Process for producing high purity 1-butene

Patent metadata

Field	Value
Publication number	US-11407697-B2
Application number	US-202017603241-A
Country	US
Kind code	B2
Filing date	Apr 28, 2020
Priority date	May 31, 2019
Publication date	Aug 9, 2022
Grant date	Aug 9, 2022

Abstract

Methods of and systems for producing an olefin are disclosed. A paraffin is dehydrogenated to produce a mixture comprising the olefin and unreacted paraffin. The mixture is then fed to an extractive distillation unit that uses soybean oil as a solvent to extract at least some n-butane from the mixture.

First claim

The invention claimed is:

1. A method comprising:
providing a mixture comprising an olefin and a paraffin; and
contacting the mixture with soybean oil under conditions such that the paraffin dissolves in the soybean oil at a higher rate than the olefin to form (1) a first stream comprising the soybean oil and at least some of the paraffin of the mixture and (2) a second stream comprising primarily the olefin.

2. A method of producing a first olefin, the method comprising:
dehydrogenating a paraffin to produce a mixture comprising the first olefin and unreacted paraffin; and
contacting the mixture with soybean oil under conditions such that the unreacted paraffin dissolves in the soybean oil at a higher rate than the first olefin to form (1) a first stream comprising the soybean oil and at least some of the unreacted paraffin of the mixture and (2) a second stream comprising primarily the first olefin.

3. The method of claim 2 , wherein the dehydrogenating step produces the first olefin and a second olefin as isomers, and the method further comprises, prior to the contacting step, isomerizing the second olefin to produce an additional amount of the first olefin in the mixture.

4. The method of claim 1 , wherein the contacting step is performed in an extractive distillation column.

5. The method of claim 1 , wherein the first stream comprises at least 50 wt. % of the paraffin of the mixture.

6. The method of claim 1 , wherein the conditions comprise an operating temperature in a range of 10 to 50° C.

7. A method of producing 1-butene, the method comprising:
dehydrogenating, in a dehydrogenation zone, n-butane to produce a first mixture comprising 1-butene, 2-butene, isobutene, and unreacted n-butane;
processing, in an isomerization zone, the first mixture under isomerization conditions sufficient to isomerize 2-butene to form 1-butene;
contacting an effluent of the isomerization zone with soybean oil in an extractive distillation unit under extractive distillation conditions such that the unreacted n-butane dissolves in the soybean oil at a higher rate than the 1-butene and the isobutene to form (1) a first stream comprising the soybean oil and at least some of the unreacted n-butane and (2) a second stream comprising primarily 1-butene and isobutene; and
separating the second stream to produce a third stream comprising primarily 1-butene.

8. The method of claim 7 , wherein the first stream comprises at least 50 wt. % of the unreacted n-butane.

9. The method of claim 7 , wherein the effluent of the isomerization zone comprises less than 0.1 wt. % 2-butene.

10. The method of claim 7 , wherein the extractive distillation conditions include an operating temperature of 10 to 50° C. and an operating pressure of 3 to 5 bar.

11. The method of claim 7 , wherein the second stream further comprises n-butane and 2-butene and the separating further produces a fourth stream comprising primarily isobutene, and a fifth stream comprising primarily n-butane.

12. The method of claim 11 , wherein the fifth stream further comprises less than 40 to 50 wt. % 2-butene.

13. The method of claim 12 , wherein the separating comprises:
distilling the second stream in a first distillation column to produce the fifth stream comprising n-butane and less than 40 to 50 wt. % 2-butene and a sixth stream comprising primarily 1-butene and isobutene, collectively;
distilling the sixth stream to produce the third stream comprising primarily 1-butene and fourth stream comprising primarily isobutene.

14. The method of claim 7 , wherein the third stream comprises 99 to 99.9 wt. % 1-butene.

15. The method of claim 7 , further comprising cooling the effluent of the isomerization zone before the contacting step.

16. The method of claim 7 , further comprising:
degassing the first stream to produce a recycle soybean oil stream and a recycle n-butane stream; and
recycling the recycle soy bean oil stream to the extractive distillation unit for extracting n-butane;
recycling the recycle n-butane stream to the dehydrogenation zone.

Assignees

• Sabic Global Technologies Bv

Inventors

• Haider Muhammad H
• Al-Zahrani Abdulaziz
• Chang Te

Classifications

• C07C7/08 Primary

  by extractive distillation · CPC title

• C07C5/2512

  with metal oxides · CPC title

• C07C5/3335

  with metals · CPC title

• C07C5/3337

  of the platinum group · CPC title

• C07C5/373

  with simultaneous isomerisation · CPC title