JPH0710888A - Purification method of dicyclopentyldimethoxy silane - Google Patents
Purification method of dicyclopentyldimethoxy silaneInfo
- Publication number
- JPH0710888A JPH0710888A JP18436193A JP18436193A JPH0710888A JP H0710888 A JPH0710888 A JP H0710888A JP 18436193 A JP18436193 A JP 18436193A JP 18436193 A JP18436193 A JP 18436193A JP H0710888 A JPH0710888 A JP H0710888A
- Authority
- JP
- Japan
- Prior art keywords
- dicyclopentyldimethoxysilane
- methanol
- silane
- purification method
- dicyclopentyldimethoxy
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、例えば、オレフィンの
重合用触媒として用いることのできるジシクロペンチル
ジメトキシシランの精製方法に関し、特にジシクロペン
チルジメトキシシラン中から、不純物として含まれるシ
クロペンチルシクロペントキシジメトキシシランを除去
する方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for purifying dicyclopentyldimethoxysilane which can be used, for example, as a catalyst for olefin polymerization, and more particularly to cyclopentylcyclopentoxydimethoxysilane contained as an impurity in dicyclopentyldimethoxysilane. On how to remove.
【０００２】[0002]
【従来技術】ジシクロペンチルジメトキシシランは、他
の有機珪素化合物や有機珪素からなる基を含む化合物の
製造において、活性の高い基礎原料として屡々用いられ
ている。ジシクロペンチルジメトキシシランは、従来、
シクロペンチルクロライドとマグネシウムから、グリニ
ヤール試薬（シクロペンチルマグネシウムクロライド）
を調製し、これにテトラメトキシシランを反応させるこ
とによって製造されている。しかしながら、この方法で
は、副生成物としてシクロペンチルシクロペントキシジ
メトキシシランが生成し、この副生成物は精留によって
も分離することが難しいために、高純度のジシクロペン
チルジメトキシシシランが得られないという欠点があっ
た。Dicyclopentyldimethoxysilane is often used as a highly active base material in the production of other organosilicon compounds and compounds containing groups of organosilicon. Dicyclopentyldimethoxysilane has traditionally been
From cyclopentyl chloride and magnesium, Grignard reagent (cyclopentyl magnesium chloride)
Is prepared and is reacted with tetramethoxysilane. However, in this method, cyclopentylcyclopentoxydimethoxysilane is produced as a by-product, and since this by-product is difficult to separate even by rectification, high-purity dicyclopentyldimethoxysisilane cannot be obtained. There was a flaw.
【０００３】[0003]
【発明が解決しようとする課題】そこで本発明者らは、
高純度のジシクロペンチルジメトキシシランを得るため
に鋭意検討した結果、メタノール中で強酸と共に攪拌処
理することにより、不純物のシクロペンチルシクロペン
トキシジメトキシシランを、ジシクロペンチルジメトキ
シシランと分離可能な物質に容易に変換することができ
ることを見出し、本発明に到達した。従って、本発明の
目的は、シクロペンチルジメトキシシランの精製方法を
提供することにある。Therefore, the present inventors have found that
As a result of diligent studies to obtain high-purity dicyclopentyldimethoxysilane, it was possible to easily convert the impurity cyclopentylcyclopentoxydimethoxysilane into a substance separable from dicyclopentyldimethoxysilane by stirring with methanol and a strong acid. The inventors have found that they can be done, and have reached the present invention. Therefore, an object of the present invention is to provide a method for purifying cyclopentyldimethoxysilane.
【０００４】[0004]
【課題を解決するための手段】本発明の目的は、不純物
としてシクロペンチルシクロペントキシジメトキシシラ
ンを含有するジシクロペンチルジメトキシシランをメタ
ノール中で強酸と共に攪拌した後、残存するメタノール
を留去し、次いで蒸留精製することを特徴とするジシク
ロペンチルジメトキシシランの精製方法によって達成さ
れた。The object of the present invention is to stir dicyclopentyldimethoxysilane containing cyclopentylcyclopentoxydimethoxysilane as an impurity in methanol with a strong acid, distill off the residual methanol and then distill it. It was achieved by a method for purifying dicyclopentyldimethoxysilane, characterized in that it is purified.
【０００５】本発明で用いられる強酸としては、塩酸、
燐酸、硫酸、ＣＦ3 ＣＯＯＨ、ＣＦ3 ＳＯ3 Ｈなどが挙
げられる。使用する強酸の量は、ジシクロペンチルジメ
トキシシランに対して、０．０１〜１０重量％、好まし
くは０．０５〜１重量％である。使用するメタノールの
量は、ジシクロペンチルジメトキシシランの重量の０．
１〜１００倍、好ましくは０．５〜１０倍である。The strong acid used in the present invention is hydrochloric acid,
Examples thereof include phosphoric acid, sulfuric acid, CF 3 COOH, CF 3 SO 3 H and the like. The amount of strong acid used is 0.01 to 10% by weight, preferably 0.05 to 1% by weight, based on dicyclopentyldimethoxysilane. The amount of methanol used was 0. 0 of the weight of dicyclopentyldimethoxysilane.
It is 1 to 100 times, preferably 0.5 to 10 times.
【０００６】処理温度は、−７０〜１５０℃の範囲、好
ましくは、−３０〜７０℃の範囲であり、処理時間は、
０．５〜３０時間である。処理終了後、残存するメタノ
ールを留去したのち残留分を蒸留精製することにより、
目的とするジシクロペンチルジメトキシシランを９９％
以上の純度で得ることができる。The processing temperature is in the range of -70 to 150 ° C, preferably in the range of -30 to 70 ° C, and the processing time is
It is 0.5 to 30 hours. After the treatment is completed, the residual methanol is distilled off and the residue is purified by distillation,
99% of the target dicyclopentyldimethoxysilane
It can be obtained with the above purity.
【０００７】本発明において、従来技術により合成し
た、シクロペンチルシクロペントキシジメトキシシラン
を不純物として含んだジシクロペンチルジメトキシシラ
ンを、高純度のジシクロペンチルジメトキシシランとす
ることができる理由は、不純物であるシクロペンチルシ
クロペントキシジメトキシシランが、強酸の触媒作用で
メタノールと反応し、容易にシクロペンチルトリメトキ
シシランとなる一方、目的物のジシクロペンチルジメト
キシシランは、メタノール中において強酸の作用を受け
難いためと考えられる。In the present invention, the reason why dicyclopentyldimethoxysilane synthesized by the prior art and containing cyclopentylcyclopentoxydimethoxysilane as an impurity can be made into a high-purity dicyclopentyldimethoxysilane is that cyclopentylcyclohexyl which is an impurity. It is considered that pentoxydimethoxysilane reacts with methanol by the catalytic action of a strong acid to easily become cyclopentyltrimethoxysilane, while dicyclopentyldimethoxysilane, which is the target, is hardly affected by the action of a strong acid in methanol.
【０００８】[0008]
【発明の効果】本発明によれば、従来の方法で製造され
たジシクロペンチルジメトキシシラン中の不純物を容易
に除去することができるので、本発明は極めて有意義で
ある。According to the present invention, the impurities in dicyclopentyldimethoxysilane produced by the conventional method can be easily removed, so the present invention is extremely significant.
【０００９】[0009]
【実施例】以下、実施例により本発明を更に具体的に説
明するが、本発明はこれによって限定されるものではな
い。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.
【００１０】実施例１．マグネシウム５３．５ｇ（２．
２０モル）を含有するテトラヒドロフラン２００ｍｌ溶
液中に、シクロペンチルクロライド２３０ｇ（２．２０
モル）を含有するテトラヒドロフラン５００ｍｌ溶液
を、６５℃で１時間かけて滴下した後、７０〜７５℃で
２時間加熱し、グリニヤール試薬を作製した。得られた
グリニヤール試薬に、テトラメトキシシラン１５２ｇ
（１．００モル）を溶解したテトラヒドロフラン３００
ｍｌ溶液を、７５℃で１時間かけて滴下した。滴下終了
後、７５℃で６時間加熱・熟成し、生成した塩を濾過に
より分離した。Embodiment 1. 53.5 g of magnesium (2.
In a solution of 200 ml of tetrahydrofuran containing 20 mol), 230 g of cyclopentyl chloride (2.20
A 500 ml solution of tetrahydrofuran containing (mol) was added dropwise at 65 ° C over 1 hour and then heated at 70 to 75 ° C for 2 hours to prepare a Grignard reagent. 152 g of tetramethoxysilane was added to the obtained Grignard reagent.
Tetrahydrofuran 300 in which (1.00 mol) is dissolved
The ml solution was added dropwise at 75 ° C. over 1 hour. After completion of the dropping, the mixture was heated and aged at 75 ° C. for 6 hours, and the produced salt was separated by filtration.
【００１１】濾液から溶媒のテトラヒドロフランを留去
した後、蒸留塔を用いて精留したところ、沸点１０３℃
／５ｍｍＨｇの物質２１９ｇを得た。得られた物質を分
析したところ、目的とするジシクロペンチルジメトキシ
シランの純度は、９１．８％であり、不純物としてシク
ロペンチルシクロペントキシジメトキシシランが８．２
％含まれていた。この混合物をさらに精留により分離し
ようと試みたが、もはや純度を高めることが不可能であ
ることが確認された。After distilling off the solvent tetrahydrofuran from the filtrate, it was rectified using a distillation column and found to have a boiling point of 103 ° C.
219 g of a substance of / 5 mmHg was obtained. When the obtained substance was analyzed, the purity of the target dicyclopentyldimethoxysilane was 91.8%, and cyclopentylcyclopentoxydimethoxysilane was 8.2 as an impurity.
% Was included. Attempts were made to further separate this mixture by rectification, but it was determined that it could no longer be purified.
【００１２】次に、シクロペンチルシクロペントキシジ
メトキシシランを不純物として含有する、純度９１．８
％の前記ジシクロペンチルジメトキシシラン１００ｇ
と、メタノール１００ｇ及びＣＦ3 ＳＯ3 Ｈ０．３ｇと
を、６５℃で２時間、加熱・攪拌した。残存したメタノ
ールを留去した後、蒸留塔を用いて精留したところ、沸
点１０３℃／５ｍｍＨｇの物質８９ｇを得た。得られた
物質を分析したところ、目的のジシクロペンチルジメト
キシシランが９９．９％と、純度が非常に高くなったこ
とが確認された。Next, cyclopentylcyclopentoxydimethoxysilane is contained as an impurity and has a purity of 91.8.
% Of said dicyclopentyldimethoxysilane 100 g
And 100 g of methanol and 0.3 g of CF 3 SO 3 H were heated and stirred at 65 ° C. for 2 hours. After distilling off the remaining methanol, rectification was carried out using a distillation column to obtain 89 g of a substance having a boiling point of 103 ° C./5 mmHg. When the obtained substance was analyzed, it was confirmed that the target dicyclopentyldimethoxysilane had an extremely high purity of 99.9%.
【００１３】実施例２．実施例１で従来法に基づいて合
成した、純度９１．８％のジシクロペンチルジメトキシ
シラン１００ｇと、メタノール５０ｇ及びＣＦ3 ＣＯＯ
Ｈ０．１ｇとを、６５℃で３時間加熱・攪拌した。残存
したメタノールを留去した後、蒸留塔を用いて精留した
ところ、沸点１０３℃／５ｍｍＨｇの物質８７ｇを得
た。この物質を分析したところ、目的のジシクロペンチ
ルジメトキシシランの純度が９９．９％と非常に高くな
ったことが確認された。これらの実施例は、本発明によ
って、従来になく高純度のジシクロペンチルジメトキシ
シランを得ることができることを実証するものである。Example 2. 100 g of dicyclopentyldimethoxysilane having a purity of 91.8% synthesized according to the conventional method in Example 1, 50 g of methanol and CF 3 COO
0.1 g of H was heated and stirred at 65 ° C. for 3 hours. After distilling off the residual methanol, rectification was carried out using a distillation column to obtain 87 g of a substance having a boiling point of 103 ° C./5 mmHg. Analysis of this material confirmed that the desired dicyclopentyldimethoxysilane had a very high purity of 99.9%. These examples demonstrate that the present invention makes it possible to obtain dicyclopentyldimethoxysilane of unprecedentedly high purity.
Claims (1)
トキシジメトキシシランを含有するジシクロペンチルジ
メトキシシランをメタノール中で強酸と共に攪拌した
後、残存するメタノールを留去し、次いで蒸留精製する
ことを特徴とするジシクロペンチルジメトキシシランの
精製方法。1. Dicyclopentyldimethoxysilane containing dicyclopentylcyclopentoxydimethoxysilane, which contains cyclopentylcyclopentoxydimethoxysilane as an impurity, in methanol with a strong acid, after which the remaining methanol is distilled off and then purified by distillation. Silane purification method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18436193A JP2899504B2 (en) | 1993-06-28 | 1993-06-28 | Purification method of dicyclopentyldimethoxysilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18436193A JP2899504B2 (en) | 1993-06-28 | 1993-06-28 | Purification method of dicyclopentyldimethoxysilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0710888A true JPH0710888A (en) | 1995-01-13 |
| JP2899504B2 JP2899504B2 (en) | 1999-06-02 |
Family
ID=16151898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18436193A Expired - Fee Related JP2899504B2 (en) | 1993-06-28 | 1993-06-28 | Purification method of dicyclopentyldimethoxysilane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2899504B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100376586C (en) * | 2005-11-19 | 2008-03-26 | 江西师范大学 | Impurity removal reaction - process for producing high purity dicyclopentyl dimethoxyl silane |
-
1993
- 1993-06-28 JP JP18436193A patent/JP2899504B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100376586C (en) * | 2005-11-19 | 2008-03-26 | 江西师范大学 | Impurity removal reaction - process for producing high purity dicyclopentyl dimethoxyl silane |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2899504B2 (en) | 1999-06-02 |
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