IP Library Granted Patent US 10,000,448
Granted Patent B2
US 10,000,448 · App. 15/124,397 · Granted Jun 19, 2018

Catalysts, methods, and systems for preparing carbamates

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Quick Facts
Patent No.
US 10,000,448
App. No.
15/124,397
Granted
Jun 19, 2018
Kind
B2
Abstract

Methods, systems and kits for preparing carbamates as well as catalysts for preparing the carbamates, are disclosed. The methods for preparing carbamate can include providing a catalyst comprising cerium oxide (CeO2) and at least one metal selected from the group consisting of iron (Fe), manganese (Mn), titanium (Ti), cobalt (Co), aluminum (Al), zinc (Zn), calcium (Ca), tin (Sn), indium (In), and any combination thereof; contacting the catalyst with at least one amine and at least one alcohol to form a mixture; and contacting the mixture with carbon dioxide under conditions sufficient to form the carbamate.

Claims (17)

1. A catalyst comprising cerium oxide (CeO 2 ) and aluminum (Al) comprising formula Ce x Al y O 2 , wherein the catalyst is a calcined catalyst, and wherein x is 0.966 and y is 0.033.

2. The catalyst of claim 1 , wherein the catalyst is a heterogeneous catalyst.

3. A method of preparing a carbamate, the method comprising:

contacting a catalyst with at least one amine and at least one alcohol to form a mixture; and

contacting the mixture with carbon dioxide under conditions sufficient to form the carbamate,

wherein the catalyst comprises cerium oxide (CeO 2 ) and aluminum (Al) comprising formula Ce x Al y O 2 , wherein the catalyst is a calcined catalyst, and wherein x is 0.966 and y is 0.033.

4. The method of claim 3 , wherein the at least one alcohol comprises methanol, ethanol, propanol, butanol, n-hexanol, or a combination of any two or more thereof.

5. The method of claim 3 , wherein the at least one amine comprises at least one aliphatic amine.

6. The method of claim 5 , wherein the at least one aliphatic amine comprises methylamine, ethylamine, n-propylamine, n-butylamine, n-hexylamine, n-octylamine, or a combination of any two or more thereof.

7. The method of claim 3 , wherein the at least one amine comprises at least one aromatic amine.

8. The method of claim 7 , wherein the at least one aromatic amine comprises benzylamine.

9. The method of claim 3 , wherein a molar ratio of the at least one amine to the at least one alcohol in the mixture is about 1:40 to about 1:200.

10. The method of claim 3 , wherein a molar ratio of the at least one amine to the at least one alcohol in the mixture is about 1:100.

11. The method of claim 3 , wherein contacting the mixture with the carbon dioxide comprises heating the mixture and the carbon dioxide at a temperature of about 160° C. to about 180° C.

12. The method of claim 3 , wherein contacting the mixture with the carbon dioxide comprises heating the mixture and the carbon dioxide at a pressure of about 4.0 MPa to about 7.0 MPa.

13. The method of claim 3 , wherein contacting the mixture with the carbon dioxide comprises heating the mixture and the carbon dioxide for about 2 hours to about 16 hours.

14. The catalyst of claim 1 , wherein the catalyst further comprises at least one metal selected from the group consisting of iron (Fe), manganese (Mn), titanium (Ti), cobalt (Co), zinc (Zn), calcium (Ca), tin (Sn), indium (In), and a combination of any two or more thereof.

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Jul 31, 2019
From: CRESTLINE DIRECT FINANCE, L.P.
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 049924/0794 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 14, 2016
From: HOU, ZHENSHAN; ZHANG, RAN
To: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
Reel/Frame 039736/0183 →