US3843735A - 3-perfluoroalkyl-1 propenes and process for producing - Google Patents
3-perfluoroalkyl-1 propenes and process for producing Download PDFInfo
- Publication number
- US3843735A US3843735A US00177091A US17709171A US3843735A US 3843735 A US3843735 A US 3843735A US 00177091 A US00177091 A US 00177091A US 17709171 A US17709171 A US 17709171A US 3843735 A US3843735 A US 3843735A
- Authority
- US
- United States
- Prior art keywords
- percent
- perfluoroalkyl
- zinc
- allyl
- ether
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 11
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- 239000011701 zinc Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 229910052725 zinc Inorganic materials 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 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 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- -1 fluoroalkyl fumarates Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- LWJHSQQHGRQCKO-UHFFFAOYSA-N 1-prop-2-enoxypropane Chemical compound CCCOCC=C LWJHSQQHGRQCKO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 238000007342 radical addition reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- AHUMDLIBMIYQMU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7-pentadecafluoro-7-iodoheptane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I AHUMDLIBMIYQMU-UHFFFAOYSA-N 0.000 description 1
- BBZVTTKMXRPMHZ-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoro-2-iodopropane Chemical compound FC(F)(F)C(F)(I)C(F)(F)F BBZVTTKMXRPMHZ-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- NUPSHWCALHZGOV-UHFFFAOYSA-N acetic acid n-decyl ester Natural products CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 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 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/367—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by depolymerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
Definitions
- R is a long chain straight or branched perfluoroalkyl group of the formula C,,F where n is an integer from 3 to 14 and more preferably 6 to 12.
- the present compounds are useful intermediates for application in textile finishes.
- the 3-perfluoroalkyl-l-propenes of the present disclosure may be converted to fluoroalkyl fumarates which may be employed as textile finishes.
- the 3-perfluoroalkyl-l-propenes are formed by treatment of specific 3- perfluoroalkyl-Z-iodo-I-alkyl ethers or 3- point of economic consideration, R; desirably contains six to 12 carbon atoms.
- R groups-containing less than six carbon atoms do provide soil repellency in textile finishes. Nevertheless, due to industry standards of high repellency levels, an additional fluorine content is dea suitable R group contains seven carbon atoms.
- the present process is directed to the treatment of the disclosed 3-perfluoroalkyl-2-iodo-l alkyl ethers or esters with zinc to obtain terminal unsaturation rendering novelty to the present technique.
- a hydroxylic solvent may be employed in conjunction with the disclosed process.
- the present process employs the utilization of starting materials comprising fluorinated iodoalkyl ethers and esters with zinc.
- the fluorinated iodoalkyl compounds utilized in this technique are known in the art and may be prepared in accordance with Brace US. Pat. No. 3,145,222 and Brace, J. Org Chem. 27, 3033, (l962), namely: g
- R is a straight or branch chain perfluoroalkyl group containing three to 14 carbon atoms, and more desirably six to 12 carbon atoms.
- v The reaction to produce the 3-perfluoroalkyl-l propene is carried out in the presence of zinc. A hydroxylic solvent may be employed. Additionally a proton donor
- the Brace disclosure illustrates the principle that in reacting fluorinated iodoalkyl esters in the presence of zinc, reduction of the fluorinated alkyl iodide takes place, namely the replacement by iodine by hydrogen.
- the present invention employs starting compounds which are closely re- 7 lated to prior art starting compounds but forms a reactant product which is totally unexpected.
- R cH cH a cn cz ca omzn whereih Rji aiong chain perfluoroalkyl group either straight or branched chain of the formula C,,F where n is an integer from 3 to 14; R represents lower .alkyl containing one to four carbon atoms, lower acyl may be used in analogous fashion as prior art disclosures but a different result is obtained in the present use with the present selection of starting compounds. Suit- .239132 sa slaqsgssissss@QH.
- able solvents include methanol, isopropanol, cellosolves and ethylene glycol, etc.
- Proton donor systems if employed, can include hydrogen chloride, formic acid etc. and systems disclosed in the Haszeldine and Steele disclosures, supra.
- the addition of the acetate takes approximately 45 minutes.
- the reaction mixture is continuously stirred for an additional 2% hours and the temperature maintained at 60C. Thereafter the reaction mixture is cooled to room temperature, the unreacted zinc is filtered off and the product washed with 1500 ml. of water.
- the oily layer is dried over molecular sieve and then distilled through an 18 inch spinning band column; 19.6 grams of product boiling at 142l44C/760 mm. is obtained.
- EXAMPLE 8 Preparation of 4-'l"rifluoromethyl-4,5 ,5 ,S-tetrafluorol -pentene (CF11 from (CF CFCH CHlCH O CCH (30.0g, 0.0756 mole) was added slowly from a Varibor dropping funnel to a slurrly of zinc (10.0g, 0.153g-atom) in oxydiethanol (diethylene glycol, ml), while stirring by a magnet in a total reflux, partial take-off distilling apparatus connected to a Dry-Ice trap. The iodo acetate was.
- a Fischer Porter aerosol tube was charged with allyl benzoate (16.2 g, 0.100 mol), l-iodoperfluoroheptane (49.6 g, 0.100 mol, and azobisisobutyronitrile (0.328 g, 2.00 mmol). After the usual procedure the tube was heated at 70 for 12 hr, the reaction product (two layers) filtered through a sintered disc and distilled without a column, using a variable take-off head. C F, l (15.1 g, percent recovery) and allyl benzoate (1.7 g) were removed.
- the colorless clear mixture became cloudy. It was filtered through a sintered glass disc and distilled in column A. A mixture of C F, l and allyl propyl ether (657g, n D 1.3905), and C F, l (9.27g, n D 1.3300) were recovered; C F, CH Cl-llC1-l -OCl-l Cl-l Cl-l distilled, bp 81-83/0.85 mm, n D 1.3767, 42.65g (71.5 percent conversion). A residue of 1.0g remained. The trap contained 2.50g of starting materials (n D 1.3500).
- a process for the preparation of 3-perfluoroalkyl l-propene which comprises treating R CH CIIHCH OR I where Rf is CnF n is an integer from 3 to .14 and R is lower alkyl, lower carboxylac'yl, benzoyl or aryl, with zinc in the presence of an alkanol of one to three carbon atoms, a glycol of up to three carbon atoms, ethylene glycol or diethylene glycol.
- n is an integer from 6 to 12.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE788214D BE788214A (fr) | 1971-09-01 | Procede de production de 3-perfluoroalkyl-1-propenes | |
| US00177091A US3843735A (en) | 1971-09-01 | 1971-09-01 | 3-perfluoroalkyl-1 propenes and process for producing |
| GB3547772A GB1377235A (en) | 1971-09-01 | 1972-07-28 | Process for producing 3-perfluoroalkyl-1-propenes |
| DE2241252A DE2241252A1 (de) | 1971-09-01 | 1972-08-22 | Verfahren zur herstellung von 3-perfluoralkyl-1-propenen |
| JP47083384A JPS4834805A (de) | 1971-09-01 | 1972-08-22 | |
| FR7230560A FR2150915A1 (de) | 1971-09-01 | 1972-08-28 | |
| CH1268672A CH570949A5 (de) | 1971-09-01 | 1972-08-28 | |
| IT52426/72A IT962277B (it) | 1971-09-01 | 1972-08-30 | Procedimento per la produzione di 3 perfluoro alchil i propeni |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00177091A US3843735A (en) | 1971-09-01 | 1971-09-01 | 3-perfluoroalkyl-1 propenes and process for producing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3843735A true US3843735A (en) | 1974-10-22 |
Family
ID=22647155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00177091A Expired - Lifetime US3843735A (en) | 1971-09-01 | 1971-09-01 | 3-perfluoroalkyl-1 propenes and process for producing |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3843735A (de) |
| JP (1) | JPS4834805A (de) |
| BE (1) | BE788214A (de) |
| CH (1) | CH570949A5 (de) |
| DE (1) | DE2241252A1 (de) |
| FR (1) | FR2150915A1 (de) |
| GB (1) | GB1377235A (de) |
| IT (1) | IT962277B (de) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4900874A (en) * | 1988-02-12 | 1990-02-13 | Daikin Industries, Ltd. | Method for producing fluorine-containing olefin |
| WO2005074639A3 (en) * | 2004-01-30 | 2005-12-08 | Pcbu Services Inc | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| WO2005074593A3 (en) * | 2004-01-30 | 2006-03-16 | Pcbu Services Inc | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| WO2005074594A3 (en) * | 2004-01-30 | 2006-03-30 | Pcbu Services Inc | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| KR100945557B1 (ko) | 2008-04-28 | 2010-03-08 | 나노크리스탈주식회사 | 과불화알킬 변성 알킬알콕시실란의 제조방법 |
| WO2011085058A1 (en) | 2010-01-06 | 2011-07-14 | Nature Works Llc | Polylactide molding compositions and molding process |
| US8318656B2 (en) | 2007-07-03 | 2012-11-27 | E. I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| WO2017189452A1 (en) | 2016-04-28 | 2017-11-02 | Natureworks Llc | Polymer foam insulation structures having a facing layer of a polylactide resin |
| WO2017189453A1 (en) | 2016-04-28 | 2017-11-02 | Natureworks Llc | Polymer foam insulation structure having a facing of a multi-layer sheet that contains a heat resistant polymer layer and a polylactide resin layer |
-
0
- BE BE788214D patent/BE788214A/xx unknown
-
1971
- 1971-09-01 US US00177091A patent/US3843735A/en not_active Expired - Lifetime
-
1972
- 1972-07-28 GB GB3547772A patent/GB1377235A/en not_active Expired
- 1972-08-22 DE DE2241252A patent/DE2241252A1/de active Pending
- 1972-08-22 JP JP47083384A patent/JPS4834805A/ja active Pending
- 1972-08-28 FR FR7230560A patent/FR2150915A1/fr not_active Withdrawn
- 1972-08-28 CH CH1268672A patent/CH570949A5/xx not_active IP Right Cessation
- 1972-08-30 IT IT52426/72A patent/IT962277B/it active
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4900874A (en) * | 1988-02-12 | 1990-02-13 | Daikin Industries, Ltd. | Method for producing fluorine-containing olefin |
| WO2005074639A3 (en) * | 2004-01-30 | 2005-12-08 | Pcbu Services Inc | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| WO2005074593A3 (en) * | 2004-01-30 | 2006-03-16 | Pcbu Services Inc | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| WO2005074594A3 (en) * | 2004-01-30 | 2006-03-30 | Pcbu Services Inc | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| US20080009655A1 (en) * | 2004-01-30 | 2008-01-10 | Janet Boggs | Production Processes and Systems, Compositions, Surfactants, Monomer Units, Metal Complexes, Phosphate Esters, Glycols, Aqueous Film Forming Foams, and Foam Stabilizers |
| US7943567B2 (en) | 2004-01-30 | 2011-05-17 | E.I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| US8318656B2 (en) | 2007-07-03 | 2012-11-27 | E. I. Du Pont De Nemours And Company | Production processes and systems, compositions, surfactants, monomer units, metal complexes, phosphate esters, glycols, aqueous film forming foams, and foam stabilizers |
| KR100945557B1 (ko) | 2008-04-28 | 2010-03-08 | 나노크리스탈주식회사 | 과불화알킬 변성 알킬알콕시실란의 제조방법 |
| WO2011085058A1 (en) | 2010-01-06 | 2011-07-14 | Nature Works Llc | Polylactide molding compositions and molding process |
| WO2017189452A1 (en) | 2016-04-28 | 2017-11-02 | Natureworks Llc | Polymer foam insulation structures having a facing layer of a polylactide resin |
| WO2017189453A1 (en) | 2016-04-28 | 2017-11-02 | Natureworks Llc | Polymer foam insulation structure having a facing of a multi-layer sheet that contains a heat resistant polymer layer and a polylactide resin layer |
Also Published As
| Publication number | Publication date |
|---|---|
| IT962277B (it) | 1973-12-20 |
| DE2241252A1 (de) | 1973-03-08 |
| CH570949A5 (de) | 1975-12-31 |
| JPS4834805A (de) | 1973-05-22 |
| BE788214A (fr) | 1973-02-28 |
| GB1377235A (en) | 1974-12-11 |
| FR2150915A1 (de) | 1973-04-13 |
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