Article Cite This: Ind. Eng. Chem. Res. 2018, 57, 11826−11832
pubs.acs.org/IECR
Optimal Design of Neutralization Process in 1,5Dihydroxynaphthalene Production with Solubility Difference of Naphthalene-1,5-disulfonic Acid and Naphthalene-1,5-disulfonic Acid Disodium in Aqueous Sulfuric Acid Solutions Yong-Sheng Xu, Rui-Xiong Zhao, Kang-Kang Pei, Guo-Liang Zhang, Qing Xia,* and Feng-Bao Zhang*
Downloaded via KAOHSIUNG MEDICAL UNIV on August 29, 2018 at 14:12:08 (UTC). See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.
School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China S Supporting Information *
ABSTRACT: An optimal design of the neutralization process in 1,5-dihydroxynaphthalene production was proposed and discussed. In the new strategy, instead of sodium chloride, sodium sulfate was used in the salting-out process to overcome the drawbacks of the traditional strategy. Then the precipitated mixtures, mainly naphthalene-1,5-disulfonic acid (1,5-H2NDS) and sodium sulfate, were neutralized to obtain naphthalene-1,5-disulfonic acid disodium (1,5Na2NDS) and sulfuric acid. By adjusting the concentrations of sulfuric acid solutions to 0.3 and 0.5 mass fractions, 1,5Na2NDS and 1,5-H2NDS were precipitated out, respectively. The yields of both 1,5-H2NDS and 1,5-Na2NDS reached 0.98. 1,5-Na2NDS was sent to the alkali fusion process, while 1,5H2NDS was reused in the neutralization. In neutralization, the mole ratio (1,5-H2NDS to sodium sulfate) was chosen as 2.5 and the reaction temperature was 353 K. In order to determine the separation conditions, the solubilities of 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O in aqueous sulfuric acid solutions were measured over the temperature range from 277 to 337 K at atmospheric pressure by a dynamic method. The new strategy is particularly instructive for the industrial production of 1,5dihydroxynaphthalene.
1. INTRODUCTION
corrosion of the equipment and creates a hazardous working condition for workers. What is more, the mass fraction of sodium chloride entraining in the product of the salting-out process reaches about 0.08−0.15.12 Because of the high melting point of sodium chloride, the entrainment of sodium chloride leads to the high alkali fusion temperature. Besides, the viscosity of alkali fusion reactants also increases with the content of sodium chloride, which is unfavorable for the alkali fusion reaction. All the previously mentioned limitations increase energy consumption and also do harm to the equipment. Furthermore, as the reactant in alkali fusion, 1,5-H2NDS is neutralized to naphthalene-1,5-disulfonic acid disodium (C10H6Na2O6S2, 1,5-Na2NDS, CAS No. 1655-29-4) first, and then conveyed to sodium phenolate in the alkali fusion reaction. Compared with the condition that 1,5-Na2NDS is used as the reactant of alkali fusion directly, 1,5-H2NDS consumes more sodium hydroxide. Meanwhile, water
1,5-Dihydroxynaphthalene (C10H8O2, 1,5-DHN, CAS No. 8356-7), an important intermediate product in chemical industry, can be applied in organic synthesis,1,2 dyestuffs,3,4 medicine,5,6 the photographic industry,7 and other fields.8,9 With the development of it is downstream products in recent years, 1,5DHN has a better market in China.10,11 The traditional industrial strategy of producing 1,5-DHN includes four steps, which are sulfonation, salting-out, alkali fusion, and acidification.12 As shown in Figure 1, first, naphthalene is sulfonated to prepare the intermediate product naphthalene-1,5-disulfonic acid (C10H8O6S2, 1,5-H2NDS, CAS No. 81-04-9). Then, in the salting-out process, 1,5-H2NDS is separated out by introducing a certain amount of saturated sodium chloride solution. Afterward, 1,5-H2NDS reacts with sodium hydroxide around 598 K in the alkali fusion process. Finally, the alkali fusion product is acidified and 1,5-DHN is obtained from the mother liquor. However, the traditional strategy suffers from several major drawbacks. First of all, the traditional salting-out process involves the use of sodium chloride. Volatile hydrogen chloride gas is generated when saturated sodium chloride solution is introduced to concentrated sulfuric acid solution, which causes © 2018 American Chemical Society
Received: Revised: Accepted: Published: 11826
May 16, 2018 July 3, 2018 July 31, 2018 July 31, 2018 DOI: 10.1021/acs.iecr.8b02165 Ind. Eng. Chem. Res. 2018, 57, 11826−11832
Article
Industrial & Engineering Chemistry Research
Figure 1. Traditional industrial strategy of producing 1,5-DHN.
molar ratio of 1,5-H2NDS to sodium sulfate ranged from 1.0 to 5.0. The solution was controlled at 323−353 K with continuous stirring until all materials were dissolved. After the dissolution, a certain amount of concentrated sulfuric acid was added dropwise to the solution with continuous stirring. Then the solution was cooled to room temperature and the precipitated solid crystal was separated by filtration and analyzed by proton nuclear magnetic resonance (1H NMR) spectroscopy. The result is shown in Figure S9 (Supporting Information), and no peak of hydrogen in the sulfonic acid group can be found, which proves that the product is 1,5Na2NDS. The yield of 1,5-Na2NDS is defined by the mass ratio of obtained 1,5-Na2NDS to theoretical 1,5-Na2NDS which is calculated by stoichiometry. The residual filtrate was put into a four-neck round-bottom flask and the temperature was kept at 383 K to evaporate water until the mass fraction of sulfuric acid in filtrate reached 0.50. After the solution was cooled to room temperature, the precipitated solid, mainly 1,5-H2NDS, was filtrated. The filtrate, mainly sulfuric acid solution, was reused. 2.3. Apparatus and Procedure of Solubility Measurement. The solubilities of 1,5-H2NDS·2H2O and 1,5-Na2NDS· H2O in aqueous sulfuric acid were measured by the dynamic method13−15 and combined with the laser monitoring observation technique to observe the dissolving process. The apparatus and procedure of the solubility experiments were described as follows.16−18 Prepared solvent and solute were weighed using an electronic analytical balance (Gibertini, Crystal 200, Italy, accuracy of ±0.0001 g), and then transferred into a jacketed glass vessel connected to a cold-water condenser tube to prevent evaporation of the solvent. The mixtures were stirred continuously with a magnetic stir bar and heated slowly at a rate less than 0.2 K·h−1. The temperature of the solution, which was controlled by a refrigerated/heating circulator (Julabo FP45-HE, Germany, temperature stability ±0.01 K), was measured by a platinum resistance thermometer (PT-100, calibrated with an accuracy of 0.01 K). The temperature at which the intensity of the laser beam reached a maximum reading and remained steady, indicating all crystal was dissolved, was determined as the solid−liquid equilibrium (SLE) temperature.
produced in neutralization is undesirable for the alkali fusion reaction. Therefore, in consideration of the shortcomings in the traditional strategy above, a new strategy is put forward in this work. The feasibility of the improved strategy depends on the solubility difference of 1,5-Na2NDS and 1,5-H2NDS in aqueous sulfuric acid solution. However, no relative solubility data can be found in published references and databases. Therefore, in this work, the solubilities of 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O in aqueous sulfuric acid solutions were measured by a dynamic method over the temperature range from 277 to 337 K and the solute-free mass fraction of sulfuric acid range from 0.20 to 0.60 at atmospheric pressure. The modified Apelblat equation was used to correlate the experimental data. The optimization of the proposed new strategy was carried out according to the determined data.
2. EXPERIMENTAL SECTION 2.1. Material Preparation. The relevant information on the materials used in the experiments is listed in Table 1. The Table 1. Source and Mass Fraction Purity of the Materials Used in the Experiment materials
mass fraction purity
1,5-H2NDS
0.98
1,5-Na2NDS
0.98
concentrated sulfuric acid sodium sulfate
0.977
deionized water
0.99
source Heowns Biochemical Technology Co., Ltd., Tianjin, China Heowns Biochemical Technology Co., Ltd., Tianjin, China Yuanli Chemical Reagents Co. Ltd.,Tianjin, China Aladdin Biochemical Technology Co., Ltd., Shanghai, China Nankai Chemical Reagents Co., Tianjin, China
purchased 1,5-H2NDS and 1,5-Na2NDS were recrystallized three times from deionized water and then dried in a vacuum oven to constant weight at 333.15 K before measurement. High performance liquid chromatography (HPLC, Hitachi L7100, Japan) was used to analyze the purity of 1,5-H2NDS and 1,5-Na2NDS. The results are presented in Figure S1 and S2 (Supporting Information). 1,5-H2NDS and 1,5-Na2NDS crystals were analyzed by X-ray diffraction (XRD; D8-Focus, Germany) and thermogravimetric analysis (TGA; Mettler Toledo TGA/DSC 1, Switzerland) before and after dissolution to ensure that the crystals remained unchanged in the dissolution process. Figures S3 and S4 (Supporting Information) show the XRD patterns of 1,5-H2NDS and 1,5-Na2NDS, respectively, and the results of TGA are shown in Figures S5− S8 (Supporting Information). 2.2. Apparatus and Procedure of the New Strategy. Certain amounts of 1,5-H2NDS, sodium sulfate, and deionized water were added into a 500 mL four-neck round-bottom flask equipped with a mechanical stirrer, constant pressure feeder, thermometer, water condenser, and thermostatic oil bath. The
3. RESULTS AND DISCUSSION 3.1. Solubility Data and Correlation. The molality solubility data of 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O in aqueous sulfuric acid solutions are presented in Tables S1 and S2 (Supporting Information), where Texp is the measured absolute temperature, m1 and m2 are molality solubilities of 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O in aqueous sulfuric acid solutions, respectively, and w03 is the solute-free mass fraction of sulfuric acid in the solvent. In aqueous sulfuric acid solutions, ionic interaction among various species becomes comparatively complicated. This is because sulfuric acid has first and second thermodynamic dissociations, which makes the results correlated by electrolyte 11827
DOI: 10.1021/acs.iecr.8b02165 Ind. Eng. Chem. Res. 2018, 57, 11826−11832
Article
Industrial & Engineering Chemistry Research
Table 2. Parameters of the Apelblat Equation and Root-Mean-Square Deviations for 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O in Aqueous Sulfuric Acid Solutions solute
solvent
1,5-H2NDS·2H2O
1,5-Na2NDS·H2O
w03 w03 w03 w03 w03 w03 w03 w03 w03 w03
= = = = = = = = = =
0.20 0.30 0.40 0.50 0.60 0.20 0.30 0.40 0.50 0.60
A
B
C
σ (K)
−35.19 89.12 584.61 194.95 −405.48 129.45 52.59 −14.41 −182.73 −1223.76
717.44 −5731.16 −31268.4 −14745.1 14404.4 −7163.68 −3893.97 −1903.79 4356.48 4917.13
5.91 −12.25 −84.52 −26.41 61.54 −18.75 −7.27 3.17 28.75 184.35
0.61 0.50 1.09 1.10 1.27 0.55 0.51 0.87 0.92 1.49
thermodynamic models unsatisfactory. Since the modified Apelblat equation19,20 has been used as an semiempirical equation in many previously published studies of SLE data, such as in the sulfuric acid system,21,22 the experimental data in this work were correlated by the modified Apelblat equation. The modified Apelblat equation is shown as follows: ln m = A +
B + C ln(T ) T
(1)
where m is the molality solubility of the solute, T is the calculated absolute temperature, and A, B, and C are constants. The root-mean-square deviation σ between Texp and T is set as the objective function which is defined as ÄÅ N ÉÑ0.5 ÅÅ ÑÑ ÅÅ Ñ exp 2 σ = ÅÅ∑ (T − T ) /(N − 1)ÑÑÑ ÅÅ ÑÑ ÑÖ ÅÇ i = 1
(2)
where N is the number of experimental data points. A nonlinear minimization function in Matlab is used for minimizing σ and estimating parameters A, B, and C. The values of the model parameters and σ for determined systems are presented in Table 2. The root-mean-square deviations range from 0.50 to 1.49 K. 3.2. Discussion of Solubility Data. The solubility data of 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O in aqueous sulfuric acid solutions are shown in Figures 2 and 3. It is shown that the solubilities of both 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O increase with temperature and decrease with the mass fraction of sulfuric acid (w03). An obvious solubility difference between 1,5-H2NDS·2H2O and 1,5Na2NDS·H2O can be observed when 0.2 ≤ w03 ≤ 0.3, which suggests the concentration range for the precipitation of 1,5Na2NDS·H2O. When 0.4 ≤ w03 ≤ 0.6, the solubilities of both 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O decrease sharply compared with at 0.2 ≤ w03 ≤ 0.3, especially for 1,5-H2NDS· 2H2O. This feature can be attributed to the precipitation of 1,5-H2NDS·2H2O. 3.3. Design of the Neutralization Process in 1,5-DHN Production. The new strategy is illustrated in Figure 4. First, the sodium chloride is replaced by sodium sulfate to avoid the formation of the hydrogen chloride gas in the salting-out process. The solid mixture 1 obtained in the salting-out process is mainly sodium sulfate and 1,5-H2NDS. Second, a neutralization process is introduced between the salting-out process and the alkali fusion process. 1,5-H2NDS is neutralized by sodium sulfate in the solid mixture 1. The chemical equation of neutralization reaction is shown as eq 3.
Figure 2. Plot of molality solubilities of 1,5-H2NDS·2H2O (m1) versus temperature (T) in different solute-free mass fractions of aqueous sulfuric acid solutions (w03): (cyan) w03 = 0.2; (blue) w03 = 0.3; (green) w03 = 0.4; (red) w03 = 0.5; (black) w03 = 0.6.
On the one hand, the sodium sulfate in the mixture 1 is consumed in the neutralization process, so no sodium sulfate will be entrained to the alkali fusion process, which can reduce the alkali fusion reaction temperature and decrease energy consumption. On the other hand, less sodium hydroxide will be consumed and no water will be produced in the alkali fusion process. As shown in Figure 4, the neutralization process includes four steps. In step 1, the mixture 1 (molar ratio of 1,5-H2NDS to sodium sulfate is defined as η) is dissolved in a certain amount of water (moles of water for per mole of Na2SO4 is defined as mW, which is the minimum amount of water needed to dissolve the solid at the reaction temperature) and reacts at the reaction temperature (defined as TR). The minimum amount of water mW depends on η and TR. Therefore, only η 11828
DOI: 10.1021/acs.iecr.8b02165 Ind. Eng. Chem. Res. 2018, 57, 11826−11832
Article
Industrial & Engineering Chemistry Research
Finally, in step 4, cake 2 containing almost all 1,5-H2NDS and a certain amount of sodium sulfate are cycled to step 1 for neutralization. 3.4. Optimum Conditions of New Strategy. In this section, the optimum conditions in the new strategy are discussed and determined. All experimentations are described in section 2.2. 3.4.1. Effect of the Factors in Step 1. In order to confirm the optimum conditions, the neutralization reaction was carried out at different conditions and the results are shown in Table 3. Table 3. Results of Neutralization Reaction at Different Conditions
Figure 3. Plot of molality solubilities of 1,5-Na2NDS·H2O (m2) versus temperature (T) in different solute-free mass fractions of aqueous sulfuric acid solutions (w03): (cyan) w03 = 0.2; (blue) w03 = 0.3; (green) w03 = 0.4; (red) w03 = 0.5; (black) w03 = 0.6.
and TR are optimized as neutralization reaction conditions in section 3.4. Next, in step 2, according to the solubility data, a certain amount of sulfuric acid is added to mixture 2. The critical factor in this step is the concentration of sulfuric acid (defined as x1), which should be controlled to ensure 1,5-Na2NDS is precipitated in cake 1, while 1,5-H2NDS remains dissolved in filtrate 1. After filtration, cake 1 is sent to the process of alkali fusion. Then, in step 3, filtrate 1 is evaporated until the concentration of sulfuric acid reaches a certain value (defined as x2), at which 1,5-H2NDS is nearly precipitated completely in cake 2. After filtration, the filtrate 2 is cycled to step 2 to separate 1,5-Na2NDS and 1,5-H2NDS. Thus it is apparent that x2 is an important factor in this step
expt no.
η
TR (K)
mW (mol/mol of Na2SO4)
yield
1 2 3 4 5 6 7 8 9 10 11
1 2 2.5 2.5 2.5 2.5 3 3 3 3 4
353.15 353.15 323.15 333.15 343.15 353.15 323.15 333.15 343.15 353.15 353.15
108.8 115.5 163.9 147.1 133.2 118.2 166.4 159.4 142.9 122.9 130.3
0.72 0.87 0.60 0.75 0.86 0.98 0.88 0.91 0.96 0.97 0.95
To determine the optimum η, the experiments numbered 1, 2, 6, 10, and 11 are carried out at 353.15 K and the results are shown in Figure 5. It is found that when TR is 353.15 K, mW increases with η. Meanwhile, as η increases, the yield of 1,5Na2NDS increases at first, followed by a slight decrease. The main reason is that mW increases with η, which makes part of the generated 1,5-Na2NDS dissolve and the yield decreases. In consideration of yield and mW, the optimal condition of η is set as 2.5, at which the yield of 1,5-Na2NDS is maximized. Meanwhile, to determine TR, a series of experiments are carried out when η is set to be 2.5 and 3. The results of experiments numbered 3−10 are shown in Figure 6. It can be
Figure 4. New strategy of producing 1,5-DHN. The top dashed frame is described in detail in the bottom dashed frame. 11829
DOI: 10.1021/acs.iecr.8b02165 Ind. Eng. Chem. Res. 2018, 57, 11826−11832
Article
Industrial & Engineering Chemistry Research
Figure 5. Results of mW and yield of 1,5-Na2NDS in neutralization reaction with different η values at 353.15 K: (■) values of mW; (□) values of yield.
Figure 7. Solubility data and α at 298.15 K in different mass fraction of sulfuric acid: (■) solubilities of 1,5-Na2NDS at 298.15K; (□) solubilities of 1,5-H2NDS at 298.15 K; (●) variation tendency of α.
According to the obtained solubility data, the maximum solubility discrepancy is found at x1 = 0.2. To fully investigate the relationship between the mass fraction of sulfuric acid (x1) and the yield of 1,5-Na2NDS, we conducted experiments with different values of x1 by adding concentrated sulfuric acid to mixture 2. As a comparison, a contrasting experiment is carried out without sulfuric acid added (x1 = 0.044). Meanwhile, x1 = 0.1 is also studied. The results are shown in Figure 8.
Figure 6. Results of mW and yield of 1,5-Na2NDS in neutralization reaction at different conditions: (■) values of mW at η = 2.5; (●) values of mW at η = 3; (□) values of yield at η = 2.5; (○) values of yield at η = 3.
seen that, at each η value, with the increase of temperature TR,mW decreases while the yield of 1,5-Na2NDS increases. The results are consistent with the solubility data. When TR is kept constant, mW increases with η. The yield of 1,5-Na2NDS at η = 3 is higher than that of η = 2.5 when TR is lower than 353.15 K. But at TR = 353.15 K, the yield at η = 2.5 is higher than that of η = 3. Considering mW and the yield of reaction, TR is set as 353.15 K. Besides, at η = 3, the yields of 1,5-Na2NDS over the temperature range from 343 to 353 K are stable and above 0.95. Therefore, in industrial conditions where the reaction temperature is not precisely controlled, η = 3 also can be considered. 3.4.2. Effect of Amount of Sulfuric Acid Added in Step 2. After the neutralization reaction, the generated 1,5-Na2NDS needs to be separated from mixture 2 in step 2. The separation is dependent on the solubility discrepancy of 1,5-H2NDS and 1,5-Na2NDS, which is defined as α = m1/m2
Figure 8. Effect of mass fraction of sulfuric acid on yield of 1,5Na2NDS. Reaction conditions: molar ratio of 1,5-H2NDS to sodium sulfate η = 2.5, reaction temperature TR = 353.15 K, amount of water mW = 118.2 mol/mol of sodium sulfate.
It can be seen that the yield is more than 0.98 at x1 = 0.3. However, the yield is only 0.65 at x1 = 0.2. This is because at x1 = 0.2, 1,5-Na2NDS is highly soluble and part of the 1,5Na2NDS is dissolved in the solution. Therefore, the optimum condition for separating 1,5-Na2NDS from mixture 2 is determined as x1 = 0.3. 3.4.3. Effect Amount of Vaporized Water in Step 3. In step 3, after vaporizing a certain amount of water to increase the concentration of sulfuric acid, 1,5-H2NDS is separated from filtrate 1 by filtration again. In theory, at x2 ≥ 0.5, the yield of 1,5-H2NDS is more than 0.98 according to the determined
(4)
The values of α at 298.15 K between 1,5-H2NDS and 1,5Na2NDS in aqueous sulfuric acid solutions are shown in Figure 7. 11830
DOI: 10.1021/acs.iecr.8b02165 Ind. Eng. Chem. Res. 2018, 57, 11826−11832
Article
Industrial & Engineering Chemistry Research ORCID
solubility data. Considering the energy consumption and yield together, the operating condition of x2 is set as 0.5. In summary, the neutralization reaction is carried out at TR = 353.15 K and η = 2.5. Then, 1,5-Na2NDS is separated at x2 = 0.3. After separation, water is evaporated and 1,5-H2NDS is separated at x2 = 0.5 in step 3, in which the yield of 1,5H2NDS can reach 0.98. Because cake 2 is cycled in the new strategy, the purity of 1,5-H2NDS in cake 2 is not measured in this work. 3.4.4. Discussion of New Strategy. The drawbacks in the traditional process can be overcome by two improvements in the new strategy. One is that the sodium chloride is replaced by sodium sulfate in the salting-out process, which not only avoids the formation of hydrogen chloride gas but also benefits the following neutralization. The other improvement is that a neutralization process is introduced after the salting-out process to ensure only 1,5-Na2NDS is sent to the following alkali fusion process. Besides, sulfuric acid generated in the neutralization reaction can be reused in the new strategy. Moreover, the reaction temperature decreases and less sodium hydroxide are consumed in alkali fusion. Apart from the abovementioned advantages, it is realized that the new strategy is more complex, and the water evaporation requires additional energy supply. In addition, the feasibility of reusing filtrate 2 needs to be further researched.
Qing Xia: 0000-0003-0941-8852 Notes
The authors declare no competing financial interest.
■
4. CONCLUSIONS An optimal design of the neutralization process in 1,5-DHN production has been proposed, which is based on the solubility difference of 1,5-H2NDS·2H2O and 1,5-Na2NDS·H2O in aqueous sulfuric acid solutions. The solubility data have been measured and correlated with the Apelblat model. The calculated results show good agreement with the experimental data. In the new strategy, sodium chloride is replaced by sodium sulfate in the salting-out process and the neutralization process is introduced. After the neutralization reaction, 1,5Na2NDS and 1,5-H2NDS are filtrated out by adjusting the concentration of sulfuric acid. The optimal conditions for the neutralization reaction are set as TR = 353.15 K and η = 2.5. Meanwhile, the optimal concentrations of sulfuric acid aqueous solution for separation are x1 = 0.3 for 1,5-Na2NDS and x2 = 0.5 for 1,5-H2NDS, respectively. The yields of both 1,5H2NDS and 1,5-Na2NDS have reached 0.98. In the new strategy, all products in the neutralization process have been used and recycled, which is more environmentally friendly than the traditional strategy.
■
ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.iecr.8b02165.
■
REFERENCES
(1) Tu, W.; Chen, J. Naphthalene curing agent used for preparing UV-curable pressure-sensitive adhesive for pressure-sensitive adhesive tape comprises 1,5-dihydroxynaphthalene and acryloyl chloride. CN Patent 106,867,433, 2017. (2) Shvydkiv, O.; Limburg, C.; Nolan, K.; Oelgemoller, M. Synthesis of juglone 5-hydroxy-1,4-naphthoquinone in a falling film microreactor. J. Flow Chem. 2012, 2 (2), 52−55. (3) Lycka, A.; Vrba, Z.; Vrba, M. N-15, C-13 and H-1 NMR spectra and azo-hydrazone tautomerism of some phenylazo compounds derived from 1,3-and 1,5-dihydroxynaphthalene. Dyes Pigm. 2000, 47 (1−2), 45−51. (4) Chen, Y. Preparing reactive dye fixing agent involves adding polyoxyethylene diamine, epichlorohydrin, triethanolamine, 1,5dihydroxynaphthalene and diallylamine hydrochloride into flask equipped with stirrer, thermometer and reflux condenser. CN Patent 105,463,889, 2016. (5) Zhang, J. H.; Yang, L.; Ruan, X.; Sheng, Z. L.; Yu, M. F.; Zheng, B. S.; Zhang, J. Y.; Li, X. X.; Zhao, Y. X.; Wang, Q. Synthesis and herbicidal activity of 4, 8-DHT and its derivates. Ind. Crops Prod. 2018, 111, 755−767. (6) You, A.; Li, Y.; Lao, S.; Feng, A.; Ma, L.; Zhang, Z.; Qiu, W. Application of hydroxyl group-containing aryl compound, particularly 1,5-dihydroxynaphthalene and/or 2,2′-biphenol for activating tyrosinase, and preparing tanning cosmetics and medicine for treating vitiligo. CN Patent 106,420,678, 2017. (7) Chen, N.; Li, J.; Yang, S.; Zhong, W. Preparing 1,5diaminonaphthalene comprises taking deionized water, 1,5- dihydroxynaphthalene, and sulfite, crystallizing, filtering the solid content, collecting mother liquor, washing solid content with deionized water and drying. CN Patent 105,884,622, 2016. (8) Hu, G.; Zhang, W.; Hu, L.; Sun, X.; Wo, Q.; Zhang, H.; Wu, L.; Song, J. Identification of four dihydroxynaphthalene isomers involves preparing sample with anhydrous ethanol solvent, applying differential solution, recording oscillation pattern via oscillation system, and analyzing sample solution. CN Patent 106,996,949, 2017. (9) Liu, B.; Chen, Y.; Wang, X.; Wang, G.; Liu, J.; Zhou, S.; Hu, X.; He, M. New naphthalene-furan-based photovoltaic material useful in preparing solar cells, prepared by e.g. mixing 1,5-dihydroxynaphthalene, 1-bromo-2-undecanone and potassium carbonate and eluting with silica gel column. CN Patent 106,946,912, 2017. (10) Feng, W.; Huang, X.; Yang, Y.; Zhou, Z.; Lu, H. Producing 1,5dihydroxynaphthalene involves adding sodium hydroxide, water and 1,5-naphthalene sulfonate in reaction kettle, where mixture is stirred to obtain reaction solution. CN Patent 105,503,532, 2016. (11) Shi, H.; Lin, F.; Lu, K. Preparing 1,5-dihydroxynaphthalene comprises performing sulfonation reaction with refined naphthalene and sulfonating agent, salting out, heating and reacting the reaction solid with water and inorganic strong alkali in presence of catalyst. CN Patent 103,739,449, 2013. (12) Ge, C.; Sun, D.; Xue, W.; Zhang, J. Production of 1,5dihydroxynaphthlene by reacting refined naphthalene with fuming sulfuric acid, diluting, adding sulfonated mother liquor into alkalifused product, and introducing part of alkali-fused mother liquor to diluting technique. CN Patent 102,442,888, 2011. (13) Zhao, R. X.; Pei, K. K.; Zhang, G. L.; Xia, Q.; Zhang, F. B. Solubilities of sodium 1-and 2-naphthalenesulfonate in aqueous sodium hydroxide solutions and its application for optimizing the production of 2-naphthol. Ind. Eng. Chem. Res. 2017, 56 (36), 10193− 10198. (14) Wang, W. C.; Zhang-Bian, Y. Y.; Zhang, G. L.; Xia, Q.; Zhang, F. B. Solubility of disodium 4,4’-dinitrobibenzyl-2,2’-disulfonate in
Tables of experimental solubilities of 1,5-H2NDS and 1,5-Na2NDS at Texp in aqueous sulfuric acid solutions; results of HPLC analysis, TGA, and X-ray diffraction of 1,5-H2NDS and 1,5-Na2NDS; 1H NMR spectroscopy of cake 1 (PDF)
AUTHOR INFORMATION
Corresponding Authors
*Tel.: 86-22-27408778. E-mail:
[email protected]. *Tel.: 86-22-27408778. E-mail:
[email protected]. 11831
DOI: 10.1021/acs.iecr.8b02165 Ind. Eng. Chem. Res. 2018, 57, 11826−11832
Article
Industrial & Engineering Chemistry Research aqueous organic solutions and its effects on the oxidation reaction of DSD acid synthesis. Fluid Phase Equilib. 2016, 427, 303−307. (15) Liu, S. L.; Li, H. M.; Han, G.; Li, Y. X.; Zhang, G. L.; Zhang, F. B.; Xia, Q. Measurement and Correlation of the Solubility of Sodium 2-Chlorotoluene-4-sulfonate in Selected Pure Solvents and Aqueous Organic Solutions. J. Chem. Eng. Data 2016, 61 (2), 820−826. (16) Zhang, L.; Jing, H.; Zhu, W. Y.; Zhang, F. B.; Zhang, G. L.; Xia, Q. Measurement and correlation of solubility of 4-chloro-2,5dimethoxynitrobenzene and 4-chloro-2,5-dimethoxyaniline in methanol, ethanol, xylene and toluene. J. Chem. Thermodyn. 2015, 80, 142−146. (17) Zhu, W. Y.; Gu, Y.; Zhang, L.; Jing, H.; Liu, B.; Zhang, F. B.; Zhang, G. L.; Xia, Q. Solubility of Na2CO3and NaHCO3in aqueous sodium sulfate solutions and its application to separating Na2CO3and Na2SO4salt mixtures. Ind. Eng. Chem. Res. 2015, 54 (19), 5345−5348. (18) Zhang, H.; Xia, Q.; Yang, Y.; Zhang, F. B.; Zhang, G. L. Solubility of dimethyl terephthalate and monomethyl terephthalate in the methanol aqueous solution and its application to recycle monomethyl terephthalate from crude dimethyl terephthalate. Ind. Eng. Chem. Res. 2013, 52 (14), 5230−5234. (19) Yu, C.; Zeng, Z. X.; Xue, W. L. Measurement and correlation of the solubility of hexaquonickel(II) bis(p-toluenesulfonate) in water plus ethanol solvents within 288.15−333.15 K. Ind. Eng. Chem. Res. 2015, 54 (15), 3961−3967. (20) Wu, H.; Dang, L.; Wei, H. Solid-liquid phase equilibrium of nicotinamide in different pure solvents: measurements and thermodynamic modeling. Ind. Eng. Chem. Res. 2014, 53 (4), 1707−1711. (21) Zhao, W.; Zou, W.; Liu, T.; Zhang, F. B.; Zhang, G. L.; Xia, Q. Solubilities of p-toluenesulfonic acid mnohydrate and sodium ptoluenesulfonate in aqueous sulfuric acid solutions and its application for preparing sodium p-toluenesulfonate. Ind. Eng. Chem. Res. 2013, 52 (51), 18466−18471. (22) Yang, Y.; Xia, Q.; Zhang, H.; Zhang, F. B.; Zhang, G. L. Investigation the solubility difference of sodium 4-nitrotoluene-2sulfonate and 4-nitrotoluene-2-sulfonic acid in (sulfuric acid plus water) system. Fluid Phase Equilib. 2013, 358, 151−155.
11832
DOI: 10.1021/acs.iecr.8b02165 Ind. Eng. Chem. Res. 2018, 57, 11826−11832
