DE2207177A1 - Verfahren zur herstellung von perfluorcarbonsaeuren und deren fluoride - Google Patents
Verfahren zur herstellung von perfluorcarbonsaeuren und deren fluorideInfo
- Publication number
- DE2207177A1 DE2207177A1 DE2207177A DE2207177A DE2207177A1 DE 2207177 A1 DE2207177 A1 DE 2207177A1 DE 2207177 A DE2207177 A DE 2207177A DE 2207177 A DE2207177 A DE 2207177A DE 2207177 A1 DE2207177 A1 DE 2207177A1
- Authority
- DE
- Germany
- Prior art keywords
- iodine
- acids
- reaction
- perfluorocarboxylic
- extracted
- 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 18
- 238000004519 manufacturing process Methods 0.000 title description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical class FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- -1 carboxylic acid fluorides Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 239000011630 iodine Substances 0.000 claims description 19
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical class FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 3
- 229960001763 zinc sulfate Drugs 0.000 claims description 3
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KWXGJTSJUKTDQU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I KWXGJTSJUKTDQU-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- ZWBAMYVPMDSJGQ-UHFFFAOYSA-N perfluoroheptanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZWBAMYVPMDSJGQ-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B13/00—Oxygen; Ozone; Oxides or hydroxides in general
- C01B13/02—Preparation of oxygen
- C01B13/0229—Purification or separation processes
- C01B13/0248—Physical processing only
- C01B13/0259—Physical processing only by adsorption on solids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Analytical Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207177A DE2207177A1 (de) | 1972-02-16 | 1972-02-16 | Verfahren zur herstellung von perfluorcarbonsaeuren und deren fluoride |
| NLAANVRAGE7210721,A NL175589B (nl) | 1972-02-16 | 1972-08-04 | Werkwijze voor het met zuurstof verrijken van zuurstof-bevattende gassen door adsorptie aan moleculair zeefcokes. |
| NL7300249A NL7300249A (https=) | 1972-02-16 | 1973-01-08 | |
| GB249773A GB1361951A (en) | 1972-02-16 | 1973-01-17 | Process for the production of perfluorocarboxylic acids and their fluorides |
| BE794223D BE794223A (fr) | 1972-02-16 | 1973-01-18 | Procede de production d'acides perfluorocarboxyliques et de leurs fluorures |
| FR7302493A FR2172105B1 (https=) | 1972-02-16 | 1973-01-24 | |
| US329188A US3862971A (en) | 1972-02-16 | 1973-02-02 | Process for making perfluorocarboxylic acids and fluorides thereof |
| IT20384/73A IT979105B (it) | 1972-02-16 | 1973-02-14 | Procedimento per la preparazione di acidi perfluorocarbossilici e dei loro fluoruri |
| JP48019129A JPS4892322A (https=) | 1972-02-16 | 1973-02-16 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207177A DE2207177A1 (de) | 1972-02-16 | 1972-02-16 | Verfahren zur herstellung von perfluorcarbonsaeuren und deren fluoride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2207177A1 true DE2207177A1 (de) | 1973-08-23 |
Family
ID=5836075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2207177A Pending DE2207177A1 (de) | 1972-02-16 | 1972-02-16 | Verfahren zur herstellung von perfluorcarbonsaeuren und deren fluoride |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3862971A (https=) |
| JP (1) | JPS4892322A (https=) |
| BE (1) | BE794223A (https=) |
| DE (1) | DE2207177A1 (https=) |
| FR (1) | FR2172105B1 (https=) |
| GB (1) | GB1361951A (https=) |
| IT (1) | IT979105B (https=) |
| NL (2) | NL175589B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052285A1 (de) * | 1980-11-15 | 1982-05-26 | Hoechst Aktiengesellschaft | Verfahren zur Reindarstellung gesättigter Perfluoralkancarbonsäuren(1) aus 1-Iodperfluoralkanen |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4181678A (en) * | 1978-09-15 | 1980-01-01 | The United States Of America As Represented By The Secretary Of The Air Force | Symmetrical perfluoroalkylene oxide α,ω-diacyl fluorides |
| US4181679A (en) * | 1978-10-24 | 1980-01-01 | The United States Of America As Represented By The Secretary Of The Air Force | ω-Iodoperfluoroalkylene oxide acyl fluorides |
| JPS6056126B2 (ja) * | 1980-08-26 | 1985-12-09 | 旭硝子株式会社 | ジフルオロハロアセチルフルオリドの製造方法 |
| US5504248A (en) * | 1994-07-28 | 1996-04-02 | E. I. Du Pont De Nemours And Company | Preparation of halogenated compounds |
| US5723630A (en) * | 1997-02-18 | 1998-03-03 | Minnesota Mining And Manufacturing Company | Process for preparing fluorinated beta-sultones |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3102139A (en) * | 1958-05-08 | 1963-08-27 | Pennsalt Chemicals Corp | Oxidation process for preparing carboxylic acid anhydrides |
| US3351644A (en) * | 1962-07-24 | 1967-11-07 | Pennsalt Chemicals Corp | Preparation of telomeric acid fluorides |
-
1972
- 1972-02-16 DE DE2207177A patent/DE2207177A1/de active Pending
- 1972-08-04 NL NLAANVRAGE7210721,A patent/NL175589B/xx not_active IP Right Cessation
-
1973
- 1973-01-08 NL NL7300249A patent/NL7300249A/xx unknown
- 1973-01-17 GB GB249773A patent/GB1361951A/en not_active Expired
- 1973-01-18 BE BE794223D patent/BE794223A/xx unknown
- 1973-01-24 FR FR7302493A patent/FR2172105B1/fr not_active Expired
- 1973-02-02 US US329188A patent/US3862971A/en not_active Expired - Lifetime
- 1973-02-14 IT IT20384/73A patent/IT979105B/it active
- 1973-02-16 JP JP48019129A patent/JPS4892322A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052285A1 (de) * | 1980-11-15 | 1982-05-26 | Hoechst Aktiengesellschaft | Verfahren zur Reindarstellung gesättigter Perfluoralkancarbonsäuren(1) aus 1-Iodperfluoralkanen |
Also Published As
| Publication number | Publication date |
|---|---|
| US3862971A (en) | 1975-01-28 |
| GB1361951A (en) | 1974-07-30 |
| BE794223A (fr) | 1973-05-16 |
| NL7300249A (https=) | 1973-08-20 |
| FR2172105A1 (https=) | 1973-09-28 |
| NL7210721A (https=) | 1973-08-20 |
| IT979105B (it) | 1974-09-30 |
| NL175589B (nl) | 1984-07-02 |
| JPS4892322A (https=) | 1973-11-30 |
| FR2172105B1 (https=) | 1977-07-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |