JPS6363633A - ３，３，３−トリフルオロプロパナ−ルの製造法 - Google Patents
３，３，３−トリフルオロプロパナ−ルの製造法Info
- Publication number
- JPS6363633A JPS6363633A JP61208051A JP20805186A JPS6363633A JP S6363633 A JPS6363633 A JP S6363633A JP 61208051 A JP61208051 A JP 61208051A JP 20805186 A JP20805186 A JP 20805186A JP S6363633 A JPS6363633 A JP S6363633A
- Authority
- JP
- Japan
- Prior art keywords
- palladium
- reaction
- water
- trifluoropropanal
- trifluoropropene
- 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
- UTMIEQASUFFADK-UHFFFAOYSA-N 3,3,3-trifluoropropanal Chemical compound FC(F)(F)CC=O UTMIEQASUFFADK-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002940 palladium Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052763 palladium Inorganic materials 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 239000007800 oxidant agent Substances 0.000 abstract description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 abstract description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract description 2
- 229940045803 cuprous chloride Drugs 0.000 abstract description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 abstract description 2
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- FFTOUVYEKNGDCM-OWOJBTEDSA-N (e)-1,3,3-trifluoroprop-1-ene Chemical compound F\C=C\C(F)F FFTOUVYEKNGDCM-OWOJBTEDSA-N 0.000 description 1
- HMAHQANPHFVLPT-UHFFFAOYSA-N 1,3,3-trifluoroprop-1-yne Chemical compound FC#CC(F)F HMAHQANPHFVLPT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61208051A JPS6363633A (ja) | 1986-09-05 | 1986-09-05 | ３，３，３−トリフルオロプロパナ−ルの製造法 |
| GB8720398A GB2196002B (en) | 1986-09-05 | 1987-08-28 | Preparation of polyfluoroaldehydes and polyfluoroacetals |
| US07/092,680 US4837366A (en) | 1986-09-05 | 1987-09-03 | Preparation of polyfluoroaldehydes and polyfluoroacetals |
| DE19873729734 DE3729734A1 (de) | 1986-09-05 | 1987-09-04 | Verfahren zur herstellung von polyfluoraldehyden und polyfluoracetalen |
| FR878712318A FR2603580B1 (fr) | 1986-09-05 | 1987-09-04 | Procede de preparation d'un compose organique polyfluorure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61208051A JPS6363633A (ja) | 1986-09-05 | 1986-09-05 | ３，３，３−トリフルオロプロパナ−ルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6363633A true JPS6363633A (ja) | 1988-03-22 |
| JPH0586937B2 JPH0586937B2 (enrdf_load_stackoverflow) | 1993-12-14 |
Family
ID=16549831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61208051A Granted JPS6363633A (ja) | 1986-09-05 | 1986-09-05 | ３，３，３−トリフルオロプロパナ−ルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6363633A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007119447A (ja) * | 2005-09-29 | 2007-05-17 | Central Glass Co Ltd | ３，３，３−トリフルオロプロピオンアルデヒドの製造方法 |
| JP2008208090A (ja) * | 2007-02-27 | 2008-09-11 | Mitsubishi Chemicals Corp | カルボニル化合物の製造法及びこれに用いられる遷移金属錯体 |
| US7544844B2 (en) | 2005-09-29 | 2009-06-09 | Central Glass Company, Limited | Process for producing 3,3,3-trifluoropropionaldehyde |
| US7880033B2 (en) | 2005-11-01 | 2011-02-01 | Central Glass Company, Limited | Process for producing 3,3,3-trifluoropropionic acid |
-
1986
- 1986-09-05 JP JP61208051A patent/JPS6363633A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007119447A (ja) * | 2005-09-29 | 2007-05-17 | Central Glass Co Ltd | ３，３，３−トリフルオロプロピオンアルデヒドの製造方法 |
| US7544844B2 (en) | 2005-09-29 | 2009-06-09 | Central Glass Company, Limited | Process for producing 3,3,3-trifluoropropionaldehyde |
| US7880033B2 (en) | 2005-11-01 | 2011-02-01 | Central Glass Company, Limited | Process for producing 3,3,3-trifluoropropionic acid |
| JP2008208090A (ja) * | 2007-02-27 | 2008-09-11 | Mitsubishi Chemicals Corp | カルボニル化合物の製造法及びこれに用いられる遷移金属錯体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0586937B2 (enrdf_load_stackoverflow) | 1993-12-14 |
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