Extraction Equilibria of Lithium with Tributyl Phosphate, Diisobutyl

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Extraction Equilibria of Lithium with Tributyl Phosphate, Diisobutyl Ketone, Acetophenone, Methyl Isobutyl Ketone, and 2‑Heptanone in Kerosene and FeCl3 Zhiyong Zhou, Shengke Liang, Wei Qin,* and Weiyang Fei State Key Laboratory of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China ABSTRACT: The extraction equilibrium behavior of Li by tributyl phosphate (TBP), diisobutyl ketone, acetophenone, methyl isobutyl ketone, and 2-heptanone in kerosene were investigated. The partition coefficient of Li with TBP in kerosene decreased significantly when the volume concentration of TBP was greater than 60%. The values derived for the partition coefficients of four selected ketones in kerosene were smaller than that of TBP in kerosene. The stoichiometric coefficients between TBP and Li, the stoichiometric coefficients between the four selected ketones and Li, and the apparent equilibrium constant for the extraction reaction equation for TBP and the four ketones in kerosene were obtained. The tendency in extraction with the TBP and four selected ketones in kerosene can be predicted from these parameters. The polar solvents used as diluents for TBP can yield higher Li partition coefficients, strong dilution effects for TBP, and strong polarity and low density of the extracting solvents formed with both polar solvents and TBP.

1. INTRODUCTION Lithium is well-known for its role in technological developments, mostly as a result of its crucial role in energy production and storage. Lithium and its compounds are used extensively in various industrial fields,1−4 especially in Li ion batteries5,6 and in nuclear energy.7 As such, the recovery of Li from salt-lake brine has attracted increased attention recently.8,9 Currently, 80% of the Li produced globally is obtained from salt-lake brine by precipitation10 and the calcination method.11 The salt lakes in some areas of the world, however, such as the Qinghai region in China, exhibit characteristically high Mg to Li ratios, which renders difficult the efficient extraction of Li. Therefore, a solution to the recovery of Li from salt-lake brines in China with high concentrations of Mg2+ is required urgently. Recent research has focused on the recovery from salt-lake brines or seawater using methods such as adsorption on novel nanocrystalline MnO2,12−15 extraction using supported liquid membranes,16 adsorption by acid and sodium Amberlite,17 and the nanofiltration method,18 but few industrial applications are available in China. One potential approach to the recovery of Li from these high Mg brines is using the tributyl phosphate (TBP)/kerosene/FeCl3 extraction process. Tributyl phosphate (TBP) is a popular neutral organophosphorus extractant, and kerosene is a typical diluent. In this system, FeCl3 plays a crucial role as a coextracting agent, improving the extraction efficiency significantly.9 Extraction of Li from salt-lake brine in China by TBP has been studied since the 1980s.19−23 Because of problems such as the third phase, low selectivity, and high price, until now few industrial applications for extraction of Li by TBP can be found in China. Researching the basic extraction equilibrium properties of the TBP/kerosene/FeCl3 system is important for realizing and designing an industrial process for Li recovery. As the polarity of the complexes formed from TBP, Li, and FeCl3 is much stronger than that of TBP, polar solvents with no coordination with PO may yield larger partition coefficients © XXXX American Chemical Society

for Li extraction than kerosene. In this study, diisobutyl ketone (DIBK), acetophenone, methyl isobutyl ketone (MIBK), and 2heptanone were selected as polar solvents and the extraction equilibria of Li with these solvents as extractants or diluents were studied.9 To achieve extraction of Li ions from salt-lake brine in China, the molar concentration of the chloride ions must be greater than 6 mol/L.24 As such, MgCl2 was used as the chloride source because of the characteristicly high Mg:Li ratios in salt-lake brines in China. FeCl3 was selected as the coextracting agent. The extraction equilibria for Li extracted by TBP, DIBK, acetophenone, MIBK, and 2-heptanone in kerosene and TBP in these four ketones were investigated.

2. EXPERIMENTAL SECTION 2.1. Materials. The analytical reagents utilized in this work were >97% pure LiCl, >99% pure TBP, and >99% pure MIBK (Beijing Yili Fine Chemical Co., Ltd., Beijing, China), >99% pure FeCl3 (Tianjin Yongda Chemical Reagent Co., Ltd., Tianjin, China), >98% pure MgCl2 (Beijing Modern Eastern Fine Chemical Co., Ltd., Beijing, China), and >99% pure acetophenone, >98% pure DIBK, and >99.5% pure 2heptanone (Sinopharm Chemical Reagent Beijing Co., Ltd., Beijing, China). The industrial reagent was kerosene (260#, Sinopec Corp., Beijing, China). The characteristic properties of the reagent salts are presented in Table 1, and those of the extractants (TBP, DIBK, acetophenone, MIBK, and 2heptanone) and solvent (kerosene) are provided in Table 2.25 2.2. Methods. All extractions were performed in 50 mL flasks at 25 ± 2 °C. To each flask were added 10 mL of solvent mixture and 10 mL of an aqueous solution containing LiCl, MgCl2, and FeCl3. The flask was agitated for approximately 10 Received: December 17, 2012 Revised: April 12, 2013 Accepted: May 16, 2013

A

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Table 1. Physical Properties of Salts chemical lithium chloride ferric chloride magnesium chloride

formula

av MW (g/mol)

solubility (g/100 g of H2O, 20 °C)

LiCl FeCl3 MgCl2

42.39 162.21 95.22

78.5 55.1 74.0

min and left to settle for 30 min, during which two phases separated from each other. Preliminary trials indicated that the 10 min agitation period was sufficient to achieve the extraction equilibrium in all experimental solutions. A sample of the aqueous (lower) phase was taken using a syringe to measure the solute concentrations. The pH value of the aqueous solution ranged between 0.5 and 1.0 before extraction and from 2.0 to 2.5 after extraction, respectively. 2.3. Analysis. Aqueous phase samples were analyzed for Li, Mg, and Fe ion concentration using an optical atomic absorption spectrometer (Z-5000-AAS, Hitachi, Japan), and the concentrations of cations in the organic phase were calculated based on the mass balance of ionic compounds. Preliminary work, in which the cation concentrations in the organic phase were determined by evaporating the solvent and weighing the residue, indicated that the values for Li, Mg, and Fe ion concentrations in the organic phase, as calculated from atomic absorption data, were accurate to within ±3%. The pH value of the aqueous solution was determined with a pH meter (Hanna pH 201) with deviation of ±0.02.

Figure 1. Variation in partition coefficient of Li with respect to TBP volume concentration (Li+, 0.055 mol/L; Fe3+, 0.1 mol/L; Cl−, 7 mol/ L).

the basis of the conservation of charge.26 As such, the extraction reaction equations in this system are proposed as follows: K′

FeCl3(A) + Cl− A ⇄ FeCl4(A)−

K′ =

3. RESULTS AND DISCUSSION 3.1. Extraction Behavior with TBP in Kerosene. The extraction behavior of Li at various TBP volume concentrations is shown in Figure 1. The partition coefficient (D = CO/CA, where CO is the equilibrium concentration of Li ion in organic phase and CA is the equilibrium concentration of Li ion in aqueous phase) of Li first increases and then decreases with increasing volume concentration of TBP in kerosene. TBP is a popular neutral organophosphorus extractant having high viscosity and density, which renders difficult the intermolecular interaction for TBP/Li and the phase separation of the extraction process. As such, kerosene is commonly used as an inert diluent for TBP. Kerosene is an inert diluent and has no interaction with either TBP or Li. The effect of TBP dilution by kerosene is reduced for TBP volume concentrations greater than 60% (Figure 1), and the partition coefficient of Li with TBP therefore decreases significantly. As noted above, to obtain the extraction properties of Li with TBP in kerosene, experimental data for a TBP volume concentration less than 60% were selected and the stoichiometry between TBP and Li was studied. The formation of LiFeCl4 from the combination of LiCl and FeCl3 in the extraction process has been confirmed on

(1)

[FeCl4 −]A [FeCl3]A [Cl−]A

(2) K ex

Li+ A + FeCl4(A)− + nTBPO XooY LiFeCl4 ·nTBPO Kex =

(3)

[LiFeCl4 ·nTBP]O [Li ]A [FeCl4 −]A [TBP]On +

(4)

where the aqueous and organic phases are denoted by the subscripts “A” and “O”, respectively. K′ = 102.5 is the dissociation constant for FeCl3.27 Kex is the apparent equilibrium constant. The stoichiometric coefficient between TBP and Li is denoted by n. The partition coefficient, D, is proposed as DLi =

[LiFeCl4 ·nTBP]O [Li+]A

(5)

Using eq 5, eq 4 can be simplified to Kex =

DLi [FeCl4 ]A [TBP]On −

(6)

and its logarithmic form is

Table 2. Physical Properties of Extractants and Diluents25 a

a

chemical

formula

av MW (g/mol)

ρ (g/cm3)

ε (F/m)

μ (D)

TBP DIBK acetophenone MIBK 2-heptanone kerosene

OP(O(CH2)3CH3)3 (CH3CH(CH3)CH2)2CO C6H5COCH3 CH3COCH2CH(CH3)2 CH3CO(CH2)4CH3 CH3(CH2)8−16CH3

266.32 142.25 120.14 100.16 114.19 142.17−254.30

0.980 0.810 1.030 0.796 0.820 0.800

8.34 (20 °C) 9.91 (20 °C) 17.44 (25 °C) 15.1 (20 °C) 11.95 (20 °C)

3.07 2.66 3.02 2.61

Density, ρ; dielectric constant, ε; dipole moment, μ. B

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log DLi = log Kex + log[FeCl−4 ]A + n log[TBP]O = log Kex + log K ′ + log[FeCl3]A + log[Cl−]A + n log[TBP]O (7)

Preliminary work indicated that the molar concentration of Cl− is much greater than that of Li+ and FeCl3, and almost all molar concentration of FeCl3 in the aqueous phase can be extracted into the organic phase. The values of log [FeCl3]A and log [Cl−]A remain constant with the changing of volume concentration of TBP. Thus, n can be calculated from eq 7 by regressing experimental data. The dependence of log DLi on log [TBP]O for three Li extraction experiments with TBP in kerosene is shown in Figure 2. For all three molar

Figure 3. Comparison of experimental and calculated data for lithium extraction with TBP in kerosene (Li+, 0.05 mol/L) (a, 0.05 mol/L Fe3+ and 8 mol/L Cl−; b, 0.09 mol/L Fe3+ and 8 mol/L Cl−; c, 0.05 mol/L Fe3+ and 7 mol/L Cl−; d, 0.075 mol/L Fe3+ and 7 mol/L Cl−).

in kerosene when the TBP volume concentration is less than 60%. 3.2. Extraction Behaviors with DIBK, Acetophenone, MIBK, and 2-Heptanone in Kerosene. It is known that the PO moiety on the TBP molecule is responsible for its effect as a ligand and extractant for metal ions. Interestingly, the C O moiety on the ketone molecule has a similar effect for metal ions. Variations in the Li partition coefficient with respect to the molar concentration of four ketones in kerosene are shown in Figure 4. For the molar concentrations of all four ketones, Figure 2. Dependence of log DLi on log [TBP]O for lithium extraction with TBP in kerosene (Fe3+, 0.1 mol/L; Cl−, 7 mol/L) (a, 0.049 mol/ L Li+; b, 0.052 mol/L Li+; c, 0.055 mol/L Li+).

concentrations of LiCl, the values derived for n are approximately 1. These results agree with results from our previously published work26 and confirm that the structural formula of the complex is LiFeCl4·TBP. On the basis of the results of the values of n, the values of Kex can be calculated using eq 7 and experimental data, as shown in Table 3. The value of log Kex is 5.57 ± 0.03. In cases where the Table 3. Apparent Equilibrium Constant of Extraction Reaction of Li with TBP in Kerosene molar concn of LiCl (mol/L)

log Kex

0.049 0.052 0.055

5.59 5.54 5.57

Figure 4. Variation in Li partition coefficient with respect to molar concentrations of four ketones (Li+, 0.05 mol/L; Fe3+, 0.1 mol/L; Cl−, 7 mol/L).

value of log Kex represents the thermodynamic property of extraction equilibrium, this log Kex may be used to predict the extraction equilibrium data of Li with TBP in kerosene when the volume concentration of TBP is less than 60%. A series of partition coefficients in our previously published work26 were calculated using the log Kex obtained in this work, and a comparison of the experimental and calculated data is shown in Figure 3. The calculated data fit the experimental data well, which indicates that the log Kex obtained in this work can be used to predict the extraction equilibrium data of Li with TBP

the partition coefficient ranges between 0 and 0.6, and is smaller than that of TBP in kerosene, since the binding capacities of the lone-pair electrons on CO are much weaker than those on PO. Similarly to TBP in kerosene, the extraction reaction equation for Li with ketones in kerosene can be proposed as follows: C

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between DLi and Kex′ in eq 9, the partition coefficients of Li with respect to the molar concentrations of three ketones with equal values of m (m = 2) in kerosene follow the sequence 2heptanone > MIBK > DIBK, as shown in Figure 4. Meanwhile, although the Kex′ of acetophenone is greater than those of 2heptanone and MIBK, the partition coefficient of Li with respect to the molar concentration of acetophenone is smaller than those of 2-heptanone and MIBK, since the value of m of acetophenone is 1. 3.3. Extraction Behaviors with TBP in DIBK, Acetophenone, MIBK, or 2-Heptanone. As noted above, kerosene is an inert diluent and has no interaction with either TBP or Li, while the four ketones are polar solvents and have a weak interaction force with Li. As such, we speculate that the greater partition coefficient of Li and the stronger effect of dilution than kerosene can be obtained using DIBK, acetophenone, MIBK, or 2-heptanone as diluents. A series of experimental trials was performed to confirm the hypothesis, and results are shown in Figure 6. The partition coefficients of Li with TBP in

K ex ′

Li+ A + FeCl4(A)− + mSO XoooY LiFeCl4 ·mSO

Kex′ =

(8)

DLi [FeCl4 −]A [S]Om

(9) −

log DLi = log Kex′ + log[FeCl4 ]A + m log[S]O

(10)

where “S” stands for ketones. Kex′ is the apparent equilibrium constant. The stoichiometric coefficient between the ketones and Li is denoted by m. Similar to TBP in kerosene, m can be calculated from eq 10 by regressing experimental data. The dependence of log DLi on log [S]O for Li extraction with four ketones in kerosene is shown in Figure 5. In trials of acetophenone and the other

Figure 5. Dependence of log DLi on log [S]O for lithium extraction with four ketones in kerosene (Li+, 0.05 mol/L; Fe3+, 0.1 mol/L; Cl−, 7 mol/L) (a, DIBK; b, acetophenone; c, MIBK; d, 2-heptanone).

three ketones (DIBK, MIBK, and 2-heptanone) in kerosene, the values derived for m are approximately 1 and 2, respectively. The results from MIBK in kerosene agree with the results of our previously published work26 and confirm that the structural formula of the complex is LiFeCl4·2MIBK. The structural complex formulas for the other three ketones are LiFeCl4·2DIBK, LiFeCl4·2(2-heptanone), and LiFeCl4·(acetophenone). The benzene ring moiety on the acetophenone molecule is responsible for its strong effects of steric hindrance on the structure of the complex formed with acetophenone, LiCl, and FeCl3, which render the formation of LiFeCl4·n(acetophenone) (n > 1) very difficult. Based on the values of m, Kex′ can be calculated using eq 9 and experimental data, as shown in Table 4. The values of Kex′ of the extraction reaction of Li with four ketones in kerosene follow the sequence acetophenone > 2-heptanone > MIBK > DIBK. Considering the values of Kex′ and the relationship

Figure 6. Comparison of partition coefficient of Li with respect to volume concentration of TBP in four ketones (Li+, 0.05 mol/L; Fe3+, 0.1 mol/L; Cl−, 7 mol/L).

all four ketones are greater than that of Li with TBP in kerosene, which confirms that polar solvents with weak interaction forces with Li can cause stronger effects of extraction and dilution than inert solvents. As shown in Table 2, both the dielectric constant and dipole moment of acetophenone are greater than those of the other three ketones, which indicates that the polarity of acetophenone is the strongest of the four ketones. As a stronger effect of dilution and polarity of extracting solvents can be obtained with a polar solvent than with kerosene, we conclude that using acetophenone as diluent for TBP yields the greatest Li partition coefficient. This result agrees with the results from the comparison of the Li partition coefficient with respect to volume concentration of TBP in four ketones, as shown in Figure 6. The greatest Li partition coefficient (4.08) can be obtained by 60% TBP/acetophenone. Generally speaking, polar solvents with no interaction with TBP, for example, ketones, not alcohols, can obtain not only larger Li partition coefficients, a strong dilution effect for TBP, and strong polarity and low density of the extracting solvents, but also promote phase separation and avoid the formation of a

Table 4. Apparent Equilibrium Constant of Extraction Reaction of Li with Four Ketones in Kerosene ketone

log Kex′

acetophenone 2-heptanone MIBK DIBK

3.32 2.91 2.83 2.64 D

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Lithium Zirconate Based Sorbents. Ind. Eng. Chem. Res. 2007, 46, 6696. (5) Bettge, M.; Seung, Y. R.; Maclaren, S.; Burdin, S.; Petrov, I.; Yu, M. F.; Sammann, E.; Abraham, D. P. Hierarchically Textured LixMn2‑yO4 Thin Films as Positive Electrodes for Lithium-Ion Batteries. J. Power Sources 2012, 206, 288. (6) Rahman, M. M.; Wang, J. Z.; Zeng, R.; Wexler, D.; Liu, H. K. LiFePO4-Fe2P-C Composite Cathode: An Environmentally Friendly Promising Electrode Material for Lithium-Ion Battery. J. Power Sources 2012, 206, 259. (7) Wang, X. L.; Li, J. L.; Zhang, M. J. Energetic Metal of the 21th Century: The Use of Metal Lithiun in Nuclear Fusion. J. Mater. Metall. 2001, 3, 249. (8) Zhang, J. C.; Wang, M.; Dai, J. Summarization of the Lithium Extraction System. J. Salt Lake Res. 2005, 13, 42. (9) Zhou, Z. Y.; Qin, W.; Fei, W. Y. Extraction Equilibria of Lithium with Tributyl Phosphate in Three Diluents. J. Chem. Eng. Data 2011, 56, 3518. (10) Liu, Y. H.; Deng, T. L. Progresses on the Process and Technique of Lithium Recovery from Salt Lake Brines Around the World. World Sci.-Technol. Res. Dev. 2006, 28, 69. (11) Wang, W. D.; Cao, Q. Production Process and Current Situation of Lithium Carbonate Extraction from Salt Lake Brine in China. J. Salt Lake Res. 2010, 18, 52. (12) Chitrakar, R.; Kanoh, H.; Miyai, Y.; Ooi, K. Recovery of Lithium from Seawater Using Manganese Oxide Adsorbent (H1.6Mn1.6O4) Derived from Li1.6Mn1.6O4. Ind. Eng. Chem. Res. 2001, 40, 2054. (13) Ozgur, C. Preparation and Characterization of LiMn2O4 IonSieve with High Li+ Adsorption Rate by Ultrasonic Spray Pyrolysis. Solid State Ionics 2010, 181, 1425. (14) Zhang, Q. H.; Sun, S. Y.; Li, S. P.; Jiang, H.; Yu, J. G. Adsorption of Lithium Ions on Novel Nanocrystal MnO2. Chem. Eng. Sci. 2007, 62, 4869. (15) Feng, Q.; Miyai, Y.; Kanoh, H.; Ooi, K. Li+ and Mg2+ Extraction and Li+ Insertion Reactions with LiMg0.5Mn1.5O4 Spinel in the Aqueous Phase. Chem. Mater. 1993, 5, 311. (16) Ma, P.; Chen, X. D.; Hossain, M. M. Lithium Extraction from a Multicomponent Mixture using Supported Liquid Membranes. Sep. Sci. Technol. 2000, 35, 2513. (17) Navarrete-Guijosa, A.; Navarrete-Casas, R.; ValenzuelaCalahorro, C.; López-González, J. D.; García-Rodríguez, A. Lithium Adsorption by Acid and Sodium Amberlite. J. Colloid Interface Sci. 2003, 264, 60. (18) Ma, P. H.; Deng, X. C.; Wen, X. M. Nano-Filtration Method for Separating Magnesium and Enriching Lithium from Salt Lake Brine. China Patent 1542147, 2004. (19) Huang, S. Q.; Cui, R. D.; Zhang, S. Z.; Bi, D. Z.; Sun, B. K.; Wang, G. L.; Du, Y. Q.; Li, L. J. Method of Extracting Anhydrous Lithium Chloride from Brine Containing Lithium. China Patent 87103431, 1987. (20) Chen, Z. Y.; Gu, W. L.; Chen, F. Z.; Xiao, N.; Qiu, S. Y.; Kan, S. R.; Xu, W. J. Study on Process of Solvent Extraction of Lithium from Bitterns Saturated with Magnesium Chloride. Chin. J. Rare Met. 1999, 23, 95. (21) Zhu, S. L; Piao, X. L.; Gou, Z. M. Extraction of Lithium from Brine with Neutral Organophosphorous Solvents. J. Tsinghua Univ. (Sci. Technol.) 2000, 40, 47. (22) Sun, X. L.; Chen, B. Z.; Xu, H.; Shi, X. C. Extraction of Lithium from Bittern. J. Cent. South Univ. (Sci. Technol.) 2007, 38, 262. (23) Zhou, Z. Y.; Qin, W.; Liu, Y.; Fei, W. Y. Extraction Equilibria of Lithium with Tributyl Phosphate in Kerosene and FeCl3. J. Chem. Eng. Data 2012, 57, 82. (24) Zhou, Z. Y.; Qin, W.; Liang, S. K.; Tan, Y. Z.; Fei, W. Y. Recovery of Lithium using Tributyl Phosphate in Methyl Isobutyl Ketone and FeCl3. Ind. Eng. Chem. Res. 2012, 51, 12926. (25) Dean, J. A. Lange’s Handbook of Chemistry, 15th ed.; McGrawHill: New York, 1999. (26) Zhou, Z. Y.; Qin, W.; Fei, W. Y.; Li, Y. G. A Study on Stoichiometry of Complexes of Tributyl Phosphate and Methyl

third phase. This is beneficial to industrial processes for Li extraction using TBP and FeCl3.

4. CONCLUSION In this work, the extraction equilibrium data of Li extracted by DIBK, acetophenone, MIBK, and 2-heptanone in kerosene for various molar concentrations of ketones and TBP in kerosene and these four ketones in various volume concentrations of TBP with FeCl3 as coextractant and MgCl2 as chloride source were studied. Results from TBP in kerosene indicate that the partition coefficient of Li decreases significantly when the volume concentration of TBP is greater than 60%, since the effect of dilution of kerosene on TBP is reduced sharply with increasing volume concentration of TBP. Thereafter, the stoichiometric coefficient between TBP and Li and the apparent equilibrium constant of the extraction reaction equation for TBP in kerosene were obtained. Both the stoichiometric coefficients and calculated partition coefficients obtained using the apparent equilibrium constant agree with results from our previously published work.26 The binding capacities of the lone-pair electrons on CO are much weaker than those on PO. The stoichiometric coefficients between these four ketones and Li were obtained, for which the value for MIBK and Li agrees with results from our previous published work.26 The apparent equilibrium constants of the extraction reaction equation were obtained and could be used to predict trends in extraction with these four ketones in kerosene. Greater partition coefficients could be obtained by using DIBK, acetophenone, MIBK, or 2-heptanone to replace kerosene. This indicates that polar solvents with weak interaction forces with Li can cause a stronger effect on extraction and dilution than inert solvents as diluents for TBP. Polar solvents with no interaction with TBP are recommended for industrial processes for Li extraction with TBP and FeCl3.

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AUTHOR INFORMATION

Corresponding Author

*Fax: +86 10 62782748. Tel.: +86 10 62782748. E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS This work was supported by the National High Technology Research and Development Program of China (2008AA06Z111), the QingHai Key Technology R&D Program (2011-J-154), and the China Postdoctoral Science Foundation (2012M520294).

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