LiquidâLiquid Equilibrium for Ternary Systems of Water + 2,2,3,3

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

Liquid−Liquid Equilibrium for Ternary Systems of Water + 2,2,3,3-Tetrafluoro-1-propanol + Anisole/1-Octanol at 298.2, 308.2, and 318.2 K Bing Jia,† Liping Wang,† Mengmeng Yan,‡,† Hai Liu,† Yingmin Yu,† and Qingsong Li*,† †

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The State Key Lab of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum-East China, Qingdao, Shandong 266580, P. R. China ‡ Dongying Vocational College of Science & Technology, Dongying, Shandong 257335, P. R. China S Supporting Information *

ABSTRACT: Liquid−liquid equilibrium (LLE) data for ternary systems of water + 2,2,3,3-tetrafluoro-1-propanol + anisole/1-octanol were determined at temperatures of 298.2, 308.2, and 318.2 K under 101.3 kPa. The distribution coefficients and separation factors were calculated from experimental LLE data, which indicated that anisole/1-octanol extracted 2,2,3,3-tetrafluoro-1-propanol from aqueous solution with high efficiency. The consistency of the experimental LLE data was assessed by the Othmer−Tobias and Hand equations. Meanwhile, the NRTL and UNIQUAC models were successfully applied to regress and correlate the experimental data, presenting the root-mean-square deviations (RMSD) less than 1.0%. The relevant binary interaction parameters of these two models were also regressed.

1. INTRODUCTION 2,2,3,3-Tetrafluoro-1-propanol (TFP, C3H4F4O), as an important fluoroalcohol, is widely used for industrial applications. TFP can be used as solvent for coating dyes in manufacturing DVD-R or CD-R recording media.1,2 TFP can be also used as cleaning agents in dry cleaning,3 as well as an important ingredient in the formulation of surfactant and fabric finishing agents.4−6 Owing to the extensive use of TFP in industry, it is inevitable to form different concentrations of TFP aqueous solutions. TFP is expensive and unfriendly to the environment;7 recovering TFP economically and effectively from wastewater is of great importance. However, TFP and water can form an azeotropic mixtures at a TFP/water composition of 72.5/27.5 (by weight) (azeotropic point: 365.7 K, at atmospheric pressure),8,9 so it is hard to obtain highly purified TFP from the aqueous solutions. For that reason, the simple TFP distillation could not be an effective method for TFP upgrading. Liquid−liquid extraction (LLE) is very important to industrial applications for separating azeotropic mixtures.10 There are only a few works that have been reported with the LLE systems for TFP extracted from aqueous solutions.11 Therefore, the selection of more appropriate solvents in the TFP extracting process is the primary consideration. In this work, anisole and 1-octanol were selected as the extraction solvents for recovering TFP from aqueous solutions. Moreover, the liquid−liquid equilibrium data for ternary systems of water + 2,2,3,3-tetrafluoro-1-propanol + anisole/1-octanol were determined at 298.2, 308.2, and 318.2 K under 101.3 kPa. To the best of our knowledge, these LLE data © XXXX American Chemical Society

for the investigated systems have never been reported in any literature. The Othmer−Tobias and Hand equations were used to confirm consistency of the experimental data. Furthermore, the Non-Random Two-Liquid (NRTL)12and Universal QuasiChemical (UNIQUAC)13 models were applied to regress and correlate the experimental LLE data.

2. EXPERIMENTAL SECTION 2.1. Materials. The detailed information on all the chemicals used in this work is presented in Table 1. 2,2,3,3-Tetrafluoro1-propanol (TFP) was purchased from J&K Scientific Ltd. Anisole and 1-octanol were purchased from Aladdin reagent company (Shanghai, China). All chemicals were used without further purification. Distilled water was employed in all experiments. 2.2. Apparatus and Procedures. The equilibrium experiments for ternary systems of water + TFP + anisole/1octanol were determined at 298.2, 308.2, and 318.2 K under 101.3 kPa. Our previous works have presented the details about equipment and the experimental method.9,14−17 In each experiment, the mixture of water, anisole, or 1-octanol and TFP was vigorously agitated by a magnet at desired temperature for 1.5 h and then left to settle for 12 h to achieve the phase equilibrium. The thermostatic bath controlled the experimental temperature with a precision of ±0.1 K. Received: May 13, 2018 Accepted: July 23, 2018

A

DOI: 10.1021/acs.jced.8b00393 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

After, the ternary mixture was divided into the organic rich phase and aqueous phase. The compositions were taken from each phase with a syringe and analyzed by the gas chromatograph (GC6820, Agilent Technologies) using TFP as an internal standard substance. The gas chromatograph was equipped with a thermal conductivity detector (TCD) and a Porapak N column (3 mm × 3 m). The operating conditions of the gas chromatograph were shown as follows: the temperature of the injector and detector was 523.2 K, and the column oven temperature started at 373.2 K, increased to 523.2 K at a rate of 20 K/min, and then was maintained at 523.2 K for 1 min. All samples were measured at least three times, and the mean value was adopted as the sample composition.9

Table 1. Details of the Chemicals Used in This Work chemical name 2,2,3,3tetrafluoro1-propanol anisole 1-octanol distilled water

source J&K Scientific Ltd. Aladdin reagent company Aladdin reagent company self-made

mass fraction purity GC analysis

purification method

>0.98a

none

76-37-9

>0.99a

none

100-66-3

>0.99a

none

111-87-5

−

none

7732-18-5

CAS

a

The purity of all chemical was analyzed by the suppliers.

Table 2. Experimental LLE Data for Ternary Systems of Water (1) + TFP (2) + Anisole/1-Octanol (3) at 298.2, 308.2 K, and 318.2 K under 101.3 kPaa,b organic phase solvent anisole 298.2 K

anisole 308.2 K

anisole 318.2 K

1-octanol 298.2 K

1-octanol 308.2 K

aqueous phase

wI1

wI2

wI3

wII1

wII2

wII3

D

S

0.0025 0.0034 0.0052 0.0066 0.0107 0.0141 0.0164 0.0236 0.0247 0.0286 0.0289 0.0035 0.0096 0.0110 0.0123 0.0173 0.0206 0.0211 0.0226 0.0241 0.0017 0.0081 0.0086 0.0112 0.0122 0.0138 0.0147 0.0227 0.0249 0.0253 0.0465 0.0491 0.0479 0.0484 0.0519 0.0529 0.0568 0.0559 0.0574 0.0598 0.0635 0.0483 0.0610 0.0639

− 0.0352 0.0737 0.1189 0.1832 0.2208 0.2597 0.2923 0.3153 0.3434 0.3715 − 0.0486 0.0875 0.1238 0.1565 0.1934 0.2617 0.2892 0.3194 − 0.0287 0.0504 0.0769 0.1044 0.1350 0.1632 0.2245 0.2482 0.2719 − 0.0497 0.1025 0.1508 0.1899 0.2320 0.2606 0.2899 0.3143 0.3394 0.3634 − 0.0560 0.0993

0.9975 0.9614 0.9211 0.8745 0.8061 0.7651 0.7239 0.6841 0.6600 0.6280 0.5996 0.9965 0.9418 0.9015 0.8639 0.8262 0.7860 0.7172 0.6882 0.6565 0.9983 0.9632 0.9410 0.9119 0.8834 0.8512 0.8221 0.7528 0.7269 0.7028 0.9535 0.9012 0.8496 0.8008 0.7582 0.7151 0.6826 0.6542 0.6283 0.6008 0.5731 0.9517 0.8830 0.8368

0.9977 0.9664 0.9384 0.9115 0.8835 0.8673 0.8555 0.8464 0.8389 0.8298 0.8228 0.9967 0.9644 0.9423 0.9249 0.9106 0.8967 0.8712 0.8600 0.8501 0.9949 0.9774 0.9626 0.9480 0.9310 0.9199 0.9078 0.8846 0.8761 0.8677 0.9985 0.9844 0.9681 0.9501 0.9363 0.9157 0.9047 0.8912 0.8777 0.8634 0.8448 0.9985 0.9831 0.9706

− 0.0301 0.0576 0.0844 0.1127 0.1282 0.1406 0.1501 0.1576 0.1667 0.1736 − 0.0330 0.0547 0.0724 0.0869 0.1007 0.1258 0.1368 0.1474 − 0.0202 0.0336 0.0497 0.0638 0.0777 0.0898 0.1125 0.1213 0.1301 − 0.0135 0.0296 0.0476 0.0612 0.0816 0.0926 0.1061 0.1198 0.1331 0.1517 − 0.0143 0.0267

0.0023 0.0035 0.0040 0.0041 0.0038 0.0045 0.0039 0.0035 0.0035 0.0035 0.0036 0.0033 0.0026 0.0030 0.0027 0.0025 0.0026 0.0030 0.0032 0.0025 0.0051 0.0024 0.0038 0.0023 0.0052 0.0024 0.0024 0.0029 0.0026 0.0022 0.0015 0.0021 0.0023 0.0023 0.0025 0.0027 0.0027 0.0027 0.0025 0.0035 0.0035 0.0015 0.0026 0.0027

− 1.169 1.280 1.409 1.626 1.722 1.847 1.947 2.001 2.060 2.140 − 1.471 1.598 1.711 1.801 1.920 2.080 2.113 2.167 − 1.418 1.501 1.549 1.637 1.737 1.817 1.995 2.046 2.090 − 3.681 3.463 3.168 3.103 2.843 2.814 2.732 2.624 2.550 2.396 − 3.916 3.719

− 332.4 230.9 194.6 134.2 105.9 96.4 69.84 67.95 59.77 60.93 − 144.29 131.39 120.16 86.18 73.23 70.56 64.45 59.14 − 172.0 169.0 131.4 125.0 116.0 112.1 77.88 72.01 71.56 − 73.81 69.99 62.19 55.98 49.21 44.82 43.56 40.12 36.82 31.87 − 63.11 56.49

B



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Table 2. continued organic phase solvent

1-octanol 318.2 K

aqueous phase

I

w1

wI2

wI3

0.0649 0.0626 0.0644 0.0633 0.0675 0.0661 0.0664 0.0523 0.0544 0.0533 0.0549 0.0558 0.0583 0.0605 0.0601 0.0633

0.1354 0.1700 0.2032 0.2306 0.2593 0.2826 0.3121 − 0.0537 0.0831 0.1111 0.1382 0.1649 0.1940 0.2182 0.2426

0.7997 0.7674 0.7324 0.7061 0.6732 0.6513 0.6215 0.9477 0.8919 0.8636 0.8340 0.8060 0.7768 0.7455 0.7217 0.6941

II

w

1

0.9577 0.9484 0.9346 0.9248 0.9184 0.9063 0.8972 0.9977 0.9778 0.9682 0.9604 0.9537 0.9444 0.9309 0.9229 0.9103

wII2

wII3

D

S

0.0394 0.0486 0.0621 0.0719 0.0781 0.0894 0.0993 − 0.0154 0.0258 0.0336 0.0420 0.0515 0.0645 0.0734 0.0848

0.0029 0.0030 0.0033 0.0033 0.0035 0.0043 0.0035 0.0023 0.0068 0.0060 0.0060 0.0043 0.0041 0.0046 0.0037 0.0049

3.437 3.498 3.272 3.207 3.320 3.161 3.143 − 3.498 3.220 3.311 3.295 3.200 3.006 2.972 2.862

50.71 52.99 47.49 46.86 45.17 43.34 42.47 − 62.88 58.52 57.94 56.34 51.82 46.28 45.65 41.17

a

Standard uncertainties u are u(T) = 0.1 K, u(p) = 1 kPa, u(w) = 0.0050. bw1: mass fraction of water. w2: mass fraction of TFP. w3: mass fraction of anisole/1-octanol.

The GUM and associated guidelines were used to calculate the standard uncertainty of each sample composition in two separate phases.9,18−20The standard uncertainty of all measured compositions is better than ±0.0050 in mass fraction.

3. RESULTS AND DISCUSSION 3.1. Experimental LLE Data. The LLE data (in mass fraction) for ternary systems of water + TFP + anisole/1-octanol at 298.2, 308.2, and 318.2 K under 101.3 kPa are tabulated in Table 2. Meanwhile, the corresponding ternary phase diagrams for each ternary system are plotted in Figures 1−6. The mutual

Figure 2. Ternary phase diagram for the system of water + TFP + anisole at 308.2 K under 101.3 kPa: (□) experimental data; (▲) UNIQUAC model; (●) NRTL model.

The capacity of anisole/1-octanol to extract TFP from aqueous solution is assessed by distribution coefficients (D)28 and separation factors (S):29 D = w2I /w2II

(1)

S = (w2I /w2II)/(w1I/w1II)

(2)

where superscripts I and II stand for organic phase and aqueous phase, respectively; w2 and w1 denote the mass fractions of TFP and water, respectively. Table 2 and Figures 7 and 8 summarize the corresponding distribution coefficients and separation factors for the studied systems. The result indicates that anisole and 1-octanol provide a high distribution coefficient and high separation factors for extracting TFP from aqueous solution. Both the concentration of the TFP in aqueous solution and temperature effect on the distribution coefficients and separation factors are known to be important.9As can be seen in Figures 7 and 8, the increasing TFP concentration in the aqueous phase led to the decrease of the distribution coefficients and separation factors of 1-octanol;


binary solubilities between water−anisole and water−1-octanol are listed in Table 3 and compared with the previous literature data.21−26 As shown in Table 3, the literature data of binary solubilities are relatively in agreement with those of this work. The different methods of measurement and procedure or accuracy limitation and the precision of the measurement could result the deviations.27 C



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Figure 6. Ternary phase diagram for the system of water + TFP + 1-octanol at 318.2 K under 101.3 kPa: (□) experimental data; (▲) UNIQUAC model; (●) NRTL model.

Table 3. Solubility of Binaries in Terms of Mass Fraction for Anisole−Water and 1-Octanol−Water Systems and Comparison with Literature Dataa water in anisole/ 1-octanol T, K

wexp.

wlit.

wexp.

wlit.

anisole

298.2

0.0025

0.0023

1-octanol

308.2 318.2 298.2

0.0035 0.0017 0.0465

308.2

0.0483

318.2

0.0523

0.0019b21 − 0.0022b21 0.0019b21 0.049623 0.048824 0.044825 0.025026 0.050523 0.050124 0.0481b25 0.051723

0.0019b21 0.001522 0.0019b21 0.0025b21 0.000423 − 0.000525 0.003926 0.000523 − 0.0007b25 0.000523

component


anisole/1-octanol in water

0.0033 0.0051 0.0015

0.0015

0.0023

a

Standard uncertainties u are u(T) = 0.1 K, u(p) = 1 kPa, u(w) = 0.0050. (The uncertainties of measurements are more consistent with 0.0050 in mass fraction for both phases). bThe binaries were taken from interpolation of the data from literature.21,25

anisole and decrease of separation factors of anisole; temperature has an effect on the separation factors of anisole, with low temperature being conducive to TFP extraction in this system. The consistency of the experimental LLE data was assessed with the Othmer−Tobias30,31and Hand32,33 equations as follows: ln[(1 − w3I)/w3I] = a1 + b1 ln[(1 − w1II)/w1II]

(3)

ln(w2I /w3I) = a 2 + b2 ln(w2II/w1II)

(4)

where a1, b1, a2, and b2 are the parameters of the Othmer− Tobias and Hand equations, respectively. wI2 and wI3 are the mass fractions of TFP and solvent in the organic phase; wII1 and wII2 are mass fractions of water and TFP in the aqueous phase, respectively. The parameter values of Othmer−Tobias and Hand correlations, together with the regression coefficients (R2), are given in Table 4. Meanwhile, the Othmer− Tobias and Hand plots are also shown in Figures 9 and 10. All of the regression coefficients (R2) are more than 0.98,


temperature has an insignificant effect on this system. In addition, the increasing TFP concentration in the aqueous phase led to the increase of the distribution coefficients of D



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Figure 7. Distribution coefficient plotted against with mass fraction of TFP in the aqueous phase at 101.3 kPa: (▲) anisole, at T = 298.2 K, (▼) anisole, at T = 308.2 K, (★) anisole, at T = 318.2 K, (■) 1-octanol, at T = 298.2 K, (●) 1-octanol, at T = 308.2 K, (◆) 1-octanol, at T = 318.2 K.

Figure 9. Othmer−Tobias equation plots for the ternary systems of water + TFP + solvents at 101.3 kPa. (▲) Anisole, at T = 298.2 K, (▼) anisole, at T = 308.2 K, (★) anisole, at T = 318.2 K, (■) 1-octanol, at T = 298.2 K, (●) 1-octanol, at T = 308.2 K, (◆) 1-octanol, at T = 318.2 K.

Figure 8. Separation factor plotted against with mass fraction of TFP in the aqueous phase at 101.3 kPa: (▲) anisole, at T = 298.2 K, (▼) anisole, at T = 308.2 K, (★) anisole, at T = 318.2 K, (■) 1-octanol, at T = 298.2 K, (●) 1-octanol, at T = 308.2 K, (◆) 1-octanol, at T = 318.2 K.

Figure 10. Hand equation plots for the ternary systems of water + TFP + solvents at 101.3 kPa. (▲) Anisole, at T = 298.2 K, (▼) anisole, at T = 308.2 K, (★) anisole, at T = 318.2 K, (■) 1-octanol, at T = 298.2 K, (●) 1-octanol, at T = 308.2 K, (◆) 1-octanol, at T = 318.2 K.

which indicates a good consistency of the experimental data in this work. 3.2. Correlation of LLE Data. In this work, the NRTL12 and UNIQUAC13 models were applied to regress and correlate the experimental LLE data. The UNIQUAC structural

parameters r (molecular-geometric volume) and q (molecular-geometric surface) taken from literature9,11and Aspen Plus (Version 8.4) are shown in Table 5. After preliminary tests, the optimum value of NRTL nonrandomness parameters α was set to 0.3 for all systems. The binary interaction parameters of

Table 4. Othmer−Tobias and Hand Equation Parameters (a, b) and Regression Coefficients (R2) for the Ternary Systems of Water (1) + TFP (2) + Solvents (3) Systems O-T equation

Hand equation 2

solvent

a1

b1

R

anisole 298.2 K anisole 308.2 K anisole 318.2 K 1-octanol 298.2 K 1-octanol 308.2 K 1-octanol 318.2 K

1.8388 1.7046 1.4879 1.0344 1.1743 1.2793

1.5522 1.3865 1.2983 0.8010 0.8014 0.9017

0.9847 0.9949 0.9887 0.9955 0.9905 0.9968 E

a2

b2

R2

1.6917 1.6762 1.4414 −1.2617 −1.4893 −1.3404

1.4856 1.3974 1.3023 1.0469 0.9832 0.9959

0.9860 0.9959 0.9937 0.9996 0.9976 0.9983



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Table 5. Structural Parameters (r and q) for the UNIQUAC component

r

q

water anisole 1-octanol 2,2,3,3-tetrafluoro-1-propanol

0.9200 4.1668 6.1516 3.4529

1.4000 3.2080 5.2120 3.1920

experimental LLE data and calculated binary interaction parameters in this work can be used in design and optimization of the TFP extraction process from aqueous solutions.

■

ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.8b00393.

NRTL and UNIQUAC models were obtained by minimizing the objective function (OF):9,34,35 M

OF =

2

3

■

∑ ∑ ∑ (wijkexp − wijkcal)2 (5)

k=1 j=1 i=1 exp

cal

where w and w are experimental mass fraction and calculated mass fraction, respectively. Subscripts i, j, k, and M refer to the components, the phases, the tie lines, and the number of tie lines, respectively. The binary interaction parameters of both models are shown in Table 6. The calculated values from the correlations of NRTL and UNIQUAC models are tabulated in Tables S1−S6 (see the Supporting Information) and also included in Figures 1−6. All these results show that the calculated values are in good agreement with the experimental data. Meanwhile, the root-mean-square deviation (RMSD) values between experimental and calculated were evaluated according to the following equation:9,36

Calculated values of water + TFP + anisole/1-octanol ternary systems obtained from NRTL and UNIQUAC models are tabulated in Tables S1−S6 (PDF)

AUTHOR INFORMATION

Corresponding Author

*(Q.L.) E-mail: [email protected]. ORCID

Yingmin Yu: 0000-0002-0444-232X Qingsong Li: 0000-0003-1425-8822 Notes

The authors declare no competing financial interest.

■

REFERENCES

(1) Wang, K. Y.; Chung, T. S.; Rajagopalan, R. Dehydration of tetrafluoropropanol (TFP) by pervaporation via novel PBI/BTDATDI/MDI co-polyimide (P84) dual-layer hollow fiber membranes. J. Membr. Sci. 2007, 287, 60−66. (2) Chou, M.; Chang, K. Decomposition of aqueous 2,2,3,3-tetrafluoro-propanol by UV/ O3 process. J. Environ. Eng. 2007, 133, 979− 986. (3) Huang, S. H.; Hung, W. S.; Liaw, D. J.; Lo, C. H.; Chao, W. C.; Hu, C. C.; Li, C. L.; Lee, K. R.; Lai, J. Y. Interfacially polymerized thin-film composite polyamide membranes: effects of annealing processes on pervaporative dehydration of aqueous alcohol solutions. Sep. Purif. Technol. 2010, 72, 40−47. (4) Kujawski, J. K.; Kujawski, W. M.; Sondej, H.; Jarzynka, K.; Kujawska, A.; Bryjak, M.; Rynkowska, E.; Knozowska, K.; Kujawa, J. Dewatering of 2,2,3,3-tetrafluoropropan-1-ol by hydrophilic pervaporation with poly(vinyl alcohol) based PervapTM membranes. Sep. Purif. Technol. 2017, 174, 520−528. (5) Abe, M. Synthesis and applications of surfactants containing fluorine. Curr. Opin. Colloid Interface Sci. 1999, 4, 354−356. (6) Zhao, T.; Zheng, J.; Sun, G. Synthesis and applications of vegetable oil-based fluorocarbon water repellent agents on cotton fabrics. Carbohydr. Polym. 2012, 89, 193−198. (7) Shih, Y. J.; Putra, W. N.; Huang, Y. H.; Tsai, J. C. Mineralization and deflourization of 2,2,3,3-tetrafluoro-1-propanol (TFP) by UV/ persulfate oxidation and sequential adsorption. Chemosphere 2012, 89, 1262−1266. (8) Fumihiko, Y.; Toshiyuki, K. Method for recovering fluoroalcohol. EP 0992476A2, 2000. (9) Li, Q. S.; Jia, B.; Wang, L. P.; Yan, M. M.; Liu, H.; Yu, Y. M. Liquid-liquid equilibrium for ternary systems of water + 2,2,3,3-

1/2 l M 2 3 (w exp − w cal)2 | o o o o ijk ijk o o RMSD% = 100m } ∑∑∑ o o o o 6M ok=1 j=1 i=1 o (6) n ~ exp cal where subscripts M, x , x , k, j, and i are the same as those in the OF equations.9 The RMSD% values are presented in Table 6 which are all less than 0.65. This indicates both NRTL and UNIQUAC models show good representation of the experimental data for the studied systems.

4. CONCLUSIONS Accurate experimental LLE data for ternary systems of water + TFP + anisole/1-octanol were determined at 298.2, 308.2, and 318.2 K under 101.3 kPa. Both anisole and 1-octanol have higher values of distribution coefficients and separation factors, which indicates that extraction of TFP from aqueous solutions by those two solvents is feasible. Othmer−Tobias and Hand equations assessed and checked the consistency of the experimental LLE data. Additionally, the NRTL and UNIQUAC models were used to correlate the studied ternary systems, and the corresponding binary interaction parameters were obtained. The values of RMSD% were less than 0.65, which indicate the calculated results of both NRTL and UNIQUAC models are in good agreement with the experimental data. The

Table 6. Binary Interaction Parameters of NRTL and UNIQUAC Models for the Studied Ternary Systems NRTL parameters solvent anisole

1-octanol

UNIQUAC parameters

i−j

gij−gjj

gji−gii

α

1−2 1−3 2−3 1−2 1−3 2−3

11555.50 16121.88 19315.61 6265.87 17438.36 2396.95

−867.81 7912.25 3971.23 95.39 2877.98 −2985.82

0.30 0.30 0.30 0.30 0.30 0.30 F

RMSD, % 0.39

0.64

uij−ujj

uji−uii

2741.64 2005.16 −426.54 −654.34 1655.04 −1154.82

−680.17 4388.16 1539.39 3660.83 1589.54 1151.50

RMSD, % 0.65

0.56



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LiquidâLiquid Equilibrium for Ternary Systems of Water + 2,2,3,3

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