GB703202A - Processes for the preparation of polychloro alicyclic compounds - Google Patents
Processes for the preparation of polychloro alicyclic compoundsInfo
- Publication number
- GB703202A GB703202A GB2411551A GB2411551A GB703202A GB 703202 A GB703202 A GB 703202A GB 2411551 A GB2411551 A GB 2411551A GB 2411551 A GB2411551 A GB 2411551A GB 703202 A GB703202 A GB 703202A
- Authority
- GB
- United Kingdom
- Prior art keywords
- octachlorocyclopentene
- chlorine
- tetrachlorocyclopentane
- hexachlorocyclopentadiene
- chlorinating
- 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
- 150000001334 alicyclic compounds Chemical class 0.000 title 1
- DMZRCHJVWAKCAX-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octachlorocyclopentene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)(Cl)C1(Cl)Cl DMZRCHJVWAKCAX-UHFFFAOYSA-N 0.000 abstract 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- ZFMWDTNZPKDVBU-UHFFFAOYSA-N 1,2,3,4-tetrachlorocyclopentane Chemical compound ClC1CC(Cl)C(Cl)C1Cl ZFMWDTNZPKDVBU-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- -1 carbon atom hydrocarbon Chemical class 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 238000000197 pyrolysis Methods 0.000 abstract 2
- 239000012047 saturated solution Substances 0.000 abstract 2
- 229910000413 arsenic oxide Inorganic materials 0.000 abstract 1
- 229960002594 arsenic trioxide Drugs 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000001940 cyclopentanes Chemical class 0.000 abstract 1
- KTTMEOWBIWLMSE-UHFFFAOYSA-N diarsenic trioxide Chemical compound O1[As](O2)O[As]3O[As]1O[As]2O3 KTTMEOWBIWLMSE-UHFFFAOYSA-N 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Octachlorocyclopentene is prepared by chlorinating tetrachlorocyclopentane or mixtures of C5H6Cl4 and C5H5Cl5 in the liquid phase, by maintaining the reaction mixture constantly saturated with chlorine at a temperature within 20 DEG C. of that at which it refluxes at atmospheric pressure. Preferably the temperature is maintained at 170-275 DEG C. Phosphorus pentachloride or arsenic oxide may be present as a catalyst and the reaction may be carried out under increased chlorine pressure. The octachlorocyclopentene may be converted to hexachlorocyclopentadiene by pyrolysis at 275 DEG C.-500 DEG C. preferably by passing the octachlorocyclopentene through a heated zone at 375 DEG C.-500 DEG C., fractionating the pyrolysed product and returning any unchanged octachlorocyclopentene to the pyrolysis zone. Examples describe the chlorination of tetrachlorocyclopentane according to the invention to give octachlorocyclopentene which is pyrolysed to hexachlorocyclopentadiene. Tetrachlorocyclopentane is prepared by chlorinating a monocyclic, five carbon atom ring, hydrocarbon or a chlorinated derivative thereof containing less than four chlorine atoms in the molecule, in a saturated solution of chlorine at -50 DEG C. to +80 DEG C. Preferably the cyclic five carbon atom hydrocarbon, such as cyclopentadiene, is added to a cold saturated solution of chlorine in a solvent which may suitably be the chlorinated cyclopentane itself.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2411551A GB703202A (en) | 1951-10-16 | 1951-10-16 | Processes for the preparation of polychloro alicyclic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2411551A GB703202A (en) | 1951-10-16 | 1951-10-16 | Processes for the preparation of polychloro alicyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB703202A true GB703202A (en) | 1954-01-27 |
Family
ID=10206618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2411551A Expired GB703202A (en) | 1951-10-16 | 1951-10-16 | Processes for the preparation of polychloro alicyclic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB703202A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108276243A (en) * | 2017-12-20 | 2018-07-13 | 大连九信精细化工有限公司 | A kind of industrialized preparing process of octafluoro cyclopentene |
-
1951
- 1951-10-16 GB GB2411551A patent/GB703202A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108276243A (en) * | 2017-12-20 | 2018-07-13 | 大连九信精细化工有限公司 | A kind of industrialized preparing process of octafluoro cyclopentene |
| CN108276243B (en) * | 2017-12-20 | 2020-08-11 | 大连九信精细化工有限公司 | Industrial production method of octafluorocyclopentene |
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