If executing this via
xp_cmdshell then there shouldn't be any limitation. The first thing I would check is the environment. When you open a command prompt it is set up for however your account is configured. But SQL Server doesn't run as your account. It will either be its own account, or Local System, or a service account. I don't think Local System can have its own environment configured (I don't remember off hand as I haven't looked into this in years, but I do remember that there is one built-in account, either Local System or NETWORK that doesn't have its own profile) but most likely whatever SQL Server is running as isn't configured the same. In this case, I am guessing that at the very least the PATH environment variable is missing one or more entries, and possibly also there might be one or more missing environment variables (e.g. INCLUDE, LIB, LIBPATH, NETFXSDKDir, etc).
To check, open a command prompt, verify that your obfuscation app works, then run "SET" to see a list of all your environment variables. Then, in SQL Server, execute:
EXEC xp_cmdshell N'SET';
And compare the output of both. If there are paths and/or entire variables missing from the SQL Server-based list, then find the Logon Account and add those missing items to that account's environment setup.