# US 11,999,672 B2 · High purity isoamylene production from tertiary amyl methyl ether decomposition

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- Number: US 11,999,672 B2
- Document ID: US11999672B2
- Status: Granted
- Kind: B2
- Application number: 17/930,905
- Filed: 2022-09-09
- Published: 2023-01-05
- Granted: 2024-06-04
- Earliest claimed: 2020-11-02
- Assignees: Lummus Technology Inc.
- Applicants: Lummus Technology LLC
- Inventors: Rosette Barias; Liang Chen; Michael Jon Scott
- Web page: https://patentgrep.com/patent/US11999672B2

## CPC

- C07C 1/20: starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C 7/04: by distillation
- C07C 7/10: by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
- C07C 29/10: of ethers, including cyclic ethers, e.g. oxiranes
- C07C 29/80: by distillation
- C07C 41/06: by addition of organic compounds only
- C07C 41/58: Separation; Purification; Stabilisation; Use of additives
- Y02P 20/10: Process efficiency
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Systems and methods for the production of a high purity isoamylene product. The isoamylene in a mixed hydrocarbon stream may initially be converted to TAME via etherification, and a subsequent decomposition of the TAME may result in a high purity isoamylene stream with very low impurities that is suitable for a variety of petrochemical applications, such as for use in the production of fragrances, pesticides, peroxides, polymer antioxidants, UV stabilizers and hydrocarbon resins.

## Claims

### Claim 1

A system for producing a high purity isoamylene stream, the system comprising:
a purification zone comprising a divided wall distillation column configured to receive a crude tertiary amyl ether from a feed source, the divided wall distillation column configured to separate the crude tertiary amyl ether into an overhead lights stream, a bottom heavies stream, and a tertiary amyl ether containing side draw stream;
a decomposition reactor containing a decomposition catalyst configured to convert the tertiary amyl ether as a vapor into isoamylene and alcohol and to produce a reaction effluent;
a separation zone configured to receive the reaction effluent and to separate the reaction effluent into an alcohol stream, a vent stream, a heavy oxygenate stream, and an isoamylene product stream.

### Claim 2 (depends on 1)

The system of claim 1, further comprising a feed line for feeding the heavy oxygenate stream to the purification zone.

### Claim 3 (depends on 1)

The system of claim 1, further comprising a reaction zone configured to react an isoamylene containing stream with methanol to produce the crude tertiary amyl ether.

### Claim 4 (depends on 3)

The system of claim 3, wherein the separation zone comprises:
an isoamylene lights column configured to receive the reactor effluent and to separate the reactor effluent into an overhead stream and a bottoms stream comprising the heavy oxygenates, recovered as the heavy oxygenate stream;
a methanol extraction column, configured to receive the overhead stream from the isoamylene lights column and to recover an overheads stream and to recover the alcohol stream as a bottoms stream;
an isoamylene finishing column, configured to receive the overheads stream from the methanol extraction column and to recover the vent stream as an overheads product and to recover the isoamylene product stream as a bottoms product.

### Claim 5 (depends on 4)

The system of claim 4, further comprising a flow line for feeding the alcohol stream to the reaction zone.

### Claim 6 (depends on 1)

The system of claim 1, wherein the separation zone comprises:
a methanol extraction column, configured to receive the reactor effluent and to separate the reactor effluent into an overhead stream and a bottoms stream comprising the alcohol, recovered as the alcohol stream;
an isoamylene lights column configured to receive the overhead stream from the methanol extraction column and to recover the vent stream as an overheads and a bottoms stream;
a heavies column, configured to receive the bottoms stream from the isoamylene lights column and to recover the isoamylene product stream as an overheads product and to recover the heavy oxygenate stream as a bottoms product.

### Claim 7 (depends on 6)

The system of claim 6, further comprising a methanol finishing column configured for receiving the alcohol stream and for producing a purified alcohol product stream.

### Claim 8 (depends on 1)

The system of claim 1, further comprising a heat exchanger for vaporizing the tertiary amyl ether containing side draw stream.

### Claim 9 (depends on 8)

The system of claim 8, further comprising a feed line for feeding the heavy oxygenate stream to the purification zone.

### Claim 10 (depends on 8)

The system of claim 8, further comprising a reaction zone configured to react an isoamylene containing stream with methanol to produce the crude tertiary amyl ether.

### Claim 11 (depends on 10)

The system of claim 10, wherein the separation zone comprises:
an isoamylene lights column configured to receive the reactor effluent and to separate the reactor effluent into an overhead stream and a bottoms stream comprising the heavy oxygenates, recovered as the heavy oxygenate stream;
a methanol extraction column, configured to receive the overhead stream from the isoamylene lights column and to recover an overheads stream and to recover the alcohol stream as a bottoms stream;
an isoamylene finishing column, configured to receive the overheads stream from the methanol extraction column and to recover the vent stream as an overheads product and to recover the isoamylene product stream as a bottoms product.

### Claim 12 (depends on 11)

The system of claim 11, further comprising a flow line for feeding the alcohol stream to the reaction zone.

### Claim 13 (depends on 8)

The system of claim 8, wherein the separation zone comprises:
a methanol extraction column, configured to receive the reactor effluent and to separate the reactor effluent into an overhead stream and a bottoms stream comprising the alcohol, recovered as the alcohol stream;
an isoamylene lights column configured to receive the overhead stream from the methanol extraction column and to recover the vent stream as an overheads and a bottoms stream;
a heavies column, configured to receive the bottoms stream from the isoamylene lights column and to recover the isoamylene product stream as an overheads product and to recover the heavy oxygenate stream as a bottoms product.

### Claim 14 (depends on 13)

The system of claim 13, further comprising a methanol finishing column configured for receiving the alcohol stream and for producing a purified alcohol product stream.

### Claim 15

A system for producing a high purity isoamylene stream, the system comprising:
a reaction zone configured to react an isoamylene containing stream with methanol to produce a crude tertiary amyl ether;
a purification zone comprising a divided wall distillation column configured to receive the crude tertiary amyl ether from a feed source, the divided wall distillation column configured to separate the crude tertiary amyl ether into an overhead lights stream, a bottom heavies stream, and a tertiary amyl ether containing side draw stream;
a heat exchanger for vaporizing the tertiary amyl ether containing side draw stream;
a decomposition reactor containing a decomposition catalyst configured to convert the tertiary amyl ether into isoamylene and alcohol and to produce a reaction effluent; and
a separation zone configured to receive the reaction effluent and to separate the reaction effluent into an alcohol stream, a vent stream, a heavy oxygenate stream, and an isoamylene product stream; and a feed line for feeding the heavy oxygenate stream to the purification zone,
wherein the separation zone comprises:
an isoamylene lights column configured to receive the reactor effluent and to separate the reactor effluent into an overhead stream and a bottoms stream comprising the heavy oxygenates, recovered as the heavy oxygenate stream;
a methanol extraction column, configured to receive the overhead stream from the isoamylene lights column and to recover an overheads stream and to recover the alcohol stream as a bottoms stream; and
an isoamylene finishing column, configured to receive the overheads stream from the methanol extraction column and to recover the vent stream as an overheads product and to recover the isoamylene product stream as a bottoms product.

### Claim 16 (depends on 15)

The system of claim 15, further comprising a flow line for feeding the alcohol stream to the reaction zone.

### Claim 17 (depends on 15)

The system of claim 15, further comprising a methanol finishing column configured for receiving the alcohol stream and for producing a purified alcohol product stream.
