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Functionalized polyolefins

From the journal: Chemical Society Reviews. Post-polymerization functionalization of polyolefins. Nicole K. You have access to this article.

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Figure 1. Hillmyer and Hartwig et al. Results and Discussion. We have recently developed a copper-based catalytic system for the functionalization of alkanes through insertion of CHCO2Et into C—H bonds using commercial ethyl diazoacetate EDA as the carbene source. The polymerization of transbutene with a-di-imine Ni II catalysts11 provides a high molecular weight polyolefin with a well-defined structure corresponding to a linear polyethylene with a methyl branch on every third carbon atom precisely Scheme 1.

We have carried out the room temperature reaction of ethyl diazoacetate and the poly 2-butene 12 in the presence of catalytic amounts of TpBr3Cu NCMe Scheme 1. Table 1.

Mw and Mn values x 10 3 g mol. Figure 1 shows the 1H NMR spectrum of the functionalized polymer. The degree of incorporation determined by NMR was ca. A significant feature of this methodology was revealed by GPC of the functionalized materials Table 1, entries 1—3. Note that molecular weights are apparent molecular weights relative to linear polyethylene standards; i. As shown in Figure 1, the 1H NMR spectrum13 of the modified polymer displays again the resonances attributable to — CH2—CO2Et groups with similar patterns to those observed in the functionalization of smaller alkanes.

The existence of a large. Figure 2.

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This could also account for the observed increase in the degree of ester group incorporation in terms of the number of carboxylates per C , as inferred from the data in entries 3 and 9 in Table 1. These results are in good agreement with the observed regioselectivity in the case of 2-methylbu-tane and 2-methylpentane.


Since control of the degree of ester incorporation is desirable due to its relationship to polymer properties, we have performed a series of experiments where we have modified the following variables: i EDA addition time, ii catalyst loading, and iii polymer:EDA ratio Table 1, entries 4— Although each of them exerts a certain degree of influence in the number of :CHCO Figure 3. Left: polymer repeat units:EDA Right: polymer repeat units:EDA , incorporation: 2. If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

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Post-polymerization functionalization of polyolefins - Chemical Society Reviews (RSC Publishing)

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