Effects of piperacillin synthesis on the interfacial tensions and droplet sizes

doi:10.1016/j.cjche.2021.05.025

中国化学工程学报 ›› 2021, Vol. 38 ›› Issue (10): 53-62.DOI: 10.1016/j.cjche.2021.05.025

• Fluid Dynamics and Transport Phenomena • 上一篇下一篇

Effects of piperacillin synthesis on the interfacial tensions and droplet sizes

Yu Xie¹, Guoming Huang², Weiguo Hu², Yujun Wang¹

1. The State Key Laboratory of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China;
2. North China Pharmaceutical Group Co., Ltd., Shijiazhuang 052165, China

收稿日期:2020-12-14 修回日期:2021-03-24 出版日期:2021-10-28 发布日期:2021-12-02
通讯作者: Yujun Wang
基金资助:
This work was financially supported by the National Key Research and Development Program of China (2019YFA0905100), the National Natural Science Foundation of China (21878169 and 21991102), and Tsinghua University Initiative Scientific Research Program (2018Z05JZY010).

Effects of piperacillin synthesis on the interfacial tensions and droplet sizes

Yu Xie¹, Guoming Huang², Weiguo Hu², Yujun Wang¹

1. The State Key Laboratory of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China;
2. North China Pharmaceutical Group Co., Ltd., Shijiazhuang 052165, China

Received:2020-12-14 Revised:2021-03-24 Online:2021-10-28 Published:2021-12-02
Contact: Yujun Wang
Supported by:
This work was financially supported by the National Key Research and Development Program of China (2019YFA0905100), the National Natural Science Foundation of China (21878169 and 21991102), and Tsinghua University Initiative Scientific Research Program (2018Z05JZY010).

摘要/Abstract

摘要： Piperacillin is a polar organic substance, and can reduce the interfacial tension of oil and water when dissolved in water. In this study, changes in dichloromethane-water interfacial tensions and microdroplet sizes during piperacillin synthesis from an aqueous solution of ampicillin and dichloromethane solution of 4-ethyl-2,3-dioxo-1-piperazine carbonyl chloride (EDPC) were observed using a pendent drop technique and a coaxial ring tube system with embedded high-speed camera, respectively. It was found that the rapid N-acylation reaction caused the piperacillin at the interface to synthesize rapidly and diffuse out slowly, resulting in the interfacial tension decreased from 19.5 mN·m^-1 to 7.2 mN·m^-1 rapidly and then increased slowly as the concentrations of ampicillin and EDPC were 0.05 mol·L^-1 and 0.1 mol·L^-1. Meanwhile, the increase in the concentration of EDPC increased the peak concentration of piperacillin at the interface, and the addition of ethyl acetate to the ampicillin solution promoted mass transfer and reduced the aggregation of piperacillin effectively. During synthesis, the interfacial tension decreased, leading to a change in droplet sizes in the micro-reaction system. The two-phase reaction was carried out in a coaxial ring tube, with ampicillin and EDPC solutions as continuous and dispersed phases, respectively. The reaction reduced the dripping flow area, and the addition of ethyl acetate to the ampicillin solution slightly affected the division of the flow pattern. Under the same flow conditions, the droplet sizes of the reaction group were smaller than those of the no reaction group. The experimental results demonstrated that the increase of the continuous phase, decrease in the dispersed phase flow rate, or increase in EDPC concentration making droplet sizes smaller, and the addition of ethyl acetate slightly affected droplet sizes. These findings are important for the design and optimization of piperacillin synthesis reactors.

关键词: Pendant drop, Interfacial tension, Microchannel, Droplet size, Piperacillin synthesis, Mass transfer

Abstract: Piperacillin is a polar organic substance, and can reduce the interfacial tension of oil and water when dissolved in water. In this study, changes in dichloromethane-water interfacial tensions and microdroplet sizes during piperacillin synthesis from an aqueous solution of ampicillin and dichloromethane solution of 4-ethyl-2,3-dioxo-1-piperazine carbonyl chloride (EDPC) were observed using a pendent drop technique and a coaxial ring tube system with embedded high-speed camera, respectively. It was found that the rapid N-acylation reaction caused the piperacillin at the interface to synthesize rapidly and diffuse out slowly, resulting in the interfacial tension decreased from 19.5 mN·m^-1 to 7.2 mN·m^-1 rapidly and then increased slowly as the concentrations of ampicillin and EDPC were 0.05 mol·L^-1 and 0.1 mol·L^-1. Meanwhile, the increase in the concentration of EDPC increased the peak concentration of piperacillin at the interface, and the addition of ethyl acetate to the ampicillin solution promoted mass transfer and reduced the aggregation of piperacillin effectively. During synthesis, the interfacial tension decreased, leading to a change in droplet sizes in the micro-reaction system. The two-phase reaction was carried out in a coaxial ring tube, with ampicillin and EDPC solutions as continuous and dispersed phases, respectively. The reaction reduced the dripping flow area, and the addition of ethyl acetate to the ampicillin solution slightly affected the division of the flow pattern. Under the same flow conditions, the droplet sizes of the reaction group were smaller than those of the no reaction group. The experimental results demonstrated that the increase of the continuous phase, decrease in the dispersed phase flow rate, or increase in EDPC concentration making droplet sizes smaller, and the addition of ethyl acetate slightly affected droplet sizes. These findings are important for the design and optimization of piperacillin synthesis reactors.

Key words: Pendant drop, Interfacial tension, Microchannel, Droplet size, Piperacillin synthesis, Mass transfer

Yu Xie, Guoming Huang, Weiguo Hu, Yujun Wang. Effects of piperacillin synthesis on the interfacial tensions and droplet sizes[J]. 中国化学工程学报, 2021, 38(10): 53-62.

Yu Xie, Guoming Huang, Weiguo Hu, Yujun Wang. Effects of piperacillin synthesis on the interfacial tensions and droplet sizes[J]. Chinese Journal of Chemical Engineering, 2021, 38(10): 53-62.

参考文献

[1] R. Gao, R. Hao, D. Liu, L. Wang, J. Zhu, L. Zuo, Z. Yan, H. Liu, S. Wei, Preparing piperacillin acid involves adding ampicillin in water in reactor to prepare buffer solution, and then mixing dioxo piperzine carbonyl chloride and alkaline modifier, China Pat. CN104910178 (2015).
[2] Y. Xie, G.M. Huang, Y.J. Wang, Z.R. Yan, X. Wang, J. Huang, M.T. Gao, W.Y. Fei, G.S. Luo, Synthesis of piperacillin with low impurity content using a new three-feed membrane dispersion microreactor, Chem. Eng. J. 387 (2020) 124178
[3] S. Kancharla, N.A. Zoyhofski, L. Bufalini, B.F. Chatelais, P. Alexandridis, Association between nonionic amphiphilic polymer and ionic surfactant in aqueous solutions: Effect of polymer hydrophobicity and micellization, Polymers (Basel) 12 (8) (2020) E1831
[4] R.S. Kawai, M. Niki, S. Yada, T. Yoshimura, Physicochemical and solution properties of quaternary-ammonium-salt-type amphiphilic gemini ionic liquids with spacers containing oxygen or nitrogen, Colloids Surf. A: Physicochem. Eng. Aspects 603 (2020) 125218
[5] A.K. Sood, M. Aggarwal, Mixed micellar and interfacial studies of triblock copolymers with amphiphilic drug ibuprofen in aqueous urea solutions, J. Surfactants Deterg. 22 (6) (2019) 1409-1418
[6] Y. Yang, M.E. Leser, A.A. Sher, D.J. McClements, Formation and stability of emulsions using a natural small molecule surfactant: Quillaja saponin (Q-Naturale^®), Food Hydrocoll. 30 (2) (2013) 589-596
[7] Y.B. Vysotsky, E.S. Kartashynska, D. Vollhardt, Theoretical description of 2D-cluster formation of nonionic surfactants at the air/water interface, Colloid Polym. Sci. 293 (11) (2015) 3065-3089
[8] N.R. Tummala, L. Shi, A. Striolo, Molecular dynamics simulations of surfactants at the silica-water interface: Anionic vs nonionic headgroups, J. Colloid Interface Sci. 362 (1) (2011) 135-143
[9] D.L. Wang, Y.M. Li, B. Chen, L. Zhang, Novel surfactants as green corrosion inhibitors for mild steel in 15% HCl: Experimental and theoretical studies, Chem. Eng. J. 402 (2020) 126219
[10] G.Z. Li, J.H. Mu, Y. Li, S.L. Yuan, An experimental study on alkaline/surfactant/polymer flooding systems using nature mixed carboxylate, Colloids Surf. A: Physicochem. Eng. Aspects 173 (1-3) (2000) 219-229
[11] J.E. Shaw, P.R. Stapp, Sodium carboxylates for producing low interfacial tensions between hydrocarbons and water, J. Colloid Interface Sci. 107 (1) (1985) 231-236
[12] P.P. Shah, D.J. Briedis, H.G. Robson, J.P. Conterato, In vitro activity of piperacillin compared with that of carbenicillin, ticarcillin, ampicillin, cephalothin, and cefamandole against Pseudomonas aeruginosa and Enterobacteriaceae, Antimicrob. Agents Chemother. 15 (3) (1979) 346-350
[13] K. Machka, H. Dickert, I. Braveny, In vitro activity of piperacillin compared with that of ampicillin, ticarcillin, azlocillin, and mezlocillin, Arzneimittel-Forschung 30 (2) (1980) 304-307
[14] I. Nowrouzi, A.K. Manshad, A.H. Mohammadi, Effects of dissolved carbon dioxide and ions in water on the dynamic interfacial tension of water and oil in the process of carbonated smart water injection into oil reservoirs, Fuel 243 (2019) 569-578
[15] M.H. Rausch, P.S. Schmidt, T.R. Gall, C. Giraudet, A.P. Fröba, Wetting behavior and interfacial tension of a refrigerant oil in air and refrigerant atmospheres, Int. J. Refrig. 107 (2019) 225-233
[16] Y. Song, Y. Tian, Y. Xiao, X. Ren, R. Qiao, Interfacial tensions of binary liquid-liquid systems, J. Chem. Ind. Eng. (China) 50 (5) (1999) 620-628
[17] X.F. Li, Z.R. Chen, H.H. Pan, D.X. Liu, H.R. Li, S.J. Han, Determination of dynamic interfacial tension by computer-aided pendant drop digitization—Effect of surfactant concentration on dit, J. Chem. Ind. Eng. China 52 (6) (2001) 545-548
[18] Y.H. Mori, Dynamic interfacial tension in water/n-pentane system: An experimental study using the oscillating-jet method, Chem. Eng. Sci. 143 (2016) 130-138
[19] J.H. Li, L.F. Yang, X.F. Ding, J. Chen, Y.J. Wang, G.S. Luo, H.M. Yu, Visual study of mass transfer characterization in the process of biological catalytic hydration of acrylonitrile using pendant drop method, RSC Adv. 5 (96) (2015) 79164-79171
[20] E. Teston, V. Hingot, V. Faugeras, C. Errico, M. Bezagu, M. Tanter, O. Couture, A versatile and robust microfluidic device for capillary-sized simple or multiple emulsions production, Biomed. Microdevices 20 (4) (2018) 1-12
[21] X.H. Lin, F.B. Bao, C.X. Tu, Z.Q. Yin, X.Y. Gao, J.Z. Lin, Dynamics of bubble formation in highly viscous liquid in co-flowing microfluidic device, Microfluid. Nanofluid. 23 (5) (2019) 1-9
[22] Y. Chen, Y. Cui, K. Wang, G. Luo, Droplet and bubble dispersion in step T-junction microchannel, CIESC J. 71 (2020) 265-273
[23] L.T. Li, J.S. Zhang, K. Wang, J.H. Xu, G.S. Luo, Droplet formation of H₂SO₄ /alkane system in a T-junction microchannel: Gravity effect, AIChE J. 62 (12) (2016) 4564-4573
[24] J.H. Xu, S.W. Li, W.J. Lan, G.S. Luo, Microfluidic approach for rapid interfacial tension measurement, Langmuir 24 (19) (2008) 11287-11292
[25] M.L. Brusseau, S. van Glubt, The influence of surfactant and solution composition on PFAS adsorption at fluid-fluid interfaces, Water Res. 161 (2019) 17-26
[26] C. Cramer, P. Fischer, E.J. Windhab, Drop formation in a co-flowing ambient fluid, Chem. Eng. Sci. 59 (15) (2004) 3045-3058
[27] C.F. Zhou, P.T. Yue, J.J. Feng, Formation of simple and compound drops in microfluidic devices, Phys. Fluids 18 (9) (2006) 092105

Effects of piperacillin synthesis on the interfacial tensions and droplet sizes

Effects of piperacillin synthesis on the interfacial tensions and droplet sizes

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