DE1468405B1 - Verfahren zur Herstellung von Fluor enthaltenden aromatischen Perhalogenkohlenstoffen - Google Patents
Verfahren zur Herstellung von Fluor enthaltenden aromatischen PerhalogenkohlenstoffenInfo
- Publication number
- DE1468405B1 DE1468405B1 DE19631468405D DE1468405DA DE1468405B1 DE 1468405 B1 DE1468405 B1 DE 1468405B1 DE 19631468405 D DE19631468405 D DE 19631468405D DE 1468405D A DE1468405D A DE 1468405DA DE 1468405 B1 DE1468405 B1 DE 1468405B1
- Authority
- DE
- Germany
- Prior art keywords
- fluorine
- fluoride
- compounds
- preparation
- perhalocarbons
- 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.)
- Pending
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims description 11
- 239000011737 fluorine Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 10
- 125000003118 aryl group Chemical group 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000460 chlorine Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000002222 fluorine compounds Chemical class 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 16
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 12
- 238000003682 fluorination reaction Methods 0.000 description 10
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 10
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 9
- 239000011698 potassium fluoride Substances 0.000 description 8
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 235000003270 potassium fluoride Nutrition 0.000 description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical class 0.000 description 4
- HGLRKPSTNKQNIS-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-fluorobenzene Chemical compound FC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HGLRKPSTNKQNIS-UHFFFAOYSA-N 0.000 description 3
- BYDZRYBEVBQSAC-UHFFFAOYSA-N 1,2,3-trichloro-4,5,6-trifluorobenzene Chemical compound FC1=C(F)C(Cl)=C(Cl)C(Cl)=C1F BYDZRYBEVBQSAC-UHFFFAOYSA-N 0.000 description 3
- OZRCFSKDIYWITR-UHFFFAOYSA-N 1,2-dichloro-3,4,5,6-tetrafluorobenzene Chemical compound FC1=C(F)C(F)=C(Cl)C(Cl)=C1F OZRCFSKDIYWITR-UHFFFAOYSA-N 0.000 description 3
- KGCDGLXSBHJAHZ-UHFFFAOYSA-N 1-chloro-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Cl)C(F)=C1F KGCDGLXSBHJAHZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910001512 metal fluoride Inorganic materials 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 235000013024 sodium fluoride Nutrition 0.000 description 3
- 239000011775 sodium fluoride Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JDCMOHAFGDQQJX-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octafluoronaphthalene Chemical compound FC1=C(F)C(F)=C(F)C2=C(F)C(F)=C(F)C(F)=C21 JDCMOHAFGDQQJX-UHFFFAOYSA-N 0.000 description 2
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 2
- ARUSRVIAMUGRDU-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,6-difluorobenzene Chemical compound FC1=C(F)C(Cl)=C(Cl)C(Cl)=C1Cl ARUSRVIAMUGRDU-UHFFFAOYSA-N 0.000 description 2
- GDILNOCXGTYXTN-UHFFFAOYSA-N 2-chloro-1-fluoronaphthalene Chemical class C1=CC=C2C(F)=C(Cl)C=CC2=C1 GDILNOCXGTYXTN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- -1 dichlorotetrafluorobenzene fluorobenzene Chemical compound 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RTNLUFLDZOAXIC-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octachloronaphthalene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C21 RTNLUFLDZOAXIC-UHFFFAOYSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 240000004093 Mitragyna parvifolia Species 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 150000005288 chlorofluorobenzenes Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- ONXPZLFXDMAPRO-UHFFFAOYSA-N decachlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl ONXPZLFXDMAPRO-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB40028/62A GB995927A (en) | 1962-10-23 | 1962-10-23 | Fluorination of perhalo compounds |
| GB20363 | 1963-01-02 | ||
| NL6401068A NL6401068A (enExample) | 1962-10-23 | 1964-02-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468405B1 true DE1468405B1 (de) | 1971-04-15 |
Family
ID=27253681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631468405D Pending DE1468405B1 (de) | 1962-10-23 | 1963-10-22 | Verfahren zur Herstellung von Fluor enthaltenden aromatischen Perhalogenkohlenstoffen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3300537A (enExample) |
| BE (1) | BE643855A (enExample) |
| CH (1) | CH448986A (enExample) |
| DE (1) | DE1468405B1 (enExample) |
| GB (1) | GB995927A (enExample) |
| NL (1) | NL6401068A (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1047062A (en) * | 1964-03-20 | 1966-11-02 | Imp Smelting Corp Ltd | Fluorination of halogenated organic compounds |
| GB1094182A (en) * | 1964-02-26 | 1967-12-06 | Imp Smelting Corp Ltd | Fluorination of halogenated organic compounds |
| GB1058406A (en) * | 1965-01-04 | 1967-02-08 | Imp Smelting Corp Ltd | Process for the preparation of fluorinated aromatic compounds |
| US3408412A (en) * | 1966-09-15 | 1968-10-29 | Texaco Inc | Method of preparing fluorobenzenes |
| US5502235A (en) * | 1994-12-28 | 1996-03-26 | Dowelanco | Solventless process for making 2,6 difluorobenzonitrile |
| US5824827A (en) * | 1996-11-22 | 1998-10-20 | Albemarle Corporation | Halogen exchange reactions |
| DE69711220T2 (de) | 1996-11-22 | 2002-10-31 | Albemarle Corp., Baton Rouge | Halogenaustausch-reaktionen und ihre anwendungen |
| US5789631A (en) * | 1996-11-25 | 1998-08-04 | Albemarle Corporation | Production of perhalobenzenes |
| US5965781A (en) * | 1997-11-21 | 1999-10-12 | Albemarle Corporation | Catalysis in halogen exchange reactions |
| CN112098564B (zh) * | 2020-10-15 | 2022-03-25 | 江苏新河农用化工有限公司 | 一种同时检测百菌清中六氯苯和十氯联苯的hplc检测方法 |
-
1962
- 1962-10-23 GB GB40028/62A patent/GB995927A/en not_active Expired
-
1963
- 1963-10-21 US US317805A patent/US3300537A/en not_active Expired - Lifetime
- 1963-10-22 DE DE19631468405D patent/DE1468405B1/de active Pending
- 1963-10-22 CH CH1294363A patent/CH448986A/de unknown
-
1964
- 1964-02-10 NL NL6401068A patent/NL6401068A/xx unknown
- 1964-02-14 BE BE643855A patent/BE643855A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE643855A (enExample) | 1964-05-29 |
| NL6401068A (enExample) | 1965-08-11 |
| US3300537A (en) | 1967-01-24 |
| GB995927A (en) | 1965-06-23 |
| CH448986A (de) | 1967-12-31 |
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