WO2007144599A3 - Production of fluorinated cyclopropanes from the reaction between carbenes and alkenes - Google Patents

Production of fluorinated cyclopropanes from the reaction between carbenes and alkenes Download PDF

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Publication number
WO2007144599A3
WO2007144599A3 PCT/GB2007/002175 GB2007002175W WO2007144599A3 WO 2007144599 A3 WO2007144599 A3 WO 2007144599A3 GB 2007002175 W GB2007002175 W GB 2007002175W WO 2007144599 A3 WO2007144599 A3 WO 2007144599A3
Authority
WO
WIPO (PCT)
Prior art keywords
fluorinated
production
cyclopropanes
carbenes
alkenes
Prior art date
Application number
PCT/GB2007/002175
Other languages
French (fr)
Other versions
WO2007144599A2 (en
Inventor
Robert Elliott Low
Andrew Paul Sharratt
Original Assignee
Ineos Fluor Holdings Ltd
Robert Elliott Low
Andrew Paul Sharratt
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.)
Filing date
Publication date
Application filed by Ineos Fluor Holdings Ltd, Robert Elliott Low, Andrew Paul Sharratt filed Critical Ineos Fluor Holdings Ltd
Publication of WO2007144599A2 publication Critical patent/WO2007144599A2/en
Publication of WO2007144599A3 publication Critical patent/WO2007144599A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton

Abstract

The invention relates to processes for the production of fluorinated cyclopropanes In particular, the invention relates to a process for the preparation of fluorinated cyclopropanes for use in compositions, often in heat transfer compositions. On process includes the step of reacting a carbene with a compound of formula (I) where R may be the same or different and is selected from fluorine, alkyl. alkox or hydrogen, wherein if all of the R groups are hydrogen, alkyl or alkoxy, the carbene includes at least one fluorine substituent. A second process includes th step of reacting a compound of formula (II) with a metal and optionally a metal halide to generate a fluorinated cyclopropane, wherein X may be the same or different and is selected from a halogen, alkyl. alkoxy or hydrogen.
PCT/GB2007/002175 2006-06-14 2007-06-12 Production of fluorinated cyclopropanes from the reaction between carbenes and alkenes WO2007144599A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0611741.0 2006-06-14
GB0611741A GB0611741D0 (en) 2006-06-14 2006-06-14 Process

Publications (2)

Publication Number Publication Date
WO2007144599A2 WO2007144599A2 (en) 2007-12-21
WO2007144599A3 true WO2007144599A3 (en) 2008-03-27

Family

ID=36775604

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2007/002175 WO2007144599A2 (en) 2006-06-14 2007-06-12 Production of fluorinated cyclopropanes from the reaction between carbenes and alkenes

Country Status (2)

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GB (1) GB0611741D0 (en)
WO (1) WO2007144599A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2464535A (en) * 2008-09-17 2010-04-28 Ineos Fluor Holdings Ltd Preparation of fluorinated cyclopropanes and fluorinated propenes
US8961811B2 (en) 2010-04-15 2015-02-24 E I Du Pont De Nemours And Company Compositions comprising E-1,2-difluoroethylene and uses thereof
US8961812B2 (en) 2010-04-15 2015-02-24 E I Du Pont De Nemours And Company Compositions comprising Z-1,2-difluoroethylene and uses thereof
WO2014058744A2 (en) 2012-10-09 2014-04-17 California Institute Of Technology In vivo and in vitro olefin cyclopropanation catalyzed by heme enzymes
US20160017110A1 (en) * 2013-03-14 2016-01-21 Honeywell International Inc. Compositions and methods comprising vinylidene fluoride
US9399762B2 (en) 2014-02-18 2016-07-26 California Institute Of Technology Methods and systems for sulfimidation or sulfoximidation of organic molecules
CN112279747B (en) * 2019-07-24 2023-10-27 维思普新材料（苏州）有限公司 Preparation method of pentachlorocyclopropane

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2461523A (en) * 1946-12-04 1949-02-15 Du Pont Dehydrofluorination of polyfluoroalkanes
US2758138A (en) * 1954-05-06 1956-08-07 Du Pont Pyrolysis process for making perfluoropropene from tetrafluoroethylene
US3338978A (en) * 1963-04-24 1967-08-29 Du Pont Method of producing difluorocarbene radicals and of using the same
WO1994002563A1 (en) * 1992-07-15 1994-02-03 E.I. Du Pont De Nemours And Company Refrigerant compositions including 1,1,2,2-tetrafluoroethane
WO2005103187A1 (en) * 2004-04-16 2005-11-03 Honeywell International Inc. Stabilized trifluoroiodmethane compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2461523A (en) * 1946-12-04 1949-02-15 Du Pont Dehydrofluorination of polyfluoroalkanes
US2758138A (en) * 1954-05-06 1956-08-07 Du Pont Pyrolysis process for making perfluoropropene from tetrafluoroethylene
US3338978A (en) * 1963-04-24 1967-08-29 Du Pont Method of producing difluorocarbene radicals and of using the same
WO1994002563A1 (en) * 1992-07-15 1994-02-03 E.I. Du Pont De Nemours And Company Refrigerant compositions including 1,1,2,2-tetrafluoroethane
WO2005103187A1 (en) * 2004-04-16 2005-11-03 Honeywell International Inc. Stabilized trifluoroiodmethane compositions

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
A.A. KAMYSHOVA ET AL.: "Dichlorodimethylcyclopropane.", BULL. ACAD. SCI. USSR DIV. CHEM. SCI., vol. 29, no. 8, 1980, pages 1330 - 1332 *
D.L.S.BRAHMS ET AL.: "Fluorinated carbenes", CHEM. REV., vol. 96, 1996, pages 1585 - 1632, XP002448993 *
D.P. COX ET AL.: "Absolute rate constants for the additions of halophenylcarbenes to alkenes; a reactivity-slectivity relation", TETRAHEDRON LETTERS, vol. 24, no. 48, 1983, pages 5313 - 5316, XP002448992 *
DATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002464574, Database accession no. 1871252 *
HANS MILLAUER ET AL: "Hexafluoropropene Oxide- A Key Compound in Organofluorine Chemistry", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY VCH VERLAG, WEINHEIM, DE, vol. 24, no. 3, March 1985 (1985-03-01), pages 161 - 179, XP009088816, ISSN: 1433-7851 *
HIRAI C ET AL: "Refrigerant compsn not causing destruction of ozone layer - comprises di:fluoromethane, 1,1,12-tetra:fluoroethane, and hexa:fluoro:cyclopropane", WPI / THOMSON, 9 August 1994 (1994-08-09), XP002450578 *
K. CASAS ET AL.: "Fluorinated cyclopropanes. Part III The reactions of methylene with mono-, 1,1-di- and tri-fluoroethylene", J.CHEM.SOC., 1965, pages 1141 - 1148, XP009088892 *
KAMEL M ET AL: "Basisches Verhalten von Epoxiden in Gegenwart von Halogenid-Ionen, IV) gem -Difluorcyclopropane aus Chlordifluormethan und Alkanolat-Ionen in geringer Konzentration Basic Behavior of Epoxides in the Presence of Halide Ions, IV) gem-Difluorocyclopropanes from DMuorocarhe, Generated from Chlorodifluor", CHEMISCHE BERICHTE, VERLAG CHEMIE GMBH. WEINHEIM, DE, vol. 109, 1976, pages 2351 - 2369, XP009088831, ISSN: 0009-2940 *
N.C.CRAIG ET AL.: "Vibrational spectroscopy of perfluorocyclopropene and force constants for fluorine-substituted cyclopropenes", J.PHYS.CHEM., vol. 89, 1985, pages 100 - 105, XP002448991 *
R.N.BEAUCHAMP ET AL.: "The microwave spectra, electric dipole moment and molecular structure of 1,1,2,2-tetrafluorocyclopropane", J.AM.CHEM.SOC., vol. 109, 1987, pages 1696 - 1701, XP002448994 *
W.R.DOLBIER ET AL.: "Structure, synthesis and chemical reactions of fluorinated cyclopropanes and cyclopropenes", CHEM.REV., vol. 103, 2003, pages 1071 - 1098, XP002448995 *

Also Published As

Publication number Publication date
GB0611741D0 (en) 2006-07-26
WO2007144599A2 (en) 2007-12-21

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