1,4 benzoquinone

Structural formula
General
Surname	1,4 benzoquinone
other names	p -benzoquinone p -Chinon Cyclohexa-2,5-diene-1,4-dione
Molecular formula	C 6 H 4 O 2
Brief description	yellow-brown solid with a pungent odor
External identifiers / databases
CAS number 106-51-4 EC number 203-405-2 ECHA InfoCard 100.003.097 PubChem 4650 Wikidata Q402719
properties
Molar mass	108.10 g mol −1
Physical state	firmly
density	1.32 g cm −3
Melting point	115.7 ° C
Vapor pressure	10 Pa (25 ° C)
solubility	poor in water (10 g l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301 + 331-315-319-335-400 P: 261-273-301 + 310-305 + 351 + 338-311
MAK	DFG : not classified, as there is a suspicion of a carcinogenic effect Switzerland: 0.1 ml m −3 or 0.4 mg m −3
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,4-Benzoquinone , often simply called quinone or benzoquinone , is the parent of the (para) - quinones . It forms yellow crystals with a characteristic, penetrating odor. 1,4-Benzoquinone is formed during the oxidation of hydroquinone and as a metabolic product in humans in benzene poisoning.

history

In studies of the chemistry of from cinchona bark isolated Chinasäure the Russian chemist watched Alexander Abramovich Voskresensky that a yellow, pungent-smelling substance is formed in the oxidation with manganese dioxide (manganese dioxide) in sulfuric acid, which he named "quinolyl".

Since the ending –yl should stand for a radical (radical), Friedrich Wöhler renamed the compound to “quinone”.

Extraction and presentation

The oxidation of hydroquinone in sulfuric acid solution with sodium chlorate (and vanadium pentoxide as catalyst) or with sodium dichromate is possible with high yield.

Biological importance

p -Benzoquinone is blood-damaging and is suspected of causing leukemia . It reacts quickly with biomacromolecules such as proteins and DNA . The adduct with albumin can be detected in broad sections of the population, and this biomarker for quinone (and thus also for benzene ) correlates with car fueling, cigarette consumption , but also with fruit consumption and the use of aspartame . The defense secretion of the bombardier beetle , which is used to ward off predators, contains 1,4-benzoquinone. Bombardier beetles and harvestmen have the ability to produce 1,4-benzoquinone in glands.

Some types of millipedes also produce benzoquinone as a defense against predators. In Madagascar and South America Malagasy: in this context, an unusual observation could be made lemurs and South American capuchin monkey catch and irritate the centipede, so they secrete their benzochinonhaltiges secretions. The monkeys in turn distribute this on their fur, where it unfolds its insect-repellent effect and, in particular, protects against mosquitoes and mosquitoes that transmit disease . The primates obviously accept the psychoactive effect of the secretion benevolently. A selection advantage does not arise because the risk of being eaten during the twenty-minute drug intoxication is significantly increased. It can therefore be assumed that the focus is on inducing intoxication.

use

By reaction with an excess of hydroxylamine , p-benzoquinone dioxime can be obtained.

Web links

Wikibooks: Practical course in organic chemistry / p-benzoquinone by oxidation of hydroquinone with cerium (IV) ammonium nitrate (CAN)  - learning and teaching materials

Individual evidence

1. ↑ ^{a b c d e f g} Entry on p-benzoquinone in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
2. ↑ Data sheet p-Benzoquinone from Sigma-Aldrich , accessed on December 5, 2016 ( PDF ).
3. ↑ Entry on p-benzoquinone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values , accessed on November 2, 2015.
5. ↑ A. Woskressenski : About the composition of quinic acid. In: Annals of Pharmacy. 27, 1838, pp. 257-270, doi : 10.1002 / jlac.18380270303 .
6. ↑ F. Wöhler: Investigations on the quinone. In: Justus Liebigs Annalen der Chemie , 51, 145-163 (1844). doi : 10.1002 / jlac.18440510202 .
7. ↑ HW Underwood, Jr. and WL Walsh: Quinone In: Organic Syntheses . 16, 1936, p. 73, doi : 10.15227 / orgsyn.016.0073 ; Coll. Vol. 2, 1943, p. 553 ( PDF ).
8. ↑ EB Vliet: Quinone In: Organic Syntheses . 2, 1922, p. 85, doi : 10.15227 / orgsyn.002.0085 ; Coll. Vol. 1, 1941, p. 482 ( PDF ).
9. ↑ Lin YS et al .: Variability of albumin adducts of 1,4-benzoquinone, a toxic metabolite of benzene, in human volunteers. Biomarkers . 11/1/2006. Pp. 14-27. PMID 16484134 .
10. ^ Bernhard Klausnitzer: Beetle . Nikol Verlagsgesellschaft mbH & Co. KG, Hamburg 2005, ISBN 3-937872-15-9 .
11. ↑ Jochen Martens, 1978: Weberknechte, Opiliones. The animal world of Germany, part 64. VEB G. Fischer, Jena.
12. ^ "Lemur gets high" video from "Animal Planet" on YouTube, in English
13. ↑ Sebastian Wenger: The happy monkey , 2013, pp. 155–158.
14. ↑ Entry on p-benzoquinone dioxime in the Hazardous Substances Data Bank , accessed on January 2, 2019.
15. ↑ Eberhard Breitmaier, Günther Jung: Organic Chemistry, 7th complete revision. u. exp. Edition 2012 Basics, classes of compounds, reactions, concepts, molecular structure, natural substances, synthesis planning, sustainability . Georg Thieme Verlag, 2014, ISBN 3-13-159987-1 , p. 363 ( limited preview in Google Book search).