PMID- 35725071
OWN - NLM
STAT- MEDLINE
DCOM- 20220622
LR  - 20220622
IS  - 1001-0742 (Print)
IS  - 1001-0742 (Linking)
VI  - 117
DP  - 2022 Jul
TI  - Chlorination of para-substituted phenols: Formation of alpha, beta-unsaturated 
      C(4)-dialdehydes and C(4)-dicarboxylic acids.
PG  - 197-208
LID - S1001-0742(22)00201-7 [pii]
LID - 10.1016/j.jes.2022.04.029 [doi]
AB  - Despite the widespread occurrence of phenols in anthropogenic and natural 
      compounds, their fate in reactions with hypochlorous acid (HOCl), one of the most 
      common water treatment disinfectants, remains incompletely understood. To close 
      this knowledge gap, this study investigated the formation of disinfection 
      by-products (DBPs) in the reaction of free chlorine with seven para-substituted 
      phenols. Based on the chemical structures of the DBPs and the reaction mechanisms 
      leading to their formation, the DBPs were categorized into four groups: 
      chlorophenols, coupling products, substituent reaction products, and ring 
      cleavage products. In contrast to previous studies that investigated the 
      formation of early-stage chlorophenols, the primary focus of this study was on 
      the elucidation of novel ring cleavage products, in particular alpha, beta-unsaturated 
      C(4)-dialdehydes, and C(4)-dicarboxylic acids, which, for the first time, were 
      identified and quantified in this study. The molar yields of 2-butene-1,4-dial 
      (BDA), one of the identified alpha, beta-unsaturated C(4)-dialdehydes, varied among the 
      different phenolic compounds, reaching a maximum value of 10.4% for bisphenol S. 
      Molar yields of 2-chloromaleic acid (Cl-MA), one of the identified 
      C(4)-dicarboxylic acids, reached a maximum value of 30.5% for 
      4-hydroxy-phenylacetic acid under given conditions. 2,4,6-trichlorophenol (TCP) 
      was shown to be an important intermediate of the parent phenols and the C(4)-ring 
      cleavage products. Based on the temporal trends of alpha, beta-unsaturated 
      C(4)-dialdehydes and C(4)-dicarboxylic acids, their formation is likely 
      attributable to two separate ring cleavage pathways. Based on the obtained 
      results, an overall transformation pathway for the reaction of para-substituted 
      phenols with free chlorine leading to the formation of novel C(4) ring cleavage 
      products was proposed.
CI  - Copyright (c) 2022. Published by Elsevier B.V.
FAU - Zhang, Zhuoyue
AU  - Zhang Z
AD  - Department of Environmental Health and Engineering, Johns Hopkins University, 
      Baltimore, MD 21218, USA.
FAU - Prasse, Carsten
AU  - Prasse C
AD  - Department of Environmental Health and Engineering, Johns Hopkins University, 
      Baltimore, MD 21218, USA. Electronic address: cprasse1@jhu.edu.
LA  - eng
PT  - Journal Article
DEP - 20220505
PL  - Netherlands
TA  - J Environ Sci (China)
JT  - Journal of environmental sciences (China)
JID - 100967627
RN  - 0 (Chlorophenols)
RN  - 0 (Dicarboxylic Acids)
RN  - 0 (Disinfectants)
RN  - 0 (Phenols)
RN  - 0 (Water Pollutants, Chemical)
RN  - 4R7X1O2820 (Chlorine)
SB  - IM
MH  - Chlorine/chemistry
MH  - *Chlorophenols/chemistry
MH  - Dicarboxylic Acids
MH  - *Disinfectants/chemistry
MH  - Disinfection/methods
MH  - Halogenation
MH  - Phenols/chemistry
MH  - *Water Pollutants, Chemical/chemistry
MH  - *Water Purification
OTO - NOTNLM
OT  - High-resolution mass spectrometry
OT  - Mass balance
OT  - Quantification
OT  - Ring cleavage products
OT  - Transformation pathways
EDAT- 2022/06/21 06:00
MHDA- 2022/06/23 06:00
CRDT- 2022/06/20 21:03
PHST- 2022/02/21 00:00 [received]
PHST- 2022/04/15 00:00 [revised]
PHST- 2022/04/21 00:00 [accepted]
PHST- 2022/06/20 21:03 [entrez]
PHST- 2022/06/21 06:00 [pubmed]
PHST- 2022/06/23 06:00 [medline]
AID - S1001-0742(22)00201-7 [pii]
AID - 10.1016/j.jes.2022.04.029 [doi]
PST - ppublish
SO  - J Environ Sci (China). 2022 Jul;117:197-208. doi: 10.1016/j.jes.2022.04.029. Epub 
      2022 May 5.