In Present-Day English, the particle out is obligatorily
adjacent to the following of PP, as in He pulled the
plugs out of his ears / *He pulled out the plugs
of his ears, even though particles can normally precede or follow
the object of the particle verb, as in Hepulled out the plugs / Hepulled the plugs out. Interestingly, in Old English and Middle
English, the particle out could occur either adjacent or
nonadjacent to the of PP. Based on corpus data covering the
period from Old English to Late Modern English, I show that the change in the
syntax of directional out of involves grammaticalization: The
bleaching of the directional meaning of the preposition of led
to a structural reanalysis by which the of PP became included
in the particle's phrasal projection and could no longer be separated
from the particle out. This in turn led to phono-logical
reduction of the preposition of. The loss of the nonadjacent
option is argued to be connected to the status of particles as optionally
projecting elements.*