JP2772465B2 - Production method of fluorine-containing silane compound by ultraviolet irradiation - Google Patents
Production method of fluorine-containing silane compound by ultraviolet irradiationInfo
- Publication number
- JP2772465B2 JP2772465B2 JP6258520A JP25852094A JP2772465B2 JP 2772465 B2 JP2772465 B2 JP 2772465B2 JP 6258520 A JP6258520 A JP 6258520A JP 25852094 A JP25852094 A JP 25852094A JP 2772465 B2 JP2772465 B2 JP 2772465B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- silane compound
- fluoroolefin
- containing silane
- producing
- 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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Description
【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION
【０００１】[0001]
【産業上の利用分野】本発明は、含フッ素シラン化合物
の製造法に関する。The present invention relates to a method for producing a fluorine-containing silane compound.
【０００２】[0002]
【従来の技術及びその問題点】含フッ素シラン化合物
は、熱安定性及び化学的安定性が高いため、例えば有機
フッ素化物の代替品として種々の分野への応用が考えら
れる。2. Description of the Related Art Fluorine-containing silane compounds have high thermal stability and chemical stability, and can be applied to various fields, for example, as substitutes for organic fluorinated compounds.
【０００３】含フッ素シラン化合物の製造法としては、
例えばヘキサフルオロプロペンとトリクロロシランの混
合物に60Coのγ線照射を行う方法が知られている (A.V.
Zimin ら、Dokl. Acad. Nauk SSSR, Ser Khim., 231, 8
70 (1976))。しかし、γ線照射による方法は、特殊な設
備を要する不利益がある。紫外線照射下でヘキサフルオ
ロプロペンとトリクロロシランとの反応では、対応する
含フッ素化合物は同定されておらず、生成されていたと
しても１％以下であり、実質的に生成しないという報告
がなされている (J. Am. Chem. Soc., 79, 2329 (195
7))。A method for producing a fluorine-containing silane compound includes the following:
For example, a method of irradiating a mixture of hexafluoropropene and trichlorosilane with γ-rays of 60 Co is known (AV
Zimin et al., Dokl. Acad. Nauk SSSR, Ser Khim., 231, 8
70 (1976)). However, the method using γ-ray irradiation has a disadvantage that special equipment is required. In the reaction between hexafluoropropene and trichlorosilane under ultraviolet irradiation, the corresponding fluorinated compound has not been identified, and even if it has been produced, it is reported to be 1% or less and substantially not produced. (J. Am. Chem. Soc., 79, 2329 (195
7)).
【０００４】含フッ素シラン化合物の他の製造例とし
て、テトラフルオロエチレンとトリクロロシランを紫外
線の存在下に反応させる方法が知られている (R.N.Hasz
eldineら、J. Chem. Soc., 962, (1956))。この文献で
は、Cl3Si(C2F4)nH（ｎは、１以上の整数）で表される
含フッ素シランについて、目的とするｎ＝１の生成物の
割合を高めるために、テトラフルオロエチレンに対して
大過剰のトリクロロシランを用いてバッチ式で反応させ
ている。その結果、混合物が得られ、モノ付加体の収率
は非常に低い。特に、トリクロロシランを基準としたモ
ノ付加体の収率は約１６％と低い。As another production example of a fluorine-containing silane compound, a method is known in which tetrafluoroethylene and trichlorosilane are reacted in the presence of ultraviolet rays (RNHasz
eldine et al., J. Chem. Soc., 962, (1956)). In this document, in order to increase the ratio of the desired product of n = 1, tetrafluorosilane was used for fluorine-containing silane represented by Cl 3 Si (C 2 F 4 ) n H (n is an integer of 1 or more). The reaction is carried out batchwise using a large excess of trichlorosilane relative to fluoroethylene. As a result, a mixture is obtained and the yield of monoadduct is very low. In particular, the yield of the monoadduct based on trichlorosilane is as low as about 16%.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、トリクロロ
シランまたはトリメチルシランにフルオロオレフィンモ
ノマーが付加した含フッ素シラン化合物を原料の無駄な
く、簡単且つ収率良く製造する方法を提供することを目
的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing a fluorine-containing silane compound in which a fluoroolefin monomer is added to trichlorosilane or trimethylsilane without waste of raw materials and in a simple and high yield. I do.
【０００６】[0006]
【課題を解決するための手段】本発明者は、上記従来技
術に鑑み鋭意検討を重ねた結果、トリクロロシランを含
む反応系内にフルオロオレフィンを導入することによ
り、テロマー化が抑制され、フルオロオレフィンのモノ
マーとトリクロロシランが反応した含フッ素シラン化合
物が容易に得られることを見出した。また、従来反応が
進行しないと考えられていた、紫外線照射下でのヘキサ
フルオロプロペンとトリクロロシランの反応が、一定の
波長の紫外線を用いることにより進行することを見出し
た。Means for Solving the Problems As a result of intensive studies in view of the above prior art, the present inventors have found that by introducing fluoroolefin into a reaction system containing trichlorosilane, telomerization is suppressed and fluoroolefin is suppressed. It has been found that a fluorine-containing silane compound obtained by reacting the above monomer with trichlorosilane can be easily obtained. Further, they have found that the reaction between hexafluoropropene and trichlorosilane under irradiation of ultraviolet light, which was conventionally considered not to progress, proceeds by using ultraviolet light of a certain wavelength.
【０００７】すなわち、本発明は、以下の含フッ素シラ
ン化合物の製造法を提供するものである。That is, the present invention provides the following process for producing a fluorine-containing silane compound.
【０００８】[0008]
【０００９】[0009]
【００１０】[0010]
【００１１】項１． 紫外線照射下にトリメチルシラン
と一般式（１）Item 1 . Trimethylsilane and general formula ( 1 ) under UV irradiation
【００１２】[0012]
【化２】ＣＸ1Ｘ2＝ＣＸ3−Ｒf （１） 〔式中、Ｘ1、Ｘ2及びＸ3は、同一又は異なって水素原
子又はフッ素原子を示す。Ｒfは炭素数１〜８のパーフ
ルオロアルキル基を示す。〕のフルオロアルケンを反応
させることを特徴とするフルオロアルキルトリメチルシ
ランの製造法。## STR2 ## CX 1 X 2 = CX 3 -R f (1) wherein, X 1, X 2 and X 3 represents a hydrogen atom or a fluorine atom identical or different. R f represents a perfluoroalkyl group having 1 to 8 carbon atoms. A process for producing a fluoroalkyltrimethylsilane.
【００１３】項２． 一般式（１）のフルオロアルケン
がヘキサフルオロプロペンである項１に記載の製造法。Item 2 . Item 2. The production method according to Item 1 , wherein the fluoroalkene of the general formula (1) is hexafluoropropene.
【００１４】項３． 紫外線照射下にトリクロロシラン
またはトリメチルシランを含む反応系内にクロロフルオ
ロオレフィン又はフルオロオレフィンを連続的もしくは
間欠的に導入することを特徴とする含フッ素シラン化合
物の製造法。Item 3 . A method for producing a fluorinated silane compound, comprising continuously or intermittently introducing chlorofluoroolefin or fluoroolefin into a reaction system containing trichlorosilane or trimethylsilane under ultraviolet irradiation.
【００１５】項４． 紫外線照射下にトリクロロシラン
またはトリメチルシランを含む反応系内にフルオロオレ
フィンを連続的もしくは間欠的に導入することを特徴と
する含フッ素シラン化合物の製造法。Item 4 . A process for producing a fluorine-containing silane compound, which comprises continuously or intermittently introducing a fluoroolefin into a reaction system containing trichlorosilane or trimethylsilane under ultraviolet irradiation.
【００１６】項５． フルオロオレフィンがヘキサフル
オロプロペン、テトラフルオロエチレン、トリフルオロ
エチレン、１，１，３，３，３−ペンタフルオロプロピ
レン及びヘプタフルオロプロピルトリフルオロビニルエ
ーテルからなる群から選ばれるいずれか１種である項４
に記載の含フッ素シラン化合物の製造法。Item 5 . Item 4 in which the fluoroolefin is any one selected from the group consisting of hexafluoropropene, tetrafluoroethylene, trifluoroethylene, 1,1,3,3,3-pentafluoropropylene and heptafluoropropyltrifluorovinyl ether
3. The method for producing a fluorine-containing silane compound according to item 1.
【００１７】項６． クロロフルオロオレフィン又はフ
ルオロオレフィンを連続的に導入することを特徴とする
項３に記載の含フッ素シラン化合物の製造法。Item 6 . Item 4. The process for producing a fluorinated silane compound according to Item 3 , wherein chlorofluoroolefin or fluoroolefin is continuously introduced.
【００１８】一般式（１）の化合物において、Ｒfは、
トリフルオロメチル、ペンタフルオロエチル、パーフル
オロ−ｎ−プロピル、パーフルオロイソプロピル、パー
フルオロ−ｎ−ブチル、パーフルオロイソブチル、パー
フルオロ−ｔ−ブチル、パーフルオロペンチル、パーフ
ルオロヘキシル、パーフルオロヘプチル、パーフルオロ
オクチルなどの直鎖又は分枝を有する炭素数１〜８のパ
ーフルオロアルキル基、好ましくは炭素数１〜４のパー
フルオロアルキル基が挙げられる。In the compound of the general formula (1) , R f is
Trifluoromethyl, pentafluoroethyl, perfluoro-n-propyl, perfluoroisopropyl, perfluoro-n-butyl, perfluoroisobutyl, perfluoro-t-butyl, perfluoropentyl, perfluorohexyl, perfluoroheptyl, par Examples thereof include a linear or branched perfluoroalkyl group having 1 to 8 carbon atoms, such as fluorooctyl, and preferably a perfluoroalkyl group having 1 to 4 carbon atoms.
【００１９】本発明の製造法で使用する「フルオロオレ
フィン」として、例えばモノフルオロエチレン、ジフル
オロエチレン、トリフルオロエチレン、テトラフルオロ
エチレンなどのフルオロエチレン類、ヘキサフルオロプ
ロピレン、１，１，３，３，３−ペンタフルオロプロピ
レンなどのフルオロプロピレン類、オクタフルオロ２−
ブテンなどのブテン類、ヘプタフルオロプロピルトリフ
ルオロビニルエーテル、などのフルオロビニルエーテル
類、ヘキサフルオロシクロブテンなどのシクロブテン類
などが挙げられ、好ましいフルオロオレフィンとしてヘ
キサフルオロプロペン、テトラフルオロエチレン、トリ
フルオロエチレン、１，１，３，３，３−ペンタフルオ
ロプロピレン及びヘプタフルオロプロピルトリフルオロ
ビニルエーテルなどが挙げられる。The "fluoroolefin" used in the production method of the present invention includes, for example, fluoroethylenes such as monofluoroethylene, difluoroethylene, trifluoroethylene and tetrafluoroethylene, hexafluoropropylene, 1,1,3,3 and Fluoropropylenes such as 3-pentafluoropropylene, octafluoro-2-
Butenes such as butene, fluorovinyl ethers such as heptafluoropropyltrifluorovinyl ether, and cyclobutenes such as hexafluorocyclobutene, and the like, and preferred fluoroolefins such as hexafluoropropene, tetrafluoroethylene, trifluoroethylene, and 1, 1,3,3,3-pentafluoropropylene and heptafluoropropyl trifluorovinyl ether.
【００２０】本発明の製造法で使用する「クロロフルオ
ロオレフィン」として、クロロトリフルオロエチレン、
２−クロロ−１，１−ジフルオロエチレン、１，２−ジ
クロロ−１，２−ジフルオロエチレン、１，１−ジクロ
ロ−２，２−ジフルオロエチレン、２−クロロ−１，
３，３，３−テトラフルオロプロペン等が挙げられ、好
ましくは、クロロトリフルオロエチレン、１，２−ジク
ロロ−１，２−ジフルオロエチレン、２−クロロ−１，
３，３，３−テトラフルオロプロペン等が例示される。As the "chlorofluoroolefin" used in the production method of the present invention, chlorotrifluoroethylene,
2-chloro-1,1-difluoroethylene, 1,2-dichloro-1,2-difluoroethylene, 1,1-dichloro-2,2-difluoroethylene, 2-chloro-1,
3,3,3-tetrafluoropropene and the like, preferably chlorotrifluoroethylene, 1,2-dichloro-1,2-difluoroethylene, 2-chloro-1,
3,3,3-tetrafluoropropene and the like are exemplified.
【００２１】本発明で製造される「含フッ素シラン化合
物」は、トリクロロシランにフルオロオレフィンモノマ
ーまたはクロロフルオロオレフィンモノマーが付加した
化合物を意味する。The "fluorinated silane compound" produced in the present invention means a compound obtained by adding a fluoroolefin monomer or a chlorofluoroolefin monomer to trichlorosilane.
【００２２】本発明の製造法で、フルオロオレフィン又
はクロロフルオロオレフィン（以下、フルオロオレフィ
ン類という）を「連続的もしくは間欠的に導入する」と
は、反応系内におけるフルオロオレフィン類濃度をモニ
ターし、フルオロオレフィン類の濃度が所定の範囲内に
入るようにフルオロオレフィン類を連続的に又は間欠的
に導入することを意味する。フルオロオレフィン類は連
続的に供給する方が、該濃度をより狭い範囲内に保つこ
とができるため好ましい。トリクロロシランが大部分消
費された後には、フルオロオレフィンの導入によりその
比率が高まることになるが、これはテロマー化にほとん
ど影響しない。In the production method of the present invention, "continuously or intermittently introducing a fluoroolefin or a chlorofluoroolefin" (hereinafter referred to as "fluoroolefins") means that the concentration of the fluoroolefins in the reaction system is monitored. This means that the fluoroolefins are introduced continuously or intermittently so that the concentration of the fluoroolefins falls within a predetermined range. It is preferable to continuously supply the fluoroolefins because the concentration can be kept within a narrower range. After most of the trichlorosilane has been consumed, the introduction of the fluoroolefin will increase the proportion, but this will have little effect on telomerization.
【００２３】本発明の製造法は、特に限定されないが、
１モルのトリクロロシランに対し、フルオロオレフィン
を最終的に１〜１．５モル程度使用する。反応容器に
は、通常トリクロロシランのみが入っているが、テロマ
ー化の影響が問題でない限り、フルオロオレフィンを含
んでいてもよい。反応開始時に含まれるフルオロオレフ
ィンの量は、特に限定されないが、例えばトリクロロシ
ランの５０モル％程度以下、好ましくは２０モル％以
下、より好ましくは１０モル％以下である。Although the production method of the present invention is not particularly limited,
The fluoroolefin is used in an amount of about 1 to 1.5 moles per 1 mole of trichlorosilane. The reaction vessel usually contains only trichlorosilane, but may contain a fluoroolefin as long as the effect of telomerization is not a problem. The amount of the fluoroolefin contained at the start of the reaction is not particularly limited, but is, for example, about 50 mol% or less of trichlorosilane, preferably 20 mol% or less, and more preferably 10 mol% or less.
【００２４】反応系内へのフルオロオレフィンの導入
は、反応系内のフルオロオレフィンの量が、トリクロロ
シランの０．０１〜５０モル％程度、好ましくは０．１
〜２０モル％程度になるように行う。但しこれらの範囲
は、未反応のトリクロロシランが十分に残っている場合
に適用されるもので、未反応のトリクロロシランが残り
少なくなった場合には、フルオロオレフィンの割合が上
記の範囲を超えても差し支えない。The introduction of the fluoroolefin into the reaction system is carried out when the amount of the fluoroolefin in the reaction system is about 0.01 to 50 mol% of trichlorosilane, preferably 0.1 to 50 mol%.
It is performed so as to be about 20 mol%. However, these ranges are applied when the unreacted trichlorosilane remains sufficiently, and when the unreacted trichlorosilane decreases, the ratio of the fluoroolefin may exceed the above range. No problem.
【００２５】本発明の方法で使用される紫外線の波長
は、通常１００〜３９０ｎｍ程度、好ましくは１７０〜
３７０ｎｍ程度である。The wavelength of the ultraviolet light used in the method of the present invention is usually about 100 to 390 nm, preferably 170 to 390 nm.
It is about 370 nm.
【００２６】紫外線の光源は、特に限定されないが、例
えば低圧水銀灯、超高圧水銀灯、高圧水銀灯、重水素放
電管、キセノン放電管、ルビーレーザーやＹＡＧレーザ
ーの高調波、エキシマレーザー、色素レーザーなどが挙
げられ、好ましくは低圧水銀灯による３７０ｎｍ以下の
波長の光が用いられる。The ultraviolet light source is not particularly limited, and examples thereof include a low-pressure mercury lamp, an ultra-high-pressure mercury lamp, a high-pressure mercury lamp, a deuterium discharge tube, a xenon discharge tube, a harmonic of a ruby laser and a YAG laser, an excimer laser, and a dye laser. Preferably, light having a wavelength of 370 nm or less from a low-pressure mercury lamp is used.
【００２７】反応温度は、通常室温で十分に反応する
が、温度が高くても問題はない。The reaction temperature is usually sufficient at room temperature, but there is no problem even if the temperature is high.
【００２８】紫外線の照射方法は、外部照射法、内部照
射法のいずれでもよいが、外部照射法の場合には、反応
容器の材質は石英ガラスが望ましい。反応圧力は、特に
制限されるものではなく、減圧から加圧までのいずれの
圧力下でも反応は進行する。反応時間は、出発原料の使
用量、紫外線ランプの種類や能力により異なり一概には
言えないが、数時間から数百時間で反応はほとんど完結
する。The method of irradiating the ultraviolet rays may be either an external irradiation method or an internal irradiation method. In the case of the external irradiation method, the material of the reaction vessel is desirably quartz glass. The reaction pressure is not particularly limited, and the reaction proceeds under any pressure from reduced pressure to increased pressure. The reaction time varies depending on the amount of the starting material used, the type and the capacity of the ultraviolet lamp, and cannot be determined unconditionally. However, the reaction is almost completed within several hours to several hundred hours.
【００２９】本発明で製造される含フッ素シラン化合物
は、溶媒、シランカップリング剤、表面処理剤、離型
剤、繊維処理剤、消泡剤、シリコーン油、シリコーング
リース及びシリコーンゴムなどの製造中間体として有用
である。The fluorine-containing silane compound produced in the present invention is used for the production of solvents, silane coupling agents, surface treatment agents, release agents, fiber treatment agents, defoamers, silicone oils, silicone greases and silicone rubbers. Useful as a body.
【００３０】[0030]
【発明の効果】本発明によれば、紫外線照射下にフルオ
ロオレフィンを連続供給することで、種々の含フッ素シ
ラン化合物を簡便に且つ高収率で製造することができ
る。According to the present invention, various fluorinated silane compounds can be easily produced at a high yield by continuously supplying a fluoroolefin under ultraviolet irradiation.
【００３１】[0031]
【実施例】以下に、実施例を挙げて本発明をより一層明
らかにする。The present invention will be further clarified with reference to the following examples.
【００３２】実施例１ 350mlの石英管反応容器中に、100.0gトリクロロシラン
を入れ、該容器を液体窒素で冷却しながら真空ラインで
減圧にし、空気を除去した。２個の１５Ｗ用低圧水銀灯
（大科工業（株）製）を用いてその容器に紫外線を外部
照射し、全量110.7gのヘキサフルオロプロピレンを2.46
ml／分の速度で容器内圧を2.0kg/cm2以下になるように
１２０時間かけて徐々に加えた。室温で１８９時間後反
応を終了した。反応溶液のＧＣ分析から、ヘキサフルオ
ロプロピルトリクロロシランがＧＣ純度８３％で生成し
た。ＮＭＲの積分比より、α体：β体は、36:64であっ
た。Example 1 A 350 ml quartz tube reaction vessel was charged with 100.0 g of trichlorosilane, and the vessel was evacuated with a vacuum line while cooling with liquid nitrogen to remove air. The container was externally irradiated with ultraviolet light using two low-pressure mercury lamps for 15 W (manufactured by Daishin Kogyo Co., Ltd.), and a total amount of 110.7 g of hexafluoropropylene was 2.46.
The pressure in the container was gradually increased at a rate of ml / min over 120 hours such that the internal pressure of the container became 2.0 kg / cm 2 or less. After 189 hours at room temperature, the reaction was terminated. From the GC analysis of the reaction solution, hexafluoropropyltrichlorosilane was produced with a GC purity of 83%. From the NMR integration ratio, the ratio of α-form: β-form was 36:64.
【００３３】なお、α体は、Cl3SiCF2CFHCF3であり、β
体はCl3SiCFCF3CF2Hであった。生成物は、1H-NMR、19F-
NMRより同定した。The α-form is Cl 3 SiCF 2 CFHCF 3 and β-form
The body was Cl 3 SiCFCF 3 CF 2 H. The product was 1 H-NMR, 19 F-
It was identified by NMR.
【００３４】実施例２ 200mlの石英管反応容器中に、0.185モルのトリクロロシ
ランを入れ、該容器を液体窒素で冷却しながら真空ライ
ンで減圧にし、空気を除去した。１個の１５Ｗ用低圧水
銀灯（大科工業（株）製）を用いてその容器に紫外線を
外部照射し、全量0.185モルのテトラフルオロエチレン
を1.03ml／分の速度で容器内圧を2.0kg/cm2以下になる
ように７２時間かけて徐々に加えた。テトラフルオロエ
チレンの供給が終了した時点で反応を終了したところ、
テトラフルオロエチルトリクロロシランがＧＣ収率５６
％で生成した。単付加体：２付加体：３付加体は、92:
7:1であった。生成物は、ＧＣ−ＭＳ、1H-NMR、19F-NMR
より同定した。Example 2 0.185 mol of trichlorosilane was placed in a 200 ml quartz tube reaction vessel, and the vessel was evacuated with a vacuum line while cooling with liquid nitrogen to remove air. Using a single 15 W low-pressure mercury lamp (manufactured by Daika Kogyo Co., Ltd.), the container is externally irradiated with ultraviolet light, and the total pressure of the container is 2.0 kg / cm at a rate of 1.03 ml / min. The solution was gradually added over 72 hours so that the amount became 2 or less. When the reaction was terminated when the supply of tetrafluoroethylene was terminated,
Tetrafluoroethyltrichlorosilane has a GC yield of 56
%. Single adduct: 2 adduct: 3 adduct is 92:
7: 1. The product was analyzed by GC-MS, 1 H-NMR, 19 F-NMR
More identified.
【００３５】実施例３ 反応温度を４０℃とした以外は、実施例２と同様にして
反応を行い、テトラフルオロエチルトリクロロシランが
ＧＣ収率５９％で生成した。単付加体：２付加体：３付
加体は、89:9:1であった。生成物は、ＧＣ−ＭＳ、1H-N
MR、19F-NMRより同定した。Example 3 A reaction was carried out in the same manner as in Example 2 except that the reaction temperature was changed to 40 ° C., and tetrafluoroethyltrichlorosilane was produced with a GC yield of 59%. The single adduct: 2 adduct: 3 adduct was 89: 9: 1. The product was GC-MS, 1 HN
It was identified from MR and 19 F-NMR.
【００３６】実施例４ トリクロロシランの代わりにトリメチルシランを０．３
モル使用し、ヘキサフルオロプロピレンの０．３モル量
を５４時間かけて加え、反応時間を９０時間とした以外
は実施例１と同様にして反応を行った。反応溶液のＧＣ
分析から、ヘキサフルオロプロピルトリメチルシランが
ＧＣ純度８７％で生成した。α体：β体は、87:13であ
った。Example 4 0.3 g of trimethylsilane was used instead of trichlorosilane.
The reaction was carried out in the same manner as in Example 1 except that 0.3 mol of hexafluoropropylene was added over 54 hours, and the reaction time was changed to 90 hours. GC of reaction solution
From the analysis, hexafluoropropyltrimethylsilane was formed with a GC purity of 87%. The ratio of α-form: β-form was 87:13.
【００３７】なお、α体は、(CH3)3SiCF2CFHCF3であ
り、β体は(CH3)3SiCFCF3CF2Hであった。生成物は、1H-
NMR、19F-NMRより同定した。The α-form was (CH 3 ) 3 SiCF 2 CFHCF 3 and the β-form was (CH 3 ) 3 SiCFCF 3 CF 2 H. The product is 1 H-
It was identified by NMR and 19 F-NMR.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 関屋 章 茨城県つくば市東１丁目１番 工業技術 院物質工学工業技術研究所内 (72)発明者 小林 勉 東京都文京区本郷２−40−17 本郷若井 ビル 財団法人地球環境産業技術研究機 構内 (72)発明者 星 信人 東京都文京区本郷２−40−17 本郷若井 ビル 財団法人地球環境産業技術研究機 構内 審査官 大久保 元浩 (56)参考文献 Ｊ．ＡＭ．ＣＨＥＭ．ＳＯＣ．，79 （1957） Ｐ．2329−2332 （米) (58)調査した分野(Int.Cl.6，ＤＢ名) C07F 7/12────────────────────────────────────────────────── ─── Continued on the front page (72) Inventor Akira Sekiya 1-1-1 Higashi, Tsukuba, Ibaraki Pref., National Institute of Advanced Industrial Science and Technology (72) Inventor Tsutomu Kobayashi 2-40-17 Hongo, Hongo 2-17 Hongo, Bunkyo-ku, Tokyo Building Building for Global Environmental Technology Research (72) Inventor Nobuhito Hoshi 2-40-17 Hongo, Bunkyo-ku, Tokyo Hongo Wakai Building Examiner, Motohiro Okubo (56) Reference J. AM. CHEM. SOC. , 79 (1957) p. 2329-2332 (US) (58) Field surveyed (Int. Cl. 6 , DB name) C07F 7/12
Claims (6)
（１） 【化１】ＣＸ1Ｘ2＝ＣＸ3−Ｒf （１） 〔式中、Ｘ1、Ｘ2及びＸ3は、同一又は異なって水素原
子又はフッ素原子を示す。Ｒfは炭素数１〜８のパーフ
ルオロアルキル基を示す。〕のフルオロアルケンを反応
させることを特徴とするフルオロアルキルトリメチルシ
ランの製造法。( 1 ) Under irradiation of ultraviolet light, trimethylsilane and a compound represented by the general formula ( 1 ): CX 1 X 2 = CX 3 -R f ( 1 ) wherein X 1 , X 2 and X 3 are the same or A hydrogen atom or a fluorine atom is shown differently. R f represents a perfluoroalkyl group having 1 to 8 carbon atoms. A process for producing a fluoroalkyltrimethylsilane.
フルオロプロペンである請求項１に記載の製造法。2. A process according to claim 1 fluoroalkene is hexafluoropropene of general formula (1).
リメチルシランを含む反応系内にクロロフルオロオレフ
ィン又はフルオロオレフィンを連続的もしくは間欠的に
導入することを特徴とする含フッ素シラン化合物の製造
法。3. A process for producing a fluorine-containing silane compound, which comprises continuously or intermittently introducing chlorofluoroolefin or fluoroolefin into a reaction system containing trichlorosilane or trimethylsilane under irradiation with ultraviolet rays.
リメチルシランを含む反応系内にフルオロオレフィンを
連続的もしくは間欠的に導入することを特徴とする含フ
ッ素シラン化合物の製造法。4. A process for producing a fluorine-containing silane compound, which comprises continuously or intermittently introducing a fluoroolefin into a reaction system containing trichlorosilane or trimethylsilane under ultraviolet irradiation.
ペン、テトラフルオロエチレン、トリフルオロエチレ
ン、１，１，３，３，３−ペンタフルオロプロピレン及
びヘプタフルオロプロピルトリフルオロビニルエーテル
からなる群から選ばれるいずれか１種である請求項４に
記載の含フッ素シラン化合物の製造法。5. The fluoroolefin is one selected from the group consisting of hexafluoropropene, tetrafluoroethylene, trifluoroethylene, 1,1,3,3,3-pentafluoropropylene and heptafluoropropyltrifluorovinyl ether. The method for producing a fluorine-containing silane compound according to claim 4 , wherein
レフィンを連続的に導入することを特徴とする請求項３
に記載の含フッ素シラン化合物の製造法。6. The method of claim 3, wherein the introduction of chloro fluoroolefin or fluoroolefins continuously
3. The method for producing a fluorine-containing silane compound according to item 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6258520A JP2772465B2 (en) | 1994-10-24 | 1994-10-24 | Production method of fluorine-containing silane compound by ultraviolet irradiation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6258520A JP2772465B2 (en) | 1994-10-24 | 1994-10-24 | Production method of fluorine-containing silane compound by ultraviolet irradiation |
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| Publication Number | Publication Date |
|---|---|
| JPH08119979A JPH08119979A (en) | 1996-05-14 |
| JP2772465B2 true JP2772465B2 (en) | 1998-07-02 |
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ID=17321358
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| Application Number | Title | Priority Date | Filing Date |
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| JP6258520A Expired - Lifetime JP2772465B2 (en) | 1994-10-24 | 1994-10-24 | Production method of fluorine-containing silane compound by ultraviolet irradiation |
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Non-Patent Citations (1)
| Title |
|---|
| Ｊ．ＡＭ．ＣＨＥＭ．ＳＯＣ．，７９ （１９５７） Ｐ．２３２９−２３３２ （米） |
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|---|---|
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