JP2005314325A - MANUFACTURING METHOD OF beta-KETOESTER STRUCTURE-CONTAINING ORGANOSILICON COMPOUND - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a manufacturing method of a β-ketoester structure-containing organosilicon compound where a reaction initiates and proceeds always stably in each production, gives a small amount of by-products and attains a high yield. <P>SOLUTION: The manufacturing method of the β-ketoester structure-containing organosilicon compound represented by general formula (3) (wherein R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>and n are the same as below) comprises reacting an unsaturated group-containing β-ketoester compound represented by general formula (1) (wherein R<SP>1</SP>is a 1-6C alkyl group or a phenyl group) with a hydroalkoxysilane represented by general formula (2): HSiR<SP>2</SP><SB>n</SB>(OR<SP>3</SP>)<SB>3-n</SB>(wherein R<SP>2</SP>and R<SP>3</SP>are the same or different and are each a 1-6C alkyl group; and n is an integer of 0-2), where a platinum-vinylsiloxane complex is used as a catalyst. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a method for producing a β-ketoester structure-containing organosilicon compound useful as a raw material for a room temperature curable organopolysiloxane composition.

As a method for producing a β-ketoester structure-containing organosilicon compound, it is a known technique to produce an unsaturated group-containing β-ketoester compound and hydroalkoxysilane by using hydrochlorolation reaction in the presence of chloroplatinic acid as a catalyst. (Patent Documents 1 to 3: Japanese Patent Laid-Open Nos. 63-250390, 63-313793, and 11-323132). In addition, chloroplatinic acid (H ₂ PtCl ₆ .6H ₂ O) has a catalytic action even when added alone, but an alcohol solution is a homogeneous catalyst, and is called a spiel catalyst, and is most often used because of its simplicity. It is what.

In a conventional method for producing an organosilicon compound containing a β-ketoester structure, that is, a method in which an unsaturated group-containing β-ketoester compound and a hydroalkoxysilane are hydrosilylated using chloroplatinic acid as a catalyst, the following some methods There was a problem.
(1) There has been a problem that the start of the hydrosilylation reaction is not always stable in each production, and the progress of the reaction is unstable. More specifically, even if one raw material and chloroplatinic acid are charged and then the supply of the other raw material is started, the hydrosilylation reaction may not start immediately (if the reactivity is stable, the reaction When started, an increase in internal temperature due to reaction heat is immediately observed, but in the conventional production method, the reaction did not start and the internal temperature did not increase.) For this reason, a very long aging time may be required before the reaction is started. Furthermore, the reaction suddenly stops in the middle of the progress of the reaction, and the unreacted raw material that has accumulated suddenly restarts at the unpredictable indefinite stage. However, there is a case where heat generation tends to run away and the heat generation tends to run away.

  In addition, chloroplatinic acid used as a catalyst shows stable reactivity in the usual hydrosilylation reaction of olefins, but specifically unstable in the hydrosilylation reaction of unsaturated group-containing β-ketoester compounds. Indicates. For this reason, it is considered that the unsaturated group-containing β-ketoester compound contains a considerable amount of tautomeric enol species as an inherent property. Since the unsaturated group-containing β-ketoester compound has a diketone structure having two carbonyl groups sandwiching methylene, the hydrogen atom of methylene tends to be an active proton, It is known that a considerable amount of enol-type species which are tautomers coexist. The instability of the hydrosilylation reaction when an unsaturated group-containing β-ketoester compound is catalyzed by the aforementioned chloroplatinic acid is because the above enol-type chemical species or active protons interfere with the catalytic action of chloroplatinic acid. It is guessed.

  (2) In the conventional method, the reproducibility of the reaction yield is poor, the reaction may not be achieved, and a large amount of unreacted raw materials may remain, or a large amount of various by-products may be generated resulting in a low yield. It was. As for by-products in the conventional production method, as described in Japanese Patent Application Laid-Open No. 63-250390 (Patent Document 2), the enol form chemistry of the target β-ketoester structure-containing organosilicon compound is described. It is known that a compound in which a hydroxyl group of a species is transesterified with an alkoxy group on the same or different molecular silicon atom is easily formed. The transesterification reaction is presumed to be promoted by the catalytic action of the chlorine content of chloroplatinic acid.

  (3) In the conventional method, a technique of adding triphenylphosphine as a cocatalyst to a reaction system using chloroplatinic acid as a catalyst is also known (Patent Document 3: Japanese Patent Laid-Open No. 11-323132). Since the compound has the property of becoming a catalyst poison of a platinum catalyst, there is a problem that it is not preferable for an industrial large-scale production method (Non-patent Document 1: Kunio Ito, “Silicone Handbook”, page 27, Nikkan Kogyo. Newspaper company). In addition, triphenylphosphine is solid at room temperature, and when charged into a large-capacity reactor, there is a problem that it is difficult to handle and poor in workability as compared with a liquid compound.

  For this reason, in the method of producing a β-ketoester structure-containing organosilicon compound by hydrosilylation reaction of an unsaturated group-containing β-ketoester compound and hydroalkoxysilane, the initiation of the reaction and the progress of the reaction are always performed in each production. There is a need for a method that is stable and has a low reaction rate and a high reaction yield. In addition, there has been a demand for a method that does not require the addition of a substance that may adversely affect the reaction or the addition of complicated operations.

JP-A 63-250390 JP-A-63-331393 JP-A-11-323132 Edited by Kunio Ito “Silicone Handbook”, page 27, Nikkan Kogyo Shimbun

  The present invention has been made in view of the above circumstances, and a β-ketoester structure-containing organosilicon compound having a stable reaction start and progress of reaction in every production, a small amount of by-products, and a high reaction yield. It aims at providing the manufacturing method of.

  As a result of intensive studies to achieve the above object, the present inventor selected a platinum-vinylsiloxane complex as a catalyst, and hydrosilylated an unsaturated group-containing β-ketoester compound with a hydroalkoxysilane in the presence of the platinum catalyst. Surprisingly, the start of the hydrosilylation reaction and the progress of the reaction are always stable in each production, the reaction yield is high, the addition of a cocatalyst, etc. is not necessary, It has been found that no additional process is necessary. Further, when the reaction temperature is strictly controlled within a limited range of 60 to 100 ° C. during synthesis, it has been found that the amount of various by-products is further reduced and a higher reaction yield can be obtained, and the present invention has been made. It was.

（式中、Ｒ¹は炭素数１〜６のアルキル基又はフェニル基である。）
で表される不飽和基含有β−ケトエステル化合物と下記一般式（２）
ＨＳｉＲ² _n（ＯＲ³）_3-n （２）
（式中、Ｒ²及びＲ³は互いに同一又は異種の炭素数１〜６のアルキル基であり、ｎは０〜２の整数である。）
で表されるヒドロアルコキシシランとを反応させて、下記一般式（３）

（式中、Ｒ¹、Ｒ²、Ｒ³、ｎは上記と同様である。）
で表されるβ−ケトエステル構造含有有機ケイ素化合物を製造する方法において、触媒として白金−ビニルシロキサン錯体を使用することを特徴とするβ−ケトエステル構造含有有機ケイ素化合物の製造方法、
〔ＩＩ〕白金−ビニルシロキサン錯体が、１，３−ジビニル−１，１，３，３−テトラメチルジシロキサンを配位子とする白金錯体である〔Ｉ〕記載の有機ケイ素化合物の製造方法、
〔ＩＩＩ〕式（１）及び（３）におけるＲ¹がメチル基であり、式（２）及び（３）におけるＲ²及びＲ³がメチル基又はエチル基であり、ｎが０又は１である〔Ｉ〕又は〔ＩＩ〕記載の有機ケイ素化合物の製造方法、
〔ＩＶ〕反応温度が、６０〜１００℃の範囲であることを特徴とする〔Ｉ〕乃至〔ＩＩＩ〕のいずれかに記載の有機ケイ素化合物の製造方法、
を提供する。 That is, the present invention
[I] The following general formula (1)

(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms or a phenyl group.)
An unsaturated group-containing β-ketoester compound represented by the following general formula (2)
HSiR ² _n (OR ³ ) _3-n (2)
(In the formula, R ² and R ³ are the same or different alkyl groups having 1 to 6 carbon atoms, and n is an integer of 0 to 2.)
Is reacted with a hydroalkoxysilane represented by the following general formula (3):

(In the formula, R ¹ , R ² , R ³ and n are the same as above.)
A process for producing a β-ketoester structure-containing organosilicon compound represented by the formula, wherein a platinum-vinylsiloxane complex is used as a catalyst,
[II] The method for producing an organosilicon compound according to [I], wherein the platinum-vinylsiloxane complex is a platinum complex having 1,3-divinyl-1,1,3,3-tetramethyldisiloxane as a ligand,
[III] R ¹ in the formulas (1) and (3) is a methyl group, R ² and R ³ in the formulas (2) and (3) are a methyl group or an ethyl group, and n is 0 or 1 [I] or [II] production method of organosilicon compound,
[IV] The method for producing an organosilicon compound according to any one of [I] to [III], wherein the reaction temperature is in the range of 60 to 100 ° C.
I will provide a.

  According to the production method of the present invention, it is possible to obtain an organosilicon compound containing a β-ketoester structure in a high yield with a stable start of reaction and progress of reaction at each production, and with few by-products.

（式中、Ｒ¹は炭素数１〜６のアルキル基又はフェニル基である。） In the present invention, the unsaturated group-containing β-ketoester compound used as a raw material is represented by the following general formula (1).

(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms or a phenyl group.)

Here, R ¹ is an alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, or a phenyl group, and may be the same or different. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an isobutyl group, an n-pentyl group, and an n-hexyl group. Examples of the compound of the general formula (1) include the following.

In the present invention, the hydroalkoxysilane used by reacting with the above compound is a silane having one hydrogen atom (Si—H group) directly bonded to a silicon atom, which is represented by the following general formula (2).
HSiR ² _n (OR ³ ) _3-n (2)
(In the formula, R ² and R ³ are the same or different alkyl groups having 1 to 6 carbon atoms, and n is an integer of 0 to 2.)

Here, R ² and R ³ are alkyl groups having 1 to 6 carbon atoms, preferably 1 to ³ carbon atoms, which may be the same or different. Specific examples thereof include the same groups as those exemplified as the alkyl group for R ¹ .

  Typical examples of the hydrosilane compound represented by the above formula (2) include trimethoxysilane, triethoxysilane, methyldimethoxysilane, methyldiethoxysilane, ethyldimethoxysilane, ethyldiethoxysilane, methoxydiethoxysilane, and dimethoxy. Examples include ethoxysilane and methylmethoxyethoxysilane.

（式中、Ｍｅはメチル基、Ｅｔはエチル基を示す。） Specific examples of the β-ketoester structure-containing organosilicon compound obtained by hydrosilylation reaction of the unsaturated group-containing β-ketoester compound represented by the general formula (1) and the hydroxysilane compound represented by the general formula (2) include Specific examples include, but are not limited to: Specific reaction conditions will be described later.

(In the formula, Me represents a methyl group, and Et represents an ethyl group.)

  In the present invention, the platinum-vinylsiloxane complex used as a catalyst for the hydrosilylation reaction is a known compound generally called a Karstedt catalyst. Here, the vinyl siloxane includes all siloxanes including a unit in which a vinyl group is bonded to a silicon atom. If there is at least one unit in which a vinyl group is bonded to a silicon atom, the number of the units, There is no limit to the number of silicon atoms. Further, the number of vinyl groups bonded to the silicon atom may be one, two or three.

  The group bonded to the silicon atom other than the vinyl group is not particularly limited, and examples thereof include alkyl groups such as methyl group, ethyl group, propyl group, and butyl group, and aryl groups such as phenyl group. Further, at least one siloxy group is indispensable for achieving a siloxane structure. Vinylsiloxane may have either a chain structure or a cyclic structure, or a mixture of both.

  In particular, siloxanes having 2 to 4 silicon atoms having a vinyl group are preferable, and examples thereof include divinyldisiloxane, divinyltrisiloxane, divinyltetrasiloxane, trivinylcyclotrisiloxane, and tetravinylcyclotetrasiloxane. Among the above examples, 1,3-divinyl-1,1,3,3-tetramethyldisiloxane is particularly preferable because of its high catalyst performance and availability.

  In addition, there is no restriction | limiting in particular in the number which the vinyl group couple | bonded with the silicon atom coordinated to platinum, It is arbitrary by the number of the vinyl groups in vinylsiloxane. Preferably, a complex in which two molecules of divinyldisiloxane are allowed to act on one platinum atom is used. In this complex, divinyldisiloxane is not necessarily chelated with a platinum atom, and the platinum atom may be bonded to a vinyl group of a separate divinyldisiloxane molecule.

  The valence of platinum is preferably zero, but may be divalent or tetravalent. In addition to the vinyl siloxane, other ligands may be coordinated to the platinum atom. Examples thereof include diene compounds and compounds having a nitrile group. The platinum-vinylsiloxane complex may be used as it is dissolved or dispersed in the reaction solution, or may be used by being supported on an adsorbent such as activated carbon, silica gel, or alumina.

  The platinum-vinylsiloxane complex preferably contains as little chlorine as possible, and more preferably has a neutral pH range. As a method for reducing the chlorine content, after mixing chloroplatinic acid and vinyl siloxane, strip hydrogen chloride under reduced pressure heating conditions, etc., or remove free hydrogen chloride with alkali (sodium bicarbonate, sodium carbonate, etc.) Various general means such as summing are selected.

In the production method of the present invention, the amount of the platinum-vinylsiloxane complex used is arbitrary, but is about 1 × 10 ⁻⁷ to 1 × 10 ^{−3 with} respect to 1 mol of the unsaturated group-containing β-ketoester compound. The molar amount is preferable, and the amount used is preferably about 1 × 10 ⁻⁶ to 1 × 10 ⁻⁴ mol. If the amount used is too small, the reaction may not occur, and if it is too large, it may be economically disadvantageous. When the reaction temperature is preferably strictly controlled in the range of 60 to 100 ° C., more preferably 70 to 90 ° C., the reaction yield is further improved. When the reaction temperature is higher than 100 ° C., as a phenomenon newly confirmed by the present inventors, the decomposition reaction due to heat of the target β-ketoester structure-containing organosilicon compound itself as shown by the following chemical formula increases. There is a case. In the following formulae, Me represents a methyl group.

  On the other hand, if the reaction temperature is lower than 60 ° C., it may take time to start the hydrosilylation reaction between the unsaturated group-containing β-ketoester compound and the hydroalkoxysilane. In addition, the progress of the reaction may be slow, and in this case, a by-product is generated in which the hydroalkoxysilane accumulated in the system is converted to the same alkoxy group in which the hydrogen atom is bonded to the silicon atom. (For example, when trimethoxysilane is used, tetramethoxysilane is by-produced).

  In the reaction conditions of the production method of the present invention, the molar ratio of the unsaturated group-containing β-ketoester compound represented by the general formula (1) and the hydroalkoxysilane represented by the general formula (2) is arbitrary. It is not preferable to make the molar ratio excessive not only economically disadvantageous but also generating unnecessary by-products. The molar ratio of the unsaturated group-containing β-ketoester compound to hydroalkoxysilane is usually 2: 1 to 1: 2, particularly 0.9 to 1 of hydroalkoxysilane per mole of the unsaturated group-containing β-ketoester compound. It is preferable to use 1 mol.

  There is no particular limitation on the method for introducing the reaction raw material. For example, hydroalkoxysilane may be slowly dropped into an unsaturated group-containing β-ketoester compound in the presence of a platinum-vinylsiloxane complex while observing the exothermic state. . Further, an unsaturated group-containing β-ketoester compound may be similarly dropped into hydroalkoxysilane in the presence of a platinum-vinylsiloxane complex. A mixture of an unsaturated group-containing β-ketoester compound and hydroalkoxysilane may be added dropwise in the presence of a platinum-vinylsiloxane complex in a solvent. In addition, the reaction may be performed by any of batch, semi-batch and continuous methods.

  In the production method of the present invention, a reaction solvent is not particularly required, but when used, for example, aromatics such as toluene and xylene, aliphatics such as hexane, isooctane and decane, ethers such as THF, and the like. A solvent can be used. Moreover, you may use these solvents individually by 1 type or in mixture of 2 or more types.

  Furthermore, a known means for further activating the hydrosilylation reaction can be added as necessary. For example, dry air containing an appropriate amount of oxygen can be blown into the reaction system, and the use of various additives that promote the reaction is also applicable.

  As the unsaturated group-containing β-ketoester compound and hydroalkoxysilane, those treated with an adsorbent such as activated carbon, activated clay, alumina, silica gel, magnesium oxide or a combination of these adsorbents or molecular sieves are used. You can also

  The reaction pressure can be carried out at normal pressure or increased pressure, and is not particularly limited. Further, the reaction system is preferably replaced with an inert gas such as nitrogen or argon so as to avoid mixing of moisture, and is preferably sealed with the same gas during the reaction. When water is mixed, hydroalkoxysilane and the target product may be hydrolyzed to reduce the yield. Furthermore, in order to prevent moisture from entering the reaction system, it is preferable to use a raw material unsaturated group-containing β-ketoester compound having a low water content, more preferably water used after dehydration. Various known dehydration methods such as use of a dehydrating agent and azeotropic dehydration using a solvent are selected.

  The amount of water contained in the reaction system is more preferably 1000 ppm or less, preferably 200 ppm or less, and the closer to zero, the more desirable results are given.

  The β-ketoester structure-containing organosilicon compound obtained by the production method of the present invention has the ability to capture a metal as a chelate as a raw material for a room temperature-curable polyorganosiloxane composition exhibiting excellent adhesion to plastics. Therefore, it is useful as a raw material for a silane coupling agent having a metal scavenging ability, a metal adsorbent and a metal recovery agent from a solution. In addition, as a raw material for adhesives, insulating sealants, potting agents, and coating agents in the electrical and electronic industries (liquid crystal, wiring boards, etc.) and the automobile industry, curing agents such as metal-fixed catalysts and epoxy resins, and architectural use As a sealant raw material, it can be widely used in many fields.

  EXAMPLES Hereinafter, although an Example and a comparative example are shown and this invention is demonstrated concretely, this invention is not limited to these Examples.

[Example 1]
In a four-necked flask equipped with a dropping funnel, a reflux condenser, a stirrer, and a thermometer each sufficiently substituted with nitrogen, 142.2 g (1 mol) of allyl acetoacetate and platinum-1,3-divinyl- 0.10 g of a toluene solution of 1,1,3,3-tetramethyldisiloxane complex (containing 15 × 10 ⁻⁶ mol of platinum atom) was introduced and heated to 70 to 80 ° C. When 3.7 g (0.03 mol) of trimethoxysilane was added thereto, heat generation immediately occurred and the reaction temperature rose by 9 ° C. When gas chromatography (GC) was measured after 30 minutes, trimethoxysilane was completely consumed, and formation of 3-trimethoxysilylpropyl acetoacetate was observed.

  Next, 118.5 g (0.97 mol) of trimethoxysilane was added dropwise over about 5 hours. During the addition, the reaction temperature was controlled at 70-90 ° C. Although GC measurement was performed every hour, the remaining amount of trimethoxysilane was 0 to 0.2% by mass at any stage, and almost quantitative reaction was always in progress. At the end of the dropwise addition, there was only 0.1% by mass of trimethoxysilane remaining, and when the mixture was aged for 1 hour as it was, the residual trimethoxysilane was zero and the reaction was complete.

  As a result of GC measurement, the yield of 3-trimethoxysilylpropyl acetoacetate from trimethoxysilane was about 90%. In addition, almost no compound was detected in which the enol tautomer of the β-ketoester group of 3-trimethoxysilylpropyl acetoacetate and the methoxy group on the silicon atom were transesterified.

[Example 2]
42.6 g (0.3 mol) of allyl acetoacetate and platinum-1,3-divinyl-into a four-necked flask equipped with a dropping funnel sufficiently filled with nitrogen, a reflux condenser, a stirrer and a thermometer. 0.06 g of a toluene solution of 1,1,3,3-tetramethyldisiloxane complex (containing 9 × 10 ⁻⁶ mol of platinum atoms) was introduced and heated to 70 to 80 ° C. To this, 40.3 g (0.33 mol) of trimethoxysilane was added dropwise over about 2 hours. An exotherm of 5 ° C. or higher was immediately observed at the beginning of the dropping. During the addition, the reaction temperature was controlled at 70-90 ° C. There was no sudden change in temperature during the dropping, and almost no trimethoxysilane remained at the end of the dropping. Furthermore, after aging for 3 hours, the residual trimethoxysilane was completely zero and the reaction was complete.

When the infrared absorption spectrum of the reaction solution was measured, the absorption based on the Si—H group was completely lost. In addition, almost no compound was detected in which the enol tautomer of the β-ketoester group of 3-trimethoxysilylpropyl acetoacetate and the methoxy group on the silicon atom were transesterified. GC and ¹ H-NMR measurements confirmed that the yield of 3-trimethoxysilylpropyl acetoacetate was about 90%.

[Comparative Example 1]
Instead of a toluene solution of platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, 0.09 g of an isopropanol solution of chloroplatinic acid (H ₂ PtCl ₆ ) (platinum atom 9 × 10 ^{− The} same operation as in Example 2 was performed except that ⁶ mol) was used. As a result, even when the dropping of trimethoxysilane was started, there was hardly any exotherm resulting from the start of the hydrosilylation reaction that should have been observed at the beginning. While the temperature was adjusted to 70 to 80 ° C., the dropping was continued as it was, and the internal temperature suddenly rose about 20 ° C. suddenly during the dropping (the hydrosilylation reaction started suddenly).

The dripping of trimethoxysilane was stopped and cooled rapidly. Thereafter, the temperature was adjusted to 70 to 80 ° C., and the remaining trimethoxysilane was dropped (about 2 hours). After completion of dropping, the mixture was aged for 2 hours. GC measurement of the reaction solution confirmed that the yield of 3-trimethoxysilylpropyl acetoacetate was only about 30%. Unreacted allyl acetoacetate and trimethoxysilane remained, and the composition of the reaction solution was complicated by various by-products.
The same operation was repeated, but almost no exotherm was observed at the start of the reaction, and a sudden and sudden exotherm occurred during the dropwise addition of trimethoxysilane occurred in an unpredictable reaction stage every time. The yield also fluctuated depending on the batch (20 to 60%), and it was difficult to reach a constant value.

[Comparative Example 2]
Instead of an isopropanol solution of chloroplatinic acid (H ₂ PtCl _6), except for using the butanol solution 0.09g of chloroplatinic acid (H ₂ PtCl ₆₎ (containing platinum atoms 9 × 10 ^-6 mol.) Of The same operation as Comparative Example 1 was performed. Although the reaction was aged for 10 hours after completion of the dropwise addition of trimethoxysilane, the reaction hardly occurred, and the yield of 3-trimethoxysilylpropyl acetoacetate was about 1%.

（式中、Ｍｅはメチル基を示す。） [Comparative Example 3]
The same operation as in Example 2 was performed except that the reaction temperature was 100 to 120 ° C. As a result, almost no 3-trimethoxysilylpropyl acetoacetate was found in the reaction solution, and two types of by-products in the following reaction formula were detected in large quantities. Most of 3-trimethoxysilylpropyl acetoacetate is considered to be thermally decomposed by the route of the following reaction formula.
Therefore, it was confirmed that 3-trimethoxysilylpropyl acetoacetate has the property of being essentially thermally decomposed when the reaction temperature is 100 to 120 ° C. This result suggests that the reaction temperature is not preferably higher than 100 ° C.

(In the formula, Me represents a methyl group.)

[Comparative Example 4]
The same operation as in Example 1 was performed except that the reaction temperature was 50 to 60 ° C. As a result, the yield of 3-trimethoxysilylpropyl acetoacetate in the reaction solution was about 60%. Tetramethoxysilane was by-produced and was detected at about 15% by mass. This result suggests that the reaction temperature is less than 60 ° C.

Claims (4)

The following general formula (1)

(In the formula, R ¹ is an alkyl group having 1 to 6 carbon atoms or a phenyl group.)
An unsaturated group-containing β-ketoester compound represented by the following general formula (2)
HSiR ² _n (OR ³ ) _3-n (2)
(In the formula, R ² and R ³ are the same or different alkyl groups having 1 to 6 carbon atoms, and n is an integer of 0 to 2.)
Is reacted with a hydroalkoxysilane represented by the following general formula (3):

(In the formula, R ¹ , R ² , R ³ and n are the same as above.)
A process for producing an organosilicon compound having a β-ketoester structure represented by formula (1), wherein a platinum-vinylsiloxane complex is used as a catalyst.   The method for producing an organosilicon compound according to claim 1, wherein the platinum-vinylsiloxane complex is a platinum complex having 1,3-divinyl-1,1,3,3-tetramethyldisiloxane as a ligand. R ¹ in the formulas (1) and (3) is a methyl group, R ² and R ³ in the formulas (2) and (3) are a methyl group or an ethyl group, and n is 0 or 1. Or the manufacturing method of the organosilicon compound of 2. The method for producing an organosilicon compound according to any one of claims 1 to 3, wherein the reaction temperature is in the range of 60 to 100 ° C.