METHOD FOR PRODUCING SILANE COMPOUND

Abstract

Provided is a method for producing a silane compound, which does not produce corrosive substances such as acids, does not use organic solvents and which contributes to a reduction in environmental load. This method for producing a silane compound has D) a siloxane decomposition step for heating a mixture containing: a siloxane compound A), which is a cyclic siloxane compound A-1) represented by formula (1), a linear siloxane compound A-2) represented by formula (2) and/or a silsesquioxane compound that is represented by formula (3) and has a siloxane bond as a main chain skeleton; a carbonate compound B) including at least one of a diaryl carbonate, a dialkyl carbonate and a monoalkylmonoaryl carbonate; and a basic compound catalyst C). The step D) further includes subjecting the siloxane compound A) to alkoxylation and/or aryloxylation. (In the formulae, R.sup.1 to R.sup.5, X, n, m and pare as described in the description of the present application.)

##STR00001##

Claims

1. A method for producing a silane compound, including, at least, any one of a diaryloxy silane compound, a dialkoxy silane compound, a monoaryloxymonoalkoxy silane compound, a triaryloxy silane compound, and a trialkoxy silane compound, wherein the method has D) a siloxane decomposition step of heating a mixture comprising: A) a siloxane compound(s) that are A-1) a cyclic siloxane compound represented by the following formula (1), A-2) a linear siloxane compound represented by the following formula (2), and/or a silsesquioxane compound comprising a siloxane bond as a main chain skeleton, represented by the following formula (3), B) a carbonate compound including, at least, any one of diaryl carbonate, dialkyl carbonate, and monoalkylmonoaryl carbonate, and C) a basic compound catalyst, so as to alkoxylate and/or aryloxylate A) the siloxane compound(s): ##STR00018## wherein R.sup.1 and R.sup.2 each independently represent an alkyl group, an alkenyl group, or an aryl group, each optionally having a substituent, and n represents an integer of 3 or more and 30 or less, ##STR00019## wherein R.sup.3 and R.sup.4 each independently represent an alkyl group, an alkenyl group, or an aryl group, each optionally having a substituent, m represents an integer of 2 or more and 10000 or less, and X each independently represents a hydrogen atom, a hydroxyl group, an alkoxy group optionally having a substituent and having a total carbon number of 1 to 10, a hydrocarbon group optionally having a substituent, optionally having an oxygen atom or a nitrogen atom and having a total carbon number of 1 to 10, or an amino group optionally having a substituent, and
[R.sup.5SiO.sub.1.5]p  (3) wherein R.sup.5 represents an alkyl group containing 1 to 4 carbon atoms, an alkenyl group containing 2 to 4 carbon atoms, or an aryl group containing 6 to 12 carbon atoms, each optionally having a substituent, and p represents an integer of 4 or more and 24 or less.

2. A method for producing a silane compound, including, at least, any one of a diaryloxy silane compound, a dialkoxy silane compound, and a monoaryloxymonoalkoxy silane compound, wherein the method has D) a siloxane decomposition step of heating a mixture comprising: A) a siloxane compound(s) that are A-1) a cyclic siloxane compound represented by the following formula (1), and/or A-2) a linear siloxane compound represented by the following formula (2), B) a carbonate compound including, at least, any one of diaryl carbonate, dialkyl carbonate, and monoalkylmonoaryl carbonate, and C) a basic compound catalyst, so as to alkoxylate and/or aryloxylate A) the siloxane compound(s): ##STR00020## wherein R.sup.1 and R.sup.2 each independently represent an alkyl group, an alkenyl group, or an aryl group, each optionally having a substituent, and n represents an integer of 3 or more and 30 or less, and ##STR00021## wherein R.sup.3 and R.sup.4 each independently represent an alkyl group, an alkenyl group, or an aryl group, each optionally having a substituent, m represents an integer of 2 or more and 10000 or less, and X each independently represents a hydrogen atom, a hydroxyl group, an alkoxy group optionally having a substituent and having a total carbon number of 1 to 10, a hydrocarbon group optionally having a substituent, optionally having an oxygen atom or a nitrogen atom and having a total carbon number of 1 to 10, or an amino group optionally having a substituent.

3. The method for producing a silane compound according to claim 1, wherein the R.sup.1 to R.sup.4 each independently represent an alkyl group or an alkenyl group having a total carbon number of 1 to 8, or an aryl group having a total carbon number of 6 to 30, each optionally having a substituent.

4. The method for producing a silane compound according to claim 3, wherein the R.sup.1 to R.sup.4 each independently represent any one selected from the group consisting of a methyl group, a phenyl group, a vinyl group, and a propyl group.

5. The method for producing a silane compound according to claim 1, wherein B) the diaryl carbonate includes diphenyl carbonate.

6. The method for producing a silane compound according to claim 1, wherein the number of carbon atoms contained in the alkyl group in B) the dialkyl carbonate is 4 or less.

7. The method for producing a silane compound according to claim 1, wherein C) the basic compound catalyst includes an alkali metal carbonate or an alkali metal hydroxide.

8. The method for producing a silane compound according to claim 7, wherein C) the basic compound catalyst includes, at least, either cesium carbonate or potassium carbonate.

9. The method for producing a silane compound according to claim 1, wherein, in D) the siloxane decomposition step, the ratio x of the molar amount of B) the carbonate compound to the Si molar amount of A) the siloxane compound is x≥1.

10. The method for producing a silane compound according to claim 1, wherein, in D) the siloxane decomposition step, the ratio x of the molar amount of B) the carbonate compound to the Si molar amount of A) the siloxane compound is 0.8<x<2.0.

11. The method for producing a silane compound according to claim 1, wherein, in D) the siloxane decomposition step, the ratio y of the molar ratio of C) the basic compound catalyst to the Si molar amount of A) the siloxane compound is 0.0001 mmol/mol≤y≤20 mmol/mol.

12. The method for producing a silane compound according to claim 1, wherein, in D) the siloxane decomposition step, the temperature applied to decompose A) the siloxane compound is 50° C. or higher and 300° C. or lower.

13. The method for producing a silane compound according to claim 12, wherein, in D) the siloxane decomposition step, the temperature applied to decompose A) the siloxane compound is 50° C. or higher and 150° C. or lower.

14. The method for producing a silane compound according to claim 1, wherein the molecular weight of A-1) the cyclic siloxane compound represented by the formula (1) is 2,000 or less, the molecular weight of A-2) the linear siloxane compound represented by the formula (2) is 60,000 or less, and the molecular weight of A-3) the silsesquioxane compound represented by the formula (3) is 3,500 or less.

15. The method for producing a silane compound according to claim 1, which further has E) a distillation step/a recrystallization step that is, at least, any one of a distillation step of distilling the silane compound generated by D) the siloxane decomposition step, and a recrystallization step of recrystallizing the silane compound generated by D) the siloxane decomposition step.

16. The method for producing a silane compound according to claim 14, wherein the pressure applied in E) the distillation step is 1 hPa or more and 20 hPa or less.

17. The method for producing a silane compound according to claim 1, which further has F) a dropping step of adding A) the siloxane compound dropwise to a mixture comprising B) the carbonate compound and C) the basic compound catalyst.

Description

EXAMPLES

<Evaluation Item>

[0103] NMR: The chemical shift in the following .sup.1H-NMR analyses was based on 7.24 ppm that is a peak of CDCl.sub.3.

Example 1

[0104] Decamethylcyclopentasiloxane (7.5 g; 20.2 mmol; Si molar amount: 101.0 mmol), diphenyl carbonate (21.6 g; 101.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0105] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was confirmed to be 100%.

[0106] Subsequently, the reaction mixture was cooled to 40° C., and was then subjected to reduced-pressure distillation at a degree of pressure reduction of 4 hPa and at 150° C., so as to obtain 23.7 g of a colorless oily component.

[0107] The obtained oily component was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane (DMDPS) and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 98.6:1.4.

[0108] The yield of the molar amount of dimethyldiphenoxy silane obtained from the weight of the obtained oily component and the above-described molar ratio was 96.0%, with respect to the molar amount of silicon atoms contained in the decamethylcyclopentasiloxane.

[0109] Dimethyldiphenoxy silane (′H-NMR (CDCl.sub.3, 500 MHz, 6; ppm)=0.378 (s; 6H), 6.942, 6.944 (d; 4H), 6.959, 6.961, 6.995 (t; 2H), 7.230, 7.245, 7.257 (t; 4H)).

[0110] It is to be noted that the siloxane decomposition reaction performed in the present example is represented by the following formula (4-1), and that 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained as a by-product, as well as DMDPS as a main product.

##STR00010##

Example 2

[0111] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (23.6 g; 110.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0112] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was confirmed to be 100%.

[0113] Subsequently, the reaction mixture was cooled to 40° C., and was then subjected to reduced-pressure distillation at a degree of pressure reduction of 4 hPa and at 150° C., so as to obtain 25.1 g of a colorless oily component.

[0114] The obtained oily component was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 99.8:0.2. In addition, a proton peak at a meta position of the carbonate group based on the diphenyl carbonate was also observed at 7.406 ppm.

[0115] The yield of the molar amount of dimethyldiphenoxy silane, which was obtained by subtracting the weight of diphenyl carbonate calculated from the peak area derived from the mixed diphenyl carbonate, from the weight of the obtained oily component, and then using the above-described molar ratio, was 97.7%, with respect to the molar amount of silicon atoms contained in the decamethylcyclopentasiloxane.

Example 3

[0116] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (32.1 g; 150.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0117] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was confirmed to be 100%.

[0118] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 98.8:1.2.

Example 4

[0119] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (19.3 g; 90.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0120] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was confirmed to be 100%.

[0121] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 93.2:6.8.

Example 5

[0122] Octaphenylcyclotetrasiloxane represented by the following formula (5) (melting point: 197° C.; molecular weight: 793.17) (14.9 g; 18.8 mmol; Si molar amount: 75.0 mmol), diphenyl carbonate (16.1 g; 75.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 10 minutes.

##STR00011##

[0123] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a proton peak at a para position of the octaphenylcyclotetrasiloxane was not observed, and the conversion percentage of the octaphenylcyclotetrasiloxane was confirmed to be 100%.

[0124] To the reaction mixture that had been cooled to room temperature and had been then solidified, 20 g of heptane was added, and the obtained mixture was heated to 90° C., followed by hot filtration. The obtained filtrate was left at room temperature for 3 days, so that a white crystal was precipitated. Thereafter, 10 g of heptane cooled to 5° C. was further added to the crystal, and the obtained mixture was filtrated. The thus obtained crystal was removed from the filter paper, and was then dried at 40° C., at a degree of pressure reduction of 1 hPa for 45 hours, so as to obtain 24.1 g of white powders. The obtained powders were analyzed by .sup.1H-NMR. As a result, peaks derived from diphenyldiphenoxy silane and 1,3-diphenoxy-1,1,3,3-tetraphenyldisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,3-diphenoxy-1,1,3,3-tetraphenyldisiloxane was obtained from the peak area ratio, and as a result, it was 95.4:4.6.

[0125] The yield of the molar amount of diphenyldiphenoxy silane, which was obtained from the weight of the obtained white powders and the above-described molar ratio, was 81.1%, with respect to the molar amount of silicon atoms contained in the octaphenylcyclotetrasiloxane.

[0126] Diphenyldiphenoxy silane (′H-NMR (CDCl 3,500 MHz, 6; ppm)=6.915, 6.927, 6.939, 6.952, 6.965 (p; 6H), 7.142, 7.155, 7.169 (t; 4H), 7.354, 7.366, 7.379 (t; 4H), 7.425, 7.437, 7.449 (t; 2H)), 7.750, 7.762 (d; 4H).

Example 6

[0127] Octaphenylcyclotetrasiloxane (14.9 g; 18.8 mmol; Si molar amount: 75.0 mmol), diphenyl carbonate (16.9 g; 78.8 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 10 minutes.

[0128] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a proton peak at a para position of the octaphenylcyclotetrasiloxane was not observed, and the conversion percentage of the octaphenylcyclotetrasiloxane was confirmed to be 100%.

[0129] To the reaction mixture that had been cooled to room temperature and had been then solidified, 20 g of heptane was added, and the obtained mixture was heated to 90° C., followed by hot filtration. The obtained filtrate was left at room temperature for 3 days, so that a white crystal was precipitated. Thereafter, 10 g of heptane cooled to 5° C. was further added to the crystal, and the obtained mixture was filtrated. The thus obtained crystal was removed from the filter paper, and was then dried at 40° C., at a degree of pressure reduction of 1 hPa for 45 hours, so as to obtain 24.4 g of white powders.

[0130] The obtained powders were analyzed by .sup.1H-NMR. As a result, peaks derived from diphenyldiphenoxy silane and 1,3-diphenoxy-1,1,3,3-tetraphenyldisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,3-diphenoxy-1,1,3,3-tetraphenyldisiloxane was obtained from the peak area ratio, and as a result, it was 99.5:0.5.

[0131] The yield of the molar amount of diphenyldiphenoxy silane, which was obtained from the weight of the obtained white powders and the above-described molar ratio, was 87.6%, with respect to the molar amount of silicon atoms contained in the octaphenylcyclotetrasiloxane.

Example 7

[0132] Octaphenylcyclotetrasiloxane (14.9 g; 18.8 mmol; Si molar amount: 75.0 mmol), diphenyl carbonate (17.7 g; 82.6 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0133] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a proton peak at a para position of the octaphenylcyclotetrasiloxane was not observed, and the conversion percentage of the octaphenylcyclotetrasiloxane was confirmed to be 100%.

[0134] To the reaction mixture that had been cooled to room temperature and had been then solidified, 20 g of heptane was added, and the obtained mixture was heated to 90° C., followed by hot filtration. The obtained filtrate was left at room temperature for 3 days, so that a white crystal was precipitated. Thereafter, 10 g of heptane cooled to 5° C. was further added to the crystal, and the obtained mixture was filtrated. The thus obtained crystal was removed from the filter paper, and was then dried at 40° C., at a degree of pressure reduction of 1 hPa for 45 hours, so as to obtain 23.1 g of white powders.

[0135] The obtained powders were analyzed by .sup.1H-NMR. As a result, peaks derived from diphenyldiphenoxy silane and 1,3-diphenoxy-1,1,3,3-tetraphenyldisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,3-diphenoxy-1,1,3,3-tetraphenyldisiloxane was obtained from the peak area ratio, and as a result, it was 99.6:0.4.

[0136] The yield of the molar amount of diphenyldiphenoxy silane, which was obtained from the weight of the obtained white powders and the above-described molar ratio, was 83.1%, with respect to the molar amount of silicon atoms contained in the octaphenylcyclotetrasiloxane.

Example 8

[0137] Dimethylpolysiloxane represented by the following formula (6) (with a hydroxy terminal treatment; molecular weight: 4,200) (7.4 g; 1.8 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (65 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 220° C. for 30 minutes.

##STR00012##

[0138] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a proton peak based on the dimethylpolysiloxane was not observed, and the conversion percentage of the dimethylpolysiloxane was confirmed to be 100%.

[0139] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 95.0:5.0.

Example 9

[0140] Dimethylpolysiloxane represented by the following formula (7) (manufactured by Shin-Etsu Chemical Co., Ltd.; KF-96-3000cs; trimethylsiloxy terminus; molecular weight: 40,000) (7.4 g; 0.19 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

##STR00013##

[0141] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a proton peak based on the dimethylpolysiloxane was not observed, and the conversion percentage of the dimethylpolysiloxane was confirmed to be 100%.

[0142] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 98.1:1.9.

Example 10

[0143] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), dibutyl carbonate (17.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0144] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.070 ppm based on dimethyldibutoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 69%.

Example 11

[0145] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 150° C. for 60 minutes.

[0146] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.378 ppm based on dimethyldiphenoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 71%.

[0147] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 78.7:21.3.

Example 12

[0148] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (65 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 220° C. for 30 minutes.

[0149] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was confirmed to be 100%.

[0150] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 99.6:0.4.

Example 13

[0151] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and potassium carbonate used as a catalyst (28 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 220° C. for 30 minutes.

[0152] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was 100%.

[0153] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the peak area ratio, and as a result, it was 99.7:0.3.

Example 14

[0154] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and sodium carbonate used as a catalyst (21 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 220° C. for 30 minutes.

[0155] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.378 ppm based on dimethyldiphenoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 89%.

[0156] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 94.3:5.7.

Example 15

[0157] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and sodium hydrogen carbonate used as a catalyst (17 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 220° C. for 30 minutes.

[0158] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.378 ppm based on dimethyldiphenoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 87%.

[0159] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 97.4:2.6.

Example 16

[0160] Hexamethylcyclotrisiloxane represented by the following formula (8) (7.4 g; 33.3 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (65 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 220° C. for 30 minutes.

##STR00014##

[0161] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the hexamethylcyclotrisiloxane was not observed, and the conversion percentage of the hexamethylcyclotrisiloxane was 100%.

[0162] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 99.3:0.7.

Example 17

[0163] Octamethylcyclotetrasiloxane represented by the following formula (9) (7.4 g; 25.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (65 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 220° C. for 30 minutes.

##STR00015##

[0164] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the octamethylcyclotetrasiloxane was not observed, and the conversion percentage of the octamethylcyclotetrasiloxane was 100%.

[0165] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 99.4:0.6.

Example 18

[0166] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium hydroxide used as a catalyst (75 mg; 0.5 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0167] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was 100%.

[0168] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 98.2:1.8.

Example 19

[0169] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and potassium hydroxide used a catalyst (11 mg; 0.2 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0170] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the decamethylcyclopentasiloxane was not observed, and the conversion percentage of the decamethylcyclopentasiloxane was 100%.

[0171] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were merely observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 97.6:2.4.

Example 20

[0172] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and sodium hydroxide used as a catalyst (12 mg; 0.3 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0173] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.378 ppm based on dimethyldiphenoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 66%.

[0174] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 94.4:5.6.

Example 21

[0175] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 120° C. for 60 minutes.

[0176] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.378 ppm based on dimethyldiphenoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 67%.

[0177] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 82.0:18.0.

Example 22

[0178] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 90° C. for 60 minutes.

[0179] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.378 ppm based on dimethyldiphenoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 2%.

[0180] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 33.3:66.7.

[0181] (Example 23) 1,3,5,7,9,11,13,15-Octamethylpentacyclo[9.5.1.1.sup.3,9.1.sup.5,15.1.sup.7,13]octasiloxane (2.06 g; 3.83 mmol; Si molar amount: 30.7 mmol), diphenyl carbonate (9.85 g; 46.0 mmol), and cesium carbonate used as a catalyst (15 mg; 0.05 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 180° C. for 150 minutes.

[0182] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a methyl proton peak on silicon that was based on the 1,3,5,7,9,11,13,15-octamethylpentacyclo [9.5.1.1.sup.3,9.1.sup.5,15.1.sup.7,13]octasiloxane was not observed, and the conversion percentage of the 1,3,5,7,9,11,13,15-octamethylpentacyclo[9.5.1.1.sup.3,9.1.sup.5,15.1.sup.7,13]octasiloxane was 100%.

[0183] As methyl proton peaks on silicon, a peak of 0.483 ppm based on methyltriphenoxy silane and a peak of 0.289 ppm based on 1,3-dimethyl-1,1,3,3-tetraphenoxydisiloxane were merely observed. The molar ratio between methyltriphenoxy silane and 1,3-dimethyl-1,1,3,3-tetraphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 93.7:6.3.

[0184] The chemical formulae of triaryloxy silane compounds and the like as products are shown below. The following formula (10) shows methyltriphenoxy silane, and the following formula (11) shows 1,3-dimethyl-1,1,3,3-tetraphenoxydisiloxane.

##STR00016##

Example 24

[0185] 1,3,5,7,9,11,13,15-Octaphenylpentacyclo[9.5.1.1.sup.3,9.1.sup.5,15.1.sup.7,13]octasiloxane (3.96 g; 3.83 mmol; Si molar amount: 30.6 mmol), diphenyl carbonate (9.85 g; 46.0 mmol), and cesium carbonate used as a catalyst (15 mg; 0.05 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 180° C. for 150 minutes.

[0186] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, a proton peak at a para position of the 1,3,5,7,9,11,13,15-octaphenylpentacyclo[9.5.1.1.sup.3,9.1.sup.5,15.1.sup.7,13]octasiloxane was not observed, and the conversion percentage of the 1,3,5,7,9,11,13,15-octaphenylpentacyclo[9.5.1.1.sup.3,9.1.sup.5,15.1.sup.7,13]octasiloxane was confirmed to be 100%.

[0187] To the reaction mixture that had been cooled to room temperature and had been then solidified, 10 g of heptane was added, and the obtained mixture was heated to 90° C., followed by hot filtration. The obtained filtrate was left at room temperature for 3 days, so that a white crystal was precipitated. Thereafter, 5 g of heptane cooled to 5° C. was further added to the crystal, and the obtained mixture was filtrated. The thus obtained crystal was removed from the filter paper, and was then dried at 40° C., at a degree of pressure reduction of 1 hPa for 45 hours, so as to obtain 9.42 g of white powders.

[0188] The obtained powders were analyzed by .sup.1H-NMR. As a result, peaks derived from phenyltriphenoxy silane and 1,3-diphenyl-1,1,3,3-tetraphenoxydisiloxane were observed. The molar ratio between phenyltriphenoxy silane and 1,3-diphenoxy-1,1,3,3-tetraphenyldisiloxane was obtained from the peak area ratio, and as a result, it was 96.0:4.0.

[0189] The yield of the molar amount of phenyltriphenoxy silane, which was obtained from the weight of the obtained white powders and the above-described molar ratio, was 76.8%, with respect to the molar amount of silicon atoms contained in the octaphenylcyclotetrasiloxane.

[0190] The chemical formulae of triaryloxy silane compounds and the like as products are shown below. The following formula (12) shows phenyltriphenoxy silane, and the following formula (13) shows 1,3-diphenyl-1,1,3,3-tetraphenoxydisiloxane.

##STR00017##

Example 25

[0191] A dropping funnel, a thermometer, and a cooling tube were equipped into a 500-ml four-neck flask. Thereafter, diphenyl carbonate (246.35 g; 1.15 mol), and cesium carbonate used as a catalyst (0.3748 g, 1.15 mmol) were added into the flask, and they were then heated to 180° C., without stirring. Diphenyl carbonate was dissolved around 100° C. After the temperature had reached 180° C., decamethylcyclopentasiloxane (85.30 g; 0.23 mol) was added dropwise to the reaction mixture at a dropping speed of 1 ml/min over 90 minutes. Immediately after initiation of the dropwise addition of the decamethylcyclopentasiloxane, CO.sub.2 gas was generated. After completion of the dropwise addition of the decamethylcyclopentasiloxane, the temperature was increased to 200° C., and the reaction mixture was heated at 200° C. for 90 minutes. Thereafter, the heating was terminated, and the reaction was completed.

[0192] Subsequently, the reaction mixture was cooled to 40° C., and was then subjected to reduced-pressure distillation at a degree of pressure reduction of 4 hPa and at 150° C., so as to obtain 270 g of a colorless oily component similar to that of Example 1.

Comparative Example 1

[0193] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol), diphenyl carbonate (21.4 g; 100.0 mmol), and cesium carbonate used as a catalyst (33 mg; 0.1 mmol) were substituted in a nitrogen atmosphere, and were then stirred at room temperature for 60 minutes.

[0194] The obtained mixture was analyzed by .sup.1H-NMR. As a result, as a methyl proton peak on silicon, only a proton peak based on the decamethylcyclopentasiloxane was observed, and the conversion percentage of the decamethylcyclopentasiloxane was 0%.

Comparative Example 2

[0195] Decamethylcyclopentasiloxane (7.4 g; 20.0 mmol; Si molar amount: 100.0 mmol) and diphenyl carbonate (21.4 g; 100.0 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 200° C. for 60 minutes.

[0196] The obtained mixture was analyzed by .sup.1H-NMR. As a result, as a methyl proton peak on silicon, only a proton peak based on the decamethylcyclopentasiloxane was observed, and the conversion percentage of the decamethylcyclopentasiloxane was 0%.

Comparative Example 3

[0197] Decamethylcyclopentasiloxane (0.37 g; 1.0 mmol; Si molar amount: 5.0 mmol), phenol (0.94 g; 10.0 mmol), and cesium carbonate used as a catalyst (3.3 mg; 0.01 mmol) were substituted in a nitrogen atmosphere, and were then stirred at 175° C. for 90 minutes.

[0198] Thereafter, the reaction mixture was analyzed by .sup.1H-NMR. As a result, as methyl proton peaks on silicon, a peak of 0.055 ppm based on decamethylcyclopentasiloxane and a peak of 0.378 ppm based on dimethyldiphenoxy silane were observed. The conversion percentage of the decamethylcyclopentasiloxane calculated from the ratio of the two peak areas was 4%.

[0199] As methyl proton peaks on silicon, a peak of 0.378 ppm based on dimethyldiphenoxy silane and a peak of 0.222 ppm based on 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane were observed. The molar ratio between dimethyldiphenoxy silane and 1,1,3,3-tetramethyl-1,3-diphenoxydisiloxane was obtained from the ratio of the two peak areas, and as a result, it was 59.6:40.4.

[0200] The results of individual examples and comparative examples are shown in the following Table 2 and Table 3.

TABLE-US-00002 TABLE 2 Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 Ex. 6 Ex. 7 Components A) Siloxane Decamethylcyclo- mmol 101 100 100 100 compound pentasiloxane (Si mol amount) Octaphenylcyclo- mmol 75 75 75 tetrasiloxane (Si mol amount) Dimethylpoly- mmol siloxane (hydroxy (Si mol terminal treatment, amount) molecular weight: 4,200) Dimethylpoly- mmol siloxane (Si mol (trimethylsiloxy amount) terminus, molecular weight: 40,000) Hexamethylcyclo- mmol trisiloxane (Si mol amount) Octamethylcyclo- mmol tetrasiloxane (Si mol amount) B) Carbonate Diphenyl carbonate mmol 101 110 150 90 75 78.8 82.6 compound Dibutyl carbonate mmol Phenol mmol C) Basic compound catalyst — Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 X (molar amount of carbonate mmol 1.0 1.1 1.5 0.9 1.0 1.05 1.10 compound/Si molar amount of siloxane compound) Y (molar amount (mmol) of basic mmol/mol 1.0 1.0 1.0 1.0 1.3 1.3 1.3 compound catalyst/Si molar amount (mol) of siloxane compound) Reaction Reaction temperature ° C. 200 200 200 200 200 200 200 conditions/ Conversion percentage of siloxane % 100 100 100 100 100 100 100 Evaluation compound results Molar ratio % 98.6:1.4 99.8:0.2 98.8:1.2 93.2:6.8 95.4:4.6 99.5:0.5 99.6:0.4 (molar amount of product of interest:molar amount of by-product) Ex. 8 Ex. 9 Ex. 10 Ex. 11 Ex. 12 Ex. 13 Components A) Siloxane Decamethylcyclo- mmol 100 100 100 100 compound pentasiloxane (Si mol amount) Octaphenylcyclo- mmol tetrasiloxane (Si mol amount) Dimethylpoly- mmol 100 siloxane (hydroxy (Si mol terminal treatment, amount) molecular weight: 4,200) Dimethylpoly- mmol 100 siloxane (Si mol (trimethylsiloxy amount) terminus, molecular weight: 40,000) Hexamethylcyclo- mmol trisiloxane (Si mol amount) Octamethylcyclo- mmol tetrasiloxane (Si mol amount) B) Carbonate Diphenyl carbonate mmol 100 100 100 100 100 compound Dibutyl carbonate mmol 100 Phenol mmol C) Basic compound catalyst — Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 K.sub.2CO.sub.3 X (molar amount of carbonate mmol 1.0 1.0 1.0 1.0 1.0 1.0 compound/Si molar amount of siloxane compound) Y (molar amount (mmol) of basic mmol/mol 2.0 1.0 1.0 1.0 2.0 2.0 compound catalyst/Si molar amount (mol) of siloxane compound) Reaction Reaction temperature ° C. 220 200 200 150 220 220 conditions/ Conversion percentage of siloxane % 100 100 69 71 100 100 Evaluation compound results Molar ratio % 95.0:5.0 98.1:1.9 — 78.7:21.3 99.6:0.4 99.7:0.3 (molar amount of product of interest:molar amount of by-product)

TABLE-US-00003 TABLE 3 Ex. 14 Ex. 15 Ex. 16 Ex. 17 Ex. 18 Ex. 19 Ex. 20 Ex. 21 Components A) Siloxane Decamethylcyclo- mmol 100 100 100 100 100 100 compound pentasiloxane (Si mol amount) Octaphenylcyclo- mmol tetrasiloxane (Si mol amount) Dimethylpoly- mmol siloxane (hydroxy (Si mol terminal treatment, amount) molecular weight: 4,200) Dimethylpoly- mmol siloxane (Si mol (trimethylsiloxy amount) terminus, molecular weight: 40,000) Hexamethylcyclo- mmol 100 trisiloxane (Si mol amount) Octamethylcyclo- mmol 100 tetrasiloxane (Si mol amount) Octamethylpenta- mmol cyclooctasiloxane (Si mol amount) Octaphenylpenta- mmol cyclooctasiloxane (Si mol amount) Decamethylcyclo- mmol pentasiloxane (Si mol amount) B) Carbonate Diphenyl carbonate mmol 100 100 100 100 100 100 100 100 compound Dibutyl carbonate mmol Phenol mmol C) Basic compound catalyst — Na.sub.2CO.sub.3 NaHCO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 CsOH KOH NaOH Cs.sub.2CO.sub.3 X (molar amount of carbonate mol/mol 1.0 10 1.0 1.0 1.0 1.0 1.0 1.0 compound/Si molar amount of siloxane compound) Y (molar amount (mmol) of basic mmol/mol 2.0 2.0 2.0 2.0 5.0 2.0 3.0 1.0 compound catalyst/Si molar amount (mol) of siloxane compound) Reaction Reaction temperature ° C. 220 220 220 220 200 200 200 120 conditions/ Conversion percentage of siloxane % 89 87 100 100 100 100 66 67 Evaluation compound results Molar ratio % 94.3:5.7 97.4:2.6 99.3:0.7 99.4:0.6 98.2:1.8 97.6:2.4 94.4:5.6 82.0:18.0 (molar amount of product of interest:molar amount of by-product) Comp. Comp. Comp. Ex. 22 Ex. 23 Ex. 24 Ex. 25 Ex. 1 Ex. 2 Ex. 3 Components A) Siloxane Decamethylcyclo- mmol 100 100 100 5 compound pentasiloxane (Si mol amount) Octaphenylcyclo- mmol tetrasiloxane (Si mol amount) Dimethylpoly- mmol siloxane (hydroxy (Si mol terminal treatment, amount) molecular weight: 4,200) Dimethylpoly- mmol siloxane (Si mol (trimethylsiloxy amount) terminus, molecular weight: 40,000) Hexamethylcyclo- mmol trisiloxane (Si mol amount) Octamethylcyclo- mmol tetrasiloxane (Si mol amount) Octamethylpenta- mmol 3.83 cyclooctasiloxane (Si mol amount) Octaphenylpenta- mmol 3.83 cyclooctasiloxane (Si mol amount) Decamethylcyclo- mmol 230 pentasiloxane (Si mol amount) B) Carbonate Diphenyl carbonate mmol 100 46 46 1150 100 100 compound Dibutyl carbonate mmol Phenol mmol 10 C) Basic compound catalyst — Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 Cs.sub.2CO.sub.3 None Cs.sub.2CO.sub.3 X (molar amount of carbonate mol/mol 1.0 1.5 1.5 1.0 1.0 1.0 — compound/Si molar amount of siloxane compound) Y (molar amount (mmol) of basic mmol/mol 1.0 1.6 1.6 1.0 1.0 0.0 2.0 compound catalyst/Si molar amount (mol) of siloxane compound) Reaction Reaction temperature ° C. 90 180 180 200 Room 200 175 conditions/ temper- Evaluation ature results Conversion percentage of siloxane % 2 100 100 100 0 0 4 compound Molar ratio % 33.3:66.7 93.7:6.3 96.0:4.0 96.9:3.1 — — 59.6:40.4 (molar amount of product of interest:molar amount of by-product)