Degradation of Guaiacylglycerol-β-Guaiacyl Ether in the Presence of HS­or Polysulphide at Various Alkalinities. Part I. Degradation Rate and the Formation of Enol Ether

The degradation of guaiacylglycerol-β-guaiacyl ether by HS - and polysulphide was studied at various alkalinities between 0.025 M and 1.1 M OH- at 130°C. Polysulphide strongly suppressed the reverse aldol pathway and thereby the formation of enol ether over the whole [OH - ] interval investigated. We therefore conclude that polysulphide increases the fragmentation step and probably also acts as a stronger nucleophile than HS - towards intermediate quinone methide structures during the alkaline treatment of guaiacylglycerol-β-guaiacyl ether. At alkalinities above 0.2M OH - , polysulphide tended to degrade the tested β-model faster than HS - .