EP0000847B1 - Production de chlorure de vinyle monomère - Google Patents
Production de chlorure de vinyle monomère Download PDFInfo
- Publication number
- EP0000847B1 EP0000847B1 EP78300280A EP78300280A EP0000847B1 EP 0000847 B1 EP0000847 B1 EP 0000847B1 EP 78300280 A EP78300280 A EP 78300280A EP 78300280 A EP78300280 A EP 78300280A EP 0000847 B1 EP0000847 B1 EP 0000847B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dichloroethane
- pyrolysis
- vinyl chloride
- process according
- dichloroethanes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 7
- 239000000178 monomer Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 17
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 15
- 238000000197 pyrolysis Methods 0.000 claims description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000007033 dehydrochlorination reaction Methods 0.000 description 3
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
Definitions
- the present invention relates to an essentially non-catalytic process for the preparation of vinyl chloride by the dehydrochlorination of mixtures of isomeric dichloroethanes.
- vinyl chloride can be produced by the pyrolytic dehydrochlorination of 1,2-dichloroethane.
- the process involves the passing of 1,2-dichloroethane through a small diameter reaction tube in which it is heated to elevated temperatures to bring about the dehydrochlorination thereof.
- it has not hitherto been possible to convert the isomeric 1,1-dichloroethane, which is a byproduct of the pyrolysis of 1,2-dichloroethane, into vinyl chloride in economic yields.
- US-A-2569923 describes a method of pyrolysing a mixture of 90% 1,1-dichloroethane and 10% 1,2-dichloroethane. However this mixture results only in a 35% conversion.
- the present invention is a process for producing vinyl chloride comprising pyrolysing at elevated temperature 1,2-dichloroethane mixed with between 0.1 and 10% by weight of 1,1-dichloroethane.
- the above reaction may be carried out in conventional tubular reactors as normally employed for the pyrolysis of 1,2-dichloroethane.
- the pyrolysis of mixtures of 1,1-dichloroethane and 1,2-dichloroethane in the specified range of concentrations significantly increases the conversion of 1, i-dichloroethane from about 20% (for the pure isomer) to above 90% (when present in the isomeric mixtures). Both below and above this range the conversion of the 1,2-isomer is depressed relatively.
- the amount of the 1,1-dichloroethane in the isomeric mixture being pyrolysed is preferably between 1 and 8%.
- the 1,1-isomer may be mixed with the pyrolysis feed prior to the introduction thereof into the reaction zone. Alternatively it may be incorporated in the pyrolysis feed in the reaction zone itself at the time of pyrolysis.
- the pyrolysis of the isomeric mixtures may be carried out in packed or unpacked tubular reactors. Where packed reactors are used they may suitably be packed with ceramic spheres.
- the pyrolysis of the isomeric mixture of dichloroethanes according to the present invention is suitably carried out at a temperature of between 450° and 550°C, preferably between 500° and 535°C.
- the pyrolysis of the isomeric mixture of dichloroethanes may be carried out at subatmospheric, atmospheric or super-atmospheric pressures. It is, however, preferred to use super- atmospheric pressure, preferably below 35 atmospheres.
- the pyrolysis of the isomeric mixture of dichloroethanes may be carried out in a continuous manner.
- the apparatus run at atmospheric pressure, consisted of feed reservoir, metering pump, vaporiser, cracker tube, coolers, organic product receiver, hydrogen chloride scrubbing column, scrub liquor reservoir and wet gas meter. There was also a nitrogen diluent/carrier feed applied to the vaporiser inlet.
- Feedstocks comprising pure 1,2-dichloroethane (1,2-EDC), 1,2-dichloroethane with up to 10 per cent by weight of 1,1-dich)oroethane (1,1-DCE) and also pure (98.2% by weight) 1,1-DCE were pyrolysed at a peak temperature of 500°C and a contact time of 4.5 seconds under conditions found to give a 50 per cent by weight conversion of pure 1,2-dichloroethane.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Claims (7)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3427077 | 1977-08-16 | ||
| GB3427077 | 1977-08-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000847A1 EP0000847A1 (fr) | 1979-02-21 |
| EP0000847B1 true EP0000847B1 (fr) | 1981-09-16 |
Family
ID=10363552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78300280A Expired EP0000847B1 (fr) | 1977-08-16 | 1978-08-14 | Production de chlorure de vinyle monomère |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0000847B1 (fr) |
| JP (1) | JPS5436205A (fr) |
| AU (1) | AU3890778A (fr) |
| CA (1) | CA1104590A (fr) |
| DE (1) | DE2861083D1 (fr) |
| GB (1) | GB2002357A (fr) |
| IT (1) | IT1098061B (fr) |
| NO (1) | NO782772L (fr) |
| NZ (1) | NZ188083A (fr) |
| PH (1) | PH14472A (fr) |
| PT (1) | PT68424A (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112021014592A2 (pt) | 2019-01-25 | 2021-10-05 | Suncor Energy Inc. | Compostos fotosensibilizadores, métodos de fabricação e aplicação em plantas |
| AU2020222515B2 (en) | 2019-02-15 | 2025-10-09 | Nutrien Ag Solutions (Canada) Inc. | The use of protoporphyrin IX derivatives to improve the health of plants |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR957327A (fr) * | 1946-12-17 | 1950-02-18 | ||
| DE1075592B (de) * | 1955-04-05 | 1960-02-18 | Ethyl Corporation, New York N Y (V St A) | Verfahren zur Herstellung von Vinylchlorid oder Vinylidenchlorid |
| FR1306945A (fr) * | 1960-11-25 | 1962-10-19 | Wacker Chemie Gmbh | Procédé destiné à réduire la décomposition du chlorure de vinyle lors de la dissociation catalytique du dichloréthane |
| US3450780A (en) * | 1966-03-23 | 1969-06-17 | Monsanto Co | Dehydrohalogenation of 1,2-dichloroethane |
| DE1925568C3 (de) * | 1969-05-20 | 1974-09-19 | Wacker-Chemie Gmbh, 8000 Muenchen | Verfahren zur Dehydrochlorierung von asymmetrisch substituierten Polychloräthanen |
-
1978
- 1978-07-19 GB GB7830310A patent/GB2002357A/en not_active Withdrawn
- 1978-08-08 NZ NZ188083A patent/NZ188083A/xx unknown
- 1978-08-09 CA CA308,967A patent/CA1104590A/fr not_active Expired
- 1978-08-11 IT IT26765/78A patent/IT1098061B/it active
- 1978-08-14 DE DE7878300280T patent/DE2861083D1/de not_active Expired
- 1978-08-14 EP EP78300280A patent/EP0000847B1/fr not_active Expired
- 1978-08-14 PT PT68424A patent/PT68424A/pt unknown
- 1978-08-15 JP JP9873278A patent/JPS5436205A/ja active Pending
- 1978-08-15 NO NO782772A patent/NO782772L/no unknown
- 1978-08-15 AU AU38907/78A patent/AU3890778A/en active Pending
- 1978-08-16 PH PH21504A patent/PH14472A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2861083D1 (en) | 1981-12-03 |
| IT7826765A0 (it) | 1978-08-11 |
| GB2002357A (en) | 1979-02-21 |
| AU3890778A (en) | 1980-02-21 |
| PT68424A (en) | 1978-09-01 |
| CA1104590A (fr) | 1981-07-07 |
| NO782772L (no) | 1979-02-19 |
| PH14472A (en) | 1981-08-07 |
| JPS5436205A (en) | 1979-03-16 |
| IT1098061B (it) | 1985-08-31 |
| NZ188083A (en) | 1979-11-01 |
| EP0000847A1 (fr) | 1979-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Designated state(s): BE DE FR NL SE |
|
| 17P | Request for examination filed | ||
| GRAA | (expected) grant |
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| AK | Designated contracting states |
Designated state(s): BE DE FR NL SE |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
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|
| REF | Corresponds to: |
Ref document number: 2861083 Country of ref document: DE Date of ref document: 19811203 |
|
| NLV1 | Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act | ||
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19830503 |
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| PLBE | No opposition filed within time limit |
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| STAA | Information on the status of an ep patent application or granted ep patent |
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