Process for the recovery of furfural

• US 10,584,107 B2
• Filed: 10/30/2017
• Issued: 03/10/2020
• Est. Priority Date: 11/01/2016
• Status: Active Grant

• Current Assignee: Shell Oil Company (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:
  US16/346,398
• Publication Number:
  US 20190263767A1
• Time in Patent Office: 862 Days
• Field of Search: 549483
• CPC Class Codes: C07D 307/48 Furfural
• CPC Class Codes: C07D 307/50 Preparation from natural products

Abstract

Disclosed is a process for the extraction of furfural which includes: (a) subjecting a composition comprising furfural, water, at least one acid and an aromatic solvent, with a boiling point higher than that of furfural, to a first separation step providing: (i) an organic phase, and (ii) an aqueous phase; (b) subjecting the aqueous phase of step (a) to a first distillation step to provide: (i) a first in top stream comprising a furfural-water azeotrope; (c) subjecting the first top stream of step (b) to a second separation step to provide: (i) a second top stream comprising a portion of the furfural-water azeotrope; (d) subjecting the second top stream of step (c) to a second distillation step to provide: (i) a third top stream enriched with the furfural-water azeotropic mixture; (e) subjecting the organic phase of step (a) to a third distillation step to provide: a fourth top stream comprising furfural.

Claims

1. A process for the extraction of furfural from a composition comprising furfural, water, at least one acid and an aromatic 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 aromatic solvent and a portion of the furfural, and

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

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

a first top stream comprising a furfural-water azeotrope, and

an aqueous waste stream comprising water and the at least one acid;

(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-water azeotrope, and

a second bottom stream comprising the remainder of the furfural-water azeotrope;

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

a third top stream enriched with the furfural-water azeotropic mixture, and

a third bottom stream comprising furfural;

(e) subjecting the organic phase of step (a) to a third distillation step to provide;

a fourth bottom stream comprising the aromatic solvent, and a fourth top stream comprising furfural,

(f) subjecting the second bottom stream of step (c) to a fourth distillation step to provide;

a fifth top stream comprising the furfural-water azeotrope, which is recycled back to feed the second liquid-liquid separation step of step (c), and

a fifth bottom stream comprising water.

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 aromatic solvent is selected from the group consisting of 1-ethyl-2,3-dimethylbenzene, 1-ethyl-2,5-dimethylbenzene, 1-ethyl-2,4-dimethylbenzene, 1-ethyl-3,4-dimethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, n- and sec-propyl-methyl benzenes with the methyl group located in 2-,3-,4- or 5-position, n- and sec-butyl benzene and n- and sec-pentyl benzene, or any combination thereof.

5. The process according to claim 1, wherein the aromatic solvent has a ratio of aromatic carbons to aliphatic carbons of greater than 1.

6. The process according to claim 1, wherein the second liquid-liquid separation step is operated at a temperature range of from ambient temperature to 120°

C.

7. The process according to claim 1, wherein the distillation step is an atmospheric distillation step or a vacuum distillation step.

8. The process according to claim 1, wherein the third top stream of step (d) is recycled back to feed either:

the second liquid-liquid separation step of step (c) above, or

the first distillation step of step (b), or

the first liquid-liquid separation step of step (a).