JPH08151389A - New organic silicon compound - Google Patents

Abstract

PURPOSE: To obtain a new organic silicon compound useful as a Ziegler-Natta catalyst component, a sliane coupling agent, a resin modifier, etc., by reacting iso-pentyltrimethoxysilane with t-butyllithium in hexane. CONSTITUTION: This new organic silicon compound of formula is t-butyl-iso- pentyldimethoxysilane useful as an electron-donating compound of an α-olefin polymerization Ziegler-Natta catalyst system supported on magnesium chloride, a silane coupling agent or a resin modifier. This organic silicon compound can be produced by feeding iso-pentyltrimethoxysilane and dehydrated hexane into a three-neck flask provided with a magnetic stirrer, a Dimroth condenser and a dropping funnel, dropping a pentane solution of t-butyllithium into the flask, refluxing the content under heating, distilling out the solvent and distilling the reaction product under reduced pressure.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organosilicon compound, and more particularly to magnesium chloride-supporting Ziegle.
The present invention relates to a novel organosilicon compound which is useful as an electron donating compound used in producing an α-olefin polymer, particularly polypropylene in an r-Natta catalyst system. The novel organosilicon compound can also be used as a silane coupling agent or a resin modifier.

[0002]

2. Description of the Related Art Ziegler-Natta supporting magnesium chloride
Alkoxysilane compounds are well known as electron donating compounds in the production of α-olefin polymers, especially polypropylene, in catalyst systems. For example, using an organosilicon compound having two hydrocarbon groups having a tertiary carbon atom adjacent to Si as a ligand (EP 0 576 412 A1), Si
A hydrocarbon group having a tertiary carbon atom adjacent to, and an organosilicon compound having a linear hydrocarbon group as a ligand (JP-A-5173319, JP-A-5-202123), Si Using a hydrocarbon group having a tertiary carbon atom adjacent to, and an organosilicon compound having a saturated cyclic hydrocarbon group as a ligand (
There is JP-A-4-227707). However, even with these disclosed techniques, it is not possible to sufficiently increase the stereoregularity of the polypropylene produced. In addition, organosilicon compounds are expected to be used as silane coupling agents or resin modifiers. Therefore, there has been a strong demand for the development of new organosilicon compounds.

[0003]

An object of the present invention is to increase the stereoregularity of an α-olefin polymer produced by using a Ziegler-Natta catalyst supporting magnesium chloride, especially polypropylene, and to improve the silane content. It is an object of the present invention to provide a novel organosilicon compound that can be used as a coupling agent or a resin modifier.

[0004]

The present inventors have developed various electron-donating compounds useful for producing α-olefin polymers, particularly polypropylene, in a magnesium chloride-supported Ziegler-Natta catalyst system. As a result of examining the compound, the chemical formula

Embedded image It was found that it is possible to increase the stereoregularity of polypropylene produced by using tert-butyl-iso-pentyldimethoxysilane represented by the formula (3) as an electron-donating compound, and completed the present invention. The novel organosilicon compound can also be used as a silane coupling agent or a resin modifier.

Chemical formula in the present invention

Embedded image Various synthetic methods can be used for the production of tert-butyl-iso-pentyldimethoxysilane represented by

For example, iso-pentyltrichlorosilane,
tert- by reacting with tert-butyllithium
Obtaining butyl-iso-pentyldichlorosilane, then
tert-butyl-iso-pentyldichlorosilane 1 mol of dehydrohalogenating agent in the presence of 2 to 10 mol tert-butyl
Butyl-iso-pentyldichlorosilane to 1 mol,
A method for producing tert-butyl-iso-pentyldimethoxysilane by reacting with 2 to 50 mol of methanol,
There is a method for producing tert-butyl-iso-pentyldimethoxysilane by reacting iso-pentyltrimethoxysilane and 1 mol of tert-butyllithium with 1 mol of iso-pentyltrimethoxysilane.

Examples of the dehydrohalogenating agent include urea, tertiary amines and nitrogen-containing heterocyclic compounds such as pyridine, quinoline and isoquinoline. Of these, urea, pyridine and quinoline are preferably used.

The reaction is carried out at a temperature of 0 ° C to 120 ° C for 5 minutes to 50 hours, preferably at a temperature of 20 ° C to 100 ° C for 30 minutes to 6 hours. A solvent can also be used in the production,
Examples thereof include organic solvents such as hydrocarbons such as pentane, hexane, heptane, octane, nonane and decane, ethers such as diethyl ether, dibutyl ether and tetrahydrofuran.

Tert-Butyl-iso thus obtained
-Pentyldimethoxysilane: -Mass spectrometry (EI method) result m / z = 218 (M +)- ¹ H-NMR measured with deuterated chloroform as a solvent (Fig. 1) δ ( ¹ H / ppm): 0.5 (t , 2H), 0.7 (d, 6H), 0.8 (s, 9H), 1.
2 (q, 2H) 1.3 (m, 1H), 3.4 (s, 6H) ¹³ C-NMR measured using deuterated chloroform as a solvent (FIG. 2) δ ( ¹³ C / ppm): 7.373, 19.194, 21.916, 26.338 , 31.0
33, 32.111, 50.819 · Deuterated chloroform as solvent and tetramethylsilane as reference substance for chemical shift ²⁹ Si-NMR (Fig. 3) δ ( ²⁹ Si / ppm):-10.525 From the chemical formula

[Chemical 4] It can be confirmed that it is tert-butyl-iso-pentyldimethoxysilane having a structure shown by.

[0010]

EXAMPLES Next, examples of the present invention will be described. (Example 1) (Synthesis of tert-butyl-iso-pentyldimethoxysilane)
A 500 ml three-necked flask equipped with a magnetic stirrer, Dimroth condenser, and 100 ml dropping funnel was used to synthesize iso- by a known method.
16.32 g (85 mmol) of pentyltrimethoxysilane and 100 ml of hexane that had been distilled and dehydrated in the presence of Na were charged. 50 ml of 1.7 mol / l pentane solution of tert-butyllithium manufactured by Aldrich was added dropwise to this over 1 hour, and after the addition was completed,
The reaction was heated to reflux while tracking the reaction by gas chromatography. The reaction was completed in 1 hour. After cooling, the formed precipitate was filtered off, the solvent was distilled off by a rotary evaporator, and then distilled under reduced pressure to obtain 108-110 ° C / 38mHg.
13.8 g of a colorless transparent liquid of was obtained. GC-MS, ¹ H-NMR, ¹³ C-NM
By R, ²⁹ Si-NMR, this colorless transparent liquid was confirmed to be tert-butyl-iso-pentyldimethoxysilane. As a result of calculation, the reaction yield was 74.3 (%). (Preparation of magnesium chloride supported Ziegler-Natta catalyst)
Anhydrous magnesium chloride (obtained by baking and drying commercially available anhydrous magnesium chloride in a dry hydrogen chloride gas stream at about 500 ° C for 15 hours) 20 g (0.21 mol), titanium tetrachloride 3.0 ml and silicon as a grinding aid 3.0 ml of oil (TSS-451, 20cs manufactured by Shin-Etsu Chemical Co., Ltd.) under a dry nitrogen stream, a container for a vibrating ball mill (stainless steel cylindrical type,
Magnetic ball with a volume of 1 l and a diameter of 10 mm is about 50% in apparent volume
Filled). This was attached to a vibrating ball mill with an amplitude of 6 mm and co-pulverized for 15 hours to obtain a co-pulverized solid. 15 g of the obtained co-ground product was suspended in 150 ml of 1,2-dichloroethane and stirred at 80 ° C for 2 hours, and then the solid part was collected by filtration. It was washed thoroughly until no dichloroethane was detected. This was dried under reduced pressure at 30 ° C to 40 ° C and hexane was removed to obtain a solid catalyst component. When the obtained solid catalyst component was analyzed, the content of titanium atoms in this solid catalyst component was 2.4 (wt%). (Production of polypropylene and measurement of stereoregularity) In a stainless steel autoclave with an internal volume of 3 l, 17 mg of solid catalyst component produced by the above method and 91 m of triethylaluminum
g, electron-donating compound tert-butyl-iso-pentyldimethoxysilane 52 mg, propylene 760 g and hydrogen 0.
1 g of hydrogen was charged. Increase the internal temperature by raising the temperature of the autoclave
When the stereoregularity of the polypropylene obtained by maintaining the temperature at 70 ° C for 1 hour and then terminating the polymerization by releasing the content gas was examined by boiling heptane extraction, the boiling heptane insoluble content of the polymer was 96.3 (wt%). )Met.

(Comparative Example 1) For comparison, tert-butylcyclohexyldimethoxysilane was used as an electron donating compound, and the stereoregularity of the polypropylene obtained in the same manner as in Example 1 was examined by boiling heptane extraction. The boiling heptane insoluble content of the polymer was 90.7 (wt.
%)Met.

[0012]

The novel organosilicon compound of the present invention is
Tert-butyl-iso-pentyldimethoxysilane is useful as an electron-donating compound in the production of α-olefin polymers, especially polypropylene, in magnesium chloride supported Ziegler-Natta catalyst systems. This organosilicon compound can also be used as a silane coupling agent or a resin modifier.

[Brief description of drawings]

FIG. 1 is a ¹ H-NMR spectrum diagram of tert-butyl-iso-pentyldimethoxysilane of the present invention.

FIG. 2 is a ¹³ C-NMR spectrum diagram of tert-butyl-iso-pentyldimethoxysilane of the present invention.

FIG. 3 is a ²⁹ Si-NMR spectrum diagram of tert-butyl-iso-pentyldimethoxysilane of the present invention.

Claims (1)

[Claims] 1. A chemical formula: Is tert-butyl-iso-pentyldimethoxysilane.