DE1229506B - Verfahren zur Herstellung von Perfluormonojodalkanen hoeheren Molekulargewichts aus den entsprechenden Perfluormonojodalkanen niederen Molekulargewichts - Google Patents
Verfahren zur Herstellung von Perfluormonojodalkanen hoeheren Molekulargewichts aus den entsprechenden Perfluormonojodalkanen niederen MolekulargewichtsInfo
- Publication number
- DE1229506B DE1229506B DEP33196A DEP0033196A DE1229506B DE 1229506 B DE1229506 B DE 1229506B DE P33196 A DEP33196 A DE P33196A DE P0033196 A DEP0033196 A DE P0033196A DE 1229506 B DE1229506 B DE 1229506B
- Authority
- DE
- Germany
- Prior art keywords
- iodide
- molecular weight
- parts
- perfluoromonoiodalkanes
- tetrafluoroethylene
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 29
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 25
- 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 8
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 7
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- NATNDLFLTYVBBB-UHFFFAOYSA-D [Sb](F)(F)(F)(F)F.[Sb](Cl)(Cl)(Cl)(Cl)Cl Chemical compound [Sb](F)(F)(F)(F)F.[Sb](Cl)(Cl)(Cl)(Cl)Cl NATNDLFLTYVBBB-UHFFFAOYSA-D 0.000 claims 1
- 239000000047 product Substances 0.000 description 20
- -1 hydrocarbon iodide Chemical class 0.000 description 18
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 11
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical compound FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 description 11
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 150000004694 iodide salts Chemical class 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 229910052787 antimony Inorganic materials 0.000 description 4
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 4
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BBZVTTKMXRPMHZ-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoro-2-iodopropane Chemical compound FC(F)(F)C(F)(I)C(F)(F)F BBZVTTKMXRPMHZ-UHFFFAOYSA-N 0.000 description 1
- VRJGWRPPKVEMMR-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-8-iodo-2-(trifluoromethyl)octane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I VRJGWRPPKVEMMR-UHFFFAOYSA-N 0.000 description 1
- OUFXTVSYOAPUKM-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6-dodecafluoro-6-iodo-2-(trifluoromethyl)hexane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I OUFXTVSYOAPUKM-UHFFFAOYSA-N 0.000 description 1
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 1
- ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
- FHQCFGPKNSSISL-UHFFFAOYSA-N 1-iodotetradecane Chemical compound CCCCCCCCCCCCCCI FHQCFGPKNSSISL-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US246024A US3234294A (en) | 1962-12-20 | 1962-12-20 | Process for the preparation of perfluorocarbon iodides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1229506B true DE1229506B (de) | 1966-12-01 |
Family
ID=22929031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP33196A Pending DE1229506B (de) | 1962-12-20 | 1963-12-14 | Verfahren zur Herstellung von Perfluormonojodalkanen hoeheren Molekulargewichts aus den entsprechenden Perfluormonojodalkanen niederen Molekulargewichts |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3234294A (en:Method) |
| BE (1) | BE641569A (en:Method) |
| CH (1) | CH444833A (en:Method) |
| DE (1) | DE1229506B (en:Method) |
| FR (1) | FR1385682A (en:Method) |
| GB (1) | GB998668A (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2002062735A1 (fr) * | 2001-02-07 | 2002-08-15 | Daikin Industries, Ltd. | Procede de preparation d'un melange de telomeres de iodure de fluoroalkyle et procede de preparation d'un ester de (meth)acrylate contenant du fluor |
| US8258354B2 (en) | 2010-06-08 | 2012-09-04 | E. I. Du Pont De Nemours And Company | Producing short chain perfluoroalkyl iodides |
| CN107108410B (zh) | 2014-10-30 | 2021-02-05 | 科慕埃弗西有限公司 | 由高阶调聚物制备短链全氟烷基碘 |
| CN107602733B (zh) * | 2017-10-13 | 2019-08-27 | 山东东岳高分子材料有限公司 | 一种含氟乳化剂以及利用等离子体制备含氟乳化剂的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3006973A (en) * | 1959-05-01 | 1961-10-31 | Pennsalt Chemicals Corp | Halogenated organic compounds |
| US3132185A (en) * | 1962-05-02 | 1964-05-05 | Du Pont | Improvement in the preparation of perfluoroalkyl iodides from tetrafluoroethylene |
-
1962
- 1962-12-20 US US246024A patent/US3234294A/en not_active Expired - Lifetime
-
1963
- 1963-12-14 DE DEP33196A patent/DE1229506B/de active Pending
- 1963-12-19 CH CH1566063A patent/CH444833A/de unknown
- 1963-12-19 BE BE641569A patent/BE641569A/xx unknown
- 1963-12-19 FR FR957853A patent/FR1385682A/fr not_active Expired
- 1963-12-19 GB GB50162/63A patent/GB998668A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3234294A (en) | 1966-02-08 |
| GB998668A (en) | 1965-07-21 |
| BE641569A (en:Method) | 1964-06-19 |
| FR1385682A (fr) | 1965-01-15 |
| CH444833A (de) | 1967-10-15 |
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