A kind of Schiff base magnesium organic metal compound and its preparation method and application

A technology for metal compounds and Schiff base magnesium, which is applied in the field of metal organic compound preparation, can solve the problems of the synthesis and application of sodium magnesium bimetallic compounds without Schiff base magnesium, and achieves simple and easy operation, high yield, The effect of product purification

Inactive Publication Date: 2017-12-12
南京芬纽克新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the prior art, there is no application of Schiff base magnesium metal compounds and the synthesis and application of sodium-magnesium bimetals

Method used

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  • A kind of Schiff base magnesium organic metal compound and its preparation method and application
  • A kind of Schiff base magnesium organic metal compound and its preparation method and application
  • A kind of Schiff base magnesium organic metal compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base ligand is as follows:

[0037] 10.04mmol of 2,4,6-tri-tert-butylaniline, 10.04mmol of 3,5-di-tert-butyl salicylaldehyde, 1.67mmol of p-toluenesulfonic acid and 100mL of ethanol were added to a 100mL round-bottom flask, and the reaction was refluxed for 48h. A large number of light yellow crystals precipitated at -30°C, filtered, the mass was 4.32g, which was 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base, the yield was 90% . M.p.178-180°C.

[0038] NMR spectrum: 1 H NMR (600MHz, 298K, C 6 D. 6 ): δ1.26(s, 9H, C(CH 3 ) 3 ), 1.38(s, 9H, C(CH 3 ) 3 ), 1.39(s, 18H, C(CH 3 ) 3 ), 1.65(s, 9H, C(CH 3 ) 3 ), 7.03 (d, J H-H =2.4Hz, 1H, Ar-H), 7.56(s, 2H, Ar-H), 7.63(d, J H-H =2.4Hz, 1H, Ar-H), 7.92(s, 1H, CH=N), 14.14(s, 1H, OH) ppm. 13 C{ 1 H}NMR (151MHz, C 6 D. 6 ): δ29.8, 31.6, 31.8, 32.4, 34.3, 35.0, 35.5, 36.1, 118.1, 122.2, 126.8, 128.4, 128.6, 137.8, 140.9, 141.0, 146.0, 148...

Embodiment 2

[0040] The preparation of 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base ligand is as follows:

[0041] 10.0mmol of 2,4,6-tri-tert-butylaniline, 10.0mmol of 3,5-di-tert-butyl salicylaldehyde, 2.5mmol of p-toluenesulfonic acid and 100mL of ethanol were added to a 100mL round-bottomed flask, and the reaction was refluxed for 24h. A large number of light yellow crystals were precipitated at -10°C. After filtration, the mass was 4.2 g, which was 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base, and the yield was 89%. . M.p.178-180°C.

[0042] NMR spectrum: 1 H NMR (600MHz, 298K, C 6 D. 6 ): δ1.26(s, 9H, C(CH 3 ) 3 ), 1.38(s, 9H, C(CH 3 ) 3 ), 1.39(s, 18H, C(CH 3 ) 3 ), 1.65(s, 9H, C(CH 3 ) 3 ), 7.03 (d, J H-H =2.4Hz, 1H, Ar-H), 7.56(s, 2H, Ar-H), 7.63(d, J H-H =2.4Hz, 1H, Ar-H), 7.92(s, 1H, CH=N), 14.14(s, 1H, OH) ppm. 13 C{ 1 H}NMR (151MHz, C 6 D. 6 ): δ29.8, 31.6, 31.8, 32.4, 34.3, 35.0, 35.5, 36.1, 118.1, 122.2, 126.8, 128.4, 128.6, 137.8, 140.9, ...

Embodiment 3

[0044] The preparation of 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base ligand is as follows:

[0045] Add 9.0mmol of 2,4,6-tri-tert-butylaniline, 9.0mmol of 3,5-di-tert-butyl salicylaldehyde, 3mmol of p-toluenesulfonic acid and 100mL of ethanol into a 100mL round-bottomed flask, and react under reflux for 12h. A large number of light yellow crystals were precipitated at 4°C. After filtration, the mass was 3.86 g, which was 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base, and the yield was 90%. M.p.178-180°C.

[0046] NMR spectrum: 1 H NMR (600MHz, 298K, C 6 D. 6 ): δ1.26(s, 9H, C(CH 3 ) 3 ), 1.38(s, 9H, C(CH 3 ) 3 ), 1.39(s, 18H, C(CH 3 ) 3 ), 1.65(s, 9H, C(CH 3 ) 3 ), 7.03 (d, J H-H =2.4Hz, 1H, Ar-H), 7.56(s, 2H, Ar-H), 7.63(d, J H-H =2.4Hz, 1H, Ar-H), 7.92(s, 1H, CH=N), 14.14(s, 1H, OH) ppm. 13 C{ 1 H}NMR (151MHz, C 6 D. 6 ): δ29.8, 31.6, 31.8, 32.4, 34.3, 35.0, 35.5, 36.1, 118.1, 122.2, 126.8, 128.4, 128.6, 137.8, 140.9, 141.0, 146.0, 148.5,...

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Abstract

The invention discloses a Schiff base magnesium organometallic compound, and a preparation method and an application thereof. The preparation method comprises the following steps: 1, heating and refluxing 2,4,6-tri-tert-butylaniline, 3,5-di-tert-butylsalicylaldehyde and p-toluenesulfonic acid in ethanol until reaction is completed to precipitate a large amount of pale yellow crystals which are 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base; 2, respectively reacting the 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base and 2-(2,6-di(diphenylmethyl)-4-isopropyl)-3,5-di-tert-butyl Schiff base with methylmagnesium iodide under waterless anoxic conditions to obtain a large amount of colorless crystals which are 2-(2,4,6-tri-tert-butyl)-3,5-di-tert-butyl Schiff base magnesium metal compound and 2-(2,6-di(diphenylmethyl)-4-isopropyl)-3,5-di-tert-butyl Schiff base magnesium iodide respectively; and 3, reacting the 2-(2,6-di(diphenylmethyl)-4-isopropyl)-3,5-di-tert-butyl Schiff base magnesium iodide with metallic sodium to obtain pale yellow crystals which are 2-(2,6-di(diphenylmethyl)-4-isopropyl)-3,5-di-tert-butyl sodium magnesium bi-metal compound.

Description

technical field [0001] The invention relates to the technical field of metal-organic compound preparation, in particular to a Schiff base magnesium metal-organic compound and its preparation and application. Background technique [0002] Hydrosilylation is a reaction in which silicon hydrides are added to unsaturated organic compounds to form various organosilicon compounds. In 1947, Leo Sommer et al. reported the first hydrosilation reaction, namely the reaction of trichlorosilane and 1-octene in acetyl peroxide [L.Sommer, E.Pietrusza, F.Whitmore, J.Am.Chem .Soc.1947,69,188]. The catalytic reduction of ketones to secondary alcohols is one of the most fundamental reactions in organic chemistry. Hydrosilation is one of the most important and effective methods for reducing C=O bonds [K.Revunova, G.I.Nikonov, Chem.Eur.J.2014, 20, 839-845; H.Zhao, H.Sun, X.Li, Organometallics 2014, 33, 3535-3539; X. Ren, H. Du, J. Am. Chem. Soc. 2016, 138, 810-813]. The hydrosilylation produ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/24C07C249/02B01J31/22C07F19/00C07F7/04C07C33/22C07C33/20C07C33/24C07C27/02C07C41/26C07C43/23C07C213/00C07C215/68
Inventor 马猛涛王未凡秦奕沈兴超李佳姚薇薇朱丽珺
Owner 南京芬纽克新材料有限公司
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