Separation and determination of aniline and substituted anilinesulphonic acid derivatives by ion-pair reversed-phase high-performance liquid chromatography

Spillane, William J.; Lally, John M.; McCormack, K. A.; Kanetani, Fujio

doi:10.1039/an9881300399

Cited by 3 publications

(1 citation statement)

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“…The most convenient approach to resolve a strong amphoteric analyte like 4-ABS on reversed-phase columns should be the technique of ion-pair chromatography (Bastian et al 1994;Spillane et al 1988). Cetyltrimethylammonium (CTMA) as counter-ion in a methanol/water isocratic mobile phase was used successfully (method B).…”

Section: Decolorization Of Ao52 and Detection Of The Amines Dmpd And mentioning

confidence: 99%

Degradation and detoxification of acid orange 52 by Pseudomonas putida mt-2: a laboratory study

Mansour

Ghédira

Barillier

et al. 2011

Environ Sci Pollut Res

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Section: Decolorization Of Ao52 and Detection Of The Amines Dmpd And mentioning

confidence: 99%

Degradation and detoxification of acid orange 52 by Pseudomonas putida mt-2: a laboratory study

Mansour

Ghédira

Barillier

et al. 2011

Environ Sci Pollut Res

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Photoisomerization and photodegradation of metanilic acid

Lally¹,

Spillane²

1991

J. Chem. Soc., Perkin Trans. 2

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The photolysis of metanilic acid (1) as the sodium metanilate, through quartz under helium at h = 254 nm leading to the isomeric anilinesulphonic acids (2 and 3) and anilinei(4) has been studied in water. The effects of p H and solvent on products, the acid-base catalysis of the photoreaction (pHproduct profile) and the effects of substrate concentration, radical scavenging, triplet sensitization and quenching studies are reported.A mechanism involving a single triplet and a series of o-complexes is proposed.Thermal isomerization of orthanilic acid (2) to sulphanilic acid (3) in concentrated sulphuric acid at high temperatures was first reported almost one hundred years ago' and has been the subject of considerable study in recent time^.^.^ Metanilic acid(1) does not isomerize under similar conditions. There are a number of reports on the photochemistry of sulphonic acids and sulphonates & l o and two major reaction pathways have been recognized for arenesulphonic acids or their sodium ~a l t s . ~* ~, ~The primary photochemical process in aqueous solution appears to be C-S bond cleavage via the II,II* excited state, leading to desulphonation and the formation of the corresponding aromatic hydrocarbon [eqn. (l)]. A competing process of desulphonylation leading to the formation of the corresponding phenol, or its quinonoid oxidation products, if oxygen is present, may also occur [eqn. (2)].ArSO, -% ArOSO; -ArO-+ SO2 (2)Desulphonation proceeds via the excited triplet state and desulphon ylation involves an initial rearrangement of the sulphonate to the isomeric sulphite possibily via an oxathiiran intermediate and a singlet excited state. We were not aware of any studies on the photochemistry of aminobenzenesulphonic acids and we decided therefore to examine the photochemistry of metanilic acid as a starting point. * 1 cal = 4.184 J. Quenching Studies.-Stern-Volmer (S-V) plots for the appearance of 2-4 on irradiation of metanilic acid in water Paper 0/03438J

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The photochemistry of para-substituted phenylsulphamates—photo-Fries rearrangements

Lally¹,

Spillane²

1991

J. Chem. Soc., Perkin Trans. 2

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Separation and determination of aniline and substituted anilinesulphonic acid derivatives by ion-pair reversed-phase high-performance liquid chromatography

Cited by 3 publications

References 1 publication

Degradation and detoxification of acid orange 52 by Pseudomonas putida mt-2: a laboratory study

Degradation and detoxification of acid orange 52 by Pseudomonas putida mt-2: a laboratory study

Photoisomerization and photodegradation of metanilic acid

The photochemistry of para-substituted phenylsulphamates—photo-Fries rearrangements

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