Integrated process for production of glycerol carbonate (4-hydroxymethyl-2-oxo-1, 3-dioxolane) and urea

Patent metadata

Field	Value
Publication number	US-11578034-B2
Application number	US-201816496497-A
Country	US
Kind code	B2
Filing date	Mar 7, 2018
Priority date	Apr 11, 2017
Publication date	Feb 14, 2023
Grant date	Feb 14, 2023

Abstract

Systems and methods for integrated glycerol carbonate and/or urea production. This disclosure pertains to development of a process for production of glycerol carbonate and/or urea from ammonia, carbon dioxide and glycerol. The process integrates glycerol carbonate production into a urea production process. The urea produced in the production facility may be used to produce glycerol carbonate by reacting urea with glycerol. The ammonia generated by glycerol carbonate production may be recycled back to urea production. Unreacted urea from the glycerol carbonate production may be separated and recycled to the urea product stream. The systems and methods can reduce the cost for urea production and increase product value of the excessive glycerol produced from other chemical plants.

First claim

The invention claimed is:

1. A method of producing glycerol carbonate and/or urea, the method comprising steps as follows:
(1) reacting carbon dioxide and ammonia to produce a first product stream comprising ammonium carbamate, unreacted ammonia, water and the urea;
(2) heating the first product stream to decompose the ammonium carbamate to form a first decomposition product stream comprising ammonia and carbon dioxide, and a second product stream comprising urea and water;
(3) subjecting the second product stream to a concentration process to produce a third product stream comprising concentrated urea;
(4) subjecting the third product stream comprising the concentrated urea to a granulation process to produce granulated urea;
(5) reacting at least some of the granulated urea with glycerol to form glycerol carbamate and ammonia;
(6) decomposing the glycerol carbamate to form the glycerol carbonate and ammonia;
(7) feeding at least some of the ammonia from step (5) and/or step (6) to step (1) for the reacting to form the first product stream;
(8) transferring any unreacted granulated urea from step (5) to a urea product stream; and
(9) flowing the glycerol carbonate from step (6) in a glycerol carbonate product stream;
wherein the steps (5) and (6) comprise contacting the urea with the glycerol over a catalyst under reaction conditions sufficient to form the glycerol carbonate; and
wherein the reaction conditions in step (5) comprise a reaction temperature in a range of 90° C. to 220° C. and a reaction pressure in a range of 2.0×10 −3 to 2.0×10 −1 MPa; and wherein the method is an integrated method for the production of glycerol carbonate and/or urea;
wherein the catalyst comprises a metal as a catalytically active species; and
wherein the metal is a single member selected from the group consisting of Zn++, Mg++, Mn++, Fe++, Ni++, Cd++, Ca++ and Li+, or is a combination of any two or more of Zn++, Mg++, Mn++, Fe++, Ni++, Cd++, Ca++ and Li+.

2. The method of claim 1 , wherein the metal is Mg++.

3. The method of claim 1 , wherein the metal is Mn++.

4. The method of claim 1 , wherein the metal is Fe++.

5. The method of claim 1 , wherein the metal is Ni++.

6. The method of claim 1 , wherein the metal is Li+.

7. A method of producing glycerol carbonate and/or urea, the method comprising steps as follows:
(1) employing carbon dioxide and ammonia in synthesizing the urea;
(2) reacting at least some of the urea with glycerol to form glycerol carbamate and ammonia;
(3) decomposing the glycerol carbamate to form the glycerol carbonate and ammonia;
(4) feeding at least some of the ammonia from step (2) and/or step (3) to step (1) for the synthesizing;
(5) transferring any unreacted urea from step (2) to a urea product stream; and
(6) flowing the glycerol carbonate from step (3) in a glycerol carbonate product stream;
wherein the urea and glycerol in step (2) reacts in a solvent;
wherein the steps (2) and (3) comprise contacting the urea with the glycerol over a catalyst under reaction conditions sufficient to form the glycerol carbonate; and
wherein the reaction conditions comprise a reaction temperature in a range of 90° C. to 220° C. and a reaction pressure in a range of 2.0×10 −3 to 2.0×10 −1 MPa;
wherein the method is an integrated method for glycerol carbonate and/or urea; and
wherein the solvent is selected from the group consisting of dichloromethane, nitro-benzene, methanol, and combinations thereof.

8. The method of claim 2 , wherein the metal consists of Zn++.

9. The method of claim 1 , wherein the reaction conditions comprise a reaction temperature in a range of 190° C. to 220° C.

10. The method of claim 7 , wherein the solvent is dichloromethane, methanol, or a combination thereof.

11. A method for producing glycerol carbonate, the method comprising steps of:
loading granulated urea into a reaction vessel via a solid loading conveyor connected to the reaction vessel, wherein the reaction vessel contains glycerol, to form a reaction mixture;
agitating and thermally treating the reaction mixture in the reaction vessel to produce a product stream comprising the glycerol carbonate, unreacted urea and glycerol carbamate;
feeding the product stream to a solids removal filtration facility; and
collecting the glycerol carbonate in a storage tank or recycling the glycerol carbonate to the reaction vessel.

12. The method of claim 11 , wherein a solvent, a catalyst or both are added to the reaction vessel.

13. The method of claim 11 , wherein product stream is fed through a solids removal filtration facility.

14. The method of claim 11 , wherein ammonia produced in the reaction vessel is removed from the reaction vessel via a vacuum pump.

15. The method of claim 14 , wherein a condenser is installed before the vacuum pump to condense glycerol carbonate vapor drawn by the vacuum pump.

16. The method of claim 14 , wherein the ammonia is scrubbed in a water scrubber.

Assignees

• Sabic Global Technologies Bv

Inventors

• Ansari Mohammed Bismillah
• Bodas Vijay Dinkar
• Leal Guillermo

Classifications

• C07C273/14

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C273/04 Primary

  from carbon dioxide and ammonia · CPC title

• C07D317/36 Primary

  Alkylene carbonates; Substituted alkylene carbonates · CPC title

• C01C1/086

  from urea · CPC title

• Y02P20/10

  Process efficiency · CPC title