Secondary organic aerosol formation from the ozonolysis of cycloalkenes and related compounds. 2004

M D Keywood, and V Varutbangkul, and R Bahreini, and R C Flagan, and J H Seinfeld
Departments of Environmental Science and Engineering and of Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

The secondary organic aerosol (SOA) yields from the laboratory chamber ozonolysis of a series of cycloalkenes and related compounds are reported. The aim of this work is to investigate the effect of the structure of the hydrocarbon parent molecule on SOA formation for a homologous set of compounds. Aspects of the compound structures that are varied include the number of carbon atoms present in the cycloalkene ring (C5 to C8), the presence and location of methyl groups, and the presence of an exocyclic or endocyclic double bond. The specific compounds considered here are cyclopentene, cyclohexene, cycloheptene, cyclooctene, 1-methyl-1-cyclopentene, 1-methyl-1-cyclohexene, 1-methyl-1-cycloheptene, 3-methyl-1-cyclohexene, and methylenecyclohexane. The SOA yield is found to be a function of the number of carbons present in the cycloalkene ring, with an increasing number resulting in increased yield. The yield is enhanced by the presence of a methyl group located at a double-bonded site but reduced by the presence of a methyl group at a non-double-bonded site. The presence of an exocyclic double bond also leads to a reduced yield relative to that of the equivalent methylated cycloalkene. On the basis of these observations, the SOA yield for terpinolene relative to the other cyclic alkenes is qualitatively predicted, and this prediction compares well to measurements of the SOA yield from the ozonolysis of terpinolene. This work shows that relative SOA yields from ozonolysis of cyclic alkenes can be qualitatively predicted from properties of the parent hydrocarbons.

UI MeSH Term Description Entries
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D010126 Ozone The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE). Ground Level Ozone,Low Level Ozone,Tropospheric Ozone,Level Ozone, Ground,Level Ozone, Low,Ozone, Ground Level,Ozone, Low Level,Ozone, Tropospheric
D010316 Particle Size Relating to the size of solids. Particle Sizes,Size, Particle,Sizes, Particle
D002244 Carbon A nonmetallic element with atomic symbol C, atomic number 6, and atomic weight [12.0096; 12.0116]. It may occur as several different allotropes including DIAMOND; CHARCOAL; and GRAPHITE; and as SOOT from incompletely burned fuel. Carbon-12,Vitreous Carbon,Carbon 12,Carbon, Vitreous
D003516 Cycloparaffins Alicyclic hydrocarbons in which three or more of the carbon atoms in each molecule are united in a ring structure and each of the ring carbon atoms is joined to two hydrogen atoms or alkyl groups. The simplest members are cyclopropane (C3H6), cyclobutane (C4H8), cyclohexane (C6H12), and derivatives of these such as methylcyclohexane (C6H11CH3). (From Sax, et al., Hawley's Condensed Chemical Dictionary, 11th ed) Cyclic Olefins,Cycloalkanes,Cycloalkenes,Cycloalkynes,Cyclic Acetylenes,Cyclic Alkenes,Alkenes, Cyclic,Olefins, Cyclic
D003998 Dicarboxylic Acids Acyclic acids that contain two carboxyl groups and have the formula HO2C-R-CO2H, where R may be an aromatic or aliphatic group. Acids, Dicarboxylic
D000081005 Cyclohexane Monoterpenes Monoterpenes that include a cyclohexane ring in their structure. Monoterpenes, Cyclohexane
D000336 Aerosols Colloids with a gaseous dispersing phase and either liquid (fog) or solid (smoke) dispersed phase; used in fumigation or in inhalation therapy; may contain propellant agents. Aerosol
D013729 Terpenes A class of compounds composed of repeating 5-carbon units of HEMITERPENES. Isoprenoid,Terpene,Terpenoid,Isoprenoids,Terpenoids
D014835 Volatilization A phase transition from liquid state to gas state, which is affected by Raoult's law. It can be accomplished by fractional distillation. Vaporization,Volatility

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