Yes technically it is possible.
You would have to create a print driver for you OS. One that formats the printed media to the Iliad layout
And install a print driver on your Iliad to receive the content from your print driver.
Take a look at its a good place to start.
http://www.cups.org
This would be an AWSOME project if designed correctly this can be modular enough for all eBooks
Ie I would start with making the drivers.
Print to Iliad Driver
Print to SONY
Print to Mobi