Title:
METHOD FOR PURIFYING PHOSPHORUS-CONTAINING OLEFIN COMPOUND SALT AND METHOD FOR PRODUCING OLEFIN COMPOUND USING PURIFIED PRODUCT OBTAINED THEREBY
Document Type and Number:
WIPO Patent Application WO/2021/025012
Kind Code:
A1
Abstract:
Provided are: a method for purifying a phosphorus-containing olefin compound salt of a raw material or intermediate that can be applied to a method for producing an olefin compound, the purification method being useful for raising the purity of a target substance in the production method; and a method for producing an olefin compound using the purified product obtained thereby. Specifically, provided is a method for purifying a phosphorus-containing olefin compound salt, the method having a step for obtaining a purified product of the phosphorus-containing olefin compound salt by re-precipitating and/or re-crystallizing, in a solvent, a solid that contains at least one phosphorus-containing olefin compound salt selected from the group consisting of phosphorus-containing olefin compound salts A represented by general formula (1) [in the formula, X1 and X2 independently represent F, Cl Br, I, or H; W+ are the same or different monovalent cations comprising PR3 or POR3 (where R are groups having a saturated or unsaturated structure including C and H, and R may bond to each other to form a ring and may include atoms other than C and H); the three R included in the R3 may be the same or different; M- represents a monovalent anion comprising an atom or a compound] and phosphorus-containing olefin compound salts B represented by general formula (2) [in the formula, X1, X2, W+, and M- are the same as above; Y represents F, Cl, Br, I, H, an alkyl group, an alkyl ether group, a fluoroalkyl group, or a fluoroalkyl ether group].
Inventors:
ITO YUUKO (JP)
NAKAUE TSUBASA (JP)
CHAKI TAKEHIRO (JP)
USUI TAKASHI (JP)
IWAMOTO TOMOYUKI (JP)
KUSHIDA MEGUMI (JP)
NAKAUE TSUBASA (JP)
CHAKI TAKEHIRO (JP)
USUI TAKASHI (JP)
IWAMOTO TOMOYUKI (JP)
KUSHIDA MEGUMI (JP)
Application Number:
PCT/JP2020/029796
Publication Date:
February 11, 2021
Filing Date:
August 04, 2020
Export Citation:
Assignee:
DAIKIN IND LTD (JP)
International Classes:
C07C21/18; C07C17/35; C07F9/52
Foreign References:
| US3320321A | 1967-05-16 |
Other References:
OVAKIMYAN M. ZH.; GASPARYAN G. A.; BICHAKHCHYAN А. S.; BAGRATYAN R. R.; DERDZYAN L. V.; TAMAZYAN R. А.; HAIVAZYAN А. G.: "Halogenation of quaternary phosphonium salts containing prop-1(2)-enyl group", RUSSIAN JOURNAL OF GENERAL CHEMISTRY., M A I K NAUKA - INTERPERIODICA, RU, vol. 87, no. 8, 16 September 2017 (2017-09-16), RU, pages 1727 - 1730, XP036321666, ISSN: 1070-3632, DOI: 10.1134/S1070363217080151
MAIER L, SEYFERTH D, STONE F G A, ROCHOW E G: "Vinyl derivatives of the metals. VI. Preparation, properties, and some reactions of trivinyl compounds of group V elements", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 79, 1 January 1957 (1957-01-01), pages 5884 - 5889, XP055791893
RABINOWITZ ROBERT, HENRY ARTHUR C., MARCUS RUTH: "Synthesis of vinylphosphonium compounds", JOURNAL OF POLYMER SCIENCE, PART A: GENERAL PAPERS, vol. 3, no. 5, 1 May 1965 (1965-05-01), pages 2055 - 2061, XP055791883, ISSN: 0449-2951, DOI: 10.1002/pol.1965.100030534
FROHN, H.-J. BARDIN, V.V.: "The unusual reactivity of C"3F"7OCF@?CF"2 with PBu"3 and the complex hydrides M[EH"4] (M: Li, Na; E: B, Al); preparation of potassium perfluoro-2-propoxyeth-1-enyltrifluoroborate K[C"3F"7OCF@?CFBF"3]", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 123, no. 1, 1 September 2003 (2003-09-01), NL, pages 43 - 49, XP004456417, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(03)00107-6
BURTON D. J., SPAWN T. D., HEINZE P. L., BAILEY A. R., SHIN-YA S.: "PREPARATION OF E-1,2,3,3,3-PENTAFLUOROPROPENE, Z-1,2,3,3,3-PENTAFLUOROPROPENE AND E-1-IODOPENTAFLUOROPROPENE.", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 44., no. 01., 1 July 1989 (1989-07-01), NL, pages 167 - 174., XP000008378, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(00)84380-8
FROHN, H.-J. FRANKE, H. FRITZEN, P. BARDIN, V.V.: "(Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 598, no. 1, 1 March 2000 (2000-03-01), AMSTERDAM, NL, pages 127 - 135, XP004191191, ISSN: 0022-328X, DOI: 10.1016/S0022-328X(99)00690-7
WANG SHI-MENG, JIA-BIN HAN, CHENG-PAN ZHANG, HUA-LI QIN: "A solvent-free facile synthesis of (E)-bis(phosphonium)ethylenes from organo- phosphines and TfOCH2CF2H reagent", TETRAHEDRON LETTERS, vol. 56, no. 45, pages 6219 - 6222, XP055791879
E. VEDEJS, S. T. DIVER: "Tributylphosphine: a remarkable acylation catalyst", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 115, no. 8, 1 April 1993 (1993-04-01), US, pages 3358 - 3359, XP055240422, ISSN: 0002-7863, DOI: 10.1021/ja00061a056
MONKOWIUS UWE, NOGAI STEFAN, SCHMIDBAUR HUBERT: "Contributions to the Little Known Chemistry of Trivinylphosphine and Trivinylarsine", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 22, no. 1, 1 January 2003 (2003-01-01), pages 145 - 152, XP055791874, ISSN: 0276-7333, DOI: 10.1021/om020653j
JOURNAL OF FLUORINE CHEMISTRY, vol. 123, 2003, pages 43 - 49
See also references of EP 4011856A4
MAIER L, SEYFERTH D, STONE F G A, ROCHOW E G: "Vinyl derivatives of the metals. VI. Preparation, properties, and some reactions of trivinyl compounds of group V elements", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 79, 1 January 1957 (1957-01-01), pages 5884 - 5889, XP055791893
RABINOWITZ ROBERT, HENRY ARTHUR C., MARCUS RUTH: "Synthesis of vinylphosphonium compounds", JOURNAL OF POLYMER SCIENCE, PART A: GENERAL PAPERS, vol. 3, no. 5, 1 May 1965 (1965-05-01), pages 2055 - 2061, XP055791883, ISSN: 0449-2951, DOI: 10.1002/pol.1965.100030534
FROHN, H.-J. BARDIN, V.V.: "The unusual reactivity of C"3F"7OCF@?CF"2 with PBu"3 and the complex hydrides M[EH"4] (M: Li, Na; E: B, Al); preparation of potassium perfluoro-2-propoxyeth-1-enyltrifluoroborate K[C"3F"7OCF@?CFBF"3]", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 123, no. 1, 1 September 2003 (2003-09-01), NL, pages 43 - 49, XP004456417, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(03)00107-6
BURTON D. J., SPAWN T. D., HEINZE P. L., BAILEY A. R., SHIN-YA S.: "PREPARATION OF E-1,2,3,3,3-PENTAFLUOROPROPENE, Z-1,2,3,3,3-PENTAFLUOROPROPENE AND E-1-IODOPENTAFLUOROPROPENE.", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 44., no. 01., 1 July 1989 (1989-07-01), NL, pages 167 - 174., XP000008378, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(00)84380-8
FROHN, H.-J. FRANKE, H. FRITZEN, P. BARDIN, V.V.: "(Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 598, no. 1, 1 March 2000 (2000-03-01), AMSTERDAM, NL, pages 127 - 135, XP004191191, ISSN: 0022-328X, DOI: 10.1016/S0022-328X(99)00690-7
WANG SHI-MENG, JIA-BIN HAN, CHENG-PAN ZHANG, HUA-LI QIN: "A solvent-free facile synthesis of (E)-bis(phosphonium)ethylenes from organo- phosphines and TfOCH2CF2H reagent", TETRAHEDRON LETTERS, vol. 56, no. 45, pages 6219 - 6222, XP055791879
E. VEDEJS, S. T. DIVER: "Tributylphosphine: a remarkable acylation catalyst", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, US, vol. 115, no. 8, 1 April 1993 (1993-04-01), US, pages 3358 - 3359, XP055240422, ISSN: 0002-7863, DOI: 10.1021/ja00061a056
MONKOWIUS UWE, NOGAI STEFAN, SCHMIDBAUR HUBERT: "Contributions to the Little Known Chemistry of Trivinylphosphine and Trivinylarsine", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 22, no. 1, 1 January 2003 (2003-01-01), pages 145 - 152, XP055791874, ISSN: 0276-7333, DOI: 10.1021/om020653j
JOURNAL OF FLUORINE CHEMISTRY, vol. 123, 2003, pages 43 - 49
See also references of EP 4011856A4
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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