abacus: That is probably because the main product from the performic oxidation is not the plain glycol, but isosafrole glycol monoformate (formic acid ester of the glycol), see
Post 250865
(Ritter: "buffered performic -> monoformyl glycol", Chemistry Discourse). The reason that free glycol is the solid that collects in the reciever is likely due to the following reasons:
* The isosafrole glycol monoformate is thermally decomposed to the glycol during distillation
* Isosafrole glycol is less reactive than isosafrole glycol monoformate in the H
2SO
4 rearrangement, thus this compound is the one that is predominantly found unreacted after an incomplete H
2SO
4 rearrangement, see
Post 99146 (missing)
(Ritter: "isosafrole glycol less reactive than its formate", Chemistry Discourse).
GC_MS: I do not doubt that polymerization occurs, but I do not think that these products will distill in the range observed for the glycol in a relatively pure form, as well as solidify in the condenser just like predicted for the glycol.
I am very interested in your references, particularly the Ind. J. Chem article, could you post it? The Berichte article I can fetch myself, and I have the "Friedel-Crafts and related reactions" book series on the attic, so I can get that tomorrow.