IP Library Granted Patent US 10,722,869
Granted Patent B2
US 10,722,869 · App. 16/662,914 · Granted Jul 28, 2020

Porous shaped metal-carbon products

Inventors: Valery Sokolovskii (Santa Clara, CA); Alfred Hagemeyer (Sunnyvale, CA); James A. W. Shoemaker (Gilroy, CA); Elif Ispir Gürbüz (San Francisco, CA); Guang Zhu (Union City, CA); Eric L. Dias (Belmont, CA)
Assignee: Archer-Daniels-Midland Company
B01J23/755B01J21/18B01J23/30B01J23/42B01J23/6527B01J23/687B01J27/22B01J35/0006B01J35/023B01J35/026B01J35/04B01J35/1004B01J35/1033B01J35/1038B01J35/1042B01J35/1061B01J35/1066B01J37/0018B01J37/04B01J37/084B01J37/18C01B32/382C04B35/111C04B35/117C04B35/532C04B35/636C04B35/6365C07C29/60C07C51/313C07C51/377C07C209/16C07D307/20C09C1/48B01J2523/00C01P2004/60C01P2006/12C01P2006/16C04B2235/3258C04B2235/3279C04B2235/40C04B2235/404C04B2235/405C04B2235/407C04B2235/408C04B2235/424C04B2235/442C04B2235/5409C04B2235/6021C04B2235/658C04B2235/6562C04B2235/6567C04B2235/6582C04B2235/6586C04B2235/664
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Quick Facts
Patent No.
US 10,722,869
App. No.
16/662,914
Granted
Jul 28, 2020
Kind
B2
Abstract

The present invention provides a porous metal-containing carbon-based material that is stable at high temperatures under aqueous conditions. The porous metal-containing carbon-based materials are particularly useful in catalytic applications. Also provided, are methods for making and using porous shaped metal-carbon products prepared from these materials.

Claims (21)

1. A process for producing a C 3 -C 6 diol from a corresponding C 3 -C 6 polyol, the process comprising:

contacting the C 3 -C 6 polyol with hydrogen in the presence of a hydrodeoxygenation catalyst comprising a porous, shaped metal-carbon product to form the corresponding C 3 -C 6 diol, wherein the metal-carbon product comprises at least one metal component selected from the group consisting of Pd, Pt, Ir, Mo, W, V, Mn, Re, Zr, Ni, Cu, La, Sm, Y, Zn, Cr, Ge, Sn, Ti, Au, Rh, Co, and combinations thereof.

2. The process of claim 1 , wherein the metal component comprises Mo, W, or a mixture thereof.

3. The process of claim 1 , wherein the metal component is present at a metal loading in the range of from about 0.5 wt % to about 10 wt %.

4. The process of claim 1 , wherein the C 3 -C 6 polyol is selected from the group consisting of 1,2,6-hexanetriol, 1,2,5-pentanetriol, 2H-tetrahydropyran-2-methanol, tetrahydrofuran-2,5-dimethanol, furan-2,5-dimethanol, 2,5-dihydrofuran-2,5-dimethanol, levoglucosenone, levoglucosan, levoglucosenol, 1,6-anhydro-3,4-dideoxy-p-D-pyranose-2-one, isosorbide, hydroxymethylfurfural, sorbitol, glucose, fructose, xylitol, 3,4-dihydro-2H-pyran-2-carbaldehyde, 1,2,5,6-hexanetetraol, 1,2,3,5,6-hexanepentanol, 1,5-anhydro-3,4-dideoxyhexitol, 5-hydroxy-2H-tetrahydropyran-2 methanol, furfural, furfuryl alcohol, tetrahydrofurfuryl alcohol, a pentose, and a hexose.

5. The process of claim 1 , wherein the C 3 -C 6 diol is selected from the group consisting of 1,5-pentanediol and 1,6-hexanediol.

6. The process of claim 1 , wherein the C 3 -C 6 polyol comprises 1,2,6-hexanetriol and the C 3 -C 6 diol comprises 1,6-hexanediol.

7. The process of claim 1 , wherein the porous, shaped metal-carbon product further comprises a metal deposited on the surfaces of the porous, shaped metal-carbon product.

8. The process of claim 1 , wherein the porous, shaped metal-carbon product further comprises Pt deposited on the surfaces of the porous, shaped metal-carbon product.

9. The process of claim 8 , wherein the metal component of the porous, shaped metal-carbon product comprises W.

10. The process of claim 1 , wherein the contacting step is carried out at a temperature in the range of from about 80° C. to about 200° C.

11. The process of claim 1 , wherein the hydrogen is present at a pressure in the range of from about 200 psig to about 3000 psig.

12. The process of claim 1 , wherein the C 3 -C 6 diol is produced at a selectivity of at least about 80%.

13. The process of claim 1 , wherein the porous, shaped metal-carbon product exhibits a radial piece crush strength of greater than about 4.4 N/mm (1 lb/mm).

14. The process of claim 1 , wherein no more than about 10% of the pore volume of the porous, shaped metal-carbon product is from pores having a pore diameter less than about 10 nm.

15. The process of claim 1 , wherein the porous, shaped metal-carbon product comprises a specific pore volume of pores having a diameter in the range of from 1.7 nm to 100 nm, as measured by the BJH process, that is from about 0.1 cm 3 /g to about 1.5 cm 3 /g.

16. The process of claim 1 , wherein the carbonaceous material comprises carbon black, activated carbon, and/or graphite.

17. The process of claim 1 , wherein the carbonaceous material has a BET specific surface area of at least about 20 m 2 /g.

18. The process of claim 1 , wherein the carbonaceous material has a BET specific surface area in the range of from about 20 m 2 /g to about 500 m 2 /g.

19. The process of claim 1 , wherein the porous, shaped metal-carbon product is a carbonized product of a carbonaceous material with water, a water-soluble organic binder, and a metal precursor of the metal component selected from the group consisting of a metal carbonate, a metal oxide, a metal hydroxide, a salt of a metal acid, a heteropoly acid, a metal carboxylate, a metal carbide, a metal chloride, a metal amine complex-containing compound, a hydrate thereof, and a mixture of any two or more thereof.

20. The process of claim 19 , wherein the water-soluble binder comprises a cellulose and/or a sugar.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 22, 2019
From: RENNOVIA INC.
To: RENNOVIA (ASSIGNMENT FOR THE BENEFIT OF CREDITORS), LLC
Reel/Frame 051097/0542 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2019
From: SOKOLOVSKII, VALERY; HAGEMEYER, ALFRED; SHOEMAKER, JAMES A.W.; GÜRBÜZ, ELIF ISPIR; ZHU, GUANG; DIAS, ERIC L.
To: RENNOVIA INC.
Reel/Frame 051038/0697 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2019
From: RENNOVIA LLC
To: ARCHER-DANIELS-MIDLAND COMPANY
Reel/Frame 051038/0862 →
Continuity (3)
Division 15132048 · Apr 18, 2016
Provisional Application 62247727 · Oct 28, 2015
Related Publication 20200055029A1 · Feb 20, 2020