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Charge-transfer complexes of oxygen and polystyrene phenyl groups absorb light to form singlet oxygen, which acts as a radical initiator. [23] Carbonyl impurities in the polymer (c.f. acetophenone) also absorb light in the near ultraviolet range (300 to 400 nm), forming excited ketones able to abstract hydrogen atoms directly from the polymer. [24]
The main polycarbonate material is produced by the reaction of bisphenol A (BPA) and phosgene COCl 2. The overall reaction can be written as follows: The first step of the synthesis involves treatment of bisphenol A with sodium hydroxide, which deprotonates the hydroxyl groups of the bisphenol A. [6] (HOC 6 H 4) 2 CMe 2 + 2 NaOH → Na 2 (OC 6 ...
A polycarbonate is an oxocarbon dianion consisting of a chain of carbonate units, where successive carbonyl groups are directly linked to each other by shared additional oxygen atoms. That is, they are the conjugate bases of polycarbonic acids , the conceptual anhydrides of carbonic acid , or polymers of carbon dioxide .
The Schenck ene reaction or the Schenk reaction is the reaction of singlet oxygen with alkenes to yield hydroperoxides. The hydroperoxides can be reduced to allylic alcohols or eliminate to form unsaturated carbonyl compounds. It is a type II photooxygenation reaction, and is discovered in 1944 by Günther Otto Schenck. [1]
Phenols react similarly. Polycarbonate derived from bisphenol A is produced in this manner. This process is high yielding. However, toxic phosgene is used, and stoichiometric quantities of base (e.g. pyridine) are required to neutralize the hydrogen chloride that is cogenerated. [2] [3] Chloroformate esters are intermediates in this process.
These alkyl radicals react very rapidly with molecular oxygen (rate constants ≈ 10 7 –10 9 mol –1 s –1) to give peroxy radicals, [8] which in turn abstract hydrogen from a fresh section of polymer in a chain propagation step to give new alkyl radicals.
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The Tsuji-Trost reaction was first introduced in 1962. This method played an important role in the synthesis of diallyl carbonate. The first mention of its commercial production dates back to 1982, when Tokuyama Corporation synthesized it for the first time using the sodium carbonate method.