Coupling of amino-functional chemicals to hydrocarbons through peroxide catalyst?
Is it possible to take an amino-functional particle (say, with aminopropyl groups) and bind it to a hydrocarbon (polypropylene or aromatics) by using
a peroxide as a catalyst?
I know that peroxides will open up bond sites on hydrocarbons by stripping off hydrogen atoms, leaving unsaturated carbons behind.
I also know that sulfonylazides can be used to functionalize hydrocarbon polymers, since at high temperature the azide will partially decompose to
form reactive nitrenes that are capable of insertion into carbon-hydrogen bonds.
However, sulfonylazides are expensive, whereas the amino chemicals and peroxide catalysts are relatively cheap.
My thought is that the peroxide could potentially strip the hydrogen molecules from the amino (R-NH2 into R-N-...I think), which is then
capable of insertion into the hydrocarbon. The N-H bond energies are lower than C-H energies so I assume the amino stripping would occur first...but
the reaction could be taken in such a way to introduce the polymer later.
Is this a reasonable route or am I way off base and should be going about with another catalyst? A quick look on wikipedia yields some interesting
paths...but involving chemicals I don't have on hand. http://en.wikipedia.org/wiki/Nitrene
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