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

Norgaard, AW ; Nojgaard, JK ; Larsen, K ; Sporring, Sune LU ; Wilkins, CK ; Clausen, PA and Wolkoff, P (2006) In Atmospheric Environment 40(19). p.3460-3466
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
pressurized, liquid extraction, limonene, endo-limonene ozonide, gas-phase ozonolysis
in
Atmospheric Environment
volume
40
issue
19
pages
3460 - 3466
publisher
Elsevier
external identifiers
  • wos:000238504400004
  • scopus:33646784716
ISSN
1352-2310
DOI
10.1016/j.atmosenv.2006.02.007
language
English
LU publication?
yes
additional info
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)
id
e3a7819c-c1dc-454d-bf11-ea4da90135d0 (old id 405749)
date added to LUP
2016-04-01 16:25:49
date last changed
2020-03-11 05:35:29
@article{e3a7819c-c1dc-454d-bf11-ea4da90135d0,
  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.},
  author       = {Norgaard, AW and Nojgaard, JK and Larsen, K and Sporring, Sune and Wilkins, CK and Clausen, PA and Wolkoff, P},
  issn         = {1352-2310},
  language     = {eng},
  number       = {19},
  pages        = {3460--3466},
  publisher    = {Elsevier},
  series       = {Atmospheric Environment},
  title        = {Secondary limonene endo-ozonide: A major product from gas-phase ozonolysis of R-(+)-limonene at ambient temperature},
  url          = {http://dx.doi.org/10.1016/j.atmosenv.2006.02.007},
  doi          = {10.1016/j.atmosenv.2006.02.007},
  volume       = {40},
  year         = {2006},
}