GB720129A - Dehydrochlorination of polychlorocyclohexanes - Google Patents
Dehydrochlorination of polychlorocyclohexanesInfo
- Publication number
- GB720129A GB720129A GB24697/52A GB2469752A GB720129A GB 720129 A GB720129 A GB 720129A GB 24697/52 A GB24697/52 A GB 24697/52A GB 2469752 A GB2469752 A GB 2469752A GB 720129 A GB720129 A GB 720129A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- sulphonic acid
- dehydrochlorination
- hexachloride
- sulphonic
- 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
- 238000007033 dehydrochlorination reaction Methods 0.000 title abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 abstract 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 abstract 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 abstract 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 abstract 1
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 abstract 1
- HKCFHDMLRDLQSN-UHFFFAOYSA-N 4-chloro-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1Cl HKCFHDMLRDLQSN-UHFFFAOYSA-N 0.000 abstract 1
- BRIXOPDYGQCZFO-UHFFFAOYSA-N 4-ethylphenylsulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C=C1 BRIXOPDYGQCZFO-UHFFFAOYSA-N 0.000 abstract 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 abstract 1
- HWHNEHLXBIWKHC-UHFFFAOYSA-N ClC(C=CC=C1)=C1Cl.Cl.Cl.Cl.Cl.Cl.Cl Chemical compound ClC(C=CC=C1)=C1Cl.Cl.Cl.Cl.Cl.Cl.Cl HWHNEHLXBIWKHC-UHFFFAOYSA-N 0.000 abstract 1
- SGOWAUYYANZZHE-UHFFFAOYSA-N ClC1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl.Cl Chemical compound ClC1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl.Cl SGOWAUYYANZZHE-UHFFFAOYSA-N 0.000 abstract 1
- 241000158728 Meliaceae Species 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229940045996 isethionic acid Drugs 0.000 abstract 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 abstract 1
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 abstract 1
- AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical compound OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229960003080 taurine Drugs 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polychlorocyclohexanes such as benzene hexachloride are dehydrochlorinated by contacting at a temperature of at least 180 DEG C. with a catalytic amount of a sulphonic acid. Preferably the polychlorocyclohexane is contacted at 180-350 DEG C., more preferably at 220-350 DEG C. with 0.01 to 10 per cent of the catalyst. Suitably the polychlorocyclohexane is contacted with not more than 2 per cent of a catalyst such as o- or p-toluenesulphonic acid, benzenesulphonic acid, naphthalene 1 or 2 sulphonic acid, naphthalene 1 : 4-disulphonic acid, toluene-o -sulphonic acid, taurine, 3-aminopropane - 1 - sulphonic acid, decanesulphonic acid, isethionic acid and ethers thereof, p sulphoacetic acid, ethane-1 : 2-disulphonic acid, anthraquinone-1-sulphonic acid, m-benzenedisulphonic acid, ethylbenzene-p-sulphonic acid, 2-chlorotoluene-5-sulphonic acid and the mahogany acids. Dehydrochlorination of benzene hexachloride according to the invention produces 1 : 2 : 4- and 1 : 2 : 3-trichlorobenzene containing enhanced proportions of the 1 : 2 : 4-isomer, together with 2 : 3 : 4 : 5 : 6-pentachlorocyclohexene-1. Dehydrochlorination of monochlorobenzene hexachloride and dichlorobenzene hexachloride produces tetrachlorobenzene and pentachlorobenzene respectively. An example of the dehydrochlorination of benzene hexachloride using p-toluene sulphonic acid as a catalyst is given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US259281A US2662924A (en) | 1951-11-30 | 1951-11-30 | Dehydrochlorination of polychlorocyclohexanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB720129A true GB720129A (en) | 1954-12-15 |
Family
ID=22984298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24697/52A Expired GB720129A (en) | 1951-11-30 | 1952-10-02 | Dehydrochlorination of polychlorocyclohexanes |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2662924A (en) |
| FR (1) | FR1068108A (en) |
| GB (1) | GB720129A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2792434A (en) * | 1953-11-26 | 1957-05-14 | Basf Ag | Process for the production of hexachlorbenzene |
| US3080417A (en) * | 1958-12-31 | 1963-03-05 | Diamond Alkali Co | Addition-halogenated cyclohexyl esters |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1872700A (en) * | 1926-04-20 | 1932-08-23 | Dreyfus Camille | Method of carrying out organic chemical reactions in improved reaction media |
| US2042223A (en) * | 1934-06-23 | 1936-05-26 | Shell Dev | Rearrangement of unsaturated halides |
| US2569441A (en) * | 1949-03-14 | 1951-10-02 | Dow Chemical Co | Catalytic conversion of polychlorocyclohexanes to polychlorobenzene |
-
1951
- 1951-11-30 US US259281A patent/US2662924A/en not_active Expired - Lifetime
-
1952
- 1952-10-02 GB GB24697/52A patent/GB720129A/en not_active Expired
- 1952-10-04 FR FR1068108D patent/FR1068108A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US2662924A (en) | 1953-12-15 |
| FR1068108A (en) | 1954-06-22 |
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