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{{Chembox
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| ImageFile = Malonic anhydride.png
| ImageFile = Malonic anhydride.png
| ImageSize = 190px
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| ImageSize1 = 190px
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| ImageName1 = Ball-and-stick model
| ImageName1 = Ball-and-stick model
| IUPACName = Oxetane-2,4-dione
| = Oxetane-2,4-dione
| OtherNames = Malonic anhydride
| OtherNames = Malonic anhydride
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8351595
| ChemSpiderID = 8351595
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KKHUSADXXDNRPW-UHFFFAOYSA-N
| StdInChIKey = KKHUSADXXDNRPW-UHFFFAOYSA-N
| CASNo =
| CASNo =
| CASNo_Ref = {{Cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V8PB6RYA8G
| PubChem = 10176090
| PubChem = 10176090
| SMILES = O=C1OC(=O)C1
| SMILES = O=C1OC(=O)C1
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=3|H=2|O=3
| C=3|H=2|O=3
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| Section3 = {{Chembox Hazards
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'''Malonic anhydride''' or '''oxetane-2,4-dione''' is an [[organic compound]] with [[chemical formula]] C<sub>3</sub>H<sub>2</sub>O<sub>3</sub> or CH<sub>2</sub>(CO)<sub>2</sub>O. It can be viewed as the [[anhydride]] of [[malonic acid]], or a double [[ketone]] of [[oxetane]].
'''Malonic anhydride''' or '''oxetane-2,4-dione''' is an [[organic compound]] with [[chemical formula]] C<sub>3</sub>H<sub>2</sub>O<sub>3</sub> or CH<sub>2</sub>(CO)<sub>2</sub>O. It can be viewed as the [[anhydride]] of [[malonic acid]], or a double [[ketone]] of [[oxetane]].


Malonic anhydride was first synthesized in 1988 by [[ozonolysis]] of [[diketene]].<ref>Cotton, F. A.; Wilkinson, G. (1988) ''Advanced Inorganic Chemistry'', 5th edn. Wiley</ref><ref>{{cite journal| title = Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides| author= H. Mark Perks and Joel F. Liebman| journal= Structural Chemistry | year = 2000| pages = 265–269| volume = 11| issue = 4 | doi = 10.1023/A:1009270411806| s2cid= 92816468| issn = 1040-0400}}</ref> Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known.<ref>Charles L. Perrin; Arrhenius, T (1978). J. Am. Chem. SOC. volume 100, pages 5249-5251.</ref><ref>Ribeiro da Silva, M. A. J.; Monte, M. J. S.; Ribeiro, J. R.(1999) ''J. Chem.Thermodyn.'' 31, 1093.</ref><ref>Charles L. Perrin, Douglas Magde, Sylvia J. Berens, Julie Roque (1980), ''Raman spectrum of a malonic anhydride''. (Actually, of 3,3-dimethyl-oxetane-2,4-dione.) J. Org. Chem., volume 45 issue 9, pp 1705–1706. {{doi|10.1021/jo01297a044}}.</ref>
Malonic anhydride was first synthesized in 1988 by [[ozonolysis]] of [[diketene]].<ref>
Cotton, F. A.; Wilkinson, G. (1988) ''Advanced Inorganic Chemistry'', 5th edn. Wiley
</ref><ref>
{{cite journal
| title = Paradigms and Paradoxes: Aspects of the Energetics of Carboxylic Acids and Their Anhydrides
| author= H. Mark Perks and Joel F. Liebman
| journal= Structural Chemistry
| year = 2000
| pages = 265269
| volume = 11
| issue = 4
| doi = 10.1023/A:1009270411806
| issn = 1040-0400
}}
</ref> Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known.<ref>
Charles L. Perrin; Arrhenius, T (1978). J. Am. Chem. SOC. volume 100, pages 5249-5251.
</ref><ref>
Ribeiro da Silva, M. A. J.; Monte, M. J. S.; Ribeiro, J. R.(1999) ''J. Chem.Thermodyn.'' 31, 1093.
</ref><ref>
Charles L. Perrin, Douglas Magde, Sylvia J. Berens, Julie Roque (1980), ''Raman spectrum of a malonic anhydride''. (Actually, of 3,3-dimethyl-oxetane-2,4-dione.) J. Org. Chem., volume 45 issue 9, pp 1705–1706. DOI: 10.1021/jo01297a044.
</ref>

==References==
{{Reflist}}


==See also==
==See also==
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* [[3-oxetanone]]
* [[3-oxetanone]]


==References==
[[Category:Acid anhydrides]]
<references />

[[Category: anhydrides]]
[[Category:Oxetanes]]
[[Category:Oxetanes]]
[[Category:Substances discovered in the 1980s]]

[[fr:Anhydride malonique]]
[[hu:Malonsav-anhidrid]]
[[pt:Anidrido malônico]]