# US 12,759,952 B2 · Metathesis of C4/C5 to propylene and 1-hexene

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- Number: US 12,759,952 B2
- Document ID: US12759952B2
- Status: Granted
- Kind: B2
- Application number: 18/684,771
- Filed: 2022-07-19
- Published: 2025-01-02
- Granted: 2026-10-13
- Earliest claimed: 2021-08-20
- Assignees: ExxonMobil Chemical Patents Inc.
- Applicants: ExxonMobil Chemical Patents Inc.
- Inventors: Emiel de Smit; Robert B. Larson
- Web page: https://patentgrep.com/patent/US12759952B2

## CPC

- C07C 6/04: at a carbon-to-carbon double bond
- C07C 5/333: Catalytic processes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A method, including: at least partially dehydrogenating a mixed alkane stream, including at least C4 and C5 alkanes, to generate at least a partial alkene stream and hydrogen; applying a metathesis reaction to the at least partial alkene stream to generate an effluent, wherein the metathesis reaction is optionally conducted in a presence of ethylene; and separating the effluent from the metathesis reaction into propylene, and 1-hexene.

## Claims

### Claim 1

A method, comprising:
at least partially dehydrogenating a mixed alkane stream, including at least C4 and C5 alkanes, to generate at least a partial alkene stream and hydrogen;
applying a metathesis reaction to the at least partial alkene stream to generate an effluent, wherein the metathesis reaction is optionally conducted in a presence of ethylene; and
separating the effluent from the metathesis reaction into propylene and 1-hexene.

### Claim 2 (depends on 1)

The method of claim 1, wherein the metathesis is conducted in the presence of ethylene, and the method further comprises controlling an amount of the ethylene supplied for the metathesis reaction in order to vary amounts generated of the propylene and 1-hexene.

### Claim 3 (depends on 1)

The method of claim 1, wherein the metathesis is conducted in the presence of ethylene recycled from a metathesis reactor product stream.

### Claim 4 (depends on 1)

The method of claim 1, wherein the metathesis reaction is conducted without co-feeding the ethylene.

### Claim 5 (depends on 1)

The method of claim 1, wherein the mixed C4 and C5 alkane stream is a natural gas liquid stream.

### Claim 6 (depends on 1)

The method of claim 1, wherein the mixed C4 and C5 alkane stream is the light ends or complete of the fluid catalytic cracking light cracked naphtha stream or other fluid catalytic cracking product stream, a steam cracker C4 or C5 raffinate stream or a mixed C4/C5 stream from a biomass source.

### Claim 7 (depends on 1)

The method of claim 1, wherein the separating includes separating the effluent into a C4-C7+ fraction, a C6-C7+ fraction, a C7+ fraction, and a mixed C6= fraction.

### Claim 8 (depends on 6)

The method of claim 6, wherein the method further comprises feeding the C6= fraction to a distillation column, wherein the 1-hexene is overheads of the distillation column and 2-hexene and 3-hexene are recycled back to an isomerization reactor.

### Claim 9 (depends on 1)

The method of claim 1, wherein the mixed C4 and C5 alkane stream includes linear and branched alkanes.

### Claim 10 (depends on 1)

The method of claim 1, wherein the separating includes generating a C4 and C5 alkane fraction, which is optionally recycled back to the dehydrogenating.

### Claim 11

A system, comprising:
a dehydrogenation unit configured to at least partially dehydrogenate a mixed alkane stream, including at least C4 and C5 alkanes, to generate at least a partial alkene stream and hydrogen;
a metathesis unit configured to apply a metathesis reaction to the alkene stream to generate an effluent, wherein the metathesis reaction is optionally conducted in a presence of ethylene; and
a separation unit configured to separate the effluent from the metathesis reaction into propylene and 1-hexene.

### Claim 12 (depends on 11)

The system of claim 11, wherein the separation unit includes a train of a plurality of distililation columns.

### Claim 13 (depends on 12)

The system of claim 12, wherein the plurality of distillation columns are configured to separate the effluent into a C4-C7+ fraction, a C6-C7+ fraction, a C7+ fraction, and a mixed C6= fraction.

### Claim 14 (depends on 13)

The system of claim 13, wherein the separation unit includes a distillation column configured to receive the mixed C6= fraction, wherein the 1-hexene is overheads of the distillation column and 2-hexene and 3-hexene are recycled back to an isomerization reactor.

### Claim 15 (depends on 13)

The system of claim 13, wherein the separation unit generates a C4 and C5 alkane fraction, which is optionally recycled back to the dehydrogenation unit.