Synthesis and Properties of Carboxylate Gemini Surfactants

doi:10.11944/j.issn.1000-0518.2020.03.190242

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (3): 271-279.DOI: 10.11944/j.issn.1000-0518.2020.03.190242

• Full Papers • Previous Articles Next Articles

Synthesis and Properties of Carboxylate Gemini Surfactants

ZHANG Chenglu(),SONG Fulu,ZHOU Long,HAN Zhen,BAI Ru,YANG Fan,WANG Nan,SUN Yuedong

College of Chemistry and Chemical Engineering, Liaoning Normal University,Dalian,Liaoning 116029,China

Received:2019-09-10 Accepted:2019-12-05 Published:2020-03-01 Online:2020-03-10
Contact: ZHANG Chenglu
Supported by:
Supported by the Science and Technology Project of Liaoning Education Department(No.2009A426)

Abstract

Abstract:

To screen environmental friendly new gemini surfactants, five carboxylate-type gemini surfactants EODPN1-EODPN 5 [2,2'-(1,2-CH₂CH₂-di-O-)-di-(4-C_nH₂_n₊₁COPhCOONa), n=5, 7, 9, 11 and 13] were synthesized from salicylic acid. The structures of the target products were confirmed by nuclear magnetic resonance (NMR) spectroscopy and Fourier transform infrared (FT-IR) spectrometer. The properties of EODPN as surfactants were explored, and the relevant thermodynamic parameters were obtained by theoretical calculation using the Gibbs surface adsorption equation. The results show that EODPN has excellent surface activities, extremely low critical micelle concentration (CMC) values (minimum 0.4 mmol/L), good surface tension reduction performance (minimum 29.74 mN/m) and high surface adsorption per unit area Γ(up to 3.37×10^-6 mol/m²). By changing the length of the hydrophobic alkyl carbon chain, the surface activity and self-assembly ability of EODPN were optimized, and EODPN4 was selected as the best surfactant. Based on EODPN4 which can be stably combined with copper ions, the detection of surfactant content is realized.

Key words: gemini surfactant, carboxylate, thermodynamic parameters, surface activity

ZHANG Chenglu, SONG Fulu, ZHOU Long, HAN Zhen, BAI Ru, YANG Fan, WANG Nan, SUN Yuedong. Synthesis and Properties of Carboxylate Gemini Surfactants[J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 271-279.

References

[1]	Shamsi S A,Akbay C,Warner I M,et al. Polymeric Anionic Surfactant for Electrokinetic Chromatography:Separation of 16 Priority Polycyclic Aromatic Hydrocarbon Pollutants[J]. Anal Chem,1998,70(14):3078-3083.
[2]	LIU Jiajia,XIE Yicheng,XU Hujun,et al. Synthesis and Properties of a Cationic Gemini Asphalt Emulsifier[J]. Chinese J Appl Chem,2018,35(5):552-558(in Chinese). 刘佳佳,谢益诚,许虎君,等. 一种阳离子Gemini型沥青乳化剂的合成及性能[J]. 应用化学,2018,35(5):552-558.
[3]	Ngimhuang J,Furukawa J,Satoh T,et al. Synthesis of a Novel Polymeric Surfactant by Reductive N-Alkylation of Chitosan with 3-O-Dodecyl-D-glucose[J]. Polymer,2004,45(3):837-841.
[4]	Gao C L,Whitcombe M J,Vulfson E N.Enzymatic Synthesis of Dimeric and Trimeric Sugar-Fatty Acid Esters[J]. Enzyme Microb Technol,1999,25(3/5):264-270.
[5]	Kumar R S,Arunachalam S. Synthesis, Micellar Properties, DNA Binding and Antimicrobial Studies of Some Surfactant-Cobalt(Ⅲ) Complexes[J]. Biophys Chem,2008,136(2/3):136-144.
[6]	Yu D,Wang Y,Zhang J,et al. Effects of Calcium Ions on Solubility and Aggregation Behavior of an Anionic Sulfonate Gemini Surfactant in Aqueous Solutions[J]. J Colloid Interface Sci,2012,381(1):83-88.
[7]	Sakai K,Umezawa S,Tamura M,et al. Adsorption and Micellization Behavior of Novel Gluconamide-Type Gemini Surfactants[J]. J Colloid Interface Sci,2008,318(2):440-448.
[8]	Fitzgerald P A,Carr M W,Davey T W,et al. Preparation and Dilute Solution Properties of Model Gemini Nonionic Surfactants[J]. J Colloid Interface Sci,2004,275(2):649-658.
[9]	Huang X,Han Y C,Wang Y X.Aggregation Properties of Cationic Gemini Surfactants with Dihydroxyethylamino Headgroups in Aqueous Solution[J]. Colloid Surf A,2008,325(1/2):26-32.
[10]	Li R Q,Wei L B,Hu C C,et al. Aggregation Properties of a Novel Class of Amphiphilic Cationic Polyelectrolytes Containing Gemini Surfactant Segments[J]. J Phys Chem B,2010,114(39):12448-12454.
[11]	Asefi D,Mahmoodi N M,Arami M.Effect of Nonionic Co-Surfactants on Corrosion Inhibition Effect of Cationic Gemini Surfactant[J]. Colloid Surf A,2010,355(1/3):183-186.
[12]	Hellberg P E,Bergström K,Holmberg K.Cleavable Surfactants[J]. J Surfactants Deterg,2000,3(1):81-91.
[13]	Ding M M,Li J H,Fu X T,et al. Synthesis, Degradation, and Cytotoxicity of Multiblock Poly(ε-caprolactone urethane)s Containing Gemini Quaternary Ammonium Cationic Groups[J]. Biomacromolecules,2009,10(10):2857-2865.
[14]	Tehrani-Bagha A R, Oskarsson H, Van Ginkel C G. Cationic Ester-Containing Gemini Surfactants: Chemical Hydrolysis and Biodegradation[J]. J Colloid Interface Sci,2007,312(2):444-452.
[15]	Li H B,Wang X Q.Single Quantum Dot-Micelles Coated with Gemini Surfactant for Selective Recognition of a Cation and an Anion in Aqueous Solutions[J]. Sens Actuators B-Chem,2008,134(1):238-244.
[16]	Bagha A R T,Bahrami H,Movassagh B,et al. Interactions of Gemini Cationic Surfactants with Anionic Azo Dyes and Their Inhibited Effects on Dyeability of Cotton Fabric[J]. Dyes Pigm,2007,72(3):331-338.
[17]	Chen F Y,Liu M S,Du J,et al. Preparation and Properties of Novel Asymmetric Gemini Alkyl olyglycosides[J]. Tenside Surfactants Deterg,2015,27(6):455-458.
[18]	Quagliotto P,Montoneri E,Tambone F,et al. Chemicals from Wastes: Compost-Derived Humic Acid-Like Matter as Surfactant[J]. Environ Sci Technol,2006,40(5):1686-1692.
[19]	Acharya D P,Gutiérrez J M,Aramaki K,et al. Interfacial Properties and Foam Stability Effect of Novel Gemini-Type Surfactants in Aqueous Solutions[J]. J Colloid Interface Sci,2005,291(1):236-243.
[20]	Liu J Y,Zhao J X,He Y J.Aggregation of Carboxylate Gemini Surfactant with P-Oxybenzene Spacer in Aqueous Solution Studied by Intrinsic Probe Spectroscopy[J]. Colloid Surf A,2007,304(1/3):25-30.
[21]	Renouf P,Hebrault D,Desmurs J R,et al. Synthesis and Surface-Active Properties of a Series of New Anionic Gemini Compounds[J]. Chem Phys Lipids,1999,99(1):21-32.
[22]	Jiang R,Huang Y X,Zhao J X,et al. Aqueous Two-Phase System of an Anionic Gemini Surfactant and a Eationic Conventional Surfactant Mixture[J]. Fluid Phase Equilib,2009,277(2):114-120.
[23]	Jiang R,Zhao J X,Ma Y H.Dynamic Adsorption of Opposite-Charged Gemini Surfactant Mixture at Air/Water Interface[J]. Colloid Surf A,2006,289(1/3):233-236.
[24]	Gautam A,Kambo N,Upadhyay S K,et al. Anionic Gemini Surfactant Viz. Sodium Salt of Bis(1-dodecenylsuccinamic acid); Synthesis, Surface Properties and Micellar Effect on Oxidation of Reducing Sugars by Hexacyanoferrate(III)[J]. Colloid Surf A,2008,312(2/3):195-202.
[25]	Ibrahim Y A,Elwahy A H M. Efficient Synthesis of a Rang of Benzo-Substituted Macrocyclic Diamides[J]. Synthesis,1993,5(5):503-508.
[26]	Wu X,Dai C,Fang S,et al. The Effect of Hydroxyl on the Solution Behavior of a Quaternary Ammonium Gemini Surfactant[J]. Phys Chem Chem Phys,2017,19(24):16047-16056.
[27]	LIU Haiyan,GU Daming,LIU Guoyu,et al. Synthesis and Surface Properties of Novel Gemini Imidazole Surfactants[J]. Chem J Chinese Univ,2013,34(2):401-407(in Chinese). 刘海燕,顾大明,刘国宇,等. 新型Gemini咪唑表面活性剂的合成及表面性能[J]. 高等学校化学学报,2013,34(2):401-407.
[28]	Yuan F,Wang T T,Hu H M,et al. Two luminescent d10, Metal Coordination Polymers Assembled from a Semirigid Terpyridyl Carboxylate Ligand with High Selective Detecting of Cu2+, Cr2$O_{7}^{2-}$, and Acetone[J]. J Solid State Chem,2017,251(4):79-89.
[29]	Liu C,Tang B,Zhang S,et al. Photoinduced Electron Transfer Mediated by Coordination Between Carboxyl on Carbon Nanodots and Cu2+ Quenching Photoluminescence[J]. J Phys Chem C,2018,122(6):3662-3668.
[30]	Brunner J,Kraemer R.Copper(II)-Quenched Oligonucleotide Probes for Fluorescent DNA Sensing[J]. J Am Chem Soc,2004,126(42):13626-13627.

Synthesis and Properties of Carboxylate Gemini Surfactants

RichHTML

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	YANG Wei-Guang, CAO Yu-Peng, JU Hong-Bin, WANG Ya-Kui, GENG Tao, JIANG Ya-Jie. Synthesis and Properties of Oleamide Quaternary Ammonium Gemini Surfactant [J]. Chinese Journal of Applied Chemistry, 2021, 38(2): 220-227.
[2]	TANG Jing, LIN Xiaoyi, ZHOU Wenyan, HUANG Qiuying. Synthesis, Crystal Structure and Recognition Properties of One-Dimensional Luminescent Cd Coordination Polymer [J]. Chinese Journal of Applied Chemistry, 2019, 36(4): 459-464.
[3]	WANG Qiang,ZHAO Xinping. Synthesis of Functionalized 2-Hydroxyisophthalate via the Cascade Reactions of Allenic Ketones with Acetonedicarboxylate [J]. Chinese Journal of Applied Chemistry, 2018, 35(6): 645-651.
[4]	LIU Jiajia, XIE Yicheng, XU Hujun. Synthesis and Properties of a Cationic Gemini Asphalt Emulsifier [J]. Chinese Journal of Applied Chemistry, 2018, 35(5): 552-558.
[5]	Hao MA, Chunyan LIAO, Meilin FAN, Xue'en LIU, Junjiang TENG, Ning LI. Dissolution of Cellulose in Carboxylate-Based Task-Specific Ionic Liquids [J]. Chinese Journal of Applied Chemistry, 2018, 35(4): 449-456.
[6]	LIN Xiaoyi, ZHU Yongchao, MENG Xiangru. Synthesis, Crystal Structure and Luminescent Properties of a Europium Complex from Imidazole Dicarboxylate [J]. Chinese Journal of Applied Chemistry, 2018, 35(1): 82-88.
[7]	CHAI Yongzhen, CHANG Yu, SONG Ruiqin, LIU Wei, LI Yunhui, PAN Lihua. Synthesis and Characterization of Dimethyl 6,6'-Dimethyl-[2,2'-bipyridine]-4,4'-dicarboxylate [J]. Chinese Journal of Applied Chemistry, 2017, 34(2): 146-150.
[8]	BI Haoyu, LIANG Yaqin, LI Yan. Adsorption of p-Cresol on X-Type Gemini Surfactant-modified Hydrotalcite-like Nanocomposite [J]. Chinese Journal of Applied Chemistry, 2017, 34(11): 1329-1335.
[9]	LI Liangui, FU Zhipeng, LI Mingchao, ZHANG Qiang, WANG Rui, WANG Guoqiang, JIANG Min. Synthesis and Characterization of Polyethylene Terephthalate-b-poly(ethylene 2,5-furandicarboxylate) Block Polyester [J]. Chinese Journal of Applied Chemistry, 2017, 34(1): 54-59.
[10]	ZHANG Fan, WANG Lulu, WANG Jilin, FENG Ruijiang, ZHANG Yang. Gemini-type Cationic Molecules-Styrene Block Polymer Anion Conducting Membrane Prepared by in-situ Polymerization [J]. Chinese Journal of Applied Chemistry, 2016, 33(6): 693-700.
[11]	ZHANG Xiuqin, CHAO Xuqiang, CHEN Qiang, SUN Xiaoqiang. Synthesis of Diisopropyl Azodicarboxylate [J]. Chinese Journal of Applied Chemistry, 2015, 32(3): 261-266.
[12]	ZHONG Guiyun. Synthesis of Anionic Organotin Carboxylate by the Reaction of Ph₃SnCl with o-Phthalic Acid under Organic Amines and Its Bactericidal Activity [J]. Chinese Journal of Applied Chemistry, 2015, 32(3): 299-303.
[13]	ZHANG Zhijian1*, KUANG Daizhi2, ZHANG Fuxing2, YU Jiangxi2, JIANG Wujiu2. Synthesis, Crystal Structure and Biological Activities of the Tris (2-methyl-2-phenyl) propyl Tin Trichloroacetic Acid Ester [J]. Chinese Journal of Applied Chemistry, 2014, 31(09): 1058-1062.
[14]	HUANG Hongmei1,2, XIAO Yi1,2, YANG Xiya1, BIAN Wenhuan1, YIN Dulin1,2, MAO Liqiu1,2. Ionic Liquid-mediated Catalytic Oxidation of Isoeugenol to Vanillin via* Oxovanadium 1,3,5-Benzenetricarboxylate [J]. Chinese Journal of Applied Chemistry, 2014, 31(08): 952-957.
[15]	LV Shasha, WEI Jing, JIANG Feng, WANG Sui*. Adsorption-decolorization of Four Ionic Dyes by Carboxylated Graphene [J]. Chinese Journal of Applied Chemistry, 2013, 30(10): 1215-1221.