US3423299A - Electrochemical fluorination of polymethylene sulfones to produce perfluoroalkylsulfonyl fluorides - Google Patents
Electrochemical fluorination of polymethylene sulfones to produce perfluoroalkylsulfonyl fluorides Download PDFInfo
- Publication number
- US3423299A US3423299A US509210A US3423299DA US3423299A US 3423299 A US3423299 A US 3423299A US 509210 A US509210 A US 509210A US 3423299D A US3423299D A US 3423299DA US 3423299 A US3423299 A US 3423299A
- Authority
- US
- United States
- Prior art keywords
- produce
- cell
- electrochemical fluorination
- perfluoroalkylsulfonyl
- sulfone
- 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 - Lifetime
Links
- 238000003682 fluorination reaction Methods 0.000 title description 3
- 150000002222 fluorine compounds Chemical class 0.000 title description 3
- -1 polymethylene Polymers 0.000 title description 3
- 150000003457 sulfones Chemical class 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- 239000006193 liquid solution Substances 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 238000005868 electrolysis reaction Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 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 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000003385 ring cleavage reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Inorganic materials [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- CFRVORMUGQWQNZ-UHFFFAOYSA-N thiepane 1,1-dioxide Chemical class O=S1(=O)CCCCCC1 CFRVORMUGQWQNZ-UHFFFAOYSA-N 0.000 description 1
- NFLCXILSXXHXRW-UHFFFAOYSA-N thionane 1,1-dioxide Chemical compound O=S1(=O)CCCCCCCC1 NFLCXILSXXHXRW-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/27—Halogenation
- C25B3/28—Fluorination
Definitions
- U.S. Patent 2,519,983, issued to Simons discloses the electrochemical fluorination of organic materials with anhydrous hydrofluoric acid.
- US. Patent 2,732,398, issued to Brice and Trott discloses the use of the process of Simons to convert hydrocarbon sulfonyl halides into perfluoroalkylsulfonyl fluorides.
- compositions which are made by the reaction of the appropriate alpha-omega-diolefin (e.g. butadiene) with S0
- alpha-omega-diolefin e.g. butadiene
- S0 alpha-omega-diolefin
- the major advantage of the process of this invention is its relatively high yield of product, which renders it commercially desirable.
- the process is also unique in that the electrochemical fluorination process has never before been found to cause ring cleavage at a carbonsulfur linkage to form a perfluoroalkylsulfonyl fluoride.
- the conductivity of the alkylene sulfone-hydrogen fluoride solution is usually adequate to permit electrolysis at a sufliciently low voltage to prevent the evolution of elemental fluorine, which begins to form when about 10 to 12 volts are applied to a cell anode.
- conductivity additives such as sodium or potassium fluoride can be added, if desired.
- voltages of from 4 to 8 volts generally give the best results.
- the cathodes and anodes can be made of any conductive material which is not corroded by anhydrous HF, e.g., nickel, Monel, carbon, silicon carbide, etc.
- the cell was cooled to l0 C., and anhydrous HF vapor was added until about 3500 ml. of liquid HF were present in the cell.
- To this was added 1242.5 g. of tetramethylene sulfone, and the cell was operated for 5 days at about 0 C. with a direct current of about amperes and 5.5 volts.
- EXAMPLE 2 When an electrochemical cell, fitted with a graphite anode and cathode and the same condenser as in Example l is filled with 1 kg. of octamethylene sulfone and 2 kg. of liquid HF, electrolysis for several days at 10 C. at a voltage of 7 volts produces a liberal yield of nperfluorooctylsulfonyl fluoride.
- Electrolysis was initiated at 10 C., and an average current of 85 amperes and 5.5 volts was maintained for 48 hours with an average temperature of C. At the end of the period, the current began to decrease. When it had fallen to 15 amperes, the electrolysis was discontinued, and 532.4 g. of a water-white crude cell product was drained from the bottom of the cell.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent tion of Michigan No Drawing. Filed Nov. 22, 1965, Ser. No. 509,210
2 Claims U.S. Cl. 204-59 Int. Cl. Bollr 3/00 This application relates to a new process for the production of perfluoroalkylsulfonyl fluorides, which are valuable intermediates for the preparation of agents for rendering fabrics oleophobic, and which are useful as surfactants in their own right.
U.S. Patent 2,519,983, issued to Simons, discloses the electrochemical fluorination of organic materials with anhydrous hydrofluoric acid. US. Patent 2,732,398, issued to Brice and Trott, discloses the use of the process of Simons to convert hydrocarbon sulfonyl halides into perfluoroalkylsulfonyl fluorides.
This invention relates to the process of electrolyzing a current-conducting mixture of a composition consisting essentially of a liquid solution of 0113 CH3 CH3 CnHrsC CH2CH-CHCH2? Oz.
and
(C2H5)2C HM S 2.
They are known compositions which are made by the reaction of the appropriate alpha-omega-diolefin (e.g. butadiene) with S0 The major advantage of the process of this invention is its relatively high yield of product, which renders it commercially desirable. The process is also unique in that the electrochemical fluorination process has never before been found to cause ring cleavage at a carbonsulfur linkage to form a perfluoroalkylsulfonyl fluoride.
The preferred reactant is tetramethylene sulfone because of its ready availability.
Details concerning the types of electrolytic cells and operating procedures which are useable in this invention are available in the Simons patent and the Brice, et al. patent, both of which are cited above.
The process of this invention is generally performed at a low temperature, usually under C., in order to 3,423,299 Patented Jan. 21, 1969 easily maintain the hydrogen fluoride in the liquid form without the use of pressure. The alkylene sulfone ingredients are generally quite soluble in liquid hydrogen fluoride.
The conductivity of the alkylene sulfone-hydrogen fluoride solution is usually adequate to permit electrolysis at a sufliciently low voltage to prevent the evolution of elemental fluorine, which begins to form when about 10 to 12 volts are applied to a cell anode. However, small amounts of conductivity additives such as sodium or potassium fluoride can be added, if desired. When a nickel anode is used, voltages of from 4 to 8 volts generally give the best results.
It is preferred for an excess of hydrogen fluoride to be present so that there is more than enough fluorine available for reaction with the sulfone, but the proportion of the two reactants to each other is not critical to the operability of this invention. The yield of perfluoroalkylsulfonyl fluoride will, however, be greatly increased when a substantial excess of hydrogen fluoride is used,
The term essentially anhydrous is intended to imply that trace of water can be present in the hydrogen fluoride, but that the water content should not be more than about 2 percent in order to avoid undesirable side reactions and the increased corrosiveness of aqueous HF.
It is preferred to operate the cell on one polarity with direct current although alternating current is operative.
Several hours or days of operation are generally required in order to maximize the yield of the process of this application.
The electrochemical cell itself is best made of any nonreactive metal, e.g. nickel, Monel, gold plate, or molybdenum. The cell can also be made of graphite or fluorocarbon plastics, if desired.
The cathodes and anodes can be made of any conductive material which is not corroded by anhydrous HF, e.g., nickel, Monel, carbon, silicon carbide, etc.
The following examples are illustrative only and should not be construed as limiting the invention which is properly delineated in the appended claims.
EXAMPLE 1 An electrochemical cell was prepared and fitted with a nickel anode and cathode and with a condenser designed to trap and return all volatiles condensing at l5 C. or above and evolving from the cell. The top of the condenser was vented out of doors.
The cell was cooled to l0 C., and anhydrous HF vapor was added until about 3500 ml. of liquid HF were present in the cell. To this was added 1242.5 g. of tetramethylene sulfone, and the cell was operated for 5 days at about 0 C. with a direct current of about amperes and 5.5 volts.
Following this, 1443 grams of crude cell product were drained from the cell. Analysis by gas-liquid chromatography indicated that about 94 percent by weight of the crude product was CF CF CF CF SO F, which amounts to over a 40 percent yield, based on the tetramethylene sulfone reactant.
EXAMPLE 2 When an electrochemical cell, fitted with a graphite anode and cathode and the same condenser as in Example l is filled with 1 kg. of octamethylene sulfone and 2 kg. of liquid HF, electrolysis for several days at 10 C. at a voltage of 7 volts produces a liberal yield of nperfluorooctylsulfonyl fluoride.
EXAMPLE 3 When the experiment of Example 1 is repeated with the substitution of hexamethylene sulfone for the tetra- 3 methylene sulfone ingredient, a high yield of n-perfluorohexylsulfonyl fluoride is recovered.
EXAMPLE 4 CHzCHz in 200 or 300 ml. of liquid, anhydrous hydrogen fluoride.
Electrolysis was initiated at 10 C., and an average current of 85 amperes and 5.5 volts was maintained for 48 hours with an average temperature of C. At the end of the period, the current began to decrease. When it had fallen to 15 amperes, the electrolysis was discontinued, and 532.4 g. of a water-white crude cell product was drained from the bottom of the cell.
Analysis showed the cell product to contain 28.6 mole percent of OFJCFgSiFCFISOZF CF; and 28.0 mole percent of CFzOFCFzCFzSOzF EXAMPLE When the experiment of Example 4 is repeated with the substitution of for the sulfone ingredient used above, a liberal yield of C4F9CF2CF2CF2CF2SO2F and CqFs is formed.
That which is claimed is: 1. The process of electrolyzing a current-conducting mixture of a composition consisting essentially of a liquid solution of References Cited UNITED STATES PATENTS 8/1950 Simons 1/1956 Brice et a1.
HOWARD S. WILLIAMS, Primary Examiner.
Claims (1)
1. THE PROCESS OF ELECTROLYZING A CURRENT-CONDUCTING MIXTURE OF A COMPOSITION CONSISTING ESSENTIALLY OF A LIQUID SOLUTION OF
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50921065A | 1965-11-22 | 1965-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3423299A true US3423299A (en) | 1969-01-21 |
Family
ID=24025734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US509210A Expired - Lifetime US3423299A (en) | 1965-11-22 | 1965-11-22 | Electrochemical fluorination of polymethylene sulfones to produce perfluoroalkylsulfonyl fluorides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3423299A (en) |
| AT (1) | AT264483B (en) |
| DE (1) | DE1264440B (en) |
| FR (1) | FR1501396A (en) |
| GB (1) | GB1099240A (en) |
| NL (2) | NL6616346A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3623963A (en) * | 1969-03-13 | 1971-11-30 | Bayer Ag | Process for the manufacture of perfluoralkylsulphonyl fluorides |
| US3951762A (en) * | 1972-01-14 | 1976-04-20 | Bayer Aktiengesellschaft | Preparation of perfluorinated organic sulfonyl fluorides |
| US4425199A (en) | 1981-04-02 | 1984-01-10 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for the preparation of (ω-fluorosulfonyl)-haloaliphatic carboxylic acid fluorides |
| US5286352A (en) * | 1990-02-28 | 1994-02-15 | Minnesota Mining And Manufacturing Company | Electrochemical production of higher pentafluorosulfonyl acid fluorides |
| US5541235A (en) * | 1995-03-06 | 1996-07-30 | Minnesota Mining And Manufacturing Company | Organic soluble cationic dyes with fluorinated alkylsulfonyl counterions |
| US5554664A (en) * | 1995-03-06 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Energy-activatable salts with fluorocarbon anions |
| US5874616A (en) * | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3043427A1 (en) | 1980-11-18 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | PERFLUORED SULPHONIC ACID FLUORIDES AND METHOD FOR THE PRODUCTION THEREOF |
| US5011983A (en) * | 1987-01-23 | 1991-04-30 | Minnesota Mining And Manufacturing Company | Preparation and reactions of omega-halosulfonyl perfluoroalkanesulfonates |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519983A (en) * | 1948-11-29 | 1950-08-22 | Minnesota Mining & Mfg | Electrochemical process of making fluorine-containing carbon compounds |
| US2732398A (en) * | 1953-01-29 | 1956-01-24 | cafiicfzsojk |
-
0
- NL NL127400D patent/NL127400C/xx active
-
1965
- 1965-11-22 US US509210A patent/US3423299A/en not_active Expired - Lifetime
-
1966
- 1966-07-27 DE DED50696A patent/DE1264440B/en active Pending
- 1966-09-08 AT AT848466A patent/AT264483B/en active
- 1966-11-17 GB GB51592/66A patent/GB1099240A/en not_active Expired
- 1966-11-21 FR FR84372A patent/FR1501396A/en not_active Expired
- 1966-11-21 NL NL6616346A patent/NL6616346A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519983A (en) * | 1948-11-29 | 1950-08-22 | Minnesota Mining & Mfg | Electrochemical process of making fluorine-containing carbon compounds |
| US2732398A (en) * | 1953-01-29 | 1956-01-24 | cafiicfzsojk |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3623963A (en) * | 1969-03-13 | 1971-11-30 | Bayer Ag | Process for the manufacture of perfluoralkylsulphonyl fluorides |
| US3951762A (en) * | 1972-01-14 | 1976-04-20 | Bayer Aktiengesellschaft | Preparation of perfluorinated organic sulfonyl fluorides |
| US4425199A (en) | 1981-04-02 | 1984-01-10 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for the preparation of (ω-fluorosulfonyl)-haloaliphatic carboxylic acid fluorides |
| US5286352A (en) * | 1990-02-28 | 1994-02-15 | Minnesota Mining And Manufacturing Company | Electrochemical production of higher pentafluorosulfonyl acid fluorides |
| US5541235A (en) * | 1995-03-06 | 1996-07-30 | Minnesota Mining And Manufacturing Company | Organic soluble cationic dyes with fluorinated alkylsulfonyl counterions |
| US5554664A (en) * | 1995-03-06 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Energy-activatable salts with fluorocarbon anions |
| US5874616A (en) * | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL127400C (en) | |
| DE1264440B (en) | 1968-03-28 |
| GB1099240A (en) | 1968-01-17 |
| NL6616346A (en) | 1967-05-23 |
| AT264483B (en) | 1968-09-10 |
| FR1501396A (en) | 1967-11-10 |
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