JP5061635B2 - Process for producing 4-fluoro-1,3-dioxolan-2-one - Google Patents
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Abstract
Description
本発明は、４−フルオロ−１，３−ジオキソラン−２−オンを短時間で高収率にて製造する方法に関する。 The present invention relates to a method for producing 4-fluoro-1,3-dioxolan-2-one in a short time and in a high yield.
４−フルオロ−１，３−ジオキソラン−２−オン（以下、「Ｆ−ＥＣ」という）は、二次電池やキャパシタなどの電気化学デバイスに用いる電解液の溶媒として、充放電サイクル特性や電流効率などに優れる点から注目されている。 4-Fluoro-1,3-dioxolan-2-one (hereinafter referred to as “F-EC”) is a solvent for electrolytes used in electrochemical devices such as secondary batteries and capacitors, and is used for charge / discharge cycle characteristics and current efficiency. It is attracting attention because of its superiority.
このＦ−ＥＣの製造法としては、１，３−ジオキソラン−２−オンを出発物質とし、フッ素ガスで直接フッ素化する方法と、フッ素化剤として金属フッ化物を用いて４−クロロ−１，３−ジオキソラン−２−オン（以下、「Ｃｌ−ＥＣ」という）の４位の塩素原子をフッ素原子で置換する方法が知られている（特許文献１、２）。 As a method for producing this F-EC, 1,3-dioxolan-2-one is used as a starting material, a method of directly fluorinating with a fluorine gas, and 4-chloro-1, A method is known in which the chlorine atom at the 4-position of 3-dioxolan-2-one (hereinafter referred to as “Cl-EC”) is substituted with a fluorine atom (Patent Documents 1 and 2).
特許文献１では、Ｃｌ−ＥＣとフッ化カリウムとを混ぜて反応させてＦ−ＥＣを収率７０％で得たと記載されているが、反応溶媒や反応温度、反応時間といった基本的な条件の開示もない。 In Patent Document 1, it is described that Cl-EC and potassium fluoride are mixed and reacted to obtain F-EC in a yield of 70%. However, the basic conditions such as reaction solvent, reaction temperature, and reaction time are described. There is no disclosure.
特許文献２では、Ｃｌ−ＥＣとフッ化カリウムとをアセトニトリル中で８０〜８５℃にて１１時間かけて反応させ、出発物質のＣｌ−ＥＣを含むＦ−ＥＣの粗生成物を収率８７．５％で得ている（再結晶すると、粗生成物の８５％でＦ−ＥＣが採取できる）。 In Patent Document 2, Cl-EC and potassium fluoride are reacted in acetonitrile at 80 to 85 ° C. for 11 hours to obtain a crude product of F-EC containing Cl—EC as a starting material in a yield of 87. It is obtained in 5% (when recrystallized, F-EC can be collected in 85% of the crude product).
本発明は、Ｃｌ−ＥＣを出発物質とし、これをフッ素化剤でフッ素化する製造法において、高収率を維持しながら短時間でＦ−ＥＣを製造する方法を提供することを目的とする。 An object of the present invention is to provide a method for producing F-EC in a short time while maintaining a high yield in a production method in which Cl-EC is used as a starting material and fluorinated with a fluorinating agent. .
本発明は、
式（１）：
Ｒ4Ｎ+Ｘ- （１）
（式中、Ｒは炭素数１〜７のアルキル基、フェニル基、ベンジル基またはシクロアルキル基；Ｘはハロゲン原子）で示される４級アンモニウムカチオンとハロゲンアニオンとの化合物を触媒とし、４−クロロ−１，３−ジオキソラン−２−オン（Ｃｌ−ＥＣ）を有機溶媒中にて金属フッ化物によりフッ素化することを特徴とする４−フルオロ−１，３−ジオキソラン−２−オン（Ｆ−ＥＣ）の製造法に関する。
The present invention
Formula (1):
R 4 N + X - (1 )
(Wherein R is an alkyl group having 1 to 7 carbon atoms, phenyl group, benzyl group or cycloalkyl group; X is a halogen atom), and a compound of a quaternary ammonium cation and a halogen anion is used as a catalyst. 4-fluoro-1,3-dioxolan-2-one (F-EC), characterized by fluorinating 1,3-dioxolan-2-one (Cl-EC) with a metal fluoride in an organic solvent ) Manufacturing method.
触媒である４級アンモニウムカチオンとハロゲンアニオンとの化合物としては、式（１）において、Ｒが炭素数１〜７のアルキル基である化合物が、取り扱いが容易である点から好ましい。 As a compound of a quaternary ammonium cation and a halogen anion as a catalyst, a compound in which R is an alkyl group having 1 to 7 carbon atoms in the formula (1) is preferable from the viewpoint of easy handling.
また、触媒である４級アンモニウムカチオンとハロゲンアニオンとの化合物を構成するハロゲン原子としては、フッ素原子であることが、初期の反応性が高い点から好ましい。 In addition, the halogen atom constituting the compound of the quaternary ammonium cation and the halogen anion as a catalyst is preferably a fluorine atom from the viewpoint of high initial reactivity.
有機溶媒としては、非プロトン性溶媒、特にアセトニトリル（ＡＮ）、テトラヒドロフラン（ＴＨＦ）、Ｎ−メチルピロリドン（ＮＭＰ）、Ｎ，Ｎ−ジメチルホルムアミドまたはＮ，Ｎ−ジメチルアセトアミドであることが、誘電率が高い点から好ましい。 The organic solvent is an aprotic solvent, particularly acetonitrile (AN), tetrahydrofuran (THF), N-methylpyrrolidone (NMP), N, N-dimethylformamide or N, N-dimethylacetamide, It is preferable from a high point.
金属フッ化物としては、アルカリ金属フッ化物が、取り扱いやすく反応性が高い点から好ましい。 As the metal fluoride, alkali metal fluoride is preferable because it is easy to handle and has high reactivity.
触媒である４級アンモニウムカチオンとハロゲンアニオンとの化合物は、金属フッ化物の０．０１〜０．５等量使用することが、反応性が高い点から好ましい。 The compound of a quaternary ammonium cation and a halogen anion, which is a catalyst, is preferably used in an amount of 0.01 to 0.5 equivalent of metal fluoride from the viewpoint of high reactivity.
本発明の製造法によれば、高収率を維持しながら短時間でＦ−ＥＣを製造することができる。 According to the production method of the present invention, F-EC can be produced in a short time while maintaining a high yield.
本発明のＦ−ＥＣの製造法は、特定の４級アンモニウムカチオンとハロゲンアニオンとの化合物を触媒とし、Ｃｌ−ＥＣを有機溶媒中にて金属フッ化物によりフッ素化することを特徴とする。 The method for producing F-EC of the present invention is characterized in that Cl-EC is fluorinated with a metal fluoride in an organic solvent using a compound of a specific quaternary ammonium cation and a halogen anion as a catalyst.
本発明の製造法の反応式はつぎのとおりである。 The reaction formula of the production method of the present invention is as follows.
なお、ＭＦは金属フッ化物（固体）であり、また出発物質のＣｌ−ＥＣと目的物質のＦ−ＥＣはいずれも液体である。 MF is a metal fluoride (solid), and Cl-EC as a starting material and F-EC as a target material are both liquids.
本発明で使用する触媒は、
式（１）：
Ｒ4Ｎ+Ｘ- （１）
で示される４級アンモニウムカチオンとハロゲンアニオンとの化合物である。
The catalyst used in the present invention is:
Formula (1):
R 4 N + X - (1 )
It is a compound of the quaternary ammonium cation and halogen anion shown by these.
４級アンモニウムカチオンとハロゲンアニオンとの化合物（１）のＲとしては、炭素数１〜７のアルキル基、フェニル基、ベンジル基またはシクロアルキル基であり、特に極性溶媒への溶解性が良好な点から、メチル、エチル、ｎ−プロピル、ｎ−ブチル、シクロプロピル、シクロブチル、イソプロピル、イソブチルなどが好ましい。 R in the compound (1) of a quaternary ammonium cation and a halogen anion is an alkyl group having 1 to 7 carbon atoms, a phenyl group, a benzyl group or a cycloalkyl group, and particularly has good solubility in a polar solvent. Therefore, methyl, ethyl, n-propyl, n-butyl, cyclopropyl, cyclobutyl, isopropyl, isobutyl and the like are preferable.
Ｘはハロゲン原子であり、塩素原子、フッ素原子、臭素原子などがあげられるが、なかでも初期の反応性が高い点からフッ素原子が好ましい。 X is a halogen atom, and examples thereof include a chlorine atom, a fluorine atom, and a bromine atom. Among these, a fluorine atom is preferable from the viewpoint of high initial reactivity.
４級アンモニウムカチオンとハロゲンアニオンとの化合物（１）の具体例としては、たとえばテトラメチルアンモニウムフルオライド、テトラエチルアンモニウムフルオライド、テトラプロピルアンモニウムフルオライド、テトラブチルアンモニウムフルオライドなどがあげられる。 Specific examples of the compound (1) of a quaternary ammonium cation and a halogen anion include, for example, tetramethylammonium fluoride, tetraethylammonium fluoride, tetrapropylammonium fluoride, and tetrabutylammonium fluoride.
金属フッ化物はフッ素化剤として機能する。フッ化物を構成する金属としては、リチウム、カリウム、ナトリウムなどのアルカリ金属が取り扱いやすさや反応性が高い点から好ましく、特にカリウムが反応性が高い点で特に好ましい。 The metal fluoride functions as a fluorinating agent. As the metal constituting the fluoride, alkali metals such as lithium, potassium and sodium are preferable from the viewpoint of easy handling and reactivity, and potassium is particularly preferable from the viewpoint of high reactivity.
これらの金属フッ化物は固体であり、スプレー乾燥した微粒子、粉砕した粉末などの形状で反応に供される。 These metal fluorides are solid, and are subjected to the reaction in the form of spray-dried fine particles, pulverized powder, and the like.
本発明の反応は、有機溶媒中で行う。水が存在すると反応性が低下するので、実質的に無水の状態で行うことが望ましい。 The reaction of the present invention is carried out in an organic solvent. Since the reactivity is lowered in the presence of water, it is desirable to carry out in a substantially anhydrous state.
有機溶媒としては非プロトン性有機溶媒が好ましく、さらには反応速度が大きくなる点から極性有機溶媒が好ましい。具体的には、アセトニトリル（ＡＮ）、テトラヒドロフラン（ＴＨＦ）、Ｎ−メチルピロリドン（ＮＭＰ）、塩化メチレン、クロロホルム、ニトロメタン、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ，Ｎ−ジメチルアセトアミド、１，３−ジメチル−２−イミダゾリジノンなどが例示できる。これらのなかでも誘電率が高く粘性が低い点からアセトニトリルが、また誘電率が高く沸点が好適な点からＮ−メチルピロリドンが好ましい。 The organic solvent is preferably an aprotic organic solvent, and more preferably a polar organic solvent from the viewpoint of increasing the reaction rate. Specifically, acetonitrile (AN), tetrahydrofuran (THF), N-methylpyrrolidone (NMP), methylene chloride, chloroform, nitromethane, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl- Examples include 2-imidazolidinone. Among these, acetonitrile is preferable from the viewpoint of high dielectric constant and low viscosity, and N-methylpyrrolidone is preferable from the viewpoint of high dielectric constant and favorable boiling point.
触媒の使用量としては特に限定されないが、金属フッ化物の０．０１〜０．５等量、さらには０．０１〜０．１等量であることが、反応後の塩化物の後処理が容易である点から好ましい。 The amount of the catalyst used is not particularly limited, but it is 0.01 to 0.5 equivalent of metal fluoride, more preferably 0.01 to 0.1 equivalent, so that the post treatment of chloride after the reaction is performed. It is preferable because it is easy.
出発物質のＣｌ−ＥＣと金属フッ化物の反応は等モル比で進むが、反応性の点から金属フッ化物をＣｌ−ＥＣ１モルに対して１〜２モル、さらには１〜１．５モル使用することが好ましい。 The reaction between the starting material Cl-EC and the metal fluoride proceeds in an equimolar ratio, but from the viewpoint of reactivity, the metal fluoride is used in an amount of 1 to 2 mol, further 1 to 1.5 mol with respect to 1 mol of Cl-EC. It is preferable to do.
有機溶媒中の出発物質のＣｌ−ＥＣの濃度としては、広い範囲が採用できるが、５重量％以上、さらには２０重量％以上であることが反応を制御しやすい点から好ましい。上限は６０重量％、さらには５０重量％が好ましい。 As the concentration of the starting material Cl-EC in the organic solvent, a wide range can be adopted, but it is preferably 5% by weight or more, more preferably 20% by weight or more from the viewpoint of easy control of the reaction. The upper limit is preferably 60% by weight, more preferably 50% by weight.
反応温度は、扱いやすさの点から３０℃以上、さらには５０℃以上が好ましい。また上限は使用する有機溶媒の沸点である。 The reaction temperature is preferably 30 ° C. or higher, more preferably 50 ° C. or higher from the viewpoint of ease of handling. The upper limit is the boiling point of the organic solvent used.
反応は、従来の製造法における反応より早く進み、同等の収率では、従来の反応時間の１／２以下の時間で反応が完結する。収率も８０〜８５％と従来と同等かそれ以上である。 The reaction proceeds faster than the reaction in the conventional production method, and with the same yield, the reaction is completed in a time that is ½ or less of the conventional reaction time. The yield is 80 to 85%, which is equal to or higher than the conventional one.
反応生成物は、たとえば純水で再沈殿させ、得られたＦ−ＥＣの溶液を蒸留することにより精製できる。 The reaction product can be purified by, for example, reprecipitation with pure water and distilling the resulting F-EC solution.
つぎに実施例をあげて本発明の製造法を説明するが、本発明はこれらの実施例に限定されるものではない。 Next, the production method of the present invention will be described with reference to examples, but the present invention is not limited to these examples.
以下の実施例で使用した分析方法はつぎのものである。 The analysis methods used in the following examples are as follows.
（１）ＮＭＲ
装置：ＢＲＵＫＥＲ製のＡＣ−３００
測定条件：
19Ｆ−ＮＭＲ：２８２ＭＨｚ（トリフルオロメチルベンゼン＝−６２．３ｐｐｍ）
1Ｈ−ＭＮＲ：３００ＭＨｚ（トリフルオロメチルベンゼン＝７．５１ｐｐｍ）
(1) NMR
Apparatus: AC-300 manufactured by BRUKER
Measurement condition:
19 F-NMR: 282 MHz (trifluoromethylbenzene = −62.3 ppm)
1 H-MNR: 300 MHz (trifluoromethylbenzene = 7.51 ppm)
（２）ガスクロマトグラフィ（ＧＣ）
装置：島津製作所製のＧＣ−１７Ａ
カラム：ＤＢ６２４（Ｊ＆Ｗサイエンティフィック社製）
測定条件：１００℃→５分間保持→１０℃／分で昇温→２３０℃
(2) Gas chromatography (GC)
Apparatus: GC-17A manufactured by Shimadzu Corporation
Column: DB624 (manufactured by J & W Scientific)
Measurement conditions: 100 ° C. → hold for 5 minutes → temperature rise at 10 ° C./min→230° C.
実施例１
撹拌装置を備えた３０ｍｌのガラス製３口フラスコの上部に還流管を取り付け、スプレー乾燥したフッ化カリウム２．８５ｇ（４９．０ｍｍｏｌ）を加え、真空下で攪拌しながらフレームドライにより水分除去を行った。その後シリンジを用いてアセトニトリル１５ｍｌ、Ｃｌ−ＥＣ５ｇ（４０．６ｍｍｏｌ）、テトラブチルアンモニウムフルオライド−ＴＨＦ溶液（１ｍｏｌ／ｌ）４．９ｍｌ（４．９０ｍｍｏｌ）を加えて攪拌した。反応温度８０℃で反応を行い進行はＧＣを用いて分析した。反応は４時間で終了し、原料のピークの消失を確認した。反応終了後、反応溶液を純水で再沈を行い下層の溶液を採取した。採取後蒸留により精製を行い、８５℃（１００ｍｍＨｇ）の留分として、収率８５％、ＧＣ純度９９．８％でＦ−ＥＣが得られた。
Example 1
Attach a reflux tube to the top of a 30 ml glass three-necked flask equipped with a stirrer, add 2.85 g (49.0 mmol) of spray-dried potassium fluoride, and remove moisture by flame drying while stirring under vacuum. It was. Thereafter, 15 ml of acetonitrile, 5 g (40.6 mmol) of Cl-EC and 4.9 ml (4.90 mmol) of tetrabutylammonium fluoride-THF solution (1 mol / l) were added and stirred using a syringe. The reaction was performed at a reaction temperature of 80 ° C., and the progress was analyzed using GC. The reaction was completed in 4 hours, and disappearance of the raw material peak was confirmed. After completion of the reaction, the reaction solution was reprecipitated with pure water, and the lower layer solution was collected. After collection, purification was performed by distillation, and F-EC was obtained as a fraction at 85 ° C. (100 mmHg) with a yield of 85% and a GC purity of 99.8%.
このＦ−ＥＣを19Ｆ−ＮＭＲ、1Ｈ−ＮＭＲ分析により分析し、４−フルオロ−１，３−ジオキソラン−２−オンであることを確認した。
19Ｆ−ＮＭＲ：（重アセトン）：−１２２．６〜−１２２．３ｐｐｍ（１Ｆ，ｍ）
1Ｈ−ＮＭＲ：（重アセトン）：４．５４〜４．９１ｐｐｍ（２Ｈ，ｍ）、６．４２〜６．６８ｐｐｍ（１Ｈ，ｄｄ）
This F-EC was analyzed by 19 F-NMR and 1 H-NMR analysis and confirmed to be 4-fluoro-1,3-dioxolan-2-one.
19 F-NMR: (heavy acetone): -122.6 to -122.3 ppm (1F, m)
1 H-NMR: (heavy acetone): 4.54 to 4.91 ppm (2H, m), 6.42 to 6.68 ppm (1H, dd)
実施例２
撹拌装置を備えた３０ｍｌのガラス製３口フラスコの上部に還流管を取り付け、粉末のフッ化カリウム２．８５ｇ（４９．０ｍｍｏｌ）を加え、真空下で攪拌しながらフレームドライにより水分除去を行った。その後シリンジを用いてアセトニトリル１５ｍｌ、Ｃｌ−ＥＣ５ｇ（４０．６ｍｍｏｌ）、テトラブチルアンモニウムフルオライド−ＴＨＦ溶液（１ｍｏｌ／ｌ）４．９ｍｌ（４．９０ｍｍｏｌ）を加えて攪拌した。反応温度８０℃で反応を行い進行はＧＣを用いて分析した。反応は９時間で終了し、原料のピークの消失を確認した。反応終了後、反応溶液を純水で再沈を行い下層の溶液を採取した。採取後蒸留により精製を行い、８５℃（１００ｍｍＨｇ）の留分として、収率８５％、ＧＣ純度９９．８％でＦ−ＥＣが得られた。
Example 2
A reflux tube was attached to the top of a 30 ml glass three-necked flask equipped with a stirrer, 2.85 g (49.0 mmol) of powdered potassium fluoride was added, and water was removed by flame drying while stirring under vacuum. . Thereafter, 15 ml of acetonitrile, 5 g (40.6 mmol) of Cl-EC and 4.9 ml (4.90 mmol) of tetrabutylammonium fluoride-THF solution (1 mol / l) were added and stirred using a syringe. The reaction was performed at a reaction temperature of 80 ° C., and the progress was analyzed using GC. The reaction was completed in 9 hours, and disappearance of the raw material peak was confirmed. After completion of the reaction, the reaction solution was reprecipitated with pure water, and the lower layer solution was collected. After collection, purification was performed by distillation, and F-EC was obtained as a fraction at 85 ° C. (100 mmHg) with a yield of 85% and a GC purity of 99.8%.
このＦ−ＥＣを19Ｆ−ＮＭＲ、1Ｈ−ＮＭＲ分析により分析し、４−フルオロ−１，３−ジオキソラン−２−オンであることを確認した。 This F-EC was analyzed by 19 F-NMR and 1 H-NMR analysis and confirmed to be 4-fluoro-1,3-dioxolan-2-one.
実施例３
撹拌装置を備えた３０ｍｌのガラス製３口フラスコの上部に還流管を取り付け、スプレー乾燥したフッ化カリウム２．８５ｇ（４９．０ｍｍｏｌ）を加え、真空下で攪拌しながらフレームドライにより水分除去を行った。その後シリンジを用いてＮ−メチルピロリドン１５ｍｌ、Ｃｌ−ＥＣ５ｇ（４０．６ｍｍｏｌ）、テトラブチルアンモニウムフルオライド−ＴＨＦ溶液（１ｍｏｌ／ｌ）４．９ｍｌ（４．９０ｍｍｏｌ）を加えて攪拌した。反応温度８０℃で反応を行い進行はＧＣを用いて分析した。反応は８時間で終了し、原料のピークの消失を確認した。反応終了後、反応溶液を純水で再沈を行い下層の溶液を採取した。採取後蒸留により精製を行い、８５℃（１００ｍｍＨｇ）の留分として、収率８５％、ＧＣ純度９９．８％でＦ−ＥＣが得られた。
Example 3
Attach a reflux tube to the top of a 30 ml glass three-necked flask equipped with a stirrer, add 2.85 g (49.0 mmol) of spray-dried potassium fluoride, and remove moisture by flame drying while stirring under vacuum. It was. Thereafter, 15 ml of N-methylpyrrolidone, 5 g (40.6 mmol) of Cl-EC, and 4.9 ml (4.90 mmol) of tetrabutylammonium fluoride-THF solution (1 mol / l) were added and stirred using a syringe. The reaction was performed at a reaction temperature of 80 ° C., and the progress was analyzed using GC. The reaction was completed in 8 hours, and disappearance of the raw material peak was confirmed. After completion of the reaction, the reaction solution was reprecipitated with pure water, and the lower layer solution was collected. After collection, purification was performed by distillation, and F-EC was obtained as a fraction at 85 ° C. (100 mmHg) with a yield of 85% and a GC purity of 99.8%.
このＦ−ＥＣを19Ｆ−ＮＭＲ、1Ｈ−ＮＭＲ分析により分析し、４−フルオロ−１，３−ジオキソラン−２−オンであることを確認した。 This F-EC was analyzed by 19 F-NMR and 1 H-NMR analysis and confirmed to be 4-fluoro-1,3-dioxolan-2-one.
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