Secondary limonene endo-ozonide: A major product from gas-phase ozonolysis of R-(+)-limonene at ambient temperature

AW Norgaard, JK Nojgaard, K Larsen, Sune Sporring, CK Wilkins, PA Clausen, P Wolkoff

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26 Citations (SciVal)

Abstract

A 16 s old gas-phase ambient temperature and 1% relative humidity reaction mixture of ozone and R-limonene (ca. 1:10) was sampled on XAD-2 resin followed by pressurized liquid extraction with dichloromethane at ambient temperature. Low temperature on-column injection and gas chromatography (GC) revealed equal amounts of diastereomeric secondary endo-limonene ozonides, in addition to 4-acetyl-l-methyl-cyclohexene (AMCH), 3-isopropyl-6-oxo-heptanal (IPOH), and endo-limonene mono-epoxides. The secondary endo-limonene ozonides began to decrease at extraction temperature above 150 degrees C and were absent at 200 degrees C. Their formation was unaffected by an increase of the relative humidity to 15%. The identification of the secondary limonene ozonides was confirmed by (1) unique consecutive losses of OH and H2O2, respectively, from the protonated quasi-molecular ion in GC-chemical ionization mass spectrometry mode (isobutane), in addition to high resolution mass determination of [M-OH] and [M-H2O2] ions in EI mode; (2) comparison of mass spectral data to that of synthesized secondary endo-limonene ozonides; and (3) oxidation of dimethyl sulfide to dimethyl sulfoxide and subsequent increase of IPOH.
Original languageEnglish
Pages (from-to)3460-3466
JournalAtmospheric Environment
Volume40
Issue number19
DOIs
Publication statusPublished - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Analytical Chemistry (S/LTH) (011001004)

Subject classification (UKÄ)

  • Meteorology and Atmospheric Sciences

Keywords

  • pressurized
  • liquid extraction
  • limonene
  • endo-limonene ozonide
  • gas-phase ozonolysis

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