JPH0656855A - Silane compound and its production - Google Patents

Abstract

PURPOSE:To provide the new silane compound useful as a component of a propylene polymerization catalyst, a silane coupling agent, etc. CONSTITUTION:Tert-amyloxy-n-propyldiethoxysilane of the formula. The compound of the formula can be obtained by reacting an n-propyltrihalosilane with tert-amyl alcohol and then reacting the resultant product with ethanol.

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 alkoxysilanes as a catalyst component. ing. 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 provides the following formula (I):

[0006]

[Chemical 2] To provide tert-amyloxy-n-propyldiethoxysilane.

This silane compound (I) has a boiling point of 98 ° C. /
It is 23 mmHg. The structure of this silane compound is GC-M
It can be confirmed by S, ¹ H-NMR, infrared absorption spectrum (IR) and the like.

For example, when the compound (I) is analyzed by using ¹ H-NMR, n-propyl group at δ = 0.4 to 2.2,
A signal of a hydrogen atom based on the tert-amyl group and a portion of the ethoxy group excluding the carbon atom directly bonded to the oxygen atom was observed, and at δ = 3.9, the oxygen atom of the ethoxy group was directly bonded to the oxygen atom. The signal of a hydrogen atom attached to a carbon atom is observed.

Further, from the analysis by IR spectrum,
A large absorption due to the SiOC bond is 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, n-
A silane compound of the above formula (I) is produced by reacting propyltrihalosilane with tert-amyl alcohol and then reacting the obtained reaction product with ethanol. The raw material n-propyltrihalosilane has the following formula (II):

[0013]

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

[0014]

[Chemical 4] At this time, trihalosilane 0.9-
Use 1.1 moles. The reaction conditions are, for example, temperature 1
At a temperature of 00 to 200 ° C for 10 minutes to 10 hours, it is recommended to use a platinum-based catalyst such as chloroplatinic acid, platinum-1,1,3,3-tetramethyl-1,3-divinyldisiloxane complex, etc. preferable. A solvent can also be used, and examples thereof include benzene and toluene. n-Propyltrihalosilane is commercially available, and those commercially available products can be used in the present invention.

In the present invention, the above n-propyltrihalosilane (II) is reacted with tert-amyl alcohol. t
ert-Amyl alcohol itself is known and commercially available. The reaction between the two may proceed as follows:

[0016]

[Chemical 5] (In the above formula and below, t-Amyl represents a tert-amyl group) By this reaction, the compound (III) is produced.

When carrying out the above reaction B, 1 to 3 mol of tert-amyl alcohol is used with respect to 1 mol of n-propyltrihalosilane (II). The reaction is, for example, 20-100
It is carried out at a temperature of ℃ for 10 minutes to 5 hours, preferably at a temperature of 40 to 70 ℃ 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,
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 1-1.1 to 1 mol of n-propyltrihalosilane.
It is preferably used in an amount of 5 mol.

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

[0020]

[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,
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, n-propyltriethoxysilane and t
A method of producing a compound of formula (I) by transesterifying ert-amyl alcohol:

[0024]

[Chemical 7] In the above reaction formula, relative to 1 mol of compound (IV),
1 to 20 mol of tert-amyl alcohol are used. The reaction is performed, for example, at a temperature of 0 to 150 ° C. for 10 minutes to 30 hours. At the time of this alkoxyl group exchange reaction, an acid,
For example, a trifluoroborane-ether complex, toluenesulfonic acid, or a compound that reacts with an alcohol to generate an acid, such as trimethylchlorosilane; or a base, for example, an alkali metal alkoxide, a metal hydroxide, or the like can be used.

The starting material, n-propyltriethoxysilane (IV), can be produced by the reaction of n-propyltrichlorosilane and ethanol to produce hydrogen chloride.

[0026]

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

[0027]

Example 1 Preparation of tert-amyloxy-n-propyldiethoxysilane
(1) 500 ml equipped with magnetic stirrer, reflux condenser and dropping funnel
Into a three-necked flask, the commercially available product n-propyltrichlorosilane (32.2 g, 0.181 mol) and hexane (300 ml) was charged, and a mixture of pyridine (46.0 g, 0.58 mol) and tert-amyl alcohol (23.8 g, 0.27 mol) was added to the flask. Was added dropwise at room temperature with stirring for 30 minutes.

After heating under reflux for 2 hours, ethanol is added here.
23.7 g (0.51 mol) was added, and reflux was continued for another 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.
28.0 g (0.112 mol) of liquid at 98 ° C / 23 mmHg was obtained. The product was confirmed to be tert-amyloxy-n-propyldiethoxysilane by GC-MS, ¹ H-NMR and IR.
Confirmed by. ^{The 1} H-NMR and IR measurement results are shown in FIGS. 1 and 2, respectively. The yield was 62%.

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

¹ H-NMR measuring device: HITACHI R-1500 (manufactured by Hitachi Ltd.),
Measurement solvent: C ₆ D ₆ , standard substance: C ₆ H ₆ (δ = 7.24) IR measurement device: 1600 series FT-IR (manufactured by Perkin Elmer) Measurement method: Liquid film method (KBr plate) GC-MS HP 5970B (manufactured by Hewlett-Packard Co.) was used and the measurement results were as follows: m / e (spectral intensity ratio): 63 (36), 79 (26),
91 (22), 119 (28), 135 (100), 161 (64), 219 (48).

[0032]

Example 2 Preparation of tert-amyloxy-n-propyldiethoxysilane
(2) In a 200 ml three-necked flask equipped with a magnetic stirrer and a reflux condenser, n-propyltriethoxysilane 10.0 g (0.0487
Mol), 50.2 g (0.570 mol) of tert-amyl alcohol and 0.101 g (1.49 mmol) of sodium ethoxide were charged, and the reaction was carried out by stirring in an oil bath at 105 ° C. for 24 hours. Then, by adding trimethylchlorosilane to neutralize the alkali, and then by vacuum distillation, tert-
Amyloxy-n-propyldiethoxysilane 8.70g (0.
0351 mol) was obtained. The structure was confirmed in the same manner as in Example 1. The yield was 72%.

[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 tert-amyloxy-n-propyldiethoxysilane produced in Example 1. The curve above the peak and the numerical value below the peak indicate the area intensity of each peak.

FIG. 2 is an IR chart of tert-amyloxy-n-propyldiethoxysilane produced in Example 1.

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 n-propyltrihalosilane is reacted with tert-amyl alcohol, and then the obtained reaction product is reacted with ethanol. 3. n-Propyltriethoxysilane and tert-
The method for producing a silane compound according to claim 1, wherein a tert-amyloxy group is introduced into the silane compound by an alcohol exchange reaction of amyl alcohol.