WO2009147917A1 - 含酸素ハロゲン化フッ化物の製造方法 - Google Patents
含酸素ハロゲン化フッ化物の製造方法 Download PDFInfo
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- WO2009147917A1 WO2009147917A1 PCT/JP2009/058357 JP2009058357W WO2009147917A1 WO 2009147917 A1 WO2009147917 A1 WO 2009147917A1 JP 2009058357 W JP2009058357 W JP 2009058357W WO 2009147917 A1 WO2009147917 A1 WO 2009147917A1
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- gas
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B11/00—Oxides or oxyacids of halogens; Salts thereof
- C01B11/24—Oxygen compounds of fluorine
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/24—Inter-halogen compounds
Definitions
- the present invention relates to a method for producing an oxygen-containing halogenated fluoride.
- Oxygenated halogenated fluorides are used as monofluoromethylating agents in the production of 1-fluoro-1,1-bis (arylsulfonyl) methane, which is a physiologically active substance useful as a pharmaceutical (Patent Document 1). .
- methods for producing oxygen-containing halogenated fluorides include, for example, a reaction between Cl 2 O and ClF (for example, Non-Patent Document 1), and a reaction between ClF 5 and CsNO 3 (for example, Non-Patent Document 2).
- a method for producing ClO 2 F by the method is known.
- the method for producing these oxygen-containing halogenated fluorides is mainly a solid-gas reaction or a reaction using an explosive compound. Since the F 2 gas and fluoride gas used for the solid-gas reaction are very active substances, the temperature rises as the reaction proceeds. And if this temperature rise progresses, the generation
- the present invention has been made to solve the above-described problems, and an object of the present invention is to provide a method for producing an oxygen-containing halogenated fluoride efficiently and continuously.
- a method for producing an oxygen-containing halogenated fluoride represented by the general formula: XO 2 F by reacting a halogen fluoride represented by the general formula: XF with an H 2 O source.
- X represents a halogen element of Cl, Br, or I.
- FIG. 1 is a schematic system diagram showing an apparatus for producing an oxygen-containing halogenated fluoride according to an embodiment of the present invention.
- an oxygen-containing halogenated fluoride XO 2 F represented by the general formula: XO 2 F is produced by reacting a halogen fluoride represented by the general formula: XF with an H 2 O source.
- X represents a halogen element of Cl, Br, or I.
- gaseous halogen fluoride XF, ClF 3 , IF 3 , IF 7 , IF 5 , ClF, BrF, BrF 3 , BrF 5 and the like can be used.
- the use temperature of the liquid raw material is not particularly limited.
- countercurrent contact As a contact method for causing gas-liquid reaction between the gas raw material and the liquid raw material, countercurrent contact or cocurrent contact can be used. Among them, countercurrent contact is more preferable in view of gas-liquid contact efficiency. Furthermore, the reaction temperature when the gas source and the liquid source are subjected to a gas-liquid reaction is not a problem as long as the liquid source can be brought into contact with the gas source in a liquid state.
- the apparatus for producing oxygen-containing halogenated fluoride XO 2 F of the present invention has a reaction tank for contacting a gas raw material and a liquid raw material, and can supply the gas raw material and the liquid raw material to the reaction tank. Any structure that can extract gas is acceptable.
- the reaction tank may have a mechanism for circulating the liquid raw material.
- the material of the reaction tank only needs to have sufficient resistance to the gas raw material and the liquid raw material, and stainless steel, Ni steel, steel, Monel, Inconel, aluminum and the like are preferable.
- FIG. 1 shows a schematic system diagram of a manufacturing apparatus according to an embodiment of the present invention.
- the production apparatus includes a dilution gas cylinder 1, a raw material gas cylinder 2, mass flow controllers (MFC) 3 and 4, a reaction tank 5, and an empty container 9.
- MFC mass flow controllers
- the dilution gas cylinder 1 and the source gas cylinder 2 store a dilution gas (for example, N 2 ) and a source gas (for example, ClF 3 ), and their flow rates are controlled by the MFCs 3 and 4 so that a predetermined gas composition is obtained. And introduced into the reaction vessel 5.
- a dilution gas for example, N 2
- a source gas for example, ClF 3
- the reaction tank 5 includes a packed column 7 filled with a filler, a liquid tank 10 having a capacity sufficient to store a raw material liquid 8 and an inner wall lined with polytetrafluoroethylene, and a raw material liquid in the liquid tank 10. And a liquid feed pump 6 for feeding 8 above the filler.
- a liquid feed pump 6 for feeding 8 above the filler.
- the gas released from the reaction vessel 5 is collected in the empty container 9.
- the gas collected in the empty container 9 is analyzed by a Fourier transform infrared spectrophotometer (FT-IR) or the like, and the concentration of the produced oxygen-containing halogenated fluoride XO 2 F (for example, ClO 2 F) is measured. To do.
- FT-IR Fourier transform infrared spectrophotometer
- the present invention uses a gas-liquid reaction between a halogen fluoride and a H 2 O source, so that the temperature can be easily controlled as compared with a conventional solid-gas reaction or a reaction using an explosive compound.
- the target oxygen-containing halogenated fluoride XO 2 F can be produced efficiently and continuously.
- the oxygen-containing halogenated fluoride XO 2 F obtained in the present invention can be used, for example, as a selective fluorinating agent for fluorination of the ⁇ -position of an ester.
- a 4 ⁇ PTFE polytetrafluoroethylene
- a packed tower 7 in which an inner wall of a SUS316 tube having a length of 650 mm and an inner diameter of 25 mm is lined with polytetrafluoroethylene having a thickness of 0.1 mm.
- (Ethylene) Raschig rings were used.
- N 2 2 vol%: mixed so that 98 vol% did.
- the prepared mixed gas was introduced into the reaction vessel 5 at a reaction temperature of 24 ° C. at a 0.274 l / min (superficial linear velocity of 9.31 ⁇ 10 ⁇ 3 m / sec). Thereafter, the gas released from the reaction vessel 5 was collected in an empty container 9.
- the ClO 2 F concentration in the gas collected in the empty container 9 was analyzed by FT-IR (IG-1000 manufactured by Otsuka Electronics Co., Ltd.). As a result, the ClO 2 F concentration was 3872 ppm, and it was confirmed that ClO 2 F was generated. The yield based on Cl was 19.36%.
- a mixed gas whose mixed gas composition is adjusted to ClF 3 : N 2 2 vol%: 98 vol% with MFC 3 and 4 is introduced at 1.096 l / min (superficial linear velocity 3.72 ⁇ 10 ⁇ 2 m / sec). Except for this, a gas-liquid reaction was attempted under the same conditions as in Example 1. Similarly to Example 1, the ClO 2 F concentration in the gas collected after passing through the reaction vessel 5 was analyzed by FT-IR (IG-1000 manufactured by Otsuka Electronics Co., Ltd.).
- a gas-liquid reaction was tried under the same conditions as in Example 1 except that the introduction was performed in Similarly to Example 1, the ClO 2 F concentration in the gas collected after passing through the reaction vessel 5 was analyzed by FT-IR (IG-1000 manufactured by Otsuka Electronics Co., Ltd.).
- a gas-liquid reaction was attempted under the same conditions as in Example 1 except that the reaction temperature was 40 ° C. using the mixed gas.
- the ClO 2 F concentration in the gas collected after passing through the reaction vessel 5 was analyzed by FT-IR (IG-1000 manufactured by Otsuka Electronics Co., Ltd.).
- the ClO 2 F concentration in the gas collected after passing through the reaction vessel 5 was analyzed by FT-IR (IG-1000 manufactured by Otsuka Electronics Co., Ltd.).
- a gas-liquid reaction was tried under the same conditions as in Example 1 except for using.
- the ClO 2 F concentration in the gas collected after passing through the reaction vessel 5 was analyzed by FT-IR (IG-1000 manufactured by Otsuka Electronics Co., Ltd.).
- the ClO 2 F concentration in the gas collected after passing through the reaction vessel 5 was analyzed by FT-IR (IG-1000 manufactured by Otsuka Electronics Co., Ltd.).
- ClO 2 F could be produced in good yield by gas-liquid reaction between ClF 3 and H 2 O source (water or aqueous solution).
- H 2 O source water or aqueous solution.
- temperature control is easier than conventional solid-gas reactions and reactions using explosive compounds.
- the target oxygen-containing halogenated fluoride XO 2 F can be produced efficiently and continuously by the gas-liquid reaction between the halogen fluoride and the H 2 O source.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (2)
- 一般式:XFで表されるフッ化ハロゲンとH2O源を反応させることにより、一般式:XO2Fで表される含酸素ハロゲン化フッ化物の製造方法。但し、XはCl、Br、Iのいずれかのハロゲン元素を表す。
- 前記フッ化ハロゲンは、ClF、ClF3、IF3、IF7、IF5、BrF、BrF3、BrF5のいずれかであり、前記H2O源は水またはpH=1~13の水溶液であることを特徴とする、請求項1に記載の製造方法。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/991,382 US20110150747A1 (en) | 2008-06-02 | 2009-04-28 | Method for Manufacturing Oxygen-Containing Halogenated Fluoride |
EP09758184.7A EP2292556B1 (en) | 2008-06-02 | 2009-04-28 | Method for manufacturing oxygen-containing halogenated fluoride |
CN200980120420.0A CN102046521B (zh) | 2008-06-02 | 2009-04-28 | 含氧卤代氟化物的制造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008-144616 | 2008-06-02 | ||
JP2008144616A JP5439748B2 (ja) | 2008-06-02 | 2008-06-02 | 含酸素ハロゲン化フッ化物の製造方法 |
Publications (1)
Publication Number | Publication Date |
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WO2009147917A1 true WO2009147917A1 (ja) | 2009-12-10 |
Family
ID=41397995
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2009/058357 WO2009147917A1 (ja) | 2008-06-02 | 2009-04-28 | 含酸素ハロゲン化フッ化物の製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20110150747A1 (ja) |
EP (1) | EP2292556B1 (ja) |
JP (1) | JP5439748B2 (ja) |
KR (1) | KR20110016930A (ja) |
CN (1) | CN102046521B (ja) |
WO (1) | WO2009147917A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP6246449B1 (ja) * | 2016-04-05 | 2017-12-13 | 関東電化工業株式会社 | フッ化塩素の供給方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3545924A (en) * | 1965-10-21 | 1970-12-08 | Olin Mathieson | Method of preparing chloryl fluoride |
US3718557A (en) * | 1967-12-06 | 1973-02-27 | North American Rockwell | PROCESS OF MAKING ClF{11 O |
US3733392A (en) * | 1966-04-13 | 1973-05-15 | American Rockwell Corp N | Oxychlorine trifluoride and alkali fluoride-cl2o complex |
JP2007230961A (ja) | 2006-03-03 | 2007-09-13 | Nagoya Institute Of Technology | 1−フルオロ−1,1−ビス(フェニルスルホニル)メタンおよびその製造法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1497123A (fr) * | 1965-10-21 | 1967-10-06 | Olin Mathieson | Procédé de fabrication de fluorure de chloryle |
FR1527112A (fr) * | 1967-04-18 | 1968-05-31 | Commissariat Energie Atomique | Procédé de préparation du fluorure de chloryle |
US4402868A (en) * | 1980-12-08 | 1983-09-06 | Texaco Inc. | Catalyst for the production of methane-rich gas |
CA1273647A (en) * | 1987-08-19 | 1990-09-04 | Jean V. Sang | Production of ceramic powders by emulsion precipitation processes and the products thereof |
CA2203384C (en) * | 1994-10-22 | 2001-01-09 | Teruo Umemoto | Conjugated n-fluoropyridinium salt-containing polymer and use of the same |
JP5163190B2 (ja) * | 2008-03-10 | 2013-03-13 | セントラル硝子株式会社 | 含酸素ハロゲン化フッ化物の製造方法 |
-
2008
- 2008-06-02 JP JP2008144616A patent/JP5439748B2/ja not_active Expired - Fee Related
-
2009
- 2009-04-28 CN CN200980120420.0A patent/CN102046521B/zh not_active Expired - Fee Related
- 2009-04-28 KR KR1020107027783A patent/KR20110016930A/ko not_active Application Discontinuation
- 2009-04-28 US US12/991,382 patent/US20110150747A1/en not_active Abandoned
- 2009-04-28 WO PCT/JP2009/058357 patent/WO2009147917A1/ja active Application Filing
- 2009-04-28 EP EP09758184.7A patent/EP2292556B1/en not_active Not-in-force
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3545924A (en) * | 1965-10-21 | 1970-12-08 | Olin Mathieson | Method of preparing chloryl fluoride |
US3733392A (en) * | 1966-04-13 | 1973-05-15 | American Rockwell Corp N | Oxychlorine trifluoride and alkali fluoride-cl2o complex |
US3718557A (en) * | 1967-12-06 | 1973-02-27 | North American Rockwell | PROCESS OF MAKING ClF{11 O |
JP2007230961A (ja) | 2006-03-03 | 2007-09-13 | Nagoya Institute Of Technology | 1−フルオロ−1,1−ビス(フェニルスルホニル)メタンおよびその製造法 |
Non-Patent Citations (2)
Title |
---|
INORGANIC CHEMISTRY, vol. 28, 1989, pages 675 |
JOURNAL OF THE CHEMICAL SOCIETY, 1954, pages 4113 - 4116 |
Also Published As
Publication number | Publication date |
---|---|
EP2292556A4 (en) | 2012-06-27 |
US20110150747A1 (en) | 2011-06-23 |
JP2009292655A (ja) | 2009-12-17 |
EP2292556A1 (en) | 2011-03-09 |
JP5439748B2 (ja) | 2014-03-12 |
KR20110016930A (ko) | 2011-02-18 |
CN102046521A (zh) | 2011-05-04 |
CN102046521B (zh) | 2013-06-12 |
EP2292556B1 (en) | 2013-07-10 |
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