1,2-Dioxetanedione
Encyclopedia
The chemical
Chemistry
Chemistry is the science of matter, especially its chemical reactions, but also its composition, structure and properties. Chemistry is concerned with atoms and their interactions with other atoms, and particularly with the properties of chemical bonds....

 compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide
Oxide
An oxide is a chemical compound that contains at least one oxygen atom in its chemical formula. Metal oxides typically contain an anion of oxygen in the oxidation state of −2....

 of carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 (an oxocarbon
Oxocarbon
An oxocarbon or oxide of carbon is an inorganic compound consisting only of carbon and oxygen.The simplest and most common oxocarbons are carbon monoxide and carbon dioxide...

) with formula C2O4. It can be viewed as a double ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.

In ordinary conditions, it quickly decomposes to carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...

 (CO2) even at 180 kelvin (-93.2 °C), but can be detected by mass spectrometry
Mass spectrometry
Mass spectrometry is an analytical technique that measures the mass-to-charge ratio of charged particles.It is used for determining masses of particles, for determining the elemental composition of a sample or molecule, and for elucidating the chemical structures of molecules, such as peptides and...

 and other techniques.

1,2-Dioxetanedione is an intermediate in the chemoluminescent
Chemoluminescence
Chemiluminescence is the emission of light with limited emission of heat , as the result of a chemical reaction...

 reaction
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...

s used in glowsticks. The decomposition proceeds via a paramagnetic oxalate
Oxalate
Oxalate , is the dianion with formula C2O42− also written 22−. Either name is often used for derivatives, such as disodium oxalate, 2C2O42−, or an ester of oxalic acid Oxalate (IUPAC: ethanedioate), is the dianion with formula C2O42− also written (COO)22−. Either...

 biradical intermediate.

Recently it has been found that a high-energy intermediate in one of these reactions (between oxalyl chloride
Oxalyl chloride
Oxalyl chloride or ethanedioyl dichloride is a chemical compound with the formula 2. This colourless, sharp-smelling liquid, the diacid chloride of oxalic acid, is a useful reagent in organic synthesis...

 and hydrogen peroxide
Hydrogen peroxide
Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...

 in ethyl acetate
Ethyl acetate
Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and cigarettes...

), which is presumed to be 1,2-dioxetanedione, can accumulate in solution at room temperature (up to a few micromoles at least), provided that the activating dye
Dye
A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and requires a mordant to improve the fastness of the dye on the fiber....

 and all traces of metals and other reducing agents are removed from the system, and the rections are carried out in an inert atmosphere.
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