CA1080253A - Process for the manufacture of perfluoro-alkoxy-propionic acid fluorides - Google Patents
Process for the manufacture of perfluoro-alkoxy-propionic acid fluoridesInfo
- Publication number
- CA1080253A CA1080253A CA281,134A CA281134A CA1080253A CA 1080253 A CA1080253 A CA 1080253A CA 281134 A CA281134 A CA 281134A CA 1080253 A CA1080253 A CA 1080253A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- perfluoro
- carbon atoms
- catalyst
- temperatures
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002798 polar solvent Substances 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- YLCLKCNTDGWDMD-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)F YLCLKCNTDGWDMD-UHFFFAOYSA-N 0.000 claims description 7
- BECUVKGRMKHUON-UHFFFAOYSA-N 1,1-difluoro-n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)C(F)(F)N(C)C BECUVKGRMKHUON-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 3
- OLTFUJYORRSUFZ-UHFFFAOYSA-N difluoromethanediamine Chemical class NC(N)(F)F OLTFUJYORRSUFZ-UHFFFAOYSA-N 0.000 abstract description 2
- 229920001774 Perfluoroether Polymers 0.000 abstract 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 7
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 3
- NSODUNDFRPXDAR-UHFFFAOYSA-N 3,3,3-trifluoro-2-oxopropanoyl fluoride Chemical compound FC(=O)C(=O)C(F)(F)F NSODUNDFRPXDAR-UHFFFAOYSA-N 0.000 description 3
- CWRPQPNYDDMAMA-UHFFFAOYSA-N 3,5,5,6-tetrafluoro-3,6-bis(trifluoromethyl)-1,4-dioxan-2-one Chemical compound FC(F)(F)C1(F)OC(F)(F)C(F)(C(F)(F)F)OC1=O CWRPQPNYDDMAMA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 lic acid fluorides Chemical class 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009183 running Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
- C07C59/135—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2627986A DE2627986C2 (de) | 1976-06-23 | 1976-06-23 | Verfahren zur Herstellung von Perfluoralkoxypropionsäurefluoriden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1080253A true CA1080253A (en) | 1980-06-24 |
Family
ID=5981172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA281,134A Expired CA1080253A (en) | 1976-06-23 | 1977-06-22 | Process for the manufacture of perfluoro-alkoxy-propionic acid fluorides |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4118421A (OSRAM) |
| JP (1) | JPS52156810A (OSRAM) |
| BE (1) | BE856041A (OSRAM) |
| CA (1) | CA1080253A (OSRAM) |
| DE (1) | DE2627986C2 (OSRAM) |
| FR (1) | FR2355796A1 (OSRAM) |
| GB (1) | GB1550268A (OSRAM) |
| IT (1) | IT1080241B (OSRAM) |
| NL (1) | NL187572C (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5551032A (en) * | 1978-10-06 | 1980-04-14 | Neos Co Ltd | Preparation of hexafluoroepoxypropane oligomer |
| US4786442A (en) * | 1980-04-03 | 1988-11-22 | E. I. Du Pont De Nemours And Company | Alkyl perfluoro(2-methyl-5-oxo-3-oxahexanoate) |
| IT1186708B (it) * | 1985-05-28 | 1987-12-16 | Montefluos Spa | Processo per la preparazione di 2-perfluoropropossi-perfluoropropio nilfluoruro |
| US4749526A (en) * | 1986-09-12 | 1988-06-07 | Minnesota Mining And Manufacturing Co. | Process for preparing fluoraliphatic ether-containing carbonyl fluoride compositions |
| US5153322A (en) * | 1987-10-30 | 1992-10-06 | Minnesota Mining And Manufacturing Company | Perfluoro (cycloaliphatic methyleneoxyalkylene) carbonyl fluorides and derivatives thereof |
| US5210282A (en) * | 1987-10-30 | 1993-05-11 | Minnesota Mining And Manufacturing Company | Perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluorides and derivatives thereof |
| US4889656A (en) * | 1987-10-30 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluorides and derivatives thereof |
| DE3737920A1 (de) * | 1987-11-07 | 1989-05-18 | Hoechst Ag | Verfahren zur herstellung von perfluorierten carbonsaeurefluoriden |
| JPH024733A (ja) * | 1988-06-23 | 1990-01-09 | Nippon Mektron Ltd | パーフルオロ（２‐メトキシプロピオン酸）フロリドの製造法 |
| DE3901000A1 (de) * | 1989-01-14 | 1990-07-19 | Hoechst Ag | Verfahren zur oligomerisation von hexafluorpropenoxid |
| DE3901002A1 (de) * | 1989-01-14 | 1990-07-26 | Hoechst Ag | Verfahren zur dimerisierung von hexafluorpropenoxid |
| US5658962A (en) * | 1994-05-20 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application |
| US5476974A (en) * | 1994-05-20 | 1995-12-19 | Minnesota Mining And Manufacturing Company | Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application |
| US5777179A (en) * | 1996-05-24 | 1998-07-07 | E. I. Du Pont De Nemours And Company | Co-production of perfluoromethyl perfluorovinyl ether and perfluoroethyl perfluorovinyl ether |
| US6329529B1 (en) * | 1997-08-06 | 2001-12-11 | Mitsui Chemicals, Inc. | Nitrogen-based halogenating agents and process for preparing halogen-containing compounds |
| RU2230057C1 (ru) * | 2002-11-18 | 2004-06-10 | Игумнов Сергей Михайлович | Способ получения фторангидридов полифторированных алкоксипропионовых кислот |
| JP5521463B2 (ja) * | 2008-10-01 | 2014-06-11 | ダイキン工業株式会社 | フルオロエーテルカルボン酸フルオライド及びフルオロエーテルカルボン酸の製造方法 |
| EP3659964A1 (en) | 2018-11-28 | 2020-06-03 | Hysilabs, SAS | Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA707361A (en) * | 1965-04-06 | P. Moore Earl | Fluorocarbon polyethers | |
| DE1645115B1 (de) * | 1962-04-11 | 1971-11-18 | Du Pont | Verfahren zur Herstellung von Hexafluorpropylenepoxyd-Polymerisaten |
| US3322826A (en) * | 1962-04-11 | 1967-05-30 | Du Pont | Polymerization of hexafluoropropylene epoxide |
| FR1362548A (fr) * | 1963-04-09 | 1964-06-05 | Du Pont | Polyéthers fluorocarbonés et leur procédé de préparation |
| US3321532A (en) * | 1963-10-08 | 1967-05-23 | Du Pont | Fluorocarbon ethers |
| US3250808A (en) * | 1963-10-31 | 1966-05-10 | Du Pont | Fluorocarbon ethers derived from hexafluoropropylene epoxide |
| GB1292268A (en) | 1970-02-16 | 1972-10-11 | Bitterfeld Chemie | Process for the dimerisation of hexafluoropropene epoxide |
-
1976
- 1976-06-23 DE DE2627986A patent/DE2627986C2/de not_active Expired
-
1977
- 1977-06-17 NL NLAANVRAGE7706709,A patent/NL187572C/xx not_active IP Right Cessation
- 1977-06-21 US US05/808,537 patent/US4118421A/en not_active Expired - Lifetime
- 1977-06-21 IT IT24916/77A patent/IT1080241B/it active
- 1977-06-22 JP JP7339877A patent/JPS52156810A/ja active Granted
- 1977-06-22 CA CA281,134A patent/CA1080253A/en not_active Expired
- 1977-06-23 GB GB26311/77A patent/GB1550268A/en not_active Expired
- 1977-06-23 FR FR7719232A patent/FR2355796A1/fr active Granted
- 1977-06-23 BE BE178721A patent/BE856041A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1080241B (it) | 1985-05-16 |
| BE856041A (fr) | 1977-12-23 |
| GB1550268A (en) | 1979-08-15 |
| DE2627986A1 (de) | 1978-01-05 |
| NL187572B (nl) | 1991-06-17 |
| NL7706709A (nl) | 1977-12-28 |
| FR2355796A1 (fr) | 1978-01-20 |
| JPS611416B2 (OSRAM) | 1986-01-17 |
| DE2627986C2 (de) | 1985-02-14 |
| JPS52156810A (en) | 1977-12-27 |
| FR2355796B1 (OSRAM) | 1982-03-19 |
| US4118421A (en) | 1978-10-03 |
| NL187572C (nl) | 1991-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |