Equilibrium Solubility of Sodium 1-Naphthalenesulfonate in Binary

Institute of Applied Chemistry, TaiZhou University, Linhai, Zhejiang 317000, ... Institute of Industrial Catalysis, Zhejiang University of Technology,...
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Equilibrium Solubility of Sodium 1‑Naphthalenesulfonate in Binary NaCl + Water, Na2SO4 + Water, and C2H5OH + Water Solvent Mixtures from (278.15 to 323.15) K Rongrong Li,*,†,‡ Jian Wan,† Yingjie Zhang,† Danxia Liang,† Bin Zhang,† and Chenghong Li*,† †

Institute of Applied Chemistry, TaiZhou University, Linhai, Zhejiang 317000, P. R. China. Institute of Industrial Catalysis, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, P. R. China.

‡

ABSTRACT: The equilibrium solubility of sodium 1-naphthalenesulfonate in binary NaCl + water, Na2SO4 + water, and C2H5OH + water solvent mixtures was measured by a steady-state method at elevated temperatures from (278.15 to 323.15) K. The results of these data were correlated by a modified Apelblat equation. The dissolution enthalpy (ΔHd) and entropy (ΔSd) of sodium 1-naphthalenesulfonate in solutions of different mole fraction were obtained.

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K.10−14 The experimental data were correlated by a modified Apelblat equation.

INTRODUCTION

Sodium 1-naphthalenesulfonate (CAS Registry Nomber: 13014-3, molecular formula: C10H7NaO3S) is a valuable regent that is used in the functionalized reduced graphene oxide stabilization of silver nanoparticles 1 as an intermediate in the manufacturing of 8-anilino-sodium 1-naphthalenesulfonate and 8-p-toluidino-sodium 1-naphthalenesulfonate, and for many other applications.2−4 It is mainly gained from the sulfonation of naphthalene with concentrated sulfuric acid, and then condensation by NaCl. These products formed by this method include sodium 1- and 2-naphthalenesulfonates in different proportions, which were respectively gained via condensation and sulfonation. It is very important to purify sodium 1naphthalenesulfonate via crystallization. Some studies used the method of ion exchange process to separate sodium 1naphthalenesulfonate from the β-salt mother liquor.5,6 It is indispensable to refine the sodium 1-naphthalenesulfonate in the entire process. However, it is not easy to gain the highpurity sodium 1-naphthalenesulfonate from the products. The sodium 1-naphthalenesulfonate is gained by means of crystallization in NaCl, Na2SO4, or C2H5OH aqueous solution. The results of solubility data of sodium 1-naphthalenesulfonate in binary NaCl + water, Na2SO4 + water, and C2H5OH + water solvent mixtures is enormous significance to the crystallization process. But so far, there has been no literature reporting on the solubility of sodium 1-naphthalenesulfonate.7−9 So this work focuses on a systematic measurement of the solubility of sodium 1-naphthalenesulfonate in binary NaCl + water, Na2SO4 + water, and C2H5OH + water solvent mixtures was determined by steady-state method from (278.15 to 323.15) © XXXX American Chemical Society

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EXPERIMENTAL SECTION Chemicals. Sodium 1-naphthalenesulfonate had a purity of 0.995 (mass fraction), which was purchased by Aladdin Chemical Co. Ltd. (China) and was used without any other purification. The purity of sodium 1-naphthalenesulfonate was determined using HPLC and was analyzed to be more than 0.995. Na2SO4 and NaCl, which have purities of 0.998 and 0.996 (mass fraction), respectively, were purchased by Shenyang Chemical Reagent Co. C2H5OH with a purity of 0.995 (mass fraction) was supplied by Shanghai Chemical Reagent Co. The twice distilled water used in our work had conductivity less than 5 μS·cm−1. Apparatus and Procedures. To begin with, 50 mL of water, which was placed into a 125 mL Erlenmeyer flask, was transferred into a water bath with constant temperature (Neslab, RTE-101, uncertainty of ± 0.01 K), then recirculated via a copper coil. A condenser was used with the flask in order to prevent the solutions evaporated while using Teflon-coated magnetic stirring bar to stir the solutions. The equilibrated solutions remained for at least 3 days in the set temperature. Then the HPLC was used to determine the solute, which taken at a 2 h intervals. It indicated that equilibration could be reached when the composition of the liquid phase became constant. Equilibrium will be reached after 11 h generally. Any Received: June 8, 2014 Accepted: December 24, 2014

A

DOI: 10.1021/je500517d J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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Table 1. Mole Fraction Solubility x of Sodium 1-Naphthalenesulfonate in (1 − w) Water + w Na2SO4 between (278.15 and 323.15) K under Pressure of 0.1 MPaa T

a

w=0

w = 0.05

w = 0.10

w = 0.15

w = 0.20

K

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

1.0707 1.0876 1.1296 1.1852 1.2558 1.3358 1.4130 1.5162 1.6876 1.9223

−0.89 −0.63 0.41 1.12 1.56 1.24 −0.74 −2.31 −1.13 1.45

0.8628 0.8852 0.9376 0.9919 1.0480 1.1416 1.2258 1.3344 1.4691 1.6544

−0.12 −0.82 0.52 0.69 −0.25 0.94 −0.14 −0.67 −0.79 0.66

0.6101 0.6344 0.6812 0.7318 0.7842 0.8665 0.9526 1.0799 1.2090 1.3531

0.46 −0.57 0.43 0.37 −0.94 −0.13 −0.72 0.93 0.59 −0.50

0.3462 0.3706 0.3968 0.4286 0.4735 0.5390 0.5951 0.6943 0.8010 0.9694

−1.78 0.51 0.89 0.34 0.37 1.81 −1.24 −0.14 −1.45 0.87

0.0457 0.0465 0.0534 0.0620 0.0736 0.0932 0.1233 0.1629 0.2392 0.3670

−4.62 −4.10 2.42 4.12 2.76 2.60 2.18 −2.81 −1.34 0.62

RD = (xi − xcalc i )/xi; w, mass fraction of Na2SO4 in water. Standard uncertainties u are ur(w) = 0.02, u(T) = 0.05 K, ur(x) = 0.02, u(P) = 2 kPa.

Table 2. Mole Fraction Solubility x of Sodium 1-Naphthalenesulfonate in (1 − w) Water + w NaCl between (278.15 and 323.15) K under Pressure of 0.1 MPaa T

a

w = 0.05

w = 0.10

w = 0.15

w = 0.20

K

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

0.8921 0.9145 0.9644 1.0094 1.0742 1.1429 1.2040 1.3063 1.4411 1.6182

−0.85 −0.79 0.94 0.83 1.38 0.96 −1.32 −1.48 −0.72 1.10

0.7064 0.7269 0.7632 0.8031 0.8540 0.9162 0.9917 1.1205 1.2544 1.4237

−1.03 −0.13 1.12 1.05 0.59 −0.33 −1.63 0.21 0.04 0.22

0.3418 0.3656 0.3998 0.4411 0.4845 0.5777 0.6745 0.7713 0.8832 1.0967

0.31 −0.04 0.13 −0.40 −2.88 1.55 2.55 0.35 −2.90 1.01

0.0390 0.0445 0.0511 0.0622 0.0753 0.0949 0.1180 0.1560 0.2291 0.3215

−6.57 −0.84 0.93 4.32 3.48 3.08 −1.96 −4.06 1.60 −0.04

RD = (xi − xcalc i )/xi; w, mass fraction of NaCl in water. Standard uncertainties u are ur(w) = 0.02, u(T) = 0.05 K, ur(x) = 0.02, u(P) = 2 kPa.

Table 3. Mole Fraction Solubility x of Sodium 1-Naphthalenesulfonate in (1 − w) Water + w C2H5OH between (278.15 and 318.15) K under Pressure of 0.1 MPaa T

a

w = 0.08

w = 0.17

w = 0.35

w = 0.54

w = 0.70

K

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

102 xi

103 RD

278.15 283.15 288.15 293.15 298.15 303.15 308.15 313.15 318.15 323.15

0.1965 0.2191 0.2555 0.3134 0.3832 0.4755 0.6043 0.7624 0.9285 1.1250

9.87 1.58 −3.11 −2.94 −3.39 −2.52 0.52 2.63 1.09 −1.11

0.1444 0.1601 0.1916 0.2348 0.2898 0.3665 0.4706 0.5856 0.7153 0.9108

8.08 −0.55 −2.58 −2.77 −2.77 −0.81 2.19 1.66 −1.09 −0.01

0.1051 0.1199 0.1395 0.1769 0.2191 0.2623 0.3567 0.4559 0.5630 0.7212

7.48 1.58 −3.48 −0.74 −1.12 −5.77 1.95 2.75 −0.39 −0.40

0.0776 0.0894 0.1091 0.1346 0.1601 0.2063 0.2692 0.3547 0.4559 0.5905

4.65 0.60 0.74 0.70 −4.33 −2.36 −0.20 1.92 0.71 −0.58

0.0442 0.0511 0.0629 0.0835 0.1002 0.1356 0.1700 0.2181 0.3036 0.3989

1.89 −2.70 −2.67 3.43 −2.01 3.18 −0.42 −2.90 1.76 −0.31

RD = (xi − xcalc i )/xi; w, mass fraction of C2H5OH in water. Standard uncertainties u are ur(w) = 0.02, u(T) = 0.05 K, ur(x) = 0.02, u(P) = 2 kPa.

solid phase would be settled after stirring was stopped. Try to get the saturated liquid without including solid phase when it’s ten minutes prior to sampling. Then, the liquid phase of approximately 1−2 cm3 was taken out from the clear solution with preheated glass syringes and determined by HPLC. Repetitive measurements was used to verify the obtained equilibrium after 3 or more days, and it also can be verified by approaching equilibrium from supersaturation, which preequilibrated the solutions at a higher temperature. The liquid phase was taken out when equilibrium was reached. An electronic balance was used to measure the sample, which was measured

using HPLC quantitatively afterward. Schreinemaker’s wet residue method was used to determine the substance of the wet residue. The wet solid phase was moved into a beaker as well as some saturated liquid phase. Then, stir the liquid until the wet residue dissolved and analyze using HPLC. This procedure was repeated at a high concentration of the salts to confirm whether there is sodium sulfate or sodium chloride obtained. Interlinking of the liquid phase and wet residue points then extended. There is only sodium 1-naphthalenesulfonate obtained in the phase diagrams (sodium sulfate or sodium chloride + sodium 1-naphthalenesulfonate + water). B

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Figure 1. (a) Equilibrium solubility x of sodium 1-naphthalenesulfonate in aqueous solutions of Na2SO4 at different temperatures. (b) Logarithmic relationship between the solubility and the inverse of temperature: ■, w = 0 Na2SO4; ▲, w = 0.05 Na2SO4; ▼, w = 0.10 Na2SO4; ⧫, w = 0.15 Na2SO4; ●, w = 0.20 Na2SO4; , calculated values.

Figure 2. (a) Equilibrium solubility x of sodium 1-naphthalenesulfonate in aqueous solutions of NaCl at different temperatures. (b) Logarithmic relationship between the solubility and the inverse of temperature: ■, w = 0.05 NaCl; ▲, w = 0.10 NaCl; ▼, w = 0.15 NaCl; ⧫, w = 0.20 NaCl; , calculated values.

Figure 3. (a) Equilibrium solubility x of sodium 1-naphthalenesulfonate in aqueous solutions of C2H5OH at different temperatures. (b) Logarithmic relationship between the solubility and the inverse of temperature: ■, w = 0.08 C2H5OH; ▲, w = 0.17 C2H5OH; ▼, w = 0.35 C2H5OH; ⧫, w = 0.54 C2H5OH; ●, w = 0.70 C2H5OH; , calculated values.

data.16,17 The calculation of the mole fraction solubility (x) was used as follows:

Analysis. The analysis method was the same in previous works. 15 The mass fraction of sodium 1-naphthalenesulfonate in solutions was determined by a Shimadzu-6A High performance liquid chromatography. A unimicro Kromasil C18, 5 μm (250 mm × 4.6 mm) was used as the HPLC Column, and was kept at 308.2 K. Shimadzu SPD-6A UV single spectrophotometric detector was used as detector and was set at the wavelength of 199 nm. The average data of the three measurement points was used as the final experimental

x=

m1/M1 m1/M1 + m2 /M 2 + m3 /M3

(1)

where m1 represents the mass of sodium 1-naphthalenesulfonate, m2 represents the mass of NaCl, Na2SO4 or C2H5OH, and m3 represents the mass of H2O. M1, M2, and M3 represent the molecular weight of the sodium 1-naphthalenesulfonate and C

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different solvent, respectively. The solute with the subscript of 1 is sodium 1-naphthalenesulfonate, solvent 2 represents NaCl, Na2SO4, or C2H5OH, and the solvent 3 represents water. The symbol of u is the standard uncertainties, which are ur(w) = 0.02, u(T) = 0.05 K, ur(x) = 0.02, u(P) = 2 kPa.

Table 4. Parameters of Equation 2 for Sodium 1Naphthalenesulfonate in Aqueous Solutions of Different Mole Fractions

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solvent sodium sulfate

RESULTS AND DISCUSSION The equilibrium solubility data of sodium 1-naphthalenesulfonate in binary NaCl + water, Na2SO4 + water, and C2H5OH + water solvent are presented in Tables 1−3, separately. Figures 1−3 account for the corresponding equilibrium solubility curves, respectively. Because the polarity of sodium 1naphthalenesulfonate is approach to the solvent, the solubility of sodium 1-naphthalenesulfonate in NaCl + water, Na2SO4 + water, or C2H5OH + water solvent mixtures is lower than that in pure water. Figures 1−3 illustrate that the equilibrium solubility of sodium 1-naphthalenesulfonate in C2H5OH + water solvent mixtures or NaCl mixture is less than that in Na2SO4 + water at the same states. Sodium sulfate + water solvent mixture may be the optimizing choice for purifying sodium 1-naphthalenesulfonate. The relationship between equilibrium solubility data of sodium 1-naphthalenesulfonate and temperature was correlated by modified Apelblat equation.18−21 The semiempirical equation was used as follows: ln(x) = A +

sodium chloride

ethanol

= = = = = =

0 0.05 0.10 0.15 0.20 0.05

−325.43 −273.38 −294.75 −457.40 −1371.70 −273.66

1.34 1.09 1.15 1.85 5.75 1.10

48.46 40.75 44.06 68.45 205.61 40.73

1.86 0.76 0.58 0.64 0.26 1.28

w w w w w w w w

= = = = = = = =

0.10 0.15 0.20 0.08 0.17 0.35 0.54 0.70

−378.50 −423.31 −1015.43 −211.32 −280.04 −337.45 −445.26 −502.70

1.55 1.67 4.16 0.60 0.90 1.14 1.60 1.83

56.45 63.53 152.47 32.45 42.73 51.33 67.45 76.09

0.71 1.17 0.30 0.59 0.35 0.35 0.19 0.16

ΔHd ΔSd + (5) RT R The dissolution of sodium 1-naphthalenesulfonate of Gibbs free energy in different temperatures and solvents could be gained by the Gibbs free energy equation, which shows as in the following equation:24,25

(2)

ΔGd = ΔHd − T ΔSd

i=1

Table 5. Dissolution Enthalpy and Entropy of Sodium 1Naphthalenesulfonate in Aqueous Solutions of Different Mole Fractionsa ΔHd × 10−3

⎤

J·mol

2⎥

− xi)

⎥⎦

sodium sulfate

(3)

The N represents the count of experimental data. xicalc (calculated solubility) and xi mean the equilibrium solubility calculated in eq 2 and the measurement data of the equilibrium solubility, respectively. xcalc meets good with the measurement i data (xi) in Figure 1−3. Bennema et al. 22 discussed the relevance between the solid solute saturated mole fraction equilibrium solubility in the absolute temperature and an ideal solution. The van’t Hoff equation was used to correlate the natural logarithm of saturated mole fraction equilibrium solubility and the inverse of absolute temperature, which was listed as follows: ln x = −

ΔHfus ΔSfus + RT R

(6)

The dissolution entropy and enthalpy was calculated by the least-squares method. The ΔGd determined by the data of ΔSd and ΔHd at 278.15 K are represented in Table 5, respectively. The negative value of dissolution enthalpy, ΔHd in Table 5 is may caused by the ion interaction between the sodium 1-

solvent

∑

RMSD × 10−4

w w w w w w

1/2

(xicalc

C

The nonideal soluble behavior in the real liquid phase was considered by Song et al.23 They displaced ΔHfus by enthalpy of dissolution ΔHd and took the place of ΔSfus instead of the entropy of dissolution ΔSd, which was listed as follows:

The A, B, and C stand for parameters, T was the Kelvin temperature, and x is the mole fraction of sodium 1naphthalenesulfonate in solutions of NaCl, Na2SO4, or C2H5OH. The parameter C means the influence of temperature on the fusion enthalpy stand for a deviation of ΔCp (heat capacity). The parameters A and B account for the influence of solution nonidealities on the equilibrium solubility of the solute and the activity coefficient of variation. The multidimensional unconstrained nonlinear minimization of constants A, B, and C was calculated by the software of MATLAB. The RD (relative deviations) between calculated and experimental data is also listed in Tables 1−3, respectively. Table 4 represented the RMSD (root-mean-square deviations) and the regressed values of A, B and C, which were determined as follows: N

B× 104

ln x = −

B + C ln(T /K ) (T / K )

⎡ 1 RMSD = ⎢ ⎢⎣ N − 1

A

sodium chloride

ethanol

w w w w w w w w w w w w w w

= = = = = = = = = = = = = =

0 0.05 0.10 0.15 0.20 0.05 0.10 0.15 0.20 0.08 0.17 0.35 0.54 0.70

−1

0.72 3.44 5.56 4.49 −2.81 2.33 1.40 7.95 6.88 25.12 24.39 24.21 22.60 23.38

ΔGd × 10−3

ΔSd −1

−1

J·mol ·K −35.07 −27.15 −22.46 −30.80 −73.67 −30.80 −36.06 −18.65 −39.99 31.34 26.44 17.75 15.14 13.51

J·mol−1 10.47 10.99 11.80 13.06 17.68 10.89 11.43 13.14 18.00 16.37 17.03 23.22 18.39 19.62

The values of ΔGd were calculated by the values of ΔHd and ΔSd at 278.15 K. a

(4) D

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(11) Ferreira, O.; Schröder, B.; Pinho, S. P. Solubility of hesperetin in mixed solvents. J. Chem. Eng. Data 2013, 58, 2616−2621. (12) Ricardo, P.; Moilton, F. Solubility of benzoic acid in aqueous solutions containing ethanol or N-propanol. J. Chem. Eng. Data 2008, 53, 2704−2706. (13) Krüger, A. J.; Krieg, H. M.; Neomagus, H. W. J. P. SO2 Solubility in 50 wt % H2SO4 at elevated temperatures and pressures. J. Chem. Eng. Data 2014, 59, 1−7. (14) Surendra, K.; Siddh, N. U.; Virendra, K. M. On the solubility of benzoic acid in aqueous carboxymethylcellulose solutions. J. Chem. Eng. Data 1978, 23, 139−141. (15) Li, R. R.; Lin, J.; Ying, A. G.; You, Y. J.; Li, C. H. Solubility of sodium 4-nitrobenzenesulfonate in binary sodium chloride + water, sodium sulfate + water, and ethanol + water solvent mixtures at elevated temperatures. J. Chem. Eng. Data 2012, 57, 427−430. (16) Shaw, C. J.; Barton, D. L. A direct HPLC method for the resolution of glycidyl tosylate and glycidyl 3-nitrobenzenesulphonate enantiomers. J. Pharm. Bioamed. Anal. 1991, 9, 793−796. (17) Schmidt, T. C.; Buetehorn, U.; Steinbach, K. HPLC-MS investigations of acidic contaminants in ammunition wastes using volatile ion-pairing reagents (VIP-LC-MS). Anal. Bioanal. Chem. 2004, 378, 926−931. (18) Li, D. Q.; Evans, D. G.; Duan, X. Solid-liquid equilibria of terephthalaldehydic acid in different solvents. J. Chem. Eng. Data 2002, 47, 1220−1221. (19) Venkatesu, P.; Sekhar, G. C.; Rao, M. V. P.; Hofman, T.; Domanska, U. Solid−Liquid Equilibria of n-Alkanes in N,NDimethylformamide. J. Chem. Eng. Data 2000, 45, 177−181. (20) Apelblat, A.; Manzurola, E. Solubilities of o-acetylsalicylic, 4aminosalic, 3,5-dinitrosalicylic, and p-toluic acid, and magnesium-DLaspartate in water from T = (278 to 348) K. J. Chem. Thermodyn. 1999, 31, 85−91. (21) Zhao, H. K.; Li, R. R.; Ji, H. Z.; Zhang, D. S.; Tang, C.; Yang, L. Q. Equilibrium solubility of 3- and 4-nitrophthalic acids in water. J. Chem. Eng. Data 2007, 52, 2072−2073. (22) Bennema, P.; van Eupen, J.; van der Wolf, B. M. A.; Los, J. H.; Meekes, H. Solubility of molecular crystals: Polymorphism in the light of solubility theory. Int. J. Pharm. 2008, 351, 74−91. (23) Song, L. C.; Gao, Y.; Gong, J. B. Measurement and Correlation of Solubility of Clopidogrel Hydrogen Sulfate (Metastable Form) in Lower Alcohols. J. Chem. Eng. Data 2011, 56, 2553−2556. (24) Garcia-Delgado, R. A.; Cotoruelo-Mingueza, L. M.; Rodriguez, J. J. Equilibrium Study of Single-Solute Adsorption of Anionic Surfactants with Polymeric XAD Resins. Sep. Sci. Technol. 1992, 27, 975−987. (25) Ayranci, E.; Duman, O. Apparent Molar Volumes and Isentropic Compressibilities of Benzene Sulfonates and Naphthalene Sulfonates in Aqueous Solutions at (293.15, 303.15, 313.15, 323.15, and 333.15) K. J. Chem. Eng. Data 2010, 55, 947−952.

naphthalenesulfonate and the high concentration of sodium sulfate. We can concluded from Tables 1−3 and Figures 1−3: first, the equilibrium solubility of sodium 1-naphthalenesulfonate increases with temperature in mixtures solvent of NaCl + water, Na2SO4 + water, or C2H5OH + water solvent. Second, the influence of NaCl, Na2SO4, or C2H5OH on the equilibrium solubility of sodium 1-naphthalenesulfonate may be on account of the salting-out effect. Third, the experiment data was regressed well by using the eq 2 for each series. The correlation equation and equilibrium solubility data gained by this paper is advantageous in the process of separation of sodium 1- or 2naphthalenesulfonate and dealing with purification of sodium 1naphthalenesulfonate in industry.

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AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected] (L. Rongrong). Tel.: +86 576 8548 6698. Fax: +86 576 8513 7169. *E-mail: [email protected] (L. Chenghong). Tel.: +86 576 8548 6698. Fax: +86 576 8513 7169. Funding

The project was supported by the Key Disciplines of Applied Chemistry of Zhejiang Province Taizhou University, and the School Project of Taizhou University (2014PY031, 2014QN013 and 14XS26). Notes

The authors declare no competing financial interest.

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REFERENCES

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DOI: 10.1021/je500517d J. Chem. Eng. Data XXXX, XXX, XXX−XXX