Title:
METHOD FOR PRODUCING PERFLUOROALKYNE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2020/204146
Kind Code:
A1
Abstract:
According to the present invention, a perfluorocarbon compound having a double bond or a triple bond is able to be obtained with high yield by:
(1) reacting a halogenated hydrocarbon compound represented by formula (2) (wherein the bond expressed by a solid line and a dotted line represents a single bond or a double bond; in cases where the bond expressed by a solid line and a dotted line is a single bond, each n represents 2, while in cases where the bond expressed by a solid line and a dotted line is a double bond, each n represents 1; R1 and R2 may be the same or different and each represents a fluorine atom or a perfluoroalkyl group; and X1 and X2 may be the same or different and each represents a halogen atom) in an organic solvent in the presence of an iodine-containing inorganic material and zinc or a zinc alloy; or
(2) reacting a halogenated alkene compound represented by X1R1C=CR2X2 (wherein R1, R2, X1 and X2 are as defined above) in a specific nitrogen-containing polar organic solvent in the presence of zinc or a zinc alloy.
Inventors:
ETOU YUUSUKE (JP)
NAKAMURA SHINGO (JP)
NAKAMURA SHINGO (JP)
Application Number:
PCT/JP2020/015239
Publication Date:
October 08, 2020
Filing Date:
April 02, 2020
Export Citation:
Assignee:
DAIKIN IND LTD (JP)
International Classes:
C07B61/00; C07C21/18; C07C17/23; C07C21/22
Domestic Patent References:
| WO2007114359A1 | 2007-10-11 |
Foreign References:
| CN103420783A | 2013-12-04 | |||
| JP2003255540A | 2003-09-10 | |||
| JP2012000842A | 2012-01-05 | |||
| JPH0285222A | 1990-03-26 | |||
| CN106008147A | 2016-10-12 | |||
| JP2013530143A | 2013-07-25 | |||
| JP2012513405A | 2012-06-14 |
Other References:
ZHANG CHENGPING; JIA XIAOQING; QUAN HENGDAO: "Synthesis of Z-1, 1, 1, 4, 4, 4- hexafluoro-2-butene from haxachlorobutadiene", JOURNAL OF FLUORINE CHEMISTRY, vol. 191, 2016, pages 77 - 83, XP029801766
SUN, X. ET AL.: "Study on the technology of preparing hexafluoro-2-butyne", ORGANO-FLUORINE INDUSTRY, vol. 2, 2012, pages 14 - 17
BLANCOU, H. ET AL.: "Reactivite des perfluorohalogenoalcanes en presence de couples metalliciues-II. Formation de perfluoroolefines a partir des perfluoroiodoalcanes dans les solvants aprotiques dissociants. (DMSO, DMF, HMPT", TETRAHEDRON, vol. 33, 1976, pages 2061 - 2067, XP002937474
CHEN, QINGYUN ET AL.: "Studies on Fluoroalkylation and Fluoroalkoxylation 18. Reactions of 2- halotetrafluoroethyl Iodide with Nitrogen Containing Nucleophiles", CHINESE JOURNAL OF ORGANIC CHEMISTRY, 1987, pages 364 - 369
BHADURY, P. S. ET AL.: "Fluorine chemistry-Vlittig based synthesis of volatile organofluorine compounds", CAN. J. CHEM., vol. 82, 2004, pages 1186 - 1191
HENNE, A. L. ET AL.: "Perfluoro-2-butyne and its Hydrogenation Products", J. AM. CHEM. SOC., vol. 71, 1949, pages 298 - 300, XP002512760
SUN, X. ET AL.: "Study on the technology of preparing hexafluoro-2-butyne", ORGANO-FLUORINE INDUSTRY, vol. 2, 2012, pages 14 - 17
BLANCOU, H. ET AL.: "Reactivite des perfluorohalogenoalcanes en presence de couples metalliciues-II. Formation de perfluoroolefines a partir des perfluoroiodoalcanes dans les solvants aprotiques dissociants. (DMSO, DMF, HMPT", TETRAHEDRON, vol. 33, 1976, pages 2061 - 2067, XP002937474
CHEN, QINGYUN ET AL.: "Studies on Fluoroalkylation and Fluoroalkoxylation 18. Reactions of 2- halotetrafluoroethyl Iodide with Nitrogen Containing Nucleophiles", CHINESE JOURNAL OF ORGANIC CHEMISTRY, 1987, pages 364 - 369
BHADURY, P. S. ET AL.: "Fluorine chemistry-Vlittig based synthesis of volatile organofluorine compounds", CAN. J. CHEM., vol. 82, 2004, pages 1186 - 1191
HENNE, A. L. ET AL.: "Perfluoro-2-butyne and its Hydrogenation Products", J. AM. CHEM. SOC., vol. 71, 1949, pages 298 - 300, XP002512760
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
Download PDF: