Optimizer Crashes when attempting to optimize 245 MB File

Hi there, 

We've been attempting to optimize large files that are output from our xml/text editor. 
The output file is 245 MB, which is too large for our clients to use as is.
When attempting to optimize, Save as -> Optimized PDF, it starts the process but shortly after crashes without an error message.
We suspected that it could be an issue with the format of the document, but we trimmed down the document to be smaller, 13 MB, and it was able to optmize the file without issue. 

We suspect it's a memory/resources issue as it while watching task manager, it reaches almost 100% resource use before it closes the Adobe. Not sure if anyone has run into an issue like this or would know how to start remedying it.

Any help would be appreciated.