JPS61277645A - ヘキサフルオロアセトンの製造法 - Google Patents
ヘキサフルオロアセトンの製造法Info
- Publication number
- JPS61277645A JPS61277645A JP12032285A JP12032285A JPS61277645A JP S61277645 A JPS61277645 A JP S61277645A JP 12032285 A JP12032285 A JP 12032285A JP 12032285 A JP12032285 A JP 12032285A JP S61277645 A JPS61277645 A JP S61277645A
- Authority
- JP
- Japan
- Prior art keywords
- hexafluoroacetone
- alkyl ether
- produced
- production
- product
- 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
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- -1 heptafluoroisobutenyl alkyl ether Chemical class 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000006227 byproduct Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 3
- 150000005215 alkyl ethers Chemical class 0.000 abstract description 2
- 239000002585 base Substances 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical compound FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 4
- HEBNOKIGWWEWCN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;hydrate Chemical compound O.FC(F)(F)C(=O)C(F)(F)F HEBNOKIGWWEWCN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- LCRBBUPAHHPMMY-UHFFFAOYSA-N 1,3,3,3-tetrafluoro-1-[1,3,3,3-tetrafluoro-2-(trifluoromethyl)prop-1-enoxy]-2-(trifluoromethyl)prop-1-ene Chemical compound FC(F)(F)C(C(F)(F)F)=C(F)OC(F)=C(C(F)(F)F)C(F)(F)F LCRBBUPAHHPMMY-UHFFFAOYSA-N 0.000 description 2
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000010813 internal standard method Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 229930187593 rose bengal Natural products 0.000 description 2
- 229940081623 rose bengal Drugs 0.000 description 2
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Landscapes
- Physical Or Chemical Processes And Apparatus (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12032285A JPS61277645A (ja) | 1985-06-03 | 1985-06-03 | ヘキサフルオロアセトンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12032285A JPS61277645A (ja) | 1985-06-03 | 1985-06-03 | ヘキサフルオロアセトンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61277645A true JPS61277645A (ja) | 1986-12-08 |
| JPS6411624B2 JPS6411624B2 (enrdf_load_stackoverflow) | 1989-02-27 |
Family
ID=14783382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12032285A Granted JPS61277645A (ja) | 1985-06-03 | 1985-06-03 | ヘキサフルオロアセトンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61277645A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4885398A (en) * | 1987-07-21 | 1989-12-05 | Nippon Mektron Limited | Process for producing hexafluoroacetone or its hydrate |
| JP2001081056A (ja) * | 1999-09-13 | 2001-03-27 | Nippon Mektron Ltd | ヘキサフルオロアセトンまたはその水和物の製造法 |
| US6274005B1 (en) * | 2000-05-26 | 2001-08-14 | Halocarbon Products Corporation | Method for the preparation of hexafluoroacetone |
| WO2007142110A1 (ja) | 2006-06-05 | 2007-12-13 | Daikin Industries, Ltd. | 新規カルボン酸化合物、その用途及びその製造方法 |
| WO2008004466A1 (fr) | 2006-07-06 | 2008-01-10 | Daikin Industries, Ltd. | NOUVEL ESTER α-FLUOROMÉTHOXYCARBOXYLIQUE, PROCÉDÉ DE FABRICATION DE L'ESTER α-FLUOROMÉTHOXYCARBOXYLIQUE ET PROCÉDÉ DE FABRICATION DE SÉVOFLURANE |
| WO2009063783A1 (ja) | 2007-11-13 | 2009-05-22 | Daikin Industries, Ltd. | 新規カルボン酸エステル、その用途及びその製造方法 |
| US7598425B2 (en) | 2004-04-19 | 2009-10-06 | Daikin Industries, Ltd. | Method for producing hydrate of fluoroalkyl ketone |
-
1985
- 1985-06-03 JP JP12032285A patent/JPS61277645A/ja active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4885398A (en) * | 1987-07-21 | 1989-12-05 | Nippon Mektron Limited | Process for producing hexafluoroacetone or its hydrate |
| JP2001081056A (ja) * | 1999-09-13 | 2001-03-27 | Nippon Mektron Ltd | ヘキサフルオロアセトンまたはその水和物の製造法 |
| US6274005B1 (en) * | 2000-05-26 | 2001-08-14 | Halocarbon Products Corporation | Method for the preparation of hexafluoroacetone |
| WO2001092270A3 (en) * | 2000-05-26 | 2003-10-16 | Halocarbon Prod Corp | An improved method for the preparation of hexafluoroacetone |
| US7598425B2 (en) | 2004-04-19 | 2009-10-06 | Daikin Industries, Ltd. | Method for producing hydrate of fluoroalkyl ketone |
| WO2007142110A1 (ja) | 2006-06-05 | 2007-12-13 | Daikin Industries, Ltd. | 新規カルボン酸化合物、その用途及びその製造方法 |
| US7985877B2 (en) | 2006-06-05 | 2011-07-26 | Daikin Industries, Ltd. | Carboxylic acid compound, use thereof, and process for producing the same |
| EP2479161A1 (en) | 2006-06-05 | 2012-07-25 | Daikin Industries, Ltd. | A novel process for producing 1,1,1,3,3,3-hexafluoro-2-methoxypropane |
| WO2008004466A1 (fr) | 2006-07-06 | 2008-01-10 | Daikin Industries, Ltd. | NOUVEL ESTER α-FLUOROMÉTHOXYCARBOXYLIQUE, PROCÉDÉ DE FABRICATION DE L'ESTER α-FLUOROMÉTHOXYCARBOXYLIQUE ET PROCÉDÉ DE FABRICATION DE SÉVOFLURANE |
| US8022245B2 (en) | 2006-07-06 | 2011-09-20 | Daikin Industries, Ltd. | Alpha-fluoromethoxycarboxylic ester, process for producing the alpha-fluoromethoxycarboxylic ester, and process for producing sevoflurane |
| WO2009063783A1 (ja) | 2007-11-13 | 2009-05-22 | Daikin Industries, Ltd. | 新規カルボン酸エステル、その用途及びその製造方法 |
| US8013182B2 (en) | 2007-11-13 | 2011-09-06 | Daikin Industries, Ltd. | Carboxylic acid ester, use of the same, and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6411624B2 (enrdf_load_stackoverflow) | 1989-02-27 |
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