CH477385A - Verfahren zur Herstellung von Perfluoräthyljodiden - Google Patents
Verfahren zur Herstellung von PerfluoräthyljodidenInfo
- Publication number
- CH477385A CH477385A CH1266263A CH1266263A CH477385A CH 477385 A CH477385 A CH 477385A CH 1266263 A CH1266263 A CH 1266263A CH 1266263 A CH1266263 A CH 1266263A CH 477385 A CH477385 A CH 477385A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- tetrafluoroethylene
- iodine
- reaction
- moles
- Prior art date
Links
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical class FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 80
- CEBDXRXVGUQZJK-UHFFFAOYSA-N 2-methyl-1-benzofuran-7-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2OC(C)=CC2=C1 CEBDXRXVGUQZJK-UHFFFAOYSA-N 0.000 claims description 27
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 27
- 229910052740 iodine Inorganic materials 0.000 claims description 27
- 239000011630 iodine Substances 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 21
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 claims description 15
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 claims description 13
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 5
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 5
- DAOANAATJZWTSJ-UHFFFAOYSA-N N-Decanoylmorpholine Chemical compound CCCCCCCCCC(=O)N1CCOCC1 DAOANAATJZWTSJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 53
- 239000000047 product Substances 0.000 description 29
- -1 perfluoroalkyl iodides Chemical class 0.000 description 17
- 238000007792 addition Methods 0.000 description 11
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 8
- 235000019407 octafluorocyclobutane Nutrition 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- NZXVPCQHQVWOFD-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1,2-diiodoethane Chemical compound FC(F)(I)C(F)(F)I NZXVPCQHQVWOFD-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 3
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 2
- 229960002799 stannous fluoride Drugs 0.000 description 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CJGCSCCKQJWTQF-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-2,2-diiodoethane Chemical compound FC(F)(F)C(F)(I)I CJGCSCCKQJWTQF-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical class FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910021582 Cobalt(II) fluoride Inorganic materials 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910021587 Nickel(II) fluoride Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- GVFOJDIFWSDNOY-UHFFFAOYSA-N antimony tin Chemical compound [Sn].[Sb] GVFOJDIFWSDNOY-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
- C07C17/281—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons of only one compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US191722A US3132185A (en) | 1962-05-02 | 1962-05-02 | Improvement in the preparation of perfluoroalkyl iodides from tetrafluoroethylene |
| GB37291/63A GB998235A (en) | 1962-05-02 | 1963-09-23 | Process for preparing perfluoroalkyl iodides |
| FR949248A FR1380555A (fr) | 1962-05-02 | 1963-10-01 | Procédé de préparation d'iodure de perfluoroalcoyle |
| DE1963P0032721 DE1292641C2 (de) | 1962-05-02 | 1963-10-05 | Verfahren zur herstellung von perfluoralkyljodiden |
| CH1266263A CH477385A (de) | 1962-05-02 | 1963-10-15 | Verfahren zur Herstellung von Perfluoräthyljodiden |
| CH406269A CH486402A (de) | 1962-05-02 | 1963-10-15 | Verfahren zur Herstellung von Perfluoralkyljodiden |
| BE640970D BE640970A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1962-05-02 | 1963-12-09 |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US191722A US3132185A (en) | 1962-05-02 | 1962-05-02 | Improvement in the preparation of perfluoroalkyl iodides from tetrafluoroethylene |
| GB37291/63A GB998235A (en) | 1962-05-02 | 1963-09-23 | Process for preparing perfluoroalkyl iodides |
| FR949248A FR1380555A (fr) | 1962-05-02 | 1963-10-01 | Procédé de préparation d'iodure de perfluoroalcoyle |
| DE1963P0032721 DE1292641C2 (de) | 1962-05-02 | 1963-10-05 | Verfahren zur herstellung von perfluoralkyljodiden |
| CH1266263A CH477385A (de) | 1962-05-02 | 1963-10-15 | Verfahren zur Herstellung von Perfluoräthyljodiden |
| BE640970T | 1963-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH477385A true CH477385A (de) | 1969-08-31 |
Family
ID=88469874
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1266263A CH477385A (de) | 1962-05-02 | 1963-10-15 | Verfahren zur Herstellung von Perfluoräthyljodiden |
| CH406269A CH486402A (de) | 1962-05-02 | 1963-10-15 | Verfahren zur Herstellung von Perfluoralkyljodiden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH406269A CH486402A (de) | 1962-05-02 | 1963-10-15 | Verfahren zur Herstellung von Perfluoralkyljodiden |
Country Status (6)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234294A (en) * | 1962-12-20 | 1966-02-08 | Du Pont | Process for the preparation of perfluorocarbon iodides |
| US3406214A (en) * | 1964-08-08 | 1968-10-15 | Fmc Corp | Method of preparing perfluoroethyl iodide |
| FR1482092A (fr) * | 1966-03-29 | 1967-05-26 | Electrochimie Soc | Procédé de préparation d'iodofluoroalcanes |
| GB1242712A (en) * | 1968-04-24 | 1971-08-11 | Ici Ltd | Preparation of perfluoroalkyl iodides |
| DE2150096C3 (de) * | 1970-10-09 | 1984-10-11 | Asahi Glass Co. Ltd., Tokio/Tokyo | Verfahren zur Herstellung von Perfluoralkyljodiden |
| US6525231B1 (en) | 1992-10-22 | 2003-02-25 | E. I. Du Pont De Nemours And Company | Producing hydrofluoro compounds by hydrogenolysis of iodides |
| EP0711264B1 (en) * | 1993-07-29 | 1998-10-14 | E.I. Du Pont De Nemours And Company | Process for the preparation of perfluoroalkyl iodide |
| US5574193A (en) * | 1994-05-26 | 1996-11-12 | E. I. Du Pont De Nemours And Company | Initiators for telomerization of polyfluoroalkyl iodides with fluoroolefins |
| US5908966A (en) * | 1997-10-14 | 1999-06-01 | E. I. Du Pont De Nemours And Company | Thermal process for the preparation of a telomeric alkyl iodide |
| RU2144019C1 (ru) * | 1999-07-20 | 2000-01-10 | Открытое акционерное общество "Галоген" | Способ получения пентафторйодэтана |
| US8258354B2 (en) | 2010-06-08 | 2012-09-04 | E. I. Du Pont De Nemours And Company | Producing short chain perfluoroalkyl iodides |
| CN102241561B (zh) * | 2011-05-12 | 2012-05-30 | 山东中氟化工科技有限公司 | 一步法制备全氟烷基碘的方法 |
| WO2016069429A1 (en) | 2014-10-30 | 2016-05-06 | The Chemours Company Fc, Llc | Production of short chain perfluoroalkyl iodides from higher order telomers |
| FR3107271B1 (fr) * | 2020-02-19 | 2022-12-16 | Arkema France | Procédé de production d’un composé iodofluoroalcane |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2614131A (en) * | 1949-08-22 | 1952-10-14 | Minnesota Mining & Mfg | Fluorocarbon mono-iodides and method of making |
| US3006973A (en) * | 1959-05-01 | 1961-10-31 | Pennsalt Chemicals Corp | Halogenated organic compounds |
-
1962
- 1962-05-02 US US191722A patent/US3132185A/en not_active Expired - Lifetime
-
1963
- 1963-09-23 GB GB37291/63A patent/GB998235A/en not_active Expired
- 1963-10-01 FR FR949248A patent/FR1380555A/fr not_active Expired
- 1963-10-05 DE DE1963P0032721 patent/DE1292641C2/de not_active Expired
- 1963-10-15 CH CH1266263A patent/CH477385A/de not_active IP Right Cessation
- 1963-10-15 CH CH406269A patent/CH486402A/de not_active IP Right Cessation
- 1963-12-09 BE BE640970D patent/BE640970A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3132185A (en) | 1964-05-05 |
| BE640970A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-04-01 |
| DE1292641B (de) | 1969-04-17 |
| GB998235A (en) | 1965-07-14 |
| CH486402A (de) | 1970-02-28 |
| DE1292641C2 (de) | 1974-01-24 |
| FR1380555A (fr) | 1964-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |