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Alkoxyl compound of beta-ketone di-imidogen zincium, preparation and application thereof

A ketodiimide zinc and alkoxy compound technology is applied in the field of element organic compound synthesis and catalysis, can solve the problems of difficult preparation and high synthesis cost, and achieves the effects of simple preparation method, high catalytic activity and high yield

Inactive Publication Date: 2008-07-16
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This problem can be overcome by alcoholysis with amino compounds of β-ketodiiminozinc (Chamberlain, B.M.; Cheng, M.; Moore, D.R.; Ovitt, T.M.; Lobkovsky, E.B.; Coates, G.W.J.Am.Chem.Soc. 2001, 123, 3229-3238; Dove, AndrewP.; Gibson, Vernon C.; Marshall, Edward L.; White, Andrew J.P.; Williams, David J.J.Chem.Soc., Dalton Trans.2004, 570-578), but The cost of precursor synthesis is high, and some alkoxyzinc compounds with large steric hindrance are difficult to prepare due to steric hindrance

Method used

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  • Alkoxyl compound of beta-ketone di-imidogen zincium, preparation and application thereof
  • Alkoxyl compound of beta-ketone di-imidogen zincium, preparation and application thereof
  • Alkoxyl compound of beta-ketone di-imidogen zincium, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1) Preparation of β-ketodiimine II: Take 100g of 2,6-dimethylaniline (>99%), 41.3g of 2,4-pentanedione, and 35mL of concentrated hydrochloric acid into a 500mL three-necked flask, add methanol to dissolve and reflux After 48 hours, filter, add NaOH solution to the obtained filtrate to adjust the pH>7.2, then use CH 2 Cl 2 (50mL×3) extraction, the organic phases were combined and dried with anhydrous magnesium sulfate to remove CH 2 Cl 2 The obtained solid was recrystallized from n-hexane to obtain 66.0 g of colorless massive crystal II with a yield of 53%. mp 77-79°C.

[0029] 2) Preparation of the ethyl compound III of β-ketodiimine zinc: take 6.13g (20mmol) of β-ketodiimine compound II into a 100mL Schlenk bottle, and vacuumize the oil pump for 1 hour. Add 40mL of toluene to dissolve the compound, add 30mmol ZnEt 2 The toluene solution was stirred at room temperature for 1 hour, heated to reflux and continued to react for 3 hours, the volatile substances were rem...

Embodiment 2

[0034] β-ketodiimino zinc alkoxylate I b Preparation: Add 0.37g (0.50mmol) of the β-ketodiimino zinc hydrogen bridge compound V obtained in step 4) of Example 1 to a 100mL Schlenk bottle, dissolve it in 20mL of toluene, and add equimolar Benzaldehyde toluene solution 2M (0.50mL, 1.0mmol), after 4 hours of reaction, a white precipitate was obtained, which crystallized at room temperature after heating and dissolving to obtain 0.38g of β-ketodiiminozinc alkoxy compound I b , yield 80%. 1 H NMR (C 6 D. 6 , 400MHz): 7.31 [d, 4H, CH 2 C 6 h 5 (m-H)], d 7.13 (m, 12H, ArH), 7.12 [m, 4H, CH 2 C 6 h 5 (p-H)], 7.07 [s, ​​4H, CH 2 C 6 h 5 (o-H)], 4.92 (s, 2H, γ-CH), 4.85 [s, 4H, Zn-(μ-OCH 2 C 6 h 5 )], 1.96(s, 24H, Ar-CH 3 ), 1.50(s, 12H, β-CCH 3 ).

Embodiment 3

[0036] β-ketodiimino zinc alkoxylate I b Preparation: Add 0.37 g (0.50 mmol) of the β-ketodiimino zinc hydrogen bridge compound V obtained in Step 4) of Example 1 to a 100 mL Schlenk bottle, dissolve it in 20 mL of toluene, add it at -75 ° C, etc. Mole of benzyl alcohol toluene solution 2M (0.50mL, 1.0mmol), the reaction temperature was gradually raised to room temperature and continued to react for 4h, a white precipitate was obtained, which crystallized at room temperature after heating and dissolving to obtain 0.32g β-ketodiiminozinc alkoxide base compound I b , yield 67%. 1 H NMR (C 6 D. 6 , 600MHz): 7.32 [d, 4H, CH 2 C 6 h 5 (m-H)], d 7.13 (m, 12H, ArH), 7.12 [m, 4H, CH 2 C 6 h 5 (p-H)], 7.07 [s, ​​4H, CH 2 C 6 h 5 (o-H)], 4.92 (s, 2H, γ-CH), 4.85 [s, 4H, Zn-(μ-OCH 2 C 6 h 5 )], 1.96(s, 24H, Ar-CH 3 ), 1.50(s, 12H, β-CCH 3 ).

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Abstract

The invention discloses an alkoxyl compound of beta-ketone di-imino zinc as well as preparation and application thereof, which belongs to the field of synthesis and catalysis technology of organic compounds of elements. The alkoxyl compound of the invention has the structure of general formula I, wherein R is (CH3)2CH, C6H5CH2 or C6H5; Ar is 2, 6-(CH3)2C6H3. The compound of the invention is prepared through reaction of hydrogen bridge compounds of beta-ketone di-imino zinc and an alcohol, an aldehyde or a ketone, wherein the alcohol has one to twenty carbon atoms and has preferable CH3OH, C6H5OH or C6H5CH2OH; the aldehyde and the ketone have one to twenty atoms, C6H5CHO and CH3COCH3 are preferably chosen. The alkoxyl compound of the invention can be used as the catalyst in ring-opening polymerization of ring-ester compounds or in alternating copolymerization of carbon dioxide and epoxy compounds. The invention has the advantages of simple preparation method, high yield and high catalytic activity.

Description

technical field [0001] The invention belongs to the technical field of elemental organic compound synthesis and catalysis, and specifically relates to a β-ketodiimine zinc alkoxy compound with good catalytic performance and its preparation and application. Background technique [0002] The alkoxy compounds of β-ketodiimine zinc have very good catalytic activity for the ring-opening polymerization of lactones and lactides and the alternating polymerization of epoxy compounds and carbon dioxide. In recent years, due to the wide application of biodegradable polymer materials in daily life, the alkoxy compounds of β-ketodiimine zinc have received more extensive attention. The alkoxy compound of β-ketodiimino zinc shows different catalytic activity and stereoselectivity (Cheng, M.; Moore, D. R.; Reczek, J. J.; Chamberlain, B. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. .Int.Ed.2002, 41, 2599-2601; Chamber-lain, B.M.; Cheng, M.; Moore, D.R.; Ovitt, T.M.; -3238). The synthesis o...

Claims

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Application Information

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IPC IPC(8): C07F3/06C08G63/83C08G63/08C08G63/00
Inventor 郝海军孙睿陈标华李英霞
Owner BEIJING UNIV OF CHEM TECH
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