JPH0673070A - Production of organosilicon compound - Google Patents
Production of organosilicon compoundInfo
- Publication number
- JPH0673070A JPH0673070A JP4232259A JP23225992A JPH0673070A JP H0673070 A JPH0673070 A JP H0673070A JP 4232259 A JP4232259 A JP 4232259A JP 23225992 A JP23225992 A JP 23225992A JP H0673070 A JPH0673070 A JP H0673070A
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbon group
- organosilicon compound
- tertiary hydrocarbon
- present
- grignard reagent
- 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.)
- Pending
Links
- 150000003961 organosilicon compounds Chemical class 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 25
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 14
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 14
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 abstract description 12
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- UTYRQCFTOYUATF-UHFFFAOYSA-N tert-butyl(chloro)silane Chemical compound CC(C)(C)[SiH2]Cl UTYRQCFTOYUATF-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- BQGIGVBLZYZDQL-UHFFFAOYSA-N chloro(2-methylbutan-2-yl)silane Chemical compound CCC(C)(C)[SiH2]Cl BQGIGVBLZYZDQL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ADUIJCXXHQETOK-UHFFFAOYSA-N C(C)C([SiH2]Cl)(CC)CC Chemical compound C(C)C([SiH2]Cl)(CC)CC ADUIJCXXHQETOK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- DBPHPBLAKVZXOY-UHFFFAOYSA-N Tetrahydro-2-methyl-3-furanthiol Chemical compound CC1OCCC1S DBPHPBLAKVZXOY-UHFFFAOYSA-N 0.000 description 1
- DXANINMRVVXDTI-UHFFFAOYSA-M [Br-].CCC([Mg+])(CC)CC Chemical compound [Br-].CCC([Mg+])(CC)CC DXANINMRVVXDTI-UHFFFAOYSA-M 0.000 description 1
- ZKLZTSWQZPJQCB-UHFFFAOYSA-M [Cl-].CCC([Mg+])(CC)CC Chemical compound [Cl-].CCC([Mg+])(CC)CC ZKLZTSWQZPJQCB-UHFFFAOYSA-M 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HZZOEADXZLYIHG-UHFFFAOYSA-N magnesiomagnesium Chemical compound [Mg][Mg] HZZOEADXZLYIHG-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FKKWHMOEKFXMPU-UHFFFAOYSA-M magnesium;2-methylbutane;chloride Chemical compound [Mg+2].[Cl-].CC[C-](C)C FKKWHMOEKFXMPU-UHFFFAOYSA-M 0.000 description 1
- UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical compound [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は一般式ＲＳｉＨ2 Ｃｌ
（式中、Ｒは第３級炭化水素基である。以下同じ）で示
される第３級炭化水素基を有する有機ケイ素化合物の製
造方法に関するものである。そして、この有機ケイ素化
合物はシランカップリング剤、シリル化剤及び他の有機
ケイ素化合物（例えばオルガノトリアルコキシシラン）
製造の原料等として工業的に有用である。FIELD OF THE INVENTION The present invention is of general formula RSiH 2 Cl.
(In the formula, R is a tertiary hydrocarbon group. The same applies hereinafter.) The present invention relates to a method for producing an organosilicon compound having a tertiary hydrocarbon group. This organosilicon compound is a silane coupling agent, a silylating agent and other organosilicon compounds (eg organotrialkoxysilane).
It is industrially useful as a raw material for production.
【０００２】[0002]
【従来の技術】第３級炭化水素基を有するケイ素化合物
の合成方法としては、（１）グリニヤール試薬を用いる
方法、（２）有機リチウムを利用する方法等が知られて
いる。As a method for synthesizing a silicon compound having a tertiary hydrocarbon group, (1) a method using a Grignard reagent and (2) a method using an organic lithium are known.
【０００３】（１）グリニヤール試薬を用いる方法とし
ては、特公昭６３−４８２７４号公報にグリニヤール試
薬とトリクロロシラン又は炭化水素基含有ハロゲン化シ
ランとの反応が開示されている。しかしながら、この方
法で得られる反応生成物には、ハロゲン原子が２個以上
存在するか、あるいは第３級炭化水素基以外の炭化水素
基が存在することになり、一般式ＲＳｉＨ2 Ｃｌで示さ
れる有機ケイ素化合物は得られない。又、特開平３−３
１２９０号公報にもグリニヤール試薬と炭化水素基含有
ハロゲン化シランとの反応が開示されているが、やはり
一般式ＲＳｉＨ 2 Ｃｌに相当するものは得られない。(1) A method using a Grignard reagent
For example, in Japanese Examined Patent Publication No. 63-48274, the Grignard trial
Drug and trichlorosilane or hydrocarbon group containing hydrocarbon group
Reactions with orchids are disclosed. However, this person
The reaction product obtained by the method contains two or more halogen atoms.
Hydrocarbons that are present or other than tertiary hydrocarbon radicals
Group is present, the general formula RSiH2Indicated by Cl
No organosilicon compound is obtained. Moreover, JP-A-3-3
No. 1290 also contains a Grignard reagent and a hydrocarbon group.
Although reaction with halogenated silanes is disclosed,
General formula RSiH 2No equivalent to Cl is obtained.
【０００４】（２）有機リチウムを利用する方法として
は第３級アルキルリチウムとクロロシラン類を反応させ
る方法が知られているが、この方法は高活性なリチウム
を使用するため特殊な設備を必要とすること、又第３級
アルキルリチウムは空気と接触すると発火する性質があ
り大量に使用する場合には危険度が高いこと等の問題点
を有している。(2) As a method of utilizing organic lithium, a method of reacting a tertiary alkyllithium with chlorosilanes is known, but this method requires special equipment because highly active lithium is used. In addition, the tertiary alkyllithium has a problem that it has a property of igniting when it comes into contact with air and is highly dangerous when used in a large amount.
【０００５】[0005]
【発明が解決しようする課題】本発明は上記のように従
来技術では製造することが困難であった第３級炭化水素
基を有する有機ケイ素化合物を容易かつ収率よく製造す
る方法を提供するものである。DISCLOSURE OF THE INVENTION The present invention provides a method for easily and efficiently producing an organosilicon compound having a tertiary hydrocarbon group, which has been difficult to produce by the prior art as described above. Is.
【０００６】[0006]
【課題を解決するための手段】本発明者らは近年工業的
に製造されるようになったジクロルシランの反応性につ
いて鋭意研究した結果、ケイ素原子に結合している２つ
の水素原子による立体的及び電子的効果等によって、グ
リニヤール試薬中の嵩高い炭化水素基とケイ素の結合反
応が速やかに起こることを見出し、本発明を完成するに
至った。As a result of diligent research on the reactivity of dichlorosilane, which has been industrially produced in recent years, the inventors of the present invention have found that the steric and steric properties of two hydrogen atoms bonded to a silicon atom are high. The inventors have found that a binding reaction between a bulky hydrocarbon group in a Grignard reagent and silicon occurs rapidly due to an electronic effect or the like, and have completed the present invention.
【０００７】すなわち本発明は、一般式ＲＭｇＸ（式
中、Ｒは第３級炭化水素基、Ｘはハロゲン原子である。
以下同じ）で示されるグリニヤール試薬とジクロルシラ
ンを反応させて、一般式ＲＳｉＨ2 Ｃｌで示される第３
級炭化水素基を有する有機ケイ素化合物を製造する方法
である。That is, according to the present invention, R is a tertiary hydrocarbon group and X is a halogen atom in the general formula RMgX.
The same shall apply hereinafter) and a Grignard reagent represented by the general formula RSiH 2 Cl
A method for producing an organosilicon compound having a primary hydrocarbon group.
【０００８】本発明においては、ジクロルシランと一般
式ＲＭｇＸで示されるグリニヤール試薬とが工業的に好
ましい穏やかな条件下でも速やかに反応して、第３級炭
化水素基を有する有機ケイ素化合物が容易に得られる。In the present invention, the dichlorosilane and the Grignard reagent represented by the general formula RMgX react rapidly under industrially preferable mild conditions to easily obtain an organosilicon compound having a tertiary hydrocarbon group. To be
【０００９】以下本発明について詳しく説明する。本発
明で利用されるグリニヤール試薬としては、ｔｅｒｔ−
ブチルマグネシウムクロライド、ｔｅｒｔ−ブチルマグ
ネシウムブロマイド、１，１−ジメチルプロピルマグネ
シウムクロライド、１，１−ジメチルプロピルマグネシ
ウムブロマイド、１，１−ジエチルプロピルマグネシウ
ムクロライド、１，１−ジエチルプロピルマグネシウム
ブロマイド等が例示される。The present invention will be described in detail below. The Grignard reagent used in the present invention includes tert-
Butyl magnesium chloride, tert-butyl magnesium bromide, 1,1-dimethylpropyl magnesium chloride, 1,1-dimethylpropyl magnesium bromide, 1,1-diethylpropyl magnesium chloride, 1,1-diethylpropyl magnesium bromide and the like are exemplified. .
【００１０】また本発明におけるＲＳｉＨ2 Ｃｌで示さ
れる第３級炭化水素基を有する有機ケイ素化合物として
は、ｔｅｒｔ−ブチルクロルシラン、１，１−ジメチル
プロピルクロルシラン、１，１−ジエチルプロピルクロ
ルシラン等が例示される。The organic silicon compound having a tertiary hydrocarbon group represented by RSiH 2 Cl in the present invention is tert-butylchlorosilane, 1,1-dimethylpropylchlorosilane, 1,1-diethylpropylchlorosilane. Etc. are illustrated.
【００１１】本発明の製造方法は、先ず、金属マグネシ
ウムとハロゲン化第３級炭化水素化合物とをテトラヒド
ロフランやジエチルエーテル等のエーテル系単独溶媒
下、またはエーテル系溶媒とベンゼンやトルエンなどの
ような他の炭化水素系不活性溶媒との混合溶媒下で反応
させてグリニヤール試薬を作り、このグリニヤール試薬
にジクロルシランを添加して反応させる。In the production method of the present invention, first, metallic magnesium and a halogenated tertiary hydrocarbon compound are used in an ether-based single solvent such as tetrahydrofuran or diethyl ether, or an ether-based solvent and another such as benzene or toluene. The reaction is performed in a mixed solvent with the hydrocarbon-based inert solvent described in 1 above to prepare a Grignard reagent, and dichlorosilane is added to the Grignard reagent to react.
【００１２】本発明における反応温度は、−２０℃から
１５０℃の範囲で適用可能であるが、反応速度及び操作
性等の面から、好ましくは０℃から４０℃である。The reaction temperature in the present invention is applicable in the range of -20 ° C to 150 ° C, but is preferably 0 ° C to 40 ° C in view of reaction rate and operability.
【００１３】本発明におけるグリニヤール試薬とジクロ
ルシランとの反応のモル比は１：０．１から１：１０の
範囲で行うことができるが、通常は化学量論的に等しい
１：１付近が好ましい。なお原料となるグリニヤール試
薬は、酸素や水分等と反応するので、窒素やアルゴン等
の不活性ガスの存在下で反応を行うことが好ましい。The molar ratio of the reaction between the Grignard reagent and the dichlorosilane in the present invention can be carried out in the range of 1: 0.1 to 1:10, but it is usually preferable that the stoichiometric ratio is about 1: 1. Since the Grignard reagent as a raw material reacts with oxygen, water and the like, it is preferable to carry out the reaction in the presence of an inert gas such as nitrogen and argon.
【００１４】[0014]
【発明の効果】本発明の方法によれば一般式ＲＳｉＨ2
Ｃｌで示される第３級炭化水素基を有する有機ケイ素化
合物を工業的に有利な方法で製造することができる。ま
た、本発明により製造される第３級炭化水素基を有する
有機ケイ素化合物は、シランカップリング剤、シリル化
剤及び他の有機ケイ素化合物製造の原料として有用であ
る。According to the method of the present invention, the general formula RSiH 2
The organosilicon compound having a tertiary hydrocarbon group represented by Cl can be produced by an industrially advantageous method. Further, the organosilicon compound having a tertiary hydrocarbon group produced by the present invention is useful as a raw material for producing a silane coupling agent, a silylating agent and other organosilicon compounds.
【００１５】[0015]
【実施例】次に本発明を実施例により具体的に説明す
る。 実施例１ 温度計、撹拌器、冷却器及び適下ロートを取り付けた１
０００ｃｃの４つ口フラスコにｔｅｒｔ−ブチルマグネ
シウムクロライド０．５モルを含むジエチルエーテル溶
液５８８ｃｃを仕込み、窒素雰囲気下２０℃で撹拌をし
ながら、ジクロルシラン５４．５ｇ（０．５４モル）を
ジエチルエーテル３１６ｇとともに適下ロートから適下
し、その後１時間撹拌を続けた。次に反応液をロータリ
ーエバポレーターに仕込み、７０ｔｏｒｒ下に、オイル
バスで８５℃に加熱して留出液をえた。引続き、この留
出液を蒸留塔を用いて精製し、ｔｅｒｔ−ブチルクロル
シランを４１ｇ（０．３４モル）回収した。なお、反応
液及び最終製品の組成についてはガスクロマトグラフィ
ー分析により確認した。EXAMPLES Next, the present invention will be specifically described by way of examples. Example 1 1 equipped with a thermometer, a stirrer, a cooler and an appropriate lower funnel
A diethyl ether solution (588 cc) containing 0.5 mol of tert-butyl magnesium chloride was charged into a 000 cc four-necked flask, and 54.5 g (0.54 mol) of dichlorosilane was added to 316 g of diethyl ether while stirring at 20 ° C. under a nitrogen atmosphere. Then, the mixture was properly removed from the appropriate funnel and the stirring was continued for 1 hour. Next, the reaction solution was charged into a rotary evaporator and heated to 85 ° C. in an oil bath under 70 torr to obtain a distillate. Subsequently, this distillate was purified using a distillation column to recover 41 g (0.34 mol) of tert-butylchlorosilane. The composition of the reaction solution and the final product was confirmed by gas chromatography analysis.
【００１６】実施例２ 温度計、撹拌器、冷却器及び適下ロートを取り付けた３
０００ｃｃの４つ口フラスコに、２−クロロ−２−メチ
ルブタン１３１ｇ（１．２３モル）を仕込み、それにヨ
ウ素０．３ｇ、金属マグネシウム３５．８ｇ（１．４７
モル）及びテトラヒドロフラン１２００ｃｃを入れて窒
素雰囲気下に外温を６５℃に維持して、テトラヒドロフ
ランを還流しながら３時間反応させてグリニャール試薬
（１−１−ジメチルプロピルマグネシウムクロライド）
１．００モルを含むテトラヒドロフラン溶液１５４０ｃ
ｃを得た。引続き、この溶液に１７℃でジクロルシラン
１０１．３ｇ（１．００３モル）を約１時間かけて添加
した後、更に約１時間撹拌を継続した。次に反応液を取
り出し、それにヘキサンを３０００ｃｃ加え、塩を析出
させてろ過し、このろ液を蒸留塔を用いて精製し、１−
１−ジメチルプロピルクロルシランを８１グラム回収し
た。なお、反応液及び最終製品の組成についてはガスク
ロマトグラフィー分析により確認した。Example 2 3 equipped with a thermometer, a stirrer, a cooler and an appropriate lower funnel
To a 000 cc four-necked flask, 131 g (1.23 mol) of 2-chloro-2-methylbutane was charged, and 0.3 g of iodine and 35.8 g (1.47 of magnesium magnesium) were added to the flask.
Mol) and 1200 cc of tetrahydrofuran and keeping the external temperature at 65 ° C. under a nitrogen atmosphere, and reacting for 3 hours while refluxing tetrahydrofuran to give a Grignard reagent (1-1-dimethylpropylmagnesium chloride).
Tetrahydrofuran solution containing 1.00 mol 1540c
I got c. Subsequently, 101.3 g (1.003 mol) of dichlorosilane was added to this solution at 17 ° C. over about 1 hour, and stirring was continued for about 1 hour. Next, the reaction solution was taken out, 3,000 cc of hexane was added thereto to precipitate a salt, which was filtered, and the filtrate was purified using a distillation column.
81 grams of 1-dimethylpropylchlorosilane was recovered. The composition of the reaction solution and the final product was confirmed by gas chromatography analysis.
【００１７】比較例１ 温度計、撹拌器、冷却器及び適下ロートを取り付けた１
０００ｃｃの４つ口フラスコにｔｅｒｔ−ブチルマグネ
シウムクロライド０．５モルを含むテトラヒドロフラン
溶液５８８ｃｃを仕込み窒素雰囲気下に２５℃で撹拌を
しながらトリクロルシラン７２．６ｇ（０．５４モル）
をテトラヒドロフラン３１６ｇとともに適下ロートから
適下し、その後３時間撹拌を続けた。次に反応液をロー
タリーエバポレーターに仕込み、７０ｔｏｒｒ下にオイ
ルバスで１４０℃に加熱して留出液を得た。この液をガ
スクロマトグラフィーで分析した結果、ｔｅｒｔ−ブチ
ルクロルシランは検出されなかった。Comparative Example 1 1 equipped with a thermometer, a stirrer, a cooler and an appropriate lower funnel
A 4,000 cc four-necked flask was charged with 588 cc of a tetrahydrofuran solution containing 0.5 mol of tert-butyl magnesium chloride, and 72.6 g (0.54 mol) of trichlorosilane while stirring at 25 ° C. under a nitrogen atmosphere.
Was mixed with 316 g of tetrahydrofuran from an appropriate funnel and then stirred for 3 hours. Next, the reaction solution was charged into a rotary evaporator and heated to 140 ° C. in an oil bath under 70 torr to obtain a distillate. As a result of analyzing this liquid by gas chromatography, tert-butylchlorosilane was not detected.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 橋本 崇男 新潟県西頸城郡青海町大字青海2209番地 電気化学工業株式会社青海工場内 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Takao Hashimoto 2209 Aomi, Aomi-cho, Nishikubiki-gun, Niigata Prefecture Electrochemical Industry Co., Ltd. Aomi Plant
Claims (1)
水素基、Ｘはハロゲン原子である）で示されるグリニヤ
ール試薬とジクロルシランを反応させて、一般式ＲＳｉ
Ｈ2 Ｃｌ（式中、Ｒは第３級炭化水素基である）で示さ
れる第３級炭化水素基を有する有機ケイ素化合物の製造
方法。1. A Grignard reagent represented by the general formula RMgX (wherein R is a tertiary hydrocarbon group and X is a halogen atom) is reacted with dichlorosilane to give the general formula RSi.
A method for producing an organosilicon compound having a tertiary hydrocarbon group represented by H 2 Cl (wherein R is a tertiary hydrocarbon group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4232259A JPH0673070A (en) | 1992-08-31 | 1992-08-31 | Production of organosilicon compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4232259A JPH0673070A (en) | 1992-08-31 | 1992-08-31 | Production of organosilicon compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0673070A true JPH0673070A (en) | 1994-03-15 |
Family
ID=16936465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4232259A Pending JPH0673070A (en) | 1992-08-31 | 1992-08-31 | Production of organosilicon compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0673070A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0656363A1 (en) * | 1993-12-03 | 1995-06-07 | Shin-Etsu Chemical Co., Ltd. | Process for preparing a silane having a tertiary hydrocarbon group at the alpha position thereof |
-
1992
- 1992-08-31 JP JP4232259A patent/JPH0673070A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0656363A1 (en) * | 1993-12-03 | 1995-06-07 | Shin-Etsu Chemical Co., Ltd. | Process for preparing a silane having a tertiary hydrocarbon group at the alpha position thereof |
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