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Table 6 FIA-MS and HPLC-MS characterization of PPD oxidation products

From: Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Analyte

FIA medium or chromatographic conditions (separation column, eluent composition)

Monoisotopic mass [M + H]+ (amu)

Fragment (amu)

Analytical method

Reference

p-Benzoquinone diimine (BQDI)

Waters Atlantis ACN/ammonium formate pH 7.5

107.06

80 [M-HNC + H]+53 [M-2HNC + H]+ [C4H4 + H+]

HPLC-MS/MS

[49]

 

Fisher Scientific PepMAP Acclaim C18 (75 μm × 15 cm) ACN/0.05 % TFA

107.06

 

HPLC-MS/MS

[3]

 

FIA/NH4Ac (30:70)

107.06

 

EC-ESI-TOF-MS

[25]

SBQDIRC

FIA ACN/NH4Ac (30:70)

108.07 [M]+

 

EC-ESI-TOF-MS

[25]

PPD

Agilent Zorbax SB-C18 (4.6 × 250 mm) methanol/NH4Ac pH 6.9

109.07

 

HPLC-MS/MS

[3]

 

Agilent Zorbax SB-C18 (4.6 × 200 mm) methanol/NH4Ac pH 6.9

109.07

 

HPLC-MS

[2]

 

FIA ACN/NH4Ac (30:70)

109.07

 

EC-ESI-TOF-MS

[25]

 

direct injection

109.07

92.12 [M-NH3 + H]+

MALDI-MS-MS

[78]

Unknown

Waters Xterra MS C18 (4.6 × 150 mm, 5 μm) methanol/NH4Ac, pH 7.2

137

 

HPLC-ESI-MS/MS

[8]

 

Agilent Zorbax SB-C18 (4.6 × 200 mm) methanol/NH4Ac pH 6.9

137

 

HPLC-MS

[2]

4-Aminophenyl formamide

Waters X-Bridge Phenyl (2.1 × 150 mm, 3.5 μm) methanol/NH4Ac, pH 8

137.07

 

HPLC-ESI-MS

[56]

Dimeric oxidation products

Waters Atlantis ACN/ammonium formate pH 7.5

198

 

HPLC-MS/MS

[49]

2-(1,4-Benzoquinone diimine)-1,4-benzoquinone diimine

FIA ACN/NH4Ac (30:70)

211.09

 

EC-ESI-TOF-MS

[25]

2-(1′,4′-Benzoquinone diimine)-4-aminoaniline

FIA ACN/NH4Ac (30:70)

213.11

198.10 [M-NH + H]+183.09 [M-2NH + H]+

EC-ESI-TOF-MS

[25]

Bandrowski’s Base

Waters Atlantis ACN/ammonium formate pH 7.5

319.17

 

HPLC-MS/MS

[49]

 

Zorbax SB-C18 (4.6 × 200 mm) methanol/NH4 Ac pH 6.9

319.17

 

HPLC-MS

[2]

 

Zorbax SB-C18 (4.6 × 250 mm) methanol/NH4Ac pH 6.9

319.17

 

HPLC-MS/MS

[3]

 

FIA ACN/NH4Ac (30:70)

319.17

302.14 [M-NH3 + H]+

EC-ESI-TOF-MS

[25]

  

160.09 [M + 2H]2+

   

Trimeric compounds

Waters Atlantis ACN/ammonium formate pH 7.5

319

 

HPLC-MS/MS

[49]

Tetramer (−NH)

FIA ACN/NH4Ac (30:70)

408.19

 

EC-ESI-TOF-MS

[25]

Tetramer (+O, −NH)

FIA ACN/NH4Ac (30:70)

424.18

 

EC-ESI-TOF-MS

[25]

Pentamer

FIA ACN/NH4Ac (30:70)

529.25

512.23 [M-NH3 + H]+

EC-ESI-TOF-MS

[25]

  

265.13 [M + 2H]2+

   
  1. ACN acetonitrile, FIA flow injection analysis, MALDI matrix-assisted laser desorption ionization, NH 4 Ac ammonium acetate, TFA trifluoroacetic acid