JPH06345783A - Silane compound and its production - Google Patents

Abstract

PURPOSE:To provide a highly active new compound useful as a catalytic component for obtaining polypropylene of high stereoregularity, a silane coupling agent, etc. CONSTITUTION:The objective compound, cyclopentyl(2-ethoxyethoxy) dimethoxysilane of formula I, which can be obtained by the following process: (A) a cyclopentyltrihalosilane of formula II (X is halogen) is reacted with (B) 2-ethoxyethanol at a molar ratio B/A of >=1-3, in a solvent (e.g. hexane) if needed, pref. in the presence of a hydrogen halide acceptor (e.g. pyridine) at 20-100 deg.C for 10min to 5hr to produce (C) a compound of formula III, which, in turn, is reacted with (D) ethanol at a molar ratio D/C of 2-5 pref. in the presence of the same hydrogen halide acceptor as the above at 0-100 deg.C for 10min to 5hr.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD 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 propylene polymerization catalyst component, a silane coupling agent and the like and a method for producing the same.

[0002]

2. Description of the Related Art It has been conventionally known that a polymer having a high stereoregularity can be produced by using an alkoxysilane as a catalyst component in carrying out propylene polymerization. However, even if propylene is polymerized using a catalyst component produced using a conventionally known alkoxysilane or the like, both high polymerization activity and high stereoregularity cannot be sufficiently satisfied.

Further, the silane compound is expected to be used as a silane coupling agent or a resin modifier, and therefore, a new silane compound is desired to appear.

Therefore, an object of the present invention is to provide a novel silane compound having high activity and high stereoregularity, which is useful as a propylene polymerization catalyst component or a silane coupling agent, and a method for producing the same.

[0005]

The present invention firstly provides the following formula (I):

[0006]

[Chemical 2] A silane compound represented by the following formula, that is, cyclopentyl (2-ethoxyethoxy) dimethoxysilane.

This silane compound (I) has a boiling point of 67 ° C.
/0.1 mmHg. The structure of this silane compound is GC
-MS, ¹ H-NMR, infrared absorption spectrum (IR)
Etc. can be confirmed.

For example, when the compound (I) is analyzed by using ¹ H-NMR, a methyl group bonded to a carbon atom at δ = 1.0 to 1.4, a cyclopentyl group at δ = 1.4 to 2.2, and δ
== 2.9 to 4.4, signals based on the methyl group and methylene group bonded to the oxygen atom were observed.

Further, from the analysis by IR spectrum,
A large absorption due to the SiOC bond was observed near 1100 cm ^-1 .

From the analysis by GC-MS, the following m
/ E (spectral intensity ratio) was observed: 216 (5.21), 17
9 (94.23), 159 (8.17), 151 (77.31), 135 (23.49), 121 (44.5
1), 107 (100), 91 (37.43).

By using this silane compound (I) as a catalyst component, an olefin polymer having high stereoregularity such as polypropylene or polybutene can be produced with high polymerization activity.

Since the silane compound (I) has a hydrolyzable group, it can be used as a silane coupling agent, a polymerizable monomer and a resin modifier.

The present invention secondly provides a method for producing a novel silane compound represented by the above formula (I). That is, the cyclopentyltrihalosilane is reacted with 2-ethoxyethanol, and then the obtained reaction product is reacted with methanol to produce the silane compound of the above formula (I). The raw material cyclopentyltrihalosilane has the following formula:

[0014]

[Chemical 3] (X represents a halogen atom, preferably Cl or B
is r) and can be readily prepared from cyclopentene and trihalosilane (H—SiX ₃ ) by a hydrosilylation reaction:

[0015]

[Chemical 4] At this time, per mol of cyclopentene, trihalosilane
Use 0.9 to 1.1 moles. The reaction conditions are, for example,
The temperature is 100 to 200 ℃, 10 minutes to 10 hours, platinum-based catalyst, such as chloroplatinic acid, platinum-1,1,3,3-tetramethyl-
It is preferable to use a 1,3-divinyldisiloxane complex or the like. A solvent can also be used, and examples thereof include benzene and toluene.

In the present invention, the cyclopentyltrihalosilane (II) thus obtained is reacted with 2-ethoxyethanol:

[0017]

[Chemical 5] When carrying out this reaction, 1-mol of cyclopentyltrihalosilane (II) is mixed with 1 to 3 parts of 2-ethoxyethanol.
Use mol. The reaction is carried out, for example, at a temperature of 20 to 100 ° C for 10 minutes to 5 hours, preferably at a temperature of 40 to 70 ° C for 30 minutes to 2 hours. It is also possible to use solvents, for example hexane,
Organic solvents such as ether, petroleum ether, benzene and the like can be mentioned.

Here, in order to allow the reaction to proceed rapidly, it is preferable to coexist with a hydrogen halide acceptor. As the hydrogen halide acceptor, tertiary amines,
And nitrogen-containing heterocyclic compounds such as pyridine, quinoline, isoquinoline and the like. Of these, pyridine and quinoline are preferably used. The hydrogen halide acceptor is 1 mole to 1 mole of cyclopentyltrihalosilane.
It is preferably used in an amount of .about.1.5 mol.

In the present invention, next, the obtained reaction product (III) is reacted with methanol to produce the above-mentioned silane compound (I) of the present invention.

[0020]

[Chemical 6] In this reaction, 2 to 5 mol of methanol is used with respect to 1 mol of the compound (III). The reaction is carried out at a temperature of 0 to 100 ° C for 10 minutes to 5 hours, preferably at a temperature of 10 to 60 ° C for 30 minutes to 2 hours. Also in the reaction C, it is preferable to coexist with a hydrogen halide acceptor in order to allow the reaction to proceed rapidly. As the hydrogen halide acceptor, the reaction B was previously used.
The hydrogen halide acceptor exemplified in 1) can be used.
The hydrogen halide acceptor used here may be the same as or different from the compound used in the previous reaction,
Usually, the same one is used. The hydrogen halide acceptor is preferably used in an amount of 2 to 3 mol with respect to 1 mol of the compound (III).

Further, in the above-mentioned reaction B and reaction C, by blowing an inert gas, the produced hydrogen halide can be removed from the reaction system to allow the reaction to proceed rapidly.

By the above-mentioned production method, the novel silane compound (I) can be obtained in high yield.

The present invention also provides a method different from the above for producing the silane compound represented by the above formula (I). That is, cyclopentyltrimethoxysilane
A method for producing a compound of formula (I) by transesterification with 2-ethoxyethanol to introduce a 2-ethoxyethoxy group into the silane compound:

[0024]

[Chemical 7] In the above reaction formula, relative to 1 mol of compound (IV),
1 to 20 mol of 2-ethoxyethanol is used. The reaction is
For example, it is carried out at a temperature of 0 to 100 ° C. for 10 minutes to 20 hours. In this alcohol exchange reaction, as a catalyst, an acid, for example, trifluoroborane-ether complex, toluenesulfonic acid, or a compound that reacts with an alcohol to generate an acid,
For example, trimethylchlorosilane; or bases such as alkali metal alkoxides and metal hydroxides can be used.

Cyclopentyltrimethoxysilane (IV) which is a starting material can be produced by a reaction of cyclopentyltrichlorosilane and methanol with generation of hydrogen chloride.

[0026]

The present invention will be described in more detail by the following examples. Example 1 Cyclopentyl (2-ethoxyethoxy) dimethoxysila
(1) Cyclopentene 13.9g (0.204 mol), trichlorosilane 25.1g (0.185 mol) and
Charge 25 μl of 0.077 mmol / ml chloroplatinic acid in isopropyl alcohol (platinum content 1.92 × 10 ⁻⁶ mol),
Cyclopentyl trichlorosilane was quantitatively obtained by stirring at 150 ° C. for 30 minutes.

A 500 ml three-necked flask equipped with a magnetic stirrer, a reflux condenser and a dropping funnel was charged with the cyclopentyltrichlorosilane obtained above and 300 ml of hexane, and 49.3 g (0.623 mol) of pyridine and 2- A mixture of 20.0 g (0.222 mol) of ethoxyethanol was added dropwise at room temperature with stirring for 30 minutes. After refluxing for 2 hours, 18.4 g (0.575 mol) of methanol was added thereto, and refluxing was continued for another hour, and then the reaction was terminated.

The produced salt was removed by filtration, hexane was distilled off, and the residue was distilled under reduced pressure to give a boiling point of 67 ° C./0.1 mmHg (digital vacuum gauge, manufactured by Hayasaka Riko Co., Ltd.,
33.4 g (0.135 mol) of a liquid having a resolution of 0.1 mmHg) was obtained. This product is cyclopentyl (2-ethoxyethoxy) dimethoxysilane, GC-MS, ¹ H
-Confirmed by NMR and IR. ^{The 1} H-NMR and IR measurement results are shown in FIGS. 1 and 2, respectively. The yield was 73%.

¹ H-NMR, IR and GC-M
S was measured under the following conditions.

[0030]¹ H-NMR Measuring device: HITACHI R-1500 (manufactured by Hitachi, Ltd.)
Constant solvent: C₆D₆, Reference material: residual benzeneIR Measuring device: 1600 series FT-IR (Perkin Elmer
(Mfd.) Measuring method: Liquid film method (KBr plate)GC-MS Measuring device: HP 5970B (Hewlett Packard Company
Made)Example 2 Cyclopentyl (2-ethoxyethoxy) dimethoxysila
Manufacturing (2)  100 ml 3-neck flap equipped with magnetic stir bar and reflux condenser
Add 12 g of cyclopentyltrimethoxysilane (6
3.2 mmol), 2-ethoxyethanol 8.7 g (97 mm)
70 mg (1.3 millimolar) and sodium methoxide
Was charged and reacted at room temperature for 3 hours with stirring. That
After that, by adding trimethylchlorosilane,
By neutralizing Lucari and then vacuum distilling,
Lopentyl (2-ethoxyethoxy) dimethoxysilane 1
1.2 g (45 mmol) were obtained. The structure is the same as in Example 1.
And confirmed. The yield was 71%.

[0031]

According to the present invention, it is possible to provide a novel silane compound useful as a propylene polymerization catalyst component, a silane coupling agent and the like, and a method for producing the same.

[Brief description of drawings]

FIG. 1 is a chart showing the result of ¹ H-NMR spectrum analysis of cyclopentyl (2-ethoxyethoxy) dimethoxysilane produced in Example 1.

2 is a chart showing the results of IR spectrum analysis of cyclopentyl (2-ethoxyethoxy) dimethoxysilane produced in Example 1. FIG.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Satoshi Ueki 1-3-3 Nishitsurugaoka, Oi-cho, Iruma-gun, Saitama Tonen Research Institute

Claims (3)

[Claims] 1. The following formula (I): A silane compound represented by. 2. The method for producing a silane compound according to claim 1, wherein cyclopentyltrihalosilane is reacted with 2-ethoxyethanol, and then the obtained reaction product is reacted with methanol. 3. Cyclopentyltrimethoxysilane and 2-
The method for producing a silane compound according to claim 1, wherein a 2-ethoxyethoxy group is introduced into the silane compound by an alcohol exchange reaction with ethoxyethanol.