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Compound, synthetic method and application of organosilicon containing carbon-oxygen-ether linkage

A technology of organosilicon compounds and carbon-containing oxyethers, applied in the directions of organic compounds/hydrides/coordination complex catalysts, organic chemistry, chemical instruments and methods, etc. Simple preparation and high reaction yield

Inactive Publication Date: 2006-02-01
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

〖(a) E.W.Hagaman, H.Zhu, S.H.Overbury, S.Dai, Langmir, 2004, 20, 9577.〗Although the literature 〖(a)M.E.Havill, I.Joffe, H.W.Post, J.Org.Chem.1948 , 2, 282. (b) A.Behr, F.Naendrup, D.Obst, Adv.Synth.Catal, 2002, 344, 1142〗 has been reported to use chloroplatinic acid as catalyst to generate organic Silicon compounds, however, this new type of carbon-oxygen bonded silicone has not been reported

Method used

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  • Compound, synthetic method and application of organosilicon containing carbon-oxygen-ether linkage
  • Compound, synthetic method and application of organosilicon containing carbon-oxygen-ether linkage
  • Compound, synthetic method and application of organosilicon containing carbon-oxygen-ether linkage

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Experimental program
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Embodiment 1

[0025] (1) Preparation of organosilicon compound 1:

[0026]

[0027] The operation is as follows: chloroplatinic acid (0.5mol%) was vacuum-dried at 180°C for 2 hours, added ethyl-allyl-tetraethylene glycol ether (0.1mol), triethoxysilyl hydrogen (0.3mol), and stirred at room temperature 1 day. Excess triethoxysilane was distilled off, the vacuum pump depressurized, and the colorless liquid was distilled off at 178°C to obtain 27.5 g of the product. 1 H NMR (300MHz, CDCl 3 ): δ3.79(q, J=7.2Hz, 6H), 3.64-3.43(m, 18H), 3.39(t, J=6.9Hz, 2H), 1.71-1.61(m, 2H), 1.19-1.14( m, 12H), 0.59 (t, J=8.4Hz, 2H). 13 C NMR (75MHz, CDCl 3 ): δ73.4, 70.9, 70.6, 70.1, 63.0, 51.3, 17.9, 15.5, 14.7, 8.0; MS m / z (%) 337 (100), 427 (M + , 35.45); Elemental analysis calculated value, C 19 h 42 o 8 Si: C, 53.49; H, 9.92; Found: C, 53.65; H, 9.70.

Embodiment 2

[0029] (2) Preparation of organosilicon compound 2:

[0030]

[0031] The operation is as follows: the operation is as follows: chloroplatinic acid (0.5mol%) was vacuum-dried at 180° C. for 2 hours, added methyl-allyl-tetraethylene glycol ether (0.1mol), triethoxysilyl hydrogen (0.3mol) , stirred at room temperature for 1 day. Excess triethoxysilane was distilled off, the vacuum pump depressurized, and the colorless liquid was distilled off at 178°C to obtain 27.3 g of the product. 1 H NMR (300MHz, CDCl 3 ): δ3.78(q, J=7.2Hz, 6H), 3.64-3.43(m, 18H), 3.39(t, J=6.9Hz, 2H), 3.25(t, J=8.4Hz, 3H), 1.71 -1.61 (m, 2H), 1.23 (t, J=8.2Hz, 9H), 0.59 (t, J=8.4Hz, 2H). 13 C NMR (75MHz, CDCl 3 ): δ70.9, 70.6, 70.1, 63.0, 53.9, 51.3, 17.9, 15.5, 8.0; MS m / z (%) 323 (100), 413 (M + , 22.23); Elemental analysis calculated value, C 18 h 40 o 8 Si: C, 52.40; H, 9.77; Found: C, 52.62; H, 9.65.

Embodiment 3

[0033] (3) Preparation of organosilicon compound 3:

[0034]

[0035] The operation is as follows: chloroplatinic acid (0.5mol%) was vacuum-dried at 180°C for 2 hours, added phenyl-allyl-tetraethylene glycol ether (0.1mol), triethoxysilyl hydrogen (0.3mol), and stirred at room temperature 1 day. Excess triethoxysilane was distilled off, the vacuum pump depressurized, and the colorless liquid was distilled off at 178°C to obtain 32.8g of the product. 1 H NMR (300MHz, CDCl 3 ): δ6.90-6.76(m, 5H), 4.20(t, J=6.9Hz, 2H), 3.79(q, J=7.2Hz, 6H), 3.64-3.43(m, 16H), 1.70-1.64( m, 2H), 1.19-1.14 ((t, J = 7.2Hz, 9H), 0.69 (t, J = 8.4Hz, 2H). 13 C NMR (75MHz, CDCl 3 ): δ158.8, 129.1, 120.1, 114.2, 73.4, 70.9, 70.6, 70.5, 51.3, 17.9, 15.5, 14.7, 8.0; MS m / z (%) 385 (100), 475 (M + , 22.54); Elemental analysis calculated value, C 23 h 42 o 8 Si: C, 58.20; H, 8.92; Found: C, 58.45; H, 8.70.

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Abstract

An organosilicon compound containing carbonyloxyether bond is disclosed, which can be used to synthesize the organosilicon material containing carbonyloxyether bond and to modify the surface of meso-porous Si material. Its preparing process is also disclosed.

Description

technical field [0001] The invention relates to a new type of organosilicon compound containing a carbon oxygen ether bond, a synthesis method and an application thereof. The synthesis method of this kind of compound is to generate organosilicon compound through hydrosilation reaction of olefin. Silicones containing different numbers and types of carbon-oxygen ether bonds can be synthesized through different olefin substrates; or re-grafted onto the surface of silicon materials, thereby changing the properties of silicon materials. The modified silicon material can be used as a loaded catalyst for synthesizing precious metal catalysts. The modified silicon material is also potentially used in the adsorption of metals, the adjustment of the hydrophilic and hydrophobic surfaces of the material, and the phase transfer catalysis, which provides broad prospects for its industrial production. Background technique [0002] Since the MCM-4 mesoporous silicon material first reporte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C01B33/12B01J31/02B01J21/08
Inventor 麻生明杨青肖丰收
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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