Process for the recovery of furfural

• US 10,562,874 B2
• Filed: 10/30/2017
• Issued: 02/18/2020
• Est. Priority Date: 11/01/2016
• Status: Active Grant

• Current Assignee: Shell USA Incorporated (Shell Plc)
• Original Assignee: Shell Oil Company (Shell Plc)
• Inventors: Chheda, Juben Nemchand, Ehrenreich-Gureja, Charu, Lange, Jean Paul Andre Marie Joseph Ghislain
• Primary Examiner(s): Oh, Taylor V
• Application Number:
  US16/346,361
• Publication Number:
  US 20190270716A1
• Time in Patent Office: 841 Days
• Field of Search: 549483
• CPC Class Codes: B01D 3/143 by two or more of a fractionation, separation or rectification step
• CPC Class Codes: B01D 3/36 Azeotropic distillation
• CPC Class Codes: C07D 307/48 Furfural
• CPC Class Codes: C07D 307/50 Preparation from natural products

Abstract

A process for the extraction of furfural from a composition comprising furfural, water, at least one organic acid and an oxygenate solvent with a boiling point higher than that of furfural. The process includes: (a) subjecting the composition to a first liquid-liquid separation step to provide: (i) an organic phase; (b) subjecting the organic phase of step (a) to a first distillation step to provide: (i) a first top stream; (c) subjecting the first top stream of step (b) to a second liquid-liquid separation step to provide: (i) a second top stream; and (d) subjecting the second top stream of step (c) to a second distillation step to provide: (i) a third top stream comprising a furfural-water azeotrope, and (ii) a third bottom stream comprising furfural.

Claims

1. A process for the extraction of furfural from a composition comprising furfural, water, at least one organic acid and an oxygenate solvent with a boiling point higher than that of furfural, said process comprising:

(a) subjecting the composition to a first liquid-liquid separation step to provide;

an organic phase comprising the oxygenate solvent, furfural, and a portion of the at least one organic acid; and

an aqueous phase comprising the remainder of the at least one organic acid;

(b) subjecting the organic phase of step (a) to a first distillation step to provide;

a first top stream comprising furfural, and a portion of at least one organic acid; and

a first bottom stream comprising the oxygenate solvent;

(c) subjecting the first top stream of step (b) to a second liquid-liquid separation step to provide;

a second top stream comprising a portion of the furfural and a portion of at least one organic acid; and

a second bottom stream comprising a portion of the furfural and a portion of the at least one organic acid;

(d) subjecting the second top stream of step (c) to a second distillation step to provide;

a third top stream comprising a furfural-water azeotrope; and

a third bottom stream comprising furfural; and

(e) subjecting the second bottom stream to a third distillation step to provide;

a fourth top stream comprising a portion of the furfural which is recycled back to feed the second liquid-liquid separation step, and

a fourth bottom stream comprising water and the at least one organic acid.

2. The process according to claim 1, wherein the composition is derived from a product stream of a pentose dehydration step wherein a pentose feed stream is dehydrated.

3. The process according to claim 2, wherein the pentose feed stream is derived from the hydrolysis of a lignocellulosic biomass.

4. The process according to claim 1, wherein the oxygenate solvent is selected from the group consisting of:

propyl guaiacol;

propyl syringol;

guaiacyl propanol, syringyl propanol;

nonyl phenol;

o-, m-, p-substituted cresols;

guaiacol;

2-methoxy-4-propylphenol;

eugenol;

2,6-xylenol;

sec-butyl phenol;

2,5-xylenol; and

any combination thereof.

5. The process according to claim 1, wherein a portion of the first bottom stream of step (b) comprising the oxygenate solvent is recycled into the first liquid-liquid separation step.

6. The process according to claim 1, wherein a portion of the third top stream from step (d) comprising the furfural-water azeotrope is recycled back to feed either the first distillation step or the first liquid-liquid separator.

7. The process according to claim 1, wherein the second bottom stream of step (c) comprising a portion of the furfural and a portion of the at least one organic acid is recycled back to feed the first liquid-liquid separator.