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8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound and preparation method and application thereof

A kind of hydrogenated quinoline, alkyl aluminum technology, applied to the application of lactone and lactide ring-opening polymerization, 8-N-arylamine-hydrogenated quinoline complex alkyl aluminum compound and its preparation field, to achieve product yield The effect of high rate, stable properties, and easy control of catalytic performance

Active Publication Date: 2016-10-26
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aminohydroquinoline ligands contain two types of different nitrogen atoms, combined with different heterocyclic skeletons, conveniently construct different coordination models and complex with different metals, and regulate the steric effect and electronic effect of metal catalysts, so Caused the great interest of numerous scholars, although there are some reports (Organometallics2015,34,3222; Inorg.Chem.Front.2015,2,223; Organometallics2014,33,1053; DaltonTrans.2011,40,8436), but there is no relevant aluminum compound and its report as a catalyst for ring-opening polymerization of lactone and lactide

Method used

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  • 8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound and preparation method and application thereof
  • 8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound and preparation method and application thereof
  • 8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1, preparation of ligand L1 (8-N-2,6-diisopropylaniline-hydroquinoline)

[0048] Under nitrogen atmosphere, 5,6,7-trihydroquinolin-8-one (1.48g, 10mmol), 2,6-diisopropylaniline (1.95g, 11mmol) and toluenesulfonic acid (20mg ) was dissolved in 50mL toluene, and refluxed for 12 hours. The toluene solvent was removed under reduced pressure, 50 mL of methanol and 50 mL of dichloromethane were added to dissolve, 6 equivalents of sodium borohydride (2.28 g, 60 mmol) was slowly added, and the reaction was stirred at room temperature for 10 hours. Silica column chromatography separated to obtain a yellow solid L11.31g, 5.60mmol, yield 56.0%.

[0049] FT-IR (KBr, cm -1 ):3311, 3060, 2955, 2864, 1574, 1457, 1417, 1324, 1250, 1194, 1147, 1104, 1055, 1002, 935, 807, 781, 745, 707, 546. 1 HNMR (CDCl 3 ): δ8.48(d, 1H, J=4.5Hz, quino-H), 7.42(d, 1H, J=7.6Hz, quino-H), 7.14-7.11(m, 4H, quino-H+Ar- H), 4.46 (br, 1H, N-H), 4.04 (dd, 1H, J=8.5, 4.6Hz, NCH), 3.59 (hept, 2H,...

Embodiment 2

[0050] Example 2, preparation of ligand L2 (8-N-2,6-diethylaniline-hydroquinoline)

[0051] The experimental procedure is the same as that in Example 1, the yield of ligand L2 (8-N-2,6-diethylaniline-hydroquinoline): 1.73 g, 6.20 mmol, 62.0% yield.

[0052] FT-IR (KBr, cm -1 ):3341, 3043, 2958, 2904, 1564, 1460, 1415, 1325, 1240, 1194, 1176, 1123, 1056, 938, 827, 780, 746, 717, 542. 1 HNMR (CDCl 3 ): δ8.48(d, 1H, J=4.2Hz, quino-H), 7.43(d, 1H, J=7.6Hz, quino-H), 7.16-7.12(m, 4H, quino-H+Ar- H), 4.38(br, 1H, N-H), 4.10(dd, 1H, J=8.4, 4.3Hz, NCH), 2.89-2.78(m, 2H, quino-H), 2.35(q, 4H, J=6.9 Hz, CH 2 CH 3 ), 2.09-1.97(m, 2H, quino-H), 1.80-1.65(m, 2H, quino-H), 1.29(t, 6H, J=6.9Hz, CH 2 CH 3 ). 13 CNMR (CDCl 3 ): δ157.42, 148.11, 146.62, 141.98, 135.91, 132.15, 125.06, 123.57, 122.98, 60.55, 29.77, 28.80, 27.89, 24.22, 20.20.Anal.CalcdforC 21 h 28 N 2 : C, 81.38; H, 8.63; N, 9.99. Found: C, 81.35; H, 8.52; N, 9.72.

Embodiment 3

[0053] Example 3, preparation of ligand L3 (8-N-2,6-dimethylaniline-hydroquinoline)

[0054] The experimental procedure is the same as that in Example 1, and the yield of ligand L3 (8-N-2,6-dimethylaniline-hydroquinoline): 1.28 g, 5.08 mmol, 50.8%.

[0055] FT-IR (KBr, cm -1 ):3333, 3042, 2940, 1589, 1570, 1471, 1438, 1256, 1214, 1186, 1160, 1093, 1033, 1013, 877, 846, 791, 752, 705, 681, 571. 1 HNMR (CDCl 3 ): δ8.47 (d, 1H, J = 4.3Hz, quino-H), 7.42 (d, 1H, J = 7.6Hz, quino-H), 7.12 (dd, 1H, J = 7.6, 4.7Hz, quino -H), 7.02(d, 2H, J=7.4Hz, Ar-H), 6.87(t, 1H, J=7.4Hz, Ar-H), 4.37-4.36(m, 1H, NCH), 4.01(br , 1H, NH), 2.94-2.72(m, 2H, quino-H), 2.33(s, 6H, Me), 2.03-1.86(m, 2H, quino-H), 1.85-1.71(m, 2H, quino-H) -H). 13 CNMR (CDCl3): δ157.75, 147.32, 145.01, 136.88, 132.07, 131.28, 128.80, 122.21, 122.06, 57.32, 29.81, 28.70, 19.61, 19.09. 17 h 20 N 2 : C, 80.91; H, 7.99; N, 11.10. Found: C, 80.78; H, 8.15; N, 11.02.

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Abstract

The invention discloses an 8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound and a preparation method and application thereof. The preparation method of the 8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound comprises the following steps that 8-N-arylamine-hydrogenation quinoline ligand is dissolved in an anhydrous solvent, aluminum alkyl is added, stirring is carried out under protection of nitrogen at the room temperature, the solvent is removed through decompression, a poor solvent is used for carrying out washing for three times, and the target aluminum alkyl compound is obtained. The 8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound is an efficient lactone and lactide ring-opening polymerization catalyst and can be used for lactone and lactide ring-opening polymerization reaction. According to the 8-N-arylamine-hydrogenation quinoline complexation aluminum alkyl compound, the raw materials are low in price and easy to get, the synthetic route is simple, the product yield of high, characters are stable, the prepared product is abundant and changeable in structure, the catalytic performance is easy to regulate, the requirements of different kinds of lactone and lactide ring-opening polymerization can be met, prepared aliphatic polyester high polymer material is controllable in structure and performance, and requirements of industrial departments can be met.

Description

technical field [0001] The invention relates to a preparation method and application of a class of organoaluminum compounds, in particular to an 8-N-arylamine-hydroquinoline complexed alkylaluminum compound, a preparation method and its application in ring-opening polymerization of lactones and lactides. Background technique [0002] In the transition from an exhausted resource economy to a renewable resource economy, countries all over the world attach great importance to the development and application of degradable polymer materials. It is a new generation of promising materials and meets the requirements of ecological and sustainable development. Among them, aliphatic polyester is a very important class of degradable polymer materials, which has developed rapidly in recent years. [0003] Aliphatic polyester can be completely biodegraded under natural environmental conditions without any pollution to the environment. Its excellent biocompatibility, permeability and low t...

Claims

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Application Information

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IPC IPC(8): C07F5/06C08G63/84C08G63/08
CPCC07F5/066C08G63/08C08G63/823C08G63/84
Inventor 刘绍峰李志波张杰
Owner QINGDAO UNIV OF SCI & TECH
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