The Effect of 1,2- and trans-1,4-Units on Ketonization of Polybutadienes by Nitrous Oxide

Earlier it was shown that the oxygenation of double bonds in polydienes by nitrous oxide (N2O) via the 1,3-dipolar cycloaddition mechanism (the so-called ketonization reaction) provides a synthetic route for obtaining a new type of carbonyl functionalized polymers and oligomers–unsaturated polyketon...

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Veröffentlicht in:Industrial & engineering chemistry research 2024-02, Vol.63 (6), p.2696-2704
Hauptverfasser: Semikolenov, Sergey V., Ivanov, Dmitry P., Dubkov, Konstantin A.
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Sprache:eng
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Zusammenfassung:Earlier it was shown that the oxygenation of double bonds in polydienes by nitrous oxide (N2O) via the 1,3-dipolar cycloaddition mechanism (the so-called ketonization reaction) provides a synthetic route for obtaining a new type of carbonyl functionalized polymers and oligomers–unsaturated polyketones. Here, the ketonization of polybutadiene with a relatively high content of trans-1,4-units and 1,2-units at 160–230 °C and elevated pressure was studied. Oxygenated polymer products containing from 0.3 to 8.8 wt % oxygen in the form of carbonyl, mainly ketone, groups and having M n from 34000 to 860 g/mol, respectively, have been obtained. The conversion of ca. 10% of double bonds in the parent polybutadiene during the reaction transforms it into carbonyl functionalized liquid rubber. A comparison of the obtained results with those for ketonization of cis-1,4-polybutadiene has revealed the effect of cis/trans isomerism of 1,4-units and the content of 1,2-units on the reaction mechanism and the characteristics of the resulting polymer products.
ISSN:0888-5885
1520-5045
DOI:10.1021/acs.iecr.3c03873