IP Library › Granted Patent US 10,308,582
Granted Patent B2
US 10,308,582 · App. 15/532,397 · Granted Jun 4, 2019

Process for making acrylic acid from dextrose

Inventors: Thomas Binder (Marion, IA); Ahmad K. Hilaly (Forsyth, IL); Naveen S. Sudharsan (Malden, MA); Kris N. Mani (Basking Ridge, NJ); Mitchell Schultz (Decatur, IL)
Assignee: Archer Daniels Midland Company
C07C51/377B01D3/02B01D3/145B01D11/04B01D15/1821B01D15/364B01D61/027B01J43/00C07C51/02C07C51/412C07C51/43C07C51/44C07C51/47C07C57/04C12P7/40C12P7/56C12Y101/01027B01D2325/36
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Quick Facts
Patent No.
US 10,308,582
App. No.
15/532,397
Granted
Jun 4, 2019
Kind
B2
Abstract

A process is described for making acrylic acid from dextrose, which comprises fermenting dextrose; removing solids from the resulting fermentation broth; removing lactic acid from the clarified broth by extraction into an organic solvent; separating out the lactic acid-loaded organic solvent while recycling at least a portion of the remainder back to the fermentation step; reacting the lactic acid with ammonia to provide a dehydration feed comprising ammonium lactate while preferably recycling the organic solvent; carrying out a vapor phase dehydration of the ammonium lactate to produce a crude acrylic acid product; and purifying the crude acrylic acid by distillation followed by melt crystallization, chromatography or both melt crystallization and chromatography.

Claims (22)

1. A process for making acrylic acid from dextrose, comprising:

a. fermenting dextrose in the presence of a biological catalyst to produce a fermentation broth containing lactic acid;

b. removing solids from the fermentation broth to produce a clarified fermentation broth;

c. removing lactic acid from the clarified fermentation broth by extraction into an organic solvent;

d. separating the lactic acid-loaded organic solvent from the fermentation broth remainder after lactic acid has been removed therefrom;

e. recycling at least a portion of the fermentation broth remainder to the fermentation step;

f. reacting lactic acid in the lactic acid-loaded solvent with ammonia to provide a crude dehydration feed comprising ammonium lactate;

g. separating ammonium lactate from organic solvent in the crude dehydration feed to provide a dehydration feed;

h. carrying out a vapor phase dehydration of ammonium lactate in the dehydration feed to produce a crude acrylic acid product;

i. purifying the crude acrylic acid product to provide a purified acrylic acid product, by a process including

a first distillation to remove acetaldehyde and ammonia overhead and provide a bottoms stream comprised predominantly of acrylic acid and propionic acid, and

a second distillation of the bottoms stream from the first distillation to provide a second distillation overhead stream enriched in acrylic acid and a second distillation bottoms stream enriched in propionic acid; and,

j. further purifying the acrylic acid in the second distillation overhead stream by contacting with an the amphoteric ion exchange resin to separate and elute propionic acid into a raffinate or both melt crystallization and by contacting with an the amphoteric ion exchange resin to separate and elute propionic acid into a raffinate.

2. A process according to claim 1 , wherein the purified acrylic acid product of step j) contains less than 3000 ppm by weight of propionic acid.

3. A process according to claim 2 , wherein the purified acrylic acid product of step j) contains less than 1000 ppm by weight of propionic acid.

4. A process according to claim 1 , wherein the separation of lactic acid from the clarified fermentation broth comprises the use of one or more hydrophilic nanofiltration membranes.

5. A process according to claim 1 , wherein the fermentation of dextrose comprises the use of an acid-resistant transformant of Schizosaccharomyces pombe , a recombinant strain of Schizosaccharomyces pombe or an acid-tolerant yeast strain comprising a genome that includes an exogenous lactate dehydrogenase gene.

6. A process according to claim 5 , wherein the further purification involves both melt crystallization and adsorption onto an amphoteric ion exchange resin.

7. A process according to claim 1 , wherein the contacting is accomplished in a series of columns and the eluent passes through the columns as a simulated moving bed.

8. A process according to claim 1 wherein the amphoteric ion exchange resin has a quaternary ammonium group and a carboxy group incorporated on a cross-linked polystyrene frame.

9. A process according to either of claim 1 wherein an eluent of water or of water in combination with an organic solvent is used in step j).

10. A process according to claim 9 , wherein the organic solvent is methanol or acetone.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2017
From: BINDER, THOMAS; HILALY, AHMAD; MANI, KRIS N.; SCHULTZ, MITCHELL J.; SUDHARSAN, NAVEEN S.
To: ARCHER DANIELS MIDLAND COMPANY
Reel/Frame 042729/0654 →
Continuity (2)
Provisional Application 62086331 · Dec 2, 2014
Related Publication 20170362156A1 · Dec 21, 2017
Cited By (3)
US 12,441,676 US 12,570,595 US 12,595,224