WO2024142601A1 - Organic silicon compound production method and production device - Google Patents

Abstract

The purpose of the present invention is to provide an organic silicon compound production method and an organic silicon compound production device, by which it is possible to efficiently produce an organic silicon compound at a high yield, by stably reacting, with certainty, an organic halide and a silicon compound.　This production method involves gradually adding an organic halide, a silicon compound, and magnesium to an organic solvent. The adding of the magnesium is performed at a constant rate for a predetermined period of time or is performed intermittently in multiple rounds. A production device 1 is provided with an addition means 3 that gradually adds magnesium.

Description

Manufacturing method and manufacturing apparatus for organosilicon compounds

The present invention relates to a method and apparatus for producing organosilicon compounds.

A known method for producing organic compounds by reacting organic halides with silicon compounds is a batch-type production method in which the organic halides and silicon compounds are added to a dispersion liquid in which magnesium is dispersed, and the organic silicon compounds are obtained by a Grignard reaction.

However, the reaction between organic halides and magnesium generates a large amount of heat, which raises the temperature of the reaction system and makes it difficult to control the reaction.

On the other hand, there is known a heat transfer device that improves the reaction rate by increasing the heat transfer efficiency between the contents and the reaction vessel (for example, Patent Document 1). Patent Document 1 discloses a heat transfer device that has a stirring tank that contains mother liquor, a liquid circulation means that circulates the liquid along the tank wall of the stirring tank, and at least one internal heat transfer means provided within the stirring tank.

However, the heat transfer device described in Patent Document 1 is intended to be used primarily as a concentration device or crystallization device, and is not necessarily sufficient for use as a reaction device for carrying out chemical reactions.

Therefore, there is a need to develop a method and apparatus for producing organosilicon compounds that can stably and reliably react organic halides with silicon compounds and efficiently produce organosilicon compounds with high yields.

Patent No. 4886157

The present invention aims to provide a method and apparatus for producing an organosilicon compound that can stably and reliably react an organic halide with a silicon compound and efficiently produce an organosilicon compound with a high yield.

The inventors discovered that by gradually adding an organic halide, a silicon compound, and magnesium to an organic solvent, the organic halide and the silicon compound can be reacted stably and reliably, and an organosilicon compound can be produced in high yield, leading to the completion of the present invention.

In other words, the first aspect of the present invention is a method for producing an organosilicon compound by gradually adding an organic halide, a silicon compound, and magnesium to an organic solvent.

The first aspect of the present invention can suitably adopt the following aspects.
1) The rate at which the magnesium is added is constant for a given period of time.
2) Adding the magnesium intermittently multiple times.
3) Purging the space containing the magnesium with an inert gas prior to addition.

The second aspect of the present invention is an organic compound manufacturing apparatus equipped with an addition means for gradually adding magnesium to an organic solvent.

According to the present invention, it is possible to stably and reliably react an organic halide with a silicon compound, and to efficiently produce an organosilicon compound with a high yield.

FIG. 1 is a diagram showing a manufacturing apparatus of the present invention. FIG. 2 is a graph showing particle size distribution of magnesium in an embodiment.

Below, an embodiment of the present invention will be described with reference to the drawings.

[Method for producing organosilicon compounds]
In the method for producing an organosilicon compound of the present invention, an organosilicon compound is produced by gradually adding an organic halide, a silicon compound, and magnesium particles 11 to an organic solvent.

When an organic halide, a silicon compound, and magnesium particles 11 are added to an organic solvent, the organic halide reacts with the magnesium to produce an organomagnesium halide, and the organomagnesium halide reacts with the silicon compound to produce an organosilicon compound.

In the method for producing an organosilicon compound of this embodiment, the temperature of the reaction system can be controlled by gradually adding the organic halide and silicon compound to the organic solvent and adjusting the rate at which the magnesium particles are added, thereby preventing a sudden increase in temperature in the reaction system. In addition, by adjusting the rate at which the magnesium particles 11 are added depending on the temperature of the solution 10 in the storage section 2 in which the organic halide and silicon compound are dissolved in the organic solvent, side reactions can be prevented, improving the conversion rate to organomagnesium halide. Furthermore, the organomagnesium halide can be reliably reacted with the silicon compound, making it possible to increase the yield of the organosilicon compound.

(Organic halides)
An organic halide is a compound containing a halogen element such as chlorine, bromine, or iodine and a hydrocarbon. Examples of the organic halide include known compounds such as chlorinated hydrocarbon compounds, brominated hydrocarbon compounds, and iodinated hydrocarbon compounds.

Specific examples of organic halides include monohalogenated alkyl compounds; monohalogenated alkenyl compounds; monohalogenated aromatic hydrocarbon compounds such as chlorobenzene, α-chlorotoluene, bromobenzene, α-bromotoluene, iodobenzene, and α-iodotoluene; dihalogenated alkyl compounds represented by the following formula (1); dihalogenated aromatic hydrocarbon compounds such as o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, o-dibromobenzene, m-dibromobenzene, p-dibromobenzene, o-diiodobenzene, m-diiodobenzene, and p-diiodobenzene; and the like.

式中、Ｒは、炭素数１～８の直鎖状又は分岐鎖状のアルキル基を示し、Ｘは、ハロゲン原子を示す。）

In the formula, R represents a linear or branched alkyl group having 1 to 8 carbon atoms, and X represents a halogen atom.

The alkyl group in the monohalogenated alkyl compound is preferably a straight-chain or branched-chain alkyl group having 1 to 8 carbon atoms. Specific examples of such monohalogenated alkyl compounds include chloromethane, chloroethane, chloropropane, 2-chloropropane, 1-chloro-2-methylpropane, 2-chloro-2-methylpropane, 2-bromo-2-methylpropane, chlorobutane, bromobutane, chloropentane, chlorocyclopentane, chlorohexane, bromomethane, bromoethane, bromopropane, 2-bromopropane, 1-bromo-2-methylpropane, bromobutane, bromopentane, bromocyclopentane, bromohexane, iodomethane, iodoethane, iodopropane, 2-iodopropane, 1-iodo-2-methylpropane, 2-iodo-2-methylpropane, iodopentane, iodocyclopentane, and iodohexane.

The alkenyl group in the monohalogenated alkenyl compound is preferably a linear or branched alkenyl group having 2 to 8 carbon atoms. Specific examples of such monohalogenated alkenyl compounds include chloroethylene, 3-chloro-1-propene, bromoethylene, 3-bromo-1-propene, iodoethylene, and 3-iodo-1-propene.

In the above formula (1), R represents a linear or branched alkyl group having 1 to 8 carbon atoms. Specific examples of such alkyl groups include methyl, ethyl, propyl, butyl, and isobutyl groups. Specific examples of dihalogenated alkyl compounds represented by the above formula (1) include 1,3-dichloropropane, 1,4-dichlorobutane, 1,5-dichloropentane, dibromomethane, 1,2-dibromoethane, 1,3-dibromopropane, 1,4-dibromobutane, 1,5-dibromopentane, 1,3-diiodopropane, 1,4-diiodobutane, and 1,5-diiodopentane.

Among these halogenated hydrocarbon compounds, monohalogenated alkyl compounds and dihalogenated alkyl compounds represented by the above formula (1) are preferred because they are useful as Grignard reagents, and monobromide alkyl compounds and dibromide alkyl compounds are more preferred.

(Silicon Compounds)
The silicon compound is not particularly limited as long as it is capable of reacting with the magnesium halide compound. Examples of the silicon compound include chlorosilane compounds such as dimethyldichlorosilane, methyltrichlorosilane, trimethylchlorosilane, methyldichlorosilane, vinyltrichlorosilane, phenyltrichlorosilane, and trichlorosilane; and alkoxysilane compounds such as methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, and octyltriethoxysilane, and two or more of these may be used in combination.

If at least one of the organic halide and the silicon compound is liquid, one can be used as a solvent and the other as a solute to prepare a homogeneous solution, which can then be gradually added to the organic solvent contained in the storage section 2; however, since it is easy to control the reaction temperature, it is also possible to dissolve the organic halide and the silicon compound in an organic solvent, and gradually add this solution to the organic solvent in the storage section 2. Alternatively, the organic halide and the silicon compound can each be dissolved in an organic solvent, and these solutions can each be gradually added to the organic solvent in the storage section 2.

(Organic solvent)
Specific examples of the organic solvent include ether solvents such as diethyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, 1,2-dimethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane. These ether solvents may be used alone or as a mixed solution of a plurality of solvents. Among these ether solvents, tetrahydrofuran is preferred in terms of industrial availability and high boiling point.

In addition, the magnesium halide compound formed as an intermediate during the reaction reacts with water and is inactivated. For this reason, it is preferable that the water content of the organic solvent used is low; specifically, it is preferable that it is less than 500 ppm, and more preferably less than 100 ppm.

The amount of organic solvent used may be appropriately determined taking into consideration the scale of the production equipment, heat removal efficiency, etc. When solution 10 is liquid at room temperature, from the viewpoint of productivity and from the viewpoint of suppressing the precipitation of salts such as magnesium halide produced as by-products in the reaction, it is preferable to use 1 to 99 parts by volume of organic solvent per 1 part by volume of organic halide, more preferably from 2 to 98 parts by volume, and even more preferably from 3 to 97 parts by volume. When solution 10 is solid at room temperature, from the viewpoint of productivity and from the viewpoint of suppressing the precipitation of salts such as magnesium halide produced as by-products in the reaction, it is preferable to use 1 to 130 parts by mass of organic solvent per 1 part by mass of organic halide, more preferably from 2 to 120 parts by mass, and even more preferably from 3 to 110 parts by mass.

(magnesium)
Magnesium is a substrate that reacts with an organic halide. The magnesium particles 11 to be added to the solution containing the organic halide and the silicon compound can be obtained, for example, by crushing a base body having a predetermined shape and size. The average particle size of the magnesium is preferably 0.5 mm or more and 5 mm or less, more preferably 0.7 mm or more and 2 mm or less.

(Method of measuring average particle size of magnesium)
The average particle size of the magnesium particles 11 can be obtained by using a histogram of particle size distribution obtained by classifying the particles using a test sieve and calculating the particle size at which the integrated value is 50% (FIG. 2).

Since metal impurities contained in magnesium can cause side reactions, it is preferable for the purity of magnesium to be 90% or more, and more preferably 99% or more.

(Organosilicon Compound Manufacturing Apparatus 1)
Fig. 1 is a perspective view showing a manufacturing apparatus 1 according to an embodiment of the present invention. As shown in Fig. 1, the manufacturing apparatus 1 includes a storage section 2 for storing a solution 10 containing an organic halide and a silicon compound, an adding means 3 for adding magnesium particles 11 to the storage section 2, an agitation and ejection means 4 for agitating the solution 10 and magnesium particles 11 in the storage section 2, and lifting up a part of the solution 10 and magnesium particles 11 and spraying them on the inner surface 21a of the storage section 2 that is higher than the liquid level, a power section 5 for applying rotational power to the agitation and ejection means 4, a recovery section 6 for cooling the evaporated matter or mist floating in the upper space in the storage section 2 and introducing only the liquid into the storage section 2 while discharging the gas to the outside, an extraction section 7 for extracting the organic silicon compound that is the product, a measurement section 8 for measuring the weight of the solution 10 in the storage section 2, and a jacket 9 for cooling the storage section 2.

(Storage section 2)
The container 2 contains a solution 10 in which an organic halide and a silicon compound have been added to an organic solvent, and magnesium particles 11 added from an adding means 3 are mixed into the solution 10 and stirred.

The storage section 2 is composed of a generally cylindrical straight body section 21 and a bottom section 22 that is continuous with the straight body section 21 below, and a jacket 9 is disposed on the outer periphery of the storage section 2 so as to cover the outer periphery of the straight body section 21.

The reaction that occurs when magnesium particles 11 are added to solution 10 to which an organic halide and a silicon compound have been added is an exothermic reaction, so it is cooled by jacket 9 through the side wall surface of straight body portion 21. Therefore, inner surface 21a of straight body portion 21 functions as a heat removal surface that removes heat generated by the exothermic reaction.

The dimensions of the storage section 2 are not particularly limited and can be set appropriately depending on conditions such as production volume, but for example, the diameter of the straight body section 21 is preferably 100 mm or more and 1800 mm or less, and more preferably 300 mm or more and 500 mm or less. In addition, the height of the straight body section 21 is preferably 100 mm or more and 1000 mm or less, and more preferably 300 mm or more and 1000 mm or less.

Furthermore, the height _H1 of the liquid surface of the solution 10 in the straight body portion 21 is not particularly limited, but is preferably 0.050 to 0.50 times the total height of the straight body portion 21. As an example, when the height of the straight body portion 21 is 500 mm, the height of the liquid surface is preferably 40 to 250 mm.

Furthermore, the height _H2 of the body portion 21 from the liquid surface is not particularly limited, but is set to be higher than the height of the layered film 10f formed on the inner surface 21a, and in order to enhance the stirring of the mixture of the solution 10 and the magnesium particles 11 and the cooling effect by the jacket 9, the height _H2 is preferably 0.40 to 0.95 times the total height of the body portion 21. As an example, when the total height of the body portion 21 is 500 mm, the height _H2 is preferably 200 to 475 mm.

Figure 1 shows an example of a straight body portion 21 in which the inner surface 21a extends in the vertical direction, but this is not limited to this, and the inner surface 21a may be inclined inward or outward of the storage portion 2 as it moves from the bottom to the top.

A bottom portion 22 with a concave inner surface formed in an inverted cone shape is attached to the lower end of the straight body portion 21, and an extraction portion 7 is provided at the lower tip of the bottom portion 22.

(Removal section 7)
The removal section 7 is equipped with a guide path 71 that communicates with the inside of the bottom section 22, and a valve 72 at the upper end of the guide path 71 for opening and closing the guide path 71, and after the reaction is completed, the guide path 71 is opened by the valve 72, so that the organosilicon compound product can be removed from the storage section 2. Note that, although an example in which the inner surface of the bottom section 22 has an inverted cone shape is shown in Fig. 1, the present invention is not limited to this, and an inverted dome shape may also be used.

(Jacket 9)
The jacket 9 is disposed so as to cover the outer peripheral surface of the straight body portion 21. The jacket 9 includes an inlet 91 formed on the lower side surface and an outlet 92 formed on the upper side surface opposite to the inlet 91, and is configured so that a heat transfer medium or a refrigerant flows through the jacket 9 from the inlet 91 to the outlet 92. The heat transfer medium or the refrigerant flows through the jacket 9, thereby enabling efficient heat exchange with the solution 10 in the storage portion 2 that contacts the inner side surface 21a of the straight body portion 21. It is preferable that the jacket 9 is disposed so as not to cover the bottom portion 22 so that the evaporation rate is naturally adjusted to an appropriate value when the volume of the solution becomes small.

(Addition Means 3)
The adding means 3 adds magnesium particles 11 into the storage unit 2. The adding means 3 includes a hopper 31 that temporarily stores the magnesium particles 11 before addition, a delivery unit 32 that controls the opening and closing of the outlet of the hopper 31 to deliver the magnesium particles 11, and an introduction pipe 33 that introduces the magnesium particles 11 into the storage unit 2.

The hopper 31 is preferably in the shape of an inverted cone or an inverted polygonal pyramid. The inlet pipe 33 is preferably installed so that its tip connected to the storage section 2 is horizontal or has a downward slope in order to avoid blockage by magnesium particles 11. The center section of the inlet pipe 33 can have a certain angle with respect to the liquid surface, but the base section connected to the delivery section 32 is preferably installed with the direction of travel inclined downward so that the angle with respect to the horizontal is equal to or less than the angle of repose of the magnesium particles 11 in order to prevent the magnesium particles 11 from flowing into the storage section 2 all at once when the bottom of the hopper 31 is opened and to make it easier to control the amount of magnesium particles 11 added.

The magnesium particles 11 are added continuously for a certain period of time at a constant rate, or the amount added in one go is less than the equivalent amount of the silicon compound substrate, and is added multiple times, for example, 2 to 5 times. By gradually adding magnesium in this way, the reaction caused by magnesium becomes rate-limiting and the production of unnecessary by-products can be suppressed.

In order to prevent the generation of by-products due to hydrolysis, it is preferable to dry the magnesium with an inert gas in advance to remove moisture. For this reason, it is preferable to purge the space containing the magnesium with an inert gas to remove moisture adhering to the magnesium before adding it to the storage unit 2. For example, any method can be used, such as purging the storage chamber in which the magnesium is stored before being added to the storage unit 2 or the inside of the hopper 31 of the manufacturing device 1 with an inert gas such as nitrogen or argon while heating it, or purging with dry nitrogen gas.

(Agitation and ejection means 4)
The stirring and ejecting means 4 comprises a rotating shaft 41 which extends vertically and serves as the center of rotation, an attachment portion 43 which extends horizontally and whose center is connected to the lower end of the rotating shaft 41, and a guide portion 42 which is attached to the lateral outer edge of the attachment portion 43 and is inclined so that its upper tip approaches the inner surface 21a of the straight body portion 21.

The stirring and ejecting means 4 is positioned so that the attachment part 43 is placed in the solution 10, and when the rotating shaft 41 rotates, the solution 10 and magnesium particles 11 contained in the storage part 2 are stirred by the attachment part 43 and the induction part 42, and the mixture of the solution 10 and magnesium particles 11 is sprayed onto the inner surface 21a of the straight body part 21 by the induction part 42.

The induction section 42 has, for example, an approximately cylindrical or semi-cylindrical shape. In addition, the induction section 42 is inclined so as to gradually approach the inner surface 21a from the bottom to the top. Therefore, when the rotating shaft 41 rotates, the mixture of the solution 10 and the magnesium particles 11 is scooped up while stirring the solution 10 and the magnesium particles 11 below the induction section 42, and the mixture is pulled upward along the inner wall surface of the induction section 42 using centrifugal force, and the mixture is dispersed from the upper tip toward the inner surface 21a of the straight body section 21.

In this embodiment, two induction sections 42 are provided. The number of induction sections 42 is not limited to two, and may be one, or three or more. The number of induction sections 42 can be adjusted, for example, according to the size of the storage section 2. When multiple induction sections 42 are provided, it is preferable to arrange them so that they are rotationally symmetrical about the rotation axis 41 in order to maintain the measurement accuracy of the measurement section 8 described below. Specifically, it is preferable that they are arranged at equal intervals along the rotating circumferential direction when viewed in a plan view from above (i.e., when viewed from above in FIG. 1).

(Power unit 5)
The power unit 5 provides rotational power to the rotating shaft 41. The power unit 5 includes a motor 51, a rotation transmission shaft 52 that transmits the power from the motor 51 to the rotating shaft 41, and a joint 53 that connects the rotating shaft 41 and the rotation transmission shaft 52.

The rotation transmission shaft 52 may be a continuous straight one, but for example, when the solution to be reacted is a flammable liquid, it is preferable to take into consideration the leakage of flammable gas from the viewpoint of explosion prevention, and to place the motor 51 at a position far removed from the leakage range of the flammable gas, or to provide a partition wall or the like (not shown) to prevent the flammable gas from contacting the motor 51. In the former case, in order to easily realize the installation of the motor 51, it is preferable that the rotation transmission shaft 52 is made of a flexible material. By forming the rotation transmission shaft 52 from a flexible material, the degree of freedom of the range in which the power unit 5 is installed is increased, and the manufacturing apparatus 1 can be made compact.
Furthermore, for the joint 53, for example, a magnetic shaft seal (joint gas seal), a mechanical seal, a gas seal, an oil seal, or the like can be used to seal the rotating shaft 41 and the rotation transmitting shaft 52. In order to more reliably prevent the intrusion of impurities, it is preferable that the joint 53 be a magnetic shaft seal.

(Collection section 6)
The recovery section 6 has a function of recovering at least a portion of the low boiling point components evaporated from the solution 10 or the mist-like released matter generated by stirring the solution 10, and returning them to the storage section 2. By providing such a recovery section 6, the yield of the reaction can be improved.

The recovery section 6 includes an exhaust pipe 61 that exhausts low boiling point components and mist-like releases from the storage section 2 to the outside together with an inert gas such as nitrogen, a separation section 62 that separates the low boiling point components and mist-like releases sent via the exhaust pipe 61 from the gas, a cooling coil 63 that is provided to surround the outer periphery of the separation section 62 and cools the separation section 62, a discharge pipe 64 that exhausts the gas to the outside of the separation section 62, and a reflux pipe 66 that returns the recovered liquid to the storage section 2. A first reflux valve 651 and a second reflux valve 652 are disposed in the middle of the reflux pipe 66, and normally the first reflux valve 651 is open and the second reflux valve 652 is closed, but when the recovered liquid accumulates above the second reflux valve 652, the first reflux valve 651 is closed and the second reflux valve 652 is opened to return the recovered liquid to the storage section 2. In addition, by adjusting the temperature of the refrigerant circulating inside the cooling coil 63, it is possible to discharge components not required for the reaction to the outside without collecting them.

The separation section 62 is configured to include, for example, a cyclone structure. This cyclone structure is configured so that the discharged material taken in can be separated into liquid droplet components and gas components by swirling. Note that the separation section 62 is not necessarily limited to having a cyclone structure, and may be, for example, a Dimroth cooler that passes a refrigerant through it to trap low boiling point components. However, in order to trap the mist more efficiently, it is preferable that the separation section 62 has a cyclone structure.

(Measurement unit 8)
The measuring section 8 is provided on the edge of the bottom side of the straight body section 21. For example, a load cell 80 can be used as the measuring section 8. In this embodiment, three load cells 80 are provided as the measuring section 8 (two load cells 80 are illustrated in FIG. 1 for convenience of explanation). The number of load cells 80 is not limited to three and may be four or more, but in order to prevent wobbling of the entire manufacturing apparatus 1 and to eliminate the difference in load between the load cells, it is preferable to support the manufacturing apparatus 1 at three points and to use three load cells. The load cell 80 not only measures the amount of remaining liquid in the storage section 2, but also measures the amount of weight change per hour.

(Example)
Tetrahydrofuran was placed in the container 2 of the production apparatus 1, and a tetrahydrofuran solution of 1,3-dibromopropane and methyltrichlorosilane was gradually added thereto at a rate of 78 g/min.

In addition, together with the addition of the tetrahydrofuran solution of 1,3-dibromopropane and methyltrichlorosilane, magnesium particles (average particle size: 0.9 mm) were added to the container 2 from the addition means 3 of the manufacturing device 1. The magnesium particles 11 were added at a constant rate so that 20 g of magnesium was added in 2 hours.

A portion of the resulting reaction solution was removed, triethylamine was added dropwise, and ethanol was then added to remove the by-product salts, and the filtrate was collected. The filtrate was then replaced with cyclopentyl methyl ether, and the by-product salts dissolved in the tetrahydrofuran were precipitated and removed. The yield was calculated from the concentration of the resulting polymer components relative to the total reaction solution, and was found to be 100%.

Comparative Example
A solution was prepared by dissolving 1,3-dibromopropane and trichloromethylsilane in tetrahydrofuran. In addition, magnesium particles (average particle size: 0.9 mm) were dispersed in tetrahydrofuran to prepare a dispersion of magnesium particles. The magnesium concentration in the dispersion was 3.0% by weight.

15 L of the magnesium particle dispersion was placed in the storage section 2 of the manufacturing device 1, and the solution was added to the storage section 2 while stirring. The drip rate of the solution was 78 g/min. A portion of the resulting reaction solution was taken out, and the yield was calculated in the same manner as in the previous example, which was 89%.

REFERENCE SIGNS LIST 1 Manufacturing apparatus 2 Storage section 3 Addition means 4 Stirring and ejection means 5 Power section 6 Recovery section 7 Take-out section 8 Measurement section 9 Jacket 10 Solution 11 Magnesium particles 21 Straight body section 21a Inner surface 22 Bottom section 31 Hopper 32 Delivery section 33 Introduction pipe 41 Rotation shaft 42 Guidance section 43 Mounting section 51 Motor 52 Rotation transmission shaft 53 Joint 61 Discharge pipe 62 Separation section 63 Cooling coil 64 Discharge pipe 66 Circulation pipe 71 Guide path 72 Valve 80 Load cell 91 Inlet 92 Outlet 651 First circulation valve 652 Second circulation valve

Claims (5)

A method for producing an organosilicon compound by gradually adding an organic halide, a silicon compound, and magnesium to an organic solvent. The method for producing an organosilicon compound according to claim 1, wherein the magnesium addition rate is constant for a predetermined period of time. The method for producing an organosilicon compound according to claim 1, in which the magnesium is added intermittently multiple times. The method for producing an organosilicon compound according to any one of claims 1 to 3, wherein the space containing the magnesium is purged with an inert gas before the addition. An apparatus for manufacturing organosilicon compounds, equipped with an addition means for gradually adding magnesium to an organic solvent.

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