Enhanced Wet Air Oxidation of Benzene by the Addition of Phenol

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Enhanced Wet Air Oxidation of Benzene by the Addition of Phenol Basim Abussaud, * Ihsanullah, Dimitrios Berk, and George J. Kubes Ind. Eng. Chem. Res., Just Accepted Manuscript • DOI: 10.1021/acs.iecr.9b01720 • Publication Date (Web): 15 May 2019 Downloaded from http://pubs.acs.org on May 21, 2019

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Industrial & Engineering Chemistry Research

Enhanced Wet Air Oxidation of Benzene by the Addition of Phenol Basim A. Abussaud a*, Ihsanullah b, Dimitrios Berk c, and George J. Kubes c

a

Department of Chemical Engineering, King Fahd University of Petroleum & Minerals (KFUPM),

Dhahran 31261, Saudi Arabia b Center

for Environment & Water (CEW), Research Institute, King Fahd University of Petroleum &

Minerals (KFUPM), 31261, Saudi Arabia c Department

*To

of Chemical Engineering, McGill University, Montreal, Québec, H3A-2B2, Canada

whom correspondence should be addressed. Tel.: (96613) 860-7514. Fax: (96613) 8604234. E-mail: [email protected].

1 ACS Paragon Plus Environment

Industrial & Engineering Chemistry Research 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

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ABSTRACT The wet air oxidation of benzene in the presence of phenol has been studied in an autoclave with a working volume of 1.24 L in the operating temperature range of 160-220C at 1.72 MPa oxygen partial pressure. The initial benzene concentration was kept constant at 5.63 mmol/L, while the phenol concentration was varied from 0 to 200 mg/L and 100% excess of oxygen was used. The effect of temperature and phenol concentration was studied on the oxidation of benzene at pH 6. The addition of phenol to the system has significantly enhanced the degradation of benzene. The benzene oxidation was found to increase with an increase in the concentration of phenol. However, the rate of benzene degradation remains constant after the optimum concentration of phenol is reached. Benzene degradation increased with a rise in temperature. It was found that 100% degradation of benzene (5.63 mmol/L) was achieved in 30 minutes at pH 6, temperature of 200oC and 1.72 MPa oxygen partial pressure in the presence of phenol (25 mg/L) and 100% excess O2. It was concluded that the degradation of benzene proceeds in two stages and the activation energy was calculated to be 21.1 KJ/mol and 1.2*102 KJ/mol for the fast and slow step, respectively.

Keywords: Wet air oxidation; Benzene; Phenol; Wastewater treatment; Co-oxidation; Free radicals.


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1. INTRODUCTION Volatile organic compounds (VOCs) emitted from various industrial operations have been recognized as one of the major contributors to air pollution

1,2.

The major sources of VOCs are

chemical industries, textile manufacturers, automobile industries, pharmaceutical plants, fuel combustions, petroleum refineries food processing, paper production, and household activities 3,4.

In addition, some household activities and indoor sources also contribute to the emission of

VOCs such as leaks from piping, wood stoves, pressed woods, insulating materials, heat exchanger systems, printers, office supplies and household products4–8. The most common VOCs are aromatic compounds, ketones, alcohols, aldehydes, halogenated compounds, and ethers 4. Many VOCs have been reported to have significant adverse impacts on human health and environment

3–9.

For example, benzene, chloroethylene, formaldehyde and

chloroform are carcinogenic and detrimental to the public health 3,10–12. Therefore, it is crucial to minimize the emission of VOCs. A number of techniques have been reported to be employed for the removal of VOCs such as membrane separation, wet scrubbing, condensation, incineration, adsorption, plasma oxidation and bioreaction

3,13–15.

However, these technologies still exhibited some disadvantages or

limitations, for the treatment of VOCs containing waste streams. Among the available technologies, the catalytic oxidation of VOCs is the most commonly used techniques due to its versatility and ability to handle a wide range of organic compounds 4. Wet air oxidation (WAO) that refers to liquid phase reactions between organic pollutants and oxygen under subcritical conditions (i.e., 125–320 °C, 0.5–22MPa of air) 16 was first patented by Zimmermann

17,

by oxidizing them into small molecules, non-toxic or low toxic substances

18.

WAO has been extensively employed for the degradation of a number of organic compounds



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such as phenol 19–21, acetic acid 19, ammonia 22 and paracetamol 23. In the current study, benzene is chosen as the representative VOCs due to its high toxicity and photochemical activity. WAO of benzene in the presence of phenol was found to an effective technique for the degradation of benzene24. Typically, in the WAO, the wastes are converted to H2O, CO2 and low molecular weight acids. In order to increase the effectiveness of the WAO, numerous methods have been reported. One of these methods is the catalytic wet air oxidation in which either homogenous or heterogeneous catalysts were used to enhance the degradation of organic compounds18–20,22,23. The performance of the wet oxidation method can also be enhanced by using ozone hydrogen peroxide26–28 as an oxidizing agent. Supercritical oxidation

29

25

or

was also found to

improve the oxidation of some compounds. Modifying the pH of the solution also enhances the WAO of many compounds

30,31.

The co-oxidation method was reported to be one of the

promising methods that can be used to enhance the WAO 32–34. In this paper, the wet air oxidation of benzene in the presence of phenol was studied in a stainless-steel laboratory rocking autoclave. The effect of temperature and phenol concentration was studied on benzene degradation. The effect of temperature on the phenol oxidation was also studied. Experimental data of benzene degradation was described by the pseudo-first-order kinetic model.


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2. EXPERIMENTAL METHODS 2.1. Materials and Reagents Benzene (ACS grade, 99.9% pure) and Phenol (ACS grade) were supplied by Fisher Scientific and J.T Baker, USA, respectively. Oxygen (oxidant, 99.6% pure) and Helium (inert gas, 99% pure) were acquired from BOC Gases in Montreal Canada. 2.2. Experimental Set up Experiments were performed in a stainless steel laboratory rocking autoclave with a working volume of 1.24 L, as shown in Figure 124. Schematic diagram of the WAO system is presented in Figure 2. A heating coil (1600 W) was used inside an autoclave shell to heat supply to the bomb. The autoclave is rocked by a small motor through approximately thirty degrees to ensure proper mixing. A temperature process controller in conjunction with a thermocouple is used to control the temperature to an accuracy of ±2Co. The sampling line was immersed in the reaction mixture and attached to the capillary tubing. A pressure safety valve is also installed to make sure of the safety of the equipment.



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Figure 1. Schematic diagram of the reactor

Figure 2. Schematic representation of the experimental system


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2.3. Experimental Procedure Benzene (5.63 mmol) and a variable amount of phenol were added to 1L of water and stirred for about 1 hr. The solution was then fed to the reactor, and the reactor was sealed. After connecting all the auxiliary components, the reactor was purged with helium in order to remove any traces of oxygen in the reactor. Furthermore, to keep the effluent in the liquid phase, helium was then introduced to the system prior to heating. The autoclave was preheated for about 75 minutes to minimize the time required to reach the desired temperature and the reactor was placed inside the autoclave. The system was further heated within the operating temperature range of 160-220C until the desired temperature is attained. Once the desired temperature was attained, the reactor was pressurized with O2 and this was noted as time zero for the reaction. Simultaneous wet oxidation of benzene and phenol was carried out in the temperature range 160-220C at 1.72 MPa oxygen partial pressure. The initial benzene concentration was kept constant at 5.63 mmol/L, while the phenol concentration was varied from 0 to 200 mg/L and 100% excess of oxygen was used. The liquid sample was collected from the reactor at different interval of time and analyzed by Gas Chromatograph (GC) to measure the benzene and phenol concentrations. This procedure was repeated at different temperatures and initial phenol concentrations.

3. RESULT AND DISCUSSION 3.1. Effect of Phenol Concentration on Oxidation of Benzene The WAO of benzene was examined at different phenol concentrations ranging from 0 to 200 mg/L in order to evaluate the effect of the initial phenol concentration on the oxidation of benzene. These experiments were performed at a temperature of 220oC, pH 6, oxygen partial



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pressure of 1.72 MPa and with 100% excess of O2. The benzene concentration was kept constant at 5.63 mmol/L in all the experiments. The results are displayed in Figure 3. It was observed that in the absence of phenol, benzene is very resistant to the oxidation and it takes a long time to be oxidized. However, the addition of phenol enhanced the degradation of benzene dramatically. While practically no benzene degradation was achieved in the first 15 minutes in the absence of phenol, more than 95% degradation of benzene was accomplished even with a very small amount (i.e. 25 ppm) of phenol. Also, it can be perceived that as the initial phenol concentration increases, the fastest benzene degradation occurs, especially during the first 5 minutes of the experiment. After 15 minutes, the degradation rates were comparable. However, when the initial phenol concentration was increased from 150 to 200 mg/L, no significant change in the degradation rate of benzene was observed. This can be attributed to the free radicals and the active intermediates that might be formed during the phenol degradation, and their concentration might increase with the increasing initial phenol concentration. The same trend was observed by Fu et al. 34 in their study of the degradation of nitrobenzene enhanced by phenol. The effect of the initial phenol concentration on the degradation of benzene at 200oC is presented in Figure 4 with 100% excess O2. It was observed that at a lower temperature (200oC), the benzene degradation is lower compared to a higher temperature (220oC), for the same initial phenol concentration.


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1 0.9

10 ppm Phenol 25 ppm Phenol 50 ppm Phenol 100 ppm Phenol 150 ppm Phenol 200 ppm Phenol 0 ppm Phenol

0.8

C/Co of C6H6

0.7 0.6 0.5 0.4 0.3 0.2 0.1 0 0

2

4

6

8

10

12

14

Time (min)

Figure 3. Effect of initial phenol concentration on the degradation of benzene (Initial concentration of benzene, C0=5.63 mmol/L, T= 220oC, 100% excess O2, pH=6, PO2= 1.72 MPa) 1 25 ppm Phenol 50 ppm Phenol

0.9 0.8 0.7 C/Co of C6H6

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


0.6 0.5 0.4 0.3 0.2 0.1 0 0

5

10

15

20

25

30

35

Time (min)

Figure 4. Effect of initial phenol concentration on the degradation of benzene ((Initial concentration of benzene, C0=5.63 mmol/L, T= 200oC, 100% excess O2, pH=6, PO2= 1.72 MPa)



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3.2. Effect of Temperature on Benzene Degradation The degradation of benzene was studied at different temperatures using two different initial phenol concentrations. The initial phenol concentration selected was 25 mg/L, which was the lowest phenol concentration that offered significant benzene degradation at the lowest temperature, i.e. 200oC. However, phenol concentration of 50 mg/L was used when the experiments were performed at the lowest temperature i.e 160oC. The oxygen concentration was kept at 100% excess and the initial pH was 6. Figure 5 illustrates the degradation of benzene at both 200 and 220oC with 25 mg/L of phenol concentration. It is apparent that when the temperature was increased from 200 to 220oC, much faster degradation was achieved. The cooxidation of benzene was further studied with the initial phenol concentration of 50 mg/L at four different temperatures ranging from 160 to 220oC. The results presented in Figure 6 show that benzene degradation was very slow at 160oC and only around 50% of degradation was achieved within 1 h. However, as the temperature increased, the degradation rate of benzene became faster and almost 100% of degradation was achieved in 30 minutes. This implies that the higher the temperature, the faster the phenol oxidation. This might be due to the faster formation of free radicals and active intermediates.


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1 0.9

T= 200 C T= 220 C

0.8

C/Co of C6H6

0.7 0.6 0.5 0.4 0.3 0.2 0.1 0 0

5

10

15

20

25

30

35

Time (min)

Figure 5. Degradation of benzene at different temperatures (Initial concentration of benzene, C0=5.63 mmol/L, 100%excess O2, 25 ppm phenol, pH=6, PO2= 1.72 MPa)

1 T= 220 C T= 200 C T= 180 C T= 160 C

0.9 0.8 0.7 0.6 C/Co

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


0.5 0.4 0.3 0.2 0.1 0 0

10

20

30

40

50

60

70

Time (min)

Figure 6. Effect of temperature on the degradation of benzene (Initial concentration of benzene C0=5.63 mmol/L, 100% excess O2, 50 ppm phenol, pH=6, PO2= 1.72 MPa)



3.3. Effect of Temperature on Phenol Oxidation The effect of temperature on the phenol oxidation was studied at different temperatures with an initial phenol concentration of 0.53 mmol/L, as presented in Figure 7. It is obvious that the degradation of phenol was faster at 220oC; however, at 200oC, the concentration of phenol decreased during the first 5 minutes of the oxidation, and then it increased slightly, and this was followed by final degradation of phenol. The same oxidation path can also be observed at 180oC. This shows that at the beginning of the oxidation, the small amount of phenol was degraded, and it was followed by the partial conversion of benzene to phenol, which was then further oxidized. However, the process path was slightly altered due to the change in the reaction temperatures. At 160oC, the concentration of phenol was increased with time, which means that the rate of oxidation of benzene to phenol was faster than the rate of degradation of phenol during the duration of the experiment. 2 1.8 1.6 1.4

C/Co of phenol

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

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1.2

T= 160 T= 180 T= 200 T= 220

1 0.8 0.6 0.4 0.2 0 0

10

20

30 Time (min)

40

50

60

Figure 7. C/Co of phenol vs. time (Initial concentration of phenol, C0=0.53 mmol/L 100% excess O2, pH=6) 12 ACS Paragon Plus Environment

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3.4. Reaction Kinetics of Benzene Oxidation Material balance for benzene in a batch reactor is represented by: dCb/dt = - kCb

(1)

where Cb is the concentration of benzene, k the reaction coefficient, t the time. Equation 1 can be integrated to yield:

ln (Cb/Cbo) = -kt

(2)

Where Cbo is the initial benzene concentration. The reaction constant k can then be related to the reaction temperature according to the Arrhenius equation

k= A exp (-E/RT)

(3)

where E is the activation energy, A the frequency factor, T the temperature, and R the gas constant. Pseudo-first-order kinetic model was used to describe the experimental data of benzene degradation. It can be seen from Figure 8 that the benzene degradation is well fitted by this model. It can be concluded from the plot that the reaction consists of 2 steps; namely the fast reaction step and the slow reaction step. It can be seen from Figure 8 that at 220oC only the faster step can be detected, at 160oC only the slow step exists. The Arrhenius plot for the pseudo-first-order rate constant for benzene degradation is presented in Figure 9. From the plot, values of the Arrhenius correlation and the activation energy were calculated to be 21.1 KJ/mol and 1.2*102 KJ/mol for the fast and slow step, respectively. 13 ACS Paragon Plus Environment


4 220 fast 200 solw 180 slow 160 slow 200 fast 180 fast

3.5 3

-ln(Cb/Cbo)

2.5 2 1.5 1 0.5 0 0

5

10

15

20

25

30

35

40

45

50

-0.5 Time (min)

Figure 8. Pseudo-first-order kinetic plot for benzene degradation

-0.00235

-0.0023

-0.00225

-0.0022

-0.00215

-0.0021

-0.00205

y = 2538.4x + 4.0219 R2 = 0.9845

0 -0.002 -1 -2 -3 -4

ln k

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

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y = 14471x + 28.367 R2 = 0.9496

slow stage Fast stage Linear (slow stage) Linear (Fast stage)

-5 -6 -7 -8 -9 -10

1/T (K)

Figure 9. Arrhenius plot for pseudo-first-order rate constant calculated from benzene degradation data


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3.5. Proposed Pathway for Oxidation of Benzene Based on the experimental data and GC analysis, a simplified pathway for oxidation of benzene is proposed, as presented in Figure 10. The benzene is first oxidized to phenol and then the phenol is degraded to either hydroquinone or catechol, or both, which was further degraded to the benzoquinone. The benzoquinone is further oxidized through many intermediates that have not been completely identified in this study. However, the results illustrate that the main intermediates were found to be acetic acid and formic acid. Negligible amounts of both propanoic acid and glycolic acid were also detected. In addition, a small amount of benzoquinone was also identified by the GC. Most of the intermediates were degraded to low molecular weight organic acids, CO2 and H2O as the reaction proceeded.

Figure 10. Proposed Pathway for Oxidation of Benzene

4. CONCLUSION The experimental data indicated that the presence of phenol to the system has significantly enhanced the degradation of benzene. This might be due to the free radicals that have been



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produced from the oxidation of phenol and act as an initiator for the oxidation of benzene. Also, the results demonstrate that the benzene was first converted to phenol before it further oxidized to the final products. The benzene oxidation was found to increase with an increase in the concentration of phenol. However, the rate of benzene degradation remains constant after the optimum concentration of phenol is reached. The benzene degradation was found to increase with an increase in temperature. It was found that 100% degradation of benzene was achieved in 30 minutes at pH 6, the temperature of 200oC, phenol concentration of 25 mg/L and 100% excess O2. This process could have a substantial economic impact by utilizing the commonly present phenol in the waste streams, as an initiator for the degradation of benzene.

Acknowledgement The authors gratefully acknowledge the Department of Chemical Engineering, McGill University, Montreal, Québec, Canada for their laboratory support in this research work and the support from King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia. The acknowledgement also gratefully extended to the National Sciences and Engineering Research Council of Canada (NSERC) for their financial support.


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Enhanced Wet Air Oxidation of Benzene by the Addition of Phenol

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