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

Patent metadata

Field	Value
Publication number	US-10053440-B2
Application number	US-201615542923-A
Country	US
Kind code	B2
Filing date	Jan 8, 2016
Priority date	Jan 14, 2015
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

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.

First claim

The invention claimed is:

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).

Assignees

• Evonik Degussa Gmbh
• Thyssenkrupp Ind Solutions Ag

Inventors

• Bolz David
• Wiederhold Holger

Classifications

• C07D301/19 Primary

  with organic hydroperoxides · CPC title

• C07C43/046

  Alkyl tert-alkyl ether, e.g. CH3OC(CH3)3 · CPC title

• C07C41/06

  by addition of organic compounds only · CPC title

• C07C5/32

  by dehydrogenation with formation of free hydrogen · CPC title

• B01J21/063

  Titanium; Oxides or hydroxides thereof · CPC title