Method for producing silane compound

Patent metadata

Field	Value
Publication number	US-12344628-B2
Application number	US-202017439954-A
Country	US
Kind code	B2
Filing date	Mar 19, 2020
Priority date	Mar 22, 2019
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

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 1 to R 5 , X, n, m and pare as described in the description of the present application.)

First claim

The invention claimed is:

1. A method for producing a silane compound, comprising 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) siloxane decomposition by 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 comprising a diaryl carbonate, dialkyl carbonate, or a monoalkylmonoaryl carbonate, and
C) a basic compound catalyst,
so as to alkoxylate and/or aryloxylate A) the siloxane compound(s):

wherein R 1 and R 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,

wherein R 3 and R 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 5 SiO 1.5 ]p  (3)

wherein R 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,
wherein B) the carbonate compound comprises at least diphenyl carbonate, and
wherein C) the basic compound catalyst comprises at least an alkali metal carbonate.

2. A method for producing a silane compound comprising 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, or a monoalkylmonoaryl carbonate, and
C) a basic compound catalyst,
so as to alkoxylate and/or aryloxylate A) the siloxane compound(s):

wherein R 1 and R 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

wherein R 3 and R 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,
wherein B) the carbonate compound comprises at least diphenyl carbonate, and
wherein C) the basic compound catalyst comprises at least an alkali metal carbonate.

3. The method for producing a silane compound according to claim 1 , wherein the R 1 to R 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 1 to R 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 further comprises an alkali metal hydroxide.

8. The method for producing a silane compound according to claim 1 , wherein C) the basic compound catalyst comprises cesium carbonate or potassium carbonate.

9. The method for producing a silane compound according to claim 1 , wherein, in D) the siloxane decomposition, 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, 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, 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, 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, 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 comprises E) distillation/recrystallization that comprises distilling the silane compound generated by D) the siloxane decomposition or recrystallization by recrystallizing the silane compound generated by D) the siloxane decomposition.

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

17. The method for producing a silane compound according to claim 1 , which further comprises F) a dropping by adding A) the siloxane compound dropwise to a mixture comprising B) the carbonate compo

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Uera Kazuyoshi
• Itoh Syouichi
• Kamatani Kohei

Classifications

• C07F7/0838

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C07F7/188 Primary

  by reactions involving the formation of Si-O linkages · CPC title

• C07F7/1804 Primary

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title