You can do something like this to get access to the directory
sql> create directory temp as 'c:\temp';
directory created.
sql> create directory bin as 'c:\bin';
Directory created.
SQL> host touch c:\temp\dummy_file.dat
SQL> host cat c:\temp\dir_list.cmd
@echo off
dir /s /b C:\oracle\doc\*.pdf
SQL> create table pdf_files
2 ( file_name varchar2(255)
3 )
4 organization external
5 (
6 type oracle_loader
7 default directory temp
8 access parameters
9 (
10 records delimited by newline
11 preprocessor bin: 'dir_list.cmd'
12 )
13 location ('dummy_file.dat')
14 )
15 reject limit unlimited;
Table created.
So we have an external table, that will run the "dir_list.cmd" file, which in turn, shows all pdf's under a given directory.
Hence it becomes something you can query
SQL> select * from pdf_files where rownum < 10;
FILE_NAME
---------------------------------------------------------
C:\oracle\doc\10.2\B19306_01\appdev.102\a58231.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\a96109.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\b14249.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\b14250.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\b14251.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\b14252.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\b14253.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\b14254.pdf
C:\oracle\doc\10.2\B19306_01\appdev.102\b14255.pdf
9 rows selected.
Once you have the pdf you need, you can either download via browser, eg
https://asktom.oracle.com/pls/asktom/f?p=100:11:0::::p11_question_id:232814159006 or send it as an email attachment, search this site for UTL_MAIL or UTL_SMTP