It all depends on how much memory you have on your PI system and how it is set up. This is like asking how long is a piece of string. Have a look at the links below to minimize the possibility of running out of java memory. Its a good question but there is not certain way to determine what the biggest file is we can transfer using PI. There are to many variables in play.
The links below should help you minimize the java memory problem.
This link was posted a long time ago but is still valid.
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