1,2-Dioxetanedione

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477204215

| Name =

| ImageFile = 1,2-Dioxetanedione.svg

| ImageFile1 = File:Chemfm 1 2 dioxetanedione.svg

| ImageSize = 120px

| PIN = 1,2-Dioxetanedione

| OtherNames = Peroxyacid ester

| Section1 = {{Chembox Identifiers

| InChIKey = WYNZXNXFHYJUTE-UHFFFAOYAI

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C2O4/c3-1-2(4)6-5-1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WYNZXNXFHYJUTE-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 26974-08-3

| PubChem = 14833747

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 11535432

| SMILES = O=C1OOC1=O

| InChI = 1/C2O4/c3-1-2(4)6-5-1

}}

| Section2 = {{Chembox Properties

| C=2 | O=4

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

| Section4 =

| Section5 =

| Section6 =

}}

The chemical compound 1,2-dioxetanedione, or 1,2-dioxacyclobutane-3,4-dione, often called peroxyacid ester, is an unstable oxide of carbon (an oxocarbon) with formula C{{sub|2}}O{{sub|4}}. It can be viewed as a double ketone of 1,2-dioxetane (1,2-dioxacyclobutane), or a cyclic dimer of carbon dioxide.Alfred Hassner (1985): Chemistry of Heterocyclic Compounds: Small Ring Heterocycles, Part 3: Oxiranes, Arene Oxides, Oxaziridines, Dioxetanes, Thietanes, Thietes, Thiazetes, and Others, Volume 42. {{ISBN|978-0-471-05624-9}} {{ISBN|978-0-470-18720-3}} John Wiley & Sons.

In ordinary conditions, it quickly decomposes to carbon dioxide (CO{{sub|2}}) even at {{Convert|180|K|C|sigfig=3}}, but can be detected by mass spectrometry and other techniques.{{cite journal|author=Herman F. Cordes|author2=Herbert P. Richter|author3=Carl A. Heller|year=1969|title=Mass spectrometric evidence for the existence of 1,2-dioxetanedione (carbon dioxide dimer). Chemiluminescent intermediate|journal=J. Am. Chem. Soc.|volume=91|issue=25|pages=7209|doi=10.1021/ja01053a065}}

{{cite journal|title=Chemilumineszenz des "Dioxetandions"|trans-title=Chemiluminescence of „Dioxetanedione“|author=J. Stauff|author2=W. Jaeschke|author3=G. Schlögl|year=1972|journal=Z. Naturforsch.|volume=B 27|issue=11|pages=1434–1435|doi=10.1515/znb-1972-1140|s2cid=94708095|doi-access=free|url=http://publikationen.ub.uni-frankfurt.de/files/76112/10.1515_znb-1972-1140.pdf}}

1,2-Dioxetanedione is an intermediate in the chemoluminescent reactions used in glowsticks.{{cite journal|last1=Vacher|first1=Morgane|last2=Fdez. Galván|first2=Ignacio|last3=Ding|first3=Bo-Wen|last4=Schramm|first4=Stefan|last5=Berraud-Pache|first5=Romain|last6=Naumov|first6=Panče|last7=Ferré|first7=Nicolas|last8=Liu|first8=Ya-Jun|last9=Navizet|first9=Isabelle|last10=Roca-Sanjuán|first10=Daniel|last11=Baader|first11=Wilhelm J.|last12=Lindh|first12=Roland|title=Chemi- and Bioluminescence of Cyclic Peroxides|journal=Chemical Reviews|volume=118|issue=15|pages=6927–6974|date=March 2018|doi=10.1021/acs.chemrev.7b00649|pmid=29493234}}{{cite journal | author = Richard Bos | author2 = Neil W. Barnett | author3 = Gail A. Dyson| author4 = Kieran F. Lim | author5 = Richard A. Russell | author6 = Simon P. Watson | name-list-style = amp | year = 2003 | title = Studies on the mechanism of the peroxyoxalate chemiluminescence reaction: Part 1. Confirmation of 1,2-dioxetanedione as an intermediate using 13C nuclear magnetic resonance spectroscopy | journal = Analytica Chimica Acta | volume = 502 | issue = 2 | doi = 10.1016/j.aca.2003.10.014 | pages = 141–147}}

The decomposition proceeds via a paramagnetic oxalate biradical intermediate.{{cite journal | author = Richard Bos | author2 = Sarah A. Tonkin | author3 = Graeme R. Hanson| author4 = Christopher M. Hindson | author5 = Kieran F. Lim | author6 = Neil W. Barnett | name-list-style = amp | year = 2009 | title = In Search of a Chemiluminescence 1,4-Dioxy Biradical | journal = J. Am. Chem. Soc. | volume = 131 | issue = 8 | pages = 2770–2771 | doi = 10.1021/ja808401p | pmid = 19206238}}

It is an intermediate in a reaction (between oxalyl chloride and hydrogen peroxide in ethyl acetate, accumulating in solution at room temperature up to a few micromoles, provided that the activating dye and all traces of metals and other reducing agents are removed from the system, and the reactions are carried out in an inert atmosphere.Luiz F. M. L. Ciscato, Fernando H. Bartoloni, Erick L. Bastos, and Wilhelm J. Baader (2009), Direct Kinetic Observation of the Chemiexcitation Step in Peroxyoxalate Chemiluminescence. Journal of Organic Chemistry, volume 74, 8974–8979. {{doi|10.1021/jo901402k}}.