JPH05279372A - Silane compound and method for producing the same - Google Patents

Abstract

(57) [Summary] [Object] To provide sec-butoxycyclopentyldiethoxysilane, which is a novel silane compound, and a method for producing the same. [Structure] The above silane compound is produced by reacting cyclopentyltrihalosilane with sec-butanol and then reacting the obtained reaction product with ethanol, or by subjecting cyclopentyltriethoxysilane and sec-butanol to an alcohol exchange reaction. To be done.

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 In propylene polymerization, it has hitherto been known that a polymer having high stereoregularity can be produced by using an alkoxysilane as a catalyst component. ing. However, even if propylene is polymerized using a catalyst component produced using a conventionally known alkoxysilane or the like, it is not possible to sufficiently satisfy both high polymerization activity and high stereoregularity.

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 provides the following formula (I):

[0006]

[Chemical 2] (Wherein sec-Bu represents a sec-butyl group and Et represents an ethyl group), that is, sec-butoxycyclopentyldiethoxysilane.

This silane compound (I) has a boiling point of 130 ° C.
/ 20 mmHg. The structure of this silane compound is GC-
It can be confirmed by MS, ¹ H-NMR, infrared absorption spectrum (IR) and the like.

For example, when the compound (I) is analyzed by using ¹ H-NMR, the carbon atom directly bonded to the oxygen atom of the cyclopentyl group and the ethoxy group and the sec-butoxy group at δ = 0.5 to 2.2. A hydrogen atom signal based on the part excluding the atoms was observed, and δ = 3.5 to 4.1.
A signal of a hydrogen atom bonded to a carbon atom directly bonded to an oxygen atom of the ethoxy group and the sec-butoxy group was observed.

From the analysis by IR spectrum,
A large absorption based on the SiOC bond was observed near 1100 cm ^-1 .

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

Since this 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 sec-butanol, and then the obtained reaction product is reacted with ethanol to produce the silane compound of the above formula (I). The raw material cyclopentyltrihalosilane has the following formula:

[0013]

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

[0014]

[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 sec-butanol:

[0016]

[Chemical 5] When carrying out this reaction, 1 to 3 mol of cyclopentyltrihalosilane (II) is used and 1 to 3 mol of sec-butanol is used. The reaction is carried out, for example, at a temperature of 20 to 100 ° C for 10 minutes to 5 minutes.
It is carried out at a temperature of 40 to 70 ° C. for 30 minutes to 2 hours. A solvent can also be used, and examples thereof include organic solvents such as hexane, ether, petroleum ether, and benzene.

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,
Examples thereof include 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
1-1 for 1 mol of cyclopentyltrihalosilane.
It is preferably used in an amount of 5 mol.

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

[0019]

[Chemical 6] In this reaction, ethanol is used in an amount of 2 to 3 mol per 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,
Normally, 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, a method for producing a compound of formula (I) by subjecting cyclopentyltriethoxysilane and sec-butanol to an alcohol exchange reaction:

[0023]

[Chemical 7] In the above reaction formula, relative to 1 mol of compound (IV),
Use 1 to 20 mol of sec-butanol. The reaction is carried out, for example, at a temperature of 0 to 150 ° C. for 10 minutes to 20 hours. In this alkoxyl group exchange reaction, as a catalyst, an acid, for example, a trifluoroborane-ether complex and toluenesulfonic acid, or a compound such as trimethylchlorosilane that reacts with an alcohol to generate an acid; or a base, for example, an alkali metal Alkoxides, metal hydroxides and the like can be used.

The starting material cyclopentyltriethoxysilane (IV) can be produced by the reaction of cyclopentyltrichlorosilane and ethanol to produce hydrogen chloride.

[0025]

The present invention will be described in more detail by the following examples.

[0026]

Example 1 Production of sec-butoxycyclopentyldiethoxysilane
(1) Cyclopentene 15.0 g (0.220 mol), trichlorosilane 26.9 g (0.198 mol) and 0.077 in a 100 ml pressure vessel.
Charge 25 μl of a mmol / ml chloroplatinic acid solution in isopropyl alcohol (platinum content 1.92 × 10 ^-6 mol) at 150 ° C.
Cyclopentyltrichlorosilane was quantitatively obtained by stirring 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 53.1 g (0.67 mol) of pyridine and sec-butanol
22.6 g (0.30 mol) of the mixture was added dropwise at room temperature with stirring for 30 minutes.

After heating under reflux for 2 hours, ethanol is added here.
26.9 g (0.584 mol) was added, and the mixture was further refluxed for 1 hour and then the reaction was terminated.

The produced salt is removed by filtration, hexane is distilled off, and the residue is distilled under reduced pressure to reduce the boiling point.
37.3 g (0.143 mol) of a liquid having a temperature of 130 ° C./20 mmHg was obtained. It was confirmed by GC-MS, ¹ H-NMR and IR that this product was sec-butoxycyclopentyldiethoxysilane. ^{The 1} H-NMR and IR measurement results are shown in FIGS. 1 and 2, respectively. The yield was 72%.

The ¹ H-NMR and IR were measured under the following conditions.

¹ H-NMR measuring device: HITACHI R-24B (manufactured by Hitachi, Ltd.), measuring solvent: CCl ₄ , standard substance: CHCl ₃ , tetramethylsilane (TMS) IR measuring device: 1600 series FT-IR (Perkin-Elmer Co., Ltd.) Measuring method: Liquid film method (KBr plate) Further, as the GC-MS, HP 5970B (manufactured by Hewlett-Packard Co.) was used, and the measurement results were as follows: m / e (spectrum) Strength ratio): 231 (17), 191 (8
3), 187 (17), 163 (38), 135 (100), 119 (15), 107 (2
0), 79 (30), 63 (28).

[0032]

Example 2 Production of sec-butoxycyclopentyldiethoxysilane
(2) In a 50 ml three-necked flask equipped with a magnetic stirrer and a reflux condenser, 29.6 g (0.127 g) of cyclopentyltriethoxysilane was added.
Mol), sec-butanol 151.1 g (2.04 mol) and sodium ethoxide 286.5 mg (4.21 mmol).
The mixture was stirred in an oil bath at ℃ for 10 hours to react. Then, the alkali was neutralized by adding trimethylchlorosilane, and then vacuum distillation was performed to obtain 24.2 g (0.0931 mol) of sec-butoxycyclopentyldiethoxysilane. The structure was confirmed in the same manner as in Example 1. Yield 73
%Met.

[0033]

The present invention provides 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 ¹ H-NMR chart of sec-butoxycyclopentyldiethoxysilane produced in Example 1.

2 is an IR chart of sec-butoxycyclopentyldiethoxysilane produced in Example 1. FIG.

Claims (3)

[Claims] 1. The following formula (I): (Here, sec-Bu represents a sec-butyl group and Et represents an ethyl group). 2. The method for producing a silane compound according to claim 1, wherein cyclopentyltrihalosilane is reacted with sec-butanol and then the obtained reaction product is reacted with ethanol. 3. Cyclopentyltriethoxysilane and se
The method for producing a silane compound according to claim 1, wherein a sec-butoxy group is introduced into the silane compound by an alcohol exchange reaction of c-butanol.