DE2057398B2 - Verfahren zur Herstellung von Halogenderivaten des Methans - Google Patents
Verfahren zur Herstellung von Halogenderivaten des MethansInfo
- Publication number
- DE2057398B2 DE2057398B2 DE2057398A DE2057398A DE2057398B2 DE 2057398 B2 DE2057398 B2 DE 2057398B2 DE 2057398 A DE2057398 A DE 2057398A DE 2057398 A DE2057398 A DE 2057398A DE 2057398 B2 DE2057398 B2 DE 2057398B2
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- hydrogen fluoride
- products
- compounds
- reaction
- 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
- 238000000034 method Methods 0.000 title claims description 7
- -1 halogen derivatives of methane Chemical class 0.000 title claims description 5
- 229910052736 halogen Inorganic materials 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000460 chlorine Substances 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 23
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 23
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 239000002699 waste material Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 241000252505 Characidae Species 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 36
- 239000007788 liquid Substances 0.000 description 13
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical class ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 11
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 5
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 5
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940029284 trichlorofluoromethane Drugs 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 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 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 2
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical class CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 description 1
- MHGNMCJZSOSEJB-UHFFFAOYSA-N 1,2,3,4,5,6-hexachlorobenzene;1,1,1,2,2,2-hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl.ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl MHGNMCJZSOSEJB-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DUDKKPVINWLFBI-UHFFFAOYSA-N 1-chlorobut-1-ene Chemical class CCC=CCl DUDKKPVINWLFBI-UHFFFAOYSA-N 0.000 description 1
- 101100190464 Caenorhabditis elegans pid-2 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MNAMVVANXDKFMG-UHFFFAOYSA-N [F].CCl Chemical class [F].CCl MNAMVVANXDKFMG-UHFFFAOYSA-N 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 229960002809 lindane Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2057398A DE2057398B2 (de) | 1970-11-21 | 1970-11-21 | Verfahren zur Herstellung von Halogenderivaten des Methans |
| CA127,605A CA956652A (en) | 1970-11-21 | 1971-11-15 | Process for the preparation of halogen derivatives of methane |
| NL7115772A NL7115772A (enrdf_load_stackoverflow) | 1970-11-21 | 1971-11-16 | |
| ZA717757A ZA717757B (en) | 1970-11-21 | 1971-11-18 | Process for the preparation of halogen derivatives of methane |
| AU35876/71A AU452223B2 (en) | 1970-11-21 | 1971-11-18 | Process for preparation of halogen derivatives of methane |
| BR7687/71A BR7107687D0 (pt) | 1970-11-21 | 1971-11-18 | Processo para preparacao de derivados halogenados do metano |
| CH1679871A CH562181A5 (enrdf_load_stackoverflow) | 1970-11-21 | 1971-11-18 | |
| BE775569A BE775569A (fr) | 1970-11-21 | 1971-11-19 | Procede de preparation de derives halogenes du |
| GB5383971A GB1359865A (en) | 1970-11-21 | 1971-11-19 | Process for the preparation of halogen derivatives of methane |
| FR7141500A FR2115281B1 (enrdf_load_stackoverflow) | 1970-11-21 | 1971-11-19 | |
| IT31336/71A IT940713B (it) | 1970-11-21 | 1971-11-19 | Processo per la preparazione di alogenoderivati del metan |
| SU1716544A SU431665A3 (enrdf_load_stackoverflow) | 1970-11-21 | 1971-11-19 | |
| JP9277171A JPS5544052B1 (enrdf_load_stackoverflow) | 1970-11-21 | 1971-11-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2057398A DE2057398B2 (de) | 1970-11-21 | 1970-11-21 | Verfahren zur Herstellung von Halogenderivaten des Methans |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2057398A1 DE2057398A1 (de) | 1972-06-15 |
| DE2057398B2 true DE2057398B2 (de) | 1974-03-07 |
| DE2057398C3 DE2057398C3 (enrdf_load_stackoverflow) | 1974-10-10 |
Family
ID=5788808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2057398A Granted DE2057398B2 (de) | 1970-11-21 | 1970-11-21 | Verfahren zur Herstellung von Halogenderivaten des Methans |
Country Status (13)
-
1970
- 1970-11-21 DE DE2057398A patent/DE2057398B2/de active Granted
-
1971
- 1971-11-15 CA CA127,605A patent/CA956652A/en not_active Expired
- 1971-11-16 NL NL7115772A patent/NL7115772A/xx not_active Application Discontinuation
- 1971-11-18 ZA ZA717757A patent/ZA717757B/xx unknown
- 1971-11-18 AU AU35876/71A patent/AU452223B2/en not_active Expired
- 1971-11-18 BR BR7687/71A patent/BR7107687D0/pt unknown
- 1971-11-18 CH CH1679871A patent/CH562181A5/xx not_active IP Right Cessation
- 1971-11-19 IT IT31336/71A patent/IT940713B/it active
- 1971-11-19 GB GB5383971A patent/GB1359865A/en not_active Expired
- 1971-11-19 SU SU1716544A patent/SU431665A3/ru active
- 1971-11-19 BE BE775569A patent/BE775569A/xx unknown
- 1971-11-19 FR FR7141500A patent/FR2115281B1/fr not_active Expired
- 1971-11-20 JP JP9277171A patent/JPS5544052B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT940713B (it) | 1973-02-20 |
| DE2057398C3 (enrdf_load_stackoverflow) | 1974-10-10 |
| SU431665A3 (enrdf_load_stackoverflow) | 1974-06-05 |
| ZA717757B (en) | 1972-08-30 |
| DE2057398A1 (de) | 1972-06-15 |
| GB1359865A (en) | 1974-07-10 |
| BE775569A (fr) | 1972-05-19 |
| CA956652A (en) | 1974-10-22 |
| CH562181A5 (enrdf_load_stackoverflow) | 1975-05-30 |
| JPS5544052B1 (enrdf_load_stackoverflow) | 1980-11-10 |
| NL7115772A (enrdf_load_stackoverflow) | 1972-05-24 |
| FR2115281B1 (enrdf_load_stackoverflow) | 1976-03-26 |
| BR7107687D0 (pt) | 1973-05-31 |
| FR2115281A1 (enrdf_load_stackoverflow) | 1972-07-07 |
| AU3587671A (en) | 1973-05-24 |
| AU452223B2 (en) | 1974-08-29 |
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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 | ||
| 8339 | Ceased/non-payment of the annual fee |