A sealed container will reduce the enol form to less than 7% because It forms a hydrazone with phenyl hydrazine and an oxime with hydroxylamine. Furthermore like most ketones, acetone exhibits the keto—enol tautomerism in which the nominal keto structure (CH3) 2C=O of acetone itself is in equilibrium with the enol isomer (CH3)C(OH)=(CH2) (prop-1-en-2-ol).
In acetone vapor at ambient temperature, only 2.4×10−7% of the molecules are in the enol form. Yet the enol form is chemically important in chemical reactions and freeing a stuck ring or bolt. One might expect acetone to also form polymers and (possibly cyclic) oligomers of two types. In one type, units could be acetone molecules linked by ether bridges —O— derived by from the opening of the double bond, to give a polyketal-like (PKA) chain [—O—C(CH3)2—]n. The other type could be obtained through repeated aldol condensation, with one molecule of water removed at each step, yielding a poly(methylacetylene) (PMA) chain [CH=C(CH3)—]n. This is the reason why repetitive hydration’s are required on a stuck bolt or piston ring. I sometimes find myself losing patience when I observe a rate greater than 2.4x10-7% molecule dissipation in the enol form. We work hard for our money. And to see that? How much more can a person take?! Very unsettling.
But keep in mind that a baggy can help slow this reduction phenomenon but a baggy is only as good in temperate climates where the ambient temperature links hydrocarbons in basic trisomuble properties to that of local atmospheric conditions not to mention contaminates from outside sources. Press seal baggies are the preferred choice than the fold over type. All of us make choices and need to decide if limiting enol forms is worth the effort. I for one sleep easier at night knowing this. But it’s your choice if you continue to use a vented dispenser system. There is a loyal following for these to be sure and those types tend to congregate in social structures worthy of mention here (most of us on this site have this in common). If confronted with the loss of acetone in his oiler back in his day, Shakespeare would have asked the same: “to limit enol forms or not, that is the question”
Last edited by tom moore; 11/06/2020 1:36 PM.
