Compositions and methods related to the production of acrylonitrile

Patent metadata

Field	Value
Publication number	US-10486142-B2
Application number	US-201815950788-A
Country	US
Kind code	B2
Filing date	Apr 11, 2018
Priority date	Jun 19, 2015
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

Disclosed herein is a method useful in the process of contacting a first product that includes ethylene glycol, propylene glycol, and glycerol with the catalyst composition, thereby producing a second product that includes acrolein and acetaldehyde.

First claim

What is claimed is:

1. A method comprising the step of:
a) contacting a first product comprising ethylene glycol, propylene glycol, and glycerol with a catalyst composition, thereby producing a second product comprising acrolein and acetaldehyde, wherein the catalyst composition comprises a catalyst having the formula:
M1M2 x M3 y O z

wherein M1 is a metal promoting dehydrogenation and C—O cleavage,
wherein M2 is a metal with acid sites promoting dehydration,
wherein M3 is an amphoteric catalyst support, with acid and base sites, promoting both dehydration and dehydrogenation in conjunction with M1,
wherein x is a molar ratio from about 0.25 to about 4,
wherein y is a molar ratio from about 0.25 to about 4,
wherein z is the total amount of oxygen bound to M1, M2, and M3 and corresponds to the sum of the oxidation states of ML M2, and M3.

2. The method of claim 1 , wherein the method further comprises the steps of:
b) separating at least a portion of the acetaldehyde from the second product; and
c) following step b) converting at least a portion of the acrolein in the second product to acrylonitrile.

3. The method of claim 1 , wherein the first product is produced from C5 and/or C6 sugars in a single step using a multifunctional catalyst.

4. The method of claim 3 , wherein the C5 and/or C6 sugars is C5 and/or C6 hemicellulose and cellulose derived sugars.

5. The method of claim 1 , wherein from about 10 wt % to about 90 wt % of the propylene glycol and glycerol in the first product are converted to acrolein.

6. The method of claim 1 , wherein the second product comprises from about 20 wt % to about 75 wt % of acrolein.

7. The method of claim 3 , wherein the multifunctional catalyst comprises one or more metals selected from the group consisting of Cu, Zn, Sn, Ni, Pt, Pd, Ru, and Re, and a support.

8. The method of claim 7 , wherein the support is selected from the group consisting of Al 2 O 3 , SiO 2 , carbon, TiO 2 , and MgO.

9. The method of claim 1 , wherein step a) is performed at atmospheric pressure.

10. The method of claim 1 , wherein M1 is selected from the group consisting of Cu, Zn, and Sn.

11. The method of claim 1 , wherein M2 is selected from the group consisting of W and Fe.

12. The method of claim 1 , wherein M3 is selected from the group consisting of Zr, Al, Si, Mg, Ti, La, and Ce.

13. The method of claim 1 , wherein x is from about 0.8 to about 2.2.

14. The method of claim 1 , wherein y is from about 0.8 to about 2.2.

15. The method of claim 1 , wherein M1 is Cu.

16. The method of claim 1 , wherein M2 is W.

17. The method of claim 1 , wherein M3 is Zr.

18. The method of claim 1 , wherein the catalyst has the formula CuOWO 3 ZrO 2 , or CuOWO 3 TiO 2 , or CuOWO 3 SiO 2 .

19. A method comprising the step of:
a) contacting a first product comprising ethylene glycol, propylene glycol, and glycerol with a catalyst composition, thereby producing a second product comprising acrolein and acetaldehyde, wherein the catalyst composition comprises a catalyst having the formula:
M1M2 x M3 y O z

wherein M1 is a metal promoting dehydrogenation and C—O cleavage,
wherein M2 is a metal with acid sites promoting dehydration,
wherein M3 is an amphoteric catalyst support, with acid and base sites, promoting both dehydration and dehydrogenation in conjunction with M1,
wherein x is a molar ratio from about 0.25 to about 4,
wherein y is a molar ratio is about 11,
wherein z is the total amount of oxygen bound to M1, M2, and M3id corresponds to the sum of the oxidation states of M1, M2, and M3.

20. The method of claim 19 , wherein the method further comprises the steps of:
b) separating at least a portion of the acetaldehyde from the second product; and
c) following step b) converting at least a portion of the acrolein in the second product to acrylonitrile.

Assignees

• Southern Res Inst

Inventors

• Goyal Amit

Classifications

• B01J23/8926

  Copper and noble metals · CPC title

• C07C45/52

  by dehydration and rearrangement involving two hydroxy groups in the same molecule · CPC title

• C07C29/56

  by isomerisation · CPC title

• B01J37/0203

  the impregnation liquid containing organic compounds · CPC title

• B01J37/088

  Decomposition of a metal salt · CPC title