IP Library Granted Patent US 8,822,709
Granted Patent B2
US 8,822,709 · App. 13/653,135 · Granted Sep 2, 2014

Process for preparing an epoxide from an oxygenate

Inventors: Leslie Andrew Chewter (Amsterdam, NL); Hervé Henry (Rotterdam, NL); Pieter Oldenhove (Amsterdam, NL); Rajaram Ramesh (Amserdam, NL); Jeroen Van Westrenen (Amsterdam, NL)
Assignee: Shell Oil Company
C07D301/19
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Quick Facts
Patent No.
US 8,822,709
App. No.
13/653,135
Granted
Sep 2, 2014
Kind
B2
Abstract

The invention relates to an integrated process for preparing an epoxide from an oxygenate, wherein the oxygenate is converted into a lower olefin and the lower olefin is subsequently epoxidised, and wherein isobutane obtained after hydrogenation and subsequent normal/iso separation of C4 hydrocarbons obtained as by-product of the oxygenate conversion, is converted into a hydroperoxide that is used for the conversion of the lower olefin into the corresponding epoxide.

Claims (20)

1. A process for preparing an epoxide from an oxygenate, the process comprising the following steps:

a) contacting the oxygenate with a molecular sieve-comprising catalyst, at a temperature in the range of from 350 to 1000° C. to obtain an olefinic product stream comprising ethylene, propylene and C4 hydrocarbons;

b) separating ethylene and/or propylene and a fraction comprising C4 hydrocarbons including normal butane, isobutane, normal butene and isobutene, from the olefinic product stream;

c) hydrogenating at least part of the fraction comprising C4 hydrocarbons in a hydrogenation unit to obtain a saturated C4 hydrocarbon stream;

d) separating the saturated C4 hydrocarbon stream into a stream enriched in normal butane and a stream enriched in isobutane;

e) oxidizing the isobutane in the stream enriched in isobutane into tertiary butyl hydroperoxide; and

f) reacting tertiary butyl hydroperoxide obtained in step d) with ethylene and/or propylene separated from the olefinic product stream obtained in step a) to obtain the epoxide and tertiary butanol.

2. A process according to claim 1 , wherein the molecular sieve-containing catalyst is a zeolite-comprising catalyst.

3. A process according to claim 2 , wherein the zeolite-comprising catalyst comprises at least one zeolite selected from MFI, MEL, TON and MTT zeolites.

4. A process according to claim 3 , wherein the zeolite-comprising catalyst comprises at least one of ZSM-5, ZSM-11, ZSM-22 and ZSM-23 zeolites.

5. A process according to claim 1 , wherein the oxygenate is selected from the group consisting of alkanols and di-alkylethers having up to five carbon atoms.

6. A process according to claim 5 , where the oxygenate is methanol, dimethylether, or a mixture thereof.

7. A process according to claim 1 , further comprising the following step:

g) recycling at least part of the tertiary butanol obtained in step f) to step a).

8. A process according to claim 7 , wherein tertiary butanol is co-produced in step e) and wherein tertiary butanol produced in step e) is recycled to step a).

9. A process according to claim 7 , wherein the tertiary butanol recycled to step a) is dehydrated prior to recycling to step a).

10. A process according to claim 8 , wherein the tertiary butanol recycled to step a) is dehydrated prior to recycling to step a).

11. A process according to claim 1 , wherein at least part of the tertiary butanol obtained in step f) is first dehydrated and then hydrogenated to obtain isobutane and wherein the isobutane thus-obtained is recycled to step e).

12. A process according to claim 11 , wherein the dehydrated tertiary butanol is hydrogenated by supplying the dehydrated tertiary butanol to hydrogenation step c).

13. A process according to claim 1 , wherein a part of the fraction comprising C4 hydrocarbons obtained in step b) is recycled directly to step a).

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 21, 2013
From: CHEWTER, LESLIE ANDREW; HENRY, HERVE; OLDENHOVE, PIETER; RAMESH, RAJARAM; VAN WESTRENEN, JEROEN
To: SHELL OIL COMPANY
Reel/Frame 029664/0001 →
Priority Claims (1)
EP 11185489 · Oct 17, 2011 · regional
Continuity (1)
Related Publication 20130096329A1 · Apr 18, 2013