IP Library Granted Patent US 8,846,994
Granted Patent B2
US 8,846,994 · App. 13/381,735 · Granted Sep 30, 2014

Method for producing low-odor n-butane

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Quick Facts
Patent No.
US 8,846,994
App. No.
13/381,735
Granted
Sep 30, 2014
Kind
B2
Abstract

The invention relates to a method for producing low-odor n-butane by catalytic hydrogenation of a feed mixture. The aim of the invention is to provide such a method, wherein the feed material, in addition to n-butane, n-butene and up to 1 mass % formic acid and/or up to 1 mass % pentanals and/or up to 0.5 mass % pentanols, also comprises carbon monoxide. The aim is achieved by treating the feed mixture in the temperature range of 15 to 120° C. with an aqueous solution of an alkali metal or alkaline earth metal hydroxide in the concentration range of 0.5 to 30 mass % and subsequently subjecting the feed mixture to the catalytic hydrogenation.

Claims (42)

1. A process for preparing low-odor n-butane, the process comprising:

mixing a n-butane feedstock with an aqueous solution comprising an alkali metal hydroxide or an alkaline earth metal hydroxide to obtain a biphasic mixture; allowing the biphasic mixture to separate into an aqueous phase comprising a formate salt of the alkali metal or alkaline earth metal and an n-butane phase consisting essentially of n-butane, n-butenes and water;

separating the aqueous phase from the n-butane phase;

removing the water from the n-butane phase to obtain an anhydrous mixture of n-butane and n-butenes; and

catalytically hydrogenating the anhydrous mixture to obtain the low odor n-butane;

wherein

a temperature of the biphasic mixture is from 15 to 120° C., and

wherein

the n-butane feedstock comprises n-butene, carbon monoxide, and formic acid in a content of from 0.001 to 1% by mass, and

a content of the alkali metal hydroxide or alkaline earth metal hydroxide in the aqueous solution is from 0.5 to 30% by mass.

2. The process of claim 1 ,

wherein the aqueous solution comprises sodium hydroxide in a concentration of from 0.5 to 2.5% by mass.

3. The process of claim 1 ,

wherein a pressure of the mixing and separation is from 0.5 to 5 MPa.

4. The process of claim 1 ,

wherein a proportion of carbon monoxide in the n-butane feedstock is from 1 to 10% by mass.

5. The process of claim 1 ,

wherein the n-butane feedstock further comprises hydrogen.

6. The process of claim 1 ,

wherein the mixing and separation comprises extracting in a mixer-settler unit.

7. The process of claim 6 ,

wherein the mixer-settler unit is a static mixer.

8. The process of claim 6 ,

wherein the mixer-settler unit is a pump.

9. The process of claim 1 ,

wherein the mixing and separation comprises extracting in an extraction column.

10. The process of claim 1 ,

wherein the extracted mixture is entirely or partly liquid.

11. The process of claim 1 ,

wherein catalytically hydrogenating the anhydrous mixture comprises hydrogenating in a liquid phase over a palladium catalyst at a temperature of from 20 to 140° C. and at a pressure of from 0.6 to 3 MPa.

12. The process of claim 1 , wherein removing the water comprises distillation.

13. The process of claim 1 ,

further comprising dewatering the low odor n-butane by distillation, to obtain a dewatered output.

14. The process of claim 1 ,

further comprising removing C 5 hydrocarbons from the n-butane phase or the low-odor n-butane by distillation.

15. The process of claim 1 ,

wherein the n-butane feedstock is a stream from a C 4 hydroformylation.

16. The process of claim 4 , wherein the proportion of carbon monoxide in the n-butane feedstock is from 2 to 7% by mass.

17. The process of claim 8 , wherein the mixer-settler unit is a centrifugal pump.

18. The process of claim 1 , wherein a content of linear butane in the n-butane feedstock is below 30% by mass.

19. The process of claim 1 , wherein the aqueous solution is a sodium hydroxide solution, a potassium hydroxide solution, or both.

20. The process of claim 13 , further comprising removing C 5 hydrocarbons from the low-odor n-butane or the dewatered output by distillation.

Assignments (2)
MERGER Recorded May 15, 2014
From: EVONIK OXENO GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032900/0785 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2012
From: LUEKEN, HANS-GERD; KAIZIK, ALFRED; WINTERBERG, MARKUS; BUESCHKEN, WILFRIED; FRIDAG, DIRK
To: EVONIK OXENO GMBH
Reel/Frame 027742/0009 →