Diphenic acid

Diphenic acid
Names
	Preferred IUPAC name [1,1′-Biphenyl]-2,2′-dicarboxylic acid
	Other names 2,2'-dibenzoic acid
Identifiers
CAS Number	482-05-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:23837;
ChEMBL	ChEMBL79411;
ChemSpider	9795;
ECHA InfoCard	100.006.889
EC Number	207-576-4;
Gmelin Reference	536420
PubChem CID	10210;
UNII	QY5X735ZIM;
CompTox Dashboard (EPA)	DTXSID0060064 ;
	InChI InChI=1S/C14H10O4/c15-13(16)11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(17)18/h1-8H,(H,15,16)(H,17,18) Key: GWZCCUDJHOGOSO-UHFFFAOYSA-N;
	SMILES C1=CC=C(C(=C1)C2=CC=CC=C2C(=O)O)C(=O)O;
Properties
Chemical formula	C14H10O4
Molar mass	242.230 g·mol−1
Appearance	white solid
Density	1.2917 g/cm3
Melting point	235.5 °C (455.9 °F; 508.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diphenic acid, also known as Dibenzoic acid, is an organic compound with the formula (C₆H₄CO₂H)₂. It is the most studied of several isomeric dicarboxylic acids of biphenyl. It is a white solid that can be prepared in the laboratory from anthranilic acid via the diazonium salt.[1] It is the product of the microbial action on phenanthrene.[2]

The compound forms a variety of coordination polymers.[3] It also exhibits atropisomerism. It can form an internal anhydride featuring a seven-membered ring fused to the two benzene rings.

Preparation

Diphenic acid is prepared from anthranilic acid by diazotization, followed by reduction with copper(I).[4]

It can also be synthesized from the oxidation of phenanthrene by peracetic acid, which is first prepared from acetic acid and 90% hydrogen peroxide:[5]

CH₃COOH + H₂O₂ ⇌ CH₃COOOH + H₂O

4 CH₃COOOH + C₁₄H₁₀ → 4 CH₃COOH + C₁₄H₁₀O₄

Phenanthrene can also be treated with other oxidizing agents (such as hydrogen peroxide, chromium trioxide, potassium dichromate, or potassium permanganate), which first yields phenanthrenequinone and gives diphenic acid on further oxidation.[6][7] Similarly, phenanthrenequinone can be boiled in alcoholic potash (potassium hydroxide in alcohol) to give the potassium salt of diphenic acid,[8] and can alternatively be photo-oxidized to diphenic acid.[9]

References

Atkinson, E. R.; Lawler, H. J. (1927). "Diphenic Acid". Organic Syntheses. 7: 30. doi:10.15227/orgsyn.007.0030.
Moody, J. D.; Freeman, J. P.; Doerge, D. R.; Cerniglia, C. E. (2001). "Degradation of Phenanthrene and Anthracene by Cell Suspensions of Mycobacterium sp. Strain PYR-1". Applied and Environmental Microbiology. 67 (4): 1476–1483. doi:10.1128/AEM.67.4.1476-1483.2001. PMC 92757. PMID 11282593.
Yang, Jin; Ma, Jian-Fang; Liu, Ying-Ying; Ma, Ji-Cheng; Batten, Stuart R. (2009). "A Series of Lead(II) Complexes with π−π Stackings: Structural Diversities by Varying the Ligands". Crystal Growth & Design. 9 (4): 1894–1911. doi:10.1021/cg801085d.
"DIPHENIC ACID". Organic Syntheses. 7: 30. 1927. doi:10.15227/orgsyn.007.0030.
O'Connor, William F.; Moriconi, Emil J. (1953). "2,2′-Diphenic Acid from Phenanthrene". Industrial & Engineering Chemistry. 45 (2): 277–281. doi:10.1021/ie50518a020. ISSN 0019-7866.
Noller, Carl R. (1960), "Kondensierte aromatische Kohlenwasserstoffe und ihre Derivate", Lehrbuch der Organischen Chemie (in German), Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 614–639, doi:10.1007/978-3-642-87324-9_28, ISBN 978-3-642-87325-6, retrieved 2023-03-27
Meyer, Hans (1938). Synthese der Kohlenstoffverbindungen : Erster Teil: Offene Ketten und Isocyclen (in German). Vienna. p. 1170. ISBN 978-3-7091-3245-6. OCLC 913683350.{{cite book}}: CS1 maint: location missing publisher (link)
Gustav, Schultz (1886). Die Chemie des Steinkohlentheers: Bd. Die Rohmaterialen. Friedrich Vieweg und Sohn.
Coehn, A.; Jung, G.; Daimer, J., eds. (1926). Photochemie und Photographische Chemikalienkunde (in German). Vienna: Springer Vienna. p. 136. doi:10.1007/978-3-7091-5403-8. ISBN 978-3-7091-5255-3.

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[1] Atkinson, E. R.; Lawler, H. J. (1927). "Diphenic Acid". Organic Syntheses. 7: 30. doi:10.15227/orgsyn.007.0030.

[2] Moody, J. D.; Freeman, J. P.; Doerge, D. R.; Cerniglia, C. E. (2001). "Degradation of Phenanthrene and Anthracene by Cell Suspensions of Mycobacterium sp. Strain PYR-1". Applied and Environmental Microbiology. 67 (4): 1476–1483. doi:10.1128/AEM.67.4.1476-1483.2001. PMC 92757. PMID 11282593.

[3] Yang, Jin; Ma, Jian-Fang; Liu, Ying-Ying; Ma, Ji-Cheng; Batten, Stuart R. (2009). "A Series of Lead(II) Complexes with π−π Stackings: Structural Diversities by Varying the Ligands". Crystal Growth & Design. 9 (4): 1894–1911. doi:10.1021/cg801085d.

[4] "DIPHENIC ACID". Organic Syntheses. 7: 30. 1927. doi:10.15227/orgsyn.007.0030.

[5] O'Connor, William F.; Moriconi, Emil J. (1953). "2,2′-Diphenic Acid from Phenanthrene". Industrial & Engineering Chemistry. 45 (2): 277–281. doi:10.1021/ie50518a020. ISSN 0019-7866.

[6] Noller, Carl R. (1960), "Kondensierte aromatische Kohlenwasserstoffe und ihre Derivate", Lehrbuch der Organischen Chemie (in German), Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 614–639, doi:10.1007/978-3-642-87324-9_28, ISBN 978-3-642-87325-6, retrieved 2023-03-27

[7] Meyer, Hans (1938). Synthese der Kohlenstoffverbindungen : Erster Teil: Offene Ketten und Isocyclen (in German). Vienna. p. 1170. ISBN 978-3-7091-3245-6. OCLC 913683350.{{cite book}}: CS1 maint: location missing publisher (link)

[8] Gustav, Schultz (1886). Die Chemie des Steinkohlentheers: Bd. Die Rohmaterialen. Friedrich Vieweg und Sohn.

[9] Coehn, A.; Jung, G.; Daimer, J., eds. (1926). Photochemie und Photographische Chemikalienkunde (in German). Vienna: Springer Vienna. p. 136. doi:10.1007/978-3-7091-5403-8. ISBN 978-3-7091-5255-3.