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A kind of preparation method and application of phosphorous and nitrogen-containing ligand alkylaluminum compound

A compound, the technology of alkylaluminum, which is applied in the field of preparation of organoaluminum compounds, can solve the problems of low reaction activity, long reaction time, high reaction temperature, etc., and achieve the effects of stable properties, high catalytic activity and convenient preparation

Active Publication Date: 2021-01-26
QINGDAO UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Wherein the most widely used is stannous octoate, which has a faster reaction rate and can obtain polyester materials with high yield and high molecular weight, but it also has the disadvantage that the reactivity is not very high, requiring a long reaction time and relatively high Disadvantages of high reaction temperature

Method used

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  • A kind of preparation method and application of phosphorous and nitrogen-containing ligand alkylaluminum compound
  • A kind of preparation method and application of phosphorous and nitrogen-containing ligand alkylaluminum compound
  • A kind of preparation method and application of phosphorous and nitrogen-containing ligand alkylaluminum compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1, ligand L4 (2-Ph 2 P-C 6 h 4 -CH 2 -NH-2,6-Ph 2 CH-4- i Pr-C 6 h 2 ) preparation

[0040] 2,6-bis(diphenylmethyl)-4-isopropyl-aniline (2,6-Ph 2 CH-4- i Pr-C 6 h 2 -NH 2 , 4.67g, 10.0mmol), 2-diphenylphosphorbenzaldehyde (2.90g, 10.0mmol), 10mg p-toluenesulfonic acid were mixed in 100mL toluene, refluxed under nitrogen atmosphere for 12 hours, washed with methanol, and the resulting product Amine (2-Ph 2 P-C 6 h 4 -CH=N-2,6-Ph 2 CH-4- i Pr-C 6 h 2 , 2.22g, 3mmol) and LiAlH 4 (0.57g, 15mmol) was dissolved in 60mL of anhydrous tetrahydrofuran, reacted at room temperature in a nitrogen atmosphere for 2 days, quenched with 0.57ml of water, 0.57ml of 15% aqueous sodium hydroxide solution, and processed to obtain a white solid L4 compound 1.93g, 2.6 mmol, yield 87%. 1 H NMR (CDCl 3 ):δ7.34–7.11(m,25H),7.04(d,J=7.0Hz,8H),6.83(dd,J=7.4and 4.5Hz,1H),6.64(s,2H),6.17(s, 2H), 4.09–4.01(br,2H), 3.28–3.20(br,1H), 2.61(hept, J=6.7Hz, 1H), 0.97(d, J=6...

Embodiment 2

[0041] Embodiment 2, compound Al1 (L1AlMe 2 ) preparation

[0042] Under nitrogen atmosphere, the ligand L1(2-Ph 2 P-C 6 h 4 -CH 2 -NH-2,6-Ph 2 CH-4- i Pr-C 6 h 2 , 0.367g, 1mmol) was dissolved in 20mL of toluene, slowly added 1.1 molar equivalents of AlMe 3 (1.2mmol, 0.6mL, 2M solution in toluene), stirred at 80°C for 16 hours. The toluene solvent was removed under reduced pressure, and n-hexane (3×10 mL) was added for washing to obtain 0.354 g, 0.82 mmol, 82% of Al1 compound as a white solid. 1 H NMR (CDCl 3 ):δ7.66(t, J=6.3Hz, 1H), 7.47(t, J=7.5Hz, 1H), 7.45–7.41(m, 2H), 7.39–7.32(m, 4H), 7.30–7.20( m,5H),7.10(t,J=8.3Hz,1H),7.02(dd,J=8.5and 7.3Hz,2H),6.79(d,J=8.1Hz,2H),6.49(t,J=7.2 Hz,1H),4.52(s,2H),-0.50(d,J PH =4.3Hz,6H). 13 C NMR (CDCl 3 ):154.29,149.89(d,J PC =14.1Hz), 135.81, 133.60(d, J PC =12.9Hz), 131.30, 130.74, 130.38 (d, J PC =9.5Hz), 129.13, 129.03, 128.85, 128.51, 128.19, 127.51 (d, J PC =5.6Hz), 127.11, 126.80, 115.05, 52.05, -7.92 (d, J PC...

Embodiment 3

[0043] Embodiment 3, compound Al2 (L2AlMe 2 ) preparation

[0044] Experimental procedure is with embodiment 2, complex Al2 (L2AlMe 2 ) Yield: 0.361 g, 0.80 mmol, 80%. 1 H NMR (CDCl 3 ): δ7.56–7.49(m,2H),7.49–7.43(m,4H),7.43–7.36(m,4H),7.31(t,J=7.4Hz,1H),7.22(t,J=7.4 Hz, 1H), 7.09–7.01(m, 2H), 6.99(d, J=7.4Hz, 2H), 6.84(t, J=7.4Hz, 1H), 4.15(s, 2H), 1.98(s, 6H ),-0.67(d,J PH =3.7Hz,6H). 13 C NMR (CDCl 3 ):152.46,150.98(d,J PC =13.4Hz), 137.80, 134.92, 134.03 (d, J PC =12.7Hz), 130.95, 130.80, 129.15 (d, J PC =9.1Hz), 128.89, 128.82, 128.59, 128.08, 127.40, 127.11, 127.01 (d, J PC =5.7Hz), 122.61, 57.49, 19.59, -9.18 (d, J PC =21.3Hz). 31 P NMR (CDCl 3 ):-25.01.Anal.Calcd for C 29 h 31 AlNP: C, 77.14; H, 6.92; N, 3.10. Found: C, 77.05; H, 6.71; N, 2.99.

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Abstract

The invention discloses a preparation method of a 2-diphenylphosphinobenzaldehyde-aniline alkyl aluminum compound and an application of the compound in ring opening polymerization of lactone and lactide. The preparation method of the 2-diphenylphosphinobenzaldehyde-aniline alkyl aluminum compound comprises the following steps: dissolving a 2-diphenylphosphinobenzaldehyde-aniline ligand into 30-100mL of an anhydrous solvent, adding 1.0-1.5 molar equivalents of aluminum alkyl, and performing a stirring reaction under the protection of a nitrogen gas for 12-24 h, wherein the reaction temperatureis 20-100 DEG C; and removing the solvent under reduced pressure, and performing washing for three times by using a poor solvent to obtain the corresponding alkyl aluminum compound. The 2-diphenylphosphinobenzaldehyde-aniline alkyl aluminum compound provided by the invention is a high-efficiency catalyst of ring opening polymerization of the lactone and the lactide, and can be used for a polymerization reaction of different lactones; the 2-diphenylphosphinobenzaldehyde-aniline alkyl aluminum compound has the following very obvious advantages: the raw materials are cheap and easy to obtain, the synthetic route is simple, the product yield is high, the properties are stable; the activity of catalyzing ring opening polymerization of caprolactone is high, the controllability is good; and theprepared polycaprolactone polymer material has a controlled molecular weight and a low molecular weight distribution.

Description

technical field [0001] The invention relates to a preparation method and application of a class of organoaluminum compounds, in particular to a preparation method of 2-diphenylphosphorbenzaldehyde-aniline alkylaluminum compound and its application in ring-opening polymerization of lactone and lactide. Background technique [0002] Compared with traditional polymer materials, degradable polyester polymer materials have obvious advantages in terms of environmental friendliness and biocompatibility. They are a new generation of materials with broad development prospects, and meet the requirements of ecological and sustainable development. Among them, aliphatic polyester is a very important class of degradable polymer materials, which has been developed rapidly in recent years. [0003] Biodegradable polyesters such as PCL and PLA have good biocompatibility and biodegradability, and can be completely biodegraded under natural environmental conditions without any pollution to the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50B01J31/24C08G63/84C08G63/08
Inventor 刘绍峰卫传志李志波
Owner QINGDAO UNIV OF SCI & TECH