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Sometimes I see two prepositions together in Esperanto (something I don’t know from other languages). A couple of examples taken from PMEG:

Kien ajn la luno povis lumi tra inter la arboj, li vidis plej ĉarmajn malgrandajn elfojn.

El inter la branĉoj ili sonigas sian voĉon. (pri birdoj)

Of course, strings of three prepositions or more would be difficult for a speaker to decode. A constructed example: Ili ekkuris el antaŭ sub la arboj.

Are there any examples from literature of more than two prepositions in a row? Is there, in theory, no upper limit?

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Prepositions usually occur in front of a noun phrase, so the only way there can be more than one in a row is if the noun phrase itself is a prepositional phrase, as in the example He looked up from under the table, where under the table is the location that is the complement of from. Note that up here is not a preposition but a particle belonging to look up.

It might be possible to have contrived sentences where a large number of prepositional phrases are nested that way. However, it has been an old battle in linguistics to distinguish between what is possible from what occurs in reality, the Chomskyan competence vs performance distinction. So it might theoretically be possible to have an unlimited number of prepositions in a row, in reality there will rarely be more than two, and maybe three of four in contrived sentences.

The same reasoning applies to embeddings (The mouse that the cat that the dog that the boar that the man hunted attacked chased killed died.), where you can come up with really difficult and hard to understand sentences, which nobody in their right mind would ever say (apart from the authors of linguistics papers!), but which are nevertheless grammatically correct, as grammars don't usually put numerical limits on the number of relative clauses or prepositional phrases you can string together.

So my answer is: in theory, everything is possible, but it doesn't happen in practice apart from exceptional cases.

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Wouldn't your second example naturally be expressed by a double preposition construction in English? ("The birds made their voice heard from between the branches.") Or an even more common English example: it came from under there. (I could even readily imagine someone tacking them on in trying to make a location clear: "from under behind where the...")

This doesn't seem particularly odd to me in English or Esperanto, though usually when it occurs both prepositions are serving different functions. For example: "We need to plan for after tomorrow," where "after tomorrow" obliquely names a time for which one could prepare. "Over by" is also a common English construction (as in "put it over by the couch", though I don't know what to make of that - you could argue there's an elided "there" after the over.

I don't suppose Esperanto has an upper limit any more or less than English - I imagine such constructions are comparably similar in both languages.

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    Double prepositions are also very common in Slavic languages. They are less often, but still common in German. I can't, however, recall examples with three or more prepositions in a row in any language I know. So two could be the maximum of complexity that is generally tolerated. May 18 '17 at 7:19

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