**4. Dicarboxlic acids distributions in the atmosphere**

Numerous organic compounds significantly contribute to the aerosol load of the atmosphere and thus to the radiative forcing of climate. Among others the influence of organic aerosol on cloud droplet formation is a key point in evaluating effects of anthropogenic emissions on climate. In contrast to sulfate more uncertainties exist about organics and in particular for secondary organic aerosol species which are more oxygenated and hygroscopic than primary organic species (Saxena and Hildemann, 1996). Among oxygenated organic species, dicarboxylic acids are probably the best quantified species, though they represent a small fraction of the total organic mass (Kawamura and Ikushima, 1993). Glutaric and malonic acid the atmosphere have potential to increase the cloud condensation nuclei (CCN) activation of major inorganic aerosol such as ammonium sulfate (Cruz and Pandis, 1998). These findings suggest a potentially important role played by dicarboxylic acids on radiative forcing and stimulate their studies since the sources of diacids in the atmosphere remain poorly understood and quantified.

Whatever the region; urban and continental, or remote marine (see Figure 1 which carried out from Table 3), oxalic acid (C2: HOOCCOOH) is always found to be the most abundant diacid followed by succinic (C4: HOOC(CH2)2COOH) and/or malonic (C3: HOOCCH2COOH) acid with concentrations of several hundreds of nanograms per cubic meter in urban and continental regions (Kawamura and Ikushima, 1993; Kawamura and Kaplan, 1987) to a few tens of nanograms per cubic meter in remote marine boundary layer (Kawamura and Sakagushi, 1999; Sempere and Kawamura, 2003). In Europe, the most continuous study of diacids was conducted over one year by Limbeck et al., (2005) at Vienna, Austria. Although available data on diacids are more sparse at midlatitudes in Europe, they tend to show that oxalic acid levels at nonurban or rural sites are not considerably different from those at urban sites (Limbeck and Puxbaum, 1999; Rohrl and Lammel, 2001).

Motor exhausts have been proposed to be primary sources of oxalic, malonic, succinic, and glutaric (C5: HOOC(CH2)3COOH) acids (Grosjean et al., 1978; Kawamura and Kaplan, 1987). Some of these diacids are also emitted by wood burning, particularly malonic acid (pine wood) and succinic acid (oak wood) (Rogge et al., 1991; Rogge et al., 1993). Note that until now no direct source of malic (hydroxysuccinic: hC4: HOOCCH2CHOHCOOH) and tartaric (dihydroxysuccinic: dhC4: HOOC(CHOH)2COOH) acids has been identified.

Glutaric, succinic, and adipic (C6: HOOC(CH2)4COOH) acids have been identified in laboratory studies (Hatakeyama et al., 1985) as secondary organic aerosol products of the reaction of O3 with cyclohexene, a symmetrical alkene molecule similar to monoterpenes emitted by the biosphere. Hatakeyama et al. (1985) also suggested that malonic and oxalic acids are also produced in the cyclohexene-ozone system.

Unsaturated fatty acids with a double bond at the C9 position like cis-9-octadecenoic (oleic) acid are oxidized into C9 diacid (azelaic acid) and other products hereafter mainly oxidized into shorter diacids hahah(Kawamura and Ikushima, 1994; Kawamura and Kaplan, 1987; Kawamura et al., 1985). These unsaturated acids which are abundant in marine phytoplankton and terrestrial higher plant leaves are also emitted by anthropogenic sources such as meat cooking (Rogge, 1991; Rogge et al., 1998) and wood burning processes (Rogge et al., 1998).

338 Atmospheric Aerosols – Regional Characteristics – Chemistry and Physics

**4. Dicarboxlic acids distributions in the atmosphere** 

and bifunctional alcohols are used as lubricants.

remain poorly understood and quantified.

sites (Limbeck and Puxbaum, 1999; Rohrl and Lammel, 2001).

acids are also produced in the cyclohexene-ozone system.

diamines such as 1,3-bis(aminomethyl)benzene, 1,4(bisaminomethyl)cyclohexane, and bis(4 aminocyclohexyl)methane are also of commercial interest. Esters of adipic acid with mono-

Numerous organic compounds significantly contribute to the aerosol load of the atmosphere and thus to the radiative forcing of climate. Among others the influence of organic aerosol on cloud droplet formation is a key point in evaluating effects of anthropogenic emissions on climate. In contrast to sulfate more uncertainties exist about organics and in particular for secondary organic aerosol species which are more oxygenated and hygroscopic than primary organic species (Saxena and Hildemann, 1996). Among oxygenated organic species, dicarboxylic acids are probably the best quantified species, though they represent a small fraction of the total organic mass (Kawamura and Ikushima, 1993). Glutaric and malonic acid the atmosphere have potential to increase the cloud condensation nuclei (CCN) activation of major inorganic aerosol such as ammonium sulfate (Cruz and Pandis, 1998). These findings suggest a potentially important role played by dicarboxylic acids on radiative forcing and stimulate their studies since the sources of diacids in the atmosphere

Whatever the region; urban and continental, or remote marine (see Figure 1 which carried out from Table 3), oxalic acid (C2: HOOCCOOH) is always found to be the most abundant diacid followed by succinic (C4: HOOC(CH2)2COOH) and/or malonic (C3: HOOCCH2COOH) acid with concentrations of several hundreds of nanograms per cubic meter in urban and continental regions (Kawamura and Ikushima, 1993; Kawamura and Kaplan, 1987) to a few tens of nanograms per cubic meter in remote marine boundary layer (Kawamura and Sakagushi, 1999; Sempere and Kawamura, 2003). In Europe, the most continuous study of diacids was conducted over one year by Limbeck et al., (2005) at Vienna, Austria. Although available data on diacids are more sparse at midlatitudes in Europe, they tend to show that oxalic acid levels at nonurban or rural sites are not considerably different from those at urban

Motor exhausts have been proposed to be primary sources of oxalic, malonic, succinic, and glutaric (C5: HOOC(CH2)3COOH) acids (Grosjean et al., 1978; Kawamura and Kaplan, 1987). Some of these diacids are also emitted by wood burning, particularly malonic acid (pine wood) and succinic acid (oak wood) (Rogge et al., 1991; Rogge et al., 1993). Note that until now no direct source of malic (hydroxysuccinic: hC4: HOOCCH2CHOHCOOH) and tartaric

Glutaric, succinic, and adipic (C6: HOOC(CH2)4COOH) acids have been identified in laboratory studies (Hatakeyama et al., 1985) as secondary organic aerosol products of the reaction of O3 with cyclohexene, a symmetrical alkene molecule similar to monoterpenes emitted by the biosphere. Hatakeyama et al. (1985) also suggested that malonic and oxalic

(dihydroxysuccinic: dhC4: HOOC(CHOH)2COOH) acids has been identified.

Warneck suggested that in the marine atmosphere clouds generate oxalic acid from glyoxal formed by oxidation of acetylene and glycolaldehyde formed by oxidation of ethane (Warneck, 2000). Note that along these processes glyoxylic acid (CHOCOOH) represents a key intermediate (see figure 3) whereas diacids other than oxalic acid are not produced. The formation of dicarboxylic acids in the continental atmosphere (Ervens et al., 2004a) involves production of glyoxal from toluene and of glycolaldehyde from isoprene as well as aqueous phase reactions of adipic and glutaric acids produced by oxidation of cyclohexene. Recently more literature has become available on the formation of oxalic acid that includes also the oxidation of methylglyoxal, an oxidation product of toluene and isoprene, via intermediate steps involving pyruvic and acetic acids (Lim et al., 2005). Since this diacid production pathway also forms oligomers, the knowledge of the sources of diacids is also of importance for the understanding of secondary organic aerosol formation.

The relative contribution of primary and secondary sources of diacids in the atmosphere remains poorly understood. Even though it is agreed that they are likely to be mainly secondary in origin it is not known in which proportion their precursors come from anthropogenic and biogenic sources.

**Figure 2.** Comparison of dicarboxylic acids distribution in urban/continental and remote marine based on the data collection on table 3


The Chemistry of Dicarboxylic Acids in the Atmospheric Aerosols 341

**References Location Oxalic Malonic Succinic Glutaric Adipic**  (Kawamura and Kaplan, 1987) Green House LA 1.31 0.3 0.29 0.04 0.1 (Kawamura and Kaplan, 1987) Green House LA 2.83 0.14 0.86 0 0.22 (Kawamura and Sakagushi, 1999) North Pacific 44.7 23.2 19.5 2.57 3.08 (Kawamura and Sakagushi, 1999) North Pacific 8.73 2.18 2.16 0.61 1.26 (Kawamura and Sakagushi, 1999) North Pacific 10.6 1.98 2.22 0.23 2.12 (Kawamura and Sakagushi, 1999) North Pacific 28.6 12.8 13 1.84 1.34 (Kawamura and Sakagushi, 1999) North Pacific 667 189 93 20.1 4.9 (Kawamura and Sakagushi, 1999) North Pacific 190 38.6 16.7 10.2 2.76 (Kawamura and Sakagushi, 1999) North Pacific 88.5 34.5 21.6 4.72 6.04 (Kawamura and Sakagushi, 1999) North Pacific 24.9 5.66 10.1 1.87 1.67 (Kawamura and Sakagushi, 1999) North Pacific 10 2.12 1.52 0.32 0.43 (Kawamura and Sakagushi, 1999) North Pacific 18.3 3.45 4.02 0.62 0.46 (Kawamura and Sakagushi, 1999) North Pacific 25.5 5.93 2.99 0.65 0.4 Kawamura (1996) Antarctic 1.59 0.13 0.63 0.31 0.49 Kawamura (1996) Antarctic 3.12 0.38 5.77 0.58 0.85 Kawamura (1996) Antarctic 3.26 0.52 1.18 0.34 0.33 Kawamura (1996) Antarctic 10.29 2.69 61.53 2.26 1.81 Narukawa(1999) Indonesia 2200 800.3 1090 310 350 Narukawa(1999) Indonesia 225 18.4 123 30 40 Khwaja (1994) semi urban site NY 308 84 55 12 89 Khwaja (1994) semi urban site NY 245 92 106 16.3 101 Khwaja (1994) semi urban site NY 118 165 107 15 40 Khwaja (1994) semi urban site NY 58 81 129 20 21 Khwaja (1994) semi urban site NY 298 96 90 23 31 Khwaja (1994) semi urban site NY 1 43 0.5 39 20 Khwaja (1994) semi urban site NY 360 88 167 46 50 Sempere (2003) Western Pacific 428.5 78.6 33.4 7.6 7.2 Rohrl (2002) rural(I) 0 0 14 0 0 Rohrl (2002) rural(II) 0 0 8.8 0 0 Rohrl (2002) rural(III) 0 0 18 0 0 (Kawamura et al., 2007) Canadian arctic 9.89 2.74 2.16 0.54 0.51 (Kawamura et al., 2007) Canadian arctic 8.3 2.87 1.44 0.37 0.26 (Kawamura et al., 2007) Canadian arctic 5.26 1.67 1.08 0.22 0.27 (Narukawa et al., 2002) Arctic,Alert 23.5 5.03 3.21 1.21 0.54 (Narukawa et al., 2002) Arctic,Alert 40.09 11.6 15.67 2.16 0.55 (Mochida et al., 2007) North Pacific,ACE 600 110 52 8.9 2 (b)

**Table 3.** Summary of aerosol dicarboxylate concentration (ng m-3) in urban/continental (a) remote

marine (b) locations


**References Location Oxalic Malonic Succinic Glutaric Adipic**  (Grosjean et al., 1978) New York 0 3.6 21.8 17.2 13.2 (Grosjean et al., 1978) New York 0 3.9 24.9 23.2 11.6 (Kawamura and Kaplan, 1987) West LA 6.38 1.58 1.96 0.6 2.22 (Kawamura and Kaplan, 1987) West LA 2.12 0.4 0.66 0.22 0.94 (Kawamura and Kaplan, 1987) West LA 8.13 0.72 2.34 0.66 3.31 (Kawamura and Kaplan, 1987) West LA 8.65 1.45 2.37 0.74 0.49 (Kawamura and Kaplan, 1987) Down Town LA 6.21 0.71 1.19 0.52 0.1 (Kawamura and Kaplan, 1987) Down Town LA 6.6 0.76 1.84 0.52 0.2 (Kawamura and Kaplan, 1987) Down Town LA 8.31 1.22 2.13 0.83 0.63 (Sempere and Kawamura, 1994) Tokyo 29.65 6.69 13.18 3.72 6.66 (Sempere and Kawamura, 1994) Tokyo 58.89 20.29 28.82 7.54 6.79 (Sempere and Kawamura, 1994) Tokyo 330 141.3 161.1 4.15 2.91 (Limbeck and Puxbaum, 1999) South Africa 193 142 58 8.8 7.9 (Limbeck and Puxbaum, 1999) Sonblick Observatory 153 22 14 2.7 4.4 (Limbeck and Puxbaum, 1999) Vienna 340 244 117 26 117 (Kawamura and Watanabe, 2004) Tokyo 357 71.4 73.4 23.1 25.8 (Kawamura and Watanabe, 2004) Tokyo 157 44 41 11 13 (Kawamura and Watanabe, 2004) Tokyo 186 40.5 47.4 18.2 14.2 (Rohrl and Lammel, 2001) Helsinki 0 0 30 0 0 (Ho et al., 2006) Hong Kong (Road) 478 89.1 71.88 20 10.7 (Ho et al., 2006) Hong Kong (Road) 268 47.6 33 6.95 12.7 (Hsieh et al., 2007) Tainan,Taiwan 574 65.8 101 43 13.2 (Hsieh et al., 2007) Tainan,Taiwan 432 34.2 87.9 10.3 8.8 (Limbeck et al., 2005) Vienna, Austria 99.6 34 37 7.7 3.3 (Limbeck et al., 2005) Vienna, Austria 66.2 38.6 30.8 6.6 3.2 (Limbeck et al., 2005) Vienna, Austria 63.1 21.5 31.2 5.6 2.5 (Limbeck et al., 2005) Mt Rax, Austria 34.5 9.1 16.4 2.3 0.8 (Limbeck et al., 2005) Mt Rax, Austria 26.4 6.9 14.9 2.3 4.3 (Limbeck et al., 2005) Mt Rax, Austria 32.6 16.4 22.4 3 1.7 (Decesari et al., 2006) Rondonia, Brazil 194.7 73.1 123.5 23.5 14.5 (Decesari et al., 2006) Rondonia, Brazil 793.3 56.8 210.2 32.1 12.6 (Decesari et al., 2006) Rondonia, Brazil 937.9 128.5 423.9 34.7 21.2 (Decesari et al., 2006) Rondonia, Brazil 1260 476.5 667.2 121.1 97.4 (Wang et al., 2006) Hong Kong (Tunnel) 505 69.4 85.2 20.9 26.4 (Wang et al., 2006) Hong Kong (Tunnel) 221 34.5 32.7 14.7 13.5 (Wang et al., 2006) Hong Kong (Tunnel) 234 42 51.4 17.1 24.7 (Wang et al., 2006) Hong Kong (Tunnel) 312 59.7 62.9 16.7 15.5 (Wang et al., 2006) Hong Kong (Tunnel) 633 59.3 95.1 30.3 25.9 (a)

**Table 3.** Summary of aerosol dicarboxylate concentration (ng m-3) in urban/continental (a) remote marine (b) locations

The Chemistry of Dicarboxylic Acids in the Atmospheric Aerosols 343

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Mohd Zul Helmi Rozaini

*School of Environmental Sciences, University of East Anglia, Norwich, Norfolk, UK Department of Chemical Sciences, University Malaysia Terengganu, Kuala Terengganu,* 

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**Figure 3.** Multiphase organic chemistry producing C2–C5 diacids from key biogenic and anthropogenic precursors. The box refers to the aqueous phase. The figure is mainly adapted from (Ervens et al., 2004b) with modifications to account for the reaction pathway methylglyoxal/pyruvic acid/acetic acid/glyoxylic acid suggested by (Lim et al., 2005). In addition to cyclohexene used by (Ervens et al., 2004b)as a model compound for symmetrical alkenes, following (Legrand et al., 2007) we also report the oleic acid degradation into azelaic, C4 and C5 diacids.

## **Author details**

342 Atmospheric Aerosols – Regional Characteristics – Chemistry and Physics

**Figure 3.** Multiphase organic chemistry producing C2–C5 diacids from key biogenic and anthropogenic precursors. The box refers to the aqueous phase. The figure is mainly adapted from (Ervens et al., 2004b) with modifications to account for the reaction pathway methylglyoxal/pyruvic acid/acetic acid/glyoxylic acid suggested by (Lim et al., 2005). In addition to cyclohexene used by (Ervens et al., 2004b)as a model compound for symmetrical alkenes, following (Legrand et al., 2007) we also report the

oleic acid degradation into azelaic, C4 and C5 diacids.

Mohd Zul Helmi Rozaini

*School of Environmental Sciences, University of East Anglia, Norwich, Norfolk, UK Department of Chemical Sciences, University Malaysia Terengganu, Kuala Terengganu, Terengganu, Malaysia* 

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**Chapter 12** 

© 2012 Jiang et al.; licensee InTech. This is an open access chapter distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

© 2012 Jiang et al.; licensee InTech. This is a paper distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

**Effects of Inorganic Seeds on Secondary** 

Biwu Chu, Jingkun Jiang, Zifeng Lu, Kun Wang, Junhua Li and Jiming Hao

Atmospheric aerosol has significant influences on human health (Kaiser, 2005), visibility degradation (Cheng et al., 2011), and climate change (Satheesh and Moorthy, 2005). It was found that organic aerosols (OA) was the most abundant component of atmospheric aerosol (He et al., 2001) and more than 50% of the total OA are secondary organic aerosols (SOA) (Duan et al., 2005). SOA are produced from the oxidation of volatile organic compounds (VOCs) followed by gas-particle partitioning of the semivolatile organic products. Among the various VOCs, aromatic hydrocarbons are one type of SOA precursors which have drawn the most attention due to their abundance in the air and high SOA contribution to urban atmospheres (Lewandowski et al., 2008). Toluene and *m-*xylene are the two of the

The detailed mechanism and controlling factors of SOA formation are not fully understood yet, which leads to the lower SOA level prediction from air quality models than the ambient measurements (Volkamer et al., 2006). Using smog chamber, SOA formation process can be investigated under controlled experimental conditions. Series of smog experiments have been conducted by different research groups to investigate the effects of background seed aerosols on SOA formation (Cao and Jang, 2007, Czoschke et al., 2003, Gao et al., 2004, Jang et al., 2002, Liggio and Li, 2008). Increased SOA formation and SOA yields were observed with the presence of acid seed aerosols. The effects of acidic seeds suggest that aerosol phase reactions may play an important role on SOA formation (Jang et al., 2002). Interactions between the organic and inorganic components of aerosols are important for further understanding the SOA formation process. Most research concludes that acid-catalyzed aerosol-phase reactions generate additional aerosol mass due to the production of oligomeric products with large molecular weight and extremely low volatility (Cao and Jang, 2007, Czoschke et al., 2003, Gao et al., 2004) and, therefore, enhance SOA formation.

**Organic Aerosol (SOA) Formation** 

Additional information is available at the end of the chapter

most abundant aromatic hydrocarbon species.

http://dx.doi.org/10.5772/48424

**1. Introduction** 


**Chapter 12** 
