IP Library Granted Patent US 10,053,440
Granted Patent B2
US 10,053,440 · App. 15/542,923 · Granted Aug 21, 2018

Integrated process for making propene oxide and an alkyl tert-butyl ether

Inventors: David Bolz (Frankfurt, DE); Holger Wiederhold (Darmstadt, DE)
Assignees: EVONIK DEGUSSA GMBH; THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
C07D301/19B01J21/063C01B15/023C07C5/32C07C41/06C07C43/046
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,053,440
App. No.
15/542,923
Granted
Aug 21, 2018
Kind
B2
Abstract

An integrated process for making propene oxide and an alkyl tert-butyl ether comprises dehydrogenating a feed stream comprising propane and iso-butane to provide a stream comprising propene, iso-butene and hydrogen; separating this stream into a stream consisting essentially of hydrogen and a stream comprising propene and iso-butene; separating the stream comprising propene and iso-butene into a stream comprising propene and a stream comprising iso-butene; reacting a part or all of the stream comprising iso-butene with an alkanol in the presence of a solid acid catalyst to provide an alkyl tert-butyl ether; and reacting a part or all of the stream comprising propene with hydrogen peroxide in the presence of an epoxidation catalyst to provide propene oxide.

Claims (43)

1. An integrated process for making propene oxide and an alkyl tert-butyl ether comprising;

a) a step of dehydrogenating a feed stream, S 1 , comprising propane and iso-butane, to provide a stream, S 2 , comprising propene, iso-butene and hydrogen;

b) a separation step separating stream S 2 into a stream, S 3 , consisting essentially of hydrogen and a stream, S 4 , comprising propene and iso-butene;

c) a separation step separating stream S 4 into a stream, S 5 , comprising propene and a stream, S 6 , comprising iso-butene;

d) a step of reacting a part or all of stream S 5 with hydrogen peroxide in the presence of an epoxidation catalyst to provide a stream, S 7 , comprising propene oxide;

e) a separation step separating propene oxide from stream S 7 ;

f) a step of reacting a part or all of stream S 6 with an alkanol in the presence of a solid acid catalyst, to provide a stream, S 8 , comprising an alkyl tert-butyl ether; and

g) a separation step separating the alkyl tert-butyl ether from stream S 8 .

2. The process of claim 1 , wherein the alkanol is methanol.

3. The process of claim 1 , wherein unreacted propane is separated from stream S 5 and recycled as a stream, S 9 , to step a) before stream S 5 is reacted in step d).

4. The process of claim 1 , wherein a stream, S 10 , comprising unreacted iso-butane is separated in step g), a stream, S 11 , comprising more than 80% by weight iso-butane is separated from said stream S 10 and said stream S 11 is recycled to step a).

5. The process of claim 1 , wherein the feed stream S 1 to step a) comprises n-butane, a stream, S 10 , comprising 1-butene is separated in step g) and a stream, S 12 , consisting essentially of 1-butene is separated from said stream S 10 .

6. The process of claim 1 , wherein the feed stream S 1 to step a) comprises n-butane and wherein 1,3-butadiene is removed from stream S 6 before reacting it in step f).

7. The process of claim 1 , comprising the additional steps:

h) separating a feed stream comprising propane and n-butane into a stream, S 13 , comprising propane and a stream, S 14 , comprising n-butane;

i) subjecting stream S 14 to an isomerization reaction to provide a stream, S 15 , comprising n-butane and iso-butane; and

j) combining the iso-butane of stream S 15 with a part or all of stream S 13 to give feed stream S 1 to step a).

8. The process of claim 7 , wherein n-butane is separated from stream S 15 and is recycled as stream S 16 to said isomerization reaction before combining the iso-butane of stream S 15 with a part or all of stream S 13 .

9. The process of claim 1 , wherein a titanium silicalite catalyst is used as epoxidation catalyst in step d).

10. An integrated process for making propene oxide and methyl tert-butyl ether comprising:

a) a step of dehydrogenating a feed stream, S 1 , comprising propane and iso-butane, to provide a stream, S 2 , comprising propene, iso-butene and hydrogen;

b) a separation step separating stream S 2 into a stream, S 3 , consisting essentially of hydrogen and a stream, S 4 , comprising propene and iso-butene;

c) a separation step separating stream S 4 into a stream S 5 comprising propene and a stream, S 6 , comprising iso-butene;

d) a step of reacting a part or all of stream S 5 with hydrogen peroxide in the presence of an epoxidation catalyst, providing a stream, S 7 , comprising propene oxide;

e) a separation step separating propene oxide from stream S 7 ;

f) a step of reacting a part or all of stream S 6 with methanol in the presence of a solid acid catalyst, providing a stream, S 8 , comprising methyl tert-butyl ether; and

g) a separation step separating the methyl tert-butyl ether from stream S 8 .

11. The process of claim 10 , wherein unreacted propane is separated from stream S 5 and recycled as a stream, S 9 , to step a) before stream S 5 is reacted in step d).

12. The process of claim 11 , wherein a stream, S 10 , comprising unreacted iso-butane is separated in step g), a stream, S 11 , comprising more than 80% by weight iso-butane is separated from stream S 10 , and stream S 11 is recycled to step a).

13. The process of claim 11 , wherein the feed stream S 1 to step a) comprises n-butane, a stream, S 10 , comprising 1-butene is separated in step g) and a stream, S 12 , consisting essentially of 1-butene, is separated from stream S 10 .

14. The process of claim 13 , wherein 1,3-butadiene is removed from stream S 6 before reacting it in step f).

15. The process of claim 11 , wherein a titanium silicalite catalyst is used as epoxidation catalyst in step d).

16. An integrated process for making propene oxide and an alkyl tert-butyl ether, comprising:

a) a step of dehydrogenating a feed stream, S 1 , comprising propane, n-butane and iso-butane, to provide a stream, S 2 , comprising propene, 1-butene, iso-butene and hydrogen;

b) a separation step separating stream S 2 into a stream, S 3 , consisting essentially of hydrogen and a stream, S 4 , comprising propene, 1-butene and iso-butene;

c) a separation step separating stream S 4 into a stream, S 5 , comprising propene and a stream, S 6 , comprising 1-butene and iso-butene;

d) a separation step separating unreacted propane from stream S 5 and recycling it as a stream, S 9 to step a);

e) a step of reacting a part or all of stream S 5 from which propane has been separated in step d) with hydrogen peroxide in the presence of an epoxidation catalyst, to provide a stream, S 7 , comprising propene oxide;

f) a separation step separating propene oxide from stream S 7 ;

g) a step of reacting a part or all of stream S 6 with an alkanol in the presence of a solid acid catalyst, to provide a stream, S 8 , comprising an alkyl tert-butyl ether;

h) a separation step separating the alkyl tert-butyl ether and a stream, S 10 , comprising 1-butene from stream S 8 ; and

i) a separation step separating a stream S 12 consisting essentially of 1-butene from stream S 10 .

17. The process of claim 16 , wherein 1,3-butadiene is removed from stream S 6 before reacting it in step g).

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2024
From: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
To: THYSSENKRUPP UHDE GMBH
Reel/Frame 068466/0185 →
CHANGE OF NAME Recorded Jan 10, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051621/0907 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2017
From: BOLZ, DAVID; WIEDERHOLD, HOLGER
To: EVONIK DEGUSSA GMBH
Reel/Frame 043100/0723 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2017
From: EVONIK DEGUSSA GMBH
To: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
Reel/Frame 043101/0055 →
Priority Claims (1)
EP 15151050 · Jan 14, 2015 · regional
Continuity (1)
Related Publication 20180002300A1 · Jan 4, 2018
Cited By (2)
US 12,240,793 US 12,623,987