JPS62263189A - Production of diaryldihalosilane - Google Patents
Production of diaryldihalosilaneInfo
- Publication number
- JPS62263189A JPS62263189A JP10684186A JP10684186A JPS62263189A JP S62263189 A JPS62263189 A JP S62263189A JP 10684186 A JP10684186 A JP 10684186A JP 10684186 A JP10684186 A JP 10684186A JP S62263189 A JPS62263189 A JP S62263189A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- reduced pressure
- aryldihalosilane
- catalyst
- diaryldihalosilane
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000007323 disproportionation reaction Methods 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 8
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 abstract description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 229920002379 silicone rubber Polymers 0.000 abstract description 2
- 239000004945 silicone rubber Substances 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 8
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical group C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 7
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- -1 ethylphenyl groups Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は、ジアリールジハロシランの製造方法に関する
。さらに詳しくは、モノアリールジハロシラン(以後、
単にアリールジハロシランと称す)の不均化反応よる効
率的なジアリールジハロシランの製造方法を提供するも
のである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing diaryldihalosilanes. More specifically, monoaryldihalosilane (hereinafter referred to as
The purpose of the present invention is to provide an efficient method for producing diaryldihalosilanes by a disproportionation reaction of aryldihalosilanes (simply referred to as aryldihalosilanes).
[従来の技術]
珪素原子に二つ同種の芳香族基(以後、アリール基と称
す)と二つの同種または異種のハロゲン原子を結合して
なるジアリールジハロシランは、シリコーンオイル、シ
リコーンゴム、シリコーンワニスなどの始発原料として
重要視されている。[Prior Art] Diaryldihalosilane, which is formed by bonding two aromatic groups of the same type (hereinafter referred to as aryl groups) and two halogen atoms of the same type or different types to a silicon atom, can be used as silicone oil, silicone rubber, or silicone. It is considered important as a starting material for products such as varnish.
従来、これらのジアリールジハロシランの製造方法の一
つとして、該ジアリールジハロシラン(Ar2siX2
と示す)と同種のアリール基を有するアリールジハロシ
ラン(ArS i (H)X2と示す)t/−原料に用
い、2ArS i (H)X2→Ar2siX2+H2
siX2なる反応式で示される不均化反応をフリーデル
クラフッ反応の触媒、例えばハロゲン化金属ルイス酸触
媒の存在下に常圧ドで行わせる方法が、例えば英国特許
第738541号明細書に記載され公知である。Conventionally, as one of the methods for producing these diaryldihalosilanes, the diaryldihalosilanes (Ar2siX2
2ArS i (H)X2 → Ar2siX2+H2
For example, British Patent No. 738,541 describes a method in which the disproportionation reaction represented by the reaction formula siX2 is carried out at normal pressure in the presence of a Friedel-Crach reaction catalyst, such as a metal halide Lewis acid catalyst. It is well known.
[発明が解決しようとする問題点コ
しかるに、上記した英国特許第738541 Q明細書
に記載の方法によると、原料のアリールジハロシランを
常圧で沸点温度の高温下に長時間加熱しても、目的とす
るジアリールジハロシランが低収率にしか製造できない
という欠点があった。[Problems to be Solved by the Invention]However, according to the method described in the above-mentioned British Patent No. 738541 Q, even if the raw material aryldihalosilane is heated at normal pressure and at a high boiling point temperature, However, the disadvantage was that the desired diaryldihalosilane could only be produced in low yield.
[間に口を解決するための手段]
本発明者らは1、上記の如きアリールジハロシランの不
均化反応によるアリールジハロシランの製造について鋭
意研究を重ねた結果、該不均化反応の実施に際して、反
応系を減圧とすることが目的のジアリールジハロシラン
を高収率に得る上で極めて効果的であることを見い出し
、本発明を完成するに至った。すなわち本発明は、アリ
ールジハロシランの不均化反応を減圧の条件下に行うこ
とを特徴とする高収率に目的のジアリールジハロシラン
を製造する方法である。[Means for solving the problem] The present inventors 1. As a result of intensive research on the production of aryldihalosilanes by the disproportionation reaction of aryldihalosilanes as described above, the present inventors found that the disproportionation reaction The present inventors have discovered that reducing the pressure in the reaction system is extremely effective in obtaining the desired diaryldihalosilane in a high yield, leading to the completion of the present invention. That is, the present invention is a method for producing a desired diaryldihalosilane in a high yield, which is characterized in that the disproportionation reaction of an aryldihalosilane is carried out under reduced pressure conditions.
本発明において用いられる原料のアリールジハロシラン
は、特に限定されることな〈従来公知のものがそのまま
好適に採用される0例えば、アリールジハロシランはア
リール基およびハロゲン基として以下に述べるようなも
のを組み合わせた化合物が好ましい。すなわち、アリー
ル基としてはフェニル基、トルイル基やエチルフェニル
基に代表されるアルカリ基、クロルフェニル基やフルオ
ルフェニル基に代表されるハロゲン化フェニル基、その
ほかトリフルオルメチル基、フェノキシフェニル基、ビ
フェニル基あるいはこれらのアルキルおよびまたはハロ
ゲン置換された基などが掲げられる。また、ハロゲン基
としては塩素原子が最も好ましいが、臭素原子やフッ素
原子も掲げることができる。The aryldihalosilane used as a raw material for use in the present invention is not particularly limited; conventionally known ones may be suitably employed as they are. Compounds that are a combination of these are preferred. In other words, aryl groups include phenyl groups, alkali groups such as tolyl and ethylphenyl groups, halogenated phenyl groups such as chlorophenyl and fluorophenyl groups, trifluoromethyl groups, phenoxyphenyl groups, and biphenyl groups. Examples include groups or groups substituted with alkyl and/or halogen. Further, as the halogen group, a chlorine atom is most preferable, but a bromine atom and a fluorine atom can also be mentioned.
本発明の不均化反応に用いる触媒は従来公知のものとし
てハロゲン化金属ルイス酸化合物が用いろるが、そのほ
かアリール金属ルイス酸化合物も好適に用いつる。ただ
し、本発明は減圧化に実施するところに特徴があること
から、減圧下でも反応系から除去され難い触媒物質を用
いることが当然に望ましい、これらの触媒を例示すると
、三塩化アルミニウムや三臭化アルミニウムの如きハロ
ゲン化アルミニウム、トリフェニルボランやトリトルイ
ルボランなどのアリールボラン類を掲げることができる
。これらの触媒の使用竜は、原料のアリールジハロシラ
ンに対し0.0001〜10重重%が採用でき、通常は
0.01〜5重都%が好ましい。The catalyst used in the disproportionation reaction of the present invention may be a conventionally known metal halide Lewis acid compound, but aryl metal Lewis acid compounds may also be suitably used. However, since the present invention is characterized in that it is carried out under reduced pressure, it is naturally desirable to use a catalyst substance that is difficult to remove from the reaction system even under reduced pressure. Examples include aluminum halides such as aluminum chloride, and arylboranes such as triphenylborane and tritolylborane. These catalysts can be used in an amount of 0.0001 to 10% by weight, preferably 0.01 to 5% by weight, based on the raw material aryldihalosilane.
本発明における不均化反応の方法は、減圧条件というこ
とを除けば従来公知の方法がそのまま好適に採用しうる
。すなわち、原料のアリールジハロシランと触媒を反応
器に仕込んで加熱撹拌するバッチ反応方式が最も好適で
あるが、上記の原料と触媒とをそれぞれ独立に、または
混合体として反応管中を流通させながら反応させる流通
反応方式も採用している。As the method for the disproportionation reaction in the present invention, conventionally known methods can be suitably employed as they are, except that the reaction is performed under reduced pressure conditions. In other words, the most suitable method is a batch reaction method in which the raw material aryldihalosilane and the catalyst are charged into a reactor and heated and stirred. A flow reaction method is also adopted in which the reaction is carried out while the reaction is being carried out.
反応温度は、原料のアリールジハロシランの種類や触媒
によっても最適値は異なるが、より重要な作用因子が減
圧の程度にあることから特に限定されず、通常はf50
℃以上の条件が採用される。The optimum reaction temperature varies depending on the type of aryldihalosilane used as a raw material and the catalyst, but since the more important factor is the degree of pressure reduction, it is not particularly limited, and is usually set at f50.
℃ or higher conditions are adopted.
反応時間も特に限定されないが、数10分〜lO数時間
の範囲が一般的である。The reaction time is also not particularly limited, but is generally in the range of several tens of minutes to several hours.
本発明の最も重要な条件は、減圧下ということである。The most important condition of the present invention is that it is carried out under reduced pressure.
基本的には減圧の程度が上がれば、それだけ不均化反応
が促進されるが、原料のアリールジハロシランが液相中
に溶存する触媒と十分に接触しうろことも不均化反応の
重要な条件であって、減圧の程度にも限度がある。その
限度は、アリ−ジハロシランの種類や反応温度によって
も異なるが、通常はO,0OITorr以上、好ましく
は0、’0ITorr以上である。この限六内の減圧に
あっては、減圧のもたらす効果の□程度は、同一温度下
の減圧度の高い側におけるほど顕著になるという特徴が
みられ、また高温下で減圧度が低い条件よりも低温下で
減圧度が高い条件の方がはるかに目的のジアリールジハ
ロシランを高収率に与えるという傾向がしばしばみられ
、一般に30〜300℃で0.01〜600To r
r、好ましくは50〜200℃で0.1〜400Tor
rである。Basically, the higher the degree of reduced pressure, the more the disproportionation reaction is accelerated, but it is also important that the raw material aryldihalosilane comes into sufficient contact with the catalyst dissolved in the liquid phase. There are also limits to the degree of pressure reduction. The limit varies depending on the type of ary-dihalosilane and the reaction temperature, but is usually 0,0 OITorr or more, preferably 0,'0ITorr or more. When reducing pressure within this limit, there is a characteristic that the effect of reduced pressure becomes more pronounced as the degree of reduced pressure is higher at the same temperature, and that it becomes more pronounced under conditions of lower pressure reduction at high temperatures. However, there is often a tendency to obtain the desired diaryldihalosilane in a much higher yield under conditions of a high degree of vacuum at low temperatures;
r, preferably 0.1 to 400 Torr at 50 to 200°C
It is r.
[作用]
本発明のアリールジハロシランの不均化反応において、
減圧という条件が何故に大きな効果を持つのかというこ
とについて本発明者らは以下の如く推測している。[Function] In the aryldihalosilane disproportionation reaction of the present invention,
The present inventors speculate as follows as to why the condition of reduced pressure has such a great effect.
上記の不均化反応をフェニルジクロルシラン(PhSi
(H)C1lzと示す)を原料とする場合を例にとりあ
げると、この反応ではド弐の2PhSi (H)CQ
4’ 7=P h 2 S i CQ 2 + H2
S i CQ、 2如く目的物はジフェニルジクロルシ
ラン(Ph2S i CQ zと示す)である、この反
応は本来、平衡反応であると思われるので、仮に反応が
平衡状態に到達していればジフェニルジクロルシランの
生成量はある量で一定にとなり、それ以上の生成量の増
大は期待できない、したがって、副生ずるジクロルシラ
ン(H2SiCQ、2と示す)を系外に抜き出すことが
上記の生成酸の増大に必要と思われるが、ジクロルシラ
ンの沸点は常圧で8℃ときわめて低いために、例えばフ
ェニルジクロシランの沸点近辺の185℃という高温下
で不均化反応をさせれば、当然ジクロルシランは反応液
相から容易に除去されるものと期待される。しかるに、
185℃という高温にもかかわらず不均化反応はそれほ
ど進行しない。一方、減圧の効果が現実に顕著に存在す
るわけであるから、逆に推測すると、1115℃という
高温であっても常圧では除去され難いジクロルシランが
液相中に存在している可能性がある。しかも、反応温度
が80℃程度の低温であっても、減圧が数Torrの高
減圧度の条件の方が不均化反応がより速やかに進むこと
から、不均化反応の正逆反応速度そのものは低温でも相
当大きいものの、反応の平衡定数はきわめて小さく、そ
のために極少量でもジクロルシランが液相中に存在する
ことは、ジフェニルジクロルシランの生成機の増大を著
しく妨げる作用をしていると推測される。The above disproportionation reaction was carried out using phenyldichlorosilane (PhSi
(H)C1lz) is used as a raw material. In this reaction, 2PhSi (H)CQ
4' 7=P h 2 S i CQ 2 + H2
As shown in S i CQ, 2, the target product is diphenyldichlorosilane (denoted as Ph2S i CQ z).This reaction is originally considered to be an equilibrium reaction, so if the reaction had reached an equilibrium state, diphenyldichlorosilane The amount of dichlorosilane produced becomes constant at a certain amount, and no further increase can be expected. Therefore, extracting the by-product dichlorosilane (H2SiCQ, denoted as 2) from the system will increase the amount of acid produced. However, since the boiling point of dichlorosilane is extremely low at 8°C at normal pressure, if the disproportionation reaction is carried out at a high temperature of 185°C, which is around the boiling point of phenyldichlorosilane, dichlorosilane will naturally dissolve in the reaction liquid. It is expected that it will be easily removed from the phase. However,
Despite the high temperature of 185°C, the disproportionation reaction does not proceed much. On the other hand, since the effect of reduced pressure is actually noticeable, conversely, it is possible that dichlorosilane, which is difficult to remove at normal pressure even at a high temperature of 1115°C, exists in the liquid phase. . Moreover, even if the reaction temperature is as low as 80°C, the disproportionation reaction proceeds more quickly under conditions of high vacuum of several Torr, so the forward and reverse reaction rate of the disproportionation reaction is the same. is quite large even at low temperatures, but the equilibrium constant of the reaction is extremely small, so it is assumed that the presence of even a very small amount of dichlorosilane in the liquid phase has the effect of significantly inhibiting the increase in the production of diphenyldichlorosilane. be done.
[実施例]
次に、本発明を実施例により説明し、さらにその効果な
明らかにする目的から比較例も掲げるが、本発明はこれ
らの実施例に限定されるものではない。[Examples] Next, the present invention will be explained by examples, and comparative examples will also be given for the purpose of clarifying its effects, but the present invention is not limited to these examples.
実施例1〜7
還流冷却器付きの内容ffl100m化のパイルレック
スフラスコにフェニルジクロルシラン1O1Ogおよび
触媒として三塩化アルミニウム0.1gを入れ、オイル
バスにて第1表に掲げる反応温度、反応時間および減圧
度の条件下で不均化反応を実施した6反応終了後、反応
液の組成をガスクロマトグラフィーにて分析した結果、
第1表に掲げる収率でジフェニルジクロルシランが生成
していることを確認した。なお、ここでいう収率は原料
のフェニルジクロルシランのすべてがジフェニルジクロ
シランとクロルシランに変化した場合を100%とする
基準で計算したものである。Examples 1 to 7 1O1Og of phenyldichlorosilane and 0.1g of aluminum trichloride as a catalyst were placed in a Pile Rex flask with a reflux condenser and a capacity of 100 m, and the reaction temperature, reaction time, and After completing the six disproportionation reactions under reduced pressure conditions, the composition of the reaction solution was analyzed using gas chromatography.
It was confirmed that diphenyldichlorosilane was produced at the yield shown in Table 1. Note that the yield here is calculated on the basis of 100% when all of the raw phenyldichlorosilane is converted into diphenyldichlorosilane and chlorosilane.
第1表
比較例1−4
実施例1〜7と全く同じ装置およびフェニルジクロルシ
ラン10.0gと三塩化アルミニウム0゜1gを用いて
、大気圧下に第2表に掲げる反応温度と時間で不均化反
応を実施した0反応終了後、反応液の組成をガスクロマ
トグラフィーにて分析した結果、第2表に掲げる収率で
ジフェニルジクロルシランが生成していることを確認し
た。Table 1 Comparative Example 1-4 Using exactly the same equipment as in Examples 1 to 7 and 10.0 g of phenyldichlorosilane and 0.1 g of aluminum trichloride, the reaction was carried out at the reaction temperature and time listed in Table 2 under atmospheric pressure. After the completion of the disproportionation reaction, the composition of the reaction solution was analyzed by gas chromatography, and as a result, it was confirmed that diphenyldichlorosilane was produced at the yield listed in Table 2.
第2表
実施例8
実施例1〜7と全く同じ装置を用い、フェニルジクロル
シラン10.0gと触媒としてトリフェニルボラン0.
1gをフラスコに入れ、100℃、10 T l) r
rにて7時間の不均化反応を実施し、実施例1〜7と
同様の方法で反応後の液の組成を分析した結果、ジフェ
ニルジクロルシランの収率は71.2%であった。Table 2 Example 8 Using exactly the same equipment as in Examples 1 to 7, 10.0 g of phenyldichlorosilane and 0.0 g of triphenylborane as a catalyst were added.
Put 1 g into a flask, heat at 100°C, 10 Tl) r
The disproportionation reaction was carried out for 7 hours at r, and the composition of the liquid after the reaction was analyzed in the same manner as in Examples 1 to 7. As a result, the yield of diphenyldichlorosilane was 71.2%. .
実施例5)
実施例1〜7と全く同じ装置を用い、バラートルイルジ
クロルシラン10.0gと触媒としてトリフェニルボラ
ン0.1gをフラスコに入れ、80℃、2Torrにて
6時間の不均化反応を実施した0反応後の液の組成をガ
スクロマトグラフィーにて分析した結果、ジ−バラ−ト
ルイルジクロルシランの収率は87.5%であった。Example 5) Using exactly the same equipment as in Examples 1 to 7, 10.0 g of balatolyldichlorosilane and 0.1 g of triphenylborane as a catalyst were placed in a flask, and disproportionation was carried out at 80°C and 2 Torr for 6 hours. As a result of analyzing the composition of the liquid after the reaction by gas chromatography, the yield of di-bala-tolyldichlorosilane was 87.5%.
[発明の効果]
以ヒの説明より理解されるように、本発明によれば目的
とするジアリールジハロシランを低温下でも極めて高収
率に得ることができる。[Effects of the Invention] As will be understood from the following explanation, according to the present invention, the desired diaryldihalosilane can be obtained in extremely high yield even at low temperatures.
Claims (1)
に行うことを特徴とするジアリールジハロシランの製造
方法。1. A method for producing diaryldihalosilane, characterized in that the disproportionation reaction of aryldihalosilane is carried out under reduced pressure conditions.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10684186A JPS62263189A (en) | 1986-05-12 | 1986-05-12 | Production of diaryldihalosilane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10684186A JPS62263189A (en) | 1986-05-12 | 1986-05-12 | Production of diaryldihalosilane |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS62263189A true JPS62263189A (en) | 1987-11-16 |
Family
ID=14443904
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10684186A Pending JPS62263189A (en) | 1986-05-12 | 1986-05-12 | Production of diaryldihalosilane |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62263189A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5110974A (en) * | 1991-10-24 | 1992-05-05 | Dow Corning Corporation | Thermal disproportionation of arylhalosilanes |
US5126472A (en) * | 1991-11-12 | 1992-06-30 | Dow Corning Corporation | Thermal disproportionation of organooxysilanes |
US5126471A (en) * | 1991-11-14 | 1992-06-30 | Dow Corning Corporation | Thermal disproportionation of cycloalkylsilanes |
US5136070A (en) * | 1991-12-23 | 1992-08-04 | Dow Corning Corporation | Sodium borohydride catalyzed disproportionation of cycloorganosilanes |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2746981A (en) * | 1952-09-26 | 1956-05-22 | Union Carbide & Carbon Corp | Disproportionation of aryldichlorosilanes |
-
1986
- 1986-05-12 JP JP10684186A patent/JPS62263189A/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2746981A (en) * | 1952-09-26 | 1956-05-22 | Union Carbide & Carbon Corp | Disproportionation of aryldichlorosilanes |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5110974A (en) * | 1991-10-24 | 1992-05-05 | Dow Corning Corporation | Thermal disproportionation of arylhalosilanes |
US5126472A (en) * | 1991-11-12 | 1992-06-30 | Dow Corning Corporation | Thermal disproportionation of organooxysilanes |
US5126471A (en) * | 1991-11-14 | 1992-06-30 | Dow Corning Corporation | Thermal disproportionation of cycloalkylsilanes |
US5136070A (en) * | 1991-12-23 | 1992-08-04 | Dow Corning Corporation | Sodium borohydride catalyzed disproportionation of cycloorganosilanes |
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