Aluminum compound based on pyrrole derivatives, preparation method of aluminum compound and polylactic acid preparation method

A technology of pyrrole derivatives and aluminum compounds, which is applied in the field of catalysis, can solve the problem of low activity stereoselectivity, achieve the effects of enhanced selectivity, improved stereoregularity, and enhanced catalytic performance

Inactive Publication Date: 2015-11-25
CHANGCHUN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

But the activity (monomer conversion rate 31~82%) and stereoselectivity (59~70%) of the above reported catalyst catalyzed ring-opening polymerization of lactide are all low
In the prior art, there have been no reports on the preparation of pyrrole-containing aluminum compounds by the reaction of m-xylylenediamine and pyrrole derivatives and their use to catalyze the ring-opening polymerization of lactide to prepare polylactic acid

Method used

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  • Aluminum compound based on pyrrole derivatives, preparation method of aluminum compound and polylactic acid preparation method
  • Aluminum compound based on pyrrole derivatives, preparation method of aluminum compound and polylactic acid preparation method
  • Aluminum compound based on pyrrole derivatives, preparation method of aluminum compound and polylactic acid preparation method

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preparation example Construction

[0055] Optionally, when R is -CH 3 or -CH 2 CH 3 When, the present invention provides a kind of preparation method based on pyrrole derivative aluminum compound, comprises the following steps: the ligand of formula (II) structure and Al(R') 3 React in a solvent to obtain an aluminum compound with the structure of formula (III). Wherein, the solvent is an organic solvent well known to those skilled in the art, preferably tetrahydrofuran or toluene.

[0056] R 1、 R 2、 R 3 and R 4 The choice of influences the choice of solvent, when R 1、 R 2 and R 3 selected from -H, -Cl, -Br or -NO 2 , R 4 selected from -H or -CH 3 When, the reaction solvent is preferably tetrahydrofuran; R 1 , R 2 and R 3 independently selected from -H, -CH 3 、-CH 2 CH 3 、-CH(CH 3 ) 2 、-C(CH 3 ) 3 ,-(CH 2 ) 3 CH 3 , -Cl, -Br, -NO 2 、-SiPh 3 , -Si(CH 2 CH 3 ) 3 , -Si(CH 3 ) 3 Or adamantyl, where Ph is an aromatic hydrocarbon group, where Ph is an aromatic hydrocarbon group, R 4 s...

Embodiment 1

[0081] Embodiment 1 structural formula is the synthesis of the ligand IIa of II

[0082] IIa:R 1 = R 2 = R 3 = R 4 =-H

[0083] Under the protection of nitrogen, Va(R 1 = R 2 = R 3 = R 4 =-H, 0.238g, 2.50mmol) and VI-type m-xylylenediamine (0.136g, 1.00mmol) were dissolved in 15mL of absolute ethanol, heated to reflux for 8h. After cooling to room temperature, concentrated, the obtained crude product was used Column chromatography separation, eluent is sherwood oil: ethyl acetate (volume ratio is 12:1), obtains pure product IIa is yellow solid, and output is 0.233g, and productive rate is 80.5%.

[0084] The ligand IIa obtained in Example 1 was analyzed by a mass spectrometer, and the result obtained was: MZNDI-TOF(THF), m / z=290.30.

[0085] Utilize elemental analysis to analyze the ligand IIa obtained in embodiment 1, obtain the result:

[0086] Elem. Anal. Calc. (%): C, 74.46; H, 6.25; N, 19.30. Found: C, 74.39; H, 6.21; N, 19.17.

Embodiment 2

[0087] Embodiment 2 structural formula is the synthesis of the ligand IIb of II

[0088] IIb:R 1 = R 2 = R 3 =-CH 3 , R 4 =-H

[0089] Under the protection of nitrogen, the Vb (R 1 = R 2 = R 3 =-Me,R 4 =-H, 0.343g, 2.50mmol) and VI m-xylylenediamine (0.136g, 1.00mmol) were dissolved in 20mL of toluene, a catalytic amount of p-toluenesulfonic acid was added, and heated to reflux for 12h. After being cooled to room temperature, concentrated, the gained crude product is separated by column chromatography, eluent is sherwood oil: ethyl acetate (volume ratio is 18:1), obtains pure product IIb is yellow solid, and output is 0.289g, productive rate was 77.3%.

[0090] The ligand IIb obtained in Example 2 was analyzed by a mass spectrometer, and the result was obtained: MZNDI-TOF (THF), m / z=374.20.

[0091] Utilize elemental analysis to analyze the ligand IIb obtained in embodiment 2, obtain the result:

[0092] Elem.Anal.Calc.(%): C, 76.97; H, 8.07; N, 14.96. Found: C, 76...

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Abstract

The invention provides an aluminum compound based on pyrrole derivatives, a preparation method of the aluminum compound and a polylactic acid preparation method. The molecular structure of the aluminum compound is shown as the formula (I). The aluminum compound is prepared through reaction of m-xylylenediamine and the pyrrole derivatives. On one hand, the aluminum compound serves as a catalyst with aluminum as central atoms and has high catalytic reaction activity during lactide ring-opening polymerization catalysis, and high polymerization reaction activity is obtained; on the other hand, a ligand has proper steric hindrance, an ideal stereoscopic effect is obtained, and stereoscopic selectivity of racemization lactide ring-opening polymerization is improved. The invention further provides the polylactic acid preparation method. Polylactic acid obtained by catalyzing racemic lactide through the aluminum compound is polylactic acid with isotactic heterogeneous major components, and polylactic acid with 72.0% of isotaxy components is obtained. Please see the formula in the specification.

Description

technical field [0001] The invention belongs to the field of catalysis, and in particular relates to a pyrrole derivative-based aluminum compound, a preparation method thereof, and a preparation method of polylactic acid. Background technique [0002] Polylactic acid (also known as polylactide) is an environmentally friendly polymer material synthesized by chemical or biological methods. Due to its biodegradability, the amount of carbon dioxide emitted as waste after use is higher than that of traditional general plastics. The amount is reduced by at least 60%, so this material is widely used in packaging, biopharmaceutical, medical and industrial and agricultural fields. The raw materials in the present invention can come from renewable resources such as corn or sugar beet instead of petroleum sources, and the downstream products of the prepared polylactic acid can be degradable plastics (replacing non-degradable plastics such as traditional polyethylene, which is beneficia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/06B01J31/22C08G63/87C08G63/08
CPCY02P20/52
Inventor 高波李东霓李艳伟李艳辉段潜王恒国沈贤德司振君万玉春
Owner CHANGCHUN UNIV OF SCI & TECH
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