# US 4,391,677 A · Process for producing substantially sulphur-free butene-1

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- Number: US 4,391,677 A
- Document ID: US4391677A
- Status: Granted
- Kind: A
- Application number: 06/296,873
- Filed: 1981-08-27
- Granted: 1983-07-05
- Earliest claimed: 1979-03-21
- Assignees: Davy McKee (Oil & Chemicals) Limited
- Inventors: Norman Harris; John F. Flintoff; John W. Kippax
- Web page: https://patentgrep.com/patent/US4391677A

## CPC

- B29C 53/12: helically, e.g. for making springs {(for textile fibres D02G1/00)}
- B29C 43/00: Compression moulding, i.e. applying external pressure to flow the moulding material; Apparatus therefor {(by liberation of internal stresses B29C61/006)}
- B29C 48/08: flexible, e.g. films
- B29C 48/12: Articles with an irregular circumference when viewed in cross-section, e.g. window profiles
- B29C 48/131: {Curved articles}
- B29C 48/266: {Means for allowing relative movements between the apparatus parts, e.g. for twisting the extruded article or for moving the die along a surface to be coated}
- B29C 65/18: using heated tools
- B29C 65/42: between pre-assembled parts {(B29C65/605 takes precedence)}
- B29C 66/5241: {for forming coaxial connections, i.e. the profiled elements to be joined forming a zero angle relative to each other}
- B29C 66/73752: {the to-be-joined areas of both parts to be joined being uncured}
- B29C 66/73941: {characterised by the materials of both parts being thermosets}
- B29D 99/0053: {Producing sealings (B29D99/0085 takes precedence)}
- C07C 7/005: {Processes comprising at least two steps in series}
- C07C 7/04: by distillation
- C07C 7/11: by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
- C07C 7/12: by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
- C07C 7/148: by treatment giving rise to a chemical modification of at least one compound
- F16J 15/22: shaped as strands, ropes, threads, ribbons, or the like
- B29C 66/71: {characterised by the composition of the plastics material of the parts to be joined (welding bar compositions B29C65/125)}
- B29C 66/84: {Specific machine types or machines suitable for specific applications}
- B29K 2101/10: Thermosetting resins
- B29K 2105/243: {Partially cured}
- B29L 2031/26: Sealing devices, e.g. packaging for pistons or pipe joints
- B29L 2031/265: {Packings, Gaskets}
- Y10S 264/40: Processes of coiling plastics
- Y10S 277/924: Deformation, material removal, or molding for manufacture of seal
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- F16J: PISTONS {(specially adapted for dampers F16F9/32)}; CYLINDERS; SEALINGS
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A process is disclosed for producing a substantially sulphur-free, butene-1 rich stream from a butene-containing C.sub.4 hydrocarbon feed stream by passage through a desulphurization zone, e.g. successive beds of active alumina and zinc oxide, and then distilling it. The desulphurization zone adsorbs, absorbs or converts to higher boiling sulphurous compounds low boiling sulphurous impurities such as H.sub.2 S, COS and CH.sub.3 SH. A sulphur-free butene-1 rich stream is recovered overhead from the distillation zone, while a butene-2 rich stream containing higher boiling sulphurous impurities originally present or produced in the desulphurization zone is recovered as a bottom product. A dechlorination zone (containing, for example, a charge of copper impregnated active carbon) can be provided upstream or downstream from the desulphurization zone but upstream from the distillation zone or can be provided in the path of the butene-1 rich stream from the distillation zone. The butene-1 rich product is suitable for use as a hydroformylation feedstock.

## Claims

### Claim 1

A process for the production of a substantially sulphur-free, butene-1 rich stream suitable for use as a hydroformylation feedstock from a butene-containing C.sub.4 hydrocarbon feed stream containing a minor amount of at least one sulphurous component selected from hydrogen sulphide, carbonyl sulphide, methyl mercaptan and mixtures of at least one thereof with at least one higher boiling sulphurous compound, which comprises providing a desulphurization zone maintained under desulphurization conditions and containing a charge of at least one solid desulphurization medium capable of converting to higher boiling sulphurous compounds at least a portion of the hydrogen sulphide, carbonyl sulphide, and methyl mercaptan present in the feed stream and of absorbing or adsorbing substantially the remainder of any hydrogen sulphide, carbonyl sulphide and methyl mercaptan present in the feed stream, contacting the feed stream in the desulphurization zone with the solid desulphurization medium in the presence of from about 20 ppm up to about 1000 ppm water, passing thus treated feed stream, now essentially free from hydrogen sulphide, carbonyl sulphide and methyl mercaptan, but containing at least one higher boiling sulphurous compound, said at least one higher boiling compound having been produced in the desulphurization zone, to a distillation zone, recovering as a bottom product from the distillation zone a butene-2 rich stream containing said at least one higher boiling sulphurous compound, and recovering as an overhead product from the distillation zone a substantially sulphur-free, butene-1 rich stream.

### Claim 2 (depends on 1)

A process according to claim 1, in which the desulphurization zone is maintained at a temperature in the range of from about 0.degree. C. up to about 200.degree. C.

### Claim 3 (depends on 2)

A process according to claim 2, in which the desulphurization zone is maintained at a temperature in the range of from about 0.degree. C. to about 40.degree. C.

### Claim 4 (depends on 1)

A process according to claim 1, in which the desulphurization zone contains a charge of active alumina.

### Claim 5 (depends on 4)

A process according to claim 4, in which the desulphurization zone contains a charge of zinc oxide downstream in the path of the feed stream from the charge of active alumina.

### Claim 6 (depends on 1, 2, 3, 4, 5)

A process according to claim 1, 2, 3, 4 or 5, in which the feed stream contains from about 20 ppm up to about 1000 ppm of water.

### Claim 7 (depends on 6)

A process according to claim 6, which further includes the step of passing the feed stream, upstream or downstream from the desulphurization zone but upstream from the distillation zone, through a dechlorination zone containing a charge of a dechlorination material and maintained under dechlorination conditions.

### Claim 8 (depends on 7)

A process according to claim 7, in which the dechlorination zone comprises a charge of copper-impregnated active carbon.

### Claim 9 (depends on 8)

A process according to claim 8, in which the temperature in the dechlorination zone ranges from about -10.degree. C. up to about 200.degree. C.

### Claim 10 (depends on 6)

A process according to claim 6, which further includes the step of passing the overhead product stream from the distillation zone through a dechlorination zone containing a charge of dechlorination material and maintained under dechlorination conditions.

### Claim 11 (depends on 10)

A process according to claim 10, in which the dechlorination zone comprises a charge of copper-impregnated active carbon.

### Claim 12 (depends on 11)

A process according to claim 11, in which the temperature in the dechlorination zone ranges from about -10.degree. C. up to about 200.degree. C.

### Claim 13

A process for the production of a butene-1 rich stream containing not more than 0.1 ppm sulphur from a butene-containing C.sub.4 hydrocarbon feed stream containing a minor amount of at least one sulphurous component selected from hydrogen sulphide, carbonyl sulphide, methyl mercaptan and mixtures of at least one thereof with at least one higher boiling sulphurous compound, which comprises providing a desulphurization zone maintained under desulphurization conditions and containing a charge of at least one solid desulphurization medium capable of converting to higher boiling sulphurous compounds by reaction with one or more components of the feed stream at least a portion of the hydrogen sulphide, carbonyl sulphide, and methyl mercaptan present in the feed stream and of absorbing or adsorbing substantially the remainder of any hydrogen sulphide, carbonyl sulphide and methyl mercaptan present in the feed stream, contacting the feed stream in the desulphurization zone with the solid desulphurization medium, passing thus treated feed stream, now essentially free from hydrogen sulphide, carbonyl sulphide and methyl mercaptan, to a distillation zone, recovering from the distillation zone a butene-2 rich stream and, as an overhead product, a butene-1 rich stream containing less than 0.1 ppm sulphur, and recovering substantially all of the higher boiling sulphurous compounds present in the treated feed stream in the bottoms product from the distillation zone.