Glycolide (1,4-dioxane-2,5-dione) is a
dimer of
glycolic acid
Glycolic acid (or hydroxyacetic acid; chemical formula ) is a colorless, odorless and hygroscopic crystal, crystalline solid, highly solubility, soluble in water. It is used in various skin care, skin-care products. Glycolic acid is widespread in ...
. Its structure is six-membered ring containing two
lactone
Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated.
Lactones are formed by lactonization, the intramolecular esterification of the corresp ...
s, an
oxidized
Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
variant of
''p''-dioxane. The compound can be synthesized from glycolic acid, via a high-temperature
oligomer
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
ization to form
polyglycolide
Polyglycolide or poly(glycolic acid) (PGA), also spelled as polyglycolic acid, is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. It can be prepared starting from glycolic acid by means of polycondensation or ...
followed by a
depolymerization process. A more direct method is by self-condensation of the
sodium salt of
chloroacetic acid
Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula . This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds are dichlo ...
. It is useful as a starting material for the production of polyglycolide.
References
Dimers (chemistry)
Lactones
Dioxanes
{{organic-compound-stub