JPH11116216A - Production of carbonyl fluoride - Google Patents
Production of carbonyl fluorideInfo
- Publication number
- JPH11116216A JPH11116216A JP9272831A JP27283197A JPH11116216A JP H11116216 A JPH11116216 A JP H11116216A JP 9272831 A JP9272831 A JP 9272831A JP 27283197 A JP27283197 A JP 27283197A JP H11116216 A JPH11116216 A JP H11116216A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- reaction
- carbon dioxide
- carbonyl fluoride
- vessel
- Prior art date
- 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.)
- Granted
Links
Landscapes
- Carbon And Carbon Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、有機合成の試薬等
に有用なフッ化カルボニルの新規な製造法に関するもの
である。TECHNICAL FIELD The present invention relates to a novel method for producing carbonyl fluoride useful as a reagent for organic synthesis and the like.
【０００２】[0002]
【従来の技術および発明が解決しようとする課題】フッ
化カルボニルの合成法は、一般に、塩化カルボニルいわ
ゆるホスゲンをフッ化水素、三フッ化アンチモン、三フ
ッ化砒素、フッ化ナトリウム等の適当なフッ素化剤と反
応させ、分子中の塩素原子を対応するフッ素原子にハロ
ゲン置換する方法、および一酸化炭素をフッ素、二フッ
化銀等の適当なフッ素化剤と反応させて酸化する方法の
２つに大別される。例えば、特開昭５４−１５８３９６
号公報には、ホスゲンをアセトニトリルの存在下でフッ
化水素と反応させることでフッ化カルボニルを製造する
方法が開示されている。また、Ｉｎｏｒｇ．Ｓｙｎｔ
ｈ．，６，１５５（１９６０）には、一酸化炭素を二フ
ッ化銀と反応させることでフッ化カルボニルを合成する
方法が記載されている。フッ化カルボニルのその他の合
成法として、フッ化エタンをオゾンと反応させる方法
が、Ｊ．Ａｍｅｒ．Ｃｈｅｍ．Ｓｏｃ．，１０２，７５
７２（１９８０）に、また、一酸化炭素と四フッ化炭素
の平衡反応を用いた方法が、Ｊ．Ａｍｅｒ．Ｃｈｅｍ．
Ｓｏｃ．，６２，３４７９（１９４０）にそれぞれ記載
されている。2. Description of the Related Art In general, carbonyl fluoride is synthesized by converting carbonyl chloride, so-called phosgene, into an appropriate fluorine such as hydrogen fluoride, antimony trifluoride, arsenic trifluoride or sodium fluoride. Reacting with a fluorinating agent and halogen-substituting a chlorine atom in the molecule with a corresponding fluorine atom, and oxidizing by reacting carbon monoxide with a suitable fluorinating agent such as fluorine or silver difluoride. Are roughly divided into For example, JP-A-54-158396
The publication discloses a method for producing carbonyl fluoride by reacting phosgene with hydrogen fluoride in the presence of acetonitrile. Inorg. Synt
h. , 6 , 155 (1960) describe a method for synthesizing carbonyl fluoride by reacting carbon monoxide with silver difluoride. As another method for synthesizing carbonyl fluoride, a method of reacting ethane fluoride with ozone is described in J. Am. Amer. Chem. Soc. , 102,75
72 (1980), a method using an equilibrium reaction between carbon monoxide and carbon tetrafluoride is described in J. Am. Amer. Chem.
Soc. , 62, 3479 (1940).
【０００３】このような従来のフッ化カルボニルの製造
法においては、原料として毒性の強いホスゲンや一酸化
炭素を用いる必要があり、安全性に欠ける等の問題があ
った。In such a conventional method for producing carbonyl fluoride, it is necessary to use highly toxic phosgene or carbon monoxide as a raw material, and there is a problem of lack of safety.
【０００４】[0004]
【課題を解決するための具体的手段】本発明者らは、か
かる問題点に鑑み鋭意検討した結果、フッ化カルボニル
を製造するにあたり、毒性の強いホスゲンや一酸化炭素
を用いないで、安価に製造する方法を見出し本発明に到
達した。The inventors of the present invention have conducted intensive studies in view of the above problems, and have found that carbonyl fluoride can be produced at low cost without using highly toxic phosgene or carbon monoxide. A method of manufacturing has been found and the present invention has been reached.
【０００５】すなわち、本発明は、二酸化炭素とフッ素
を気体状で反応させることを特徴とするフッ化カルボニ
ルの製造方法である。本発明によると、原料にホスゲン
より毒性の低い二酸化炭素を用いるため製造時の安全性
が高まる。また、二酸化炭素は工業的に広く用いられて
いるため、入手も容易で安価である。That is, the present invention is a method for producing carbonyl fluoride, which comprises reacting carbon dioxide and fluorine in a gaseous state. According to the present invention, since carbon dioxide having lower toxicity than phosgene is used as a raw material, safety during production is improved. Moreover, since carbon dioxide is widely used industrially, it is easily available and inexpensive.
【０００６】本発明において、二酸化炭素とフッ素との
反応方法は、バッチ式あるいは流通式のいずれを用いて
も良い。また、反応温度は、５０℃〜４００℃の範囲で
適宜選択すれば良いが、好ましくは１５０℃〜２５０℃
の範囲が最適である。反応温度が低すぎる場合には、二
酸化炭素とフッ素の反応が起こりにくくなるため反応率
の低下を引き起こし、また、反応温度が高すぎる場合に
は、副生する四フッ化炭素が多くなるため収率が低下し
好ましくない。In the present invention, the reaction method between carbon dioxide and fluorine may be either a batch type or a flow type. The reaction temperature may be appropriately selected in the range of 50 ° C to 400 ° C, preferably 150 ° C to 250 ° C.
Is optimal. If the reaction temperature is too low, the reaction between carbon dioxide and fluorine is unlikely to occur, causing a decrease in the reaction rate. The rate decreases, which is not preferable.
【０００７】また、二酸化炭素とフッ素のモル比の割合
（二酸化炭素／フッ素）は、０．１〜１０の範囲で適宜
選択すれば良く、好ましくは０．５〜２の範囲が最適で
ある。モル比の割合が低い場合、すなわちフッ素が過剰
となる場合には、四フッ化炭素の副生が多くなり、逆に
モル比の割合が高い場合にはフッ素の分圧が下がるため
活性が低くなり反応が起こりにくくなる。次に、反応圧
力は、反応温度、混合比に合わせて適宜選択すれば良い
が、通常は取り扱いが容易な大気圧付近を選択するのが
好ましい。The molar ratio of carbon dioxide to fluorine (carbon dioxide / fluorine) may be appropriately selected within the range of 0.1 to 10, and is most preferably in the range of 0.5 to 2. When the molar ratio is low, that is, when the amount of fluorine is excessive, the amount of by-product carbon tetrafluoride increases. Reaction becomes difficult to occur. Next, the reaction pressure may be appropriately selected in accordance with the reaction temperature and the mixing ratio, but it is usually preferable to select around the atmospheric pressure where handling is easy.
【０００８】本発明において使用する装置材質は、ニッ
ケル、ニッケル合金、ステンレス、銅、真鍮、アルミニ
ウム、アルミニウム合金、スチール等の耐フッ素金属
や、石英、アルミナ、炭化珪素、窒化アルミニウム等の
耐フッ素セラミックス等を用いる。フッ素によって侵さ
れる金属、セラミックス、高分子材料や、タングステ
ン、モリブデン等のフッ素と反応してガス化するような
材質は好ましくない。また、使用する反応装置及び製造
したフッ化カルボニルを保存する容器等は、水分を完全
に除いたものを使用することが好ましい。水分が混入し
た系にフッ化カルボニルを曝すとフッ化カルボニルは速
やかに加水分解を起こし、フッ化水素と二酸化炭素を生
成して純度低下を引き起こす。The material of the apparatus used in the present invention is a fluorine-resistant metal such as nickel, nickel alloy, stainless steel, copper, brass, aluminum, aluminum alloy, steel, or a fluorine-resistant ceramic such as quartz, alumina, silicon carbide, or aluminum nitride. And so on. Metals, ceramics, polymer materials, and materials that react with fluorine and gasify such as tungsten and molybdenum are not preferable. Further, it is preferable to use a reactor in which water is completely removed as a reaction apparatus and a container for storing the produced carbonyl fluoride. When carbonyl fluoride is exposed to a system in which water is mixed, carbonyl fluoride is rapidly hydrolyzed to generate hydrogen fluoride and carbon dioxide, resulting in a decrease in purity.
【０００９】[0009]
【実施例】以下、本発明を実施例により詳細に説明する
が、本発明はかかる実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.
【００１０】実施例１〜５ 内面研磨されたＳＵＳ３１６製の反応装置を用い反応を
行った。反応容器に二酸化炭素、フッ素を所定のモル比
（ＣＯ2／Ｆ2）で導入した後、反応温度を所定の温度に
保持した。反応は、反応器内の圧力の経時変化でモニタ
ーし、平衡圧力となったところを反応終点とした。反応
終了後、赤外分光法及びガスクロマトグラフィーにて分
析した。これらの反応の条件とその結果を表１に示す。Examples 1 to 5 Reaction was carried out using a SUS316 reaction device whose inner surface was polished. After introducing carbon dioxide and fluorine into the reaction vessel at a predetermined molar ratio (CO 2 / F 2 ), the reaction temperature was maintained at a predetermined temperature. The reaction was monitored by the time-dependent change in the pressure in the reactor, and the point at which the pressure reached an equilibrium pressure was defined as the reaction end point. After completion of the reaction, analysis was performed by infrared spectroscopy and gas chromatography. Table 1 shows the conditions of these reactions and the results.
【００１１】[0011]
【表１】 [Table 1]
【００１２】[0012]
【発明の効果】本発明の方法により、毒性が低く、安価
な二酸化炭素を用いて有機合成試薬等に有用なフッ化カ
ルボニルを安全に製造できる。Industrial Applicability According to the method of the present invention, carbonyl fluoride useful as an organic synthesis reagent or the like can be safely produced using inexpensive carbon dioxide with low toxicity.
Claims (1)
ることを特徴とするフッ化カルボニルの製造方法。1. A method for producing carbonyl fluoride, comprising reacting carbon dioxide and fluorine in a gaseous state.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27283197A JP3707917B2 (en) | 1997-10-06 | 1997-10-06 | Method for producing carbonyl fluoride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27283197A JP3707917B2 (en) | 1997-10-06 | 1997-10-06 | Method for producing carbonyl fluoride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11116216A true JPH11116216A (en) | 1999-04-27 |
| JP3707917B2 JP3707917B2 (en) | 2005-10-19 |
Family
ID=17519386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27283197A Expired - Fee Related JP3707917B2 (en) | 1997-10-06 | 1997-10-06 | Method for producing carbonyl fluoride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3707917B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002098792A1 (en) * | 2001-06-05 | 2002-12-12 | Daikin Industries, Ltd. | Method of separating acid |
| WO2004080894A1 (en) * | 2003-03-14 | 2004-09-23 | Research Institute Of Innovative Technology For The Earth | Process for producing carbonyl fluoride |
| WO2004092067A1 (en) * | 2003-02-17 | 2004-10-28 | Daikin Industries, Ltd. | Method for producing carbonyl difluoride |
| KR100490771B1 (en) * | 2001-11-16 | 2005-05-19 | 샌트랄 글래스 컴퍼니 리미티드 | Process for producing carbonyl difluoride |
| JP2005206583A (en) * | 2003-12-25 | 2005-08-04 | Sumitomo Chemical Co Ltd | Method for producing fluoride ion-containing alkyl-substituted imidazolium salt |
| EP1698592A1 (en) * | 2003-12-11 | 2006-09-06 | Asahi Glass Company Ltd. | Method and apparatus for producing carbonyl fluoride |
| JP4851463B2 (en) * | 2005-09-27 | 2012-01-11 | 独立行政法人産業技術総合研究所 | Method for producing carbonyl fluoride |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010041601A1 (en) | 2008-10-06 | 2010-04-15 | 昭和電工株式会社 | Process for producing carbonyl difluoride |
-
1997
- 1997-10-06 JP JP27283197A patent/JP3707917B2/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002098792A1 (en) * | 2001-06-05 | 2002-12-12 | Daikin Industries, Ltd. | Method of separating acid |
| US7423174B2 (en) | 2001-06-05 | 2008-09-09 | Daikin Industries, Ltd. | Method of separating acid |
| KR100490771B1 (en) * | 2001-11-16 | 2005-05-19 | 샌트랄 글래스 컴퍼니 리미티드 | Process for producing carbonyl difluoride |
| WO2004092067A1 (en) * | 2003-02-17 | 2004-10-28 | Daikin Industries, Ltd. | Method for producing carbonyl difluoride |
| WO2004080894A1 (en) * | 2003-03-14 | 2004-09-23 | Research Institute Of Innovative Technology For The Earth | Process for producing carbonyl fluoride |
| US7332628B2 (en) | 2003-03-14 | 2008-02-19 | National Institute Of Advanced Industrial Science And Technology | Process for producing carbonyl fluoride |
| EP1698592A1 (en) * | 2003-12-11 | 2006-09-06 | Asahi Glass Company Ltd. | Method and apparatus for producing carbonyl fluoride |
| EP1698592A4 (en) * | 2003-12-11 | 2009-07-01 | Asahi Glass Co Ltd | Method and apparatus for producing carbonyl fluoride |
| JP2005206583A (en) * | 2003-12-25 | 2005-08-04 | Sumitomo Chemical Co Ltd | Method for producing fluoride ion-containing alkyl-substituted imidazolium salt |
| JP4851463B2 (en) * | 2005-09-27 | 2012-01-11 | 独立行政法人産業技術総合研究所 | Method for producing carbonyl fluoride |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3707917B2 (en) | 2005-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2889140B2 (en) | Catalytic dehalogenation of halogen-containing compounds of main group 4 elements | |
| JP2929577B2 (en) | Nitrogen trifluoride synthesis method | |
| JP3707917B2 (en) | Method for producing carbonyl fluoride | |
| JPH02258610A (en) | Production of hydrogen peroxide | |
| EP2165973B1 (en) | Method for production of iodine heptafluoride | |
| JPS61257949A (en) | Manufacture of fluoroxyhalo compound | |
| EP1770061B1 (en) | Method for producing carbonyl difluoride | |
| JP3494344B2 (en) | Method for producing lithium hexafluorophosphate | |
| JP3258413B2 (en) | Method for producing germanium tetrafluoride | |
| DK605889A (en) | PROCEDURE FOR THE PRODUCTION OF SILICON NITRID AND PRODUCT PREPARED BY THE PROCEDURE | |
| US20040096387A1 (en) | Method for nitrogen trifluoride production | |
| US4430514A (en) | Novel method for the preparation of CF3 NF2 | |
| EP0516000A1 (en) | Process for fluorinating halogenated hydrocarbon | |
| JP4104320B2 (en) | Method for producing carbonyl difluoride | |
| CN112209803A (en) | Process for producing vinyl compound | |
| JPH0659331B2 (en) | Treatment method of carbon tetrachloride | |
| EP0310255A1 (en) | Production of carbonyl difluoride | |
| JP2005536427A (en) | Method for producing SO2F2 and SO2ClF | |
| JP3865571B2 (en) | Method for producing trifluoromethyl hypofluorite | |
| KR102549706B1 (en) | Method for producing boron trichloride | |
| JPS63139151A (en) | Manufacture of perhalohydrocarbon hypochlorite | |
| JP2004277215A (en) | Method for manufacturing carbonyl fluoride | |
| JPH09183743A (en) | Production of lower perfluoroalkane | |
| JP3188519B2 (en) | Method for producing tert-butyl chloride | |
| JP4978051B2 (en) | Method for producing ammonium cryolite |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20050113 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20050802 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20050802 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080812 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090812 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090812 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090812 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100812 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100812 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110812 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110812 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120812 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120812 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120812 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130812 Year of fee payment: 8 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130812 Year of fee payment: 8 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |