DE2810398C2 - Verfahren zur Herstellung von Tetrachlorcyclobutenon aus Hexachlorcyclobuten - Google Patents
Verfahren zur Herstellung von Tetrachlorcyclobutenon aus HexachlorcyclobutenInfo
- Publication number
- DE2810398C2 DE2810398C2 DE2810398A DE2810398A DE2810398C2 DE 2810398 C2 DE2810398 C2 DE 2810398C2 DE 2810398 A DE2810398 A DE 2810398A DE 2810398 A DE2810398 A DE 2810398A DE 2810398 C2 DE2810398 C2 DE 2810398C2
- Authority
- DE
- Germany
- Prior art keywords
- hexachlorocyclobutene
- hexachloro
- butadiene
- mixture
- sulfuric acid
- 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
- QXFKQCYWJWBUTR-UHFFFAOYSA-N 1,2,3,3,4,4-hexachlorocyclobutene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C1(Cl)Cl QXFKQCYWJWBUTR-UHFFFAOYSA-N 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 15
- NWDONRNKYCKRNT-UHFFFAOYSA-N 2,3,4,4-tetrachlorocyclobut-2-en-1-one Chemical compound ClC1=C(Cl)C(Cl)(Cl)C1=O NWDONRNKYCKRNT-UHFFFAOYSA-N 0.000 title claims description 14
- 239000003701 inert diluent Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 28
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000003756 stirring Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 7
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 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 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QVHWOZCZUNPZPW-UHFFFAOYSA-N 1,2,3,3,4,4-hexafluorocyclobutene Chemical compound FC1=C(F)C(F)(F)C1(F)F QVHWOZCZUNPZPW-UHFFFAOYSA-N 0.000 description 1
- UAOUDDMGGTWZKO-UHFFFAOYSA-N 2,2,3,3,5,5-hexachlorocyclopentan-1-one Chemical compound ClC1(Cl)CC(Cl)(Cl)C(Cl)(Cl)C1=O UAOUDDMGGTWZKO-UHFFFAOYSA-N 0.000 description 1
- BDGMAHZSLYJCAU-UHFFFAOYSA-N 2,3,4,4-tetrachlorocyclobut-2-en-1-one Chemical compound ClC1=C(Cl)C(Cl)(Cl)C1=O.ClC1=C(Cl)C(Cl)(Cl)C1=O BDGMAHZSLYJCAU-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2810398A DE2810398C2 (de) | 1978-03-10 | 1978-03-10 | Verfahren zur Herstellung von Tetrachlorcyclobutenon aus Hexachlorcyclobuten |
| FR7905261A FR2419270A1 (fr) | 1978-03-10 | 1979-02-28 | Procede de preparation de tetrachlorocyclobutenone a partir d'hexachlorocyclobutene |
| IT48271/79A IT1114557B (it) | 1978-03-10 | 1979-03-08 | Procedimento per produrre tetraclorociclobutenone da esacloro ciclobutene |
| GB7908351A GB2018748B (en) | 1978-03-10 | 1979-03-09 | Process for the manufacture of tetrachlorocyclobutenone |
| NL7901912A NL7901912A (nl) | 1978-03-10 | 1979-03-09 | Werkwijze voor de bereiding van tetrachloorcyclobutenen uit hexachloorcyclobuteen. |
| JP2681979A JPS54128548A (en) | 1978-03-10 | 1979-03-09 | Manufacture of tetrachlorocyclobutenone from hexachlorocyclobutene |
| US06/019,205 US4272633A (en) | 1978-03-10 | 1979-03-09 | Process for the manufacture of tetrachlorocyclobutenone from hexachlorocyclobutene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2810398A DE2810398C2 (de) | 1978-03-10 | 1978-03-10 | Verfahren zur Herstellung von Tetrachlorcyclobutenon aus Hexachlorcyclobuten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2810398A1 DE2810398A1 (de) | 1979-09-20 |
| DE2810398C2 true DE2810398C2 (de) | 1983-08-25 |
Family
ID=6034062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2810398A Expired DE2810398C2 (de) | 1978-03-10 | 1978-03-10 | Verfahren zur Herstellung von Tetrachlorcyclobutenon aus Hexachlorcyclobuten |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4272633A (enExample) |
| JP (1) | JPS54128548A (enExample) |
| DE (1) | DE2810398C2 (enExample) |
| FR (1) | FR2419270A1 (enExample) |
| GB (1) | GB2018748B (enExample) |
| IT (1) | IT1114557B (enExample) |
| NL (1) | NL7901912A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3314431A1 (de) * | 1983-04-21 | 1984-10-25 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von quadratsaeure |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2650939A (en) * | 1948-10-01 | 1953-09-01 | Purdue Research Foundation | Hexachlorocyclopentenone preparation |
| US3341602A (en) * | 1965-02-10 | 1967-09-12 | Allied Chem | Preparation of halogenated ketones |
| US4021489A (en) * | 1975-12-08 | 1977-05-03 | E. I. Du Pont De Nemours And Company | Reaction of sulfur trioxide with cyclic (4- and 5-membered ring) fluorovinylethers |
| DE2623836C3 (de) * | 1976-05-28 | 1978-12-21 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von Quadratsäure |
-
1978
- 1978-03-10 DE DE2810398A patent/DE2810398C2/de not_active Expired
-
1979
- 1979-02-28 FR FR7905261A patent/FR2419270A1/fr active Granted
- 1979-03-08 IT IT48271/79A patent/IT1114557B/it active
- 1979-03-09 US US06/019,205 patent/US4272633A/en not_active Expired - Lifetime
- 1979-03-09 GB GB7908351A patent/GB2018748B/en not_active Expired
- 1979-03-09 JP JP2681979A patent/JPS54128548A/ja active Granted
- 1979-03-09 NL NL7901912A patent/NL7901912A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2419270A1 (fr) | 1979-10-05 |
| NL7901912A (nl) | 1979-09-12 |
| GB2018748B (en) | 1982-08-25 |
| IT7948271A0 (it) | 1979-03-08 |
| GB2018748A (en) | 1979-10-24 |
| JPS6130647B2 (enExample) | 1986-07-15 |
| JPS54128548A (en) | 1979-10-05 |
| IT1114557B (it) | 1986-01-27 |
| FR2419270B1 (enExample) | 1984-04-27 |
| US4272633A (en) | 1981-06-09 |
| DE2810398A1 (de) | 1979-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C 49/687 |
|
| 8126 | Change of the secondary classification |
Ipc: C07C 45/43 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8339 | Ceased/non-payment of the annual fee |