CA1325219C - Fluoration d'orthocarbonates et de polyalkoxypropanes - Google Patents

Fluoration d'orthocarbonates et de polyalkoxypropanes

Info

Publication number: CA1325219C
Authority: CA; Canada
Prior art keywords: cf2cf3; orthocarbonate; fluorination; formula; hydrogen fluoride
Prior art date: 1987-08-28
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

CA000575907A

Other languages

English (en)

Inventor

Richard J. Lagow

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.)

1987-08-28

Filing date

1988-08-29

Publication date

1993-12-14

1988-08-29 Application filed by Exfluor Research Corp filed Critical Exfluor Research Corp

1993-12-14 Application granted granted Critical

1993-12-14 Publication of CA1325219C publication Critical patent/CA1325219C/fr

2010-12-14 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000003682 fluorination reaction Methods 0.000 title claims abstract description 24
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title description 4
235000013849 propane Nutrition 0.000 title description 3
-1 perfluoro compounds Chemical class 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 12
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 19
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 14
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 14
239000002516 radical scavenger Substances 0.000 claims description 13
239000007789 gas Substances 0.000 claims description 10
125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 10
125000006342 heptafluoro i-propyl group Chemical group FC(F)(F)C(F)(*)C(F)(F)F 0.000 claims description 9
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 4
235000013024 sodium fluoride Nutrition 0.000 claims description 4
239000011775 sodium fluoride Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000011261 inert gas Substances 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000008188 pellet Substances 0.000 claims description 2
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
235000003270 potassium fluoride Nutrition 0.000 claims 1
239000011698 potassium fluoride Substances 0.000 claims 1
239000000843 powder Substances 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 5
239000000969 carrier Substances 0.000 abstract description 5
239000001301 oxygen Substances 0.000 abstract description 5
229910052760 oxygen Inorganic materials 0.000 abstract description 5
239000002904 solvent Substances 0.000 abstract description 4
239000012808 vapor phase Substances 0.000 abstract description 3
239000012530 fluid Substances 0.000 abstract description 2
239000000314 lubricant Substances 0.000 abstract description 2
238000005476 soldering Methods 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 9
239000012634 fragment Substances 0.000 description 9
150000002500 ions Chemical class 0.000 description 9
239000000047 product Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
CWLNAJYDRSIKJS-UHFFFAOYSA-N triethoxymethoxyethane Chemical compound CCOC(OCC)(OCC)OCC CWLNAJYDRSIKJS-UHFFFAOYSA-N 0.000 description 5
238000000926 separation method Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
XHTYQFMRBQUCPX-UHFFFAOYSA-N 1,1,3,3-tetramethoxypropane Chemical compound COC(OC)CC(OC)OC XHTYQFMRBQUCPX-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000001307 helium Substances 0.000 description 3
229910052734 helium Inorganic materials 0.000 description 3
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000010702 perfluoropolyether Substances 0.000 description 3
AMHOKIZOZNVGMB-UHFFFAOYSA-N 1,1,2,2,3-pentafluoro-1,3,3-tris(1,1,2,2,2-pentafluoroethoxy)propane Chemical compound FC(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(OC(F)(F)C(F)(F)F)OC(F)(F)C(F)(F)F AMHOKIZOZNVGMB-UHFFFAOYSA-N 0.000 description 2
FYXAMJZVNPSHIA-UHFFFAOYSA-N 1,1,2,2,3-pentafluoro-1,3,3-tris(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(F)C(F)(F)C(F)(OC(F)(F)F)OC(F)(F)F FYXAMJZVNPSHIA-UHFFFAOYSA-N 0.000 description 2
KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 description 2
GEDZVKSFUOXWIL-UHFFFAOYSA-N 1,2,2,3-tetrafluoro-1,1,3,3-tetrakis(trifluoromethoxy)propane Chemical compound FC(F)(F)OC(F)(OC(F)(F)F)C(F)(F)C(F)(OC(F)(F)F)OC(F)(F)F GEDZVKSFUOXWIL-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
239000001294 propane Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
GEZOZTAXSFNENU-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluoro-3,3-bis(1,1,2,2,2-pentafluoroethoxy)propane Chemical compound FC(F)(F)C(F)(F)OC(F)(C(F)(F)C(F)(F)F)OC(F)(F)C(F)(F)F GEZOZTAXSFNENU-UHFFFAOYSA-N 0.000 description 1
JQQCBZMCIWOHNE-UHFFFAOYSA-N 1,2,2,3-tetrafluoro-1,1,3,3-tetrakis(1,1,2,2,2-pentafluoroethoxy)propane Chemical compound FC(F)(F)C(F)(F)OC(F)(OC(F)(F)C(F)(F)F)C(F)(F)C(F)(OC(F)(F)C(F)(F)F)OC(F)(F)C(F)(F)F JQQCBZMCIWOHNE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
101100328843 Dictyostelium discoideum cofB gene Proteins 0.000 description 1
241000264060 Lethrinus Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229920001774 Perfluoroether Polymers 0.000 description 1
101100038645 Streptomyces griseus rppA gene Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
150000004695 complexes Chemical class 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
238000006471 dimerization reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000243 solution Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
238000005829 trimerization reaction Methods 0.000 description 1
238000007514 turning Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/60—Preparation of compounds having groups or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/32—Compounds having groups or groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000575907A 1987-08-28 1988-08-29 Fluoration d'orthocarbonates et de polyalkoxypropanes Expired - Fee Related CA1325219C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US9065887A	1987-08-28	1987-08-28
US090,658		1987-08-28

Publications (1)

Publication Number	Publication Date
CA1325219C true CA1325219C (fr)	1993-12-14

Family

ID=22223721

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000575907A Expired - Fee Related CA1325219C (fr)	1987-08-28	1988-08-29	Fluoration d'orthocarbonates et de polyalkoxypropanes

Country Status (5)

Country	Link
EP (1)	EP0378574A1 (fr)
JP (1)	JPH03500172A (fr)
KR (1)	KR950004893B1 (fr)
CA (1)	CA1325219C (fr)
WO (1)	WO1989001929A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5300683A (en) *	1988-09-28	1994-04-05	Exfluor Research Corporation	Fluorination of acetals, ketals and orthoesters
US5053536A (en) *	1988-09-28	1991-10-01	Exfluor Research Corporation	Fluorination of acetals, ketals and orthoesters

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3415847A (en) *	1965-10-18	1968-12-10	Minnesota Mining & Mfg	Fluorocarbon orthoesters
US4113435A (en) *	1973-07-16	1978-09-12	Massachusetts Institute Of Technology	Cryogenically controlled direct fluorination apparatus
US4755567A (en) *	1985-11-08	1988-07-05	Exfluor Research Corporation	Perfluorination of ethers in the presence of hydrogen fluoride scavengers

1988
- 1988-08-26 JP JP63507916A patent/JPH03500172A/ja active Pending
- 1988-08-26 EP EP88908555A patent/EP0378574A1/fr not_active Withdrawn
- 1988-08-26 KR KR1019890700757A patent/KR950004893B1/ko not_active Expired - Lifetime
- 1988-08-26 WO PCT/US1988/002966 patent/WO1989001929A2/fr not_active Ceased
- 1988-08-29 CA CA000575907A patent/CA1325219C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
WO1989001929A3 (fr)	1989-06-01
JPH03500172A (ja)	1991-01-17
WO1989001929A2 (fr)	1989-03-09
EP0378574A1 (fr)	1990-07-25
KR890701523A (ko)	1989-12-20
KR950004893B1 (ko)	1995-05-15

Legal Events

Date	Code	Title	Description
1996-06-16	MKLA	Lapsed

Publication	Publication Date	Title
RU2144044C1 (ru)	2000-01-10	Фторированные производные бисвинилоксиметана (варианты), полимеры и сополимеры на их основе
EP0427820B1 (fr)	1995-06-14	Procede pour preparer des perfluoropolyethers peroxydiques
JP2594798B2 (ja)	1997-03-26	元素状ふっ素を用いたふっ素化によるペルフルオルエーテルの製造方法
RU2039055C1 (ru)	1995-07-09	Способ получения галоидированных 1,3-диоксоланов и галоидированные 1,3-диоксоланы
US4900872A (en)	1990-02-13	Process for the preparation of fluorohalogenated ethers starting from fluorooxy-compounds and halogenated olefins
CA1330351C (fr)	1994-06-21	Perfluoroalcanes obtenus par fluoration photochimique, et leur utilisation comme initiateurs de polymerisation
JPH0129175B2 (fr)	1989-06-08
EP0308905B1 (fr)	1995-04-19	Perfluoropolyéthers ayant des groupes terminaux mono- et bishypofluorites et procédé de leur préparation
JPS625932A (ja)	1987-01-12	フルオルハロエ−テル及びそれらの製造法
JP2846071B2 (ja)	1999-01-13	ペルハロオレフィンからのペルハロエーテルの製造方法およびそれによって得られる新規なペルハロエーテル
ZA200301572B (en)	2004-04-16	Process for preparation of fluorinated ketones.
CA1281306C (fr)	1991-03-12	Procede de fluoration en phase liquide de composes insatures
CA1325219C (fr)	1993-12-14	Fluoration d'orthocarbonates et de polyalkoxypropanes
US5235074A (en)	1993-08-10	Halogenated 1,3-dioxolanes
JP2562918B2 (ja)	1996-12-11	ハロゲン化ポリエーテルの製造方法
WO1989001928A1 (fr)	1989-03-09	Perfluoroethers spheriques et leur procede de preparation
US5075509A (en)	1991-12-24	Fluorination of orthocarbonates and polyalkoxy propanes
AU621312B2 (en)	1992-03-12	Fluorination of orthocarbonates and polyalkoxypropanes
EP1440994B1 (fr)	2007-03-28	Procédé pour la préparation de composés carbonyl monofonctionnels perfluorinés
US4225404A (en)	1980-09-30	Perfluoroolefin and perfluoroparaffin mixture and process for making same
JP2903109B2 (ja)	1999-06-07	モノ又はテトラフルオロエチルトリフルオロメチルエーテルの製造方法
EP1440993B1 (fr)	2008-04-09	Procédé pour la préparation de composés carbonyl monofonctionnels perfluorinés
Russo et al.	1995	The reaction of CF3OOCF2OF with fluoroolefins
EP0380129B1 (fr)	1993-12-08	Procédé de préparation de fluorures d'alpha-bromoacyles
WO2024111485A1 (fr)	2024-05-30	Procédé de production d'un composé fluoroester