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

Patent metadata

Field	Value
Publication number	US-10053438-B2
Application number	US-201615542917-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 iso-butane to provide a stream comprising iso-butene and hydrogen and separating this stream into a stream consisting essentially of hydrogen 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; reacting a part or all of the stream consisting essentially of hydrogen with oxygen, providing a stream comprising hydrogen peroxide; and reacting a part or all of the stream comprising hydrogen peroxide with propene 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 S1 comprising iso-butane, to provide a stream, S2, comprising iso-butene and hydrogen;
b) a separation step separating stream S2 into a stream, S3, consisting essentially of hydrogen and a stream, S4, comprising iso-butene;
c) a step of reacting a part or all of stream S4 with an alkanol in the presence of a solid acid catalyst, to provide a stream, S5, comprising an alkyl tert-butyl ether;
d) a separation step separating the alkyl tert-butyl ether from stream S5;
e) a step of reacting a part or all of stream S3 with oxygen, to provide a stream, S6, comprising hydrogen peroxide;
f) a step of reacting a part or all of stream S6 with propene in the presence of an epoxidation catalyst, to provide a stream, S7, comprising propene oxide; and
g) a separation step separating propene oxide from stream S7.

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

3. The process of claim 1 , wherein a stream, S8, comprising unreacted iso-butane is separated in step d), a stream S9 comprising more than 80% by weight iso-butane is separated from stream S8 and stream S9 is recycled to step a).

4. The process of claim 1 , wherein the feed stream S1 of step a) comprises n-butane, a stream, S8, comprising 1-butene is separated in step d) and a stream, S10, consisting essentially of 1-butene is separated from said stream S8.

5. The process of claim 1 , wherein the feed stream S1 to step a) comprises n-butane and wherein 1,3-butadiene is removed from stream S4 before reacting it in step c).

6. The process of claim 1 , comprising an additional step of isomerizing n-butane to iso-butane, to provide the feed stream S1 to step a).

7. The process of claim 1 , wherein step e) is carried out as an anthraquinone process providing a 20 to 75% by weight aqueous solution of hydrogen peroxide as stream S6.

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

9. The process of claim 1 , wherein additional hydrogen is fed to step e).

10. An integrated process for making propene oxide and methyl tert-butyl ether, comprising:
a) a step of dehydrogenating a feed stream, S1, comprising iso-butane, to provide a stream, S2, comprising iso-butene and hydrogen;
b) a separation step separating stream S2 into a stream, S3, consisting essentially of hydrogen and a stream, S4, comprising iso-butene;
c) a step of reacting a part or all of stream S4 with methanol in the presence of a solid acid catalyst, to provide a stream, S5, comprising methyl tert-butyl ether;
d) a separation step separating methyl tert-butyl ether from stream S5;
e) a step of reacting a part or all of stream S3 with oxygen in an anthraquinone process, to provide a stream, S6, comprising hydrogen peroxide as a 20 to 75% by weight aqueous solution of hydrogen peroxide;
f) a step of reacting a part or all of stream S6 with propene in the presence of an epoxidation catalyst, to provide a stream, S7, comprising propene oxide; and
g) a separation step separating propene oxide from stream S7.

11. The process of claim 10 , wherein a titanium silicalite catalyst is used as epoxidation catalyst in step f).

12. The process of claim 10 , wherein the feed stream S1 to step a) comprises n-butane, a stream, S8, comprising 1-butene is separated in step d) and a stream, S10, consisting essentially of 1-butene is separated from said stream S8.

13. The process of claim 12 , wherein 1,3-butadiene is removed from stream S4 before reacting it in step c).

Assignees

• Evonik Degussa Gmbh
• Thyssenkrupp Ind Solutions Ag

Inventors

• Bolz David
• Wiederhold Holger

Classifications

• C01B15/029

  Preparation from hydrogen and oxygen · CPC title

• C07C41/34

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07D301/12 Primary

  with hydrogen peroxide or inorganic peroxides or peracids · CPC title

• C07C41/09

  by dehydration of compounds containing hydroxy groups · CPC title

• C07C5/333

  Catalytic processes · CPC title