Diphenic acid

Structural formula
General
Surname	Diphenic acid
other names	Biphenyl-2,2-dicarboxylic acid 1,1'-biphenyl-2,2'-dicarboxylic acid 2,2'-bibenzoic acid
Molecular formula	C 14 H 10 O 4
Brief description	gray-white powder, monoclinic prisms or plates, needles
External identifiers / databases
CAS number 482-05-3 EC number 207-576-4 ECHA InfoCard 100.006.889 PubChem 10210 Wikidata Q15632900
properties
Molar mass	242.23 g mol −1
Physical state	firmly
density	1.2917 g · cm -3
Melting point	228 ° C
solubility	almost insoluble in water, soluble in organic solvents
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diphenic acid (HOOCC ₆ H ₄ C ₆ H ₄ COOH) is an aromatic chemical compound . The structure consists of two benzene rings , each with a carboxy group  (-COOH) attached in the ortho position . The acid forms an internal anhydride with a seven-membered ring fused to the two benzene rings ; the anhydride has a melting point of 219 ° C.

Extraction and presentation

Diphenic acid can be obtained from anthranilic acid by diazotization and subsequent action of copper (I) ions:

It is also accessible starting from phenanthrene . Here, peroxyacetic acid is first produced from acetic acid and 90% hydrogen peroxide:

${\displaystyle \mathrm {CH_{3}COOH+H_{2}O_{2}\rightleftharpoons CH_{3}COOOH+H_{2}O} }$

This is then implemented with phenanthrene:

${\displaystyle \mathrm {4\ CH_{3}COOOH+C_{14}H_{10}\rightleftharpoons 4\ CH_{3}COOH+C_{14}H_{10}O_{4}} }$

If phenanthrene is treated with oxidizing agents (e.g. hydrogen peroxide , chromium (VI) oxide , potassium dichromate , potassium permanganate ), 9,10-phenanthrenequinone is formed and, through further oxidation, diphenic acid.

If 9,10-phenanthrenequinone is boiled with alcoholic potash , the potassium salt of diphenic acid is formed.

Diphenic acid is also formed by photooxidation from 9,10-phenanthrenequinone.

use

Diphenic acid can be used to produce polyester and alkyd resins .

Individual evidence

1. ↑ ^{a b c} Entry on diphenic acid. In: Römpp Online . Georg Thieme Verlag, accessed on August 7, 2016.
2. ↑ ^{a b c d} Data sheet Diphenic acid from Sigma-Aldrich , accessed on February 24, 2013 ( PDF ).
3. ^ Carl Yaws: Thermophysical Properties of Chemicals and Hydrocarbons. William Andrew, June 20, 2014, ISBN 978-0-323-29060-9 , p. 325.
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 96th edition. (Internet version :), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-48.
5. ^ D'Ans-Lax: paperback for chemists and physicists. 4th edition, Volume 2, Springer Verlag, 1982, ISBN 3-540-12263-X .
6. ^ ER Atkinson, HJ Lawler .: Diphenic Acid In: Organic Syntheses . 7, 1927, p. 30, doi : 10.15227 / orgsyn.007.0030 ; Coll. Vol. 1, 1941, p. 222 ( PDF ).
7. ^ William F. O'Connor, Emil J. Moriconi: 2,2′-Diphenic Acid from Phenanthrene . In: Industrial & Engineering Chemistry . tape 45 , no. 2 , February 1953, p. 277-281 , doi : 10.1021 / ie50518a020 .
8. ^ CR Noller: Textbook of Organic Chemistry. Springer-Verlag, 1960, ISBN 978-3-642-87325-6 , p. 635, doi: 10.1007 / 978-3-642-87324-9
9. ↑ Hans Meyer: Synthesis of the carbon compounds: First part: Open chains and isocycles. Springer-Verlag, 1938, ISBN 978-3-7091-3245-6 , p. 1170.
10. ↑ Gustav Schultz: Die Chemie des Steinkohlentheers: Bd. The raw materials. Friedrich Vieweg and son, 1886.
11. ↑ A. Coehn, G. Jung, J. Daimer: Photochemie and Photographic Chemical Science. Springer Vienna, 1926, ISBN 978-3-7091-5255-3 , p. 136, doi: 10.1007 / 978-3-7091-5403-8
12. ^ Heinz-Gerhard Franck, Jürgen W. Stadelhofer: Industrial aromatic chemistry: Raw materials-process-products. Springer Berlin Heidelberg, 1987, ISBN 978-3-662-07875-4 , p. 377, doi: 10.1007 / 978-3-662-07875-4