# US 10,766,839 B2 · Process for converting olefins to alcohols, ethers, or combinations thereof

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- Number: US 10,766,839 B2
- Document ID: US10766839B2
- Status: Granted
- Kind: B2
- Application number: 16/076,734
- Filed: 2017-02-10
- Published: 2019-02-14
- Granted: 2020-09-08
- Earliest claimed: 2016-02-11
- Assignees: Dow Technology Investments LLC
- Applicants: Dow Technology Investments LLC
- Inventors: Michael C. Becker; Michael A. Brammer; Jason F. Giles; Glenn A. Miller; George R. Phillips; Rick B. Watson; Stephane Wambergue; Martin Lucas Smidt
- Web page: https://patentgrep.com/patent/US10766839B2

## CPC

- C07C 29/141: with hydrogen or hydrogen-containing gases
- C07C 41/01: Preparation of ethers
- C07C 45/50: by oxo-reactions
- C07C 45/505: {Asymmetric hydroformylation}
- C10L 1/1824: {mono-hydroxy}
- C10L 1/1852: {Ethers; Acetals; Ketals; Orthoesters}
- C10L 2200/0423: Gasoline
- C10L 2270/023: for gasoline engines
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## 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.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 5)

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

### Claim 7 (depends on 5)

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

### Claim 8 (depends on 5)

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

### Claim 9 (depends on 5)

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.

### Claim 10 (depends on 5)

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.

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 5)

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.

### Claim 13 (depends on 12)

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

### Claim 14 (depends on 1)

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).