JPH0420998B2 - - Google Patents
Info
- Publication number
- JPH0420998B2 JPH0420998B2 JP60103042A JP10304285A JPH0420998B2 JP H0420998 B2 JPH0420998 B2 JP H0420998B2 JP 60103042 A JP60103042 A JP 60103042A JP 10304285 A JP10304285 A JP 10304285A JP H0420998 B2 JPH0420998 B2 JP H0420998B2
- Authority
- JP
- Japan
- Prior art keywords
- fluoride
- perfluoro
- formula
- electrolysis
- electrolytic
- 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
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- 238000005868 electrolysis reaction Methods 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 16
- 238000003682 fluorination reaction Methods 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 8
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- -1 perfluoro(N-methyl-5-dimethylaminooxazoline) Chemical compound 0.000 description 4
- WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- JUYUGKVNORJSLJ-UHFFFAOYSA-N 2-(dimethylamino)acetyl fluoride Chemical compound CN(C)CC(F)=O JUYUGKVNORJSLJ-UHFFFAOYSA-N 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
- 235000013024 sodium fluoride Nutrition 0.000 description 3
- 239000011775 sodium fluoride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- LIJRSRSBXLWJIJ-UHFFFAOYSA-N 2-morpholin-4-ylpropanoyl fluoride Chemical compound FC(=O)C(C)N1CCOCC1 LIJRSRSBXLWJIJ-UHFFFAOYSA-N 0.000 description 2
- QPYNRDDEZUESHL-UHFFFAOYSA-N 2-piperidin-1-ylpropanoyl fluoride Chemical compound FC(=O)C(C)N1CCCCC1 QPYNRDDEZUESHL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- GTPQFCOJHZQXRX-UHFFFAOYSA-N FC(=O)C(C)N1CCCC1 Chemical compound FC(=O)C(C)N1CCCC1 GTPQFCOJHZQXRX-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CGYSGEFXYQMNJM-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n,n-bis(trifluoromethyl)ethanamine Chemical compound FC(F)(F)N(C(F)(F)F)C(F)(F)C(F)(F)F CGYSGEFXYQMNJM-UHFFFAOYSA-N 0.000 description 1
- UMGCTGRNIYHTCR-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluoro-1-(1,1,2,2,2-pentafluoroethyl)pyrrolidine Chemical compound FC(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C1(F)F UMGCTGRNIYHTCR-UHFFFAOYSA-N 0.000 description 1
- BMPMIPFMFUBMNZ-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,2,2,2-pentafluoroethyl)morpholine Chemical compound FC(F)(F)C(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F BMPMIPFMFUBMNZ-UHFFFAOYSA-N 0.000 description 1
- DWGMAIPVJRBOIB-UHFFFAOYSA-N 2-(dimethylamino)-n,n-dimethylacetamide Chemical compound CN(C)CC(=O)N(C)C DWGMAIPVJRBOIB-UHFFFAOYSA-N 0.000 description 1
- VXEGBOQHXMWDSA-UHFFFAOYSA-N 2-(dimethylamino)-n,n-dimethylpropanamide Chemical compound CN(C)C(C)C(=O)N(C)C VXEGBOQHXMWDSA-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DTRWLFVXPPXISV-UHFFFAOYSA-N 2-[bis(trifluoromethyl)amino]-2,3,3,3-tetrafluoropropanoic acid Chemical compound OC(=O)C(F)(C(F)(F)F)N(C(F)(F)F)C(F)(F)F DTRWLFVXPPXISV-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical class CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- BZIUTFGOTTWBOQ-UHFFFAOYSA-N FC(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C1(F)C(F)(F)F Chemical compound FC(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C1(F)C(F)(F)F BZIUTFGOTTWBOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- YQALCVILRBWLNX-UHFFFAOYSA-N methyl 2-(dimethylamino)propanoate Chemical compound COC(=O)C(C)N(C)C YQALCVILRBWLNX-UHFFFAOYSA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- BCYHICYAWLIZRU-UHFFFAOYSA-N methyl 2-pyrrolidin-1-ylpropanoate Chemical compound COC(=O)C(C)N1CCCC1 BCYHICYAWLIZRU-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- JWDVRIOQNXFNES-UHFFFAOYSA-N n,1,1,1-tetrafluoro-n-(trifluoromethyl)methanamine Chemical compound FC(F)(F)N(F)C(F)(F)F JWDVRIOQNXFNES-UHFFFAOYSA-N 0.000 description 1
- LUVWBWCGYGIGFO-UHFFFAOYSA-N n,n-bis(trifluoromethyl)carbamoyl fluoride Chemical compound FC(=O)N(C(F)(F)F)C(F)(F)F LUVWBWCGYGIGFO-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- USAAEUHMVCSUQS-UHFFFAOYSA-N perfluoro-N-ethylpiperidine Chemical compound FC(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F USAAEUHMVCSUQS-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 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
- 239000000243 solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60103042A JPS61260047A (ja) | 1985-05-15 | 1985-05-15 | 新規なペルフルオロカルボン酸フルオリド及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60103042A JPS61260047A (ja) | 1985-05-15 | 1985-05-15 | 新規なペルフルオロカルボン酸フルオリド及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61260047A JPS61260047A (ja) | 1986-11-18 |
| JPH0420998B2 true JPH0420998B2 (es) | 1992-04-07 |
Family
ID=14343608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60103042A Granted JPS61260047A (ja) | 1985-05-15 | 1985-05-15 | 新規なペルフルオロカルボン酸フルオリド及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61260047A (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011048053A1 (en) * | 2009-10-21 | 2011-04-28 | Solvay Fluor Gmbh | Method for the manufacture of fluorinated ethylene carbonates |
-
1985
- 1985-05-15 JP JP60103042A patent/JPS61260047A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61260047A (ja) | 1986-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |