DE2100079B2 - Verfahren zur Herstellung eines Gemisches von Tetrachlorkohlenstoff und Perchlorathylen - Google Patents
Verfahren zur Herstellung eines Gemisches von Tetrachlorkohlenstoff und PerchlorathylenInfo
- Publication number
- DE2100079B2 DE2100079B2 DE2100079A DE2100079A DE2100079B2 DE 2100079 B2 DE2100079 B2 DE 2100079B2 DE 2100079 A DE2100079 A DE 2100079A DE 2100079 A DE2100079 A DE 2100079A DE 2100079 B2 DE2100079 B2 DE 2100079B2
- Authority
- DE
- Germany
- Prior art keywords
- perchlorethylene
- mixture
- carbon tetrachloride
- compounds
- reactor
- 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.)
- Granted
Links
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 title claims description 46
- 229950011008 tetrachloroethylene Drugs 0.000 title claims description 21
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 21
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical class ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- 238000005758 Endo reaction Methods 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 239000001273 butane Substances 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 229950005499 carbon tetrachloride Drugs 0.000 description 20
- 239000000047 product Substances 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- -1 C 4 hydrocarbons Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical class ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229960002809 lindane Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 1
- RPUFWOAXMFQSDJ-UHFFFAOYSA-N 1,1,2,3,3,4-hexachlorocyclopentane Chemical compound ClC1CC(Cl)(Cl)C(Cl)C1(Cl)Cl RPUFWOAXMFQSDJ-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical class C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- DUDKKPVINWLFBI-UHFFFAOYSA-N 1-chlorobut-1-ene Chemical compound CCC=CCl DUDKKPVINWLFBI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101150049168 Nisch gene Proteins 0.000 description 1
- 241000033695 Sige Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000011300 coal pitch Chemical group 0.000 description 1
- 239000011280 coal tar Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2100079A DE2100079B2 (de) | 1971-01-02 | 1971-01-02 | Verfahren zur Herstellung eines Gemisches von Tetrachlorkohlenstoff und Perchlorathylen |
| CA130,651A CA958034A (en) | 1971-01-02 | 1971-12-21 | Process for the preparation of a mixture of carbon tetrachloride and perchloroethylene |
| CS8915A CS172937B2 (enExample) | 1971-01-02 | 1971-12-22 | |
| ZA718591A ZA718591B (en) | 1971-01-02 | 1971-12-23 | Process for the preparation of a mixture of carbon tetracholoride and perchloroethylene |
| RO69180A RO61273A (enExample) | 1971-01-02 | 1971-12-24 | |
| NL7117955A NL7117955A (enExample) | 1971-01-02 | 1971-12-28 | |
| SU1732953A SU444355A3 (ru) | 1971-01-02 | 1971-12-30 | Способ получения четыреххлористого углерода |
| BR8669/71A BR7108669D0 (pt) | 1971-01-02 | 1971-12-30 | Processo para a obtencao de uma mistura de tetracloreto de carbono e percloroetileno |
| CH1919771A CH555792A (de) | 1971-01-02 | 1971-12-30 | Verfahren zur herstellung eines gemisches von tetrachlorkohlenstoff und perchloraethylen. |
| AU37418/71A AU464884B2 (en) | 1971-01-02 | 1971-12-30 | Process forthe preparation ofa mixture of carbon tetrachloride and perchlorethylene |
| IT33222/71A IT946167B (it) | 1971-01-02 | 1971-12-31 | Processo per la preparazione di una miscela di tetraclororo di carbonio e di percloroetilene |
| FR7200024A FR2120181A1 (enExample) | 1971-01-02 | 1972-01-03 | |
| BE777637A BE777637A (fr) | 1971-01-02 | 1972-01-03 | Procede de preparation d'un melange de tetrachlorure de carboneet de perchlorethylene |
| GB8072A GB1366221A (en) | 1971-01-02 | 1972-01-03 | Process for the production of carbon tetrachloride and perchloroe thylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2100079A DE2100079B2 (de) | 1971-01-02 | 1971-01-02 | Verfahren zur Herstellung eines Gemisches von Tetrachlorkohlenstoff und Perchlorathylen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2100079A1 DE2100079A1 (de) | 1972-11-30 |
| DE2100079B2 true DE2100079B2 (de) | 1973-10-11 |
| DE2100079C3 DE2100079C3 (enExample) | 1974-05-22 |
Family
ID=5795117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2100079A Granted DE2100079B2 (de) | 1971-01-02 | 1971-01-02 | Verfahren zur Herstellung eines Gemisches von Tetrachlorkohlenstoff und Perchlorathylen |
Country Status (14)
| Country | Link |
|---|---|
| AU (1) | AU464884B2 (enExample) |
| BE (1) | BE777637A (enExample) |
| BR (1) | BR7108669D0 (enExample) |
| CA (1) | CA958034A (enExample) |
| CH (1) | CH555792A (enExample) |
| CS (1) | CS172937B2 (enExample) |
| DE (1) | DE2100079B2 (enExample) |
| FR (1) | FR2120181A1 (enExample) |
| GB (1) | GB1366221A (enExample) |
| IT (1) | IT946167B (enExample) |
| NL (1) | NL7117955A (enExample) |
| RO (1) | RO61273A (enExample) |
| SU (1) | SU444355A3 (enExample) |
| ZA (1) | ZA718591B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2772371B1 (fr) * | 1997-12-15 | 2000-02-25 | Solvay | Procede pour la production de perchlorethylene |
-
1971
- 1971-01-02 DE DE2100079A patent/DE2100079B2/de active Granted
- 1971-12-21 CA CA130,651A patent/CA958034A/en not_active Expired
- 1971-12-22 CS CS8915A patent/CS172937B2/cs unknown
- 1971-12-23 ZA ZA718591A patent/ZA718591B/xx unknown
- 1971-12-24 RO RO69180A patent/RO61273A/ro unknown
- 1971-12-28 NL NL7117955A patent/NL7117955A/xx unknown
- 1971-12-30 BR BR8669/71A patent/BR7108669D0/pt unknown
- 1971-12-30 SU SU1732953A patent/SU444355A3/ru active
- 1971-12-30 CH CH1919771A patent/CH555792A/xx not_active IP Right Cessation
- 1971-12-30 AU AU37418/71A patent/AU464884B2/en not_active Expired
- 1971-12-31 IT IT33222/71A patent/IT946167B/it active
-
1972
- 1972-01-03 FR FR7200024A patent/FR2120181A1/fr not_active Withdrawn
- 1972-01-03 GB GB8072A patent/GB1366221A/en not_active Expired
- 1972-01-03 BE BE777637A patent/BE777637A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7108669D0 (pt) | 1973-05-17 |
| RO61273A (enExample) | 1976-09-15 |
| GB1366221A (en) | 1974-09-11 |
| ZA718591B (en) | 1972-09-27 |
| BE777637A (fr) | 1972-07-03 |
| DE2100079A1 (de) | 1972-11-30 |
| SU444355A3 (ru) | 1974-09-25 |
| NL7117955A (enExample) | 1972-07-04 |
| FR2120181A1 (enExample) | 1972-08-11 |
| IT946167B (it) | 1973-05-21 |
| CH555792A (de) | 1974-11-15 |
| AU464884B2 (en) | 1975-09-11 |
| CS172937B2 (enExample) | 1977-01-28 |
| DE2100079C3 (enExample) | 1974-05-22 |
| AU3741871A (en) | 1973-07-05 |
| CA958034A (en) | 1974-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |