Microsoft only made one initial release to make Office 2011 compatible with High Sierra. That was shortly after HS came out. Later point releases made it less compatible. So it's no surprise at all that a 10 year old piece of software doesn't work in Mojave.

Aug 05, 2016 So can only suggest as try remove the Cannon printer, then its drivers (from Device and Printers Control Panel, select a printer then Print server properties and select the cannon driver on the Driver tab, and Remove) and any cannon software. Reboot and see if the Print to PDF works without those as a test.

On top of that, Office 2008 is 32 bit software. Mojave only partly supports 32 bit apps. They may work, they may not. The OS that comes after Mojave will be 64 bit only. No 32 bit apps will work at all.

Print To Pdf

Time to upgrade. You can get the Home Edition of Office 2019 for $160. If you need Outlook, then it'll be $260 for the Home/Business version.