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Photocatalytic Degradation of Polycyclic Aromatic Hydrocarbon in Soil

Xiaoping Chen , Qiaoshan Chen , Jinhong Bi

Progress in Chemistry ›› 2021, Vol. 33 ›› Issue (8) : 1323 -1330.

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Progress in Chemistry ›› 2021, Vol. 33 ›› Issue (8) : 1323-1330 DOI: 10.7536/PC200743
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Photocatalytic Degradation of Polycyclic Aromatic Hydrocarbon in Soil
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Abstract

As a class of persistent organic pollutants, polycyclic aromatic hydrocarbons(PAHs) have been widely distributed in soil, which is highly stable, hydrophobic, cytotoxic and difficult to degrade. The PAHs are commonly produced from transportation, industrial production and waste incineration. In recent years, the increasingly serious pollution of PAHs in soil has become a great threat to soil ecology, food safety and public health. Hence, the treatment of PAHs contaminated soil is of great importance and urgently needed. Among numerous strategies for PAHs degradation, photocatalytic technology has attracted extensive attention due to its low energy consumption, facile operation and environmental friendliness. In this paper, the photocatalytic degradation mechanism and pathway of PAHs are overviewed, the current state of knowledge concerning photocatalytic remediation of PAHs contaminated soils is reviewed, and the impacts of different environmental factors on the degradation efficiency of photocatalysts are discussed. Furthermore, we summarize the challenges to apply photocatalytic technology in the field of PAHs contaminated soil remediation.

Contents

1 Introduction

2 Photocatalytic mechanism of PAHs degradation

3 Applications of photocatalysts in remediation of PAHs in soil

3.1 TiO2

3.2 Iron-based materials

3.3 g-C3N4

4 The main environmental factors affecting degradation of PAHs in soil

4.1 Light irradiation

4.2 Soil thickness

4.3 Soil moisture content

4.4 Soil pH

4.5 Solid phase of soil

5 Conclusion and outlook

Graphical abstract

Keywords

polycyclic aromatic hydrocarbons / photocatalysis / soil remediation / degradation mechanism / influence factor

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Xiaoping Chen, Qiaoshan Chen, Jinhong Bi. Photocatalytic Degradation of Polycyclic Aromatic Hydrocarbon in Soil. Progress in Chemistry, 2021, 33(8): 1323-1330 DOI:10.7536/PC200743

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1 Introduction

Polycyclic aromatic hydrocarbons (PAHs) are a class of hydrocarbons composed of two or more benzene rings arranged in linear, angular or cluster form, mostly colorless or yellowish, and are one of the most widely distributed persistent organic pollutants in soil[1,2]. PAHs are teratogenic, carcinogenic, mutagenic and biodegradable, and their toxicity increases with the increase of the number of benzene rings. These substances can be enriched in organisms through the transmission of food chain, and then destroy the genetic material in vivo and induce cell canceration[3,4]. In 1974, the United States Environmental Protection Agency listed 16 kinds of PAHs as the priority pollutants to be controlled, and strictly monitored their environmental concentrations (Table 1); in 2016, the State Council of China issued the Action Plan for Soil Pollution Prevention and Control, which also listed PAHs as the key organic pollutants to be monitored. It can be seen that PAHs pollution has attracted great attention[5][6,7].
With the rapid development of society, the burning of petroleum, coal, natural gas and other fuels produces a large number of PAHs, which enter the soil through atmospheric dry and wet deposition, sewage discharge and other ways, causing serious soil pollution[8]. The national soil pollution survey in 2014 showed that PAHs were the main pollutants in the soil of oil production areas, mining areas, sewage irrigation areas and both sides of trunk highways, and the over-standard rate of PAHs pollution sites could reach 1. 4%[9]. In 2017, Zhang et al analyzed more than 6,000 surface soil samples from various regions of the country, and the results showed that 82.8% of the soil samples were contaminated by PAHs, and the urban pollution was twice and four times as much as the suburban pollution and rural pollution, respectively. The pollution in Northeast China was the most serious, with a concentration of 1467 ng/G[10]. According to Maliszewska-Kordybach soil PAHs pollution degree classification standard, it belongs to severe pollution (> 1000 ng/G)[11]. It can be seen that PAHs soil pollution in China is widely distributed and deep, and needs to be solved urgently.
However, as highly hydrophobic compounds, the molecular structure of PAHs is highly stable and difficult to degrade, and the soil itself is complex, so it is difficult to remove PAHs in the soil[12]. The traditional removal methods of PAHs include solvent extraction and chemical oxidation, which can remove PAHs in soil efficiently, but there are also some defects, for example, solvent extraction only transfers pollutants to liquid phase, and does not achieve the degradation of pollutants[13]; The strong oxidants used in chemical oxidation can cause damage to the soil. In recent years, phytoremediation and microbial remediation have attracted more attention in the field of PAHs degradation in soil because of their mild conditions, economy and no secondary pollution. However, phytoremediation technology is slow and incomplete, and the efficiency of degrading bacteria in microbial remediation technology is low and difficult to isolate[14⇓~16]. As a new method of PAHs treatment, photocatalytic technology has the advantages of mild reaction, simple operation, economic and efficient, and no secondary pollution, so it has become one of the potential soil remediation technologies[13,17]. In this paper, the mechanism of photocatalytic degradation of PAHs and its influencing factors are described, and the research progress of photocatalytic remediation of PAHs contaminated soil at home and abroad in recent years is reviewed.

2 Photocatalytic Degradation Mechanism of PAHs

The essence of photocatalytic technology is to convert light energy into chemical energy, and to achieve the degradation of pollutants through the strong oxidative active species generated by photogenerated electrons and holes activating small molecules such as O2 and H2O (Fig. 1). Taking TiO2 as an example, the process of photocatalytic degradation of PAHs can be explained by formulas (1) to (10)[17⇓~19]. When the TiO2 is irradiated by light with energy higher than the forbidden band width, part of the electrons in the valence band are excited to jump to the conduction band, and holes are left in the valence band.The for photogenerated electron (ecb-)- hole (hvb+) pair (formula 1);hvb+) has strong electron-receiving ability and can oxidize OH- or H2O adsorbed on that surface of the catalyst to form hydroxyl radicals (OH) (formula 2, 3); The ecb- can reduce the O2 adsorbed on the surface of the catalyst to form superoxide radicals (·O2) (Formula 4).
The generated ·O2 can further react with H+, H2O, etc. To generate more active substances (Formulas 5 to 9). With the progress of photocatalytic reaction, active substances such as hvb+, hydroxyl radical, ·O2 and hydrogen peroxide radical (HO2·) can continuously attack the organic bonds in PAHs, destroy the structure of PAHs and its intermediates until they are mineralized into CO2 and H2O (Formula 10)[18]. The results showed that · OH was the main free radical in the degradation of PAHs, and its oxidation potential was 2. 8 eV, which had a strong ability to gain electrons and was the oxidant second only to fluorine atom in nature[17].
TiO2+hν→hvb++ecb-
hvb++H2O→H++·OH
hvb++HO-→·OH
ecb- +O2→·O2-
·O2-+H+→HO2·
2·O2-+2H2O→2OH-+O2+H2O2
H2O2+·O2-→O2+OH-+·OH
ecb-+HO2·+H+→·OH+OH-
ecb-+H2O2→OH-+·OH
PAHs+hvb+/活性氧物种→CO2+H2O
The degradation of PAHs takes place step by step, and the degradation rate and the types of intermediate products are affected by many factors, such as the types of reactants, catalysts, free radicals and reaction environment[20]. Taking benzo (a) pyrene as an example, Gupta et al. Used iron oxide to degrade benzo (a) pyrene in soil (Fig. 2), studied the degradation rate and possible degradation pathway of benzo [a] pyrene in soil with different pH values, and found that the degradation rate of benzo [a] pyrene was faster in acidic soil, and its degradation rate constants in neutral, acidic and alkaline soil were 7.69×10-3/h, 1.11×10-2/h and 9.97×10-3/h respectively[21]; Benzo (a) pyrene was mainly degraded by ketolysis and hydroxylation, but the intermediates formed at different pH values were also different, for example, 9-hydroxybenzo (a) pyrene-7,8-dione (m/Z 299) and benzo (a) Pyrene-4 were detected in neutral soil at the initial stage of photocatalytic degradation of benzo [a] pyrene.5-dione (m/Z 283), whereas 4-hydroxybenzo (a) pyrene-5,7,8-trione-9,10-epoxide (m/Z 331) and 4,5-dihydroxybenzo (a) pyrene or 4-hydroxybenzo [a] pyrene-5-one (m/z-285) were detected in alkaline soils. A large number of studies have shown that the main intermediates of photocatalytic degradation of PAHs are alcohols, ketones, quinones, pyran and other compounds, in which the intermediates with hydroxyl, aldehyde, carbonyl and other groups are more prone to ring-opening reaction, because these groups are electron-rich groups and are more vulnerable to the attack of electrophilic free radicals[20⇓⇓⇓⇓~25]. To sum up, the degradation of PAHs is a process in which the pollutants undergo hydroxylation, ketolysis, ring-opening and other reactions, the concentration of pollutants decreases, the molecular weight of intermediates decreases, and finally the mineralization is completed.

3 Application of Photocatalytic Materials in Soil PAHs Remediation

In the field of photocatalytic remediation of PAHs in soil, the reported catalysts mainly include iron-based materials such as TiO2, Fe2O3 and graphite-phase carbon nitride (g-C3N4). These three types of photocatalysts have the advantages of good photocatalytic performance, low cost, easy synthesis and environmental friendliness. Table 2 summarizes the application examples of their remediation of PAHs in soil.

3.1 TiO2

As a commercial semiconductor photocatalyst, TiO2 has been widely used in wastewater treatment, air purification, sterilization, energy conversion and other fields because of its strong oxidation ability, high chemical stability, environmental protection and non-toxicity. The most commonly used TiO2 are anatase and rutile[26]. Li Peijun, et al., Shenyang Institute of Applied Ecology, Chinese Academy of Sciences, compared the degradation performance of anatase and rutile TiO2 on PAHs in soil, and found that under the same conditions, the degradation effect of anatase TiO2 (degradation rate 43.5%) on pyrene was better than that of rutile TiO2 (degradation rate 38.7%)[27,28]. This is due to the fact that anatase TiO2 have more abundant surface active sites. In addition, the degradation of different kinds of PAHs by anatase TiO2 was also studied, and the results showed that the degradation rate of benzo (a) pyrene by anatase TiO2 was higher than that of phenanthrene and pyrene[29,30]. Eker et al. Also evaluated the catalytic performance of TiO2, and found that the degradation ability of TiO2 for tricyclic or tetracyclic PAHs was higher than that for pentacyclic or hexacyclic PAHs by comparing the degradation of 12 different kinds of PAHs in the same soil[31]. However, whether anatase or rutile, the TiO2 has a low utilization of visible light, and can only be removed under ultraviolet irradiation. Based on this, Rababah et al improved the experimental method of PAHs degradation by extracting pollutants from soil and injecting them into a glass container coated with TiO2, and achieved about 99% degradation rate of fluoranthene under full-band light source[32]. Rachna et al. Improved the visible light utilization by modifying the TiO2. The researchers synthesized TiO2@ZnHCF nanoparticles by co-precipitation method, which not only improved the maximum absorption wavelength of the catalyst, but also increased its surface active sites[33]. Under natural light, the degradation rate of acenaphthene, phenanthrene and fluorene in soil by the composite material can reach 82% to 86%, which is about twice that of pure TiO2.

3.2 Iron-based materials such as iron oxides

Iron oxides and other iron-based materials are widely found in the nature of minerals, which are cheap and easy to prepare. Compared with TiO2, iron-based materials have narrower band gap, richer morphology and larger specific surface area, and have good photocatalytic activity. Zhang et al studied the degradation effect of Fe2O3 on benzo (a) pyrene, pyrene and phenanthrene in soil. The results showed that acidic conditions were conducive to the degradation of benzo (a) pyrene and pyrene, and the degradation rate was about 80%[34]. Alkaline condition was favorable for the degradation of phenanthrene, and the degradation rate was about 70%. Gupta used β-FeOOH nanorods to degrade phenanthrene, and the removal efficiency was about 65% under acidic conditions[35]. In addition, Gupta et al. Also compared the degradation effects of five different forms of iron oxides, including α-FeOOH, β-FeOOH, Fe3O4, γ-Fe2O3 and α-Fe2O3, on benzo (a) pyrene in soil. Among them, α-FeOOH is not only chemically stable, but also has a relatively high specific surface area, so the degradation effect is the best, and the degradation rate of benzo (a) pyrene can reach 70%[21]. In addition to iron oxides, some new iron-based materials, such as metal hexacyanoferrate (MHCFs), have also attracted the attention of scholars. Shanker et al. Synthesized FeHCF nanoparticles with a band gap of only 1.15 eV and good visible light absorption properties. The results showed that the degradation rates of benzo (a) pyrene, phenanthrene, fluorene, chrysene and anthracene in soil reached 70% -90%[36]. In another study, KZnHCF was also synthesized, and the degradation rates of the above 3 ~ 5 ring PAHs ranged from 68% to 84%[37]. In addition, iron, as an important element in the Fenton reaction, is often used in the removal of PAHs[41]. Luo et al. Used ferrous oxalate as a Fenton reagent to degrade 82.7% of phenanthrene under visible light[42]. They further combined iron-based Fenton reagent with heterogeneous photocatalysis to synthesize a magnetite/carboxylate rich carbon solid composite (MMCRC), which can achieve 93% degradation of phenanthrene under mild conditions[38].

3.3 g-C3N4

Compared with metal compound semiconductor photocatalysts such as TiO2 and iron-based materials, non-metallic material g-C3N4 is a more ideal photocatalytic material because of its advantages of cheap and easy to obtain, stable chemical properties and not easy to cause secondary pollution[43]. Wu Zhiren and Luo Zhijun of Jiangsu University applied g-C3N4 to remove phenanthrene in soil, and the degradation rate was 81. 25% in 3 H[39]. They also compounded Fe3O4 with g-C3N4 and synthesized g-C3N4@Fe3O4 by in-situ co-precipitation method, which improved the porosity and adsorption performance of the catalyst. The g-C3N4@Fe3O4 degraded about 85% of phenanthrene in only 2 hours under visible light, which was twice the degradation effect of pure g-C3N4 under the same conditions[40]. From the point of view of degradation time, TiO2 and iron oxides usually need more than 24 hours to achieve satisfactory degradation rate, while g-C3N4 can achieve similar effect in a short time, which greatly improves the degradation efficiency of PAHs in soil.

4 Main Environmental Factors Affecting PAHs Degradation in Soil

In addition to the performance of the catalyst itself, environmental factors can also affect the degradation of PAHs, mainly affecting the following three aspects of the photocatalytic process: (1) the light utilization rate of the catalyst, (2) the migration of PAHs in the soil, and (3) the adsorption of PAHs by the catalyst. Several major environmental factors are discussed below.

4.1 Light Irradiation

Illumination is an indispensable factor in the photocatalytic process, and both light intensity and wavelength affect the effect of photochemical degradation. In a certain range, the higher the light intensity, the more the number of incident photons received by the soil per unit volume, and the more photogenerated carriers and active species excited by photons[44]. Dong et al studied the effect of light intensity (119~357 W/cm2) on the degradation of phenanthrene and pyrene in soil, and the results showed that the increase of light intensity could effectively promote the degradation of phenanthrene and pyrene[28]. Different from the light intensity, the light wavelength does not necessarily have a linear relationship with the degradation effect of PAHs. Generally speaking, the shorter the wavelength and the higher the energy of incident light, the more favorable the degradation of PAHs. However, good spectral matching is also very important, and the appropriate wavelength can effectively activate PAHs and accelerate their degradation rate. Zhang et al found that the degradation rate of benzo (a) pyrene by TiO2 followed the wavelength order of 254 nm > 310 nm > 365 nm[29]. The degradation rate of pyrene followed the wavelength order of 310 nm > 365 nm > 254 nm, and the degradation rate was the fastest because the ultraviolet radiation at 310 nm matched the absorption peak wavelength of pyrene.

4.2 Soil layer thickness

Particles in the soil can weaken the incident light intensity and affect the photocatalytic effect of deep soil, so the efficiency of photocatalytic degradation of PAHs will decrease with the increase of soil thickness[45]. Zhao et al. found that when the soil thickness increased from 0.07 mm to 0.17 mm, the degradation rate constant of the organochlorine pesticide γ-HCH decreased from 2.02×10-1/d to 7.93×10-2/d;Luo. In the soil layer with a thickness of 2 mm, the degradation rate of phenanthrene reached 91.1%, which may be due to the increase of light transmittance due to higher water content in the soil[46][39]. When the soil thickness increased to 10 mm, the degradation rate of phenanthrene decreased to 42. 4%. For the removal of PAHs in deep soil, the photocatalytic degradation effect can be improved by turning the soil regularly.

4.3 Water content of soil

Water molecules in the soil can improve the absorption of light radiation by the soil, and use itself as a sacrificial agent to generate strong oxidizing hydroxyl radicals under the action of a catalyst. In addition, water molecules have solubilization effect, which accelerates the release of PAHs from soil aggregates and migration into the water phase to increase the content of free pollutants, thus improving the mass transfer rate of pollutants and increasing their contact opportunities with photocatalysts. Graebing et al. carried out direct photolysis experiments of niclosamide in moist soil and air-dry soil respectively, and the results showed that niclosamide could be effectively degraded in moist soil, but not completely degraded in air-dry soil[47]. Higarashi et al. Studied the effect of soil moisture on the photocatalytic degradation of diuron, and the results showed that soil moisture was positively correlated with the degradation rate of diuron[48]. Therefore, the existence of water molecules is an indispensable factor for the photocatalytic degradation of organic compounds, and the increase of soil moisture content can effectively promote the degradation of pollutants.

4.4 Soil pH

The adsorption-desorption behavior of PAHs was affected by pH through changing the surface charge properties of photocatalyst and soil minerals and organic matter, which would change the mass transfer process of PAHs in soil and the adsorption performance of photocatalyst for PAHs[49,50]. The photocatalytic degradation of benzo (a) pyrene in soil with pH values of 5.4, 6.8 and 8.1 was carried out by Gupta et al., and the results showed that the degradation rate of benzo (a) pyrene was the fastest under acidic conditions[21]. Rachna et al found that the degradation of acenaphthene, phenanthrene and fluorene under neutral conditions was significantly better than that under alkaline and acidic conditions[33].

4.5 Soil solid phase component

Organic matter and minerals are the most important solid phase components in soil, which have large specific surface area and abundant functional groups, and affect the migration, transformation and fate of PAHs at the soil multiphase interface through physical adhesion and various chemical actions, thus affecting the photocatalytic degradation of PAHs.

4.5.1 Soil organic matter

The photocatalytic degradation of PAHs in soil often takes longer time than that in water, and the adsorption of organic matter on pollutants is an important reason. The existence of organic matter in soil provides a large number of adsorption sites, which makes PAHs closely combine with organic matter. Wang et al. Found that the higher the content of soil organic matter, the more the water-soluble and acid-soluble PAHs gradually changed to the stable bound and locked state[51]. Similarly, the longer the PAHs remain in the soil, the higher the content of bound and locked PAHs, and the more difficult it is to desorb them from the organic matter, thus increasing the difficulty of degradation[52,53]. It is worth noting that humic acid with photosensitive properties can enhance the charge transfer on the surface of the catalyst, promote the formation of active substances and accelerate the catalytic reaction rate[54⇓~56]. Zhang et al showed that the photocatalytic degradation rates of phenanthrene, pyrene and benzo (a) pyrene were effectively improved after adding a proper amount of humic acid[30].

4.5.2 Soil Mineral

Soil minerals are the main components of soil solid matrix, accounting for more than 95% of soil dry weight. The surface of soil minerals has abundant pores and functional groups, which are easy to compete with the photocatalyst for the adsorption of PAHs and inhibit the degradation of PAHs. On the other hand, studies have shown that clay minerals such as goethite, hematite and birnessite, which naturally occur in soil, have certain photocatalytic activity and can directly or indirectly act as photocatalysts for the degradation of PAHs in soil, possibly promoting the degradation of PAHs[21][34][57].

5 Conclusion and prospect

In this paper, we summarized the literatures in the field of photocatalytic remediation of PAHs in soil in the past two decades, and a large number of studies have proved that photocatalytic materials can efficiently degrade PAHs in soil and reduce their biological toxicity.Moreover, humic acid and minerals naturally existing in soil can effectively accelerate the photocatalytic degradation process, which indicates that photocatalytic technology has a very broad application prospect in the field of soil remediation. However, the application of this technology in the field of soil remediation still has the following challenges: First, the types of catalysts need to be broadened. Many photocatalytic materials with large specific surface area, high visible light response and high carrier separation have been widely used in the degradation of organic pollutants in water, but less used in soil research. Secondly, the comparability of research data needs to be improved. Compared with water, the chemical composition of soil environment is more complex, which leads to poor comparability of research data and is not conducive to the screening of highly active catalysts. Finally, the migration and transformation law of PAHs in soil, the action mechanism of photocatalyst on PAHs, the impact on soil environment, and how to increase the contact opportunity between photocatalyst and pollutants, reduce carrier recombination, and effectively recover photocatalyst need to be further studied.

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Funding

National Natural Science Foundation of China(51672047)

Natural Science Foundation of Fujian Province(2019J01648)

Foundation of Fujian Educational Committee(JAT190055)

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