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Diphenyl oxalate (trademark name Cyalume) is a solid whose oxidation products are responsible for the chemiluminescence in a glowstick. This chemical is the double ester of phenol with oxalic acid. Upon reaction with hydrogen peroxide, 1,2-dioxetanedione is formed, along with release of the two phenols. The dioxetanedione then reacts with a dye molecule, decomposing to form carbon dioxide and leaving the dye in an excited state. As the dye relaxes back to its unexcited state, it releases a photon of visible light. The following colors can be produced by using different dyes:

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dbo:abstract
  • Oxalsäurediphenylester ist eine chemische Verbindung aus der Gruppe der Oxalate. (de)
  • Dufenila oksalato aŭ C14H10O4 estas organika aromata kombinaĵo apartenanta al la funkcia grupo de la esteroj, oleeca flaveca-verda likvaĵo grava pro la kemia lumigo uzata en neonaj braceletoj. La reakcio plej grava okazas en ĉeesto de hidrogena peroksido kie la dufenila oksalato produktas fenolon kaj 1,2-dioksi-etanoduketonon, kiu ekscitigas la tinkturon kaj liberigas kolorajn fotonojn dum produktado de karbona dioksido. La malsupra skizo resumas la reakcion: (eo)
  • Diphenyl oxalate (trademark name Cyalume) is a solid whose oxidation products are responsible for the chemiluminescence in a glowstick. This chemical is the double ester of phenol with oxalic acid. Upon reaction with hydrogen peroxide, 1,2-dioxetanedione is formed, along with release of the two phenols. The dioxetanedione then reacts with a dye molecule, decomposing to form carbon dioxide and leaving the dye in an excited state. As the dye relaxes back to its unexcited state, it releases a photon of visible light. The reaction rate is pH dependent, and slightly alkaline conditions, achieved by adding a weak base, such as sodium salicylate, give a faster reaction and therefore produce brighter light.The 2,4,6-trichlorophenol ester is a solid and thus easier to handle. Furthermore, since trichlorophenolate is the better leaving group, the reaction will proceed faster, again producing brighter light, as compared to the phenol ester. The following colors can be produced by using different dyes: (en)
  • L'oxalate de diphényle, aussi appelé commercialement cyalume est un composé organique de la famille des oxalates, de formule (C6H5O2C)2. C'est le diester de phényle de l'acide oxalique. (fr)
  • 다이페닐 옥살레이트(상명 시알륨)는 야광복 속에서 에 반응성이 있는 고체에스터의 산화물이다. 페놀과 옥살산에 의한 에스터화를 통해 합성될 수 있다. 다이페닐 옥살레이트는 과산화수소와 반응하며 아래의 광자 형성과정을 겪는다. 반응속도는 pH에 의존하고, 약산성 환경에서 과 같은 약염기를 더하면 더 밝은 빛을 얻을 수 있다. 옥살산의 트라이클로로페놀 에스터는 고체이고 다루기 매우 쉽다. 더욱이 는 와 비교했을 때, 바닥상태로 떨어지기 쉬워 반응이 빠를 것이며 더 밝은 빛을 낸다. (ko)
  • Difenyloxalaat is een organische verbinding met als brutoformule C14H10O4. Het is de difenylester van oxaalzuur. Difenyloxalaat is een vaste stof. (nl)
  • シュウ酸ジフェニル(しゅうさんジフェニル、diphenyl oxalate)は、シュウ酸にフェニル基が2つ結合した構造を持つ有機化合物である。ジエステルの一種。シュウ酸ジフェニルまたはその誘導体は、ケミカルライト(冷光)などの化学発光に使われる有名な化合物群である。 (ja)
dbo:alternativeName
  • diphenylethandioate, oxalic acid diphenyl ester, cyalume, DPO (en)
dbo:iupacName
  • Diphenyl oxalate (en)
dbo:thumbnail
dbo:wikiPageID
  • 4000447 (xsd:integer)
dbo:wikiPageLength
  • 3881 (xsd:nonNegativeInteger)
dbo:wikiPageRevisionID
  • 1106101529 (xsd:integer)
dbo:wikiPageWikiLink
dbp:date
  • February 2019 (en)
dbp:imagealt
  • Ball-and-stick model of the diphenyl oxalate molecule (en)
  • Skeletal formula of diphenyl oxalate (en)
dbp:imagefile
  • Diphenyl oxalate 3D ball.png (en)
  • Phenyl oxalate ester.png (en)
dbp:imagesize
  • 220 (xsd:integer)
dbp:othernames
  • diphenylethandioate, oxalic acid diphenyl ester, cyalume, DPO (en)
dbp:pin
  • Diphenyl oxalate (en)
dbp:reason
  • the diphenyl itself is also a solid (en)
dbp:verifiedfields
  • changed (en)
dbp:verifiedrevid
  • 447061584 (xsd:integer)
dbp:watchedfields
  • changed (en)
dbp:wikiPageUsesTemplate
dcterms:subject
gold:hypernym
rdf:type
rdfs:comment
  • Oxalsäurediphenylester ist eine chemische Verbindung aus der Gruppe der Oxalate. (de)
  • Dufenila oksalato aŭ C14H10O4 estas organika aromata kombinaĵo apartenanta al la funkcia grupo de la esteroj, oleeca flaveca-verda likvaĵo grava pro la kemia lumigo uzata en neonaj braceletoj. La reakcio plej grava okazas en ĉeesto de hidrogena peroksido kie la dufenila oksalato produktas fenolon kaj 1,2-dioksi-etanoduketonon, kiu ekscitigas la tinkturon kaj liberigas kolorajn fotonojn dum produktado de karbona dioksido. La malsupra skizo resumas la reakcion: (eo)
  • L'oxalate de diphényle, aussi appelé commercialement cyalume est un composé organique de la famille des oxalates, de formule (C6H5O2C)2. C'est le diester de phényle de l'acide oxalique. (fr)
  • 다이페닐 옥살레이트(상명 시알륨)는 야광복 속에서 에 반응성이 있는 고체에스터의 산화물이다. 페놀과 옥살산에 의한 에스터화를 통해 합성될 수 있다. 다이페닐 옥살레이트는 과산화수소와 반응하며 아래의 광자 형성과정을 겪는다. 반응속도는 pH에 의존하고, 약산성 환경에서 과 같은 약염기를 더하면 더 밝은 빛을 얻을 수 있다. 옥살산의 트라이클로로페놀 에스터는 고체이고 다루기 매우 쉽다. 더욱이 는 와 비교했을 때, 바닥상태로 떨어지기 쉬워 반응이 빠를 것이며 더 밝은 빛을 낸다. (ko)
  • Difenyloxalaat is een organische verbinding met als brutoformule C14H10O4. Het is de difenylester van oxaalzuur. Difenyloxalaat is een vaste stof. (nl)
  • シュウ酸ジフェニル(しゅうさんジフェニル、diphenyl oxalate)は、シュウ酸にフェニル基が2つ結合した構造を持つ有機化合物である。ジエステルの一種。シュウ酸ジフェニルまたはその誘導体は、ケミカルライト(冷光)などの化学発光に使われる有名な化合物群である。 (ja)
  • Diphenyl oxalate (trademark name Cyalume) is a solid whose oxidation products are responsible for the chemiluminescence in a glowstick. This chemical is the double ester of phenol with oxalic acid. Upon reaction with hydrogen peroxide, 1,2-dioxetanedione is formed, along with release of the two phenols. The dioxetanedione then reacts with a dye molecule, decomposing to form carbon dioxide and leaving the dye in an excited state. As the dye relaxes back to its unexcited state, it releases a photon of visible light. The following colors can be produced by using different dyes: (en)
rdfs:label
  • Diphenyl oxalate (en)
  • Oxalsäurediphenylester (de)
  • Dufenila oksalato (eo)
  • Oxalate de diphényle (fr)
  • 다이페닐 옥살레이트 (ko)
  • シュウ酸ジフェニル (ja)
  • Difenyloxalaat (nl)
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