Secondary limonene endo-ozonide: A major product from gas-phase ozonolysis of <math xmlns="http://www.w3.org/1998/Math/MathML"><mi>R</mi></math>-(<math xmlns="http://www.w3.org/1998/Math/MathML"><mo>+</mo></math>)-limonene at ambient temperature: Fid-Bau Portal

Fachinformationsdienst BAUdigital

A platform for research: civil engineering, architecture and urbanism

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

Nørgaard, A.W. / Nøjgaard, J.K. / Larsen, K. / Sporring, S. / Wilkins, C.K. / Clausen, P.A. / Wolkoff, P.

AbstractA 16s 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-1-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 $150^{\circ} C$ and were absent at $200^{\circ} C$ . 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 $H_{2} O_{2}$ , 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- $H_{2} O_{2}$ ] 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.

Access

Check availability in my library

Order at Subito €

Page navigation

Document information

Export, share and cite

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

Nørgaard, A.W. / Nøjgaard, J.K. / Larsen, K. / Sporring, S. / Wilkins, C.K. / Clausen, P.A. / Wolkoff, P.

AbstractA 16s 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-1-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 $150^{\circ} C$ and were absent at $200^{\circ} C$ . 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 $H_{2} O_{2}$ , 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- $H_{2} O_{2}$ ] 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.

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

Nørgaard, A.W. / Nøjgaard, J.K. / Larsen, K. / Sporring, S. / Wilkins, C.K. / Clausen, P.A. / Wolkoff, P.

AbstractA 16s 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-1-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 $150^{\circ} C$ and were absent at $200^{\circ} C$ . 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 $H_{2} O_{2}$ , 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- $H_{2} O_{2}$ ] 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.

Access

Check availability in my library

Order at Subito €

Page navigation

Document information

Export, share and cite

Document information

Title:

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

Contributors:

Nørgaard, A.W. (author) / Nøjgaard, J.K. (author) / Larsen, K. (author) / Sporring, S. (author) / Wilkins, C.K. (author) / Clausen, P.A. (author) / Wolkoff, P. (author)

Published in:

Atmospheric Environment ; 40 ; 3460-3466

Publication date:

2006-02-06

Size:

7 pages

ISSN:

DOI:

https://doi.org/10.1016/j.atmosenv.2006.02.007

Type of media:

Article (Journal)

Type of material:

Electronic Resource

Language:

English

Keywords:

Endo-limonene ozonide , Gas-phase ozonolysis , Limonene , Pressurized liquid extraction

Similar titles

A chamber study of secondary organic aerosol formation by limonene ozonolysis

Chen, X. / Hopke, P. K. | Wiley | 2010

Free access

Limonene ozonolysis in the presence of nitric oxide: Gas-phase reaction products and yields

Ham, Jason E. / Harrison, Joel C. / Jackson, Stephen R. et al. | Elsevier | 2016

A new agent for derivatizing carbonyl species used to investigate limonene ozonolysis

Wells, J.R. / Ham, Jason E. | Elsevier | 2014

Transformation of peroxide products of (S)-(-)-limonene ozonolysis in the system HCl-methanol

Ishmuratov, G. Y. / Legostaeva, Y. V. / Garifullina, L. R. et al. | British Library Online Contents | 2014

Predicting the evolution of secondary organic aerosol (SOA) size distributions due to limonene ozonolysis in indoor environments

Youssefi, Somayeh | Online Contents | 2016