GB776507A - Improved process of making fluorocarbon carbonyl fluorides - Google Patents
Improved process of making fluorocarbon carbonyl fluoridesInfo
- Publication number
- GB776507A GB776507A GB23597/55A GB2359755A GB776507A GB 776507 A GB776507 A GB 776507A GB 23597/55 A GB23597/55 A GB 23597/55A GB 2359755 A GB2359755 A GB 2359755A GB 776507 A GB776507 A GB 776507A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoride
- sulphonyl
- fluorocarbon
- saturated
- mols
- 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
- -1 fluorocarbon carbonyl fluorides Chemical class 0.000 title abstract 7
- 239000002253 acid Substances 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- UZBIRLJMURQVMX-UHFFFAOYSA-J tetrasodium;pyrene-1,3,6,8-tetrasulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C2C(S(=O)(=O)[O-])=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 UZBIRLJMURQVMX-UHFFFAOYSA-J 0.000 abstract 2
- RUFSXELMOQBMOF-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RUFSXELMOQBMOF-UHFFFAOYSA-N 0.000 abstract 1
- XLIFBQWTSCGUEB-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XLIFBQWTSCGUEB-UHFFFAOYSA-N 0.000 abstract 1
- OVRRDOOFRPDYKQ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluorodecanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OVRRDOOFRPDYKQ-UHFFFAOYSA-N 0.000 abstract 1
- UOWXEPNLVLRCKI-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)=O UOWXEPNLVLRCKI-UHFFFAOYSA-N 0.000 abstract 1
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- 229910000990 Ni alloy Inorganic materials 0.000 abstract 1
- 229910000831 Steel Inorganic materials 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000005868 electrolysis reaction Methods 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000010959 steel Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical class FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
- C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
Saturated fluoro-carbon carbonyl fluorides are prepared by thermally reacting a saturated perfluorocarbon-difluoromethyl-sulphonyl fluoride with nitrogen dioxide or nitric oxide at 450-650 DEG C. in the vapour phase. Suitably a perfluoroalkanemonosulphonyl fluoride having more than one carbon atom such as perfluoro-octanoyl fluoride, is reacted with 3 to 7 mols., more preferably 3.5 to 4 mols. of NO2 at 550 DEG C. The reaction follows the equation: <FORM:0776507/IV(b)/1> where m is 1 in the case of monofunctional compounds, but is 2 or more in the case of di- or polyfunctional compounds, and Rf is a saturated fluorocarbon radical which may be either acyclic, cyclic or a combination of cyclic and acyclic radicals. The reaction is conveniently carried out by passing the reactants through a tube of nickel, nickel alloy, steel or platinum maintained at the desired reaction temperature. The product may be recovered by fractional distillation or may be hydrolysed with a base to form the corresponding fluorocarbon carboxylate salt, or with water to form the fluorocarbon carboxylic acid. Examples describe the preparation according to the invention of: (1) perfluoropentanoyl fluoride, recovered as the potassium salt of the corresponding acid: (2), (4) and (5) perfluoro-octanoyl fluoride, together with minor amounts of perfluoroheptanoyl fluoride by-product, both isolated as the free acids; and (3) perfluorodecanoyl fluoride and the corresponding acid. Reference is also made to the preparation of perfluorosebacyl difluoride. Starting materials. The perfluorinated fluorocarbondifluoromethyl sulphonyl fluorides used as starting materials are made by electrolysis of a mixture of a hydrocarbon sulphonyl fluoride or sulphonyl chloride and hydrogen fluoride. Several monofunctional compounds are listed. Specifications 659,251, 718,318 and 758,467 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US776507XA | 1954-08-17 | 1954-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB776507A true GB776507A (en) | 1957-06-05 |
Family
ID=22139285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23597/55A Expired GB776507A (en) | 1954-08-17 | 1955-08-16 | Improved process of making fluorocarbon carbonyl fluorides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB776507A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5616794A (en) * | 1995-11-17 | 1997-04-01 | Minnesota Mining And Manufacturing Company | Process for preparing fluorocarboxylic acid halides |
-
1955
- 1955-08-16 GB GB23597/55A patent/GB776507A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5616794A (en) * | 1995-11-17 | 1997-04-01 | Minnesota Mining And Manufacturing Company | Process for preparing fluorocarboxylic acid halides |
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