JPH0251896B2 - - Google Patents
Info
- Publication number
- JPH0251896B2 JPH0251896B2 JP62227468A JP22746887A JPH0251896B2 JP H0251896 B2 JPH0251896 B2 JP H0251896B2 JP 62227468 A JP62227468 A JP 62227468A JP 22746887 A JP22746887 A JP 22746887A JP H0251896 B2 JPH0251896 B2 JP H0251896B2
- Authority
- JP
- Japan
- Prior art keywords
- butyric acid
- perfluoro
- formula
- dialkylamino
- fluoride
- 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000005868 electrolysis reaction Methods 0.000 description 23
- 238000010521 absorption reaction Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000003682 fluorination reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 8
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000004652 butanoic acids Chemical class 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- -1 perfluoroalkyl iodide Chemical compound 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LXKBRCNVHBNPSJ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoro-1-(2,2,3,4,4,5,5-heptafluorooxolan-3-yl)pyrrolidine Chemical compound FC1(F)C(F)(F)OC(F)(F)C1(F)N1C(F)(F)C(F)(F)C(F)(F)C1(F)F LXKBRCNVHBNPSJ-UHFFFAOYSA-N 0.000 description 1
- UNZKRGKSTGCHQU-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(2,2,3,4,4,5,5-heptafluorooxolan-3-yl)morpholine Chemical compound FC1(F)C(F)(F)OC(F)(F)C1(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F UNZKRGKSTGCHQU-UHFFFAOYSA-N 0.000 description 1
- OHZHVSKXVITCEP-UHFFFAOYSA-N 2,2,3,4,4,5,5-heptafluoro-N,N-bis(trifluoromethyl)oxolan-3-amine Chemical compound FC(F)(F)N(C(F)(F)F)C1(F)C(F)(F)OC(F)(F)C1(F)F OHZHVSKXVITCEP-UHFFFAOYSA-N 0.000 description 1
- JUYUGKVNORJSLJ-UHFFFAOYSA-N 2-(dimethylamino)acetyl fluoride Chemical compound CN(C)CC(F)=O JUYUGKVNORJSLJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- GSJWYIDMIRQHMV-UHFFFAOYSA-N butanoyl fluoride Chemical compound CCCC(F)=O GSJWYIDMIRQHMV-UHFFFAOYSA-N 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
- SDHJSSYHXWOAEL-UHFFFAOYSA-N methyl 3-(azepan-1-yl)butanoate Chemical compound COC(=O)CC(C)N1CCCCCC1 SDHJSSYHXWOAEL-UHFFFAOYSA-N 0.000 description 1
- WUQJBIQCZYGKAJ-UHFFFAOYSA-N methyl 3-(diethylamino)butanoate Chemical compound CCN(CC)C(C)CC(=O)OC WUQJBIQCZYGKAJ-UHFFFAOYSA-N 0.000 description 1
- KQYAKXSGEDRRKF-UHFFFAOYSA-N methyl 3-(dimethylamino)butanoate Chemical compound COC(=O)CC(C)N(C)C KQYAKXSGEDRRKF-UHFFFAOYSA-N 0.000 description 1
- ADWBNEMUIBKAJC-UHFFFAOYSA-N methyl 3-morpholin-4-ylbutanoate Chemical compound COC(=O)CC(C)N1CCOCC1 ADWBNEMUIBKAJC-UHFFFAOYSA-N 0.000 description 1
- RFKOTZLJKQYWFL-UHFFFAOYSA-N methyl 3-piperidin-1-ylbutanoate Chemical compound COC(=O)CC(C)N1CCCCC1 RFKOTZLJKQYWFL-UHFFFAOYSA-N 0.000 description 1
- CLIFHFGCXTXFLR-UHFFFAOYSA-N methyl 3-pyrrolidin-1-ylbutanoate Chemical compound COC(=O)CC(C)N1CCCC1 CLIFHFGCXTXFLR-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62227468A JPS6470450A (en) | 1987-09-10 | 1987-09-10 | Novel nitrogen-containing perfluorocarboxylic fluoride and its preparation |
| US07/242,308 US4985556A (en) | 1987-09-10 | 1988-09-09 | Perfluoro(dialkylaminopropene) derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62227468A JPS6470450A (en) | 1987-09-10 | 1987-09-10 | Novel nitrogen-containing perfluorocarboxylic fluoride and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6470450A JPS6470450A (en) | 1989-03-15 |
| JPH0251896B2 true JPH0251896B2 (zh) | 1990-11-08 |
Family
ID=16861350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62227468A Granted JPS6470450A (en) | 1987-09-10 | 1987-09-10 | Novel nitrogen-containing perfluorocarboxylic fluoride and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6470450A (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266724A (en) * | 1990-09-04 | 1993-11-30 | Matsushita Electric Industrial Co., Ltd. | Fluorine-containing compounds |
| US5188747A (en) * | 1990-09-04 | 1993-02-23 | Matsushita Electric Industrial Co., Ltd. | Fluorine-containing lubricant compounds |
| JP2002145846A (ja) * | 2000-11-09 | 2002-05-22 | Mitsui Chemicals Inc | アミノ酸フロリド誘導体の製造法 |
| FR3067347B1 (fr) | 2017-06-09 | 2020-07-24 | Arkema France | 1,1,1,2,3,3-hexafluoropropane de haute purete, son procede de fabrication et utilisation |
-
1987
- 1987-09-10 JP JP62227468A patent/JPS6470450A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6470450A (en) | 1989-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |