CA2197537C - Process for preparing peroxidic perfluoropolyethers - Google Patents
Process for preparing peroxidic perfluoropolyethers Download PDFInfo
- Publication number
- CA2197537C CA2197537C CA002197537A CA2197537A CA2197537C CA 2197537 C CA2197537 C CA 2197537C CA 002197537 A CA002197537 A CA 002197537A CA 2197537 A CA2197537 A CA 2197537A CA 2197537 C CA2197537 C CA 2197537C
- Authority
- CA
- Canada
- Prior art keywords
- oxidation process
- process according
- tetrafluoroethylene
- perfluoropolyethers
- comprised
- 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 - Fee Related
Links
- 239000010702 perfluoropolyether Substances 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000002904 solvent Substances 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 30
- 230000003647 oxidation Effects 0.000 claims abstract description 18
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 18
- 230000005855 radiation Effects 0.000 claims abstract description 8
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims description 6
- 229960004065 perflutren Drugs 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 claims description 3
- LGUZHRODIJCVOC-UHFFFAOYSA-N perfluoroheptane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LGUZHRODIJCVOC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 238000003682 fluorination reaction Methods 0.000 claims description 2
- 239000000852 hydrogen donor Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000007669 thermal treatment Methods 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 7
- 239000012190 activator Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 4
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 4
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 4
- 238000007539 photo-oxidation reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI000278A IT1282626B1 (it) | 1996-02-14 | 1996-02-14 | Processo di preparazione di perfluoropolieteri perossidici |
| ITMI96A000278 | 1996-02-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2197537A1 CA2197537A1 (en) | 1997-08-15 |
| CA2197537C true CA2197537C (en) | 2005-02-08 |
Family
ID=11373266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002197537A Expired - Fee Related CA2197537C (en) | 1996-02-14 | 1997-02-13 | Process for preparing peroxidic perfluoropolyethers |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5783789A (forum.php) |
| EP (1) | EP0790268B1 (forum.php) |
| JP (1) | JP3907257B2 (forum.php) |
| KR (1) | KR100458611B1 (forum.php) |
| AT (1) | ATE217642T1 (forum.php) |
| CA (1) | CA2197537C (forum.php) |
| DE (1) | DE69712549T2 (forum.php) |
| IT (1) | IT1282626B1 (forum.php) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20011340A1 (it) * | 2001-06-26 | 2002-12-26 | Ausimont Spa | Pfpe aventi almeno un terminale alchiletereo e relativo processo dipreparazione |
| ITMI20031915A1 (it) * | 2003-10-03 | 2005-04-04 | Solvay Solexis Spa | Processo per la preparazione di perfluoropolieteri. |
| ITMI20050383A1 (it) * | 2005-03-10 | 2006-09-11 | Solvay Solexis Spa | Processo per preparare perfluoropolieteri perossidici |
| ITMI20050384A1 (it) * | 2005-03-10 | 2006-09-11 | Solvay Solexis Spa | Processo per preparare perfluoropolieteri perossidici |
| JP4470774B2 (ja) * | 2005-03-18 | 2010-06-02 | トヨタ自動車株式会社 | 内燃機関の制御装置 |
| JP5456769B2 (ja) * | 2008-08-15 | 2014-04-02 | チョンハオ チェングァン リサーチ インスティテュート オブ ケミカル インダストリー | 含フッ素ポリエーテルペルオキシド及びそれらの含フッ素単量体の乳化重合における応用 |
| CN102464730B (zh) * | 2010-11-02 | 2013-12-25 | 中昊晨光化工研究院 | 含氟微乳的制备方法及应用 |
| CN109415503B (zh) | 2016-07-05 | 2021-07-30 | 大金工业株式会社 | 过氧化氟代聚氧化烯烃化合物的制造方法 |
| KR102029997B1 (ko) * | 2017-12-08 | 2019-10-08 | 한국화학연구원 | 선형 퍼플루오로폴리에테르 합성을 위한 과산화 퍼플루오로폴리에테르 중간체 제조장치 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4451646A (en) * | 1967-02-09 | 1984-05-29 | Montedison, S.P.A. | High molecular weight polymeric perfluorinated copolyethers and process for their preparation from tetrafluoroethylene |
| DE1745169B2 (de) * | 1967-02-09 | 1977-04-21 | Montecatini Edison S.P.A., Mailand (Italien) | Fluorierte lineare polyaether und verfahren zu ihrer herstellung |
| GB1226566A (forum.php) * | 1967-04-04 | 1971-03-31 | ||
| US3847978A (en) * | 1968-07-01 | 1974-11-12 | Montedison Spa | Perfluorinated linear polyethers having reactive terminal groups at both ends of the chain and process for the preparation thereof |
| IT1150705B (it) * | 1982-03-19 | 1986-12-17 | Montedison Spa | Processo di inserimento di perfluoroolefine su perfluoropolieteri e prodotti relativi |
| US4858299A (en) * | 1985-02-15 | 1989-08-22 | Wing George S | Process for making a joint with a torque-limited collar |
| IT1185518B (it) * | 1985-02-22 | 1987-11-12 | Montefluos Spa | Ottenimento di perfluoropolieteri a peso molecolare controllato dal prodotto di ossidazione fotochimica del c2f4 |
| IT1229845B (it) * | 1989-04-20 | 1991-09-13 | Ausimont Srl | Procedimento per la preparazione di perfluoropolieteri perossidici. |
| IT1249319B (it) * | 1991-04-26 | 1995-02-22 | Ausimont Spa | Perfluoropolieteri ad elevata viscosita' e basso contenuto di ossigeno perossidico, e procedimento per la loro preparazione |
| US5182342A (en) * | 1992-02-28 | 1993-01-26 | E. I. Du Pont De Nemours And Company | Hydrofluorocarbon solvents for fluoromonomer polymerization |
| IT1264977B1 (it) * | 1993-11-17 | 1996-10-17 | Ausimont Spa | Processo per preparare perfluoropolietri |
| IT1274591B (it) * | 1994-08-05 | 1997-07-18 | Ausimont Spa | Processo per la preparazione di poliossiperfluoroalcani idrogeno terminati |
-
1996
- 1996-02-14 IT IT96MI000278A patent/IT1282626B1/it active IP Right Grant
-
1997
- 1997-02-11 AT AT97102122T patent/ATE217642T1/de not_active IP Right Cessation
- 1997-02-11 DE DE69712549T patent/DE69712549T2/de not_active Expired - Lifetime
- 1997-02-11 EP EP97102122A patent/EP0790268B1/en not_active Expired - Lifetime
- 1997-02-12 JP JP02763997A patent/JP3907257B2/ja not_active Expired - Fee Related
- 1997-02-13 KR KR1019970004274A patent/KR100458611B1/ko not_active Expired - Lifetime
- 1997-02-13 CA CA002197537A patent/CA2197537C/en not_active Expired - Fee Related
- 1997-02-14 US US08/800,017 patent/US5783789A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2197537A1 (en) | 1997-08-15 |
| JP3907257B2 (ja) | 2007-04-18 |
| KR100458611B1 (ko) | 2005-04-06 |
| EP0790268A2 (en) | 1997-08-20 |
| ITMI960278A1 (it) | 1997-08-14 |
| EP0790268A3 (en) | 1998-10-07 |
| DE69712549T2 (de) | 2003-01-16 |
| DE69712549D1 (de) | 2002-06-20 |
| KR970061934A (ko) | 1997-09-12 |
| IT1282626B1 (it) | 1998-03-31 |
| US5783789A (en) | 1998-07-21 |
| ITMI960278A0 (forum.php) | 1996-02-14 |
| EP0790268B1 (en) | 2002-05-15 |
| JPH09227507A (ja) | 1997-09-02 |
| ATE217642T1 (de) | 2002-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |