CA1153388A - Procede de preparation de fluorures de fluorobenzene sulfonyle - Google Patents
Procede de preparation de fluorures de fluorobenzene sulfonyleInfo
- Publication number
- CA1153388A CA1153388A CA000367253A CA367253A CA1153388A CA 1153388 A CA1153388 A CA 1153388A CA 000367253 A CA000367253 A CA 000367253A CA 367253 A CA367253 A CA 367253A CA 1153388 A CA1153388 A CA 1153388A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- equal
- fluoride
- radical
- iii
- 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
- 150000002222 fluorine compounds Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 20
- -1 alkyl radical Chemical class 0.000 claims description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000003352 sequestering agent Substances 0.000 claims description 14
- 239000007983 Tris buffer Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003880 polar aprotic solvent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 241000238876 Acari Species 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 abstract description 3
- UOECQWWSUHZUMI-UHFFFAOYSA-N 2-chlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC=CC=C1Cl UOECQWWSUHZUMI-UHFFFAOYSA-N 0.000 abstract description 2
- ODVXTZVBPYPQLJ-UHFFFAOYSA-N 2-fluorobenzenesulfonyl fluoride Chemical class FC1=CC=CC=C1S(F)(=O)=O ODVXTZVBPYPQLJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 abstract description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 8
- 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 6
- HHHPKVLNNLPPKL-UHFFFAOYSA-N benzene;hydrofluoride Chemical compound F.C1=CC=CC=C1 HHHPKVLNNLPPKL-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000011698 potassium fluoride Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000001174 ascending effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- AZLGIYPCGAIVBH-UHFFFAOYSA-N chlorobenzene;sulfuryl difluoride Chemical compound FS(F)(=O)=O.ClC1=CC=CC=C1 AZLGIYPCGAIVBH-UHFFFAOYSA-N 0.000 description 3
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZIBJZUAQAYUYHE-UHFFFAOYSA-N 2,4,5-trichlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl ZIBJZUAQAYUYHE-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229910006095 SO2F Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- MODOOKQNBYWELS-UHFFFAOYSA-N chlorobenzene hydrofluoride Chemical compound ClC1=CC=CC=C1.F MODOOKQNBYWELS-UHFFFAOYSA-N 0.000 description 2
- WZQYDCGVFQMPON-UHFFFAOYSA-N fluorobenzene hydrofluoride Chemical class C1=CC=C(C=C1)F.F WZQYDCGVFQMPON-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- LYDBMJRBEFPWSM-UHFFFAOYSA-N 1-chloro-2-fluorobenzene;sulfuryl difluoride Chemical compound FS(F)(=O)=O.FC1=CC=CC=C1Cl LYDBMJRBEFPWSM-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- XDSCWWMZWJQBTA-UHFFFAOYSA-N 2,3,4,5-tetrachlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl XDSCWWMZWJQBTA-UHFFFAOYSA-N 0.000 description 1
- FNXHXUGJBKXHFS-UHFFFAOYSA-N 2,3-dichlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC=CC(Cl)=C1Cl FNXHXUGJBKXHFS-UHFFFAOYSA-N 0.000 description 1
- PUYJBWSFLASCBC-UHFFFAOYSA-N 2,4,6-trifluorobenzenesulfonyl fluoride Chemical compound FC1=CC(F)=C(S(F)(=O)=O)C(F)=C1 PUYJBWSFLASCBC-UHFFFAOYSA-N 0.000 description 1
- FDTPBIKNYWQLAE-UHFFFAOYSA-N 2,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 FDTPBIKNYWQLAE-UHFFFAOYSA-N 0.000 description 1
- RFKAVWPYSXFORB-UHFFFAOYSA-N 2,5-dichlorobenzenesulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC(Cl)=CC=C1Cl RFKAVWPYSXFORB-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- AMJKUTUQZZVWMJ-UHFFFAOYSA-N 4-fluorobenzenesulfonyl fluoride Chemical compound FC1=CC=C(S(F)(=O)=O)C=C1 AMJKUTUQZZVWMJ-UHFFFAOYSA-N 0.000 description 1
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IKXDJVMFNZPUHQ-UHFFFAOYSA-N Cl.ClC=1C(=C(C=CC1)Cl)Cl Chemical compound Cl.ClC=1C(=C(C=CC1)Cl)Cl IKXDJVMFNZPUHQ-UHFFFAOYSA-N 0.000 description 1
- LCYYNOYBLITOED-UHFFFAOYSA-N ClC(C=C(C(Cl)=C1Cl)Cl)=C1Cl.F Chemical compound ClC(C=C(C(Cl)=C1Cl)Cl)=C1Cl.F LCYYNOYBLITOED-UHFFFAOYSA-N 0.000 description 1
- PWTZGWCQOYHSAL-UHFFFAOYSA-N ClC1=CC(Cl)=CC=C1.F Chemical compound ClC1=CC(Cl)=CC=C1.F PWTZGWCQOYHSAL-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 description 1
- UCUJUFDOQOJLBE-UHFFFAOYSA-N [Cl].[Ca] Chemical compound [Cl].[Ca] UCUJUFDOQOJLBE-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- TXWKSFNVNFDKQQ-UHFFFAOYSA-N fluorobenzene;sulfuryl difluoride Chemical class FS(F)(=O)=O.FC1=CC=CC=C1 TXWKSFNVNFDKQQ-UHFFFAOYSA-N 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR79.31220 | 1979-12-20 | ||
| FR7931220A FR2471974A1 (fr) | 1979-12-20 | 1979-12-20 | Procede de preparation de fluorures de fluorobenzene sulfonyle |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1153388A true CA1153388A (fr) | 1983-09-06 |
Family
ID=9232996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000367253A Expired CA1153388A (fr) | 1979-12-20 | 1980-12-19 | Procede de preparation de fluorures de fluorobenzene sulfonyle |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4369145A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0032077B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56127350A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE3856T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1153388A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3063919D1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2471974A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0063872B1 (en) * | 1981-04-27 | 1985-07-17 | Imperial Chemical Industries Plc | Process for the preparation of fluoromethyl pyridines and certain novel products obtained therefrom |
| US4886629A (en) * | 1988-06-06 | 1989-12-12 | Allied-Signal Inc. | Process for the preparation of fluorinated benzene sulfonyl fluorides |
| US4937397A (en) * | 1988-11-28 | 1990-06-26 | The Dow Chemical Company | Preparation of halofluorobenzenes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1360917A (fr) * | 1962-05-11 | 1964-05-15 | Nat Smelting Co Ltd | Procédé de fluoruration de composés perhalogénés et produits obtenus |
| NL302228A (cg-RX-API-DMAC7.html) * | 1962-12-20 | |||
| GB1004375A (en) * | 1963-10-03 | 1965-09-15 | Ici Ltd | Process for making fluorochlorobenzenes and hexafluorobenzene |
| GB1052462A (cg-RX-API-DMAC7.html) * | 1964-09-16 | |||
| FR1446914A (fr) * | 1964-09-16 | 1966-07-22 | Imp Smelting Corp Ltd | Procédé de préparation de nouveaux fluorures d'aryl-sulfonyle |
-
1979
- 1979-12-20 FR FR7931220A patent/FR2471974A1/fr active Granted
-
1980
- 1980-12-08 AT AT80401752T patent/ATE3856T1/de not_active IP Right Cessation
- 1980-12-08 DE DE8080401752T patent/DE3063919D1/de not_active Expired
- 1980-12-08 EP EP80401752A patent/EP0032077B1/fr not_active Expired
- 1980-12-16 US US06/216,914 patent/US4369145A/en not_active Expired - Fee Related
- 1980-12-18 JP JP17812780A patent/JPS56127350A/ja active Granted
- 1980-12-19 CA CA000367253A patent/CA1153388A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0032077B1 (fr) | 1983-06-22 |
| FR2471974B1 (cg-RX-API-DMAC7.html) | 1984-02-24 |
| US4369145A (en) | 1983-01-18 |
| EP0032077A1 (fr) | 1981-07-15 |
| JPS5741465B2 (cg-RX-API-DMAC7.html) | 1982-09-03 |
| ATE3856T1 (de) | 1983-07-15 |
| JPS56127350A (en) | 1981-10-06 |
| DE3063919D1 (en) | 1983-07-28 |
| FR2471974A1 (fr) | 1981-06-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1125309A (fr) | Procede de preparation de derives benzeniques par reaction d'un halogenobenzene active avec un reactif organique anionique oxygene ou soufre | |
| FR3088931B1 (fr) | Procédé de préparation du sel de lithium de bis(fluorosulfonyl)imide | |
| US4873027A (en) | Fluoroalkylaryliodonuim compounds | |
| CA1124741A (fr) | Procede de preparation d'ethers diaryliques | |
| CA1153388A (fr) | Procede de preparation de fluorures de fluorobenzene sulfonyle | |
| CS209933B2 (en) | Method of making the 4-fluor-3-phenoxytoluen | |
| Beck et al. | Nitro displacement by methanethiol anion. Synthesis of bis-, tris-, pentakis-, and hexakis (methylthio) benzenes | |
| JPH0229657B2 (cg-RX-API-DMAC7.html) | ||
| EP0049186B1 (fr) | Procédé de préparation de fluorobenzonitriles | |
| FR2459216A1 (fr) | Procede de preparation d'ethers aryliques | |
| JPWO2018159515A1 (ja) | ペンタフルオロスルファニル芳香族化合物の製造方法 | |
| US4264769A (en) | Process for the preparation of hydroxyphenyl ethers | |
| US4194054A (en) | Preparation of substituted fluorobenzenes | |
| EP0334720B1 (fr) | Nouveau procédé de préparation d'isocyanates d'acyle | |
| CA1182841A (fr) | Procede de sulfonylation d'halogenobenzenes | |
| JPH0912508A (ja) | ２−フルオロ−イソ酪酸アルキルの製造方法 | |
| JPS59122456A (ja) | ジシクロヘキシルジスルフイドの製造法 | |
| JPS6128670B2 (cg-RX-API-DMAC7.html) | ||
| EP0140783B1 (fr) | Procédé de préparation d'anilines méta substituées | |
| FR2505327A1 (fr) | Procede d'halogenation en meta de n-(o,o'-dialkyl phenyl) alaninates et homologues | |
| US3781369A (en) | Substituted haloalkoxy phenols | |
| EP0113625B1 (fr) | Procédé de préparation de composés benzéniques trifluorométhylés | |
| US3502726A (en) | Hydrazine derivatives of oligomers of tetrafluoroethylene and hexafluoropropene | |
| US3784610A (en) | Substituted phenoxy-and phenylthio-alkanols and alkanethiols | |
| JPS6172745A (ja) | スルホニルカルバミン酸エステル及びその製法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |