Process for converting olefins to alcohols, ethers, or combinations thereof

Patent metadata

Field	Value
Publication number	US-10766839-B2
Application number	US-201716076734-A
Country	US
Kind code	B2
Filing date	Feb 10, 2017
Priority date	Feb 11, 2016
Publication date	Sep 8, 2020
Grant date	Sep 8, 2020

Abstract

The present invention relate to processes for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive. In one embodiment, the process comprises (a) receiving a feed stream, wherein the feed stream comprises one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight based on the weight of the feed stream; (b) hydroformylating the feed stream in the presence of a catalyst to convert at least 80% of the olefins from the feed stream to oxygenates; (c) separating a product stream from step (b) into an oxygenate stream and a stream comprising unreacted olefins, inerts, the catalyst, and the remaining oxygenates; and (d) treating the oxygenate stream to convert a plurality of the oxygenates into at least one of an alcohol, an ether, or combinations thereof is suitable for use as a gasoline additive.

First claim

What is claimed is:

1. A process for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive, the process comprising:
(a) receiving a feed stream, wherein the feed stream comprises one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight based on the weight of the feed stream, wherein the feed stream comprises at least 50% by weight ethylene, propylene, and/or butene and at least 15% by weight alkanes:
(b) hydroformylating the feed stream in the presence of a catalyst to convert at least 80% of the olefins from the feed stream to oxygenates, wherein the catalyst comprises rhodium and at least one of organophosphorous ligand:
(c) separating a product stream from step (b) into an oxygenate stream and a stream comprising unreacted olefins, inerts, the catalyst, and the remaining oxygenates; and
(d) treating the oxygenate stream to convert a plurality of the oxygenates into at least one of an alcohol, an ether, or combinations thereof having at least 3 carbon atoms, wherein at least 25 weight percent of the alcohols and ethers having at least 3 carbon atoms are branched based on the total weight of the alcohols and ethers having at least 3 carbon atoms, and wherein the alcohols, ethers, or combination thereof is suitable for use as a gasoline additive.

2. The process of claim 1 , wherein the feed stream comprises at least 50% propylene.

3. The process of claim 1 , wherein the oxygenate stream in step (c) comprises an aldehyde.

4. The process of claim 1 , wherein treating the oxygenate stream comprises hydrogenation of the oxygenate into an alcohol.

5. The process of claim 1 , wherein the oxygenates comprise an isobutyraldehyde and wherein treating the oxygenate stream comprises hydrogenation of the isobutyraldehyde into isobutyl alcohol or diisobutyl ether.

6. The process of claim 5 , further comprising removing at least some of the alcohols and ethers after step (d).

7. The process of claim 5 , further comprising adding a stream comprising the alcohols, the ethers, or the combination thereof after step (d) to gasoline.

8. The process of claim 5 , wherein at least 90% of the alcohols from step (d) comprise alcohols having 3 to 6 carbon atoms.

9. The process of claim 5 , wherein at least 40% of the alcohols and ethers having at least 3 carbon atoms are branched based on the total weight of the alcohols and ethers having at least 3 carbon atoms.

10. The process of claim 5 , wherein the catalyst comprises rhodium and at least one of triorganophosphite, dicyclohexylphenylphosphine, cyclohexyldiphenylphosphine, triphenylphosphine, 2,6-di-t-butyl-4-methylphenyl-1,1′-biphenyl-2,2′diylphosphite, tris(2,4-di-tert-butylphenyl)phosphite, or 4,8-bis(1,1-dimethylethyl)-6-[2-(1,1-dimethylethyl)-4-methoxyphenoxy]-2,10-dimethoxy-dibenzo WA [1,3,2]dioxaphosphepin.

11. The process of claim 1 , wherein the feed stream is hydroformylated using a rhodium-based catalyst with a reactivity of greater than 0.5 turnovers/second on a rhodium-atom basis.

12. The process of claim 5 , wherein the feed stream comprises one or more alkanes and wherein during the separation step (c) alkanes from the feed stream facilitate the separation, or wherein the separation step (c) comprises a stripping gas vaporizer wherein alkanes from the feed stream are used to facilitate the separation.

13. The process of claim 12 , wherein the feed stream comprises at least 20 weight percent alkanes, based on the weight of the feed stream.

14. The process of claim 1 , wherein at least 90% of the olefins in the feed stream are converted to oxygenates in the hydroformylation of step (b).

Assignees

• Dow Technology Investments Llc

Inventors

• Becker Michael C
• Brammer Michael A
• Giles Jason F
• Miller Glenn A
• Phillips George R
• Watson Rick B
• Wambergue Stephane
• Smidt Martin Lucas

Classifications

• C07C45/50

  by oxo-reactions · CPC title

• C07C47/02

  Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen · CPC title

• C07C31/10

  containing three carbon atoms · CPC title

• C07C31/12

  containing four carbon atoms · CPC title

• C07C29/141 Primary

  with hydrogen or hydrogen-containing gases · CPC title