Recovery of PhSO3K from Industrial Waste Based on Solid–Liquid

Article Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Recovery of PhSO3K from Industrial Waste Based on Solid−Liquid Equilibrium of the PhSO3K−K2CO3−H2O System Chen Meng-qi,# Xu Jie,# Wei Yan, and Hao Shuang-hong* Research Center of Agro-bionic Engineering & Tech. of Shandong Province, College of Chemistry & Pharm., Qingdao Agricultural University, Qingdao 266109 China

ABSTRACT: The primary aim of this study is to develop a recovery process for PhSO3K from the industrial waste of Qpe (quizalofop-p-ethyl) production. The solubility data for the PhSO3K−K2CO3−H2O system at 15, 25, 35, 45, and 55 °C were determined to obtain the phase diagram of the system. Moreover, the different crystallization fields in the phase diagram of 25 °C were analyzed. The separation technology of PhSO3K from the PhSO3K−K2CO3−H2O system was designed based on the phase diagram. Furthermore, the PhSO3K and K2CO3 in a wastewater from Qpe production were crystallized in sequence by evaporation according to the designed method. The organic impurities precipitated concomitantly with PhSO3K were washed out by ethanol. Finally, the purified PhSO3K was converted to (R)-ethyl O-bezenesulfonyl lactate, the intermediate of Qpe production.

1. INTRODUCTION Quizalofop-p-ethyl (Qpe; ethyl (R)-2-[4-(6-chloroquinoxalin-2yloxy) phenoxy] propionate) is a member of the aryloxyphenoxypropionate (AOPP) group of herbicides.1 Qpe is a selective postemergence herbicide that can be used to effectively control annual and perennial grass weeds in crops of potatoes, sugar beets, soy beans, peanuts, oilseed rape, sunflowers, vegetables, cotton, flax, and other broad leafed plants (Min, 2003; Shaw, 1994; Mahakavi et al., 2014).2−4 Qpe has been one of the most widely used herbicides over the world, due to its application in causing chlorosis and necrosis in target plants and eventually death (Gherekhloo et al., 2011; Wu et al., 2017).5,6 Qpe inhibits fatty acid synthesis by blocking the acetyl-Co-A carboxylase enzyme (Tang et al., 2014).7 Furthermore, it has a low risk of contaminating adjacent water resources because of its short half-life (0.5−0.7 days), and penetrating into the soil no more than 10 cm (Sumera et al., 2017).8 In addition, it shows limited transformation from broad-leaved plants such as rapeseed and sunflower (Guan and Zhang, 2013; Mantzos et al., 2016).9,10 Qpe is usually reported to be produced by the reaction of (R)-ethyl O-p-toluenesulfonyl lactate (1) with 4-(6-chloroquinoxalin-2-yloxyl) phenol (2) in the presence of excess acid binding agent K2CO3 (Wang et al., 2017; Yang et al., 2016; Korea Research Institute of Chemical Technology, 2004).11−13 In fact, in order to reduce the production cost, some factories in © XXXX American Chemical Society

China use (R)-ethyl O-bezenesulfonyl lactate (3) instead of (1) to manufacture Qpe. Normally, the molar ratio of K2CO3 to 2 is about 2:1. That is, if one molar of Qpe is manufactured, one molar of PhSO3K and KHCO3 would be produced as byproduct simultaneously. Thus, the PhSO3K, KHCO3 and another molar of excess K2CO3 as waste solid exist in the system. In summary, industrial production of Qpe will inevitably produce mass waste of PhSO3K + KHCO3 + K2CO3. The benzenesulfonic acid type chemicals are highly toxic, water-soluble, and difficult to biodegrade, so PhSO3K in the waste of Qpe production should be recovered instead of being discarded. Commissioned by a factory in China, the recovery of PhSO3K and K2CO3 in the wastewater from Qpe production was studied in this paper. PhSO2Cl is the raw material to prepare the intermediate (3) for producing Qpe. Though there is no report for converting PhSO3K to PhSO2Cl, preparation of PhSO2Cl from PhSO3H or PhSO 3 Na could be carried out by using phosphorus pentachloride (PCl5), phosphoryl chloride (POCl3), thionyl chloride (SOCl2), triphenylphosphine dichloride, (Tadashi et al., 1998)14 or 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) (Grzegorz, 2003).15 Among the several methods, the method Received: November 15, 2017 Accepted: April 4, 2018

A

DOI: 10.1021/acs.jced.7b00998 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

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Table 1. Chemical Sample Information chemical name

CASRN

source

state

initial mass fraction

K2CO3 KOH PhSO3H PhSO3K HCl ethanol SOCl2 dimethylformamide toluene L-ethyl lactate triethylamine anhydrous Na2SO4

584-08-7 1310-58-3 98-11-3 934-55-4 7647-01-0 64-17-5 7719-09-7 68-12-2 108-88-3 687-47-8 121-44-8 7757-82-6

Sinopharm Chemical Reagent Co., Ltd. Sinopharm Chemical Reagent Co., Ltd. Aladdin Reagent Co., Ltd. Self-made Sinopharm Chemical Reagent Co., Ltd. Laiyang Kangde Chemical Co., Ltd. Sinopharm Chemical Reagent Co., Ltd. Sinopharm Chemical Reagent Co., Ltd. Laiyang Kangde Chemical Co., Ltd. SA Chemical Technology Co., Ltd. Sinopharm Chemical Reagent Co., Ltd. Laiyang Kangde Chemical Co., Ltd.

solid solid solid solid liquid liquid liquid liquid liquid liquid liquid solid

0.99 0.95 0.98 0.99 0.36−0.38 (analytical reagent) 0.99 0.99 0.99 0.99 0.98 0.99 0.99

(DDW) with a conductivity of ≤1.2 × 10−4 S·m−1. There is no PhSO3K in the market, and it was prepared by the reaction of PhSO3H with KOH according to the method of Zhao et al. (2013).17 The synthesized PhSO3K was recrystallized three times with DDW to give the final product of 99.0% detected by HPLC. 2.2. Experimental Method. The solubility of the samples was determined by the method of isothermal solution saturation (Du et al., 2006).18 The solid phase was measured by Screinemaker’s method and confirmed by X-ray diffraction (Nouri et al., 2017).19 The specific experiment procedures were as follows: (a) The samples with specified component ratios of PhSO3K, K2CO3, and DDW were prepared and loaded into sealed conical flasks (250 mL) and placed in the corresponding shaking bath. The equilibrium process was carried out at ambient pressure and five fixed temperatures of 15, 25, 35, 45, and 55 °C. (b) The samples were shaken for 24 h and then stayed for at least 12 h to ensure that the suspended crystals in the system had fully settled. It is noted that there should always exist solid phase in the bottle during the equilibrium process. An appropriate amount (2−3 mL) of the supernatant solution in the system was carefully sucked out with a syringe filter, and its composition was determined. The equilibrium was roughly considered to be reached when two continual analyses gave identical results. Otherwise, the system was rotated continually until equilibrium was achieved. It usually takes about 15 days to achieve the equilibrium state. (c) After equilibrium, the liquid phase and solid phase in the system were taken out and determined, respectively. PhSO3K was quantitatively analyzed with an UV spectrometer (Smith et al., 2011)20 (with a mass fraction uncertainty of 1.5%). K2CO3 was titrated by hydrochloric acid solution using phenolphthalein (Shen et al., 2013)21 or pH meter (Li and Lin, 2005)22 as indicator (with a mass fraction uncertainty of 0.4%). In addition, the solid phases were dried in desiccators at room temperature and then determined by X-ray diffraction analyzer.

using SOCl2 is widely employed (Shinsaku, 1982).16 As we know, the byproduct HCl and SO2 produced in the SOCl2 method would react with K2CO3 and KHCO3, therefore we need to separate out PhSO3K from the system beforehand. To the best of our knowledge, there is no report for PhSO3K separation from KHCO3 + K2CO3 or K2CO3. The phase diagram of solid−liquid equilibrium contains detailed information on solution composition and sequence of salts precipitation at different temperatures. Therefore, the phase diagram is an important basis for designing process flow and setting operation conditions of mixture separation. KHCO3 is thermally unstable, and its solubility in water is smaller than that of K2CO3. The solubility of PhSO3K in water is smaller than that of K2CO3 also. To simplify the separation process and recover more and pure K2CO3, the quaternary system of PhSO3K−KHCO3−K2CO3−H2O is converted to the ternary system PhSO3K−K2CO3−H2O by neutralization before separation. Studies of the phase equilibrium for the above quaternary and ternary systems have not been reported so far. In this study, much work was performed on the phase equilibrium of the K2CO3−PhSO3K−H2O system at 15, 25, 35, 45, and 55 °C, and the phase diagram of the above system at 25 °C was plotted. The separation technology of PhSO3K and K 2 CO 3 was determined. Furthermore, the process of intermediate (3) preparation from recycled potassium benzenesulfonate was studied.

2. EXPERIMENTAL SECTION 2.1. Apparatus and Reagents. An Agilent 1100 high performance liquid chromatography (HPLC, Agilent) was used to detect the purity of PhSO3K and (R)-ethyl O-bezenesulfonyl lactate. THZ-82 type isothermal shakers (Changzhou Guohua Electrical Equipment Co., Ltd.) with an accuracy of 0.1 °C set at 15 to 55 °C were used in the experiment to obtain the solid− liquid equilibrium. A TU-1901 UV−visible spectrometer (Beijing Purkinje General Instrument Co., Ltd.) was used to determine the PhSO3K. A DELTA 320 pH meter (Mettler Toldedo) was used as indicator for K2CO3 titration. The dried solid phase was ground to 0.05 mm and scanned from 2θ = 10° to 80° with a D8 ADVANCE X-ray diffractometer (Bruker AXS) set at 40 kV and 40 mA. A Bruker Avance III HD 500 MHz nuclear magnetic resonance instrument (Bruker) was used to record the 1H NMR spectra in CDCl3 using tetramethylsilane (TMS) as the internal standard. All chemicals employed are commercially available and without further purification. The chemical sample information is listed in Table 1. The water used was doubly distilled water

3. RESULTS AND DISCUSSION 3.1. Solubility Isotherms of PhSO3K in K2CO3 Aqueous Solutions. Equilibrium data of the ternary system PhSO3K− K2CO3−H2O at 15, 25, 35, 45, and 55 °C are presented in Table 2. On basis of the data, the solubility isotherms saturated with solid PhSO3K are depicted in Figure 1. The solubility isotherms at different temperatures show similar tendency. With the content of K2CO3 increasing, the solubility isotherms of PhSO3K decrease remarkably in the figure. That is, the salting-out effect of K2CO3 on PhSO3K is very strong. It is B

DOI: 10.1021/acs.jced.7b00998 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 2. Equilibrium Data for the PhSO3K−K2CO3−H2O System from 15 to 55 °C and at Pressure p = 0.1 MPa

a

liquid phase, 100·w no.

K2CO3

PhSO3K

1 2 3 4 5 6 7 8 9 10 11

0 2.66 4.86 7.27 9.09 12.66 15.18 21.49 25.36 34.36 45.12

30.76 28.26 24.26 21.64 19.94 15.38 13.53 8.97 7.32 3.52 1.08

1, F 2 3 4 5 6 7 8 9 10, E

0 2.15 4.95 6.77 10.55 17.41 28.07 30.99 38.72 45.91

33.87 31.15 28.38 26.90 20.62 13.91 7.76 6.31 3.00 1.87

1 2 3 4 5 6 7 8 9 10 11

0 1.89 6.9 9.82 13.68 18.45 20.83 25.07 33.34 43.03 46.12

36.75 35.15 30.21 25.72 21.25 16.57 14.69 10.19 5.46 3.02 2.11

1 2 3 4 5 6 7 8 9 10 11

0 5.39 7.72 11.9 16.85 19.08 25.57 27.89 31.87 34.89 47.65

37.82 33.64 30.92 25.82 20.41 18.94 13.45 10.98 7.98 5.9 2.39

1 2 3 4 5 6 7 8 9 10 11

0 5.23 10.56 12.73 16.34 21.08 24.92 29.89 32.87 35.89 48.96

39.42 34.64 29.82 28.34 24.41 19.94 15.58 11.34 8.98 6.88 3.34

H2O 15 °C 69.24 69.08 70.88 71.09 70.97 71.96 71.29 69.54 67.32 62.12 53.80 25 °C 66.13 66.7 66.67 66.33 68.83 68.68 64.17 62.70 58.28 52.22 35 °C 63.25 62.96 62.89 64.46 65.07 64.98 64.48 64.74 61.2 53.95 51.77 45 °C 62.18 60.97 61.36 62.28 62.74 61.98 60.98 61.13 60.15 59.21 49.96 55 °C 60.58 60.13 59.62 58.93 59.25 58.98 59.5 58.77 58.15 57.23 47.7

C

solid phases PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K + K2CO3·1.5H2O PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K

(A) (A) (A) (A) (A) (A) (A) (A) (A) (A) + K2CO3·1.5H2O (C)

PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K + K2CO3·1.5H2O PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K + K2CO3·1.5H2O PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K PhSO3K + K2CO3·1.5H2O

DOI: 10.1021/acs.jced.7b00998 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 2. continued a

Standard uncertainties u, u(T) = 0.1 °C, u(p) = 0.005 MPa, u(w(K2CO3)) = 0.004, and u(w(PhSO3K)) = 0.015.

Figure 2. Phase diagram of the PhSO3K(A)−K2CO3(B)−H2O system at 25 °C.

Figure 1. Solubility isotherms of PhSO3K in K2CO3 aqueous solution respectively at (■) 15 °C; (●) 25 °C; (▲) 35 °C; (▼) 45 °C; and (★) 55 °C. Only points with the solid phase of PhSO3K are drawn.

apparent that the separation of PhSO3K can be achieved by the salting-out method. Furthermore, though the solubility of PhSO3K decreases with the decrease of temperature, the decline degree is limited. Therefore, evaporating crystallization is chosen as a preferential way for the PhSO3K separation. The ratios of PhSO3K to K2CO3 of saturated points at 15, 25, 35, 45, and 55 °C in Table 2 are 2.39%, 4.07%, 4.58%, 5.02%, and 6.82%, respectively. To keep K2CO3 just saturated to remain in the solution while PhSO3K is crystallized, the above data indicate that the temperature order of the PhSO3K mass precipitated from the sample solution should be 15, 25, 35, 45, and 55 °C. Because 25 °C is the appropriate temperature to realize in industry, the phase diagram and separation process at this temperature are studied further. The phase diagram of 15 or 35 °C could be chosen according to the ambient temperature. 3.2. Phase Diagram of PhSO3K−K2CO3−H2O System at 25 °C. A temperature of 25 °C is normally used in industry, so the phase diagram of the system PhSO3K−K2CO3−H2O at 25 °C is illustrated (Figure 2). As shown in Figure 2, points A, B, and C represent the solids PhSO3K, K2CO3, and K2CO3· 1.5H2O, respectively. Points E and F locate on the solubility line. Point F represents the solubility of PhSO3K. Curve FE shows the equilibrium solid phase is PhSO3K (A). It is apparent that there is no saturated solubility line with anhydrous potassium carbonate (K2CO3) (B). Point E is invariant and saturated point, the composition of the solid phase is PhSO3K (A) and K2CO3·1.5H2O (C). The solid phase of point E is rechecked by the X-ray diffractometer, which is displayed in Figure 3. All the solid phases exist in the region of AECBA. The region of MFE indicates the unsaturated solution region. As shown in Figure 2, the crystalline region of PhSO3K is far larger than that of K2CO3·1.5H2O. It is obvious that PhSO3K is easy to separate from the system, and PhSO3K would crystallize first in the separation process.

Figure 3. X-ray diffraction of the equilibrium solid phase at point E: (a) PhSO3K sample; (b) K2CO3 sample; (c) sample of saturation point E.

3.3. Design of Salting out Process of PhSO3K. The phase diagram of PhSO3K−K2CO3−H2O system at 25 °C (Figure 2) indicates that PhSO3K could be separated out on the salt-out effect of K2CO3. The composition of saturated point E is PhSO3K 1.87%, K2CO3 45.91%, H2O 52.22%, and the mass ratio of K2CO3 to PhSO3K in dry salt is 24.55. Thus, we can extrapolate that if the ratio of PhSO3K/K2CO3 is more than 1:24.55, the excess PhSO3K could be separated from the mixture of PhSO3K + K2CO3. That is, the water content of PhSO3K−K2CO3−H2O system should be proper to keep K2CO3 just unsaturated but to precipitate the excess PhSO3K. Taking a wastewater of Qpe production (from a factory of Shandong, China) as example, after neutralizing KHCO3 to K2CO3, the composition (PhSO3K 9.38%, K2CO3 9.24%, H2O 81.38%, 3.00% of organic impurities is counted as H2O to facilitate the calculations) is marked as point G in Figure 2. The ratio of PhSO3K to K2CO3 in the alkalized wastewater is 1.02, which is much more than 1:24.55 (ratio of point E), therefore, the excess PhSO3K could be separated. D

DOI: 10.1021/acs.jced.7b00998 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 3. Calculated Results of 1000 g of Quizalofop-p-ethyl Wastewater Separation PhSO3K calculated actual

K2CO3

H2O/g

m/g

yield/%

purity/%

m/g

yield/%

purity/%

impurities/g

708.7 708

90.0 92.3

95.9 98.4

100 98.0

92.4 85.6

100 92.6

96.0 97.1

30.0 29.6

Figure 4. 1H NMR spectra of L-lactate ethylbenzenesulfonate.

higher than that of the theoretical result. However, the purity of PhSO3K is lower than that of the theoretical value. 3.5. Synthesis of Benzenesulfonyl L-Lactate. The recovered PhSO3K 1.96 g (0.01 mol) was added to the solution of 200 μL of DMF in 15 mL of toluene, then 1.12 g (0.014 mol) SOCl2 was added dropwise at 0 °C to the mixture and was stirred for 30 min. Then the reaction mixture was heated to 55 °C and stirred for 3 h until a colorless transparent oil formed. When the reaction was completed, the excess SOCl2 and toluene were distilled off and recovered. Then, 15 mL of toluene, 1.8 mL (0.011 M) of triethylamine and 1.18 g (0.01 M) of L-ethyl lactate were added to the residue. The mixture was heated at 65 °C and stirred for 4 h. After the completion of the reaction, the mixture was filtered, and the resulting liquid was washed with distilled water (3 × 15 mL). The organic layer was dried with Na2SO4 and vacuum concentrated to obtain 2.31 g of (R)-ethyl O-bezenesulfonyl lactate (3) with yield of 92.5%.The purity of the obtained (R)-ethyl O-bezenesulfonyl lactate (3) was determined by HPLC, and the purity of 98.0% achieved the requirement of industrial production. Furthermore, the structure of the target chemical was validated by 1H NMR, which is shown in Figure 4.

When the wastewater is evaporated from G to E, K2CO3 remains in solution as the constant component, and PhSO3K would crystallize. On the basis of the composition of point E and point G, in combination with the material balance, the calculations of the salting out process from point G to point E is performed as follows (1000 g of alkalized wastewater): PhSO3K:

93.8 = x + 0.0187z

(1)

K 2CO3 :

92.4 = 0.4591z

(2)

813.8 − y = 0.5222z

(3)

H 2O:

x + y + z = 1000

(4)

In the equations, x and y represent the amount of PhSO3K precipitated and H2O evaporated from point G to point E, respectively. And z is the amount of residual solution. From the above equations, the x, y, and z can be obtained: x is 90.0 g, y is 708.7 g, and z is 201.3 g. The calculated results of evaparation process for 1000 g of alkalized wastewater is shown in Table 3. From the table, we can see that if 708.7 g of H2O evaporated from the 1000 g of alkalized wastewater, 95.9% PhSO3K could be separated and recovered. 3.4. Separation Scheme Application. A 1000 g sample of wastewater from Qpe production was weighed and 708 g was distilled (Table 3). The obtained system was mechanically stirred to 25 °C and stayed at the temperature to equilibrate for 2 h. Then the mixture was vacuum filtered quickly and drained as far as possible. The solid was dried and washed with 210 mL of warm ethanol to obtain 92.3 g of PhSO3K. The recovery rate of PhSO3K is 98.4%, and the purity is 98.0%. The liquid was concentrated and dried, then washed with 110 mL of warm ethanol to obtain 85.6 g of K2CO3 with a recovery of 92.6% and a purity of 97.1%. It reveals that the recovery of PhSO3K is

4. CONCLUSIONS The equilibrium data of the PhSO3K−K2CO3−H2O system at 15, 25, 35, 45, and 55 °C were determined, and the phase diagram of the system at 25 °C was plotted. The solubility isotherms show that the solubility of PhSO3K decrease remarkably with the concentration of K2CO3 increasing. Moreover, evaporating crystallization is chosen as a preferential way for the separation of PhSO3K from the system. According to the phase diagram, a wastewater with the PhSO3K−K2CO3−H2O system from Qpe production was E

DOI: 10.1021/acs.jced.7b00998 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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evaporated and crystallized in stages. The final recovery and purity of PhSO3K from the wastewater are 98.4% and 98.0%. The recovery and purity of K2CO3 are 92.6% and 97.1%, respectively. The recovered PhSO3K was further converted to benzenesulfonyl chloride, and finally to the intermediate (R)-ethyl Obezenesulfonyl lactate (3) for Qpe production. The yield and purity of the product are 92.5% and 98.0%. The obtained (R)ethyl O-bezenesulfonyl lactate (3) achieve the requirement of industrial production.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. ORCID

Hao Shuang-hong: 0000-0002-9458-5112 Author Contributions #

C.M.-q. and X.J. contributed equally to this article.

Funding

This work is supported by Chinese National Undergraduate Training Program for Innovation (No. 201510435015), partially by National Nature Science Foundation of China (No. 31471808) and National Nature Science Foundation of China (No. 21706142). Notes

The authors declare no competing financial interest.

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DOI: 10.1021/acs.jced.7b00998 J. Chem. Eng. Data XXXX, XXX, XXX−XXX