Method for producing organosilicon compound

Abstract

To provide a method for producing an organosilicon compound that enables efficient filtration and removal of by-product salts by a simple and safe process with excellent workability.SOLUTION: A method for producing an organosilicon compound, comprises a reaction step of reacting a halosilane compound with a first alcohol to obtain a liquid or slurry containing an alkoxysilane, a filtration step of filtering a salt generated in the reaction step, and a dissolution step of bringing the salt into contact with a dissolving agent containing a second alcohol having 1 to 3 carbon atoms after the filtration step to dissolve the salt.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a method for producing an organosilicon compound. [Background technology]

[0002] Organosilicon compounds are used in a wide range of fields, and have attracted attention as important compounds in fields such as materials engineering, optics, medicine, and agriculture. In the production of organosilicon compounds, it is important to control the structure depending on the application. One method for obtaining organosilicon compounds with a desired structure is a synthesis method using the Grignard reaction. The Grignard reaction is a reaction using a Grignard reagent produced by the reaction of magnesium with an organic halide, and by utilizing this reaction, a desired organic group or the like can be added to the silicon element in the organosilicon compound. For example, Patent Document 1 discloses a method for producing a dialkyldialkoxysilane by reacting dichlorosilane with a Grignard reagent having a specific structure. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 09-012584 Summary of the Invention [Problem to be solved by the invention]

[0004] However, when producing an organosilicon compound, if the reaction process includes a specific reaction, particularly an alkoxylation reaction, a large amount of by-product salts may be produced, causing the reaction liquid to become a highly viscous liquid or slurry. Therefore, in order to obtain the desired organosilicon compound, it is necessary to remove the by-product salt by means of filtration or the like. The filtration of the by-product salt is usually carried out using a filtration device equipped with a container (tank) for containing the reaction liquid and a filtration member such as filter paper. After recovering the liquid components of the reaction liquid, the by-product salt remaining on the filtration member is removed. However, this requires steps such as stopping the agitation of the filtration device, opening the outlet at the top of the tank, and removing the by-product salt through it. However, such steps pose problems from the standpoints of workability and safety, and there is room for improvement. Therefore, an object of the present invention is to provide a method for producing an organosilicon compound that is easy to use and allows for the filtration and removal of by-product salts in a simple and safe manner. [Means for solving the problem]

[0005] As a result of extensive research, the present inventors have found that the above-mentioned problems can be solved by performing filtration using a filtration device equipped with a predetermined stirring means.

[0006] That is, the gist of the present invention is specifically as follows. <1> A method for producing an organosilicon compound, comprising: a reaction step of reacting a silicon halide compound with a first alcohol to obtain a liquid or slurry containing an alkoxysilane; a filtration step of filtering the salt generated in the reaction step; and a dissolving step of contacting the salt with a dissolving agent containing a second alcohol having 1 to 3 carbon atoms after the filtering step to dissolve the salt. A method for producing an organosilicon compound, comprising: <2> the second alcohol is methanol; <1> 2. A method for producing the organosilicon compound according to claim 1. <3> <1> The alkoxysilane is an alkoxysilane represented by the following formula (6), or <2> 2. A method for producing the organosilicon compound according to claim 1. [ka] In formula (6), R 1 each independently represents a hydrogen atom or a monovalent organic group, R2 each independently represents an organic group, and R 3 each independently represents an alkyl group, and n represents the number of repetitions and is an integer of 2 or more. <4> In the dissolving step, the amount of the second alcohol supplied is 0.5 times or more by mass relative to the amount of the salt. <1> ~ <3> 10. The method for producing an organosilicon compound according to claim 9, wherein the organic silicon compound is a silicon dioxide. [Effects of the Invention]

[0007] According to one embodiment of the present invention, there is provided a method for producing an organosilicon compound that is easy to use and allows for simple and safe filtration and removal of by-product salts. [Brief explanation of the drawings]

[0008] [Figure 1] FIG. 1 is a cross-sectional view showing an example of a filtering device. [Figure 2] FIG. 2 is a schematic diagram showing an example of a shaft and an agitating blade. [Figure 3] FIG. 3 is a schematic cross-sectional view illustrating an example of the shape of the stirring blade. [Figure 4] FIG. 4 is a schematic diagram of an example of a filtering member viewed from a vertical direction. DETAILED DESCRIPTION OF THE INVENTION

[0009] Although the embodiments of the present invention will be described in detail below, the present invention is not limited to these details as long as they do not deviate from the gist of the present invention. Furthermore, the present invention can be implemented by making any modifications within the scope of the present invention. Furthermore, when a numerical range is described in stages, the upper and lower limits of each numerical range can be combined arbitrarily. Furthermore, the expression "A or B" in this specification may be read as "at least one selected from the group consisting of A and B." Furthermore, the expression "amount of B relative to amount of A" in this specification means "amount of B / amount of A." Furthermore, although a number of embodiments are described in this specification, various conditions in each embodiment may be applied to each other to the extent that they are applicable.

[0010] In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​written before and after "to" as the lower and upper limits, and "A to B" means A or more and B or less.

[0011] One embodiment of the present invention is a method for producing an organosilicon compound, comprising: a reaction step of reacting a halogenated silicon compound with a first alcohol to obtain a liquid or slurry containing an alkoxysilane; a filtration step of filtering a salt produced in the reaction step; and, following the filtration step, a dissolution step of contacting the salt with a dissolving agent containing a second alcohol having 1 to 3 carbon atoms to dissolve the salt.

[0012] Hereinafter, a manufacturing method according to the present embodiment and a filtration device that can be used in the manufacturing method will be described with reference to the drawings, but the present invention is not limited to these embodiments. Furthermore, the dimensions, materials, shapes, and relative positions of the components described in the descriptions and drawings of each embodiment are merely examples.

[0013] <Method for producing organosilicon compounds> The method for producing an organosilicon compound according to one embodiment of the present invention is not particularly limited as long as it includes a reaction step of reacting a halogenated silicon compound with a first alcohol to obtain a liquid or slurry containing an alkoxysilane (hereinafter also referred to simply as a "reaction liquid"), a filtration step of filtering the salt produced in the reaction step, and a dissolution step of contacting the salt with a dissolving agent containing a second alcohol having 1 to 3 carbon atoms after the filtration step to dissolve the salt, and any known method can be appropriately adopted depending on the desired organosilicon compound. Furthermore, the compound may be produced through multiple reactions other than the above reaction steps.

[0014] [Reaction process] <Halogenated silicon compounds> The silicon halide compound is not particularly limited as long as it can produce the desired alkoxysilane upon reaction with the first alcohol, and any known silicon halide compound can be used.

[0015] The silicon halide compound can be represented by the following formula (1). SiR 1 a X 4-a (1) In the above formula (1), R 1 each independently represents a hydrogen atom or a monovalent organic group; each X independently represents a halogen atom; and a represents an integer of 0 to 3.

[0016] R 1 are not particularly limited as long as they are each independently a hydrogen atom or a monovalent organic group, and may be a hydrogen atom or a monovalent hydrocarbon group, but are preferably a hydrogen atom from the viewpoint of reactivity. The monovalent organic group may have a straight-chain structure, a branched-chain structure, a ring structure (alicyclic structure and / or aromatic ring structure), or an unsaturated bond. R 1 The monovalent hydrocarbon group is not particularly limited, but from the viewpoint of reactivity, the hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and even more preferably 1 or 2 carbon atoms.

[0017] There are no particular limitations on X, so long as each X is independently a halogen atom, and X may be any of a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0018] There are no particular limitations on a, provided that it is an integer of 0 to 3.

[0019] Specific examples include monohalosilanes such as chlorosilane, bromosilane, iodosilane, methylchlorosilane, methylbromosilane, methylchlorosilane, methylbromosilane, ethylchlorosilane, ethylbromosilane, dimethylchlorosilane, dimethylbromosilane, trimethylchlorosilane, and triethylchlorosilane; dihalosilanes such as dichlorosilane, dibromosilane, diiodosilane, methyldichlorosilane, methyldibromosilane, ethyldichlorosilane, ethyldibromosilane, dimethyldichlorosilane, and dimethyldibromosilane; trihalosilanes such as trichlorosilane, tribromosilane, triiodosilane, methyltrichlorosilane, methyltribromosilane, ethyltrichlorosilane, and ethyltribromosilane; and tetrahalosilanes such as tetrachlorosilane, tetrabromosilane, and tetraiodosilane.

[0020] Silicon halide compounds may also be synthesized by Grignard reactions depending on the desired end product. For example, the above-mentioned silicon halide compounds (SiR 1 X3), organic halides (R 2 Y2;R 2 is any organic group, Y is a halogen atom) and magnesium (Mg) First, Grignard reagents (R 2 (Y)MgY), and then the Grignard reagent is reacted with a silicon halide compound, and at least some of the X in the silicon halide compound is converted to R 2 to obtain a halogenated silicon compound (hereinafter also referred to as compound (2)) having a structure represented by the following formula (2). [ka] Furthermore, the reaction of compound (2) with magnesium affords a Grignard reagent (YMgR 2 Si(R 1)(X)2) is produced, and then the reaction between the Grignard reagent and a halogenated silicon compound or compound (2) is repeated multiple times to produce an organosilicon compound having a structure represented by the following formula (3) (hereinafter also referred to as compound (3)): [ka] In formula (3), n represents the number of repetitions and is an integer of 2 or more.

[0021] <First Alcohol> There are no particular limitations on the first alcohol, so long as it can react with the halogenated silicon compound to give the desired alkoxysilane. The first alcohol can be represented by the following formula (4). R 3 OH (4) In the above formula (4), R 3 represents an alkyl group.

[0022] R 3 is not particularly limited as long as it is an alkyl group, and the alkyl group may have a linear structure or a branched structure. R 3 The alkyl group in the above is not particularly limited, but from the viewpoint of reactivity, the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 or 2.

[0023] Specific examples include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, and 2-methyl-2-propanol.

[0024] <Liquid or slurry containing alkoxysilane> The alkoxysilane is produced by reacting the halogenated silicon compound with the first alcohol. During this reaction, a by-product salt is produced during the series of reaction steps, causing the reaction liquid to become a highly viscous liquid or slurry. The composition of the by-product salt is uncertain because it depends on the silicon halide compound, alcohol, and other compounds contained in the raw materials, but it is assumed that hydrogen halide is generated by the reaction of silicon halide compound with alcohol, and that hydrogen halide is then generated by reacting with compounds in the reaction solution. The reaction solution in the series of reaction steps is often pre-mixed with basic compounds for the purpose of neutralization, etc. Therefore, the by-product salt may include a salt of the above basic compound with a hydrogen halide. The basic compound is preferably an alkylamine, more preferably triethylamine.

[0025] Alkoxysilane can be represented by the following formula (5). Si(R 1 ) a (OR 3 ) 4-a (5) In the above formula (5), R 1 and a are derived from the halogenated silicon compound used as the raw material and are the same as in the above formula (1); R 3 is derived from the first alcohol and is the same as in formula (4) above, where R 1 or R 3 When there are a plurality of, they are independent and may be different from each other.

[0026] Specific examples of monoalkoxysilanes include methoxy-based silanes such as methoxysilane, methylmethoxysilane, ethylmethoxysilane, propylmethoxysilane, butylmethoxysilane, vinylmethoxysilane, phenylmethoxysilane, dimethylmethoxysilane, methylethylmethoxysilane, and diethylmethoxysilane; ethoxy-based silanes such as ethoxysilane, methylethoxysilane, ethylethoxysilane, propylethoxysilane, butylethoxysilane, vinylethoxysilane, phenylethoxysilane, dimethylethoxysilane, methylethylethoxysilane, and diethylethoxysilane; and propoxy-based silanes such as propoxysilane, methylpropoxysilane, ethylpropoxysilane, propylpropoxysilane, butylpropoxysilane, vinylpropoxysilane, phenylpropoxysilane, dimethylpropoxysilane, methylethylpropoxysilane, and diethylpropoxysilane.

[0027] Specific examples of dialkoxysilanes include dimethoxysilanes such as dimethoxysilane, methyldimethoxysilane, ethyldimethoxysilane, propyldimethoxysilane, butyldimethoxysilane, vinyldimethoxysilane, phenyldimethoxysilane, dimethyldimethoxysilane, methylethyldimethoxysilane, and diethyldimethoxysilane; diethoxysilane, methyldiethoxysilane, ethyldiethoxysilane, propyldiethoxysilane, butyldiethoxysilane, and vinyldiethoxysilane; diethoxy-based silanes such as phenyldiethoxysilane, dimethyldiethoxysilane, methylethyldiethoxysilane, and diethyldiethoxysilane; or dipropoxy-based silanes such as dipropoxysilane, methyldipropoxysilane, ethyldipropoxysilane, propyldipropoxysilane, butyldipropoxysilane, vinyldipropoxysilane, phenyldipropoxysilane, dimethyldipropoxysilane, methylethyldipropoxysilane, and diethyldipropoxysilane.

[0028] Specific examples of trialkoxysilanes include trimethoxy-based silanes such as trimethoxysilane, methyltrimethoxysilane, ethyltrimethoxysilane, vinyltrimethoxysilane, and phenyltrimethoxysilane; triethoxy-based silanes such as triethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, vinyltriethoxysilane, and phenyltriethoxysilane; and tripropoxy-based silanes such as tripropoxysilane, methyltrippropoxysilane, ethyltrippropoxysilane, vinyltrippropoxysilane, and phenyltrippropoxysilane.

[0029] Specific examples of tetraalkoxysilane include tetramethoxysilane, tetraethoxysilane, and tetrapropoxysilane.

[0030] Alternatively, the compound (3) may be reacted with a first alcohol to produce an alkoxysilane represented by the following formula (6). [ka] In formula (6), n represents the number of repetitions and is an integer of 2 or more.

[0031] The amounts and concentrations of the silicon halide compound and the first alcohol used in the reaction step are not particularly limited and may be adjusted appropriately depending on the structure of each raw material, the structure of the target alkoxysilane, etc. As an example, a liquid or slurry containing alkoxysilane can be obtained by reacting 0.01 to 5.0 mol / L of the silicon halide compound with 0.1 to 25 mol / L of the first alcohol.

[0032] The method for carrying out the alkoxylation reaction is not particularly limited and can be carried out by a known method. The reaction conditions are also not particularly limited, and the reaction temperature may be, for example, 10 to 80°C or 20 to 50°C, the reaction time may be, for example, 1 to 24 hours or 1 to 4 hours, and the reaction atmosphere may be, for example, air or an inert gas.

[0033] (Other ingredients) In the reaction step, components (other components) other than the above-mentioned halogenated silicon compound and first alcohol may be used within the scope that does not impair the effects of the present invention, such as a solvent or an additive, etc. Also, a neutralization step of adding an alkylamine (e.g., triethylamine) to neutralize the reaction solution may be included.

[0034] <Filtration process / filtration equipment> The method for producing an organosilicon compound according to one embodiment of the present invention includes a filtration step in which the salt generated in the reaction step is filtered. The specific embodiment of the filtration step and the configuration of the filtration device are not particularly limited as long as the salt can be filtered, and known methods and devices can be used. As an example, the by-product salt can be filtered while stirring using a filtering device described below. FIG. 1 is a cross-sectional view showing an example of a filtration device according to one embodiment of the present invention. 1 has a container 101 for containing a liquid or a slurry, and two stirring blades 103 attached to a shaft 102. A filtering member 105 is fixed to the bottom of the container 101 by a fixing member 104. The filtering device 100 preferably has an outlet (not shown) for recovering the reaction liquid (filtrate) filtered by the filtering member 105 and the liquid in which the by-product salt has been dissolved in the dissolving step described below.

[0035] [Containment Container] The shape of the storage vessel 101 is not particularly limited, and may be cylindrical or pot-shaped. The size (capacity) of the storage vessel 101 is also not particularly limited, and may be selected appropriately depending on the production scale. For example, it is 1 to 10 L on a lab scale and 10 to 500 L on an industrial scale. Furthermore, the container 101 may have a structure that allows it to be pressurized.

[0036] The filtration step may be performed by introducing a reaction solution containing a by-product salt produced in a separate reaction vessel into the storage vessel 101, but the filtration device 100 may also serve as a reaction device. That is, after the Grignard reaction or alkoxylation reaction is carried out in the storage vessel 101, the reaction solution in the storage vessel 101 may be filtered as is. Therefore, the filtration device 100 The reactor may be equipped with other devices and functions necessary for the reaction, such as a thermometer, a cooling means, a gas introduction tube, and the like. The filtration step may be repeated multiple times as necessary, which can improve the yield and purity of the desired organosilicon compound and reduce the amount of dissolving agent used in the dissolving step.

[0037] [shaft] The shaft 102 is not particularly limited as long as it can be fitted with the stirring blade 103 and driven. The shape and size of shaft 102 are not particularly limited, but an example is a rod shape with a thickness of 20 to 100 mm and a length of 200 to 2000 mm, and the cross section may be circular, elliptical, polygonal, or the like. From a cost perspective, the shaft 102 is preferably gas driven, and more preferably compressed air driven.

[0038] [Mixing blade] The stirring blade 103 is attached to the shaft 102 and moves up and down as the shaft 102 is driven, thereby stirring the reaction liquid in the container 101 . 2 shows a schematic diagram of the shaft 102 and the stirring blade 103. The shape of the stirring blade 103 is not particularly limited and may be a plate shape, a disk shape, a cone shape, or the like, but from the viewpoint of stirring efficiency, a substantially disk shape or a substantially cone shape is preferable. When the stirring blade is in the shape of a plate or a disk, its thickness is preferably 3 to 30 mm. Furthermore, when the stirring blade 103 has a substantially conical shape as shown in Fig. 3, the angle θ formed by the bottom surface of the stirring blade 103 and the generating line B is preferably 1 to 30°. When the angle θ is within the above range, the liquid resistance during stirring is reduced, allowing for efficient stirring. Furthermore, it is possible to prevent the reaction liquid from remaining on the stirring blade 103 after the filtration step. The angle θ is more preferably 3 to 20°, and particularly preferably 5 to 10°. Furthermore, in order to prevent the reaction liquid from remaining on the stirring blade 103, the stirring blade 103 may have through-holes that penetrate through it in the thickness direction.

[0039] The number of stirring blades 103 may be one or more. From the viewpoint of the balance between stirring efficiency and the cost of the device itself, the number is preferably one to two. When there are multiple stirring blades 103, the blades may be different in shape, size, material, etc. The position where the stirring blade 103 is attached to the shaft 102 is not particularly limited, but it is preferable that the blade located at the bottom of the container 101 be attached so that it can move up and down within a range of 5 to 75% of the height from the bottom of the container 101.

[0040] The size of the stirring blade 103 is not particularly limited, but the area of ​​the lower surface of the blade located lowest in the storage vessel 101 is preferably 30 to 90%, more preferably 40 to 80%, and particularly preferably 50 to 70% of the bottom area of ​​the storage vessel 101. When the size of the stirring blade 103 is within the above range, efficient stirring and filtration can be performed even if the reaction liquid is a highly viscous liquid or slurry. In the above calculation, if the stirring blade 103 has a through-hole, it is treated as if it does not have a through-hole, and if the bottom surface of the storage container 101 is curved, the cross-sectional area at the position where the uppermost fixing member 104 is located is treated as the bottom area of ​​the storage container 101. When the stirring blade 103 has through-holes, the opening ratio of the stirring blade 103 (the ratio of the area of ​​the through-holes to the area of ​​the bottom surface of the stirring blade 103) is preferably 5 to 40%, more preferably 10 to 25%. When the opening ratio is within the above range, the reaction liquid can be sufficiently prevented from remaining on the stirring blade 103.

[0041] In the filtration process, the stirring blade 103 moves up and down at a speed of 50 to 1000 mm / s. By keeping the speed of the up-and-down movement of the stirring blade 103 within the above range, the reaction liquid can be efficiently stirred and filtered without placing an excessive load on the apparatus. A speed of 70 to 500 mm / s is more preferable, and a speed of 100 to 300 mm / s is particularly preferable.

[0042] The stroke width of the up and down movement of the stirring blade 103 is not particularly limited and depends on the size and shape of the storage container 101, but if the storage container 101 is cylindrical with an inner diameter of 500 mm and a height of 600 mm, it is preferably 150 to 420 mm, and more preferably 200 to 300 mm.

[0043] The stroke period of the up-and-down movement of the stirring blade 103 is preferably 0.2 to 4.0 / s. By keeping the stroke period of the up-and-down movement of the stirring blade 103 within the above range, the reaction liquid can be efficiently stirred and filtered without placing an excessive load on the apparatus. A stroke period of 0.4 to 3.0 / s is more preferable, and a stroke period of 0.6 to 2.0 / s is particularly preferable.

[0044] [Filtering material] The filtering member 105 is provided at the bottom of the container 101 and filters out salts produced in the reaction step. The filtering member 105 is not particularly limited as long as it has a filtering function, and examples thereof include filter paper and filter cloth. Among these, filter paper is preferred from the viewpoints of filtering efficiency and cost. Furthermore, filter paper having a particle retention capacity of 1 μm to 20 μm is more preferred, and filter paper having a particle retention capacity of 2 μm to 10 μm is particularly preferred.

[0045] The filtering member 105 may be a single member or multiple members, for example, multiple sheets of filter paper may be stacked, or different members may be combined.

[0046] [Fixed part] In this embodiment, the liquid in the storage container 101 is agitated by the up and down movement of the agitating blade 103, and therefore, compared to agitation using a rotary agitating blade, a force is more likely to act on the filtering member 105 in the up and down direction (vertical direction). Therefore, the filtering member 105 is fixed to the bottom of the storage container 101 by a fixing member 104. The shape and size of the fixing member 104 are not particularly limited and may be adjusted appropriately depending on the shape and size of the bottom of the storage container 101. The fixing member 104 is, for example, a plate-like member or a ring-like member having a shape similar to the cross section of the bottom of the storage container 101. It is preferable that the fixing member 104 has a substantially circular plate shape.

[0047] From the viewpoint of firmly fixing the filtration member 105, the fixing member 104 is preferably made of two or more plate-like members that sandwich the filtration member 105 from above and below to fix the filtration member 105. Furthermore, from the viewpoint of not impairing the filtration efficiency, it is preferable that the fixing member 104 has a through-hole formed therethrough in the thickness direction. Fig. 4 is a schematic diagram of an example of a filtering member 105 viewed from the vertical direction. In the example shown in Fig. 4, the filtering member 105 has a disk shape and has a plurality of hexagonal through holes 106 formed therein. However, the number, shape, and size of the through holes 106 are not limited, and for example, the through holes 106 may be circular or any polygonal shape. Furthermore, when there are a plurality of fixing members 104, the respective members may all be the same or may be different from one another.

[0048] When the fixing member 104 has through-holes 106, the aperture ratio thereof is preferably 20 to 80%, more preferably 30 to 70%, and particularly preferably 40 to 60%. When the aperture ratio is within the above range, a good balance is achieved between fixing the filtering member 105 and filtering efficiency. The opening ratio of the fixing member 104 is determined by dividing the sum of the total areas of the through holes in the fixing member by the bottom area of ​​the container.

[0049] The thickness of fixing member 104 is not particularly limited as long as it can sufficiently fix filtering member 105, but is, for example, 2 to 15 mm, and preferably 3 to 7 mm.

[0050] Furthermore, when the fixing member 104 has a disk shape, the deflection amount of the fixing member 104 with respect to a radius of 500 mm is preferably 10.0 mm or less. There is no lower limit to the deflection amount, but it is usually 0 mm or more. The deflection amount is preferably 0 to 3.0 mm, more preferably 0.1 to 2.0 mm, and particularly preferably 0.1 to 1.0 mm. When the deflection amount is within the above range, the filtering member 105 is easily fixed sufficiently even when stress caused by stirring is applied. The deflection amount can be kept within the above range by using the material of the fixing member 104 as described below, or by appropriately adjusting the thickness of the fixing member 104 and the through-holes 106. The amount of deflection of the fixing member 104 is a value measured by the following procedure. <Deflection measurement method> The fixed member is placed on a flat surface plate, and the height from the surface plate (excluding the thickness of the fixed member) is measured at any point on the periphery of the fixed member. Measurements are taken at four points rotated 90° from the first measurement point, and this is done on both the front and back sides of the fixed member for a total of eight points, and the maximum value of these is used as the amount of deflection.

[0051] The materials of the container 101, shaft 102, stirring blade 103, and fixing member 104 are not particularly limited, but from the viewpoint of heat resistance and corrosion resistance, they are preferably made of at least one selected from the group consisting of metal materials and materials in which metal is coated with resin. Examples of metal materials include iron, stainless steel, and aluminum. Examples of resins that coat metals include polytetrafluoroethylene (PTFE), ethylene tetrafluoroethylene (ETFE), and perfluoroalkoxyalkane (PFA). Among these, from the viewpoint of firmly fixing the filtering member 105, it is preferable that the fixing member 104 be made of the above materials. The shaft 102 and the stirring blade 103 may be made of a material consisting of a simple resin such as polytetrafluoroethylene (PTFE), ethylene tetrafluoroethylene (ETFE), or perfluoroalkoxyalkane (PFA).

[0052] <Recovery process and resupply process> The method for producing an organosilicon compound according to this embodiment preferably further comprises a recovery step of recovering the filtrate that has passed through the filter member 105 in a recovery container, and a resupply step of supplying the filtrate recovered in the recovery step to the storage container 101 when the volume of the liquid or slurry in the storage container 101 becomes 50% or less (more preferably 30% or less) of the volume of the storage container 101. That is, the filtration device 100 preferably further has a collection container for collecting the filtrate that has passed through the filtration member 105, and further has a supply device for re-supplying the filtrate collected in the collection container to the storage container 101 when the volume of the liquid or slurry in the storage container 101 becomes 50% or less (more preferably 30% or less) of the volume of the storage container 101.

[0053] By providing such a recovery step and re-supply step, the filtrate can be filtered again, thereby increasing the purity of the target recovered product. In addition, multiple filtration steps can be performed using a single filtration device, thereby reducing the costs of the device and operation.

[0054] The collection container is not particularly limited as long as it is a container that can contain a liquid, and for example, a container made of the same material as the storage container 101 and the fixing member 104 can be used.

[0055] The supply device is not particularly limited as long as it can transfer the filtrate in the collection container to the storage container 101, but an example is a method in which a pipe is connected from the collection container to the top of the storage container 101 and the filtrate in the collection container is transferred using pressurized nitrogen gas or a pump.

[0056] <Dissolution process> The method for producing an organosilicon compound according to this embodiment includes a dissolving step, which is performed after the filtration step, in which the salt produced in the reaction step is brought into contact with a dissolving agent containing a second alcohol having 1 to 3 carbon atoms to dissolve the salt. Hereinafter, the liquid in which the salt is dissolved in the dissolving step is also referred to as a dissolved liquid. The method for bringing the salt into contact with the dissolving agent is not particularly limited, and for example, the dissolving agent may be introduced into the container 101 after the filtrate is collected in the filtration step. By dissolving the salt after the filtration step in the dissolving step, the dissolved solution can be recovered from the outlet of the container 101 in the same way as the filtrate in the filtration step, which is excellent in workability.

[0057] If the storage container is equipped with an exhaust line, the solvent may be introduced through the exhaust line. When the reaction process is carried out in a storage container, low-molecular-weight silicon compounds produced by the reaction may adhere to and deposit on the exhaust line. By introducing the solvent through the exhaust line, the exhaust line can be cleaned at the same time. After that, the storage container and the exhaust line may be dried by further supplying an inert gas such as nitrogen.

[0058] In the dissolution step, it is preferable to carry out the dissolution while stirring in order to shorten the process time. The preferable stirring conditions are the same as those in the filtration step. In order to increase the solubility of the salt, the dissolving step may be carried out under heating, for example, at 20 to 60°C, or 30 to 40°C. The time for the dissolving step is not particularly limited as long as the salt is sufficiently dissolved, but may be, for example, 3 to 60 minutes, or 5 to 15 minutes.

[0059] After the dissolving step, the container may be washed by again adding the solubilizing agent to the container and stirring and filtering (washing step). The stirring conditions in the washing step may be the same as those in the dissolving step. The amount of the solubilizing agent added in the washing step is not particularly limited, but is, for example, 0.1 to 5 times, preferably 0.3 to 2 times, the amount used in the dissolving step.

[0060] <Solubilizer> The dissolving agent is used to dissolve the by-product salt produced in the reaction step, and contains a second alcohol having 1 to 3 carbon atoms. Specific examples of the second alcohol include methanol, ethanol, 1-propanol, and 2-propanol, and methanol is preferred from the viewpoint of the solubility of the by-product salt. The dissolving agent may contain components other than the second alcohol, such as water, ether solvents such as tetrahydrofuran, diethyl ether, diisopropyl ether, etc. The dissolving agent may also contain multiple types of second alcohols. The content of the second alcohol in the solubilizer is preferably 30% or more, more preferably 60% or more, and particularly preferably 100%.

[0061] From the viewpoint of sufficiently dissolving the by-product salt, it is preferable to supply the solubilizer in the dissolving step so that the amount of the second alcohol supplied is 0.5 times or more by mass relative to the amount of the salt. There is no particular upper limit to the supply amount, but from the viewpoint of cost, it is usually 20 times or less. The supply amount is more preferably 1 to 10 times, and particularly preferably 2 to 6 times. [Example]

[0062] Examples of the present invention will be described below, but the present invention is not limited to the following examples.

[0063] Example 1 The filtering device used was a cylindrical container with an inner diameter of 400 mm and a height of 300 mm, a shaft, and a stirring blade. The container was made of stainless steel and had an inner surface lined with polytetrafluoroethylene. The air cylinder was a CDM2B32-100Z manufactured by SMC Corporation, and the shaft and agitator blades were made of aluminum designed in-house and coated with polytetrafluoroethylene (PTFE) resin. The agitator blades were approximately conical, with a base diameter 0.6 times the inner diameter of the bottom of the container, and the angle between the base and the generatrix (taper angle) was 5°. One agitator blade was attached to the shaft at a height of 15 mm from the bottom of the container. A filter and a fixing member were also provided at the bottom of the container. The fixing member was a circular punched plate with an inner diameter of 400 mm and a thickness of 3 mm, coated with PTFE resin. The fixing member had multiple hexagonal through-holes, with an aperture ratio of 40% and a deflection of 1 mm per a radius of 500 mm. The filtering member used was ADVANTEC (registered trademark) No. 2 (trade name, manufactured by Advantec Toyo Kaisha, Ltd.), which was fixed by being sandwiched between two of the above-mentioned fixing members.

[0064] First, 279 g of magnesium particles and 9960 g of tetrahydrofuran were placed in a reaction flask, and then a mixed solution of 1453 g of 1,3-dibromopropane, 1075 g of methyltrichlorosilane, and 1038 g of tetrahydrofuran was gradually added. Then, a Grignard reaction was carried out under reflux conditions to obtain a halogenated silicon compound having a structure represented by formula (3).

[0065] The entire amount of the obtained silicon halide compound was placed in the container of a filtration device. Next, a mixed solution of 1,457 g of triethylamine, 971 g of tetrahydrofuran, and 461 g of methanol were added under stirring under the following conditions, and an alkoxylation reaction was carried out to obtain a reaction solution containing an alkoxysilane having a structure represented by formula (6). During this process, a by-product salt was generated, and the reaction solution became a slurry. After the addition, the thickness of the by-product salt in a stationary state was approximately 70 mm. <Stirring conditions> Stirring blade up and down stroke width: 100 mm -Agitator blade up and down speed: 100mm / s Air cylinder operating pressure: 0.4MPa

[0066] After stirring was stopped, filtration was carried out for 15 minutes while the container was pressurized at a maximum differential pressure of 50 kPa.

[0067] After the entire filtrate was collected from the outlet at the bottom of the container, approximately 2,250 g of by-product salt remained on the filter and fixing members. 8,000 mL of methanol was added to the container as a dissolving agent, and the container was stirred for 10 minutes at a speed of 200 mm / s, moving the stirring blades up and down. The by-product salt was completely dissolved, resulting in a homogeneous solution. The resulting solution was collected from the outlet into a waste container, and the by-product salt was successfully removed.

[0068] As can be seen from the above results, by producing an organosilicon compound using the method according to one embodiment of the present invention, by-product salts can be filtered and removed simply and safely, and workability is excellent. [Explanation of symbols]

[0069] 100 Filtration equipment 101 Containment Container 102 Shaft 103 Stirring blade 104 Fixing member 105 Filtration element 106 Through hole B busbar θ angle

Claims

1. A method for producing an organosilicon compound, comprising: a reaction step of reacting a silicon halide compound with a first alcohol to obtain a liquid or slurry containing an alkoxysilane; a filtration step of filtering the salt generated in the reaction step; and a dissolving step of contacting the salt with a dissolving agent containing a second alcohol having 1 to 3 carbon atoms after the filtering step to dissolve the salt; A method for producing an organosilicon compound, comprising:

2. 2. The method for producing an organosilicon compound according to claim 1, wherein the second alcohol is methanol.

3. 2. The method for producing an organosilicon compound according to claim 1, wherein the alkoxysilane is an alkoxysilane represented by the following formula (6): In formula (6), R １ each independently represents a hydrogen atom or a monovalent organic group, R ２ each independently represents an organic group, R ３ each independently represents an alkyl group, and n represents the number of repetitions and is an integer of 2 or more.

4. 4. The method for producing an organosilicon compound according to claim 1, wherein in the dissolving step, the amount of the second alcohol supplied is 0.5 times or more by mass relative to the amount of the salt.

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