DE1468396C3 - Verfahren zur Herstellung hoch fluorierter aromatischer oder olefinisch ungesättigter Verbindungen durch Dehalo genierung - Google Patents
Verfahren zur Herstellung hoch fluorierter aromatischer oder olefinisch ungesättigter Verbindungen durch Dehalo genierungInfo
- Publication number
- DE1468396C3 DE1468396C3 DE1468396A DE1468396A DE1468396C3 DE 1468396 C3 DE1468396 C3 DE 1468396C3 DE 1468396 A DE1468396 A DE 1468396A DE 1468396 A DE1468396 A DE 1468396A DE 1468396 C3 DE1468396 C3 DE 1468396C3
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- iii
- iron
- magnetite
- highly fluorinated
- 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 9
- 150000001875 compounds Chemical class 0.000 title claims description 8
- 125000003118 aryl group Chemical group 0.000 title claims description 4
- 238000005695 dehalogenation reaction Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 150000001491 aromatic compounds Chemical class 0.000 claims description 6
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- 229950011087 perflunafene Drugs 0.000 claims description 4
- UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical class C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- RKIMETXDACNTIE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F RKIMETXDACNTIE-UHFFFAOYSA-N 0.000 claims description 2
- SEEJHICDPXGSRQ-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(1,1,2,2,2-pentafluoroethyl)cyclohexane Chemical compound FC(F)(F)C(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F SEEJHICDPXGSRQ-UHFFFAOYSA-N 0.000 claims description 2
- QIROQPWSJUXOJC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QIROQPWSJUXOJC-UHFFFAOYSA-N 0.000 claims description 2
- VBUGTEWHVPJVOC-UHFFFAOYSA-N 1,1,2,2,3-pentachloro-3,4,4,5,5,6,6-heptafluorocyclohexane Chemical compound ClC1(C(C(C(C(C1(F)F)(F)F)(F)F)(F)Cl)(Cl)Cl)Cl VBUGTEWHVPJVOC-UHFFFAOYSA-N 0.000 claims description 2
- CQCLKKOYBYNMRG-UHFFFAOYSA-N 1,1,2,2-tetrachloro-3,3,4,4,5,5,6,6-octafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(Cl)(Cl)C(Cl)(Cl)C1(F)F CQCLKKOYBYNMRG-UHFFFAOYSA-N 0.000 claims description 2
- ZFFLXJVVPHACEG-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,6,6-decafluorocyclohexene Chemical compound FC1=C(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F ZFFLXJVVPHACEG-UHFFFAOYSA-N 0.000 claims description 2
- NYEZNHLGLOQHEE-UHFFFAOYSA-N 1,2,3,4,5,5,6,6-octafluorocyclohexa-1,3-diene Chemical class FC1=C(F)C(F)(F)C(F)(F)C(F)=C1F NYEZNHLGLOQHEE-UHFFFAOYSA-N 0.000 claims description 2
- PNTDDASKGOEYLF-UHFFFAOYSA-N 1,2,3,4,5,6-hexachloro-1,2,3,4,5,6-hexafluorocyclohexane Chemical compound FC1(Cl)C(F)(Cl)C(F)(Cl)C(F)(Cl)C(F)(Cl)C1(F)Cl PNTDDASKGOEYLF-UHFFFAOYSA-N 0.000 claims description 2
- BMFPHHLKGOOCHE-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(1,1,2,2,2-pentafluoroethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)C(F)(F)F)C(F)=C1F BMFPHHLKGOOCHE-UHFFFAOYSA-N 0.000 claims description 2
- GZQZKLFXWPAMFW-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(1,2,2-trifluoroethenyl)benzene Chemical compound FC(F)=C(F)C1=C(F)C(F)=C(F)C(F)=C1F GZQZKLFXWPAMFW-UHFFFAOYSA-N 0.000 claims description 2
- KGZKBHYAEBRMAR-UHFFFAOYSA-N 1-chloro-1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(Cl)C(F)(F)C1(F)F KGZKBHYAEBRMAR-UHFFFAOYSA-N 0.000 claims description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 2
- -1 aliphatic olefins Chemical class 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000292 calcium oxide Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LOQGSOTUHASIHI-UHFFFAOYSA-N perfluoro-1,3-dimethylcyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)C1(F)F LOQGSOTUHASIHI-UHFFFAOYSA-N 0.000 claims description 2
- HDRXJTRBIHARLO-UHFFFAOYSA-N 1,1-dichloro-2,2,3,3,4,4,5,5,6,6-decafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(Cl)(Cl)C(F)(F)C1(F)F HDRXJTRBIHARLO-UHFFFAOYSA-N 0.000 claims 1
- GPDKCNQUFLZMCS-UHFFFAOYSA-N [O+]Cl Chemical compound [O+]Cl GPDKCNQUFLZMCS-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000011324 bead Substances 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011651 chromium Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 238000006115 defluorination reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 3
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical compound FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910020599 Co 3 O 4 Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- FZGIHSNZYGFUGM-UHFFFAOYSA-L iron(ii) fluoride Chemical class [F-].[F-].[Fe+2] FZGIHSNZYGFUGM-UHFFFAOYSA-L 0.000 description 1
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1847262A GB1017815A (en) | 1962-05-14 | 1962-05-14 | Dehalogenation of organic compounds |
| GB1847162 | 1962-05-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1468396A1 DE1468396A1 (de) | 1968-12-19 |
| DE1468396B2 DE1468396B2 (de) | 1973-03-22 |
| DE1468396C3 true DE1468396C3 (de) | 1973-10-11 |
Family
ID=26253400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1468396A Expired DE1468396C3 (de) | 1962-05-14 | 1963-05-13 | Verfahren zur Herstellung hoch fluorierter aromatischer oder olefinisch ungesättigter Verbindungen durch Dehalo genierung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3268600A (en:Method) |
| BE (1) | BE646596A (en:Method) |
| CH (1) | CH437255A (en:Method) |
| DE (1) | DE1468396C3 (en:Method) |
| NL (1) | NL292631A (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3500617B2 (ja) * | 1993-08-27 | 2004-02-23 | ダイキン工業株式会社 | ヘキサフルオロシクロブタンの製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1904440A (en) * | 1930-03-06 | 1933-04-18 | Standard Oil Dev Co | Reactivation of catalyst used in the preparation of hydrogen |
| US2150270A (en) * | 1936-10-08 | 1939-03-14 | Durrans Thomas Harold | Revivification of catalysts for hydrogenation and like processes |
| US2599631A (en) * | 1945-12-06 | 1952-06-10 | Du Pont | Preparation of vinyl fluoride |
| US2478933A (en) * | 1947-04-02 | 1949-08-16 | Allied Chem & Dye Corp | Manufacture of 1, 1-chlorofluoroethylenes |
| US2695320A (en) * | 1950-08-28 | 1954-11-23 | Monsanto Chemicals | Vinyl fluoride preparation from 1, 2-difluoroethane |
| US2697124A (en) * | 1952-02-25 | 1954-12-14 | Kellogg M W Co | Dehalogenation of fluorohalocarbons |
| BE582515A (en:Method) * | 1958-09-11 | |||
| NL125669C (en:Method) * | 1958-11-05 | 1968-07-15 | ||
| US3043889A (en) * | 1960-03-22 | 1962-07-10 | Allied Chem | Production of fluoroethylenes |
| US3118005A (en) * | 1960-12-27 | 1964-01-14 | Attila E Pavlath | Titania catalyzed dehydrofluorination of 1, 1, 1-difluorochloro alkanes |
-
0
- NL NL292631D patent/NL292631A/xx unknown
-
1963
- 1963-05-13 DE DE1468396A patent/DE1468396C3/de not_active Expired
- 1963-05-14 US US280412A patent/US3268600A/en not_active Expired - Lifetime
- 1963-05-14 CH CH603363A patent/CH437255A/de unknown
-
1964
- 1964-04-15 BE BE646596A patent/BE646596A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE646596A (en:Method) | 1964-07-31 |
| CH437255A (de) | 1967-06-15 |
| US3268600A (en) | 1966-08-23 |
| NL292631A (en:Method) | |
| DE1468396A1 (de) | 1968-12-19 |
| DE1468396B2 (de) | 1973-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |