1,4-Naphthoquinone

1,4-Naphthoquinone
	;
Are common
Systematic name	naphthalene-1,4-dione
Chem. formula	C₁₀H₆O₂
Rat formula	C10H6O2
Physical properties
Molar mass	158.153 g / mol
Density	1.42 g / cm³
Thermal properties
T. melt.	128 ℃
T. sub.	<100 ℃
T. aux.	142 ℃
Chemical properties
Solubility in water	0.35 g / 100 ml
Classification
CAS Number
PubChem
ChemSpider
EINECS Number	204-977-6
Chebi	27418
Smiles
	C1 = CC = C2C (= O) C = CC (= O) C2 = C1
Inchi
	1S / C10H6O2 / c11-9-5-6-10 (12) 8-4-2-1-3-7 (8) 9 / h1-6H
Security
MPC	0.1 mg / m 3
LD 50	190 mg / kg (rat, oral)
R phrases	R24 / 25 , R26 , R36 / 37/38 , R43 , R50
S-phrases	S26 , S28 , S36 / 37 , S45 , S61
GHS icons
	Data is provided for standard conditions (25 ℃, 100 kPa) , unless otherwise indicated.

1,4-Naphthoquinone is a derivative of naphthalene , quinone .

Content

Physical Properties

Yellow triclinic crystals with a pungent odor similar to the smell of benzoquinone . Slightly soluble in water, slightly soluble in petroleum ether , soluble in polar organic solvents . In an alkaline environment, it gives a red-brown color. The molecule is planar.

Getting

Gas-phase oxidation of naphthalene using vanadium oxide as a catalyst ^[1] . The main reaction product is phthalic anhydride .

Oxidation of naphthalene by chromium (VI) oxide in acetic acid ^[2] .

Chemical Properties

1,4-naphthoquinone behaves like a strong dienophile in the Diels-Alder reaction . So it reacts with 1,3-butadiene . The reaction is carried out either with an excess of liquefied 1,3-butadiene at room temperature for 45 days, or in the presence of one equivalent of tin (IV) chloride as a catalyst at −50 ° C.

1,4-naphthoquinone behaves like an oxidizing agent , restoring to 1,4-hydroquinone. Gives an oxime . It behaves like a ligand due to the presence of an electrophilic bond (C = C). ^[3]

In acetic acid , when catalyzing I ₂ , chloro or bromine are added, forming 2,3-dihalo-1,4-naphthoquinone. In an alkaline solution, H ₂ O ₂ is oxidized to 2-hydroxy-1,4-naphthoquinone.

Application

It is used for the synthesis of anthraquinone by reaction with 1,3-butadiene and subsequent oxidation, and various dyes, including through nitration to 5-nitro-1,4-naphthoquinone. Corrosion inhibitor. It is used as a catalyst in the production of synthetic rubber and polyacrylates . ^[four]

Notes

↑ Chekalin M.A., Passet B.V., Ioffe B.A. Technology of dyes and intermediates: A manual for technical schools. - 2nd ed., Revised. - L .: Chemistry, 1980 .-- S. 210.
↑ Z. Hauptmann, J. Grefe, H. Reman. Organic chemistry / Transl. with him. P. B. Terentyev, S. S. Churanov, ed. V. M. Potapova. - M .: Chemistry, 1979. - S. 278.
↑ Kündig, EP; Lomberget, T .; Bragg, R .; Poulard, C .; Bernardinelli, G. Desymmetrization of a meso- Diol Complex Derived from [Cr (CO) ₃ (η ⁶ -5.8-Naphthoquinone)]: Use of New Diamine Acylation Catalysts (Eng.) // Chemical Communications : journal. - 2004. - Vol. 2004 , no. 13 . - P. 1548-1549 . - DOI : 10.1039 / b404006f .
↑ I.L. Knunyants. Chemical encyclopedia. - M .: Great Russian Encyclopedia, 1992. - T. 3. - S. 198-199.

[чекалин-1] Chekalin M.A., Passet B.V., Ioffe B.A. Technology of dyes and intermediates: A manual for technical schools. - 2nd ed., Revised. - L .: Chemistry, 1980 .-- S. 210.

[hauptmann-2] Z. Hauptmann, J. Grefe, H. Reman. Organic chemistry / Transl. with him. P. B. Terentyev, S. S. Churanov, ed. V. M. Potapova. - M .: Chemistry, 1979. - S. 278.

[3] Kündig, EP; Lomberget, T .; Bragg, R .; Poulard, C .; Bernardinelli, G. Desymmetrization of a meso- Diol Complex Derived from [Cr (CO) ₃ (η ⁶ -5.8-Naphthoquinone)]: Use of New Diamine Acylation Catalysts (Eng.) // Chemical Communications : journal. - 2004. - Vol. 2004 , no. 13 . - P. 1548-1549 . - DOI : 10.1039 / b404006f .

[энциклопедия-4] I.L. Knunyants. Chemical encyclopedia. - M .: Great Russian Encyclopedia, 1992. - T. 3. - S. 198-199.