JP2661209B2 - Method for producing fluorine-containing silane compound - Google Patents
Method for producing fluorine-containing silane compoundInfo
- Publication number
- JP2661209B2 JP2661209B2 JP63285754A JP28575488A JP2661209B2 JP 2661209 B2 JP2661209 B2 JP 2661209B2 JP 63285754 A JP63285754 A JP 63285754A JP 28575488 A JP28575488 A JP 28575488A JP 2661209 B2 JP2661209 B2 JP 2661209B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- reaction
- compound represented
- represented
- compound
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 5
- 229910052731 fluorine Inorganic materials 0.000 title description 5
- 239000011737 fluorine Substances 0.000 title description 5
- -1 silane compound Chemical class 0.000 title description 5
- 229910000077 silane Inorganic materials 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- RRRXPPIDPYTNJG-UHFFFAOYSA-N perfluorooctanesulfonamide Chemical compound NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RRRXPPIDPYTNJG-UHFFFAOYSA-N 0.000 claims description 11
- 150000004703 alkoxides Chemical class 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- KRCZLPQTJDWPKN-UHFFFAOYSA-N tribromosilicon Chemical group Br[Si](Br)Br KRCZLPQTJDWPKN-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明はＮ−アルキル−Ｎ−（３−トリアルコキシシ
リルプロピル）ペルフルオロオクチルスルホンアミドの
製造方法に関する。The present invention relates to a method for producing N-alkyl-N- (3-trialkoxysilylpropyl) perfluorooctylsulfonamide.
一般式 C8F17SO2NR（CH2）3Si（OR′）３ （II） で表わされる含フッ素アルコキシシラン化合物は一般式
C8F17SO2NR（CH2）3SiX3 （Ｉ）で表わされる含フッ素
ハロゲノシラン化合物とメタノールあるいはエタノール
との反応によって得られるが、この時、反応で生じるハ
ロゲン化水素によって生成物の分解が生じるため、乾燥
窒素を吹き込むか、または減圧にすることによって生成
するハロゲン化水素を除去することが行われる。The fluorine-containing alkoxysilane compound represented by the general formula C 8 F 17 SO 2 NR (CH 2 ) 3 Si (OR ′) 3 (II) is represented by the general formula
C 8 F 17 SO 2 NR (CH 2 ) 3 SiX 3 (I) is obtained by reacting a fluorinated halogenosilane compound represented by the formula (I) with methanol or ethanol. Since decomposition occurs, removal of hydrogen halide generated by blowing dry nitrogen or reducing the pressure is performed.
しかし、この方法では完全にハロゲン化水素を除くた
めに長時間を要し、かつ生成する化合物が粘稠な液体で
あるため、ハロゲン化水素の脱離に伴って発泡し、その
ために反応器の容積を原料の容積の10倍以上にしなけれ
ばならない問題がある。However, in this method, it takes a long time to completely remove the hydrogen halide, and since the produced compound is a viscous liquid, it foams with the elimination of the hydrogen halide, and as a result, There is a problem that the volume must be at least 10 times the volume of the raw material.
本発明者らは上記の問題点を解決することを試み、一
般式（II）の含フッ素アルコキシシラン化合物を製造す
るには、一般式（Ｉ）で表わされる含フッ素ハロゲノシ
ラン化合物とメタノールあるいはエタノールを塩基の存
在で反応させるか、または一般式（III）で表わされる
金属アルコキシド、もしくは一般式（IV）で表わされる
オルトギ酸エステルを反応させることがより好適である
ことを見出した。The present inventors have attempted to solve the above problems, and to produce a fluorine-containing alkoxysilane compound of the general formula (II), a fluorine-containing halogenosilane compound represented by the general formula (I) and methanol or ethanol Was found to be more preferable in the presence of a base, or reacted with a metal alkoxide represented by the general formula (III) or an orthoformate represented by the general formula (IV).
本発明は、一般式 C8F17SO2NR（CH2）3SiX3 （Ｉ） （式中ＲはＣ１〜５のアルキル基、ＸはClまたはBrを表
わす）で表わされるＮ−アルキル−Ｎ−（３−トリハロ
ゲノシリルプロピル）ペルフルオロオクチルスルホンア
ミドとメタノールまたはエタノールとを塩基の存在下で
反応させることにより、 一般式 C8F17SO2NR（CH2）3Si（OR′）３ （II） （式中Ｒは前記と同じく、Ｒ′はCH3またはC2H5を表わ
す）で表わされるＮ−アルキル−Ｎ−（３−トリアルコ
キシシリルプロピル）ペルフルオロオクチルスルホンア
ミドを製造する方法を提供する。The present invention has the general formula C 8 F 17 SO 2 NR ( CH 2) 3 SiX 3 (I) ( the alkyl group of the formula R is C 1 to 5, X represents Cl or Br) N-alkyl represented by -N- by (3-tri-halogeno-silyl propyl) to the perfluorooctyl sulphonamide and methanol or ethanol in the presence of a base, the general formula C 8 F 17 SO 2 NR ( CH 2) 3 Si (oR ') 3 (II) (wherein R is as defined above, and R 'is CH 3 or C 2 H 5 ) to produce N-alkyl-N- (3-trialkoxysilylpropyl) perfluorooctylsulfonamide Provide a way.
また本発明は、一般式（Ｉ）で表わされる化合物と一
般式 Ｒ′OM （III） （式中Ｒ′は前記と同じく、Ｍはアルカリ金属を表わ
す）で表わされる金属アルコキシドとを反応させること
からなる一般式（II）で表わされる化合物の製造法を提
供する。Further, the present invention provides a method of reacting a compound represented by the general formula (I) with a metal alkoxide represented by the general formula R'OM (III) (wherein R 'is the same as above and M represents an alkali metal). A method for producing a compound represented by the general formula (II):
さらに、本発明は一般式（Ｉ）で表わされる化合物、
一般式 CH（OR′）３ （IV） （式中Ｒ′は前記と同じ）で表わされるオルトギ酸エス
テルとを反応させることからなる一般式（II）で表わさ
れる化合物の製造法を提供する。Further, the present invention provides a compound represented by the general formula (I):
A process for producing a compound represented by the general formula (II), comprising reacting an orthoformate represented by the general formula CH (OR ') 3 (IV) (wherein R' is the same as described above).
本発明の製造法において、一般式（Ｉ）の化合物とア
ルコールの反応は次式で示される。In the production method of the present invention, the reaction between the compound of the general formula (I) and the alcohol is represented by the following formula.
一般式（Ｉ）の化合物は 一般式（Ｖ） C8F17SO2NRCH2CH＝CH2 …（Ｖ） （式中Ｒは前記と同じ） で表わされる化合物と、一般式（VI）で表わされるトリ
ハロゲノシランとの反応 HSiX3 …（VI） （式中Ｘは前記と同じ） によって得られる。また反応に用いるメタノールまたは
エタノールは市販品を用いることができる。 The compound of the general formula (I) is a compound represented by the general formula (V) C 8 F 17 SO 2 NRCH 2 CH = CH 2 (wherein R is the same as described above) and a compound represented by the general formula (VI) Reaction with the represented trihalogenosilane HSiX 3 (VI) wherein X is as defined above. Commercially available methanol or ethanol can be used for the reaction.
一般式（II）で示される化合物の合成において、一般
式（Ｉ）で示される化合物と、メタノール、エタノール
との反応は、一般式（Ｉ）で示される化合物に対してメ
タノール、およびエタノールを３モル当量以上用いれば
よいが、好ましくは５ないし10モル当量用いることが推
奨される。この反応において塩基を存在させることが重
要であり、塩基としてはアミン類、特に三級アミンまた
は環式アミンが好適である。その使用量は一般式（Ｉ）
で表わされるトリハロゲノシラン化合物に対し３モル当
量以上であり、好ましくは５乃至10モル当量が推奨され
る。反応の温度範囲は０〜40℃、好ましくは10〜20℃で
ある。In the synthesis of the compound represented by the general formula (II), the reaction of the compound represented by the general formula (I) with methanol and ethanol is performed by reacting the compound represented by the general formula (I) with 3 It is sufficient to use at least a molar equivalent, but it is recommended to use 5 to 10 molar equivalents. It is important that a base is present in this reaction, and as the base, amines, particularly tertiary amines or cyclic amines, are suitable. The amount of use is represented by the general formula (I)
Is at least 3 molar equivalents, preferably 5 to 10 molar equivalents, based on the trihalogenosilane compound represented by The temperature range of the reaction is 0-40 ° C, preferably 10-20 ° C.
一方、一般式（Ｉ）で示される化合物と一般式（II
I）で示される金属アルコキシドとの反応は、次式のよ
うであって C8F17SO2NR（CH2）3SiX3＋3R′OM→ C8F17SO2NR（CH2）3Si（OR′）３＋3MX 一般式（Ｉ）で示される化合物に対して、一般式（II
I）で示される金属アルコキシドを３モル当量以上用い
ればよいが、好ましくは3.5ないし５モル当量用いる。
この場合も反応は０ないし40℃の温度範囲、好ましくは
10ないし20℃の温度範囲で行なう。この場合、反応速度
を高めるために溶媒としてメタノールあるいはエタノー
ルを用いることが好ましい。On the other hand, the compound represented by the general formula (I) and the compound represented by the general formula (II)
The reaction with the metal alkoxide represented by I) is as follows: C 8 F 17 SO 2 NR (CH 2 ) 3 SiX 3 + 3R′OM → C 8 F 17 SO 2 NR (CH 2 ) 3 Si (OR ') 3 + 3MX The compound represented by the general formula (I)
The metal alkoxide represented by I) may be used in an amount of at least 3 molar equivalents, preferably 3.5 to 5 molar equivalents.
Again, the reaction is carried out in a temperature range from 0 to 40 ° C., preferably
Perform in a temperature range of 10 to 20 ° C. In this case, it is preferable to use methanol or ethanol as a solvent in order to increase the reaction rate.
また一般式（Ｉ）の化合物と一般式（IV）で表わされ
るオルトギ酸エステルとの反応は、 C8F17SO2NR（CH2）3SiX3＋3HC（OR′）３→ C8F17SO2NR（CH2）3Si（OR′）３＋Ｒ′Ｘ＋3HCOOR′ で示される。一般式（Ｉ）の化合物に対し一般式（IV）
のオルトギ酸エステルを３モル当量以上、好ましくは５
〜10モル当量使用する。一般式（IV）のオルトギ酸エス
テルは市販品をそのまま用いてもよく、またトリハロゲ
ン化メタンとアルカリ金属アルコキシドとから次式の反
応で合成したものを適用してもよい。In addition, the reaction between the compound of the general formula (I) and the orthoformate represented by the general formula (IV) is performed as follows: C 8 F 17 SO 2 NR (CH 2 ) 3 SiX 3 + 3HC (OR ′) 3 → C 8 F 17 It is represented by SO 2 NR (CH 2 ) 3 Si (OR ′) 3 + R′X + 3HCOOR ′. Formula (IV) for the compound of Formula (I)
At least 3 molar equivalents, preferably 5
Use up to 10 molar equivalents. As the orthoformate of the general formula (IV), a commercially available product may be used as it is, or a product synthesized from a trihalogenated methane and an alkali metal alkoxide by the following reaction may be used.
CHX3＋3NaOR′→CH（OR′）３＋3NaX。CHX 3 + 3NaOR ′ → CH (OR ′) 3 + 3NaX.
上記反応は、室温から化合物から化合物（IV）の沸点
までの温度範囲で行なわれるが、好ましくは40℃ないし
80℃である。溶媒は一般式（IV）のオルトギ酸エステル
が液体であるため一般に必要としないが必要に応じて適
当な溶媒を用いてもよい。この反応は例えば塩化アルミ
ニウム等を触媒としてもよい。The above reaction is carried out in a temperature range from room temperature to the boiling point of the compound to the compound (IV), preferably from 40 ° C to
80 ° C. The solvent is not generally required since the orthoformate of the general formula (IV) is a liquid, but an appropriate solvent may be used if necessary. In this reaction, for example, aluminum chloride or the like may be used as a catalyst.
上記のいずれの反応においても、反応時間は反応温
度、反応剤によって変化するが、通常は２ないし12時間
で反応が終了する。反応の終点はガスクロマトグラフあ
るいは薄層クロマトグラフで容易に検出できる。反応終
了後、析出塩を濾別した後、または直接蒸留等の操作を
行うことによって生成物を単離できる。In any of the above reactions, the reaction time varies depending on the reaction temperature and the reactants, but the reaction is usually completed in 2 to 12 hours. The end point of the reaction can be easily detected by gas chromatography or thin-layer chromatography. After completion of the reaction, the product can be isolated by filtering off the precipitated salt or by performing an operation such as direct distillation.
本発明において共存するアミンまたは金属アルコキシ
ド中の金属イオンが反応時に生成する塩化水素と反応し
て塩を析出し、塩化水素を反応系内において効果的に除
去する働きをする。In the present invention, the coexisting amine or metal ion in the metal alkoxide reacts with hydrogen chloride generated during the reaction to precipitate a salt, and functions to effectively remove hydrogen chloride in the reaction system.
また、オルトギ酸エステルの反応では、塩化水素は発
生せず、これによる生成物の分解を防ぐと共に蒸留によ
り、副反応生成物を容易に除去できる。Further, in the reaction of the orthoformate, hydrogen chloride is not generated, thereby preventing decomposition of the product and easily removing by-products by distillation.
本発明の製造方法によれば、塩化水素が発生しても共
存するアミン又は金属アルコキシド中の金属イオンと反
応して直ちに除去されるので、短時間に効率よく上記含
フッ素アルコキシシラン化合物を製造することができ
る。According to the production method of the present invention, even if hydrogen chloride is generated, it reacts with the coexisting amine or metal ion in the metal alkoxide and is immediately removed, so that the fluorine-containing alkoxysilane compound is efficiently produced in a short time. be able to.
またオルトギ酸エステルを用いる反応では塩化水素が
発生しないので一層容易に上記含フッ素アルコキシシラ
ン化合物を製造できる。In addition, the reaction using an orthoformate does not generate hydrogen chloride, so that the above-mentioned fluorinated alkoxysilane compound can be produced more easily.
以下、本発明の実施例を示す。 Hereinafter, examples of the present invention will be described.
（実施例） 実施例１ 機械撹拌装置、温度計、還流器、滴下漏斗を備えた50
0ml三ッ口フラスコに、Ｎ−ｎ−プロピル−Ｎ−（３−
（トリクロロシリル）プロピル）ペルフルオロオクチル
スルホンアミド143.3g（0.20mol）を粉砕して入れ、つ
いでトリエチルアミン121.2g（1.2mol）を加え撹拌下氷
−水で外部冷却しながらメタノール96g（3.0mol）を15
〜20℃で２時間かけて滴下した。(Example) Example 1 50 equipped with a mechanical stirrer, a thermometer, a reflux condenser, and a dropping funnel.
In a 0 ml three-necked flask, Nn-propyl-N- (3-
143.3 g (0.20 mol) of (trichlorosilyl) propyl) perfluorooctylsulfonamide was pulverized and added, and then 121.2 g (1.2 mol) of triethylamine was added thereto.
It was added dropwise at 2020 ° C. over 2 hours.
滴下終了後生成した塩を濾別した後減圧蒸留により、
Ｎ−ｎ−プロピル−Ｎ−（３−（トリメトキシシリル）
プロピル）ペルフルオロオクチルスルホンアミド130.9g
（0.186mol）を得た。収率92.0％、沸点134℃/0.25mmHg
であった。After the completion of the dropping, the generated salt is separated by filtration and then distilled under reduced pressure.
Nn-propyl-N- (3- (trimethoxysilyl)
Propyl) perfluorooctyl sulfonamide 130.9g
(0.186 mol) was obtained. 92.0% yield, boiling point 134 ° C / 0.25mmHg
Met.
NMR分析、GC−MS分析、IR分析の結果より生成物が であることを確認した。Products are found from the results of NMR analysis, GC-MS analysis and IR analysis Was confirmed.
実施例２ 機械撹拌装置、還流器、滴下漏斗を備えた300ml三ッ
口フラスコに、Ｎ−ｎ−プロピル−Ｎ−（３−（トリク
ロロシリル）プロピル）ペルフルオロオクチルスルホン
アミド71.7g（0.10mol）を入れ、CH3ONaの78％メタノー
ル溶液75gを氷−水冷却下15〜20℃で２時間かけて滴下
した。Example 2 In a 300 ml three-necked flask equipped with a mechanical stirrer, a reflux condenser, and a dropping funnel, 71.7 g (0.10 mol) of Nn-propyl-N- (3- (trichlorosilyl) propyl) perfluorooctylsulfonamide was added. Then, 75 g of a 78% methanol solution of CH 3 ONa was added dropwise at 15 to 20 ° C. over 2 hours under ice-water cooling.
滴下終了後、生成した塩を濾別した後、減圧蒸留によ
りＮ−ｎ−プロピル−Ｎ−（３−（トリメトキシシリ
ル）プロピル）ペルフルオロオクチルスルホンアミド6
5.4g（0.093mol）を得た。収率93.0％であった。After completion of the dropwise addition, the resulting salt was filtered off, and then Nn-propyl-N- (3- (trimethoxysilyl) propyl) perfluorooctylsulfonamide 6 was distilled off under reduced pressure.
5.4 g (0.093 mol) were obtained. The yield was 93.0%.
実施例３ 機械撹拌装置、還流器を備えた300ml三ッ口フラスコ
に、Ｎ−ｎ−エチル−Ｎ−（３−（トリブロモシリル）
プロピル）ペルフルオロオクチルスルホンアミド83.6g
（0.10mol）、オルトギ酸エチル133.2g（0.9mol）、触
媒として塩化アルミニウム3.0gを入れ、80℃で12時間反
応させた。Example 3 Nn-ethyl-N- (3- (tribromosilyl) was placed in a 300 ml three-necked flask equipped with a mechanical stirrer and a reflux condenser.
Propyl) 83.6 g of perfluorooctylsulfonamide
(0.10 mol), 133.2 g (0.9 mol) of ethyl orthoformate and 3.0 g of aluminum chloride as a catalyst were reacted at 80 ° C. for 12 hours.
反応終了後、直接減圧蒸留を行うことによって、Ｎ−
ｎ−エチル−Ｎ−（３−（トリエトキシシリル）プロピ
ル）ペルフルオロオクチルスルホンアミド55.6g（0.076
mol）を得た。このものの収率76.1％、沸点146℃/0.18m
mHgであった。After completion of the reaction, N-
55.6 g (0.076) of n-ethyl-N- (3- (triethoxysilyl) propyl) perfluorooctylsulfonamide
mol). Yield 76.1%, boiling point 146 ° C / 0.18m
mHg.
Claims (3)
わす）で表わされるＮ−アルキル−Ｎ−（３−トリハロ
ゲノシリルプロピル）ペルフルオロオクチルスルホンア
ミドとメタノールまたはエタノールとを塩基の存在下で
反応させることにより、 一般式 C8F17SO2NR（CH2）3Si（OR′）３ （II） （式中Ｒは前記と同じく、Ｒ′はCH3またはC2H5を表わ
す）で表わされるＮ−アルキル−Ｎ−（３−トリアルコ
キシシリルプロピル）ペルフルオロオクチルスルホンア
ミドを製造する方法。1. An N-type compound represented by the general formula C 8 F 17 SO 2 NR (CH 2 ) 3 SiX 3 (I) wherein R represents a C 1-5 alkyl group and X represents Cl or Br. By reacting alkyl-N- (3-trihalogenosilylpropyl) perfluorooctylsulfonamide with methanol or ethanol in the presence of a base, a compound of the general formula C 8 F 17 SO 2 NR (CH 2 ) 3 Si (OR ′) ) 3 (II) (wherein R is as defined above, and R 'is CH 3 or C 2 H 5 ) to produce N-alkyl-N- (3-trialkoxysilylpropyl) perfluorooctylsulfonamide how to.
す）で表わされる金属アルコキシドとを反応させること
からなる一般式（II）で表わされる化合物の製造法。2. A reaction between a compound represented by the general formula (I) and a metal alkoxide represented by the general formula R'OM (III), wherein R 'is the same as above and M is an alkali metal. A method for producing a compound represented by the general formula (II):
テルとを反応させることからなる一般式（II）で表わさ
れる化合物の製造法。3. A method comprising reacting a compound represented by the general formula (I) with an orthoformate represented by the general formula CH (OR ') 3 (IV) wherein R' is the same as defined above. A method for producing a compound represented by the general formula (II).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63285754A JP2661209B2 (en) | 1988-11-14 | 1988-11-14 | Method for producing fluorine-containing silane compound |
| GB8909086A GB2218097A (en) | 1988-04-26 | 1989-04-21 | Perfluoroalkylsulphonamidoalkyl silanes; surface treatment agents |
| DE3913485A DE3913485A1 (en) | 1988-04-26 | 1989-04-24 | FLUOROUS SILVER COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| FR8905409A FR2630443A1 (en) | 1988-04-26 | 1989-04-24 | NOVEL FLUORINATED SILANES, PROCESSES FOR PREPARING SAME, WATER-REPELLENT AND WATER-REPELLENT AGENT CONTAINING THEM, AND VARIOUS MATERIALS TREATED OR CONTAINING AN INGREDIENT TREATED WITH THEM |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63285754A JP2661209B2 (en) | 1988-11-14 | 1988-11-14 | Method for producing fluorine-containing silane compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02134388A JPH02134388A (en) | 1990-05-23 |
| JP2661209B2 true JP2661209B2 (en) | 1997-10-08 |
Family
ID=17695617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63285754A Expired - Lifetime JP2661209B2 (en) | 1988-04-26 | 1988-11-14 | Method for producing fluorine-containing silane compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2661209B2 (en) |
-
1988
- 1988-11-14 JP JP63285754A patent/JP2661209B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02134388A (en) | 1990-05-23 |
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