IP Library Granted Patent US 9,045,385
Granted Patent B2
US 9,045,385 · App. 14/569,022 · Granted Jun 2, 2015

Conversion of propane to propylene

Inventors: Vivek Julka (Fishkill, NY); Sagar Gadewar (Santa Barbara, CA); Peter K. Stoimenov (Santa Barbara, CA); Philip Grosso (Aubum, CA); Jeffrey H. Sherman (Vero Beach, FL); Aihua Zhang (Santa Barbara, CA); Eric W. McFarland (Santa Barbara, CA)
Assignee: REACTION 35, LLC
C07C1/30C07C2521/08C07C2521/04C07C2523/44
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Quick Facts
Patent No.
US 9,045,385
App. No.
14/569,022
Granted
Jun 2, 2015
Kind
B2
Abstract

A process is disclosed that includes brominating a C 2 , C 3 , C 4 , C 5 or C 6 alkane with elemental bromine to form a bromo-alkane. The bromo-alkane is reacted to form a C 2 , C 3 , C 4 , C 5 or C 6 alkene and HBr. The HBr is oxidized to form elemental bromine.

Claims (38)

1. A process comprising:

brominating an alkane with elemental bromine to form a stream comprising bromo-alkane and dibromo-alkane, wherein the alkane is a C 2 , C 3 , C 4 , C 5 , or C 6 alkane;

separating the dibromoalkane from the bromo-alkane,

reacting the dibromoalkane, thermally or in the presence of a catalyst, with alkane to form additional bromo-alkane;

reacting the additional bromo-alkane to form a corresponding alkene of the alkane and HBr; and oxidizing the HBr to form elemental bromine.

2. The process of claim 1 , wherein the alkane is ethane, propane, n-butane, isobutane, a pentane, or a hexane.

3. The process of claim 2 , wherein the alkane is propane and the alkene is propylene.

4. A process comprising:

providing a feedstock comprising propane;

reacting at least some of the propane with bromine to form bromopropane, dibromopropane, and HBr;

separating the dibromopropane from the bromopropane,

reacting the dibromopropane, thermally or in the presence of a catalyst, with alkane to form additional bromopropane;

dehydrobrominating the additional bromopropane to form a propylene/HBrpropylene and HBr mixture;

separating the propylene/HBrpropylene and HBr mixture to form propylene and recycle HBr;

oxidizing the recycle HBr to form a bromine/waterbromine and water mixture;

and separating bromine from the bromine/waterbromine and water mixture.

5. The process of claim 4 , wherein the step of reacting at least some of the propane with bromine is thermally induced.

6. The process of claim 5 , wherein the reaction occurs at a temperature of at least 200° C.

7. The process of claim 4 , wherein the dehydrobrominating step takes place in the presence of a catalyst.

8. The process of claim 7 , wherein the catalyst is selected from the group consisting of a silica-based catalyst, titanium dioxide, zirconium dioxide and their mixtures thereof.

9. The process of claim 7 , wherein in the dehydrobrominating step, the bromopropane is heated to between 250° C. and 500° C.

10. The process of claim 4 , wherein separating the propylene and HBr mixture is accomplished by distillation.

11. The process of claim 4 , wherein separating the propylene and HBr mixture is accomplished by absorbing the HBr in aqueous HBr to form a concentrated HBr solution.

12. The process of claim 11 , further comprising after the step of absorbing the HBr in aqueous HBr to form a concentrated HBr solution:

stripping the HBr from the concentrated aqueous HBr.

13. The process of claim 4 , wherein the HBr is oxidized using a chromium or cerium-based catalyst.

14. The process of claim 4 , further comprising after the step of separating bromine from the propylene and HBr mixture:

recycling the bromine to react with the propane in the step of reacting at least some of the propane with bromine.

15. The process of claim 1 , wherein the alkane is propane, the bromo-alkane is bromopropane, the dibromo-alkane is dibromopropane, and the alkene is propylene, and wherein the process further comprises converting the dibromopropane directly to propylene using Zn, wherein ZnBr 2 is produced as a byproduct.

16. The process of claim 15 , further comprising using oxidation or electrolysis and the ZnBr 2 to regenerate Br 2 .

17. A process comprising:

brominating an alkane with elemental bromine in a bromination reactor to form a stream comprising bromo-alkane and dibromo-alkane, wherein the alkane is a C2, C3, C4, C5 or C6 alkane;

separating the dibromoalkane from the bromo-alkane,

reacting the dibromoalkane, thermally or in the presence of a catalyst, with alkane to form additional bromo-alkane;

reacting the additional bromo-alkane to form a corresponding alkene of the alkane and HBr;

and oxidizing the HBr to form elemental bromine.

18. The process of claim 17 , wherein the dibromo-alkane is recycled to the bromination reactor for the reacting of the dibromo-alkane with the alkane to form bromo-alkane.

19. The process of claim 17 , wherein the reacting of the dibromo-alkane with the alkane to form bromo-alkane occurs in a separate reactor from the bromination reactor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2015
From: JULKA, VIVEK; GADEWAR, SAGAR; STOIMENOV, PETER K.; GROSSO, PHILIP; SHERMAN, JEFFREY H.; ZHANG, AIHUA; MCFARLAND, ERIC
To: GRT, INC.
Reel/Frame 035998/0651 →
Continuity (3)
Continuation 13479085 · May 23, 2012
Provisional Application 61489234 · May 23, 2011
Related Publication 20150099911A1 · Apr 9, 2015