simultaneous symmetric and public key encryption ?

[vedaal@hush.ai]

is it possible to symmetrically encrypt to one person, and at the same time encrypt the session key to another person's public key?

i had a situation where 3 of us were working on a pdf, and one person needed to revoke his key, and asked for a symmetrically encrypted file
{i simply sent the encrypted pdf file separately to each one, but needed two encryptions, two e-mails, etc.}

would having the possibility of simultaneously encrypting symmetrically 
and to a public key, 
allow for a vulnerability in being able to crack
the passphrase for the symmetric encryption?

tia,

vedaal



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