JPS62158236A - 塩化トリフルオルアセチルの製造方法 - Google Patents
塩化トリフルオルアセチルの製造方法Info
- Publication number
- JPS62158236A JPS62158236A JP61305598A JP30559886A JPS62158236A JP S62158236 A JPS62158236 A JP S62158236A JP 61305598 A JP61305598 A JP 61305598A JP 30559886 A JP30559886 A JP 30559886A JP S62158236 A JPS62158236 A JP S62158236A
- Authority
- JP
- Japan
- Prior art keywords
- chlorination
- carried out
- ester
- mol
- chlorine
- 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.)
- Granted
Links
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 14
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 9
- 239000002841 Lewis acid Substances 0.000 claims abstract description 7
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- PBNSIWIXDXFYGL-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2,2,2-trichloroacetate Chemical compound FC(F)(F)COC(=O)C(Cl)(Cl)Cl PBNSIWIXDXFYGL-UHFFFAOYSA-N 0.000 claims description 4
- ZKUJOCJJXCPCFS-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)COC(=O)C(F)(F)F ZKUJOCJJXCPCFS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 11
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 description 2
- UJZBSAONPRVEIJ-UHFFFAOYSA-N 2,2,2-trifluoroethyl carbonochloridate Chemical compound FC(F)(F)COC(Cl)=O UJZBSAONPRVEIJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- -1 tertiary amine hydrochlorides Chemical class 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- VMOSJLZOIYFLIE-UHFFFAOYSA-N (1,1-dichloro-2,2,2-trifluoroethyl) 2,2,2-trichloroacetate Chemical compound FC(F)(F)C(Cl)(Cl)OC(=O)C(Cl)(Cl)Cl VMOSJLZOIYFLIE-UHFFFAOYSA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-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
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8519567A FR2592376B1 (fr) | 1985-12-31 | 1985-12-31 | Procede de preparation de chlorure de trifluoroacetyle |
| FR85/19567 | 1985-12-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62158236A true JPS62158236A (ja) | 1987-07-14 |
| JPH0214340B2 JPH0214340B2 (en:Method) | 1990-04-06 |
Family
ID=9326425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61305598A Granted JPS62158236A (ja) | 1985-12-31 | 1986-12-23 | 塩化トリフルオルアセチルの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0232666B1 (en:Method) |
| JP (1) | JPS62158236A (en:Method) |
| AT (1) | ATE47834T1 (en:Method) |
| CA (1) | CA1263870A (en:Method) |
| DE (1) | DE3666806D1 (en:Method) |
| ES (1) | ES2011622B3 (en:Method) |
| FR (1) | FR2592376B1 (en:Method) |
| GR (1) | GR3000211T3 (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5595373A (en) * | 1994-12-21 | 1997-01-21 | Tokai Rubber Industries, Ltd. | Fluid-filled damping device having two axially spaced annular fluid chambers communicating with each other through orifice |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1285999B (de) * | 1964-05-15 | 1969-01-02 | Basf Ag | Verfahren zur Herstellung von gesaettigten Fluorfettsaeurechloriden |
-
1985
- 1985-12-31 FR FR8519567A patent/FR2592376B1/fr not_active Expired
-
1986
- 1986-12-02 CA CA000524329A patent/CA1263870A/fr not_active Expired
- 1986-12-23 JP JP61305598A patent/JPS62158236A/ja active Granted
- 1986-12-24 EP EP86420309A patent/EP0232666B1/fr not_active Expired
- 1986-12-24 ES ES86420309T patent/ES2011622B3/es not_active Expired - Lifetime
- 1986-12-24 DE DE8686420309T patent/DE3666806D1/de not_active Expired
- 1986-12-24 AT AT86420309T patent/ATE47834T1/de not_active IP Right Cessation
-
1989
- 1989-11-10 GR GR89400236T patent/GR3000211T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5595373A (en) * | 1994-12-21 | 1997-01-21 | Tokai Rubber Industries, Ltd. | Fluid-filled damping device having two axially spaced annular fluid chambers communicating with each other through orifice |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2592376B1 (fr) | 1988-02-19 |
| ES2011622B3 (es) | 1990-02-01 |
| JPH0214340B2 (en:Method) | 1990-04-06 |
| CA1263870A (fr) | 1989-12-12 |
| GR3000211T3 (en) | 1990-12-31 |
| ATE47834T1 (de) | 1989-11-15 |
| FR2592376A1 (fr) | 1987-07-03 |
| DE3666806D1 (en) | 1989-12-14 |
| EP0232666A1 (fr) | 1987-08-19 |
| EP0232666B1 (fr) | 1989-11-08 |
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