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Cycloheptatriene-structure-containing aluminium compound catalysts, synthesis thereof and uses of the catalysts

A technology of cycloheptatriene and cycloheptatrienone is applied in the field of aluminum compound catalyst containing cycloheptatriene structure, synthesis and application thereof, and can solve the problems of limited application, low activity of aluminum-containing catalyst and the like

Inactive Publication Date: 2016-07-06
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, aluminum-containing catalysts still have the disadvantage of low activity, which limits their industrial application.

Method used

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  • Cycloheptatriene-structure-containing aluminium compound catalysts, synthesis thereof and uses of the catalysts
  • Cycloheptatriene-structure-containing aluminium compound catalysts, synthesis thereof and uses of the catalysts
  • Cycloheptatriene-structure-containing aluminium compound catalysts, synthesis thereof and uses of the catalysts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of 2-[2-(phenoxy)anilino]tropone

[0039]

[0040] Under nitrogen, add tris(dibenzylidene-BASE acetone)dipalladium (0.09 g, 0.01 mmol, purchased from Anaiji Company), 1,1'-binaphthyl-2, 2'-bisdiphenylphosphine (0.012 g, 2.0 mmol, purchased from Anaiji Company), 2-trifluoromethanesulfonate cycloheptatrienone (0.53 g, 2.0 mmol), 2-phenoxy Aniline (0.44 g, 2.4 mmol, purchased from Anaji) and 4 mL of toluene. The mixture was stirred at 80° C. for 24 hours, cooled down to room temperature after the reaction, filtered through a 10 cm silica gel column, and washed with 200 ml of dichloromethane. Finally, the eluent was passed through the column with petroleum ether:ethyl acetate=10:1 to obtain a yellow product (0.48 g, yield 83%). 1 HNMR (400MHz, CDCl 3 ):δ=8.75(s,1H,NH),7.52–7.47(m,1H,CH),7.29(d,J=7.3Hz,2H,CH),7.23(d,J=1.1Hz,1H,CH ),7.20–7.17(m,2H,CH),7.14(d,J=4.4Hz,2H,CH),7.07(m,J=9.1,1H,CH),6.93(d,J=7.7Hz,2H ,CH),6.76(d,J=8.3Hz,1H,CH). 13 CNMR (100MHz, CD...

Embodiment 2

[0042] Synthesis of 2-{2-[(2,6-diisopropyl)phenoxy]anilino}tropone

[0043]

[0044] Add tris(dibenzylidene-BASEacetone)dipalladium (0.09 g, 0.01 mmol), 1,1'-binaphthyl-2,2'-bisdiphenylphosphine to a Schlenk bottle with a magnet under nitrogen (0.012 g, 2.0 mmol), 2-trifluoromethanesulfonate cycloheptatrienone (0.53 g, 2.0 mmol), 2-[(2,6-diisopropyl)phenyl]aniline (0.65 g, 2.4 mmol) and 4 ml of toluene. The mixture was stirred at 80° C. for 24 hours, cooled down to room temperature after the reaction, filtered through a 10 cm silica gel column, and washed with 200 ml of dichloromethane. Finally, the eluent was passed through the column with petroleum ether:ethyl acetate=10:1 to obtain a yellow product (0.45 g, yield 60%). 1 HNMR (400MHz, CDCl 3 ):δ=8.99(s,1H,NH),7.53–7.45(m,1H,CH),7.38–7.25(m,2H,CH),7.25–7.14(m,5H,CH),7.08–7.00( m,1H,CH),6.78(m1H,CH),6.52–6.44(m,1H,CH),2.94(m,2H,CH(CH 3 ) 2 ), 1.10 (dd, J=13.8, 6.9Hz, 4H, CH 3 ) ppm. 13 CNMR (100MHz, CDCl 3 ): δ=17...

Embodiment 3

[0046] Synthesis of 2-[2-(phenylmercapto)anilino]tropone

[0047]

[0048] Add tris(dibenzylidene-BASEacetone)dipalladium (0.09 g, 0.01 mmol), 1,1'-binaphthyl-2,2'-bisdiphenylphosphine to a Schlenk bottle with a magnet under nitrogen (0.012 g, 2.0 mmol), 2-trifluoromethanesulfonate tropotrienone (0.53 g, 2.0 mmol), 2-aminodiphenyl sulfide (0.44 g, 2.4 mmol, from Anaiji company) and 4 ml of toluene. The mixture was stirred at 80° C. for 24 hours, cooled down to room temperature after the reaction, filtered through a 10 cm silica gel column, and washed with 200 ml of dichloromethane. Finally, the eluent was passed through the column with petroleum ether:ethyl acetate=10:1 to obtain a yellow product (0.48 g, yield 83%). 1 HNMR (400MHz, CDCl 3 ): δ=8.86(s,1H,NH),7.42(s,2H,CH),7.46–7.13(m,9H,CH),7.06(t,J=10.2Hz,1H,CH),6.96(d ,J=10.3Hz,1H,CH),6.74(t,J=9.1Hz,1H,CH)ppm. 13 CNMR (100MHz, CDCl 3 ):δ=177.23(C=O),152.97(C-N),138.25,137.37,135.72,134.13,133.52,131.93,131.46(,131.1...

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Abstract

The invention relates to an aluminum compound catalyst containing a cycloheptatriene structure, its synthesis and application, and specifically discloses a ring-opening polymerization of lactide catalyzed by an aluminum compound containing a cycloheptatriene structure. Such catalysts can efficiently catalyze the ring-opening polymerization of lactide. The high activity of such catalysts may be due to the formation of smaller chelate rings with aluminum and greater ring tension. The activity of the catalyst containing the side arm effect is significantly higher than that of the catalyst without the side arm effect. When the monomer ratio is 100:1 and the temperature is 80°C, the lactide can be almost completely polymerized. At the same time, the side arm effect also affects the tacticity of PLA.

Description

technical field [0001] The invention relates to the synthesis and application of an aluminum catalyst containing a cycloheptatriene structure, which can efficiently catalyze the ring-opening polymerization of lactide under the action of an initiator. When the monomer ratio is 100:1 and the temperature is 80°C, lactide can be almost completely polymerized. At the same time, the side arm effect also affects the tacticity of PLA. Background technique [0002] Aliphatic polyesters, such as polylactic acid and polycaprolactone, have attracted extensive attention in recent years for their reproducibility through biodegradation. More importantly, we can adjust the physical properties of such polymers during polymerization and processing, making them widely used in biology, medicine, microelectronics and other fields. At present, polylactic acid is obtained industrially by catalyzing the ring-opening polymerization of lactide initiated by stannous octoate. However, tin is potenti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/20C07C319/20C07C323/37C07F5/06C08G63/08C08G63/84
Inventor 陈昶乐李敏陈敏
Owner UNIV OF SCI & TECH OF CHINA
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