Effect of β-cyclodextrin on anti-interference performance of Triton X-114 ultraviolet spectrum

doi:10.16085/j.issn.1000-6613.2021-0748

Abstract

Abstract:

The interaction between octyl phenyl polyoxyethylene ether (Triton X-114) and fatty alcohol polyoxyethylene ether (AEO-9) could significantly affect the ultraviolet spectrum of Triton X-114 in aqueous solution. The experimental results indicated that the maximum absorption wavelength of Triton X-114 was 223nm in the range of 200—350nm, and the ultraviolet absorbance of AEO-9 was close to 0. In aqueous solution, AEO-9 can decrease the UV absorbance of Triton X-114 by 3.4%. AEO-9 also significantly decreased the apparent critical micelle concentration (cmc) of Triton X-114 from 0.219mmol/L to 0.207mmol/L and 0.202mmol/L, respectively when the concentration of AEO-9 increased from 0 to 0.050mmol/L and 0.100mmol/L. Experimental results further showed that β-cyclodextrin (β-CD) can effectively reduce the AEO-9 on the ultraviolet absorbance of the Triton X-114 and the influence of apparent cmc. When the Triton X-114 and AEO-9 distribution in aqueous solution with the amount of substance ratio 1∶1 to join the β-CD, the recovery of Triton X-114 in the mixed aqueous solution changed from 95.8%—103.3% to 99.0%—100.1%. It was suggested that the β-CD can significantly reduce the interference of AEO-9 on Triton X-114. The results of Fourier transform infrared spectroscopy analysis (FTIR), nuclearmagnetic resonance hydrogen spectrum (¹H NMR) analysis and thermogravimetric-differential thermal analysis (TG-DSC) showed that Triton X-114 entered β-CD molecular cavity and formed inclusion, which was the main reason for blocking the formation of mixed micelles of Triton X-114 molecule and eliminating the interference of AEO-9 to Triton X-114.

Key words: Triton X-114, β-CD, micelle, UV spectra

摘要：

辛基苯基聚氧乙烯醚（曲拉通X-114）和脂肪醇聚氧乙烯醚（AEO-9）之间的相互作用能对水溶液中曲拉通X-114的紫外光谱产生明显影响。实验结果表明，在200～350nm范围内，曲拉通X-114的最大吸收波长为223nm，AEO-9的紫外吸光度接近于0；在水溶液中，AEO-9能减弱曲拉通X-114的紫外吸光度，降幅达3.4%；AEO-9还能显著降低曲拉通X-114的表观临界胶束浓度（cmc），当AEO-9的浓度从0增加到0.050mmol/L 和0.100mmol/L时，曲拉通X-114的表观cmc从0.219mmol/L分别降至0.207mmol/L和0.202mmol/L。实验结果进一步表明，β-环糊精（β-CD）能有效降低AEO-9对曲拉通X-114的紫外吸光度及表观cmc的影响，在曲拉通 X-114和AEO-9复配水溶液中，按物质的量比1∶1加入β-CD，复配水溶液中曲拉通X-114的回收率从95.8%～103.3%变化至99.0%～100.1%，表明了β-CD能明显降低AEO-9对曲拉通X-114的干扰作用。红外光谱表征结果（FTIR）、核磁共振氢谱表征（¹H NMR）及热重差热分析表征结果（TG-DSC）表明，曲拉通X-114进入β-CD 分子空腔并形成包结物，是阻断曲拉通X-114分子形成混合胶束以及消除AEO对曲拉通X-114的干扰的主要原因。

关键词: 辛基苯基聚氧乙烯醚, β-环糊精, 胶束, 紫外光谱

CLC Number:

O625.151

XU Huihua, SHI Dongpo, WU Hao, YIN Xianqing, ZHENG Yancheng, CHEN Wu, LI Geng. Effect of β-cyclodextrin on anti-interference performance of Triton X-114 ultraviolet spectrum[J]. Chemical Industry and Engineering Progress, 2022, 41(4): 2075-2081.

许慧华, 石东坡, 吴浩, 尹先清, 郑延成, 陈武, 李赓. β-环糊精对曲拉通X-114紫外光谱抗干扰性能的影响[J]. 化工进展, 2022, 41(4): 2075-2081.

Figures/Tables 14

References 15

1	ZHAI Wenqi, MA Guiyang, HU Zhiyong. Effect of organic alkali, n-alkanol, and nonionic surfactant ternary compound system on viscosity reduction of viscous crude oil[J]. Petroleum Science and Technology, 2019, 37(9): 989-996.
2	WU Hsinyi, SHIH Chialung, LEE Ton, et al. Development and validation of an analytical procedure for quantitation of surfactants in dishwashing detergents using ultra-performance liquid chromatography-mass spectrometry[J]. Talanta, 2019, 194: 778-785.
3	盛旭光, 梅勇, 聂梦涵, 等. 表面活性剂辅助微萃取-高效液相色谱法测定尿中一氯苯的2种代谢物[J]. 理化检验(化学分册), 2020, 56(5): 519-524.
	SHENG Guangxu, MEI Yong, NIE Menghan, et al. HPLC determination of 2 metabolites of monochlorobenzene in urine with surfactant assisted microextraction[J]. Physical Testing and Chemical Analysis Part B (Chemical Analysis), 2020, 56(5): 519-524.
4	黄斌, 张威, 王捷,等. 驱油剂对三元复合驱含油污水中油滴稳定性的影响[J]. 化工进展, 2019, 38(2): 1053-1061.
	HUANG Bin, ZHANG Wei, WANG Jie, et al. Effect of oil displacement agent on oil droplet stability in alkali/surfactant/ polymer flooding oily wastewater[J]. Chemical Industry and Engineering Progress, 2019, 38(2): 1053-1061.
5	STRECK L, DORO P N D M, FERNANDES-PEDROSA M F, et al. High performance liquid chromatography-diode array detector method for benznidazole quantitation in lipid based and self assembling cyclodextrins drug delivery systems[J]. Journal of Analytical Chemistry, 2020, 75(7): 922-929.
6	MA Qiang, ZHANG Yun, ZHAI Junfeng, et al. Characterization and analysis of non-ionic surfactants by supercritical fluid chromatography combined with ion mobility spectrometry-mass spectrometry[J]. Analytical and Bioanalytical Chemistry, 2019, 411(13): 2759-2765.
7	ZHANG Rui, LIU Yang, HUANG Xinran, et al. Interaction of a digestive protease, Candida rugosa lipase, with three surfactants investigated by spectroscopy, molecular docking and enzyme activity assay[J]. Science of the Total Environment, 2018, 622/623: 306-315.
8	SCHOLZ N, BEHNKE T, RESCH-GENGER U. Determination of the critical micelle concentration of neutral and ionic surfactants with fluorometry, conductometry, and surface tension — A method comparison[J]. Journal of Fluorescence, 2018, 28(1): 465-476.
9	NABI A, JESUDASON C G, LEE V S, et al. Study of interaction between cationic surfactant (CTAB) and paracetamol by electrical conductivity, tensiometric and spectroscopic methods[J]. Journal of Molecular Liquids, 2018, 256: 100-107.
10	MOHAMMED-SAEID W, KAROYO AH, VERRALL RE, et al. Inclusion complexes of melphalan with gemini-conjugated β-cyclodextrin: physicochemical properties and chemotherapeutic efficacy in in-vitro tumor models[J]. Pharmaceutics, 2019, 11(9): 427.
11	ZHONG Xing, HU Caixia, YAN Xiaowei, et al. Aggregate morphology transition of an adamantane-containing surfactant via the host-guest interaction with β-cyclodextrin[J]. Journal of Molecular Liquids, 2018, 272: 209-217.
12	MIRHASHEMI F, AMROLLAHI M A. Host/guest inclusion system of surfactants with β-cyclodextrin as a viable catalyst for one-pot synthesis of mono- and bis(indolyl) methylmalononitriles in H₂O[J]. Turkish Journal of Chemistry. 2018, 42(4): 988-996.
13	MEIRA L H R, SOARES G A B, BONOMINI H I M, et al. Thermodynamic compatibility between cyclodextrin supramolecular complexes and surfactant[J]. International Journal of Pharmaceutics, 2018, 544(1): 203-212.
14	石东坡, 黄弘毅, 尹先清, 等. HP-β-CD消除SDS对SLDED紫外光谱的干扰[J]. 光谱学与光谱分析, 2019, 39(6): 1812-1816.
	SHI Dongpo, HUANG Hongyi, YIN Xianqing, et al. Interference of SDS on ultraviolet absorbance spectrum of SLDED greatly reduced by HP-β-CD[J]. Spectroscopy and Spectral Analysis, 2019, 39(6): 1812-1816.
15	XU Zifu, GUAN Jin, SHAO Huili, et al. Combined use of Cu(Ⅱ)-L-histidine complex and β-cyclodextrin for the enantioseparation of three amino acids by CE and a study of the synergistic effect[J]. Journal of Chromatographic Science, 2020, 58(10): 969-975.

曲拉通X-114 /mmol?L^-1	AEO-9 /mmol?L^-1	β-CD /mmol?L^-1	测量值 /mmol?L^-1	回收率 /%
0.100	0.050	0	0.099^a	99.0
0.180	0.050	0	0.186^a	103.3
0.200	0.100	0	0.203^a	101.5
0.240	0.100	0	0.230^a	95.8
0.100	0.050	0.100	0.099^b	99.0
0.180	0.050	0.180	0.181^b	100.1
0.200	0.100	0.200	0.199^b	99.5
0.240	0.100	0.240	0.238^b	99.2
0.200	0.100	0.200	0.199^c	99.5
0.200	0.100	0.200	0.199^d	99.5

曲拉通X-114 /mmol?L^-1	AEO-9 /mmol?L^-1	β-CD /mmol?L^-1	测量值 /mmol?L^-1	回收率 /%
0.100	0.050	0	0.099^a	99.0
0.180	0.050	0	0.186^a	103.3
0.200	0.100	0	0.203^a	101.5
0.240	0.100	0	0.230^a	95.8
0.100	0.050	0.100	0.099^b	99.0
0.180	0.050	0.180	0.181^b	100.1
0.200	0.100	0.200	0.199^b	99.5
0.240	0.100	0.240	0.238^b	99.2
0.200	0.100	0.200	0.199^c	99.5
0.200	0.100	0.200	0.199^d	99.5

样品	1H	2H	3H	4H	5H	6H
β-CD	5.052	3.581	3.948	3.567	3.639	3.859
包结物	5.034	3.611	3.878	3.590	3.682	3.845

样品	1H	2H	3H	4H	5H	6H
β-CD	5.052	3.581	3.948	3.567	3.639	3.859
包结物	5.034	3.611	3.878	3.590	3.682	3.845

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