Synergistic solvent extraction of boric acid by trioctylamine and 2-hydroxydodecanoic acid

doi:10.1016/j.cjche.2024.06.009

中国化学工程学报 ›› 2024, Vol. 74 ›› Issue (10): 117-126.DOI: 10.1016/j.cjche.2024.06.009

• Full Length Article • 上一篇下一篇

Synergistic solvent extraction of boric acid by trioctylamine and 2-hydroxydodecanoic acid

Zhuojun Jiang¹, Yufeng Liang², Shuyao Xiong³, Guo Li⁴, Qian Zhang¹, Benzheng Xia¹, Liangrong Yang¹, Zheng Li^1,5

1 CAS Key Laboratory of Green Process and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China;
2 School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China;
3 Univ. Lille, CNRS, Centrale Lille Institut, Univ. Artois, UMR 8181-UCCS-Unité de Catalyse et Chimie du Solide, Lille F-59000, France;
4 MCC Ruimu New Energy Technology Co., Ltd, Tangshan 063200, China;
5 School of Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100408, China

收稿日期:2024-04-26 修回日期:2024-06-21 接受日期:2024-06-25 出版日期:2024-10-28 发布日期:2024-07-16
通讯作者: Zheng Li,E-mail:zli@ipe.ac.cn
基金资助:
The study was supported by the National Natural Science Foundation of China (22278407, 21922814, 22138012, 22178349), CAS Project for Young Scientists in Basic Research (YSBR-038), National Key Research and Development Program of China (2021YFC2901500, 2022YFC2105302), and Shandong Energy Institute (SEI U202306).

Synergistic solvent extraction of boric acid by trioctylamine and 2-hydroxydodecanoic acid

Zhuojun Jiang¹, Yufeng Liang², Shuyao Xiong³, Guo Li⁴, Qian Zhang¹, Benzheng Xia¹, Liangrong Yang¹, Zheng Li^1,5

1 CAS Key Laboratory of Green Process and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China;
2 School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China;
3 Univ. Lille, CNRS, Centrale Lille Institut, Univ. Artois, UMR 8181-UCCS-Unité de Catalyse et Chimie du Solide, Lille F-59000, France;
4 MCC Ruimu New Energy Technology Co., Ltd, Tangshan 063200, China;
5 School of Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100408, China

Received:2024-04-26 Revised:2024-06-21 Accepted:2024-06-25 Online:2024-10-28 Published:2024-07-16
Contact: Zheng Li,E-mail:zli@ipe.ac.cn
Supported by:
The study was supported by the National Natural Science Foundation of China (22278407, 21922814, 22138012, 22178349), CAS Project for Young Scientists in Basic Research (YSBR-038), National Key Research and Development Program of China (2021YFC2901500, 2022YFC2105302), and Shandong Energy Institute (SEI U202306).

摘要/Abstract

摘要： A synergistic solvent extraction system comprising trioctylamine (TOA) and ligands with hydroxyl and carboxyl groups can efficiently recover boric acid (H₃BO₃) and separate boron isotopes. However, the structure of ligands might impact H₃BO₃ extraction, boron isotope separation, and solvent loss, which has not been thoroughly investigated. This study initially evaluated the influence of ligand's type, pK_a, and substituents on H₃BO₃ extraction efficiency, as well as the impact of the B₍₄₎-O structure (boron is bound to four oxygen atoms) in the organic phase on isotope separation efficiency. Subsequently, by synthesizing the highly hydrophobic 2-hydroxydodecanoic acid (HYA), the extraction performance and mechanism of the TOA/HYA system were investigated. The findings highlight the superior extraction efficiency when employing di-phenolic hydroxyl, phenolic hydroxyl + carbinol hydroxyl, and alcoholic hydroxyl + carboxyl ligands compared to phenolic hydroxyl + carboxyl, phenolic hydroxyl + ethanol hydroxyl, diol hydroxyl, and dicarboxylic ligands. The organic phase anion complex, exclusively comprising the B₍₄₎-O structure, enhances isotope separation effectiveness. The TOA/HYA system achieves an 80% single-stage extraction efficiency for H₃BO₃. H₃BO₃ and HYA are extracted into the organic phase at a ratio of 1:2, with the anion complex solely containing the B₍₄₎-O structure. This study paves the way for the construction of novel boric acid extraction and boron isotope separation systems.

关键词: Boric acid, 2-Hydroxydodecanoic acid, Synergistic extraction, Coordination mechanism, Boron isotope separation

Abstract: A synergistic solvent extraction system comprising trioctylamine (TOA) and ligands with hydroxyl and carboxyl groups can efficiently recover boric acid (H₃BO₃) and separate boron isotopes. However, the structure of ligands might impact H₃BO₃ extraction, boron isotope separation, and solvent loss, which has not been thoroughly investigated. This study initially evaluated the influence of ligand's type, pK_a, and substituents on H₃BO₃ extraction efficiency, as well as the impact of the B₍₄₎-O structure (boron is bound to four oxygen atoms) in the organic phase on isotope separation efficiency. Subsequently, by synthesizing the highly hydrophobic 2-hydroxydodecanoic acid (HYA), the extraction performance and mechanism of the TOA/HYA system were investigated. The findings highlight the superior extraction efficiency when employing di-phenolic hydroxyl, phenolic hydroxyl + carbinol hydroxyl, and alcoholic hydroxyl + carboxyl ligands compared to phenolic hydroxyl + carboxyl, phenolic hydroxyl + ethanol hydroxyl, diol hydroxyl, and dicarboxylic ligands. The organic phase anion complex, exclusively comprising the B₍₄₎-O structure, enhances isotope separation effectiveness. The TOA/HYA system achieves an 80% single-stage extraction efficiency for H₃BO₃. H₃BO₃ and HYA are extracted into the organic phase at a ratio of 1:2, with the anion complex solely containing the B₍₄₎-O structure. This study paves the way for the construction of novel boric acid extraction and boron isotope separation systems.

Key words: Boric acid, 2-Hydroxydodecanoic acid, Synergistic extraction, Coordination mechanism, Boron isotope separation

Zhuojun Jiang, Yufeng Liang, Shuyao Xiong, Guo Li, Qian Zhang, Benzheng Xia, Liangrong Yang, Zheng Li. Synergistic solvent extraction of boric acid by trioctylamine and 2-hydroxydodecanoic acid[J]. 中国化学工程学报, 2024, 74(10): 117-126.

参考文献

[1] Z.M. Guan, J.F. Lv, P. Bai, X.H. Guo, Boron removal from aqueous solutions by adsorption-A review, Desalination 383 (2016) 29-37.
[2] K.C. Kim, N.I. Kim, T. Jiang, J.C. Kim, C.I. Kang, Boron recovery from salt lake brine, seawater, and wastewater-A review, Hydrometallurgy 218 (2023) 106062.
[3] A.F. Kiemde, J. Marin, V. Flexer, A. Chagnes, Boron extraction by aliphatic mono- and di-hydroxy alcohols from a representative continental brine, Hydrometallurgy 225 (2024) 106280.
[4] Q.L. Luo, M.Z. Dong, C. Bai, H.N. Liu, Z.J. Wu, X. Du, J. Li, X.L. Huang, Green synthesis of polyol functionalized cotton linter polymer adsorbents by the hydrothermal method: Effects of the structure of the ligands for boron anionic species capture, Chem. Eng. Sci. 285 (2024) 119574.
[5] Z.Y. Xu, H. Su, J. Zhang, W.S. Liu, Z.W. Zhu, J.G. Wang, J. Chen, T. Qi, Recovery of boron from brines with high magnesium content by solvent extraction using aliphatic alcohol, RSC Adv. 11 (26) (2021) 16096-16105.
[6] J.Y. Lin, N.N.N. Mahasti, Y.H. Huang, Recent advances in adsorption and coagulation for boron removal from wastewater: A comprehensive review, J. Hazard. Mater. 407 (2021) 124401.
[7] S. Kurklu-Kocaoglu, A. Guvensoy-Morkoyun, C. Yildirim, S. Velioglu, M.G. Ahunbay, S.B. Tantekin-Ersolmaz, Affinity-based engineering of carbon nanotube embedded polyamide membranes for simultaneous desalination and boron removal, J. Membr. Sci. 699 (2024) 122636.
[8] Q.P. Zhao, L.Y. Ee, D.L. Zhao, C.M. Chang, T.S. Chung, S.B. Chen, Thin-film nanocomposite membranes with polyol-functionalized layered double hydroxides for boron removal via reverse osmosis, J. Membr. Sci. 695 (2024) 122497.
[9] C.X. Lin, D.L. Gao, Y.F. Guo, S.Q. Wang, T.L. Deng, Boron recovery from the liquid mineral resources, Adv. Mater. Res. 549 (2012) 349-352.
[10] T.P. Belova, L.S. Ershova, Boron concentration by industrial anion exchanger resins from model solutions in a dynamic mode, Heliyon 7 (2) (2021) e06141.
[11] X.D. Guan, P. Li, J.K. Zhang, Q.Q. Chang, J.C. Xiong, Y.W. Han, H.L. Zhang, Q. Li, L.L. Zhang, X.Y. Cao, H.J. Wang, Y.M. Yang, H.J. Xie, S.L. Zheng, Selective separation and recovery of boron from spent Nd-Fe-B magnets leaching solution, Sep. Purif. Technol. 344 (2024) 127115.
[12] J. Guo, Y. Yang, X.Y. Gao, J.G. Yu, Boron extraction from lithium-rich brine using mixed alcohols, Hydrometallurgy 197 (2020) 105477.
[13] A. Chagnes, Advances in hydrometallurgy, Metals 9 (2) (2019) 211.
[14] R. Zhang, Y.M. Xie, J.F. Song, L.X. Xing, D.F. Kong, X.M. Li, T. He, Extraction of boron from salt lake brine using 2-ethylhexanol, Hydrometallurgy 160 (2016) 129-136.
[15] A. Kenan Poslu, W.L. Dudeney, Solvent extraction of boron with 2-ethyl-1,3-hexanediol and 2-chloro-4-(1,1,3,3-tetramethylbutyl)-6-methylolphenol in petroleum ether, kerosene and chloroform solutions, Hydrometallurgy 10 (1) (1983) 47-60.
[16] X.W. Peng, D. Shi, Y.Z. Zhang, L.C. Zhang, L.M. Ji, L.J. Li, Recovery of boron from unacidified salt lake brine by solvent extraction with 2,2,4-trimethyl-1,3-pentanediol, J. Mol. Liq. 326 (2021) 115301.
[17] X.W. Peng, L.J. Li, D. Shi, L.C. Zhang, H.F. Li, F. Nie, F.G. Song, Recovery of boric acid from salt lake brines by solvent extraction with 2-butyl-1-n-octanol, Hydrometallurgy 177 (2018) 161-167.
[18] Y. Miyazaki, H. Matsuo, T. Fujimori, H. Takemura, S. Matsuoka, T. Okobira, K. Uezu, K. Yoshimura, Interaction of boric acid with salicyl derivatives as an anchor group of boron-selective adsorbents, Polyhedron 27 (13) (2008) 2785-2790.
[19] R. Pizer, P.J. Ricatto, Thermodynamics of several 1: 1 and 1: 2 complexation reactions of the borate ion with bidentate ligands. ¹¹B NMR spectroscopic Studies1, Inorg. Chem. 33 (11) (1994) 2402-2406.
[20] K. Kustin, R. Pizer, Temperature-jump study of the rate and mechanism of the boric acid-tartaric acid complexation, J. Am. Chem. Soc. 91 (2) (1969) 317-322.
[21] R. Pizer, L. Babcock, Mechanism of the complexation of boron acids with catechol and substituted catechols, Inorg. Chem. 16 (7) (1977) 1677-1681.
[22] M. Pasdeloup, C. Brisson, NMR study of the complexation of boric acid with catechol (1,2-dihydroxybenzene), Org. Magn. Reson. 16 (2) (1981) 164-167.
[23] K. Morita, N. Hirayama, K. Morita, H. Imura, Effect of organic cations and solvents on the ion-pair extraction of boric acid with salicyl alcohol, Solvent Extr. Res. Dev. Jpn. 18 (2011) 199-203.
[24] Z.J. Jiang, Z.D. Zhang, B.Z. Xia, S.Y. Xiong, L.R. Yang, Z. Li, Mechanism of boric acid extraction by trioctylamine and tartaric acid, Sep. Purif. Technol. 331 (2024) 125597.
[25] A.V. Khoroshilov, P.I. Ivanov, Separation of boron isotopes by chemical exchange in liquid-liquid systems, J. Phys.: Conf. Ser. 1099 (2018) 012006.
[26] P.I. Ivanov, A.V. Khoroshilov, Separating boron isotopes by means of chemical exchange with boronic acid, Russ. J. Phys. Chem. A 96 (2) (2022) 407-411.
[27] A.V. Khoroshilov, P.I. Ivanov, Boron isotope separation by extraction method: Features of the phase composition and flow reflux, J. Phys.: Conf. Ser. 2147 (1) (2022) 012018.
[28] L. Cui, X. Yang, J.F. Wang, H.Y. He, Y.X. Guo, F.Q. Cheng, S.J. Zhang, Theoretical prediction of 6Li/7Li separation in solvent extraction system using Urey model, Chem. Eng. J. 358 (2019) 435-445.
[29] G.M.P. E. M. Kuznetsova, R. S. Filippova, and V. F. Malakhov, New method of separation of boron isotopes, Zh. Fiz. Khim. 34 (1960) 2370.
[30] N. Bachelier, J.F. Verchere, Formation of neutral complexes of boric acid with 1,3-diols in organic solvents and in aqueous solution, Polyhedron 14 (13-14) (1995) 2009-2017.
[31] J.B. Bialecki, F.U. Axe, A.B. Attygalle, Hydroxycarbonyl anion (m/z 45), a diagnostic marker for alpha-hydroxy carboxylic acids, J. Mass Spectrom. 44 (2) (2009) 252-259.
[32] L. Settimo, K. Bellman, R.M.A. Knegtel, Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds, Pharm. Res. 31 (4) (2014) 1082-1095.
[33] Q. Yang, Y. Li, J.D. Yang, Y.D. Liu, L. Zhang, S.Z. Luo, J.P. Cheng, Holistic prediction of the pKa in diverse solvents based on a machine-learning approach, Angew. Chem. Int. Ed. 59 (43) (2020) 19282-19291.
[34] M.A. Martinez-Aguirre, R. Villamil-Ramos, J.A. Guerrero-Alvarez, A.K. Yatsimirsky, Substituent effects and pH profiles for stability constants of arylboronic acid diol esters, J. Org. Chem. 78 (10) (2013) 4674-4684.
[35] X.P. Xing, X. Shi, W.Y. Wang, J.N. Ye, Determination of pKa values of salicyl alcohol and phenol by capillary electrophoresis with amperometric detection, J. Capill. Electrophor. Microchip Technol. 10 (5-6) (2008) 81-85.
[36] F. Wernig, E. Boles, M. Oreb, De novo biosynthesis of 8-hydroxyoctanoic acid via a medium-chain length specific fatty acid synthase and cytochrome P450 in Saccharomyces cerevisiae, Metab. Eng. Commun. 10 (2020) e00111.
[37] W. Johnson Jr, W.F. Bergfeld, D.V. Belsito, R.A. Hill, C.D. Klaassen, D. Liebler, J.G. Marks Jr, R.C. Shank, T.J. Slaga, P.W. Snyder, F.A. Andersen, Safety assessment of 1,2-glycols as used in cosmetics, Int. J. Toxicol. 31 (5 Suppl) (2012) 147S-168S.
[38] R.H. Betts, J. Bron, A discussion of partial isotope separation by means of solvent extraction, Sep. Sci. 12 (6) (1977) 635-639.
[39] H.C. Urey, The thermodynamic properties of isotopic substances, J. Chem. Soc. (1947) 562-581.
[40] https://pubchem.ncbi.nlm.nih.gov/.
[41] A. Gossi, W. Riedl, B. Schuur, Mass transfer analysis and kinetic modeling for process design of countercurrent membrane supported reactive extraction of carboxylic acids, Chem. Eng. Sci. X 13 (2022) 100119.
[42] R.S. Juang, R.H. Huang, Comparison of extraction equilibria of succinic and tartaric acids from aqueous solutions with tri-n-octylamine, Ind. Eng. Chem. Res. 35 (6) (1996) 1944-1950.
[43] K. Schmeide, K. Fritsch, H. Lippold, Cherkouk formerly Geissler, M. Bader, Joint project: Retention of radionuclides relevant for final disposal in natural clay rock and saline systems - Subproject 2: Geochemical behavior and transport of radionuclides in saline systems in the presence of repository-relevant organics, 2016.
[44] N. Tahara, M. Kakiage, I. Yanase, H. Kobayashi, Effect of addition of tartaric acid on synthesis of boron carbide powder from condensed boric acid-glycerin product, J. Alloys Compd. 573 (2013) 58-64.
[45] M. Maseda, Y. Miyazaki, T. Takamuku, Thermodynamics for complex formation of boric acid and borate with hydroxy acids and diols, J. Mol. Liq. 341 (2021) 117343.

Synergistic solvent extraction of boric acid by trioctylamine and 2-hydroxydodecanoic acid

Synergistic solvent extraction of boric acid by trioctylamine and 2-hydroxydodecanoic acid

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 4

编辑推荐

Metrics

本文评价

[1]	吕建华, 刘继东, 孙玉洁, 李春利. Kinetics of Forward Extraction of Boric Acid from Salt Lake Brine by 2-Ethyl-1,3-hexanediol in Toluene Using Single Drop Technique[J]. Chinese Journal of Chemical Engineering, 2014, 22(5): 496-502.
[2]	张文娟, 李铁虎, 卢萌, 侯翠岭. Comparative Study of the Modification of Coal Tar Pitch for Higher Carbonization Yield and Better Properties[J]. Chinese Journal of Chemical Engineering, 2013, 21(12): 1391-1396.
[3]	邓彤, 黄丽娟, 傅丽. 从硫酸盐溶液中协同萃取镓[J]. , 2002, 10(1): 112-115.
[4]	李洲, 秦峰, 鲍浩, 谷雪蔷, 戴玲妹. 大环内酯类抗生素的中性络合萃取和协同萃取[J]. , 2000, 8(4): 304-309.