JPS636074B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention has the general formula: (However, R is CH ₂ CH ₂ O or CH ₂ CH ₂ CH ₂ O, and the oxygen is bonded to the carbonyl on the right side of the above general formula, and
is a halogen atom or an alkoxy group, and n is 1 to
The present invention provides bis(silylpropoxycarbonyloxy) alkanes represented by the formula (representing an integer of 4) and a method for producing the same. As is clear from the above definition, the term "bis(silylpropoxycarbonyloxy)alkane" used in the present invention is a general term including bis(silylpropoxycarbonyloxy)oxaalkane. Conventionally, functional alkylsilane compounds represented by Y-R-SiX ₃ (X is a halogen atom or an alkoxy group, Y is a functional group, R is a linear or branched alkylene group, etc.), such as 3-amino Propyltriethoxysilane, 2-cyanoethyltrichlorosilane, 2-methoxycarbonyltrimethoxysilane, etc. are known compounds that are known to be used as water repellent agents, lubricants, rust preventive agents, etc. on fiber surfaces. There is. The present inventor has been conducting research on the synthesis of various useful functional organosilicon compounds for many years, and has discovered a new compound with the general formula: (However, R is CH ₂ CH ₂ O or CH ₂ CH ₂ CH ₂ O, and the oxygen is bonded to the carbonyl on the right side of the above general formula,
X is a halogen atom or an alkoxy group, and n is 1
to synthesize a bis(silylpropoxycarbonyloxy)alkane represented by (representing an integer of 4),
After confirming its structure and usage, we have completed and provided the present invention. That is, the novel compound of the present invention, bis(silylpropoxycarbonyloxy)alkane, has the general formula: (However, R is CH ₂ CH ₂ O or CH ₂ CH ₂ CH ₂ O, the oxygen atom is bonded to the carbonyl on the right side of the above general formula, X is a halogen atom or an alkoxy group, and n
represents an integer from 1 to 4). In the above formula, the halogen atom is preferably a halogen atom such as chlorine, bromine, or fluorine atom, and the alkoxy group is preferably a lower alkoxy group having 1 to 6 carbon atoms such as methoxy group, ethoxy group, or n-propoxy group. used. The bis(silylpropoxycarbonyloxy)alkanes of the present invention, viz. In general, its properties differ somewhat depending on the type of X and the number of n, but it usually exists in the form of a colorless and transparent liquid at room temperature and normal pressure. Further, the bis(silylpropoxycarbonyloxy)alkane of the present invention can generally be confirmed to be each compound of the general formula by the following methods (a) to (d). (a) By measuring the infrared absorption spectrum (IR), a strong absorption based on the carbonyl group characteristic of carbonate compounds appears around 1740 to 1750 cm ^-1 . In addition, when the product, which is an isolated and purified colorless transparent liquid, is heated to a high temperature, e.g., 180°C or higher, it continuously generates bubbles and decomposes, that is, a decarboxylation reaction occurs. You can know that you belong to (b) ¹³ carbon nuclear magnetic resonance spectrum ( ¹³ C−nmr)
By measuring the number and type of methylene groups and carbonate groups present in the molecule,
Furthermore, when X in the above general formula is an alkoxy group, the number and type of the alkoxy group can be known. That is, in ¹³ C-nmr (tetramethylsilane standard), there is a peak based on the carbon atom of the carbonyl group specific to carbonate compounds at around 156 ppm, a peak based on the carbon atom of the methylene group adjacent to the oxygen atom of the carbonate around 70 ppm, A peak based on the carbon atom of the methylene group located at the center of the propylene group is shown around 23 ppm, and a peak based on the carbon atom of the methylene group adjacent to the silicon atom is shown around 5 to 22 ppm. Furthermore, when an ether bond exists in the molecule, a peak based on the carbon atom of the methylene group adjacent to the ether group appears around 70 ppm. In addition,
By relatively comparing the respective peak intensities, the number of each bonding group can be determined. (c) Measure the mass spectrum (ms) and each peak observed (generally the mass number expressed as m/e, which is the molecular weight of the ion divided by the number of electron charges e)
By calculating the compositional formula corresponding to , it is possible to estimate the binding mode and ultimately the molecular weight of the sample subjected to measurement. For example, in the above general formula, if X is a chlorine atom, m/
e179, 178, 177, 176, 175, 174
Extremely strong peaks corresponding to Cl ₃ SiCH ₂ CH ₂ CH ₂ , m/e 141, 140, 139, 138, 137
Shows a peak corresponding to Cl ₃ Si. Furthermore, if measurements are carried out extremely carefully, a molecular ion peak (M) corresponding to the corresponding molecular weight can be observed, although the intensity is weak. Furthermore, when X in the above general formula is an ethoxy group, (EtO) ₃ Si
In addition to the peak corresponding to m/e205 (EtO) ₃ SiCH ₂ CH ₂ CH ₂ , the peak corresponding to the corresponding molecular weight (M), which is considered to be the desorption of ethanol,
That is, the M-46 peak is observed. Similarly X
When is a methoxy group, there is a very strong peak corresponding to (CH ₃ O) ₃ Si at m/e121, m/e163
In addition to the peak corresponding to (CH ₃ O) ₃ SiCH ₂ CH ₂ CH ₂ , a peak that is thought to be due to methanol desorption from the peak (M) corresponding to the corresponding molecular weight, that is, a peak of M-32, was observed. Ru. Similarly, when X is another alkoxy, a unique peak can be observed. (d) Determine the weight percent of each of carbon, hydrogen, and silicon by elemental analysis, and then subtract the sum of the weight percent of each recognized element from 100 to determine the weight percent of oxygen.
can be calculated, and therefore the compositional formula of the product can be determined. The bis(silylpropoxycarbonyloxy)alkane of the present invention is a colorless and odorless transparent liquid with a high boiling point.As will be specifically shown in the examples below, as with general organic compounds, the higher the molecular weight, the higher the boiling point. tends to be higher. The bis(silylpropoxycarbonyloxy)alkanes of the present invention are well soluble in common organic solvents such as benzene, ether, hexane, chloroform, carbon tetrachloride, acetonitrile, and N.N-dimethylformamide. In the above general formula, when X is a halogen atom, when added to an alcohol, it reacts with the alcohol and generates hydrogen halide, and at the same time the halogen atom is substituted by an alkoxy group, resulting in a compound derived from the alcohol. It changes to dicarbonate, which is an alkoxy group. In addition, when X is an alkoxy group, when it is dissolved in a different type of alcohol, part of the alkoxy group or, depending on the conditions, all of the alkoxy group may be used as a solvent, depending on the amount of alcohol used as a solvent. It is common for the alkoxy group to change to a different type of alkoxy group. Also,
When the dicarbonate represented by the above general formula is added to a water-containing solvent, an exothermic hydrolysis reaction occurs,
Transforms into the corresponding polysilsesquioxane compound. At this time, the rate of hydrolysis reaction tends to be higher when X in the above general formula is a halogen atom than when it is an alkoxy group. Further, the hydrolysis is greatly promoted by adding bases such as sodium hydroxide, potassium hydroxide, and ammonia, or acids such as hydrochloric acid, sulfuric acid, and acetic acid to the solvent. When the bis(silylpropoxycarbonyloxy)alkane of the present invention is heated to 180° C. or higher without a solvent or in an inert solvent, a decarboxylation reaction occurs continuously. The decarboxylation reaction tends to become more intense as the heating temperature becomes higher. Note that the decomposed product after the decarboxylation reaction is also generally a colorless and transparent liquid. The method for producing the bis(silylpropoxycarbonyloxy)alkane of the present invention is not particularly limited and may be obtained by any method. A typical manufacturing method that is generally suitably employed will be described below. That is, a bis(allyloxycarbonyloxy)alkane represented by the following formula and a silane compound represented by the general formula HSiX ₃ (where X is a halogen atom or an alkoxy group) such as trihalogenosilane or trialkoxysilane are combined in the presence of a catalyst. By the reaction, the desired bis(silylpropoxycarbonyloxy)alkane can be obtained in good yield. The bis(allyloxycarbonyloxy)alkane represented by the above formula is not limited to its production method, and for example, those obtained by known production methods can be used without particular limitation. Further, trihalogenosilane or trialkoxysilane is a compound represented by the general formula HSiX ₃ (X is a halogen atom or an alkoxy group), and can be used without being limited to its manufacturing method. The catalyst used in the reaction is not particularly limited as long as it is a catalyst commonly used in so-called hydrosilylation reactions, but platinum compounds such as chloroplatinic acid are effective in small amounts. This is suitable because there are many cases. Representative examples of the reaction between bis(allyloxycarbonyloxy)alkane and trihalogenosilane or trialkoxysilane in the present invention will be described in detail in the Examples below.
Although the reaction can generally be carried out without a solvent, it is generally carried out in the presence of a solvent. The solvent is not particularly limited and can be used as long as it is a polar non-aqueous solvent that does not react with the raw materials or the catalyst, and generally includes hydrocarbon solvents such as benzene, toluene, and hexane; and halogenated carbonized solvents such as chloroform and carbon tetrachloride. Hydrogen solvent; ether solvents such as dimethyl ether and diethyl ether are preferably used. Further, the reaction conditions are not particularly limited, but may vary depending on the type of raw material, the type of catalyst, the presence or absence of a solvent, etc., so it is preferable to select suitable conditions in advance and carry out the reaction. Generally, it is sufficient to select a temperature of -20 to 160°C for several tens of minutes to 40 hours. Further, since the reaction pressure proceeds sufficiently under atmospheric pressure, it is usually sufficient to carry out the reaction at normal pressure, but it is also possible to carry out the reaction under increased pressure or reduced pressure if necessary. If the desired product is bis(trialkoxysilylpropoxycarbonyloxy)alkane, it can be obtained by reacting bis(allyloxycarbonyloxy)alkane and trialkoxysilane according to the above reaction formula, or by the following method. It can also be obtained by such a method. That is, the general formula (However, Y is a halogen atom and R is CH ₂ CH ₂ O or
The oxygen is bonded to the carbonyl of the above general formula with CH ₂ CH ₂ CH ₂ O, and n is an integer of 1 to 4). is an alkyl group) in the presence or absence of a catalyst. In this case, it is generally preferable to use a linear or branched alkyl group having 1 to 6 or more carbon atoms as the alkyl group in the above general formula. In addition, the catalyst in the above reaction is generally a base and can be used without particular limitation, especially ammonia,
Nitrogen-containing compounds such as primary to tertiary lower alkyl amines and aromatic amines are preferably used. Furthermore, as mentioned above, bis(trialkoxysilylpropoxycarbonyloxy) alkanes have the property that the lower the alkoxy group, the easier it is to be substituted with a higher alkoxy group. (Trialkoxysilylpropoxycarbonyloxy)
By contacting the alkane with an alcohol higher than the alkoxy group and continuously separating the lower alcohol produced by the substitution reaction by means such as fractional distillation, the desired alkoxy group-containing bis(trialkoxysilylpropoxycarbonyl) Oxy)
It can be an alkane. The bis(silylpropoxycarbonyloxy)alkane of the present invention is a compound containing a carbonate group and silicon at both ends, as is clear from the above general formula or from the description of the properties above. As mentioned above, the carbonate group is released as carbon dioxide gas by heating, and this property can be used as a blowing agent. Furthermore, since it has strong water repellency due to the silicon content, it can also be used as a water repellent. In this case, bis(silylpropoxycarbonyloxy)alkane can be partially or completely hydrolyzed to form a strong crosslinked film, so it can be used for inorganic materials such as glass, cement, mortar, etc.; paper, wood, cellulose; By applying it to the surface of various types of workpieces such as nylon, etc., water repellency can be imparted to the workpieces. EXAMPLES In order to explain the present invention more specifically, examples and application examples will be described below, but the present invention is not limited to these examples. Example 1 1,5-bis(allyloxycarbonyloxy)-3-oxa-pentane

【formula】

Chloroplatinic acid hexahydrate (110 mg) was added to a mixture of [Formula] (41.3 g., 0.15 mol), trichlorosilane (64.2 g) and anhydrous n-hexane (100 ml), and the mixture was heated under reflux for 8 hours with magnetic stirring. did. After removing low-boiling components from the reaction mixture by atmospheric distillation, high-boiling components were carefully distilled under high vacuum (approximately 0.1 mmHg) while gradually heating on an oil bath to 70°C and finally to 130°C. I left. The reaction product changed from pale yellow to dark yellow by the above-mentioned heated distillation. A small amount of black precipitate was passed through a dry box to obtain a blackish, slightly viscous liquid (79.8 g). Measurement of the infrared absorption spectrum showed a strong absorption at 1745 cm ^-1 due to the carbonyl bond of the carbonate group. Its elemental analysis values are C26.65%, H4.18%, and C ₁₂ H ₂₀ O ₇ Cl ₆ Si ₂
C26.43%, H3.70, which is the calculated value for (545.19)
% was in very good agreement. In addition, when mass spectra were measured, molecular ion peaks (M) m/e 265, 263, which were weak in intensity but corresponded to the molecular weight, were found at m/e 547, 545, and 543. peaks corresponding to m/e223, 221

A peak corresponding to [Formula], a peak corresponding to Cl ₃ SiCH ₂ CH ₂ CH ₂ at m/e 177 and 175, and a peak corresponding to Cl ₃ Si at m/e 135 and 133 were shown. Furthermore, ¹³ C-nuclear magnetic resonance spectrum ( ¹³ C-nmr) was measured. The analysis results of each peak (chemical shift value: δppm; based on tetramethylsilane) were as follows. From the above results, the isolated product is the raw material 1.
5-bis(allyloxycarbonyloxy)-3
It was revealed that the two allyl groups in -oxa-pentane were trichlorosilylated 1,5-bis(trichlorosilylpropoxycarbonyloxy)-3-oxa-pentane. The yield was 97.0% based on the 1,5-bis(allyloxycarbonyloxy)-3-oxa-pentane used. Example 2 1,2-bis(allyloxycarbonyloxy)ethane (46.0 g., 0.2 mol), trichlorosilane (90.2 g), anhydrous n-hexane (150 ml), chloroplatinic acid hexahydrate (100 mg) The mixture was reacted and post-treated in the same manner as in Example 1 to obtain a dark yellow liquid (48.0 g). Measurement of the infrared absorption spectrum showed a strong absorption at 1750 cm ^-1 due to the carbonyl bond of the carbonate group. Its elemental analysis values are C23.14%, H3.63%,
C23.96%, H3.22%, Cl42.45% which is Cl43.02% and calculated value for C ₁₀ H ₁₆ O ₆ Cl ₆ Si ₂ (501.15)
matched. In mass spectrometry, in addition to the molecular ion peak (M), Cl ₃

【formula】

[Formula] Cl ₃ SiCH ₂ CH ₂ CH ₂ and Cl ₃ Si peaks were observed. Furthermore, the analytical results of ¹³ C-nmr measurement were as follows. From the above results, the isolated product is 1,2-bis(trichlorosilylpropoxycarbonyloxy)
It became clear that it was ethane. The yield was 95.8% based on the 1,2-bis(allyloxycarbonyloxy)ethane used. Example 3 1,3-bis(allyloxycarbonyloxy)propane (24.48 g., 0.1 mol), trichlorosilane (45.1 g), anhydrous cyclohexane (100 ml),
A mixture of chloroplatinic acid hexahydrate (60 mg) was reacted and post-treated in the same manner as in Example 1 to obtain a dark yellow liquid (49.8 g). Infrared absorption spectrum measurement showed an absorption based on carbonyl bond at 1745 cm ^-1 . Its elemental analysis value is C24.98%,
H3.71%, Cl40.55% and C ₁₁ H ₁₈ O ₆ Cl ₆ Si ₂
Calculated values for (515.18) C25.64%, H3.52%,
It matched with Cl41.29%. In addition to the molecular ion peak (M) in mass spectrometry,

[Formula] Cl ₃ SiCH ₂ CH ₂ CH ₂ and Cl ₃ Si peaks were observed. From the above results, the product is 1,3-bis(trichlorosilylpropoxycarbonyloxy)
It turned out to be propane. The yield is
It was 96.6%. Example 4 1,5-bis(trichlorosilylpropoxycarbonyloxy)-3-oxa-pentane (64.4
g. , 0.12 mol) was slowly added dropwise to the mixture while stirring in a cryogen bath using sodium chloride/water and a mixture of anhydrous methanol (70 ml) and anhydrous benzene (70 ml). After continuing to cool and stir for 2 hours after dropping,
Furthermore, under the same conditions, dry ammonia gas was bubbled through the flask until no white precipitate of ammonium chloride was formed, and excess ammonia gas was removed by bubbling nitrogen gas through the flask. Remove the formed ammonium chloride precipitate by suction filtration,
Furthermore, after removing the low boiling point components contained in the liquid by distillation, the high boiling point components are further removed by distillation.
The temperature was gradually and carefully distilled off at high vacuum (0.1 mmHg) to 70°C and finally to 120°C. The vacuum distillation distilled very little liquid. When the infrared absorption spectrum of the obtained almost colorless and transparent liquid (66.8 g) was measured, it showed a strong absorption at 1745 cm ^-1 due to the carbonyl bond of the carbonate group. Its elemental analysis values are C48.32% and H8.58%, which are calculated values for C ₂₄ H ₅₀ O ₁₃ Si ₂ (602.82).
It matched extremely well with C47.82% and H8.36%. In addition, when we measured the mass spectrum, we found a peak at m/e556 that is thought to be due to the desorption of ethanol from the molecular ion peak (M) corresponding to the molecular weight.
A peak of M-46 was observed. In addition, m/e205 has a peak corresponding to (EtO) ₃ SiCH ₂ CH ₂ CH ₂ , M/
A peak corresponding to (EtO) ₃ Si was shown at e163.
Furthermore, ¹³ C-nmr was measured. The analysis results for each peak were as follows. From the above results, the product is 1,5-bis(triethoxysilylpropoxycarbonyloxy)-
It became clear that it was 3-oxa-pentane. The yield was 93.9%. Example 5 1,5-bis(trichlorosilylpropoxycarbonyloxy)-3-oxa-pentane (64.4
g. , 0.12 mol), an almost colorless and transparent liquid (59.3 g) was prepared in the same manner as in Example 4, except that anhydrous methanol was used instead of anhydrous ethanol.
I got it. Infrared absorption spectrum measurement showed an absorption at 1745 cm ^-1 due to the carbonyl bond of the carbonate group. _The elemental analysis values were C42.10% and _H7.09 %, which matched the calculated values for _C18H38O13Si2 (518.66) _, C41.68% and H7.38%. In addition, when the mass spectrum was measured, there was a peak at m/e 486 that is considered to be the desorption of methanol from the molecular ion peak (M) corresponding to the molecular weight, that is, a peak at M-32, and (CH ₃ O) ₃ SiCH at m/e 163. ₂ CH ₂ CH ₂
A peak corresponding to (CH ₃ O) ₃ Si was observed at m/e121. Furthermore, ¹³ C−nmr
was measured. The analysis results for each peak were as follows. From the above results, the product is 1,5-bis(trimethoxysilylpropoxycarbonyloxy)-
It became clear that it was 3-oxa-pentane. The yield was 95.2%. Example 6 1,5-bis(allyloxycarbonyloxy)-3-oxa-pentane (41.3 g., 0.15 mol), triethoxysilane (65.72 g), anhydrous n-
Hexane (100ml), chloroplatinic acid hexahydrate (100ml)
mg) was stirred for 3 hours while cooling on a water bath, and then further stirred on an oil bath (80°C) for 3 hours. A small amount of insoluble black precipitate was removed by suction filtration, and low-boiling components in the liquid were removed by distillation. Furthermore, a very small amount of high boiling point components are added to the oil bath.
Careful vacuum distillation was performed below 120°C. Various spectral measurements were performed on the liquid product (88.0 g) thus obtained, and 1,5-bis(triethoxysilylpropoxycarbonyloxy)-3 obtained by separately describing the synthesis method in Example 4 was obtained. It was confirmed that it was the same as -oxa-pentane. The yield is 1,5-bis(allyloxycarbonyloxy)
It was 96.4% based on -3-oxapentane. Example 7 1,8-bis(allyloxycarbonyloxy)-3,6-dioxa-octane

【formula】

(31.8g., 0.1mol), tri(n-hexoxy)
Silane (99.5g), chloroplatinic acid hexahydrate (100g)
mg) mixture was stirred at room temperature overnight, and then further stirred on an oil bath (80°C) for 3 hours. The reaction mixture was treated as in Example 6 to form a dark viscous liquid (93.9 g).
I got it. Infrared absorption spectrum measurement showed an absorption at 1745 cm ^-1 due to the carbonyl bond of the carbonate group. Its elemental analysis values are C61.92%, H11.08%
The calculated values for C ₅₀ H ₁₀₂ O ₁₄ Si ₂ (983.50) were 61.06% for C and 10.45% for H. When the mass spectrum was measured, m/e373 (n-
_The peak _{corresponding to C6H13O} ) _{3SiCH2CH2CH2 ,}
A peak corresponding to (n-C ₆ H ₁₃ O) ₃ Si was shown at m/e331. From the above results, the product is 1.8-
It became clear that it was bis[tri(n-hexoxy)silylpropoxycarbonyloxy]-3,6-dioxaoctane. The yield was 95.5%. Example 8 1.11 in a 300ml stainless steel autoclave
-bis(allyloxycarbonyloxy)-3.
6,9-trioxer-undecane (36.2 g., 0.1 mol), anhydrous heptane (80 ml), and chloroplatinic acid hexahydrate (100 mg) were added, and the autoclave was cooled on a liquid nitrogen bath. Next, trifluorosilane (50 ml) was added and the mixture was gradually warmed to room temperature over about 1 hour while stirring, and stirring was continued overnight. Furthermore, the autoclave was immersed in an oil bath and gradually warmed to 80°C over 2 hours, and the reaction was completed by heating and stirring at 80°C for 4 hours. After the reaction was completed, excess trifluorosilane was first removed by bubbling nitrogen gas, and the reaction mixture solution was carefully taken out of the autoclave and transferred into a flask. After removing low-boiling components by vacuum distillation, high-boiling components in the remaining liquid were further removed by careful vacuum distillation while gradually heating the liquid to 70°C on an oil bath and finally to 120°C. . The small amount of solid present in the residue was removed by filtration in a dry box, yielding a viscous liquid (50.4 g). Measurement of the infrared absorption spectrum showed a strong absorption at 1750 cm ^-1 due to the carbonyl bond of the carbonate group.
Its elemental analysis values are C36.80%, H5.74%,
This is the calculated value for C ₁₆ H ₂₈ O ₉ F ₆ Si ₂ (534.56)
It matched C35.95% and H5.28%. Also, when I measured the mass spectrum, it was m/e171.

[Formula] A peak corresponding to F ₃ SiCH ₂ CH ₂ CH ₂ was shown at m/e127, and a peak corresponding to F ₃ Si was shown at m/e85. The above results revealed that the product was 1,11-bis(trifluorosilylpropoxycarbonyloxy)-3,6,9-trioxa-undecane. The yield is
It was 94.3%. Application example 1 1,5-bis(trichlorosilylpropoxycarbonyloxy)-3-oxa- obtained in Example 1
Pentane (1.0 g) was dissolved in hexane (100 ml) to prepare a 1 w/v% solution. A glass piece was immersed in the solution and then gradually dried. When the contact angle of the treated glass piece was measured, it showed a value of 103°. An increase in water repellency was also clearly observed by comparing the behavior of adhering water droplets with glass pieces not treated with the solution. Application example 2 1,5-bis(triethoxysilylpropoxycarbonyloxy)-3-oxa-pentane (10 g) obtained in Example 4 was added to aqueous ethanol (100 ml).
to prepare a 10 w/v% solution. Add 2 to the solution, which was previously dried in a dryer at 50°C until it reached a constant weight.
One of the nylon sheets (50 mm square) was soaked in the solution and brought into sufficient contact with the solution, then taken out from the solution and air-dried. The sample piece was again stored in a dryer at 50°C and dried until it reached a constant weight, and then immersed together with the untreated sample piece in pure water (100 ml) at 23°C for 24 hours. The water absorption rate of each specimen was determined by removing the specimen from the immersion bath, wiping it with dry gauze, and then measuring the weight of both specimens. As a result, the water absorption rate of the test piece treated with the 1,5-bis(triethoxysilylpropoxycarbonyloxy)-3-oxapentane solution was 1/12 of that of the untreated test piece.

Claims (1)

[Claims] 1 General formula, (However, X is a halogen atom or an alkoxy group,
R is CH ₂ CH ₂ O or CH ₂ CH ₂ CH ₂ O, and the oxygen is bonded to the carbonyl on the right side of the above general formula, and n is 1 to
bis(silylpropoxycarbonyloxy)alkane represented by 4). 2 general formula, (However, R is CH ₂ CH ₂ O or CH ₂ CH ₂ CH ₂ O, and the oxygen is bonded to the carbonyl on the right side of the above general formula, and n
is an integer from 1 to 4) and the general formula
A general formula characterized by reacting a silane compound represented by HSiX ₃ (where X is a halogen atom or an alkoxy group) in the presence of a catalyst. (However, X is a halogen atom or an alkoxy group,
R is CH ₂ CH ₂ O or CH ₂ CH ₂ CH ₂ O, and n is 1 to
A method for producing a bis(silylpropoxycarbonyloxy)alkane represented by (an integer of 4). 3 General formula (However, Y is a halogen atom, R is CH ₂ CH ₂ O or CH ₂ CH ₂ CH ₂ O, and the oxygen is bonded to the carbonyl on the right side of the above general formula, and n is an integer from 1 to 4)
It is characterized by reacting a bis(silylpropoxycarbonyloxy)alkane represented by with an alcohol represented by the general formula R′OH (wherein R′ is an alkyl group) in the presence or absence of a catalyst. A method for producing bis(trialkoxysilylpropoxycarbonyloxy)alkane.