JPH0426693A - Novel silane compound and production thereof - Google Patents
Novel silane compound and production thereofInfo
- Publication number
- JPH0426693A JPH0426693A JP12885490A JP12885490A JPH0426693A JP H0426693 A JPH0426693 A JP H0426693A JP 12885490 A JP12885490 A JP 12885490A JP 12885490 A JP12885490 A JP 12885490A JP H0426693 A JPH0426693 A JP H0426693A
- Authority
- JP
- Japan
- Prior art keywords
- silane compound
- butoxy
- reaction
- formula
- mmol
- 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
- -1 silane compound Chemical class 0.000 title claims description 26
- 229910000077 silane Inorganic materials 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000005457 ice water Substances 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 230000037048 polymerization activity Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NTHKCSDJQGWPJY-UHFFFAOYSA-N CCCC[SiH](OC)OC Chemical compound CCCC[SiH](OC)OC NTHKCSDJQGWPJY-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229920000576 tactic polymer Polymers 0.000 description 1
- MOOUPSHQAMJMSL-UHFFFAOYSA-N tert-butyl(trichloro)silane Chemical compound CC(C)(C)[Si](Cl)(Cl)Cl MOOUPSHQAMJMSL-UHFFFAOYSA-N 0.000 description 1
- HXLWJGIPGJFBEZ-UHFFFAOYSA-N tert-butyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C(C)(C)C HXLWJGIPGJFBEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Abstract
Description
【発明の詳細な説明】
発明の技術分野
本発明は新規なシラン化合物およびその製造方法に関し
、さらに詳しくは、触媒成分、シランカップリング剤な
どとして用いられる新規シラン化合物およびその製造方
法に関する。DETAILED DESCRIPTION OF THE INVENTION Technical Field of the Invention The present invention relates to a novel silane compound and a method for producing the same, and more particularly to a novel silane compound used as a catalyst component, a silane coupling agent, etc. and a method for producing the same.
発明の技術的背景
プロピレン重合を行なう際には、従来より触媒成分とし
て、アルコキシシラン類を用いると、高い立体規則性を
有する重合体が製造しうることか知られている。しかし
ながら、従来から知られているアルコキシシラン等を用
いて調製された触媒成分を用いてプロピレンを重合させ
ても高重合活性と高立体規則性の両立を十分に満足させ
ることはできなかった。TECHNICAL BACKGROUND OF THE INVENTION It has been known that when propylene polymerization is carried out, a polymer having high stereoregularity can be produced by using alkoxysilanes as a catalyst component. However, even when propylene is polymerized using a catalyst component prepared using a conventionally known alkoxysilane or the like, it has not been possible to sufficiently satisfy both high polymerization activity and high stereoregularity.
またシラン化合物はシランカップリング剤あるいは樹ｊ
指改質剤としての用途が期待されており、このため新規
なシラン化合物の出現が望まれている。In addition, silane compounds can be used as silane coupling agents or trees.
It is expected to be used as a finger modifier, and for this reason, the emergence of new silane compounds is desired.
発明の１ユ１的
本発明は、高活性、高立体規則性重合触媒成分あるいは
シランカップリング剤などとして有用な新規シラン化合
物およびその製造方法を提供することを目的としている
。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel silane compound useful as a highly active, highly stereoregular polymerization catalyst component or a silane coupling agent, and a method for producing the same.
発明の概要
本発明に係る新規シラン化合物は、下記式［Ｉ］で表わ
されるＬｅｒｔ−ブトキシ−１ａｒｔ−ブチルジメトキ
シシランである。Summary of the Invention The novel silane compound according to the present invention is Lert-butoxy-1art-butyldimethoxysilane represented by the following formula [I].
［Ｉ］
このような新規シラン化合物［Ｉ］は、ＬｅｒＬブチル
トリハロシランと、ＬｅｒＬ−ブチルアルコールとを反
応させ、次いで、得られた反応物（ｔｅｒｔブトキシ−
ｔｅｒｔ−ブチルジハロシラン）とメタノールとを反応
させることにより製造することかできる。この際、反応
系に脱ハロゲン化水素剤を存在させておくことが好まし
い。[I] Such a new silane compound [I] is produced by reacting LerL-butyl trihalosilane and LerL-butyl alcohol, and then reacting the resulting reaction product (tert-butoxy-
It can be produced by reacting tert-butyldihalosilane) with methanol. At this time, it is preferred that a dehydrohalogenating agent be present in the reaction system.
本発明に係る」二足のような新規シラン化合物［Ｉ］は
、高活性、高立体規則性重合体製造用触媒成分あるいは
シランカップリング剤、樹脂改質剤として用いられる。The novel bipedal silane compound [I] according to the present invention is used as a catalyst component, a silane coupling agent, or a resin modifier for producing highly active, highly stereoregular polymers.
発明の詳細な説明
以下、本発明に係る新規シラン化合物およびその製造方
法について具体的に説明する。DETAILED DESCRIPTION OF THE INVENTION The novel silane compound and method for producing the same according to the present invention will be specifically described below.
新規シラン化合物
本発明に係る新規シラン化合物は、下記式［Ｉ］で表わ
されるｔｅｒＬ−ブトキシ−ＬｅｒＬ−ブチルジメＩ・
キシシランである。Novel silane compound The novel silane compound according to the present invention is a terL-butoxy-LerL-butyldimeI compound represented by the following formula [I].
It is xysilane.
このシラン化合物［Ｔ］は、沸点か６２℃／１５ｍｍＨ
ｇであり、常温で無色の高粘度液体である。このシラン
化合物［Ｉ］の構造はＧ Ｃ−Ｍ Ｓ 。This silane compound [T] has a boiling point of 62°C/15mmH.
g, and is a colorless, highly viscous liquid at room temperature. The structure of this silane compound [I] is G C-MS.
Ｈ−ＮＭＲ，ＩＲ等により確認することができる。It can be confirmed by H-NMR, IR, etc.
たとえば、 Ｈ−Ｎ Ｍ Ｒを用いて、このＬｃｒＬブ
Ｉ・キシ−１ａｒ Ｌ−プチルンメトキシシランを分析
すると、０． ９２２ｐｐＩＩ１１．：Ｌｅｒｔ−ブチ
ル基に起因するピークが、１．．２９３ｐｐｍにｔｅｒ
ｔ−ブトキシ基に起因するピークが、そして、３．５６
８ｐｐｍにメトキシ基に起因するピークが観察される。For example, when this LcrL-butylenemethoxysilane is analyzed using H-NMR, it is found that 0. 922ppII11. :The peak due to the Lert-butyl group is 1. ．． ter to 293 ppm
The peak due to the t-butoxy group is 3.56
A peak due to the methoxy group is observed at 8 ppm.
また、赤外線吸収スペクトル（ＩＲ）を測定すると、２
７００〜３０００印＝１付近にブチル基、ブトキシ基、
メトキシ基に起因するピークが観察され、１１００〜１
．２００ ｃｍ−’付近にエーテル結合に起因するピー
クが観察される。In addition, when measuring the infrared absorption spectrum (IR), 2
700-3000 mark = around 1 butyl group, butoxy group,
A peak due to methoxy group was observed, 1100-1
．． A peak due to an ether bond is observed around 200 cm-'.
このシラン化合物［Ｉ］を触媒成分として用いると、高
立体規則性を有するポリプロピレン、ポリブテン等のオ
レフィン系重合体を、高重合活性下に製造することがで
きる。When this silane compound [I] is used as a catalyst component, olefin polymers such as polypropylene and polybutene having high stereoregularity can be produced with high polymerization activity.
また、このシラン化合物［Ｉ］は加水分解晶を有してい
るため、シランカップリング剤、重合性モノマーおよび
樹脂改質剤として用いられる。Moreover, since this silane compound [I] has hydrolyzed crystals, it is used as a silane coupling agent, a polymerizable monomer, and a resin modifier.
製 造 方 法
このような新規なシラン化合物［Ｉ］を製造するには、
たとえば、まず初めに下記式［Ｉ１］に示すように、Ｌ
ｅｒＬ−ブチルトす／ＸロシランとＬｃｒＬ−ブチルア
ルコールとを反応させ、ｔｅｒＬ−ブトキシ−１ｅｒｔ
−ブチルジハロシランを生成させる。この際、反応系に
脱ハロゲン化水素剤を共存させておくことが特に好まし
い。Production method To produce such a new silane compound [I],
For example, first, as shown in the following formula [I1], L
erL-butoxy-1ert is reacted with LcrL-butyl alcohol and terL-butoxy-1ert
- producing butyldihalosilane; At this time, it is particularly preferable to coexist a dehydrohalogenating agent in the reaction system.
（ＣＩ！
１Ｘ
３−−→
・・ ［Ｉ１］
但し、式［ＩＩ］中、Ｘはハロゲン原子を表わしている
が、中でもＣ，１７またはＢｒであることか好ましい。(CI! 1X 3--→ ... [I1] However, in formula [II], X represents a halogen atom, and among them, C, 17 or Br is preferable.
脱ハロゲン化水素剤としては、第三級アミン、窒素含有
複素環化合物、たとえばピリジン、キノリン、イソキノ
リンなどが挙げられるが、これらの内でもピリジン、キ
ノリンが好ましく用いられる。Examples of the dehydrohalogenation agent include tertiary amines and nitrogen-containing heterocyclic compounds such as pyridine, quinoline, and isoquinoline, among which pyridine and quinoline are preferably used.
上記式［Ｉ１］で表わされる反応を行なう際には、ｔａ
ｒｔ−ブチルトリハロシラン１モル当り、ｔｅｒｔ−ブ
チルアルコールを１〜１０倍モルの量で、脱ハロゲン化
水素剤を１〜１０倍モルの量で用いて、０〜１５０℃、
好ましくは３０〜８０℃にて、１〜２０時間、好ましく
は２〜１０時間反応させることが望ましい。When carrying out the reaction represented by the above formula [I1], ta
per mole of rt-butyltrihalosilane, using tert-butyl alcohol in an amount of 1 to 10 times the mole and a dehydrohalogenating agent in an amount of 1 to 10 times the mole, at 0 to 150 °C,
It is desirable to react preferably at 30 to 80°C for 1 to 20 hours, preferably 2 to 10 hours.
次いで、前記式［ＩＩ］で示す反応により得られたＬｃ
ｒＬ−ブトキシ−ＬｃｒＬ−ブチルジハロシランとメタ
ノールとを下記式［Ｉ［［］で示すように反応させると
、本発明に係るＬｅｒＬ−ブトキシ−ｔａｒｔ−ブチル
ジメトキシシラン［ＩＩが得られる。Then, Lc obtained by the reaction represented by the above formula [II]
When rL-butoxy-LcrL-butyldihalosilane and methanol are reacted as shown in the following formula [I[[], LerL-butoxy-tart-butyldimethoxysilane [II] according to the present invention is obtained.
・・・ ［ｍ］
上記式［Ｉ１１］で表わされる反応を行なう際に必要に
より用いられる脱ハロゲン化水素剤は、前記式［Ｉ１］
で示す反応において用いられる化合物と同一であっても
異なっていてもよいが、通常では同一である。... [m] The dehydrohalogenating agent used as necessary when carrying out the reaction represented by the above formula [I1] is
It may be the same as or different from the compound used in the reaction shown in, but is usually the same.
」二足式［Ｉ１１］で表わされる反応を行なう際には、
ｔｃｒＬ−ブトキシ−ＬｅｒＬ−ブチルジハロシラン１
モル当り、メタノールを２〜１０倍モルの量で、脱ハロ
ゲン化水素剤を２〜１０倍モルの量で用いて、０〜１５
０°Ｃ１好ましくは３０〜８０℃にて、１〜３０時間、
好ましくは５〜１５時間反応させることが好ましい。” When carrying out the reaction expressed by the bipedal formula [I11],
tcrL-butoxy-LerL-butyldihalosilane 1
Using methanol in an amount of 2 to 10 times the mole and a dehydrohalogenating agent in an amount of 2 to 10 times the mole, 0 to 15
0°C1, preferably at 30-80°C for 1-30 hours,
It is preferable to react for 5 to 15 hours.
なお、」二足式［ｍ］で表わされる反応は、通常、前記
式［ＩＴ］の反応を行なった結果、脱ハロゲン化水素剤
およびｔｅｒＬ−ブトキシ−１ｅｒｔ−ブチルシバロン
ラン等が含まれた反応混合物に、さらにメタノールを加
えることにより行なわれる。Incidentally, the reaction represented by the two-legged formula [m] is usually a reaction in which a dehydrohalogenating agent, terL-butoxy-1ert-butylcybalonran, etc. are included as a result of the reaction of the above formula [IT]. This is done by adding more methanol to the reaction mixture.
本発明においては、上記式［ＩＩ］、［ｍ］の反応によ
り中成するハロゲン化水素を不活性気体を用いて反応系
から除去してもよい。このようにハロゲン化水素を除去
すると、式［ｎ］、［ＩＩ［］の反応を速やかに進行さ
せることができる。 本発明に係る新規なシラン化合物
［ＩＩを製造する際に、上記のような方法を採用すれば
高収率でｔｅｒｔ−ブトキシ−Ｌｅｒ Ｌ−ブチルジメ
トキシシラン［ＩＩか得られる。In the present invention, the hydrogen halide formed by the reaction of the above formulas [II] and [m] may be removed from the reaction system using an inert gas. By removing the hydrogen halide in this manner, the reactions of formulas [n] and [II[] can proceed rapidly. When producing the novel silane compound [II according to the present invention], if the above method is employed, tert-butoxy-Ler L-butyldimethoxysilane [II] can be obtained in high yield.
なお、本発明に係る新規なシラン化合物［ＩＩを製造す
るには、ＬｅｒＬ−ブチルトリメトキシシラン反応を利
用することもできる。In addition, in order to manufacture the novel silane compound [II based on this invention, LerL-butyltrimethoxysilane reaction can also be utilized.
このアルコール交換反応の際には、触媒として、−数的
に周知の酸または塩基を用いることができる。In this alcohol exchange reaction, numerically known acids or bases can be used as catalysts.
このようにして得られたｔｅｒｔ−ブトキシ−Ｌｅｒｔ
−ブチルジメトキシシラン［Ｉ］の構造は、ＧＣ−ＭＳ
，’ Ｈ−ＮＭＲ、ＩＲ等により確認される。tert-butoxy-Lert thus obtained
-The structure of butyldimethoxysilane [I] was determined by GC-MS
,' Confirmed by H-NMR, IR, etc.
発明の効果
本発明に係る新規なシラン化合物［Ｉ］は、たとえば触
媒成分として用いると、高い立体規則性を有する重合体
を、高重合活性下に製造することができる。またこのよ
うなシラン化合物は、シランカップリング剤、樹脂改質
剤などとして用いることもできる。Effects of the Invention When the novel silane compound [I] according to the present invention is used, for example, as a catalyst component, a polymer having high stereoregularity can be produced with high polymerization activity. Further, such silane compounds can also be used as silane coupling agents, resin modifiers, and the like.
また、本発明においては、ｔｅｒＬ−ブトキシ−Ｌｃｒ
Ｌ−ブチルジメトキシシランを製造する際に、ＬｅｒＬ
−ブチルトリハロシランと、ＬｅｒＬ−ブチルアルコー
ルとを、好ましくは脱ハロゲン化水素剤の存在下に反応
させ、次いで、得られた反応物とメタノールとを脱ハロ
ゲン化水素剤の存在下に反応させると、ＬｃｒＬ−ブト
キシ−ｔｅｒＬ−ブチルジメトキシシランが高収率で得
られる。Further, in the present invention, terL-butoxy-Lcr
When producing L-butyldimethoxysilane, LerL
-butyltrihalosilane and LerL-butyl alcohol are reacted, preferably in the presence of a dehydrohalogenating agent, and then the resulting reactant and methanol are reacted in the presence of a dehydrohalogenating agent. , LcrL-butoxy-terL-butyldimethoxysilane is obtained in high yield.
以下、本発明を実施例によりさらに具体的に説明するが
、本発明はこれらの実施例に（ｉｌら制約されるもので
はない。Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
磁気撹拌子、冷却管、滴下ロートを備えた２００ｍ１三
ツロフラスコにｔ−ブチルトリクロロシラン１．２．２
ｇ （６３，７ミリモル）と乾燥エーテル６０１を仕込
み、氷水で外部より冷却した。Example 1 t-Butyltrichlorosilane 1.2.2 in a 200 ml three-tube flask equipped with a magnetic stirrer, condenser, and dropping funnel.
g (63.7 mmol) and dry ether 601 were charged, and the mixture was cooled externally with ice water.
これにｔ−ブチルアルコール１８． １ｇ （２４４ミ
リモル）とピリジン１８．１ｇ（２２９ミリモル）の混
合物を撹拌下３０分て滴下した。その後５時間加熱還流
した。再び氷水で冷却し、メタノール５．４ｇ（１６９
ミリモル）を１−５分て滴下した。Add 18% of t-butyl alcohol to this. A mixture of 1 g (244 mmol) and 18.1 g (229 mmol) of pyridine was added dropwise with stirring over 30 minutes. Thereafter, the mixture was heated under reflux for 5 hours. Cool again with ice water and add 5.4 g (169 g) of methanol.
mmol) was added dropwise over 1-5 minutes.
滴下終了後、１０時間加熱還流して反応を完結した。生
成した沈澱を濾別し、濾液を蒸留することにより、ｔ−
ブトキシｔ−ブチルジメトキシシラン８．７ｇ （３９
，６ミリモル）を得た。収率は６２％、沸点は６２℃／
１５ｍ＋ｏＨｇであった。構造は、ＧＣ−ＭＳ、ＩＨ−
ＮＭＲ，ＩＲで確認した。Ｇ（、−ＭＳデータは以下の
とおりであり、１Ｈ−ＮＭＲｌＩＲはそれぞれ第１図、
第２図に示した。After the dropwise addition was completed, the reaction was completed by heating under reflux for 10 hours. By filtering the generated precipitate and distilling the filtrate, t-
Butoxy t-butyldimethoxysilane 8.7g (39
, 6 mmol) was obtained. Yield: 62%, boiling point: 62℃/
It was 15m+oHg. The structure is GC-MS, IH-
Confirmed by NMR and IR. G(,-MS data are as follows, 1H-NMRlIR are shown in Figure 1, respectively.
It is shown in Figure 2.
ＧＣ−ＭＳ ： ｍ／ｅ （スペクトル強度比）２２０
（０，３） 、２０５ （７，７）、１６Ｂ（１４，
７）、１０７ （１００）実施例２
実施例１と同様の反応装置にＬ−ブチルトリクロロシラ
ン１．２．２ｇ （６２，７ミリモル）と乾燥エーテル
６０１を仕込み、氷水で外部より冷却し１ま
た。これに［−ブチルアルコール１８．１ｇ（２４４ミ
リモル）の乾燥エーテル２０１溶液を撹拌下３０分で滴
下した。その後１５時間加熱還流した。再び氷水で冷却
し、メタノール５６４ｇ（１６９ミリモル）を１５分で
滴下した。滴下終了後、２０時間加熱還流した。反応液
を蒸留することにより、［−ブトキシｔ−ブチルジメト
キシシラン１．９ｇ （８，６ミリモル）を得た。収率
は１４％であった。GC-MS: m/e (spectral intensity ratio) 220
(0,3), 205 (7,7), 16B (14,
7), 107 (100) Example 2 1.2.2 g (62.7 mmol) of L-butyltrichlorosilane and dry ether 601 were placed in the same reactor as in Example 1, cooled externally with ice water, and then cooled for one or more times. . A solution of 18.1 g (244 mmol) of [-butyl alcohol] in dry ether 201 was added dropwise to the mixture with stirring over 30 minutes. Thereafter, the mixture was heated under reflux for 15 hours. The mixture was cooled again with ice water, and 564 g (169 mmol) of methanol was added dropwise over 15 minutes. After the dropwise addition was completed, the mixture was heated under reflux for 20 hours. By distilling the reaction solution, 1.9 g (8.6 mmol) of [-butoxyt-butyldimethoxysilane was obtained. The yield was 14%.
実施例３
磁気撹拌子、冷却管を備えた１００１三ツロフラスコに
ｔ−ブチルトリメトキシシラン（ １． ６ ８ ミリ
モル） ｔ−ブチルアルコール１、 ２ 、 ５ ｇ
（ １． ６ ８ミリモル）およびカリウムＬーブト
キシド２０ｍｇ（０．１８ミリモル）を仕込み、８０℃
の油浴で１０時間加熱撹拌した。冷却後塩化アンモニウ
ムを添加することによりアルカリを中和し、蒸留するこ
とによりＬ−ブトキシｔ−ブチルジメトキシシラン５．
９ｇ （２８ミリモル）を得た。収率は１７％であった
。Example 3 t-Butyltrimethoxysilane (1.68 mmol) t-butyl alcohol 1, 2, 5 g in a 1001 three-turn flask equipped with a magnetic stirrer and a condenser.
(1.68 mmol) and 20 mg (0.18 mmol) of potassium L-butoxide were added and heated at 80°C.
The mixture was heated and stirred in an oil bath for 10 hours. After cooling, the alkali is neutralized by adding ammonium chloride, and L-butoxyt-butyldimethoxysilane is obtained by distillation5.
9 g (28 mmol) were obtained. The yield was 17%.
第１図は、本発明に係るＬｅｒｔ−ブトキシ−ｔｅｒｔ
−ブチルジメトキシシランについてＩＨ−ＮＭＲ測定の
結果を、第２図はＩＲ測測定結果を示している。FIG. 1 shows Lert-butoxy-tert according to the present invention.
-Butyldimethoxysilane is shown in IH-NMR measurement results, and FIG. 2 shows IR measurement results.
Claims (3)
ブチルアルコールとを反応させ、次いで、得られた反応
物とメタノールとを反応させることを特徴とする下記式
［ I ］で表わされるシラン化合物の製造方法。 ▲数式、化学式、表等があります▼・・・［ I ］(2) tert-butyltrihalosilane and tert-
A method for producing a silane compound represented by the following formula [I], which comprises reacting the silane compound with butyl alcohol and then reacting the obtained reaction product with methanol. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・［I］
トリハロシランと、ｔｅｒｔ−ブチルアルコールとを反
応させ、次いで、得られた反応物とメタノールとを反応
させることを特徴とする下記式［ I ］で表わされるシ
ラン化合物の製造方法。 ▲数式、化学式、表等があります▼・・・［ I ］(3) The following formula [ I ] A method for producing a silane compound represented by ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・［I］
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12885490A JPH0426693A (en) | 1990-05-18 | 1990-05-18 | Novel silane compound and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12885490A JPH0426693A (en) | 1990-05-18 | 1990-05-18 | Novel silane compound and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0426693A true JPH0426693A (en) | 1992-01-29 |
Family
ID=14995018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12885490A Pending JPH0426693A (en) | 1990-05-18 | 1990-05-18 | Novel silane compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0426693A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5690400B2 (en) * | 2011-03-23 | 2015-03-25 | ヤマハ発動機株式会社 | Electrode material, battery, and method for producing electrode material |
-
1990
- 1990-05-18 JP JP12885490A patent/JPH0426693A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5690400B2 (en) * | 2011-03-23 | 2015-03-25 | ヤマハ発動機株式会社 | Electrode material, battery, and method for producing electrode material |
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