I or Group II metal; or the strong base comprises excess sodium hydroxide (NaOH).

6 . The method of claim 3 , wherein the neutralization and saponification is carried out:
for at least 1 hour; at a temperature in a range of about 100° C. to 140° C.; and at ambient pressure to a partial vacuum of 360 torr.

7 . The method of claim 6 , wherein the neutralization and saponification is carried out at a temperature of about 100° C. to about 130° C., for 2 to 4 hours.

8 . The method of claim 1 , wherein:
the saponification (SAP) value of FFA in the second mixture is less than 0.03 mg KOH/g sample; the saponification (SAP) value of FFE in the second mixture is less than 0.4 mg KOH/g sample; an amount of soap in the second mixture is less than 20 ppm; and the FALC in the second mixture is 98% pure.

9 . The method of claim 1 , further comprising:
bleaching the second mixture enriched for FALC with a bleaching agent.

10 . The method of claim 9 , wherein the bleaching agent is a hypochlorite, a peroxide, a bleaching clay, or an absorbent.

11 . The method of claim 9 , wherein the bleaching agent is effective to remove metallic compounds; color bodies; oxidized fatty compounds or fatty compounds with free radicals; or combinations thereof.

12 . The method of claim 1 , further comprising:
hydrogenating the second mixture enriched for FALC with hydrogen and a catalyst.

13 . The method of claim 12 , wherein hydrogenating the second mixture is performed using a one pot slurry reaction, a slurry reaction followed by a packed bed reaction, or two packed bed reactions in series, or a combination thereof.

14 . The method of claim 12 , further comprising fractionating the hydrogenated FALC according to boiling point, wherein FALC having a difference in chain length of two or more carbons are separated.

15 . The method of claim 14 , wherein the hydrogenated FALC comprises at least 50 percent C 12 to C 18 fatty alcohols.

16 . The method of claim 9 , further comprising hydrogenating the second mixture with hydrogen and a catalyst to generate bleached and hydrogenated FALC.

17 . The method of claim 16 , further comprising fractionating the bleached and hydrogenated FALC according to boiling point, wherein FALC having a difference in chain length of two or more carbons are separated.

18 . The method of claim 1 , wherein the starting material is a product of an E. coli fermentation broth.

19 . The method of claim 1 , wherein the starting material comprises a saponification (SAP) value of 20 mg KOH/g or less.

20 . The method of claim 1 , wherein the evaporating is conducted at a temperature:
(a) of less than 150° C. at 1 torr; (b) of less than 187° C. at 5 torr; (c) of about 155° C. at 1 torr; (d) of about 187° C. at 5 torr; or (c) that corresponds to a vapor pressure of a C 18 alcohol.

21 . The method of claim 1 , further comprising:
(d) acidulating the distillation bottom of the first mixture with an acid to generate an acidulated bottom; and (e) optionally collecting the acidulated bottom to recover FFA.

22 . The method of claim 21 , wherein the acid comprises a mineral acid or an organic acid.

23 . The method of claim 21 , wherein the acid is an aqueous mixture comprising at least about 1 wt % of acid.

24 . The method of claim 21 , wherein:
the acid is an aqueous mixture of 10 wt % to 20 wt % sulfuric acid; the sulfuric acid is added to a 20% stoichiometric excess; and the acidulated bottom is maintained at a temperature of 100° C. to 130° C. for at least 1 hour.

25 . The method of claim 21 , wherein the acid comprises hydrochloric acid, hydrobromic acid, hydroiodic acid, hypochlorous acid, chlorous acid, chloric acid, perchloric acid, sulfuric acid, fluorosulfuric acid, nitric acid, phosphoric acid, hexafluorophosphoric acid, chromic acid, boric acid, a sulfonic acid, a carboxylic acid, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, citric acid, lactic acid, gluconic acid, or formic acid.

Assignees

• Genomatica Inc

Inventors

• Ko Myong
• Wang Haibo
• Cole Patricia J
• Liao Perry Y
• Li Simon

Classifications

• C07C29/172

  with the obtention of a fully saturated alcohol · CPC title

• C12P7/02

  containing a hydroxy group · CPC title

• Y02E50/10

  Biofuels, e.g. bio-diesel · CPC title

• C07C29/88 Primary

  by treatment giving rise to a chemical modification of at least one compound (chemisorption C07C29/76) · CPC title

• C07C33/025

  with only one double bond · CPC title