pH开关聚醚型非离子表面活性剂及其去除土壤中菲的潜在应用

doi:10.3969/j.issn.2097-2806.2025.11.003

Abstract

Abstract:

To achieve the recovery and recycling of eluent from soil washing enhanced by nonionic surfactants, a polyether-type nonionic surfactant C8-DIB-PEG₁₀ with a reversible pH-responsive switch was designed and synthesized. Taking an artificial sample of phenanthrene-contaminated soil as an example, and using the micellar solution of this surfactant as the washing agent, the removal effect on phenanthrene （Phe） in soil, the post-treatment of eluent, and the recovery and recycling of C8-DIB-PEG₁₀ were investigated. The results showed that the critical micelle concentration of C8-DIB-PEG₁₀ at 25 ℃ was approximately 1.01×10^-3 mol/L; when pH was adjusted to 3.0 with HCl, C8-DIB-PEG₁₀ lost its surface activity due to the breaking of imine bond, forming PEG₁₀-CHO and octylamine hydrochloride, both of which had good water solubility. When pH was adjusted to 10.0 with NaOH, C8-DIB-PEG₁₀ could be formed again. The removal rate of Phe in soil could reach 99.9%. After C8-DIB-PEG₁₀was switched to non-surface-active by using HCl, PEG₁₀-CHO and octylamine hydrochloride could be recycled in the aqueous phase. The recovery rate of C8-DIB-PEG₁₀ could reach 96.5%. Over three more cycles of use, no significant abnormal change was observed either in the removal rate of Phe or the recovery rate of C8-DIB-PEG₁₀.

Key words: pH-switchable nonionic surfactant, surfactant-enhanced soil washing, phenanthrene, recycling of surfactants

CLC Number:

TQ423

Lei Dong, Huanjin Zou, Xuefeng Liu. Synthesis of pH-switchable nonionic polyether surfactant and its potential application in removing phenanthrene from soil[J].China Surfactant Detergent & Cosmetics, 2025, 55(11): 1388-1394.

Figures/Tables 7

Fig. 1

Fig. 2

Fig. 3

Fig. 4

Fig. 5

Fig. 6

Fig. 7

References 24

[1]	Sakshi , Singh S K, Haritash A K. Polycyclic aromatic hydrocarbons: Soil pollution and remediation[J]. International Journal of Environmental Science and Technology, 2019, 16 (10) : 6489-6512. doi: 10.1007/s13762-019-02414-3
[2]	Zhang P, Chen Y. Polycyclic aromatic hydrocarbons contamination in surface soil of China: A review[J]. Science of the Total Environment, 2017, 605: 1011-1020.
[3]	Achten C, Andersson J T. Overview of polycyclic aromatic compounds (PAC)[J]. Polycyclic Aromatic Compounds, 2015, 35: 177-186. pmid: 26823644
[4]	Wilcke W. Global patterns of polycyclic aromatic hydrocarbons (PAHs) in soil[J]. Geoderma, 2007, 141 (3) : 157-166. doi: 10.1016/j.geoderma.2007.07.007
[5]	Broman D, Näuf C, Lundbergh I, et al. An in situ study on the distribution, biotransformation and flux of polycyclic aromatic hydrocarbons (PAHs) in an aquatic food chain (seston-Mytilus edulis L.-Somateria mollissima L.) from the baltic: An ecotoxicological perspective[J]. Environmental Toxicology and Chemistry, 1990, 9 (4) : 429-442.
[6]	Phillips D H. Fifty years of benzo(a)pyrene[J]. Nature, 1983, 303: 468-472. doi: 10.1038/303468a0
[7]	Ahn C K, Woo S H, Park J M. Surface solubilization of phenanthrene by surfactant sorbed on soils with different organic matter contents[J]. Journal of Hazardous Materials, 2010, 177: 799-806. doi: 10.1016/j.jhazmat.2009.12.104 pmid: 20096994
[8]	Liu J W, Wei K H, Xu S W, et al. Surfactant-enhanced remediation of oil-contaminated soil and groundwater: A review[J]. Science of the Total Environment, 2021, 756: 144142. doi: 10.1016/j.scitotenv.2020.144142
[9]	Wang S Y, Cai S, Liu X F, et al. Reversible CO₂/N₂-tuning Krafft temperature of sodium alkyl sulphonates and a proof-of-concept usage in surfactant-enhanced soil washing[J]. Chemical Engineering Journal, 2021, 417: 129316. doi: 10.1016/j.cej.2021.129316
[10]	Trellu C, Pechaud N, Oturan E, et al. Remediation of soils contaminated by hydrophobic organic compounds: how to recover extracting agents from soil washing solutions?[J] Journal of Hazardous Materials, 2021, 404: 124137. doi: 10.1016/j.jhazmat.2020.124137
[11]	Zeng Y, Zhang M, Lin D, et al. Selective removal of phenanthrene from SDBS or TX100 solution by sorption of resin SP850[J]. Chemical Engineering Journal, 2020, 388: 124191. doi: 10.1016/j.cej.2020.124191
[12]	Bai X X, Wang Y, Zheng X, et al. Remediation of phenanthrene contaminated soil by coupling soil washing with Tween 80, oxidation using the UV/S₂O₈^2- process and recycling of the surfactant[J]. Chemical Engineering Journal, 2019, 369: 1014-1023. doi: 10.1016/j.cej.2019.03.116
[13]	Pan J, Sun L, Liu X, et al. Precipitation-Dissolution switchable surfactants with the potential of simultaneous retrieving of surfactants and hydrophobic organic contaminants from emulsified and micellar eluents[J]. Chemical Engineering Journal, 2023, 458: 141297. doi: 10.1016/j.cej.2023.141297
[14]	Liu X Y, Liu X F, Sun L L, et al. Recyclable dynamic imine-based nonionic surfactants and potential use in post-processing of eluted emulsions[J]. Journal of Surfactants and Detergents, 2023, 26: 807-815. doi: 10.1002/jsde.v26.6
[15]	Liu Y X, Jessop P G, Cunningham M, et al. Switchable surfactants[J]. Science, 2006, 313: 958-960. pmid: 16917059
[16]	Cheng M, Zeng G, Huang D, et al. Advantages and challenges of Tween 80 surfactant-enhanced technologies for the remediation of soils contaminated with hydrophobic organic compounds[J]. Chemical Engineering Journal, 2017, 314: 98-113. doi: 10.1016/j.cej.2016.12.135
[17]	Takahashi Y, Koizumi N, Kondo Y. Active demulsification of photoresponsive emulsions using cationic-anionic surfactant mixtures[J]. Langmuir, 2016, 32 (3) : 683-688. doi: 10.1021/acs.langmuir.5b03912 pmid: 26731043
[18]	Wijnja H, Pignatello J J, Malekani K. Formation of π-π complexes between phenanthrene and model π-acceptor humic subunits[J]. Journal of Environmental Quality, 2004, 33 (1) : 265-275. pmid: 14964381
[19]	Li J, Nowak P, Otto S. Dynamic combinatorial libraries: From exploring molecular recognition to systems chemistry[J]. Journal of the American Chemical Society, 2013, 135 (25) : 9222-9239. doi: 10.1021/ja402586c pmid: 23731408
[20]	Chen J, Hu X Y, Fang Y, et al. What dominates the interfacial properties of extended surfactants: Amphipathicity or surfactant shape?[J]. Journal of Colloid and Interface Science, 2019, 547: 190-198. doi: S0021-9797(19)30416-3 pmid: 30954763
[21]	Wang G T, Wu G L, Wang Z Q, et al. Asymmetric and symmetric bolaform supra-amphiphiles: Formation of imine bond influenced by aggregation[J]. Langmuir, 2014, 30 (6) : 1531-1535. doi: 10.1021/la405000a pmid: 24460208
[22]	Li H, Liu X. Rational design of dynamic imine surfactants for oil-water emulsions: Learning from oil-induced reversible dynamic imine bond formation[J]. Journal of Colloid and Interface Science, 2022, 607: 163-170. doi: 10.1016/j.jcis.2021.08.178
[23]	Ren G H, Wang L, Chen Q Q, et al. pH switchable emulsions based on dynamic covalent surfactants[J]. Langmuir, 2017, 33 (12) : 3040-3046. doi: 10.1021/acs.langmuir.6b04546 pmid: 28282144
[24]	Lin Y, Wang A, Qiao Y, et al. Rationally designed helical nanofibers via multiple non-covalent interactions: fabrication and modulation[J]. Soft Matter, 2010, 6 (9) : 2031-2036. doi: 10.1039/b926642a

Synthesis of pH-switchable nonionic polyether surfactant and its potential application in removing phenanthrene from soil

RichHTML

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 7

References 24

Related Articles 15

Metrics

Comments

Recommended 10

[1]	Jingru Wang,Xiangji Meng,Yangzhen Zheng,Lifei Zhi,Xiaoming Li,Guoyong Wang,Yan Wang. Research progress in applications of silicone quaternary ammonium surfactants [J]. China Surfactant Detergent & Cosmetics, 2025, 55(11): 1468-1475.
[2]	Xiuhua Yan,Lanqin Tang. Synthesis and properties of phosphobetaine-modified ZnO [J]. China Surfactant Detergent & Cosmetics, 2025, 55(11): 1402-1407.
[3]	Yu Yao,Huanjin Zou,Xuefeng Liu. Reversible pH response of disodium monotetradecyl phosphate and how to recover it from solutions or emulsions [J]. China Surfactant Detergent & Cosmetics, 2025, 55(10): 1245-1251.
[4]	Yushi Sun,Zhao Chen,Zhenggang Cui,Xiaomei Pei,Binglei Song. Non-aqueous Pickering emulsions synergistically stabilized by double tailed surfactants and silica nanoparticles [J]. China Surfactant Detergent & Cosmetics, 2025, 55(10): 1252-1259.
[5]	Bo Sun,Xiaochun Liu,Baowen Lv,Hui Liu,Zhenxing Li,Yongli Yan. Effects of special surfactants on the foaming performance of organic foams [J]. China Surfactant Detergent & Cosmetics, 2025, 55(10): 1268-1274.
[6]	Guoqiang Lu, Meng Mu, Ye Fan, Xuefeng Liu, Yongmin Zhang. Study on the synthesis and properties of sulfate-spacered gemini surfactants [J]. China Surfactant Detergent & Cosmetics, 2025, 55(9): 1085-1092.
[7]	Yibo Li, Min Yang, Qinghuan Deng, Shuoshi Wang. Study on the mechanism of in-situ viscosity reduction and wettability control in oil displacement by diluted-microemulsion [J]. China Surfactant Detergent & Cosmetics, 2025, 55(9): 1093-1099.
[8]	Chao Tang, Jiaojiao Guan, Shouping Zhang, Wenliang Cai, Yulian Lin, Shuixiang Xie, Yunfei Xiang. Effects of asphaltene, resin, and petroleum acid on the phase transition and interfacial properties of emulsions [J]. China Surfactant Detergent & Cosmetics, 2025, 55(9): 1129-1136.
[9]	Mei Chen, Yaoyao Wu, Dandan Xia, Xiaowei Chang, Guizhen Su, Chen Liu. Foam and mildness study of trehalolipid surfactant in rinse off formulations [J]. China Surfactant Detergent & Cosmetics, 2025, 55(9): 1153-1162.
[10]	Xuyuan Zhang, Yingfeng Li, Shengti Cao, Chunxin Gao, Yueqing Huo, Xiaochen Liu. Application of alkyl diphenyl ethers/alkyl benzene mixed sulfonates in industrial cleaning [J]. China Surfactant Detergent & Cosmetics, 2025, 55(9): 1163-1168.
[11]	Yutong Liu, Bingbing Yuan, Tiantian Han, Gong Chen, Yonghang Mu, Linhua Song, Zi Wang. Interaction mechanism and application of the aqueous mixtures of surfactants and proteins [J]. China Surfactant Detergent & Cosmetics, 2025, 55(9): 1198-1206.
[12]	Zhecheng Wang, Zhihui Zheng, Minjia Yuan. Study on the foam properties of mixed systems based on sodium lauroyl glutamate [J]. China Surfactant Detergent & Cosmetics, 2025, 55(8): 1035-1041.
[13]	Qi Sun, Zhengrong Zhao, Zhicheng Xu, Lei Zhang, Lu Zhang. Effects of extended anionic surfactants on the wettability of polytetrafluoroethylene interface [J]. China Surfactant Detergent & Cosmetics, 2025, 55(8): 949-960.
[14]	Yanping Chu, Feng Gao, Weihua Zhang, Lei Zhang, Lu Zhang. Study on interfacial dilational rheology of surfactant flooding with low-interfacial-tension surfactants [J]. China Surfactant Detergent & Cosmetics, 2025, 55(8): 961-968.
[15]	Juan Zhang, Ping Liu, Xiaokang Hou, Yuan Gao, Qichao Lv, Zihao Yang. Study on the phase behavior and influencing factors for the emulsions of crude oil/petroleum sulfonate under reservoir conditions [J]. China Surfactant Detergent & Cosmetics, 2025, 55(8): 969-979.