1823, perhaps in some senses from French entitlement, which was in Old French as "title (of a book), inscription," and later was used in legal language; but also in part a native formation from entitle + -ment. Entitlement culture attested by 1994 (culture of entitlement is from 1989).
entitlements make up the major part of the federal budget
enticement
entire
entirely
entirety
entitle
entitlement
entity
ento-
entomb
entombment
entomolite