IP Library Granted Patent US 10,486,142
Granted Patent B2
US 10,486,142 · App. 15/950,788 · Granted Nov 26, 2019

Compositions and methods related to the production of acrylonitrile

Inventor: Amit Goyal (Cary, NC)
Assignee: Southern Research Institute
B01J23/888B01J23/002B01J23/892B01J23/8926C07C45/52C07C47/22C07C253/26C07C255/08B01J35/1019B01J35/1061B01J37/0203B01J37/0205B01J37/088B01J2523/00Y02P20/52
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Quick Facts
Patent No.
US 10,486,142
App. No.
15/950,788
Granted
Nov 26, 2019
Kind
B2
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.

Claims (40)

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.

Assignments (2)
CONFIRMATORY LICENSE Recorded Jan 19, 2021
From: SOUTHERN RESEARCH INSTITUTE
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 055029/0942 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 19, 2018
From: GOYAL, AMIT
To: SOUTHERN RESEARCH INSTITUTE
Reel/Frame 045584/0226 →
Continuity (3)
Division 15096839 · Apr 12, 2016
Provisional Application 62182092 · Jun 19, 2015
Related Publication 20180229222A1 · Aug 16, 2018