Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds.
Identifieur interne : 000C15 ( PubMed/Checkpoint ); précédent : 000C14; suivant : 000C16Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds.
Auteurs : Maolida Nihemaiti [Australie] ; Julien Le Roux [France] ; Christiane Hoppe-Jones [États-Unis] ; David A. Reckhow [États-Unis] ; Jean-Philippe Croué [Australie]Source :
- Environmental science & technology [ 1520-5851 ] ; 2017.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Chloramines, Disinfectants, Nitrogen.
- Disinfection, Halogenation, Water Pollutants, Chemical, Water Purification.
Abstract
The potential formation of nitrogenous disinfection byproducts (N-DBPs) was investigated from the chloramination of nitrogenous and non-nitrogenous aromatic compounds. All molecules led to the formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production yields. Resorcinol, a major precursor of chloroform, also formed di/trichloroacetonitrile, di/trichloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and fragmentation patterns from electronic impact and positive chemical ionization modes, several products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were structurally similar to the heterocyclic compounds formed during chlorination, such as the highly mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic compounds is reported from chloramination process. The formation of these nitrogenous byproducts during chloramination might be of concern considering their potential toxicity.
DOI: 10.1021/acs.est.6b04819
PubMed: 27936646
Affiliations:
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All molecules led to the formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production yields. Resorcinol, a major precursor of chloroform, also formed di/trichloroacetonitrile, di/trichloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and fragmentation patterns from electronic impact and positive chemical ionization modes, several products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were structurally similar to the heterocyclic compounds formed during chlorination, such as the highly mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic compounds is reported from chloramination process. The formation of these nitrogenous byproducts during chloramination might be of concern considering their potential toxicity.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">27936646</PMID><DateCreated><Year>2016</Year><Month>12</Month><Day>12</Day></DateCreated><DateCompleted><Year>2017</Year><Month>06</Month><Day>21</Day></DateCompleted><DateRevised><Year>2017</Year><Month>06</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5851</ISSN><JournalIssue CitedMedium="Internet"><Volume>51</Volume><Issue>1</Issue><PubDate><Year>2017</Year><Month>Jan</Month><Day>03</Day></PubDate></JournalIssue><Title>Environmental science & technology</Title><ISOAbbreviation>Environ. Sci. Technol.</ISOAbbreviation></Journal><ArticleTitle>Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds.</ArticleTitle><Pagination><MedlinePgn>655-663</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.est.6b04819</ELocationID><Abstract><AbstractText>The potential formation of nitrogenous disinfection byproducts (N-DBPs) was investigated from the chloramination of nitrogenous and non-nitrogenous aromatic compounds. All molecules led to the formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production yields. Resorcinol, a major precursor of chloroform, also formed di/trichloroacetonitrile, di/trichloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and fragmentation patterns from electronic impact and positive chemical ionization modes, several products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were structurally similar to the heterocyclic compounds formed during chlorination, such as the highly mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic compounds is reported from chloramination process. The formation of these nitrogenous byproducts during chloramination might be of concern considering their potential toxicity.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Nihemaiti</LastName><ForeName>Maolida</ForeName><Initials>M</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-0004-2003</Identifier><AffiliationInfo><Affiliation>Curtin Water Quality Research Centre, Department of Chemistry, Curtin University , GPO Box U1987, Perth, Western Australia 6845, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Le Roux</LastName><ForeName>Julien</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>LEESU (UMR MA 102), Université Paris-Est - AgroParisTech , 61 avenue du Général de Gaulle, 94010 Créteil cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hoppe-Jones</LastName><ForeName>Christiane</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Department of Chemical and Environmental Engineering, The University of Arizona , P.O. Box 210011, Tucson, Arizona, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Reckhow</LastName><ForeName>David A</ForeName><Initials>DA</Initials><AffiliationInfo><Affiliation>Department of Civil and Environmental Engineering, University of Massachusetts Amherst , 18 Marston Hall, 130 Natural Resources Rd., Amherst, Massachusetts 01003-9293, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Croué</LastName><ForeName>Jean-Philippe</ForeName><Initials>JP</Initials><AffiliationInfo><Affiliation>Curtin Water Quality Research Centre, Department of Chemistry, Curtin University , GPO Box U1987, Perth, Western Australia 6845, Australia.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>12</Month><Day>20</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Environ Sci Technol</MedlineTA><NlmUniqueID>0213155</NlmUniqueID><ISSNLinking>0013-936X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D002700">Chloramines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D004202">Disinfectants</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014874">Water Pollutants, Chemical</NameOfSubstance></Chemical><Chemical><RegistryNumber>N762921K75</RegistryNumber><NameOfSubstance UI="D009584">Nitrogen</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D002700" MajorTopicYN="N">Chloramines</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004202" MajorTopicYN="N">Disinfectants</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004203" MajorTopicYN="N">Disinfection</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D054879" MajorTopicYN="N">Halogenation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009584" MajorTopicYN="N">Nitrogen</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D014874" MajorTopicYN="N">Water Pollutants, Chemical</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018508" MajorTopicYN="N">Water Purification</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>12</Month><Day>13</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>6</Month><Day>22</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>12</Month><Day>13</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27936646</ArticleId><ArticleId IdType="doi">10.1021/acs.est.6b04819</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Australie</li><li>France</li><li>États-Unis</li></country><region><li>Arizona</li></region></list><tree><country name="Australie"><noRegion><name sortKey="Nihemaiti, Maolida" sort="Nihemaiti, Maolida" uniqKey="Nihemaiti M" first="Maolida" last="Nihemaiti">Maolida Nihemaiti</name></noRegion><name sortKey="Croue, Jean Philippe" sort="Croue, Jean Philippe" uniqKey="Croue J" first="Jean-Philippe" last="Croué">Jean-Philippe Croué</name></country><country name="France"><noRegion><name sortKey="Le Roux, Julien" sort="Le Roux, Julien" uniqKey="Le Roux J" first="Julien" last="Le Roux">Julien Le Roux</name></noRegion></country><country name="États-Unis"><region name="Arizona"><name sortKey="Hoppe Jones, Christiane" sort="Hoppe Jones, Christiane" uniqKey="Hoppe Jones C" first="Christiane" last="Hoppe-Jones">Christiane Hoppe-Jones</name></region><name sortKey="Reckhow, David A" sort="Reckhow, David A" uniqKey="Reckhow D" first="David A" last="Reckhow">David A. 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