JP2946103B2 - Method for collecting trifluoromethanesulfonic acid fluoride - Google Patents
Method for collecting trifluoromethanesulfonic acid fluorideInfo
- Publication number
- JP2946103B2 JP2946103B2 JP2099586A JP9958690A JP2946103B2 JP 2946103 B2 JP2946103 B2 JP 2946103B2 JP 2099586 A JP2099586 A JP 2099586A JP 9958690 A JP9958690 A JP 9958690A JP 2946103 B2 JP2946103 B2 JP 2946103B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethanesulfonic acid
- gas
- acid fluoride
- fluoride
- collecting
- 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.)
- Expired - Lifetime
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- Gas Separation By Absorption (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、ペルフルオロアルキルスルホン酸フッ化
物、特にトリフルオロメタンスルホン酸フッ化物の捕集
方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for collecting perfluoroalkyl sulfonic acid fluoride, particularly trifluoromethane sulfonic acid fluoride.
トリフルオロメタンスルホン酸（CF3SO3H）は、いわ
ゆる「超強酸」の一種であり、また、耐熱性、耐酸化還
元性に優れているため、近年、有用な酸触媒として注目
されている（たとえば、重合用触媒、異性課触媒）。ま
た、その酸無水物はアルキル化剤として有用であり、リ
チウム塩はリチウム電池電解質として用いられるなど、
誘導体の工業的利用分野も多岐にわたっている。Trifluoromethanesulfonic acid (CF 3 SO 3 H) is a type of so-called “super-strong acid” and has been attracting attention as a useful acid catalyst in recent years because of its excellent heat resistance and oxidation-reduction resistance ( For example, polymerization catalysts, isomerization catalysts). Also, the acid anhydride is useful as an alkylating agent, lithium salt is used as a lithium battery electrolyte,
The industrial applications of derivatives are also diverse.
トリフルオロメタンスルホン酸は、工業的には、以下
に示す反応経路に従い製造される： （ここでＭはアルカリ金属またはアルカリ土類金属を、
ｍは１または２を表わす） すなわち、メタンスルホン酸フッ化物またはその塩化
物を電解フッ素化してトリフルオロメタンスルホン酸フ
ッ化物とし（上記（１））、ついで、これをアルカリ金
属またはアルカリ土類金属水溶液と接触させてトリフル
オロメタンスルホン酸塩とし（上記（２））、得られた
塩を硫酸によって加水分解する（上記（３））。Trifluoromethanesulfonic acid is industrially produced according to the following reaction route: (Where M is an alkali metal or alkaline earth metal,
m represents 1 or 2) That is, methanesulfonic acid fluoride or its chloride is electrolytically fluorinated to obtain trifluoromethanesulfonic acid fluoride ((1) above), which is then contacted with an aqueous alkali metal or alkaline earth metal solution to obtain trifluoromethanesulfonic acid. It is converted into a salt ((2) above), and the obtained salt is hydrolyzed with sulfuric acid ((3)).
しかし、上記電解フッ素化反応においては、生成する
トリフルオロメタンスルホン酸フッ化物が気体（沸点：
−23℃）であり、多量の副生成ガス（H2）で稀釈されて
いる。このため、直ちにアルカリ金属またはアルカリ土
類金属水溶液と接触させる方法ではフッ化物の大部分が
溶液中で塩に転化することなく液外に散逸してしまう。
よって、金属塩への転化に先立ってフッ化物のみを効率
的に捕集する必要がある。However, in the above electrolytic fluorination reaction, the generated trifluoromethanesulfonic acid fluoride is a gas (boiling point:
−23 ° C.) and diluted with a large amount of by-product gas (H 2 ). Therefore, in a method in which the fluoride is immediately brought into contact with an aqueous solution of an alkali metal or an alkaline earth metal, most of the fluoride escapes out of the solution without being converted into a salt in the solution.
Therefore, it is necessary to efficiently collect only the fluoride prior to the conversion to the metal salt.
このための捕集方法としては、従来、活性炭等による
吸着法、冷却による液化法、水酸化ナトリウムやアミン
等の塩基を用いた化学吸着法、隔膜を用いた分離捕集
法、溶媒による吸収法等が提案されている。As the collection method for this purpose, there have been conventionally used an adsorption method using activated carbon, a liquefaction method using cooling, a chemical adsorption method using a base such as sodium hydroxide or an amine, a separation collection method using a diaphragm, and an absorption method using a solvent. Etc. have been proposed.
しかし、活性炭素による吸着法では、吸収剤単位重量
あたりの吸着量が十分ではないため、大量のトリフルオ
ロメタンスルホン酸フッ化物を吸着させるためには多量
の吸着剤が必要となる。また、脱離工程では通常、熱エ
ネルギーの投入が必要である。液化法では純度の高いト
リフルオロメタンスルホン酸フッ化物が得られるが、冷
却に要するエネルギーコストが多大であり、加圧液化に
より冷却温度を上げる場合には多大の設備投資が要求さ
れる。化学吸着法では、吸着は容易に進行するが、フッ
化物の脱離が困難である。分離捕集法は、電解フッ素化
槽に隔膜を設け、陰極に発生する副生ガスと陽極に発生
するフッ化物ガスを分離するものであるが、電解槽の構
造そのものを変更しなければならず、既存の設備の設計
変更が必要である。However, in the adsorption method using activated carbon, since the amount of adsorption per unit weight of the absorbent is not sufficient, a large amount of adsorbent is required to adsorb a large amount of trifluoromethanesulfonic acid fluoride. Further, in the desorption step, it is usually necessary to input thermal energy. In the liquefaction method, trifluoromethanesulfonic acid fluoride having a high purity can be obtained, but the energy cost required for cooling is large, and a large capital investment is required when the cooling temperature is increased by pressurized liquefaction. In the chemisorption method, adsorption proceeds easily, but desorption of fluoride is difficult. The separation and trapping method involves providing a diaphragm in an electrolytic fluorination tank and separating the by-product gas generated at the cathode and the fluoride gas generated at the anode, but the structure of the electrolytic cell itself must be changed. However, it is necessary to change the design of existing equipment.
また、フッ化物ガスを捕集する場合でもこれを直接KO
H水溶液に接触させ、該水溶液中に該ガスを吸収させる
と同時に金属塩に転化するという従来法には、KOH水溶
液へのフッ化物の吸収速度が著しく遅く実用性に乏しい
という問題がある。In addition, even if fluoride gas is collected, this can be directly
The conventional method of contacting with an H aqueous solution to absorb the gas in the aqueous solution and converting the gas into a metal salt at the same time has a problem in that the absorption rate of fluoride into the KOH aqueous solution is extremely low and the practicality is poor.
本発明者らは、トリフルオロメタンスルホン酸フッ化
物を工業的規模で効率的に捕集する方法を検討した結
果、ある種のフッ素系不活性溶媒がフッ化物吸収力に優
れておりこれを捕集溶媒として用い、ついで、該溶媒か
らフッ化物の抽出および金属塩の転化を行なうことで上
記課題が達成できることを見出した。The present inventors have studied a method for efficiently collecting trifluoromethanesulfonic acid fluoride on an industrial scale, and as a result, it has been found that a certain type of fluorine-based inert solvent has an excellent fluoride-absorbing power, and this type of solvent is collected. It has been found that the above-mentioned problems can be achieved by using the compound as a solvent and then extracting the fluoride from the solvent and converting the metal salt.
本発明は、トリフルオロメタンスルホン酸フッ化物を
含む気体をフッ素系不活性溶媒と接触させることからな
るトリフルオロメタンスルホン酸フッ化物の捕集方法を
提供する。The present invention provides a method for collecting trifluoromethanesulfonic acid fluoride, which comprises contacting a gas containing trifluoromethanesulfonic acid fluoride with a fluorine-based inert solvent.
また、本発明は、特にメタンスルホン酸フッ化物また
はメタンスルホン酸塩化物の電解フッ素化により生成し
たトリフルオロメタンスルホン酸フッ化物を含む気体混
合物をフッ素系不活性溶媒と接触させることからなるト
リフルオロメタンスルホン酸フッ化物の捕集方法を提供
する。The present invention also relates to trifluoromethanesulfone, which comprises contacting a gas mixture containing trifluoromethanesulfonate fluoride formed by electrolytic fluorination of methanesulfonate fluoride or methanesulfonate with a fluorine-based inert solvent. Provided is a method for collecting oxyfluoride.
本発明の方法は、トリフルオロメタンスルホン酸フッ
化物単体またはこれと反応しない任意の気体との混合物
に対して適用できる。特にメタンスルホン酸フッ化物ま
たはメタンスルホン酸塩化物の電解フッ素化により生成
したトリフルオロメタンスルホン酸フッ化物を含む気体
混合物に対して有用である。The method of the present invention can be applied to trifluoromethanesulfonic acid fluoride alone or a mixture with any gas that does not react therewith. In particular, it is useful for gas mixtures containing trifluoromethanesulfonic acid fluoride produced by electrolytic fluorination of methanesulfonic acid fluoride or methanesulfonic acid chloride.
本発明で用いるフッ素系不活性溶媒は、本発明の方法
が適用されるトリフルオロメタンスルホン酸フッ化物お
よびこれと混合した気体のいずれとも反応しないもので
あれば、いずれをも用いることができ、炭素、水素、フ
ッ素以外の元素を含有していてもよい。代表的な例とし
ては、 およびこれらの混合物がある。これらのフッ素系不活性
溶媒は、例えば、20％KOH水溶液と比べ、フッ化物の吸
収速度が数十倍速い。As the fluorinated inert solvent used in the present invention, any one can be used as long as it does not react with any of trifluoromethanesulfonic acid fluoride to which the method of the present invention is applied and a gas mixed therewith. , Hydrogen and fluorine. A typical example is And mixtures thereof. These fluorine-based inert solvents have a fluoride absorption rate several tens times faster than, for example, a 20% KOH aqueous solution.
捕集は、フッ素系不活性溶媒が液体である限り可能で
あるが、好ましくは常圧下、20℃以下、より好ましくは
−15℃〜20℃の温度範囲で行なう。20℃を超え高温にな
るとトリフルオロメタンスルホン酸フッ化物およびフッ
素系不活性溶媒の逸散量が増え吸収効率も低下する。ま
た、−15℃より低温に冷却する場合には、冷却に要する
エネルギーコストが増大し、経済的に不利である。Collection is possible as long as the fluorinated inert solvent is a liquid, but is preferably carried out under normal pressure at a temperature of 20 ° C. or lower, more preferably -15 ° C. to 20 ° C. When the temperature is higher than 20 ° C., the amount of trifluoromethanesulfonic acid fluoride and the fluorine-based inert solvent that escapes increases, and the absorption efficiency decreases. On the other hand, when cooling to a temperature lower than −15 ° C., the energy cost required for cooling increases, which is economically disadvantageous.
トリフルオロメタンスルホン酸フッ化物とフッ素系不
活性溶媒との接触方法は特に限定されない。The method of contacting the trifluoromethanesulfonic acid fluoride with the fluorine-based inert solvent is not particularly limited.
また、本発明の方法により捕集したトリフルオロメタ
ンスルホン酸フッ化物は、溶媒に含有させたままアルカ
リ金属塩に接触させることで、その分離および塩への転
化が容易に達成できる。In addition, the trifluoromethanesulfonic acid fluoride collected by the method of the present invention can be easily separated and converted to a salt by bringing the trifluoromethanesulfonic acid fluoride into contact with an alkali metal salt while being contained in a solvent.
実施例１ １の電解槽を用いて、電流密度1A/dm2、電圧５〜6
V、温度８〜13℃の条件で、CH3SO2Clを10.9g/時間ずつ
供給しながら連続電解フッ素化を行なった。Example 1 Using the electrolytic cell of 1, a current density of 1 A / dm 2 and a voltage of 5 to 6
Under a condition of V and a temperature of 8 to 13 ° C., continuous electrolytic fluorination was performed while supplying CH 3 SO 2 Cl at a rate of 10.9 g / hour.
電解フッ素化生成ガスを、始めに水洗塔に導入してH
F、Cl2を除き、次に内径5cm、８×8mmのラッシヒリング
を充填（層高30cm）したテフロン製ガス吸収塔に導き、
操作温度７〜８℃で、ペルフルオロ環状エーテル（EFTO
P EF−L102:環状エーテルC5F9O（C3F7）と環状エーテ
ルC4F7O（C4F9）との混合物）を27.6kg/時間で流しなが
ら、ガスと向流接触させた。 The electrolytic fluorinated product gas is first introduced into the washing tower and H
F, ClTwo, Then a Raschig ring with an inner diameter of 5 cm and 8 x 8 mm
Into a Teflon gas absorption tower filled with
At an operating temperature of 7-8 ° C, a perfluorocyclic ether (EFTO
P EF-L102: Cyclic ether CFiveF9O (CThreeF7) And cyclic athe
Le CFourF7O (CFourF9) At 27.6kg / hour
Were brought into countercurrent contact with the gas.
吸収塔出入口のガス組成を分析、比較したところCF3S
O2Fガスの97〜95％が吸収されていた。CF 3 S where the gas composition of the absorption tower doorway analysis and compared
97 to 95% of O 2 F gas had been absorbed.
ペルフルオロ環状エーテルのガスクロマトグラフィー
分析（Silicone KF−96,10m,30℃）により、相当量のCF
3SO2Fが存在することを確認した。By gas chromatography analysis of perfluorocyclic ether (Silicone KF-96, 10m, 30 ° C), a considerable amount of CF
3 SO 2 F was confirmed to be present.
実施例２ 実施例１と同様な条件によりCH3SO2Clの電解フッ素化
を行なった。吸収液としてペルフルオロトリブチルアミ
ン（EFTOP EF−L174:(C4F9)3N）を用いた。Example 2 CH under the same conditions as in Example 1ThreeSOTwoElectrolytic fluorination of Cl
Was performed. Perfluorotributylamide as an absorbing solution
(EFTOP EF-L174: (CFourF9)ThreeN) was used.
吸収管出入口のガス組成を分析、比較したところCF3S
O2Fガスの95％以上が吸収されていた。CF 3 S where the gas composition of the absorption tube entrance analysis and compared
More than 95% of the O 2 F gas was absorbed.
ペルフルオロトリブチルアミンのガスクロマトグラフ
ィー分析により、相当量のCF3SO2Fの存在を確認した。Gas chromatographic analysis of perfluorotributylamine confirmed the presence of significant amounts of CF 3 SO 2 F.
実施例３ 実施例１と同様な電解層を用いてCH3SO2Fの電解フッ
素化を行なった。CH3SO2FはCH3SO2Clと酸性フッ化カリ
ウム（KF・HF）水溶液との反応により合成し、蒸留精製
して使用した（bp.123〜124℃）。CH3SO2Fを時間当たり
9.3gずつ供給したほかは、実施例１と同様な操作を行な
った。Example 3 Using the same electrolytic layer as in Example 1, electrolytic fluorination of CH 3 SO 2 F was performed. CH 3 SO 2 F was synthesized by reacting CH 3 SO 2 Cl with an aqueous solution of potassium acid fluoride (KF · HF), and purified by distillation before use (bp. 123 to 124 ° C.). CH 3 SO 2 F per hour
The same operation as in Example 1 was performed, except that 9.3 g of the mixture was supplied.
吸収塔出入口のガス組成分析により、95％以上のCF3S
O2Fが吸収されたことが確認された。またペルフルオロ
環状エーテルのガスクロマトグラフィー分析から、相当
量のCF3SO2Fの存在を確認した。Analysis of gas composition at the entrance and exit of the absorption tower revealed that more than 95% of CF 3 S
It was confirmed that O 2 F was absorbed. Gas chromatography analysis of the perfluorocyclic ether confirmed the presence of a significant amount of CF 3 SO 2 F.
実施例４ 内径2.1cm、容積100mlの円筒型容器内を85％のCF3SO2
Fガスで満たした（純ガスをairで希釈）。次にこの容器
に、吸収液としてペルフルオロオクタン（C8F18）15ml
を加えた。吸収によって減少していく気体体積をガスビ
ュレットで追跡した。測定中は系内圧力が大気圧と等し
くなるよう調節した。Example 4 A cylindrical container having an inner diameter of 2.1 cm and a volume of 100 ml was filled with 85% CF 3 SO 2.
Filled with F gas (pure gas diluted with air). Next, add 15 ml of perfluorooctane (C 8 F 18 ) as an absorbing solution to this container.
Was added. The gas volume decreasing by absorption was tracked with a gas burette. During the measurement, the pressure in the system was adjusted to be equal to the atmospheric pressure.
約50ml減少するまでに要する時間を測定し、平均の吸
収速度を算出した。吸収実験は、20℃に空調された恒温
室内で行なった。The time required to decrease by about 50 ml was measured, and the average absorption rate was calculated. The absorption experiment was performed in a constant temperature room air-conditioned at 20 ° C.
結果を第１表に示す。 The results are shown in Table 1.
実施例５ 吸収液としてペルフルオロトリペンチルアミン（EFTO
P EF−L215:(C5F11)3N）を用いた以外は実施例４と同
様な操作を行ない平均の吸収速度を求めた。Example 5 As an absorbing solution, perfluorotripentylamine (EFTO) was used.
P EF-L215: (CFiveF11)ThreeSame as Example 4 except that N) was used
The same operation was performed to determine the average absorption rate.
結果を第１表に示す。 The results are shown in Table 1.
実施例６ 吸収液としてペルフルオロポリエーテル（KRYTOX 1
43AA: を用いた以外は実施例４と同様な操作を行ない平均の吸
収速度を求めた。Example 6 A perfluoropolyether (KRYTOX 1
43AA:The same operation as in Example 4 was performed except that
The yield rate was determined.
結果を第１表に示す。 The results are shown in Table 1.
実施例７ 吸収液としてペルフルオロ−Ｎ−メチルキノリン（C
10F19N）を用いた以外は実施例４と同様な操作を行ない
平均の吸収速度を求めた。Example 7 Perfluoro-N-methylquinoline (C
The same operation as in Example 4 was performed except that 10 F 19 N) was used, and the average absorption rate was determined.
結果を第１表に示す。 The results are shown in Table 1.
比較例１〜５ 比較のために、種々のアルカリ水溶液を吸収液として
用いた。Comparative Examples 1 to 5 For comparison, various alkaline aqueous solutions were used as the absorbing solution.
結果を第１表に示す。 The results are shown in Table 1.
〔発明の効果〕 本発明の方法によれば、強度の冷却または加圧を必要
とせずに、トリフルオロメタンスルホン酸フッ化物を工
業的規模で効率的に捕集することができる。また、本発
明の方法によればフッ化物の吸収が迅速であるため、ト
リフルオロメタンスルホン酸フッ化物を連続的に捕集す
ることが可能である。 [Effect of the Invention] According to the method of the present invention, trifluoromethanesulfonic acid fluoride can be efficiently collected on an industrial scale without the need for strong cooling or pressurization. In addition, according to the method of the present invention, since fluoride is rapidly absorbed, trifluoromethanesulfonic acid fluoride can be continuously collected.
Claims (3)
含む気体をフッ素系不活性溶媒と接触させることからな
るトリフルオロメタンスルホン酸フッ化物の捕集方法。1. A method for collecting trifluoromethanesulfonic acid fluoride, comprising contacting a gas containing trifluoromethanesulfonic acid fluoride with a fluorine-based inert solvent.
体がメタンスルホン酸フッ化物またはメタンスルホン酸
塩化物の電解フッ素化により生成したものである方法。2. The method according to claim 1, wherein said gas is produced by electrolytic fluorination of methanesulfonic acid fluoride or methanesulfonic acid chloride.
あって、該フッ素系不活性溶媒が、６〜20個の炭素原子
を含むペルフルオロアルカン;9〜20個の炭素原子を含む
ペルフルオロアルキルアミン;1以上の複素原子を含むも
しくは含まないペルフルオロ単環もしくは縮合環化合物
であって、１〜５個の炭素原子からなる置換基を有しも
しくは有さず該複素原子が窒素原子もしくは酸素原子で
あるもの；およびペルフルオロポリエーテルからなる群
より選ばれるもの、またはその混合物である方法。3. The method according to claim 1, wherein the fluorinated inert solvent is a perfluoroalkane containing 6 to 20 carbon atoms; a perfluoroalkane containing 9 to 20 carbon atoms. Alkylamine; a perfluoromonocyclic or condensed ring compound containing or not containing one or more heteroatoms, having or not having a substituent consisting of 1 to 5 carbon atoms, wherein the heteroatom is a nitrogen atom or oxygen A method selected from the group consisting of atoms; and perfluoropolyether, or a mixture thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2099586A JP2946103B2 (en) | 1990-04-16 | 1990-04-16 | Method for collecting trifluoromethanesulfonic acid fluoride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2099586A JP2946103B2 (en) | 1990-04-16 | 1990-04-16 | Method for collecting trifluoromethanesulfonic acid fluoride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03296412A JPH03296412A (en) | 1991-12-27 |
| JP2946103B2 true JP2946103B2 (en) | 1999-09-06 |
Family
ID=14251203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2099586A Expired - Lifetime JP2946103B2 (en) | 1990-04-16 | 1990-04-16 | Method for collecting trifluoromethanesulfonic acid fluoride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2946103B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69501366T2 (en) * | 1994-07-01 | 1998-04-16 | Haldor Topsoe As | Process for the electrochemical fluorination of a hydrocarbon substrate |
| FR2810672B1 (en) * | 2000-06-22 | 2003-11-07 | Extractive | PROCESS FOR THE FRACTIONATION OF ESSENTIAL OILS USING AT LEAST ONE FLUOROUS SOLVENT |
| JP5051568B2 (en) * | 2005-09-30 | 2012-10-17 | 三菱マテリアル株式会社 | Method for producing potassium perfluoroalkanesulfonate |
| JP5345478B2 (en) * | 2009-08-28 | 2013-11-20 | 三菱マテリアル株式会社 | Method and apparatus for recovering perfluoroalkanesulfonyl fluoride |
| WO2012039024A1 (en) * | 2010-09-21 | 2012-03-29 | 三菱マテリアル株式会社 | Method and device for recovering perfluoroalkanesulfonyl fluoride |
-
1990
- 1990-04-16 JP JP2099586A patent/JP2946103B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03296412A (en) | 1991-12-27 |
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