Romance free choice items (FCIs) are frequently pointed out as resulting from the grammaticalization of the relative determiner 
qual ‘which’ and an element derived from a volition verb, such as 
querer ‘want’. Contrary to other Romance FCIs, Portuguese 
qualquer ‘any’ remains understudied, therefore
            
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            Romance free choice items (FCIs) are frequently pointed out as resulting from the grammaticalization of the relative determiner 
qual ‘which’ and an element derived from a volition verb, such as 
querer ‘want’. Contrary to other Romance FCIs, Portuguese 
qualquer ‘any’ remains understudied, therefore motivating the current research. In this article, I investigate the syntax and semantics of 
qualquer, from a diachronic perspective, based on examples extracted from 13th and 14th century texts. Analysis of contexts of occurrence of 
qualquer showed that, in Old Portuguese, the elements 
qual and 
quer could combine in different configurations, corresponding to different structures. On the one hand, the relative determiner 
qual could combine with a form of the volition verb in 
ever free relative clauses. On the other hand, 
qual and 
quer were also combined in appositive relative clauses, which seem to be at the core of postnominal 
qualquer. However, similar to what is argued for Old Spanish, 
qualquer was also a quantifier-like element, occurring in prenominal position and giving rise to universal interpretations. The different origins of prenominal and postnominal 
qualquer may help explain the different readings in contemporary data.
            
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