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Application of Palladium Source Catalysts in Alkyne Polymerization
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A catalyst and polymerization technology, applied in the field of alkyne polymerization, to achieve the effect of less poisoning, lower polymerization cost, and high polymerization activity
Active Publication Date: 2021-07-20
BEIJING INSTITUTE OF TECHNOLOGYGY
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Palladium sources are widely used in organic synthesis, but examples of direct use in polymerization reactions have not been reported yet
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Embodiment 1
[0050] 1) Add 2 mmol of disubstituted alkyne monomer to an eggplant-shaped bottle, add 3 mL of 1,1,2,2-tetrachloroethane solution, stir with a magnetic stirrer until dissolved, add 0.02 mmol to dissolve in 1,1 , 2,2-tetrachloroethane on palladium carbon, stirred and reacted in an oil bath at 60°C for 2h;
[0051] (2) After the reaction is over, take the eggplant bottle out of the oil bath, cool to room temperature, drop the resulting reaction solution into the petroleum ether solution for sedimentation, terminate the reaction, precipitate solid matter, filter it with petroleum ether Wash three times, vacuum-dry the resulting solid at 40°C to constant weight to obtain a polymer product, weigh the polymer product and obtain a yield of 78% from the above activity formula, and an activity of 5.9 kg·mol Pd -1 h -1 .
[0052] The polymer product prepared in this embodiment is tested as follows:
[0053] (1) GPC detection
[0054] The GPC detection result of the polymerization p...
Embodiment 2
[0056] (1) catalyzer changes palladium acetate into, all the other are with embodiment 1 step (1);
[0057] (2) With embodiment 1 step (2).
[0058] The polymer product prepared in this embodiment is tested as follows:
[0059] (1) GPC detection
[0060] The GPC detection result of the polymerization product prepared in this embodiment is shown in figure 2 ,Depend on figure 2 Integral at middle retention time 17.3min shows that the number average molecular weight M of the polymerization product n =21000, molecular weight distribution M w / M n = 1.93.
Embodiment 3
[0062] (1) catalyzer changes palladium chloride into, all the other are with embodiment 1 step (1);
[0063] (2) With embodiment 1 step (2).
[0064] The polymer product prepared in this embodiment is tested as follows:
[0065] (1) GPC detection
[0066] The GPC detection result of the polymerization product prepared in this embodiment is shown in image 3 ,Depend on image 3 Integral at middle retention time 15.4min shows that the number average molecular weight M of the polymerization product n =20000, molecular weight distribution M w / M n = 1.94.
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Abstract
The invention relates to the application of a palladium source catalyst in catalyzing alkyne polymerization, belonging to the field of alkyne polymerization. The application is as a catalyst to catalyze the polymerization of alkynes, and as a catalyst to catalyze the polymerization of disubstituted alkynes. Unlike known palladium catalysts, palladium sources can be purchased directly, and can catalyze the polymerization of disubstituted alkynes without coordination with various ligands, and there is no need to add cocatalysts during the polymerization process, such as silver trifluoromethanesulfonate ( AgOTf) and tetrakis(3,5-bis(trifluoromethyl)phenyl)sodium borate (NaBAF), etc., can obtain high molecular weight polymers, and obtain cis-selective poly(1- Chloro-2-Phenylacetylene) (PCPAs). The invention solves the problems of complex synthesis of disubstituted alkyne polymerization catalysts, co-catalyst participation in the polymerization process, and high cost, and is simpler, economical and efficient. This work provides a new idea for the polymerization of disubstituted alkynes.
Description
technical field [0001] The invention relates to the application of a palladium source catalyst in the polymerization of disubstituted alkynes and functional alkynes, belonging to the technical field of alkyne polymerization. Background technique [0002] Poly(di-substituted acetylenes), referred to as PDSAs, have attracted increasing attention due to their higher stability, selective gas permeability, and efficient luminescent properties than poly-monosubstituted acetylenes. . Poly(1-chloro-2-phenylacetylene)s (PCPAs) have an electron-withdrawing chlorine atom on one side of the double bond in the polymer chain and a substituted phenyl group on the other side for their excellent liquid and gas permeability , has received extensive attention from academia and industry, maintains high stability in air even at high temperature, and has excellent luminescent properties, which have potential applications in many fields. For the polymerization of disubstituted alkynes, the polym...
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