JPS6169745A - ヘキサフルオロイソブタン酸エステルの製造法 - Google Patents
ヘキサフルオロイソブタン酸エステルの製造法Info
- Publication number
- JPS6169745A JPS6169745A JP19279484A JP19279484A JPS6169745A JP S6169745 A JPS6169745 A JP S6169745A JP 19279484 A JP19279484 A JP 19279484A JP 19279484 A JP19279484 A JP 19279484A JP S6169745 A JPS6169745 A JP S6169745A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl ether
- alcohol
- acid ester
- heptafluoroisobutenyl
- hexafluoroisobutanoic
- 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
- -1 hexafluoroisobutanoic acid ester Chemical class 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 15
- 150000005215 alkyl ethers Chemical class 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 abstract description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- BSZWZZSFVRISOG-UHFFFAOYSA-N 1-ethoxy-1,3,3,3-tetrafluoro-2-(trifluoromethyl)prop-1-ene Chemical compound CCOC(F)=C(C(F)(F)F)C(F)(F)F BSZWZZSFVRISOG-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005796 dehydrofluorination reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JGGBVFLRNNDHCM-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound COC(=O)C(C(F)(F)F)C(F)(F)F JGGBVFLRNNDHCM-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VNLOISSPTMDCIF-VURMDHGXSA-N (z)-3-(2,4-dimethoxyphenyl)but-2-enoic acid Chemical compound COC1=CC=C(\C(C)=C/C(O)=O)C(OC)=C1 VNLOISSPTMDCIF-VURMDHGXSA-N 0.000 description 1
- SBOBNAIFNOATEG-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-methylpropane Chemical compound FC(F)C(F)(C)C(F)(F)F SBOBNAIFNOATEG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FSDLLONBRLBIBL-UHFFFAOYSA-N 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)prop-1-ene Chemical compound COC(F)=C(C(F)(F)F)C(F)(F)F FSDLLONBRLBIBL-UHFFFAOYSA-N 0.000 description 1
- AQHKYFLVHBIQMS-UHFFFAOYSA-N 2-[difluoro(methoxy)methyl]-1,1,1,3,3,3-hexafluoropropane Chemical compound COC(F)(F)C(C(F)(F)F)C(F)(F)F AQHKYFLVHBIQMS-UHFFFAOYSA-N 0.000 description 1
- RAEAYTICAPHWJW-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(C(F)(F)F)C(F)(F)F RAEAYTICAPHWJW-UHFFFAOYSA-N 0.000 description 1
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19279484A JPS6169745A (ja) | 1984-09-14 | 1984-09-14 | ヘキサフルオロイソブタン酸エステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19279484A JPS6169745A (ja) | 1984-09-14 | 1984-09-14 | ヘキサフルオロイソブタン酸エステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6169745A true JPS6169745A (ja) | 1986-04-10 |
| JPH037651B2 JPH037651B2 (en, 2012) | 1991-02-04 |
Family
ID=16297099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19279484A Granted JPS6169745A (ja) | 1984-09-14 | 1984-09-14 | ヘキサフルオロイソブタン酸エステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6169745A (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766238A (en) * | 1985-10-21 | 1988-08-23 | Daikin Industries, Ltd. | Fluorine-containing compounds, and their preparation and use |
| US6023002A (en) * | 1998-01-26 | 2000-02-08 | 3M Innovative Properties Company | Process for preparing hydrofluoroethers |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
| JP2009276059A (ja) * | 2009-08-24 | 2009-11-26 | Max Co Ltd | 空気清浄機 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7633637B2 (ja) | 2020-07-28 | 2025-02-20 | 株式会社ノベルクリスタルテクノロジー | 単結晶製造装置及び単結晶の製造方法 |
-
1984
- 1984-09-14 JP JP19279484A patent/JPS6169745A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766238A (en) * | 1985-10-21 | 1988-08-23 | Daikin Industries, Ltd. | Fluorine-containing compounds, and their preparation and use |
| US6023002A (en) * | 1998-01-26 | 2000-02-08 | 3M Innovative Properties Company | Process for preparing hydrofluoroethers |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
| JP2009276059A (ja) * | 2009-08-24 | 2009-11-26 | Max Co Ltd | 空気清浄機 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH037651B2 (en, 2012) | 1991-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |