Process and system to make olefin epoxides

Patent metadata

Field	Value
Publication number	US-11919876-B2
Application number	US-202017597888-A
Country	US
Kind code	B2
Filing date	Jun 30, 2020
Priority date	Aug 1, 2019
Publication date	Mar 5, 2024
Grant date	Mar 5, 2024

Abstract

Processes and systems for producing olefin epoxides with three or more carbon atoms by oxidation of the corresponding branched hydrocarbons using oxygen are disclosed. An example process for producing olefin epoxides may include oxidizing a branched alkane to produce at least an organic hydroperoxide. The example process may further include epoxidizing a branched alkene by a catalytic reaction with least a portion of the organic hydroperoxide to produce at least an olefin epoxide and an alcohol. The example process may further include converting at least a portion of the alcohol to either additional branched alkane and/or additional branched alkene.

First claim

The invention claimed is:

1. A process for producing olefin epoxides, comprising:
oxidizing a branched alkane to produce at least an organic hydroperoxide;
epoxidizing a branched alkene by a catalytic reaction with least a portion of the organic hydroperoxide to produce at least an olefin epoxide and an alcohol; and
converting at least a portion of the alcohol to additional branched alkane and additional branched alkene,
wherein the step of converting comprises dehydrating at least a portion of the alcohol to produce at least water and the additional branched alkene, and wherein the branched alkene from the step of epoxidizing comprises a quantity of the additional branched alkene that is produced in the step of converting, and
wherein the step of converting comprises dehydrating and hydrogenating at least a portion of the alcohol in the presence of hydrogen and a bifunctional catalyst to produce at least water and the additional branched alkane, wherein the branched alkane from the step of oxidizing comprises a quantity of the additional branched alkane produced in the converting, and wherein the bifunctional catalyst comprises a hydrogenation function and a dehydration function.

2. The process of claim 1 , wherein the branched alkane has the following structure:

wherein R 1 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and is linear, branched, or cyclic, R 2 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and is linear, branched, or cyclic, and R 3 is a hydrogen or a hydrocarbyl group having from 1 carbon atom to 9 carbon atoms and is linear, branched, or cyclic.

3. The process of claim 2 , wherein R 1 and R 2 are connected as part of a 4- to 14-membered ring.

4. The process of claim 1 , wherein the branched alkane comprises isobutane, and wherein the olefin oxide comprises isobutylene epoxide.

5. The process of claim 1 , wherein the step of oxidizing further produces additional alcohol.

6. The process of claim 1 , wherein the step of oxidizing comprises reacting the branched alkane with oxygen, wherein a source of the oxygen is air.

7. The process of claim 1 , wherein the step of epoxidizing is carried out using a soluble catalyst.

8. The process of claim 7 , wherein the soluble catalyst comprises a molybdenum dioxide bis(acetylacetonate).

9. The process of claim 1 :
wherein the step of oxidizing is represented by the following equation:

wherein the step of epoxidizing is represented by the following equation:

wherein the step of converting is represented by the following equation:

wherein R 1 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and that is linear, branched, or cyclic, R 2 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and that is linear, branched, or cyclic, and R 3 is a hydrogen or a hydrocarbyl group having from 1 carbon atom to 9 carbon atoms and that is linear, branched, or cyclic.

10. The process of claim 9 , wherein R 1 and R 2 are methyl groups and R 3 is the hydrogen.

11. The process of claim 1 :
wherein the step of oxidizing is represented by the following equation:

wherein the step of epoxidizing is represented by the following equation:

wherein the step of converting is represented by the following equation:

wherein R 1 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and that is linear, branched, or cyclic, R 2 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and that is linear, branched, or cyclic, and R 3 is a hydrogen or a hydrocarbyl group having from 1 carbon atom to 9 carbon atoms and that is linear, branched, or cyclic; and
wherein R 5 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and that is linear, branched, or cyclic, R 6 is a hydrocarbyl group having from 1 carbon atom to 10 carbon atoms and that is linear, branched, or cyclic, and R 7 is a hydrogen or a hydrocarbyl group having from 1 carbon atom to 9 carbon atoms and that is linear, branched, or cyclic.

12. The process of claim 11 , where R 5 and R 6 are connected as part of a 4- to 14-membered ring.

13. A process for producing olefin epoxides, comprising:
oxidizing a branched alkane stream comprising isobutane to produce at least t-butyl hydroperoxide;
epoxidizing isobutylene by a catalytic reaction with at least a portion of the t-butyl hydroperoxide to produce at least isobutylene epoxide and t-butyl alcohol;
dehydrating at least a portion of the t-butyl alcohol to produce water and additional isobutylene for the step of epoxidizing; and
dehydrating and hydrogenating at least a portion of the t-butyl alcohol in the presence of hydrogen and a bifunctional catalyst to produce at least water and additional branched alkane, wherein the branched alkane from the step of oxidizing comprises a quantity of the additional branched alkane produced in the converting, and wherein the bifunctional catalyst comprises a hydrogenation function and a dehydration function.

Assignees

• Exxonmobil Technology & Engineering Company

Inventors

• Wang Kun
• Shaffer Timothy D

Classifications

• C07D301/19 Primary

  with organic hydroperoxides · CPC title

• C07D303/04 Primary

  containing only hydrogen and carbon atoms in addition to the ring oxygen atoms · CPC title