Method of preparing functional organosilanol compounds

Patent metadata

Field	Value
Publication number	US-12227530-B2
Application number	US-201917418960-A
Country	US
Kind code	B2
Filing date	Dec 20, 2019
Priority date	Dec 31, 2018
Publication date	Feb 18, 2025
Grant date	Feb 18, 2025

Abstract

A method of preparing an organosilanol compound is disclosed. The method comprises reacting (A) an initial organosilicon compound and (B) water in the presence of (C) a catalyst. The catalyst (C) is selected from: (C1) [(C 8 H 12 irCl] 2 [(p-cymene)RuCl 2 ] 2 ; and (C3) Pd/C. The initial organosilicon compound (A) has the general formula HO—Si(R) 2 —[Si(R) 2 O] a —OSi(R) 2 —Y and the organosilanol compound has the general formula HO—Si(R)2-[Si(R) 2 O] a —OSi(R) 2 —Y, where each R is an independently selected hydrocarbyl group; Y comprises a functional moiety selected from alkoxysilyl moieties, epoxide moieties, and acryloxy moieties, with the proviso that Y is other than the acryloxy moieties when the catalyst (C) is (C3) Pd/C; and subscript a is 0 or 1. The organosilanol compound prepared by the method is also provided.

First claim

The invention claimed is:

1. A method of preparing an organosilanol compound, said method comprising:
reacting (A) an initial organosilicon compound and (B) water in the presence of (C) a catalyst selected from (C1) [(C 8 H 12 )IrCl] 2 , (C2) [(p-cymene) RuCl 2 ] 2 , and (C3) Pd/C, thereby preparing the organosilanol compound;
wherein the initial organosilicon compound (A) has the general formula:

and the organosilanol compound has the general formula:

where each R is an independently selected hydrocarbyl group; Y comprises a functional moiety selected from alkoxysilyl moieties, epoxide moieties, and acryloxy moieties, with the proviso that Y is other than the acryloxy moieties when the catalyst (C) is (C3) Pd/C; and subscript a is 0 or 1.

2. The method of claim 1 , wherein each Y is independently of formula-D-R 1 , where D is a divalent linking group and R 1 comprises an alkoxysilyl group, an acryloxy group, or an epoxide group.

3. The method of claim 2 , wherein R 1 is an alkoxysilyl group of the formula:

where each R 2 is an independently selected hydrocarbyl group; and subscript c is 0, 1, or 2.

4. The method of claim 3 , wherein: (i) each R 2 is independently selected from —CH 3 and —CH 2 CH 3 ; (ii) subscript c is 0; or (iii) both (i) and (ii).

5. The method of claim 2 , wherein R 1 is an epoxide group having one of formulas (I) and (II):

6. The method of claim 2 , wherein R 1 is an acryloxy group of the formula:

where R 3 independently selected from hydrocarbyl groups and H.

7. The method of claim 6 , wherein R 3 is H or —CH 3 .

8. The method of claim 2 , wherein: (i) divalent linking group D comprises a hydrocarbon group of formula —(CH 2 ) m —, where subscript m is from 1 to 6; (ii) divalent linking group D comprises an ether moiety; or (iii) both (i) and (ii).

9. The method of claim 1 , wherein: (i) each R is —CH 3 ; (ii) subscript a is 0; or (iii) both (i) and (ii).

10. The method of claim 1 , wherein reacting the initial organosilicon compound (A) and water (B): (i) forms a reaction product comprising the organosilanol compound, and wherein the method further comprises isolating the organosilanol compound from the reaction product; (ii) is performed in the presence of (D) a reaction inhibitor; or (iii) both (i) and (ii).

Assignees

• Dow Silicones Corp
• Dow Global Techologies LLC
• Dow Global Technologies Llc

Inventors

• Eldred Donald V
• Jeletic Matthew
• Roberts John
• Yvon-Bessette Andre

Classifications

• C07F7/0874

  Reactions involving a bond of the Si-O-Si linkage · CPC title

• B01J2531/827

  Iridium · CPC title

• B01J2531/821

  Ruthenium · CPC title

• B01J31/2295

  Cyclic compounds, e.g. cyclopentadienyls · CPC title

• B01J27/20

  Carbon compounds · CPC title