JPH11116216A - Production of carbonyl fluoride - Google Patents

Production of carbonyl fluoride

Info

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
Application number
JP9272831A
Other languages
Japanese (ja)
Other versions
JP3707917B2 (en
Inventor
Masayuki Takashima
正之 高島
Susumu Yonezawa
晋 米沢
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Central Glass Co Ltd
Original Assignee
Central Glass Co Ltd
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 Central Glass Co Ltd filed Critical Central Glass Co Ltd
Priority to JP27283197A priority Critical patent/JP3707917B2/en
Publication of JPH11116216A publication Critical patent/JPH11116216A/en
Application granted granted Critical
Publication of JP3707917B2 publication Critical patent/JP3707917B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Abstract

PROBLEM TO BE SOLVED: To produce carbonyl fluoride at a low cost without using a phosgene and carbon monoxide that are highly toxicix by allowing carbon dioxide to react with fluorine in a gaseous state. SOLUTION: The carbon dioxide and the fluorine are allowed to react with each other in the gaseous state at a temp. in the range of 150-400 deg.C, preferably 150-250 deg.C. In the reaction, either batch type or flow type may be used. A molar ratio of the carbon dioxide to the fluorine is in the range of 0.1-10, preferably 0.5-2. A reaction pressure may be selected properly depending on a reaction temp. and mixing ratio but the pressure near the atmosphere which is easy in handling may be selected preferably. A fluorine resistant metal, etc., such as nickel, nickel alloy, stainless steel, copper and aluminum and a fluorine resistant ceramic, etc., such as quartz, alumina, silicon carbide and aluminum nitride are used as a material of the reaction vessel. The vessel from which a water content is completely removed is preferably used as the reaction device and a preservation vessel of a produced carbonyl fluoride.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【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.,,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)

【特許請求の範囲】[Claims] 【請求項1】 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。
1. A method for producing carbonyl fluoride, comprising reacting carbon dioxide and fluorine in a gaseous state.
JP27283197A 1997-10-06 1997-10-06 Method for producing carbonyl fluoride Expired - Fee Related JP3707917B2 (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101254417B1 (en) 2008-10-06 2013-04-15 쇼와 덴코 가부시키가이샤 Process for producing carbonyl difluoride

Cited By (10)

* Cited by examiner, † Cited by third party
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

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