Investigation on recovery of p-mephso3k based on solid-liquid equilibrium of the p-mephso3k-k2co3-h2o system

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Investigation on Recovery of p‑MePhSO K Based on Solid−Liquid

Equilibrium of the p ‑MePhSO K −K CO −H O System

†

Xu Jie, Chen Mengqi, Wei Yan, and Hao Shuanghong*

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ABSTRACT: In this article, we propose a method of recovering p-MePhSO K from the industrial by-product of quizalofop-p-ethyl.

The phase diagram of the solid−liquid equilibrium system of p-MePhSO K CO −H O at the temperatures of 15, 25, 35, 45, and 55

C was determined and plotted. Based on the phase diagram of 25 °C, the separation and recovery process of p-MePhSO K from the

p-MePhSO K CO −H O system was designed by analyzing the crystallization ﬁelds. First, p-MePhSO K and K CO were

crystallized from wastewater in turn through evaporation separation. Then, the crystallized p-MePhSO K was puriﬁed further by

washing with ethanol. Finally, the pure p-MePhSO K was transformed into the intermediate p-toluenesulfonyl chloride and then the

intermediate L-p-toluenesulfonate ethyl lactate for quizalofop-p-ethyl production.

. INTRODUCTION

quizalofop-p-ethyl wastewater by the general biochemical

method is high. This brings diﬃculties to the industry

production. Fortunately, there are reports of converting

benzene sulfonate to benzene sulfonyl chloride (Tadashi, et

Quizalofop-p-ethyl (C H ClN O ) is a selective post-

budding herbicide for upland ﬁelds, which has high herbicidal

activity and can control annual and perennial grass weeds

during any growth period of cotton, rape, soybean, peanut, and

13−15

al., 1998; Shinsaku, 1982; Grzegorz, 2003),

which oﬀer a

a variety of broad-leaved vegetable ﬁelds (Zhang et al., 2017).

possibility of recycling p-toluene sulfonate.

Quizalofop-p-ethyl has been widely used all over the world for

high eﬃciency, low toxicity, low residue, and good selectivity

and it meets the needs of users (Min, 2003; Shaw, 1994;

Mahakavi et al., 2014).

there are few herbicides suitable for vegetable ﬁelds except

dimethylpentylline. Therefore, quizalofop-p-ethyl can ﬁll the

gap (Gherekhloo, et al., 2011; Wu, et al., 2017). However,

treatment of wastewater from the production of the organic

pesticide quizalofop-p-ethyl is still a diﬃcult problem (Tang et

To solve this problem, we develop a method of recovering

potassium p-toluene sulfonate from wastewater in this study.

The potassium p-toluene sulfonate is recovered from the

wastewater by evaporation separation after alkalization. Then,

it is used to synthesize L-p-toluenesulfonate ethyl lactate, which

indirectly reduces the production cost of quizalofop-p-ethyl.

The recovery method is simple and easy to operate, which is

suitable for large-scale industrial production.

−4

According to pesticide registration,

al., 2014).

At present, p-toluene sulfonyl chloride is used as a raw

material in the production of quizalofop-p-ethyl (Guan and

Received: September 16, 2020

Accepted: January 19, 2021

Published: February 11, 2021

Zhang, 2013; Mantzos et al., 2016).

Thus, p-toluene

sulfonate exists in wastewater in the form of sodium salt or

potassium salt, resulting in a higher COD content (Wang, et

al., 2017; Yang, et al., 2016; Korea Research Institute of

0−12

Chemical Technology, 2004).

The cost of treating

2021 American Chemical Society

J. Chem. Eng. Data 2021, 66, 1249−1254

249

Journal of Chemical & Engineering Data

Article

Table 1. Chemical Sample Information

chemical name

CAS registry numbers

source

state

initial mass fraction

K CO₃

KOH

p-MePhSO H

p-MePhSO K

HCl

ethanol

SOCl₂

dimethylformamide

toluene

584-08-7

1310-58-3

104-15-4

16106-44-8

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.

Aladdin Reagent Co., Ltd.

solid

liquid

solid

0.99

0.95

0.98

0.99

self-made

Sinopharm Chemical Reagent Co., Ltd.

Laiyang Kangde Chemical 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.

0.36−0.38 (analytical reagent)

0.99

0.98

0.99

L-ethyl lactate

triethylamine

anhydrous Na SO

Table 2. Equilibrium Data for p-MePhSO K−K CO −H O from 15 to 55 °C at Five Diﬀerent Temperatures at Pressure p =

0.1 MPa

liquid phase, 100·w

p-MePhSO K

K CO

H O

solid phase, 100·W

p-MePhSO K

K CO₃

H O

solid phase, 100·W

66.11

66.85

69.25

68.96

70.03

69.55

70.40

69.29

70.06

68.05

66.84

63.41

63.23

63.54

63.81

63.38

65.28

64.48

66.13

65.65

64.36

59.70

5 °C

35 °C

3.89

9.67

4.48

1.73

7.87

5.89

2.57

.22

3.48

6.27

p-MePhSO K

10.78

8.67

5.67

2.45

30.45

32.78

37.23

45.45

58.77

58.55

57.10

52.10

p-MePhSO K

9.31

p-MePhSO K

p-MePhSO K + K CO ·1.5H O

12.10

14.56

17.03

21.49

27.27

30.85

34.42

p-MePhSO K

45 °C

p-MePhSO K

40.67

38.65

35.34

30.24

28.67

23.78

20.37

15.23

13.39

9.46

4.35

9.60

59.33

57.00

55.06

54.02

53.58

54.47

54.85

54.32

53.83

52.31

48.85

p-MePhSO K

.67

.10

.74

p-MePhSO K

15.74

17.75

21.75

24.78

30.45

32.78

38.23

45.45

p-MePhSO K

p-MePhSO K + K CO ·1.5H O

p-MePhSO K

5 °C

p-MePhSO K

6.59

3.49

0.15

5.09

0.59

6.23

4.56

0.60

.50

3.28

6.31

p-MePhSO K

11.10

16.03

18.49

20.96

23.27

28.85

32.34

38.46

p-MePhSO K

5.70

p-MePhSO K + K CO ·1.5H O

p-MePhSO K

55 °C

p-MePhSO K

42.14

38.68

35.90

30.24

28.57

24.26

21.49

15.78

12.67

8.67

7.35

57.86

53.97

51.50

51.02

50.68

50.99

50.73

50.77

51.55

48.10

46.10

p-MePhSO K

12.60

18.74

20.75

24.75

27.78

33.45

35.78

43.23

49.45

p-MePhSO K

.30

.84

p-MePhSO K + K CO ·1.5H O

p-MePhSO K

K CO ·1.5H O

p-MePhSO K

60.86

59.20

58.53

57.95

57.38

59.44

59.10

5 °C

p-MePhSO K

39.14

36.45

33.87

28.31

25.87

17.78

15.56

4.35

7.60

13.74

16.75

22.78

25.34

p-MePhSO K

4.45

p-MePhSO K + K CO ·1.5H O

3 2 3 2

p-MePhSO K

Standard uncertainties u, u(T) = 0.1 °C, u(p) = 0.005 MPa,

u(w(K CO )) = 0.004, and u(w(p-MePhSO K)) = 0.015.

p-MePhSO K

. EXPERIMENTAL SECTION

.1. Experimental Instrument and Reagents. In this

UV−Visible spectrometer (manufactured by Beijing Purkinje

General Instrument Co., Ltd.). As an indicator, the DELTA

20 pH meter (Mettler Toledo) was used in the K CO

2 3

experiment, the purity of p-MePhSO K and L-p-toluenesulfo-

titration.

nate ethyl lactate was analyzed by the Agilent 1100 high

performance liquid chromatography system (HPLC, Agilent).

The solid−liquid equilibrium of the system was obtained by

THZ-82 type isothermal shakers (Changzhou Guohua

Electrical Equipment Co., Ltd.) with an accuracy of 0.1 °C.

The solid phase was dried and milled to 0.05 mm. Then, it

was evaluated by a D8 ADVANCE X-ray diﬀractometer

(Bruker AXS) with the condition of 40 kV, 40 mA, and 2θ =

10 to 50°. H NMR spectra in CDCl

with tetramethylsilane as

The content of p-MePhSO K was detected by a TU-1901

the internal standard were obtained by the Bruker AVANCE

250

J. Chem. Eng. Data 2021, 66, 1249−1254

Journal of Chemical & Engineering Data

MePhSO K −K CO −H O at 25 °C is displayed in Figure 2 .

Article

III HD 500 MHz nuclear magnetic resonance instrument

(

Bruker).

The chemicals used in the experiment are commercially

available, and the speciﬁc information is shown in Table 1. The

−

−1

water with a conductivity of ≤1.2 × 10 S·m was doubly

distilled water (DDW). In addition, there is no p-MePhSO K

in the market. Thus, p-MePhSO K was obtained by the

reaction of p-toluene sulphonic acid with KOH referring to the

method of Zhao et al. (2013). Then, the synthesized p-

MePhSO K was separated and puriﬁed in the experiment for

subsequent analysis. The purify of p-MePhSO K was

determined by the UV spectrophotometry.

.2. Experimental Method. According to the method of

isothermal solution saturation (Du, et al., 2006 and Chen et al.,

7,18

018),

the solubility of samples was measured in this

study. The solid phase was determined by Screinemaker’s

method and conﬁrmed by X-ray diﬀraction (Nouri, et al.,

017). The whole experiment was carried out by the

following steps. (1) The samples with diﬀerent ratios of p-

Figure 1. Solubility isotherms of p-MePhSO K−K CO −H O from

MePhSO K, K CO , and DDW were prepared in a sealed

15 to 55 °C.

conical ﬂask (250 mL). Then, the samples were placed in the

corresponding shaking bath. The equilibrium experiments were

conducted at ambient pressure and the temperatures of 15, 25,

decreases slightly with the decreasing temperature, especially in

a high concentration K CO solution. Therefore, the

5, 45, and 55 °C. (2) The samples were shaken for 24 h.

evaporative crystallization is the best way to separate p-

Then, they were kept still for at least 12 h to make sure that the

suspended crystals in the system were sedimented. In the

equilibrium operation, there should always exist a solid phase

in the bottle. An appropriate amount (2−3 mL) of the

supernatant solution in the system was carefully sucked out

with a syringe ﬁlter, and its constitution was determined. When

two continual analyses gave identical results, the equilibrium of

the system was reached. Otherwise, the system was continued

to be rotated till the equilibrium was achieved. It generally

takes about 15 days to achieve the equilibrium state. (3) When

the system reaches the equilibrium, the solid phase and liquid

MePhSO K.

.2. Phase Diagram of the p-MePhSO K−K CO −H O

System at 25 °C. 25 °C is the appropriate temperature to

realize in industry, so the phase diagram of the system p-

phase were taken out and analyzed. p-MePhSO K was

quantitatively analyzed with the help of a UV spectrometer

(

Smith et al., 2011) (a mass fraction uncertainty of 1.5%).

K CO was titrated by hydrochloric acid solution using

phenolphthalein (Shen, et al., 2013) or a pH meter (Li

and Lin, 2005) as the indicator (with a mass fraction

uncertainty of 0.4%). Moreover, the solid phases were dried in

desiccators and then evaluated by X-ray diﬀraction.

. RESULTS AND DISCUSSION

.1. Solubility Isotherms of p-MePhSO K in K CO

Aqueous Solutions. The solubility of K CO is higher than

that of KHCO and p-MePhSO K. Thus, KHCO was reacted

with equivalent KOH to convert into K CO before separation.

Figure 2. Phase diagram of p-MePhSO K + K CO + H O at 25 °C.

3 2 3 2

The equilibrium data of the ternary system p-MePhSO K−

K CO −H O were measured three times, and the average

In the phase diagram, points A, B, and C represent the solids

values were obtained. Equilibrium data of the ternary system p-

MePhSO K−K CO −H O at 15, 25, 35, 45, and 55 °C are

p-MePhSO K, K CO , and K CO ·1.5H O, respectively.

Points E and F are located on the solubility line. Point E is

a co-saturation point. Point F represents the solubility of p-

MePhSO K. Point D represents the starting point that K CO ·

presented in Table 2. The data in Table 2 show the various

solubility values at diﬀerent temperatures. For example, when

the content of p-MePhSO K and H O are 33.89 and 66.11% in

1.5H O exists as the only substance exiting in the system. Point

the liquid phase, the solid phase is p-MePhSO K at 15 °C.

G represents the composition of the quizalofop-p-ethyl

wastewater. The phase diagram can be roughly divided into

Based on the data in Table 2, the phase diagram of p-

MePhSO K−K CO −H O was drawn and is shown in Figure

ﬁve zones: the saturated crystallization zone of p-MePhSO K

. The solubility isotherm of p-MePhSO K decreases with the

(AFE), the saturated crystallization zone of K CO ·1.5H O

increase in K CO concentration. That is to say, K CO has a

(EDC), the p-MeSO K and K CO ·1.5H O crystallization

3 2 3 2

remarkable salting-out eﬀect on p-MePhSO K. It can be

zone (AEC), the p-MePhSO K and K CO eutectic zone

3 2 3

concluded from Figure 1 that the solubility of p-MePhSO K

(ACB), and the unsaturated solution zone (FOD).

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Journal of Chemical & Engineering Data

J. Chem. Eng. Data 2021, 66, 1249−1254

Figure 4. Synthetic route of L-p -toluenesulfonate ethyl lactate.

Article

Figure 3. XRD di ﬀ raction pattern of point E at 25 °C: (a) p -MePhSO K sample; (b) K CO sample; and (c) sample of saturation point E.

Figure 5. H NMR spectra of L-p-toluenesulfonate ethyl lactate.

The crystallization zone of AFE is larger than that of EDC.

The wet slag method is used to get the composition of

samples. Besides, X-ray diﬀraction method is used to verify E-

point equilibrium samples (Figure 2). As shown in Figure 3,

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J. Chem. Eng. Data 2021, 66, 1249−1254

Article

Figure 6. High-performance liquid chromatograms of L-p-toluenesulfonate ethyl lactate.

MePhSO K. The purity of p-MePhSO K was 97.4%, and its

3 3

recovery rate was 94.6%. Then, the solution with K CO was

concentrated and dried. The acquired solid K CO was 67.6 g.

The purity of K CO was 94.8%, and its recovery was 98.3%.

2 3

Based on 1000 g quizalofop-p-ethyl wastewater, the evapo-

ration process was calculated according to the phase diagram at

3.5. Synthesis of L-p-Toluenesulfonate Ethyl Lactate.

The synthetic route of L-p-toluenesulfonate ethyl lactate is

shown in Figure 4. The 2.10 g (10 mmol) recovered p-

5 °C. As shown in Figure 2, K CO is retained as an

2 3

invariable component in the solution, and p-MePhSO K is

MePhSO K was added to the 50 mL three-port bottle. After

precipitated from point G to point E by evaporation. From

Table 2, the liquid phase composition of point E is p-

MePhSO K 3.30%, K CO 32.34%, and H O 64.36%. The

that, 200 μL of dimethylformamide and 25 mL of toluene were

added. Then, 1 mL (14 mmol) of SOCl was added into the

mixture below 0 °C and 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 ﬁnished,

liquid phase composition of point G (quizalofop-p-ethyl

wastewater) is p-MePhSO K 12.24%, K CO 13.76%, and

H O 74.00%. The following equation can be obtained

according to the material balance of evaporation from point

G to point E

the excess SOCl and toluene were distilled oﬀ and recovered.

After that, 25 mL of toluene, 2.0 mL of triethylamine (11

mmol), and 2.0 mL of ethyl L-lactate (18 mmol) were added

into the residue. The mixture reacted at 60−70 °C under

stiring for 4 h. After the reaction was ﬁnished, the liquid was

ﬁltered and washed three times with distilled water. L-p-

Toluenesulfonate ethyl lactate was obtained by rotary

evaporation, and the yield was 94.6%. Furthermore, the

p‐MePhSO K: 122.4 = x + 0.033z

(1)

(2)

(3)

(4)

K CO : 137.6 = 0.3234z

H O: 740 − y = 0.6436z

structure of the target chemical was validated by H NMR,

x + y + z = 1000

which is shown in Figure 5. The 91.6% content of ethyl lactate

L-p-toluene sulfonate was determined by HPLC (shown in

Figure 6).

In the equation, x and y are the amounts of p-MePhSO K

precipitated and evaporated water from point G to point E,

respectively, and z is the amount of the residual solution.

According to the above equations, x, y, and z are 108.36,

4. CONCLUTIONS

66.16, and 425.48 g, respectively.

.4. Separation Scheme Application. 500 g quizalofop-

The solubility isotherms of the p-MePhSO K−K CO −H O

system at 15, 25, 35, 45, and 55 °C were determined. The

phase diagram of the system at 25 °C was plotted and analyzed

in this study. The solubility isotherms show that the solubility

p-ethyl wastewater was weighed and added into 12.1 g solid

KOH. Then, 219.5 g water was distilled out. The obtained

system was mechanically stirred to 25 °C and kept at the

temperature to equilibrate for 2 h. It can be seen from Figure 2,

K CO is retained in the solution and p-MePhSO K is

of p-MePhSO K decreases remarkably with the concentration

of K CO increasing. Moreover, evaporating crystallization is

chosen as a preferential way for the separation of p-MePhSO K

precipitated from point G to point E by evaporation. That is

from the system.

Based on the phase diagram of the p-MePhSO K CO −H O

equilibrium system at 25 °C, the system was evaporated and

to say, the only solid p-MePhSO K can be obtained during the

evaporation process. By drying, we can get the solid p-

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J. Chem. Eng. Data 2021, 66, 1249−1254

Journal of Chemical & Engineering Data

aryloxyphenoxypropionate herbicides in Phalaris minor populations in

Article

crystallized in stages. The recovery rate of p-MePhSO K is

Iran. Weed Biol. Manage. 2011, 11, 29−37.

4.6%, and the purity is 97.4%. The recovery rate of K CO is

2 3

(6) Wu, H.; Zhao, Y.; Tan, X.; Zeng, X.; Guo, Y.; Yang, J. A

8.3%, and the purity is 94.8%.

The recovered p-MePhSO K was transformed into the

convenient method for determination of quizalofop-p -ethyl based on

the fluorescence quenching of eosin Y in the presence of Pd(II).

Spectrochim. Acta Mol. Biomol. Spectrosc. 2017 , 174 , 301 −306.

intermediate p-toluene sulfonyl chloride and then into the

intermediate L-p-toluenesulfonate ethyl lactate for the

production of quizalofop-p-ethyl. The yield and purity of the

product are 94.6 and 91.6%, respectively.

(7) Tang, W.; Zhou, F.; Chen, J.; Zhou, X. Resistance to ACCase-

inhibiting herbicides in an asia minor bluegrass (Polypogon fugax)

population in China. Pestic. Biochem. Physiol. 2014 , 108 , 16 −20.

(8) Guan, W.; Zhang, H. Determination and study on residue and

AUTHOR INFORMATION

dissipation of benazolin-ethyl and quizalofop-p -ethyl in rape and soil.

Int. J. Environ. Anal. Chem. 2013, 93, 679−691.

■

Corresponding Author

(

9) Mantzos, N.; Karakitsou, A.; Nikolaki, S.; Leneti, E.;

Hao Shuanghong − Research Center of Agro-Bionic

Engineering & Technology of Shandong Province, College of

Chemistry & Pharmacy, Qingdao Agricultural University,

Qingdao 266109, China; orcid.org/0000-0002-9458-

Konstantinou, I. Dissipation and transport of quizalofop-p -ethyl

herbicide in sunflower cultivation under field conditions. Environ. Sci.

Pollut. Res. Int. 2016, 23, 3481−3490.

(10) Wang, J. Y.; Ni, W.; Sun, X. F.; Li, J. Q.; Wang, B.; Dan, Y. X.;

Yan, P.; Yan, F. S. Preparation method of quizalofop-P-ethyl. CN

112; Email: doublered74@sina.com

106432109 A, 2017.

Authors

(11) Yang, X. Z.; Wei, N. C.; Liu, Q. M.; Dai, R. H.; Wang, Z.;

Zhang, Y. L.; Zhang, J. L.; Liu, Y. X.; Li, L.; Hu, Q. L. A kind of

preparation method of Quizalotop-ethyl. CN 102584724 B, 2016.

Xu Jie − Research Center of Agro-Bionic Engineering &

Technology of Shandong Province, College of Chemistry &

Pharmacy, Qingdao Agricultural University, Qingdao

(

12) Korea Research Institute of Chemical Technology. Process for

preparing (R)-aryloxypropionic acid ester derivatives. WO

004002925 A2, 2004.

13) Tadashi, K.; Tetsuo, I.; Tomofumi, S.; Atsuko, T. Preparation

of sulfonamides from sodium sulfonates: Ph P ·Br and Ph P ·Cl as a

66109, China; orcid.org/0000-0002-0234-6342

mild halogenating reagent for sulfonyl bromides and sulfonyl

Chen Mengqi − Research Center of Agro-Bionic Engineering &

Technology of Shandong Province, College of Chemistry &

Pharmacy, Qingdao Agricultural University, Qingdao

chlorides. Synthesis 1998 , 1998 , 423 −426.

66109, China

Wei Yan − Research Center of Agro-Bionic Engineering &

Technology of Shandong Province, College of Chemistry &

Pharmacy, Qingdao Agricultural University, Qingdao

(14) Shinsaku, F. A convenient preparation of arenesulfonyl

chlorides from the sodium sulfonates and phosphoryl chloride/

sulfolane. Synthesis 1982 , 5 , 423 −424.

(15) Grzegorz, B. A new, mild preparation of sulfonyl chlorides.

66109, China

Tetrahedron Lett. 2003, 7, 1499−1501.

Complete contact information is available at:

https://pubs.acs.org/10.1021/acs.jced.0c00837

(16) Zhao, W.; Zou, W.; Liu, T.; Zhang, F.-B.; Zhang, G.-L.; Xia, Q.

Solubilities of p-Toluenesulfonic acid monohydrate and sodium p-

toluenesulfonate in aqueous sulfuric acid solutions and its application

for preparing sodium p-toluenesulfonate. Ind. Eng. Chem. Res. 2013,

52, 18466−18471.

Author Contributions

X.J. and C.M. have contributed equally.

†

(17) Du, C.; Zheng, S.; Li, H.; Zhang, Y. Solid-liquid equilibria of

Notes

K CO + K CrO + H O system. J. Chem. Eng. Data 2006, 51, 104−

The authors declare no competing ﬁnancial interest.

106.

18) Chen, M.-Q.; Xu, J.; Wei, Y.; Hao, S. H. Recovery of PhSO K

ACKNOWLEDGMENTS

from industrial waste based on solid-liquid equilibrium of the

■

PhSO K-K CO -H O system. J. Chem. Eng. Data 2018, 63, 1397−

This work is supported by the National Undergraduate

Training Program for Innovation (no. 201510435015), the

National Natural Science Foundation of China (no.

1706142), the National Natural Science Foundation of

China (no. 31471808), and the Research Foundation for

Distinguished Scholars of Qingdao Agricultural University

(

402.

19) Nouri, K.; Jemmali, M.; Walha, S.; Ben Salah, A.; Dhahri, E.;

Bessais, L. Experimental investigation of the Y-Fe-Ga ternary phase

diagram: Phase equilibria and new isothermal section at 800 °C. J.

Alloys Compd. 2017, 719, 256−263.

(20) Smith, K. B.; Bridson, R. H.; Leeke, G. A. Solubilities of

pharmaceutical compounds in ionic liquids. J. Chem. Eng. Data 2011,

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663-1116020).

21) Shen, S.; Feng, X.; Zhao, R.; Ghosh, U. K.; Chen, A. Kinetic

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