1,4-naphthoquinone

Structural formula
General
Surname	1,4-naphthoquinone
other names	alpha-naphthoquinone; 1,4-naphthalenedione; Naphthalene-1,4-dione;
Molecular formula	C 10 H 6 O 2
Brief description	beige solid with a characteristic odor
External identifiers / databases
EC number	204-977-6
ECHA InfoCard	100.004.526
PubChem	8530
Wikidata	Q161542
properties
Molar mass	158.16 g mol −1
Physical state	firmly
density	1.42 g cm −3
Melting point	128.5 ° C
Vapor pressure	2.6 Pa (50 ° C)
solubility	Virtually insoluble in water (0.09 g l −1 at 25 ° C); slightly soluble in alcohol; soluble in benzene, acetic acid and chloroform;
safety instructions
H and P phrases	H: 330-311-301-315-319-317-400
	P: 280-273-309 + 310-302 + 352-304 + 340-305 + 351 + 338
Toxicological data	190 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,4-Naphthoquinone is a chemical compound from the quinone group . It is one of the isomeric naphthoquinones to which z. B. also include 1,2-naphthoquinone and 2,6-naphthoquinone .

Biological importance

1,4-naphthoquinone or its derivative menadione (2-methyl-1,4-naphthoquinone) forms the basic structure of the various vitamin K compounds .

Extraction and presentation

1,4-Naphthoquinone can be obtained by catalytic gas-phase oxidation of naphthalene . The preparation by oxidation of 1,4-aminonaphthol , 1,4-diaminonaphthalene or 1-naphthylamine-4-sulfonic acid is also possible.

properties

1,4-Naphthoquinone is a light- and air-sensitive, brownish-green solid with a characteristic odor. It begins to sublime at temperatures below 100 ° C and decomposes at higher temperatures, producing carbon monoxide and carbon dioxide .

use

1,4-Naphthoquinone is used as a hardener for photochemically crosslinkable polyesters and for the production of polyester resins, fungicides , algae control agents and antioxidants. It serves as an intermediate for the production of anthraquinone , anthraquinone derivatives and vat dyes , as a polymerization regulator in the production of synthetic rubber and polyacrylates and as a corrosion inhibitor.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,4-naphthoquinone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ International Chemical Safety Card (ICSC) for 1,4-naphthoquinone at the National Institute for Occupational Safety and Health (NIOSH), accessed December 5, 2016.
↑ ^a ^b ^c ^d Toxicological assessment of 1,4-naphthoquinone (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
↑ Louis F. Fieser: 1,4-Naphthoquinone In: Organic Syntheses . 5, 1925, p. 79, doi : 10.15227 / orgsyn.005.0079 ; Coll. Vol. 1, 1941, p. 383 ( PDF ).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,4-naphthoquinone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[2] International Chemical Safety Card (ICSC) for 1,4-naphthoquinone at the National Institute for Occupational Safety and Health (NIOSH), accessed December 5, 2016.

[bg-3] Toxicological assessment of 1,4-naphthoquinone (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.

[4] Louis F. Fieser: 1,4-Naphthoquinone In: Organic Syntheses . 5, 1925, p. 79, doi : 10.15227 / orgsyn.005.0079 ; Coll. Vol. 1, 1941, p. 383 ( PDF ).