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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443936980
| Watchedfields = changed
⚫ | Name = Mellitic acid
⚫ | verifiedrevid = 443938557
⚫ | Reference =<ref></ref>
⚫ | Name = Mellitic acid
⚫ | ImageFile_Ref = {{chemboximage|correct|??}}
⚫ | Reference =<ref>{{dead link|date=January 2018 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
| ImageFile = Mellitic-acid.png | ImageFile = Mellitic-acid.svg
⚫ <!-- | ImageSize = 200px -->
⚫ | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageName =
⚫ | ImageSize = 180
| IUPACName = Benzene-1,2,3,4,5,6-hexacarboxylic acid
| ImageAlt = Skeletal formula
⚫ | OtherNames = Graphitic acid<br />Benzenehexacarboxylic acid
| ImageCaption = ]
⚫ | Section1 = {{Chembox Identifiers
| ImageFileL1 = Mellitic-acid-from-xtal-3D-bs-17.png
⚫ | PubChem = 2334
| ImageSizeL1 = 120
| ImageAltL1 = Ball-and-stick model<ref name="bart"></ref>
| ImageCaptionL1 = ]
| ImageFileR1 = Mellitic-acid-from-xtal-3D-sf.png
| ImageSizeR1 = 120
| ImageAltR1 = Space-filling model
| ImageCaptionR1 = ]
⚫ | PIN = Benzenehexacarboxylic acid
| OtherNames = Graphitic acid
⚫ |Section1={{Chembox Identifiers
⚫ | PubChem = 2334
| InChI = 1/C12H6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20)(H,21,22)(H,23,24) | InChI = 1/C12H6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18/h(H,13,14)(H,15,16)(H,17,18)(H,19,20)(H,21,22)(H,23,24)
| InChIKey = YDSWCNNOKPMOTP-UHFFFAOYAB | InChIKey = YDSWCNNOKPMOTP-UHFFFAOYAB
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YDSWCNNOKPMOTP-UHFFFAOYSA-N | StdInChIKey = YDSWCNNOKPMOTP-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 517-60-2 | CASNo = 517-60-2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P80QSP14DM
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2244 | ChemSpiderID = 2244
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01681 | DrugBank = DB01681
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 41089 | ChEBI = 41089
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1231329
| SMILES = O=C(O)c1c(c(c(c(c1C(=O)O)C(=O)O)C(=O)O)C(=O)O)C(=O)O | SMILES = O=C(O)c1c(c(c(c(c1C(=O)O)C(=O)O)C(=O)O)C(=O)O)C(=O)O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>12</sub>H<sub>6</sub>O<sub>12</sub> | Formula = C<sub>12</sub>H<sub>6</sub>O<sub>12</sub>
| MolarMass = 342.16 g/mol | MolarMass = 342.16 g/mol
| Density = 1.68 g/cm<sup>3</sup>, 2.078 (calc.)<ref name=spider>. ChemSpider.com.</ref> | Density = 1.68 g/cm<sup>3</sup>, 2.078 (calc.)<ref name=spider>. ChemSpider.com.</ref>
| MeltingPt = >300 °C | MeltingPt= >
| MeltingPtC = 300
⚫ | BoilingPt = 678 °C (calc.)<ref name=spider/>
| BoilingPtC = 678
⚫ | pKa=1.40, 2.19, 3.31, 4.78, 5.89, 6.96<ref>Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref>
⚫ | BoilingPt_notes = (calc.)<ref name=spider/>
⚫ | }}
⚫ | pKa =5.0, 2.19, 3.31, 4.78, 5.89, 6.96<ref>Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref>
}} }}
⚫ }}

⚫ '''Mellitic acid''', also called '''graphitic acid''' or '''benzenehexacarboxylic acid''', is an ] first discovered in 1799 by ] in the ] ] (honeystone), which is the ] ] of the acid.<ref>{{cite book | title = Beiträge zur chemischen Kenntniss der Mineralkörper, Band 3 | language = de | url = https://books.google.com/books?id=h-wTAAAAQAAJ&pg=PA114 | page= 114| author1 = Klaproth | year = 1802 }}</ref> It crystallizes in fine silky needles and is soluble in ] and ].


==Structure==
⚫ '''Mellitic acid''', also called '''graphitic acid''' or '''benzenehexacarboxylic acid''', is an ] first discovered in 1799 by ] in the ] ] (honeystone), which is the ] ] of the acid.
The stable ] of this molecule has the carboxylic acid groups rotated out of the plane of the central benzene ring. The molecule adopts a propeller-like conformation in which the tilt of each carboxylic acid group relative to the central benzene ring varies due to intramolecular hydrogen bonding.<ref name="bart">{{cite journal | doi = 10.1107/S0567740868004176 | title = The crystal structure of a modification of hexaphenylbenzene | year = 1968 | last1 = Bart | first1 = J. C. J. | journal = Acta Crystallographica Section B | volume = 24 | issue = 10 | pages = 1277–1287}}</ref>


== Preparation == == Preparation ==
Mellitic acid may be prepared by warming ] with ], boiling off the excess of the ] salt and adding ] to the solution. The ]d ] is filtered off, the ] ]d and the ammonium salt of the acid purified by ]. The ammonium salt is then converted into the ] salt by precipitation with ] and the lead salt decomposed by ]. The acid may also be prepared by the oxidation of pure ], or of hexamethyl ], in the cold, by ] ], or by hot concentrated ].<ref></ref> Mellitic acid may be prepared by warming mellite with ], boiling off the excess of the ] salt, and adding ] to the solution. The ]d ] is filtered off, the ] ]d, and the ammonium salt of the acid purified by ]. The ammonium salt is then converted into the ] salt by precipitation with ], and the lead salt is then decomposed by ]. The acid may also be prepared by the oxidation of pure ], ] or ], by ] ] in the cold, or by hot concentrated ].<ref></ref>


== Reactions == == Reactions ==
It crystallizes in fine silky needles and is soluble in ] and ]. It is a very stable compound, ], concentrated ] and ] having no action upon it. It is decomposed, on dry distillation, into ] and ], C<sub>10</sub>H<sub>6</sub>O<sub>8</sub>; when distilled with ] it gives carbon dioxide and ]. Long digestion of the acid with excess of ] results in the formation of the acid chloride, which crystallizes in needles, melting at 190 °C. By heating the ammonium salt of the acid to 150&ndash;160 °C so long as ammonia is evolved, a mixture of paramide (mellimide), C<sub>6</sub>(CONHCO)<sub>3</sub>, and ] is obtained. The mixture may be separated by dissolving out the ammonium euchroate with water. Paramide is a white amorphous powder, insoluble in water and alcohol. It is a very stable compound; ], concentrated ] and ] do not react with it. It is decomposed, on dry distillation, into ] and ], C<sub>10</sub>H<sub>6</sub>O<sub>8</sub>; when distilled with ] it gives carbon dioxide and benzene. Long digestion of the acid with an excess of ] forms the acid chloride, which crystallizes in needles, and melts at 190&nbsp;°C. By heating the ammonium salt of the acid to 150–160&nbsp;°C while ammonia is evolved, a mixture of paramide (mellimide, molecular formula {{chem|C|6|(CONHCO)|3}}), and ] is obtained. The mixture may be separated by dissolving out the ammonium euchroate with water. Paramide is a white amorphous powder, insoluble in water and alcohol.
]
The high stability of mellitic acid salts and their presence as an endproduct of the oxidation of ]s, which are present in the solar system, make them a possible organic substance in ].<ref>{{cite journal|author1=S. A. Benner |author2=K. G. Devine |author3=L. N. Matveeva |author4=D. H. Powell | year = 2000| title = The missing organic molecules on Mars| journal = ]| volume = 97| issue = 6| pages = 2425–2430| doi = 10.1073/pnas.040539497| pmid = 10706606| pmc = 15945|doi-access=free }}</ref>


⚫ Mellitates (and salts of other ]s) of ] and ] have interesting magnetic properties.<ref>Kurmoo M, Estournes C, Oka Y, Kumagai H, Inoue K (2005) Inorganic Chemistry volume 44, page 217</ref>
The high stability of mellitic acid salts and that they are the endproduct of the oxidation of ]s, which are present in the solar system, made them a possible organic substance in ] soil.<ref>{{cite journal
| author = S. A. Benner, K. G. Devine, L. N. Matveeva, D. H. Powell
| year = 2000
| title = The missing organic molecules on Mars
| journal = ]
| volume = 97
| issue = 6
| pages = 2425–2430
| doi = 10.1073/pnas.040539497
| pmid = 10706606
| pmc = 15945
}}</ref>


== See also ==
⚫ Mellitates (and salts of other ]s) of ] and ] have interesting magnetic properties.<ref>
⚫ * ]
Kurmoo M, Estournes C, Oka Y, Kumagai H, Inoue K (2005) Inorganic Chemistry volume 44, page 217
</ref>

⚫ == Mellitic anhydride ==
{{main|Mellitic anhydride}}


== References == == References ==
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== Further reading == == Further reading ==
Henry Enfield Roscoe, Carl Scholemmer, "Mellitene Group", "'''': ''V.III: The Chemistry of the Hydrocarbons and their Derivatives on Organic Chemistry: P.V'':529. D. Appleton and Co. (1889). Henry Enfield Roscoe, Carl Scholemmer, "Mellitene Group", "'''': ''V.III: The Chemistry of the Hydrocarbons and their Derivatives on Organic Chemistry: P.V'':529. D. Appleton and Co. (1889).


{{EB1911 |wstitle=Mellitic Acid |volume=18 |page=95}}
{{1911}}

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{{DEFAULTSORT:Mellitic Acid}} {{DEFAULTSORT:Mellitic Acid}}
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