CA1283129C - Pyrolyse de perfluoropolyethers - Google Patents

Pyrolyse de perfluoropolyethers

Info

Publication number: CA1283129C
Authority: CA; Canada
Prior art keywords: molecular weight; lower molecular; perfluoropolyethers; perfluoropolyether; perfluoropoly
Prior art date: 1985-11-08
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

Application number

CA000522463A

Other languages

English (en)

Inventor

Richard J. Lagow

Thomas R. Bierschenk

Hajimu M. Kawa

Timothy J. Juhlke

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Exfluor Research Corp

Original Assignee

Exfluor Research Corp

Priority date (The priority date 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 date listed.)

1985-11-08

Filing date

1986-11-07

Publication date

1991-04-16

1986-11-07 Application filed by Exfluor Research Corp filed Critical Exfluor Research Corp

1991-04-16 Application granted granted Critical

1991-04-16 Publication of CA1283129C publication Critical patent/CA1283129C/fr

2008-04-16 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000010702 perfluoropolyether Substances 0.000 title claims abstract description 82
238000000197 pyrolysis Methods 0.000 title claims abstract description 38
238000000034 method Methods 0.000 claims abstract description 33
239000012634 fragment Substances 0.000 claims abstract description 12
238000004821 distillation Methods 0.000 claims abstract description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 25
229910052731 fluorine Inorganic materials 0.000 claims description 25
239000011737 fluorine Substances 0.000 claims description 25
239000007789 gas Substances 0.000 claims description 25
229920000642 polymer Polymers 0.000 claims description 23
150000001265 acyl fluorides Chemical group 0.000 claims description 14
239000003921 oil Substances 0.000 claims description 14
238000010438 heat treatment Methods 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 13
239000011261 inert gas Substances 0.000 claims description 8
229910044991 metal oxide Inorganic materials 0.000 claims description 7
150000004706 metal oxides Chemical class 0.000 claims description 7
229910001512 metal fluoride Inorganic materials 0.000 claims description 5
229920001577 copolymer Polymers 0.000 claims description 4
LOUICXNAWQPGSU-UHFFFAOYSA-N 2,2,3,3-tetrafluorooxirane Chemical compound FC1(F)OC1(F)F LOUICXNAWQPGSU-UHFFFAOYSA-N 0.000 claims description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000012530 fluid Substances 0.000 description 15
229910052759 nickel Inorganic materials 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000009826 distribution Methods 0.000 description 4
PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000003682 fluorination reaction Methods 0.000 description 3
125000005010 perfluoroalkyl group Chemical group 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000010926 purge Methods 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
BFXAWOHHDUIALU-UHFFFAOYSA-M sodium;hydron;difluoride Chemical compound F.[F-].[Na+] BFXAWOHHDUIALU-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 1
KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
101100328843 Dictyostelium discoideum cofB gene Proteins 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
208000032826 Ring chromosome 3 syndrome Diseases 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000003570 air Substances 0.000 description 1
238000010539 anionic addition polymerization reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000010504 bond cleavage reaction Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 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
229920006158 high molecular weight polymer Polymers 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
-1 polytetramethylene Polymers 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000565 sealant Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
238000004227 thermal cracking Methods 0.000 description 1
XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
238000004448 titration Methods 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
- C08G65/002—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
- 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)
Polyethers (AREA)
Lubricants (AREA)

CA000522463A 1985-11-08 1986-11-07 Pyrolyse de perfluoropolyethers Expired - Fee Related CA1283129C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US79662485A	1985-11-08	1985-11-08
US796,624		1985-11-08

Publications (1)

Publication Number	Publication Date
CA1283129C true CA1283129C (fr)	1991-04-16

Family

ID=25168638

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000522463A Expired - Fee Related CA1283129C (fr)	1985-11-08	1986-11-07	Pyrolyse de perfluoropolyethers

Country Status (6)

Country	Link
EP (1)	EP0256024A1 (fr)
JP (1)	JPS63501299A (fr)
KR (1)	KR880700838A (fr)
BR (1)	BR8606970A (fr)
CA (1)	CA1283129C (fr)
WO (1)	WO1987002995A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6413242B1 (en)	1996-07-05	2002-07-02	Disetronic Licensing Ag	Injection device for injection of liquid
CN115181257B (zh) *	2022-08-09	2023-06-09	浙江巨化技术中心有限公司	一种降低全氟聚醚分子量的方法
KR20260037113A (ko)	2023-07-14	2026-03-17	클라로스 테크놀로지스 인코포레이티드	수용액에서 요오드를 포획하는 방법 및 시스템
US12545601B2 (en)	2023-07-14	2026-02-10	Claros Technologies Inc.	Methods and systems of photosensitizer recovery for improved PFAS destruction
US12534390B2 (en)	2023-07-14	2026-01-27	Claros Technologies Inc.	Methods and systems of nitrate removal in aqueous systems for improved PFAS destruction

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3242218A (en) *	1961-03-29	1966-03-22	Du Pont	Process for preparing fluorocarbon polyethers
FR1530862A (fr) *	1966-07-11	1968-06-28	Montedison Spa	Cétones fluorées et procédé pour les préparer
IL31863A0 (en) *	1968-04-23	1969-05-28	Du Pont	4-phenyl(substituted bicyclo(2.2.2)octene)-1-carboxylic acids related compounds and pharmaceutical compositions containing them
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
BE764110A (fr) *	1970-03-12	1971-09-13	Montedison Spa	Nouveaux perfluoropolyethers possedant une structure cyclique et procede de preparation de ces corps
US4523039A (en) *	1980-04-11	1985-06-11	The University Of Texas	Method for forming perfluorocarbon ethers
CA1263405A (fr) *	1984-05-23	1989-11-28	Giantommaso Viola	Preparation de perfluoropolyethers neutres et fonctionnels a masse moleculaire controlee

1986
- 1986-10-31 EP EP86907094A patent/EP0256024A1/fr not_active Withdrawn
- 1986-10-31 BR BR8606970A patent/BR8606970A/pt unknown
- 1986-10-31 WO PCT/US1986/002345 patent/WO1987002995A1/fr not_active Ceased
- 1986-10-31 JP JP61506093A patent/JPS63501299A/ja active Pending
- 1986-11-07 CA CA000522463A patent/CA1283129C/fr not_active Expired - Fee Related
1987
- 1987-07-08 KR KR870700593A patent/KR880700838A/ko not_active Ceased

Also Published As

Publication number	Publication date
AU590646B2 (en)	1989-11-09
EP0256024A1 (fr)	1988-02-24
KR880700838A (ko)	1988-04-12
WO1987002995A1 (fr)	1987-05-21
BR8606970A (pt)	1987-12-01
JPS63501299A (ja)	1988-05-19
AU6622186A (en)	1987-06-02

Legal Events

Date	Code	Title	Description
1993-10-18	MKLA	Lapsed

Publication	Publication Date	Title
EP0427820B1 (fr)	1995-06-14	Procede pour preparer des perfluoropolyethers peroxydiques
KR0126237B1 (ko)	1997-12-26	퍼플루오르알킬 또는 퍼플루오르클로로알킬말단기를 갖는 조절된 분자량의 퍼플루오르폴리에테르의 제조방법
KR101589770B1 (ko)	2016-02-01	(퍼)플루오르화 첨가 생성물
AU596176B2 (en)	1990-04-26	Perfluorpolyethers free from peroxidic oxygen and containing perfluoroepoxy groups positioned along their perfluoropolyether chain
CA1281337C (fr)	1991-03-12	Copolymere d'oxyde de difluoromethylene et d'oxyde de tetrafluoroethylene
CA1266750A (fr)	1990-03-13	Perfluoropolyethers bifonctionnels et monofonctionnels a groupes terminaux bromes et a masse moleculaire selectionnee
IT9019585A1 (it)	1991-09-06	Perfluoropolieteri e processi per la loro preparazione
US4894484A (en)	1990-01-16	Pyrolysis of perfluoropolyethers
EP2373720B1 (fr)	2012-11-07	(per)fluoropolyéthers polyfonctionnels
CA1283129C (fr)	1991-04-16	Pyrolyse de perfluoropolyethers
US5025093A (en)	1991-06-18	Pyrolysis of perfluoropolyethers
WO1997028205A1 (fr)	1997-08-07	Procede d'oxydation d'olefines
CA1305494C (fr)	1992-07-21	Procede pour la preparation de perfluoropolyesters a poids moleculaires predetermines, a groupes terminaux neutres et fonctionnels
AU590646C (en)	1990-10-18	The pyrolysis of perfluoropolyethers
KR0127859B1 (ko)	1998-04-04	과플루오로폴리에테르의 제조방법
EP1371677B1 (fr)	2008-04-09	Polyéthers perfluorés contenant des unités obtenues par oxidation des dioxolènes perfluorés
AU591219C (en)	1990-10-18	Copolymer of difluoromethylene oxide and tetrafluoroethylene oxide