The oxidation of naphthalene (1) (Scheme 1) in dichloromethane or acetonitrile with excess ozone gives phthalic aldehyde (3), 2-formyl benzoic acid (4) and phthalic anhydride (8). Small amounts of the (E)- and (Z)-isomer of 3-phenyl-(2-formyl)-propenal (10) and (11) are also observed in some cases. The reaction is faster in acetonitrile than in dichloromethane owing to the higher solubility of ozone in the former solvent. The reaction is faster on lowering the temperature because of the increase of the concentration of ozone in solution at lower temperature. With a 1:1 or a 1:2 naphthalene:ozone ratio high conversion and low selectivity for the anhydride (8) is observed.

Rindone, B., Saliu, F., & Suarez Bertoa, R. (2010). The Synthesis of Phthalic Anhydride via Ozonation of Naphthalene. OZONE: SCIENCE & ENGINEERING, 32(3), 161-165 [10.1080/01919511003788001].

The synthesis of phthalic anhydride via ozonation of naphthalene

RINDONE, BRUNO
;
SALIU, FRANCESCO;SUAREZ BERTOA, RICARDO
2010

Abstract

The oxidation of naphthalene (1) (Scheme 1) in dichloromethane or acetonitrile with excess ozone gives phthalic aldehyde (3), 2-formyl benzoic acid (4) and phthalic anhydride (8). Small amounts of the (E)- and (Z)-isomer of 3-phenyl-(2-formyl)-propenal (10) and (11) are also observed in some cases. The reaction is faster in acetonitrile than in dichloromethane owing to the higher solubility of ozone in the former solvent. The reaction is faster on lowering the temperature because of the increase of the concentration of ozone in solution at lower temperature. With a 1:1 or a 1:2 naphthalene:ozone ratio high conversion and low selectivity for the anhydride (8) is observed.
Articolo in rivista - Articolo scientifico
Chemical Synthesis; Naphthalene; Oxidation; Ozone; Phthalic Anhydride;
English
161
165
5
Rindone, B., Saliu, F., & Suarez Bertoa, R. (2010). The Synthesis of Phthalic Anhydride via Ozonation of Naphthalene. OZONE: SCIENCE & ENGINEERING, 32(3), 161-165 [10.1080/01919511003788001].
Rindone, B; Saliu, F; SUAREZ BERTOA, R
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/17854
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