DE2038464C3 - Verfahren zur Herstellung von Halogenderivaten des Methans - Google Patents
Verfahren zur Herstellung von Halogenderivaten des MethansInfo
- Publication number
- DE2038464C3 DE2038464C3 DE2038464A DE2038464A DE2038464C3 DE 2038464 C3 DE2038464 C3 DE 2038464C3 DE 2038464 A DE2038464 A DE 2038464A DE 2038464 A DE2038464 A DE 2038464A DE 2038464 C3 DE2038464 C3 DE 2038464C3
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- amount
- carbon tetrachloride
- fluorine
- products
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 229910052736 halogen Inorganic materials 0.000 title claims description 4
- -1 halogen derivatives of methane Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000000460 chlorine Substances 0.000 claims description 34
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 17
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 150000002222 fluorine compounds Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002699 waste material Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229940029284 trichlorofluoromethane Drugs 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical class FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MNAMVVANXDKFMG-UHFFFAOYSA-N [F].CCl Chemical class [F].CCl MNAMVVANXDKFMG-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- IMRYETFJNLKUHK-UHFFFAOYSA-N traseolide Chemical compound CC1=C(C(C)=O)C=C2C(C(C)C)C(C)C(C)(C)C2=C1 IMRYETFJNLKUHK-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038464A DE2038464C3 (de) | 1970-08-03 | 1970-08-03 | Verfahren zur Herstellung von Halogenderivaten des Methans |
| CA119,286A CA955267A (en) | 1970-08-03 | 1971-07-28 | Process for the preparation of halogen derivatives of methane |
| NL7110484A NL7110484A (enrdf_load_stackoverflow) | 1970-08-03 | 1971-07-29 | |
| CH1120571A CH553140A (de) | 1970-08-03 | 1971-07-29 | Verfahren zur herstellung von halogenderivaten des methans. |
| BE770756A BE770756A (fr) | 1970-08-03 | 1971-07-30 | Procede de preparation de derives halogenes du |
| ZA715113A ZA715113B (en) | 1970-08-03 | 1971-08-02 | Process for the preparation of halogen derivatives of methane |
| JP5757771A JPS5544051B1 (enrdf_load_stackoverflow) | 1970-08-03 | 1971-08-02 | |
| GB3625871A GB1322614A (en) | 1970-08-03 | 1971-08-02 | Process for the preparation of halogen derivatives of methane |
| AU31881/71A AU460525B2 (en) | 1970-08-03 | 1971-08-02 | Process forthe preparation of halogen derivatives of methane |
| BR4920/71A BR7104920D0 (pt) | 1970-08-03 | 1971-08-02 | Processo para preparacao de derivados halogenados do metano |
| SU1689941A SU450395A3 (ru) | 1970-08-03 | 1971-08-03 | Способ получени галогенпроизводных метана |
| FR7128415A FR2101200B1 (enrdf_load_stackoverflow) | 1970-08-03 | 1971-08-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2038464A DE2038464C3 (de) | 1970-08-03 | 1970-08-03 | Verfahren zur Herstellung von Halogenderivaten des Methans |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2038464A1 DE2038464A1 (de) | 1972-02-10 |
| DE2038464B2 DE2038464B2 (de) | 1974-02-28 |
| DE2038464C3 true DE2038464C3 (de) | 1974-09-26 |
Family
ID=5778722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2038464A Expired DE2038464C3 (de) | 1970-08-03 | 1970-08-03 | Verfahren zur Herstellung von Halogenderivaten des Methans |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019131114A1 (ja) * | 2017-12-28 | 2019-07-04 | 昭和電工株式会社 | テトラフルオロメタンの製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1087873A (en) * | 1964-06-26 | 1967-10-18 | Laporte Chemical | Halogenation of branched-chain hydrocarbons |
| NL159080B (nl) * | 1967-10-13 | 1979-01-15 | Hoechst Ag | Werkwijze voor het bereiden van tetrachloorkoolstof. |
-
1970
- 1970-08-03 DE DE2038464A patent/DE2038464C3/de not_active Expired
-
1971
- 1971-07-28 CA CA119,286A patent/CA955267A/en not_active Expired
- 1971-07-29 CH CH1120571A patent/CH553140A/xx not_active IP Right Cessation
- 1971-07-29 NL NL7110484A patent/NL7110484A/xx not_active Application Discontinuation
- 1971-07-30 BE BE770756A patent/BE770756A/xx unknown
- 1971-08-02 BR BR4920/71A patent/BR7104920D0/pt unknown
- 1971-08-02 ZA ZA715113A patent/ZA715113B/xx unknown
- 1971-08-02 GB GB3625871A patent/GB1322614A/en not_active Expired
- 1971-08-02 JP JP5757771A patent/JPS5544051B1/ja active Pending
- 1971-08-03 SU SU1689941A patent/SU450395A3/ru active
- 1971-08-03 FR FR7128415A patent/FR2101200B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1322614A (en) | 1973-07-11 |
| AU3188171A (en) | 1973-02-08 |
| FR2101200A1 (enrdf_load_stackoverflow) | 1972-03-31 |
| CA955267A (en) | 1974-09-24 |
| DE2038464A1 (de) | 1972-02-10 |
| BE770756A (fr) | 1972-01-31 |
| NL7110484A (enrdf_load_stackoverflow) | 1972-02-07 |
| ZA715113B (en) | 1972-04-26 |
| DE2038464B2 (de) | 1974-02-28 |
| SU450395A3 (ru) | 1974-11-15 |
| CH553140A (de) | 1974-08-30 |
| FR2101200B1 (enrdf_load_stackoverflow) | 1975-10-10 |
| JPS5544051B1 (enrdf_load_stackoverflow) | 1980-11-10 |
| BR7104920D0 (pt) | 1973-06-14 |
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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 |