Delineating oxidative processes of aqueous C 60 preparations: Role of THF peroxide

Bo Zhang, Min Cho, John D. Fortner, Jaesang Lee, Ching Hua Huang, Joseph B. Hughes, Jae Hong Kim

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The oxidative reactivity of THF derivatives formed during THF/nC 60 synthesis was evaluated with indigo dye as a model compound. The results showed that the formation of previously undetected oxidizing agents during THF/nC 60 synthesis accounted for the degradation of indigo dye by THF/nC 60 (THF/nC 60/unwashed), while THF/nC 60 after vigorous washing (THF/ nC 60/washed) and nC 60 prepared without the use of THFwere not reactive. γ-Butyrolactone (GBL) was detected by GC-MS in the THF/nC 60/unwashed as one of THF derivatives, but showed no reactivity with indigo dye. An organic peroxide was detected in the THF/nC 60/unwashed by HPLC,and was reactive with indigo dye. This compound was found to also account for the elevated antibacterial and bactericidal activities of THF/ nC 60/unwashed on E. coli. Analysis by LC/(+ESI)MS and 1H NMR showed that the detected THF peroxide was tetrahydro-2-(tetrahydrofuran-2- ylperoxy)furan. The formation of THF peroxide during the preparation of aqueous stable C 60 aggregates provides another potential explanation for the reactivity and oxidative stress mechanisms of THF/nC 60 system reported in the literature, although it does not exclude the potential reactivity and toxicity of nC 60 itself.

Original languageEnglish
Pages (from-to)108-113
Number of pages6
JournalEnvironmental Science and Technology
Volume43
Issue number1
DOIs
Publication statusPublished - 2009 Jan 1
Externally publishedYes

Fingerprint

Indigo Carmine
Peroxides
dye
Coloring Agents
Derivatives
Oxidative stress
furan
Oxidants
Washing
Escherichia coli
Toxicity
nuclear magnetic resonance
Oxidative Stress
High Pressure Liquid Chromatography
Nuclear magnetic resonance
toxicity
Degradation
degradation

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry

Cite this

Delineating oxidative processes of aqueous C 60 preparations : Role of THF peroxide. / Zhang, Bo; Cho, Min; Fortner, John D.; Lee, Jaesang; Huang, Ching Hua; Hughes, Joseph B.; Kim, Jae Hong.

In: Environmental Science and Technology, Vol. 43, No. 1, 01.01.2009, p. 108-113.

Research output: Contribution to journalArticle

Zhang, Bo ; Cho, Min ; Fortner, John D. ; Lee, Jaesang ; Huang, Ching Hua ; Hughes, Joseph B. ; Kim, Jae Hong. / Delineating oxidative processes of aqueous C 60 preparations : Role of THF peroxide. In: Environmental Science and Technology. 2009 ; Vol. 43, No. 1. pp. 108-113.
@article{bc7b273669c24b8f82cca0906d563589,
title = "Delineating oxidative processes of aqueous C 60 preparations: Role of THF peroxide",
abstract = "The oxidative reactivity of THF derivatives formed during THF/nC 60 synthesis was evaluated with indigo dye as a model compound. The results showed that the formation of previously undetected oxidizing agents during THF/nC 60 synthesis accounted for the degradation of indigo dye by THF/nC 60 (THF/nC 60/unwashed), while THF/nC 60 after vigorous washing (THF/ nC 60/washed) and nC 60 prepared without the use of THFwere not reactive. γ-Butyrolactone (GBL) was detected by GC-MS in the THF/nC 60/unwashed as one of THF derivatives, but showed no reactivity with indigo dye. An organic peroxide was detected in the THF/nC 60/unwashed by HPLC,and was reactive with indigo dye. This compound was found to also account for the elevated antibacterial and bactericidal activities of THF/ nC 60/unwashed on E. coli. Analysis by LC/(+ESI)MS and 1H NMR showed that the detected THF peroxide was tetrahydro-2-(tetrahydrofuran-2- ylperoxy)furan. The formation of THF peroxide during the preparation of aqueous stable C 60 aggregates provides another potential explanation for the reactivity and oxidative stress mechanisms of THF/nC 60 system reported in the literature, although it does not exclude the potential reactivity and toxicity of nC 60 itself.",
author = "Bo Zhang and Min Cho and Fortner, {John D.} and Jaesang Lee and Huang, {Ching Hua} and Hughes, {Joseph B.} and Kim, {Jae Hong}",
year = "2009",
month = "1",
day = "1",
doi = "10.1021/es8019066",
language = "English",
volume = "43",
pages = "108--113",
journal = "Environmental Science and Technology",
issn = "0013-936X",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Delineating oxidative processes of aqueous C 60 preparations

T2 - Role of THF peroxide

AU - Zhang, Bo

AU - Cho, Min

AU - Fortner, John D.

AU - Lee, Jaesang

AU - Huang, Ching Hua

AU - Hughes, Joseph B.

AU - Kim, Jae Hong

PY - 2009/1/1

Y1 - 2009/1/1

N2 - The oxidative reactivity of THF derivatives formed during THF/nC 60 synthesis was evaluated with indigo dye as a model compound. The results showed that the formation of previously undetected oxidizing agents during THF/nC 60 synthesis accounted for the degradation of indigo dye by THF/nC 60 (THF/nC 60/unwashed), while THF/nC 60 after vigorous washing (THF/ nC 60/washed) and nC 60 prepared without the use of THFwere not reactive. γ-Butyrolactone (GBL) was detected by GC-MS in the THF/nC 60/unwashed as one of THF derivatives, but showed no reactivity with indigo dye. An organic peroxide was detected in the THF/nC 60/unwashed by HPLC,and was reactive with indigo dye. This compound was found to also account for the elevated antibacterial and bactericidal activities of THF/ nC 60/unwashed on E. coli. Analysis by LC/(+ESI)MS and 1H NMR showed that the detected THF peroxide was tetrahydro-2-(tetrahydrofuran-2- ylperoxy)furan. The formation of THF peroxide during the preparation of aqueous stable C 60 aggregates provides another potential explanation for the reactivity and oxidative stress mechanisms of THF/nC 60 system reported in the literature, although it does not exclude the potential reactivity and toxicity of nC 60 itself.

AB - The oxidative reactivity of THF derivatives formed during THF/nC 60 synthesis was evaluated with indigo dye as a model compound. The results showed that the formation of previously undetected oxidizing agents during THF/nC 60 synthesis accounted for the degradation of indigo dye by THF/nC 60 (THF/nC 60/unwashed), while THF/nC 60 after vigorous washing (THF/ nC 60/washed) and nC 60 prepared without the use of THFwere not reactive. γ-Butyrolactone (GBL) was detected by GC-MS in the THF/nC 60/unwashed as one of THF derivatives, but showed no reactivity with indigo dye. An organic peroxide was detected in the THF/nC 60/unwashed by HPLC,and was reactive with indigo dye. This compound was found to also account for the elevated antibacterial and bactericidal activities of THF/ nC 60/unwashed on E. coli. Analysis by LC/(+ESI)MS and 1H NMR showed that the detected THF peroxide was tetrahydro-2-(tetrahydrofuran-2- ylperoxy)furan. The formation of THF peroxide during the preparation of aqueous stable C 60 aggregates provides another potential explanation for the reactivity and oxidative stress mechanisms of THF/nC 60 system reported in the literature, although it does not exclude the potential reactivity and toxicity of nC 60 itself.

UR - http://www.scopus.com/inward/record.url?scp=61849154741&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=61849154741&partnerID=8YFLogxK

U2 - 10.1021/es8019066

DO - 10.1021/es8019066

M3 - Article

C2 - 19209592

AN - SCOPUS:61849154741

VL - 43

SP - 108

EP - 113

JO - Environmental Science and Technology

JF - Environmental Science and Technology

SN - 0013-936X

IS - 1

ER -