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Method of preparing functional organosilanol compounds
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A technology for organosilicon compounds and silanols, which is applied in the field of preparing organosilanol compounds and organosilanol compounds, and can solve the problems of limited general applicability, reduced yield and purity, and difficult functional organosilicon compounds.
Pending Publication Date: 2021-08-13
DOW SILICONES CORP +1
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However, many methods for preparing hybrid materials require functional organosilicon compounds that are often difficult to synthesize and / or utilize
In particular, conventional methods for preparing certain functional organosilicon compounds are often incompatible with many organosilicon materials (e.g., by promoting organosilicon rearrangements, non-selective reactions, degradation, hydrolysis of functional groups, etc.), resulting in reduced yields and purity , and limit the general applicability of these methods to
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example 1
[0091] Example 1: IrCODCl dimer catalyzed hydrolysis of AMA conversion agent
[0092]
[0093] To a 100 mL flask was added 5.0098 g of AMA converting agent, 10 mL of THF and 100 μL of Ir(COD)Cl dimer (0.025M in toluene). The solution was stirred, then 400 μL of DI water (1.15 equiv) was added at room temperature. The reaction was mildly exothermic with vigorous bubbling (H 2 freed). The reaction was stirred for 15 minutes, then most of the THF was stripped. 1 H NMR showed about 4% reduced (minor) product. The material was then distilled at 74 mTorr and 65°C. 4.5 g (85%) were recovered with a purity of 95%. 1 H (400MHz, Benzene-d 6 ): Main δ6.15(m,1H,CCH 2 ), 5.22 (p, J=1, 1H, CCH 2 ), 4.08(t, J=8Hz, 2H, OCH 2 ), 3.17 (br s, 1H, OH), 1.84 (dd, J=1Hz, J=1Hz, 3H, CCH 3 ),1.66(m,2H,OCH 2 CH 2 ),0.49(m,2H,SiCH 2 ),0.14(s,6H,SiCH 3 ),0.10(s,6H,SiCH 3 ). Secondary δ4.04(t, J=8Hz, 2H, OCH 2 ), 3.17 (br s, 1H, OH), 2.39 (sept, J=8Hz, 1H, CH), 1.66 (m, 2H, OCH 2 CH ...
example 2
[0094] Example 2: Ir-catalyzed hydrolysis of ETM converters
[0095]
[0096] To a 40 mL scintillation vial was added 2.0078 g of ETM converter, 4 mL of THF and 40 μL of Ir(COD)Cl dimer (0.025M in toluene). The solution was stirred, then 400 μL of DI water (3.15 equiv) was added at room temperature. The reaction was stirred for 15 minutes, then most of the THF was stripped. GCMS indicated product was present at 85%.
example 3
[0097] Example 3: Pd-Catalyzed ETM Converter Hydrolysis
[0098]
[0099]To a 100 mL flask was added 10.00 g of ETM converter, 12 mL of THF and 50 mg of Pd / C (10%). The solution was stirred, then 700 μL of DI water (1.10 equiv) was added at room temperature. The reaction was stirred for 20 minutes, then most of the Pd / C was filtered off. The product was then distilled at 74 mTorr and 50 °C to provide the main product in 90% yield. 1 H (400MHz, Benzene-d 6 ):δ3.47(m,9H,OCH 3 ),0.77(s,4H,SiCH 2 CH 2 ),0.16(s,6H,SiCH 3 ),0.15(s,6H,SiCH 3 ). 29 Si: Main δ8.2(M R ),-12.5(M OH ),-41.8(Si(OMe) 3 ). Minor δ8.7(M R ),-11.1(Si(Me) 2 OMe), -42.1 (Si(OMe) 2 OH).
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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) [(C8H12irCI]2 [(p-cymene)RuCl2]2; and (C3) Pd / C. The initial organosilicon compound (A) has the general formula HO-Si(R)2- [Si(R)2O]a-OSi(R)2-Y and the organosilanol compound has the general formula HO-Si(R)2- [Si(R)2O]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.
Description
[0001] Cross References to Related Applications [0002] This application claims priority and all advantages of U.S. Provisional Patent Application No. 62 / 786,885, filed December 31, 2018, the contents of which are hereby incorporated by reference. technical field [0003] The present invention relates generally to organosilicon compounds, and more particularly to methods of preparing organosilanol compounds and organosilanol compounds prepared thereby. Background technique [0004] Silicone materials are known in the art and are used in a variety of end use applications and environments. For example, the organopolysiloxanes thus prepared are used in many industrial, home care and personal care formulations. Hybrid materials with silicone and organofunctionality are increasingly used in such formulations because such hybrid materials can exhibit combined benefits traditionally only associated with silicone or organic materials. However, many methods of preparing hybrid ma...
Claims
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