Process for the manufacture of furural and furfural derivatives

Patent metadata

Field	Value
Publication number	US-10087160-B2
Application number	US-201515502828-A
Country	US
Kind code	B2
Filing date	Aug 13, 2015
Priority date	Aug 14, 2014
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

Abstract

The present invention provides a process for preparing furfural and furfural derivatives using a furfural-derived solvent.

First claim

That which is claimed is:

1. A process for preparing furfural and/or furfural derivatives, comprising:
(a) providing an aqueous C 5 sugar-containing feed stream;
(b) contacting an aqueous phase comprising the aqueous C 5 sugar-containing feed stream with an organic phase comprising organic solvent at a temperature in the range of about 100° C. to about 300° C. for a time sufficient to effect a dehydration reaction to convert C 5 sugar to furfural, wherein at least part of the furfural dissolves in the organic solvent phase to form a furfural-containing organic phase;
(c) separating the furfural-containing organic phase from the aqueous phase;
(d) separating furfural from the furfural-containing organic phase;
(e) converting at least part of the furfural to a tetrahydrofuranic derivative to obtain tetrahydrofuranic derivative-containing product; and
(f) providing at least part of the tetrahydrofuranic derivative to step (b) as organic solvent.

2. The process of claim 1 , wherein the tetrahydrofuranic derivative is of the general formula (1):

wherein:
R is selected from the group consisting of H, C 1 -C 5 alkyl, —O—(C 1 -C 5 alkyl),

or
wherein the tetrahydrofuranic derivative is of the general formula (2):

wherein:
R is a C 1 to C 5 alkyl, R2 is H or CH 3 , R3 is H or CH 3 and n is an integer in the range of 4 to 10.

3. The process of claim, wherein the furfural is converted to a tetrahydrofuranic derivative by one or a combination of:
i) a hydrogenation of the furfural, optionally followed by an alkylation;
ii) an aldol-condensation; or
iii) an etherification.

4. The process of claim 1 , wherein the furfural is converted to 2-methyltetrahydrofuran by hydrogenating part of the furfural in the presence of a reactor bed comprising at least a first catalyst to obtain 2-methyltetrahydrofuran-containing product; and wherein in step (e) a least part of the 2-methyltetrahydrofuran is provided to step (b) as organic solvent.

5. The process of claim 4 , wherein the hydrogenation is carried out in one stage.

6. The process of claim 4 , wherein the first catalyst comprises copper.

7. The process of claim 4 , wherein the first catalyst further comprises at least one element selected from the group consisting of chromium, manganese, zinc, aluminum and barium.

8. The process of claim 4 , further comprising a second catalyst in the hydrogenating step, the second catalyst comprising at least one element selected from the group consisting of group 8 metals, group 9 metals and group 10 metals of the periodic table.

9. The process of claim 8 , wherein the second catalyst comprises nickel.

10. The process of claim 8 , wherein the second catalyst further comprises at least one element of the periodic table selected from the group consisting of a group 1 to 7 and group 11 to 15.

11. The process of claim 4 , wherein the first catalyst and optionally the second catalyst is supported on a support material comprising at least one material selected form the group consisting of activated carbon, aluminum oxide, silicon dioxide, silicon carbide, calcium oxide, titanium dioxide, and zirconium dioxide.

12. The process of claim 4 , further comprising in step (e), wherein at least part of the 2-methyltetrahydrofuran-containing product is condensed to obtain a first phase having a water content of at least about 90% by weight and a second phase having a 2-methyltetrahydrofuran content of at least about 80% by weight and at least part of the second phase is provided as organic solvent to step (b).

13. The process of claim 4 , wherein the hydrogenation in step (d) is performed in the presence of a 2-methyltetrahydrofuran derivative.

14. The process of claim 1 , wherein in the range of from 1 to 100 wt % of the organic solvent organic phase in step (b) is a tetrahydrofuranic derivative.

15. The process of claim 1 , wherein the aqueous C 5 sugar-containing feed stream is prepared by:
(a1) providing a feedstock comprising at least one of i) a lignocellulosic feedstock containing glucan and xylan, ii) hemicellulosic material, and iii) C 5 sugar monomers, C 5 oligomers and C 5 polymers;
(a2) contacting the feedstock with an aqueous medium to form a reaction mixture;
(a3) heating the reaction mixture to an elevated temperature with at least one acid for a period of time sufficient to digest at least part the feedstock and form the aqueous C 5 sugar-containing feed stream and a residual product; and
(a4) separating the aqueous C 5 sugar-containing feed stream from the residual product.

16. The process of claim 1 , wherein at least part of the tetrahydrofuranic derivative in the tetrahydrofuranic derivative-containing product is used as a chemical intermediate, fuel additive, or solvent.

17. The process of claim 1 , wherein the organic phase comprises at least one water-immiscible organic solvent.

Assignees

• Shell Oil Co

Inventors

• Chheda Juben Nemchand
• Lange Jean Paul Andre Marie Joseph Ghislain

Classifications

• B01J23/06

  of zinc, cadmium or mercury · CPC title

• C10L1/18

  containing oxygen · CPC title

• B01J2208/027

  Beds · CPC title

• B01J8/0278

  Feeding reactive fluids (for solid material B01J8/0015) · CPC title

• B01J23/755

  Nickel · CPC title