# US 5,352,848 A · Nitrile removal in an etherification process

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- Number: US 5,352,848 A
- Document ID: US5352848A
- Status: Granted
- Kind: A
- Application number: 07/997,830
- Filed: 1992-12-29
- Granted: 1994-10-04
- Earliest claimed: 1992-12-29
- Assignees: Uop LLC
- Inventors: Paul R. Cottrell
- Web page: https://patentgrep.com/patent/US5352848A

## CPC

- C07C 41/44: by treatments giving rise to a chemical modification (by chemisorption C07C41/36)
- C07C 41/34: Separation; Purification; Stabilisation; Use of additives
- Y10S 203/06: Reactor-distillation
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

In an etherification process that uses an FCC effluent as a source of isoolefins, the buildup of nitriles in an alcohol-containing stream that is recycled to the etherification zone is prevented by dragging at least a portion of the methanol-containing stream to the FCC reaction zone. As a result, the etherification catalyst deactivation rate is reduced.

## Claims

### Claim 1

A method of treating an effluent of a fluid catalytic cracking zone, said effluent comprising isoalkenes and at least one nitrile compound which method comprises the steps of:
(a) contacting said effluent with a C.sub.1 -C.sub.5 monohydroxy alcohol in the presence of an etherification catalyst in an etherification zone under etherification conditions to react said isoalkenes with said alcohol to produce an etherification effluent stream comprising an ether;
(b) passing at least a portion of said etherification effluent stream to a separation zone to produce an ether-rich stream and a raffinate stream comprising said nitrile compound;
(c) passing said raffinate stream to an alcohol recovery zone to produce a hydrocarbon-rich raffinate stream and an alcohol-containing stream;
(d) recycling at least a portion of said alcohol-containing stream to said fluid catalytic cracking zone and
(e) recycling any remainder of said alcohol-containing stream to etherification zone.

### Claim 2 (depends on 1)

The method of claim 1 wherein said alcohol comprises methanol.

### Claim 3 (depends on 1)

The method of claim 1 wherein said separation zone comprises a distillation zone.

### Claim 4 (depends on 3)

The method of claim 3 wherein said distillation zone comprises a reactive distillation zone containing a bed of etherification catalyst to produce said ether.

### Claim 5 (depends on 1)

The method of claim 1 wherein said ether comprises methyl tertiary butyl ether.

### Claim 6 (depends on 1)

The method of claim 1 wherein said ether comprises tertiary amyl ether.

### Claim 7 (depends on 1)

The method of claim 1 wherein said fluid catalytic cracking effluent is contacted with a selective hydrogenation catalyst at selective hydrogenation conditions in a selective hydrogenation zone to selectively saturate diolefins to monoolefins.

### Claim 8 (depends on 1)

The method of claim 1 wherein said etherification catalyst comprises a macroporous acid-form sulfonic ion exchange resin.

### Claim 9 (depends on 1)

The method of claim 1 further comprising treating said fluid catalytic cracking effluent to remove sulfur compounds prior to contacting said effluent with said alcohol.

### Claim 10 (depends on 1)

The method of claim 1 further comprising monitoring the nitrile concentration of said alcohol-containing stream.

### Claim 11 (depends on 8)

The method of claim 8 wherein said nitrile compound comprises acetonitrile.

### Claim 12 (depends on 1)

The method of claim 1 further comprising fractionating said alcohol-containing stream to remove water prior to recycling said alcohol-containing stream to said fluid catalytic cracking zone.

### Claim 13

A method of treating an effluent of a fluid catalytic cracking zone, said effluent comprising isobutene and at least one nitrile compound which method comprises the steps of:
(a) contacting said effluent with methanol in the presence of an etherification catalyst in an etherification zone under etherification conditions to react said isobutene with said methanol to produce an etherification effluent stream which comprises methyl tertiary butyl ether;
(b) passing at least a portion of said etherification effluent stream to a distillation zone containing an etherification catalyst and contacting said methanol in the presence of said etherification catalyst in said distillation zone at etherification conditions to produce a methyl tertiary butyl ether-rich stream and an overhead raffinate stream;
(c) contacting said raffinate stream with a water-containing stream to produce a hydrocarbon-rich raffinate stream and a methanol-containing stream;
(d) monitoring the nitrile concentration of said methanol-containing stream;
(e) regulating said nitrile concentration in said methanol-containing stream by recycling at least a portion of said methanol-containing stream to said fluid catalytic cracking zone; and
(f) recycling any remainder of said alcohol-containing stream to said etherification zone.

### Claim 14 (depends on 13)

The method of claim 13 wherein said distillation zone comprises a reactive distillation zone containing a bed of etherification catalyst.

### Claim 15 (depends on 13)

The method of claim 13 wherein said fluid catalytic cracking effluent is contacted with a selective hydrogenation catalyst at selective hydrogenation conditions in a selective hydrogenation zone to selectively saturate diolefins to monoolefins.

### Claim 16 (depends on 13)

The method of claim 13 wherein said etherification catalyst comprises a macroporous acid-form sulfonic ion exchange resin.

### Claim 17 (depends on 13)

The method of claim 13 further comprising treating said fluid catalytic cracking effluent to remove sulfur compounds prior to contacting said effluent with said methanol.

### Claim 18 (depends on 13)

The method of claim 13 further comprising fractionating said methanol-containing stream to remove water prior to recycling said methanol-containing stream to said fluid catalytic cracking zone.

### Claim 19 (depends on 13)

The method of claim 13 wherein said nitrile comprises acetonitrile.

### Claim 20

A method for fluid catalytic cracking of a hydrocarbon feedstock which method comprises the steps of:
(a) contacting said hydrocarbon feedstock with a fluid catalytic cracking catalyst in a fluid catalytic cracking zone under fluid catalytic cracking conditions to produce a fluid catalytic cracking effluent stream comprising isobutene;
(b) treating said fluid catalytic cracking effluent stream to remove a substantial amount of any sulfur compounds contained therein;
(c) contacting said effluent from step (b) with a selective hydrogenation catalyst at selective hydrogenation conditions in a selective hydrogenation zone to selectively saturate diolefins to monoolefins;
(d) contacting said effluent from step (c) with methanol in the presence of an etherification catalyst comprising a macroporous acid-form sulfonic ion exchange resin in an etherification zone under etherification conditions to react said isobutene with said methanol to produce an etherification effluent stream which comprises methyl tertiary butyl ether;
(e) passing at least a portion of said etherification effluent stream to a distillation zone containing a bed of etherification catalyst comprising a macroporous acid-form sulfonic ion exchange resin and contacting said methanol in said bed of etherification catalyst in said distillation zone at etherification conditions to produce a methyl tertiary butyl ether-rich stream and an overhead raffinate stream comprising isobutane, normal butene, normal butane, methanol and isobutene;
(f) contacting said raffinate stream with a water-containing stream to produce a hydrocarbon-rich raffinate stream and a methanol-containing stream;
(g) fractionating said methanol-containing stream to produce a methanol-rich stream;
(h) monitoring acetonitrile concentration of said methanol-rich stream;
(i) regulating said acetonitrile concentration in said methanol-rich stream by recycling at least a portion of said methanol-rich stream to said fluid catalytic cracking zone; and
(j) recycling any remainder of said alcohol-containing stream to said etherification zone.