TY - JOUR

T1 - Wavelength-dependent photochemistry of acetaminophen in aqueous solutions

AU - Pozdnyakov, Ivan P.

AU - Zhang, Xu

AU - Maksimova, Tatiana A.

AU - Yanshole, Vadim V.

AU - Wu, Feng

AU - Grivin, Vjacheslav P.

AU - Plyusnin, Victor F.

N1 - Funding Information: The work was financially supported by Russian Foundation for Fundamental Research (Grants 11-03-00268 , 12-03-00482 , 12-03-91153-GFEN ), NSFC-RFBR Grants ( 21211120159 and 21281220200 ), National Natural Science Foundation of China (Grant No. 21207104 ), Natural Science Foundation of Hubei Province ( 2011CDB274 ) and the Youth Chenguang Project of Science and Technology of Wuhan City ( 2013070104010009 ).

PY - 2014/1/30

Y1 - 2014/1/30

N2 - The influence of irradiation wavelength and intensity on photochemistry of acetaminophen (APAP) in aqueous solution was investigated by combination of steady-state and laser flash photolysis as well as HPLC and LC-MS. Steady-state irradiation at 254 nm leads to APAP disappearance with the quantum yield 0.0014 and to formation of 1-(2-amino-5-hydroxyphenyl)ethanone (P1) as a main primary photo-Fries product. In opposite the laser excitation at 266 nm leads predominantly to two-photon ionization of APAP with the quantum yield 0.013 (I = 70 mJ/cm2) and to the formation of one main product of phenoxyl radical reactions - N-(3,4-dihydroxyphenyl)acetamide (P5). Steady-state excitation at 282 nm leads to both P1 and P5 products formation indicating competition of photo-Fries and photoionization processes. The wavelength-dependent mechanism of APAP photolysis is proposed and discussed.

AB - The influence of irradiation wavelength and intensity on photochemistry of acetaminophen (APAP) in aqueous solution was investigated by combination of steady-state and laser flash photolysis as well as HPLC and LC-MS. Steady-state irradiation at 254 nm leads to APAP disappearance with the quantum yield 0.0014 and to formation of 1-(2-amino-5-hydroxyphenyl)ethanone (P1) as a main primary photo-Fries product. In opposite the laser excitation at 266 nm leads predominantly to two-photon ionization of APAP with the quantum yield 0.013 (I = 70 mJ/cm2) and to the formation of one main product of phenoxyl radical reactions - N-(3,4-dihydroxyphenyl)acetamide (P5). Steady-state excitation at 282 nm leads to both P1 and P5 products formation indicating competition of photo-Fries and photoionization processes. The wavelength-dependent mechanism of APAP photolysis is proposed and discussed.

KW - Acetaminophen

KW - Phenoxyl radical

KW - Photo-Fries reaction

KW - Photodegradation

KW - Photoionization

KW - Water treatment

UR - http://www.scopus.com/inward/record.url?scp=84887133074&partnerID=8YFLogxK

U2 - 10.1016/j.jphotochem.2013.10.006

DO - 10.1016/j.jphotochem.2013.10.006

M3 - Article

AN - SCOPUS:84887133074

VL - 274

SP - 117

EP - 123

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

SN - 1010-6030

ER -