Citation: Wei-Guang YANG, Yu-Peng CAO, Hong-Bin JU, Ya-Kui WANG, Tao GENG, Ya-Jie JIANG. Synthesis and Properties of Oleamide Quaternary Ammonium Gemini Surfactant[J]. Chinese Journal of Applied Chemistry, ;2021, 38(2): 220-227. doi: 10.19894/j.issn.1000-0518.200241 shu

Synthesis and Properties of Oleamide Quaternary Ammonium Gemini Surfactant

China Research Institute of Daily Chemical Industry Co., Ltd, Taiyuan 030001, China

Corresponding author: Ya-Jie JIANG, jiangyajie2004@163.com
Received Date: 12 August 2020
Accepted Date: 15 October 2020

Fund Project: the National Key Research and Development Project of China 2017YFB0308900the Project of JALA Research Funds JALA 2018

Figures(6)

Oleamide quaternary ammonium Gemini surfactants GS-1, GS-2, GS-3 were synthesized by the reaction of Oleamide propyl dimethylamine and 1, 3-dichloro-2-propanol, 1, 4-dibromo-2-butene and 1, 4-dibromo-butane, respectively. The structures of GS-1, GS-2, and GS-3 were characterized by Fourier-transform infrared (FT-IR) spectrometry and proton nuclear magnetic resonance (¹H NMR), and their Krafft temperature, surface activity, emulsification performance, foam performance, and wettability were measured. The results show that three kinds of Gemini surfactants GS-1, GS-2, GS-3 are successfully prepared, and their Krafft temperatures are all less than 0℃, which provides a theoretical possibility for their use in low temperature environments with maintained high surface activity. Then, the critical micelle concentration (CMC) values of GS-1, GS-2, GS-3 are 7.7×10^-5, 7.08×10^-5, and 2.63×10^-6 mol/L, respectively, which are consistent with the expected results. The CMC value of the Gemini surfactant is 1~2 orders of magnitude lower than that of the conventional surfactant single alkyl chain. In addition, the synthesized surfactants all show good surface a ctivity, emulsifying properties, and the ability to stabilize foam.
- Gemini surfactant,
- Eco-friendly substances,
- Surface activity
1. [1]
  TAWFIK S M. Synthesis, surface, biological activity and mixed micellar phase properties of some biodegradable gemini cationic surfactants containing oxycarbonyl groups in the lipophilic part[J]. J Ind Eng Chem, 2015,28:171-183. doi: 10.1016/j.jiec.2015.02.011
2. [2]
  WANG Y K, JIANG Y J, GENG T. Synthesis, surface/interfacial properties, and biological activity of amide-based gemini cationic surfactants with hydroxyl in the spacer group[J]. Colloids Surf A, 2019,563:1-10. doi: 10.1016/j.colsurfa.2018.11.061
3. [3]
  MENGER F M, KEIPER J S, AZOV V. Gemini surfactants with acetylenic spacers[J]. Langmuir, 2000,16(5):2062-2067. doi: 10.1021/la9910576
4. [4]
  SHARMA R, KAMAL A, ABDINEJAD M. Advances in the synthesis, molecular architectures and potential applications of gemini surfactants[J]. Adv Colloid Interface Sci, 2017,248:35-68. doi: 10.1016/j.cis.2017.07.032
5. [5]
  HASANOV E E, RAHIMOV R A, ABDULLAYEV Y. New class of cocogem surfactants based on hexamethylenediamine, propylene oxide, and long chain carboxylic acids: theory and application[J]. J Ind Eng Chem, 2020,86:123-135. doi: 10.1016/j.jiec.2020.02.019
6. [6]
  ANDREOZZI P, PONS R, PÉREZ L. Gemini surfactant binding onto hydrophobically modified silica nanoparticles[J]. J Phys Chem C, 2008,112(32):12142-12148. doi: 10.1021/jp8026989
7. [7]
  YOUSEFI A, JAVADIAN S, NESHATI J. A new approach to study the synergistic inhibition effect of cationic and anionic surfactants on the corrosion of mild steel in HCl solution[J]. Ind Eng Chem Res, 2014,53(13):5475-5489. doi: 10.1021/ie402547m
8. [8]
  FENG L W, YIN C J, ZHANG H L. Cationic Gemini surfactants with a bipyridyl spacer as corrosion inhibitors for carbon steel[J]. ACS Omega, 2018,3(12):18990-18999. doi: 10.1021/acsomega.8b03043
9. [9]
  LUO X H, ZHONG J W, ZHOU Q L. Cationic reduced graphene oxide as self-aligned nanofiller in the epoxy nanocomposite coating with excellent anticorrosive performance and its high antibacterial activity[J]. ACS Appl Mater Interfaces, 2018,10(21):18400-18415. doi: 10.1021/acsami.8b01982
10. [10]
  GUO N N, ZHENG M Y, WANG T R. Application of quaternary ammonium gemini surfactant in leather industry[J]. Leather Chem, 2019,36(4):24-29.
11. [11]
  LV Q C, LI Z M, LI B F. Study of nanoparticle surfactant-stabilized foam as a fracturing fluid[J]. Ind Eng Chem Res, 2015,54(38):9468-9477. doi: 10.1021/acs.iecr.5b02197
12. [12]
  LI K X, JING X Q, HE S. Static adsorption and retention of viscoelastic surfactant in porous media: EOR implication[J]. Energy Fuels, 2016,30(11):9089-9096. doi: 10.1021/acs.energyfuels.6b01732
13. [13]
  FU L P, LIAO K L, GE J J. Synergistic effect of sodium p-perfluorononenyloxybenzenesulfonate and alkanolamide compounding system used as cleanup additive in hydraulic fracturing[J]. Energy Fuels, 2020,34(6):7029-7037. doi: 10.1021/acs.energyfuels.0c01043
14. [14]
  LIU X M, SONG C, WANG S Y. Synthesis and properties of cationic Gemini surfactants with amide group[J]. Chem Res Appl, 2011,23(2):184-188.
15. [15]
  SUN Y, PAN Ha, HAN F. Synthesis and properties of quaternary ammonium gemini surfactants with hydroxyl in head groups[J]. China Surfactant Deterg Cosmet, 2019,49(3):135-140.
16. [16]
  WU Z F, LI Y L, LI J. Study on the properties and self-assembly of fatty alcohol ether carboxylic ester anionic surfactant and cationic surfactant in a mixed system[J]. New J Chem, 2019,43(31):12494-12502. doi: 10.1039/C9NJ02407G
17. [17]
  GUO H, ZHUANG Y W, PANG H Y. Studies on the reaction mechanism of cationic quaternary ammonium gemini serfactant by IR spectroscopy[J]. Spectrosc Spectr Anal, 2018,38(10):3-4.
18. [18]
  DAVEY T M, DUCKER W A, HAYMAN A R. Krafft temperature depression in quaternary ammonium bromide surfactants[J]. Langmuir, 1998,14(12):3210-3213. doi: 10.1021/la9711894
19. [19]
  HOQUE J, AKKAPEDDI P, YARLAGADDA V. Cleavable cationic antibacterial amphiphiles: synthesis, mechanism of action, and cytotoxicities[J]. Langmuir, 2012,28(33):12225-12234. doi: 10.1021/la302303d
20. [20]
  PEI X M, YOU Y, ZHAO J X. Adsorption and aggregation of 2-hydroxyl-propanediyl-α, ω-bis(dimethyldodecyl ammonium bromide) in aqueous solution: effect of intermolecular hydrogen-bonding[J]. J Colloid Interface Sci, 2010,351(2):457-265. doi: 10.1016/j.jcis.2010.07.076
21. [21]
  LIU X M, LIAO X, ZHANG S H. Physicochemical properties of noncovalently constructed sugar-based pseudogemini surfactants: evaluation of linker length influence[J]. J Chem Eng Data, 2019,64(1):60-68. doi: 10.1021/acs.jced.8b00459
22. [22]
  ROSEN M J, KUNJAPPU J T. Surfactants and interfacial phenomena[M]. CUI Z G, JIANG J Z, et al. Trans. 5^th Ed. Trans. Beijing: Chemical Industry Press, 2014: 44-45.
23. [23]
  XU D Q, NI X Y, ZHANG C Y. Synthesis a nd properties of biodegradable cationic gemini surfactants with diester and flexible spacers[J]. J Mol Liq, 2017,240:542-548. doi: 10.1016/j.molliq.2017.05.092
24. [24]
  ABO-RIYA M, TANTAWY A H, EL-DOUGDOUG W. Synthesis and evaluation of novel cationic gemini surfactants based on guava crude fat as petroleum-collecting and dispersing agents[J]. J Mol Liq, 2016,221:642-650. doi: 10.1016/j.molliq.2016.05.083
25. [25]
  WANG G Y, QU W S, DU Z P. Adsorption and aggregation behavior of tetrasiloxane-tailed surfactants containing oligo(ethylene oxide) methyl ether and a sugar moiety[J]. J Phys Chem B, 2011,115(14):3811-3818. doi: 10.1021/jp110578u
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
3. [3]
  Zizheng LU , Wanyi SU , Qin SHI , Honghui PAN , Chuanqi ZHAO , Chengfeng HUANG , Jinguo PENG . Surface state behavior of W doped BiVO₄ photoanode for ciprofloxacin degradation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 591-600. doi: 10.11862/CJIC.20230225
4. [4]
  Xinlong WANG , Zhenguo CHENG , Guo WANG , Xiaokuen ZHANG , Yong XIANG , Xinquan WANG . Enhancement of the fragile interface of high voltage LiCoO₂ by surface gradient permeation of trace amounts of Mg/F. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 571-580. doi: 10.11862/CJIC.20230259
5. [5]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
6. [6]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
7. [7]
  Zhaomei LIU , Wenshi ZHONG , Jiaxin LI , Gengshen HU . Preparation of nitrogen-doped porous carbons with ultra-high surface areas for high-performance supercapacitors. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 677-685. doi: 10.11862/CJIC.20230404
8. [8]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
9. [9]
  Xinyu ZENG , Guhua TANG , Jianming OUYANG . Inhibitory effect of Desmodium styracifolium polysaccharides with different content of carboxyl groups on the growth, aggregation and cell adhesion of calcium oxalate crystals. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1563-1576. doi: 10.11862/CJIC.20230374
10. [10]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
11. [11]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
12. [12]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
13. [13]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
14. [14]
  Qiang ZHAO , Zhinan GUO , Shuying LI , Junli WANG , Zuopeng LI , Zhifang JIA , Kewei WANG , Yong GUO . Cu₂O/Bi₂MoO₆ Z-type heterojunction: Construction and photocatalytic degradation properties. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 885-894. doi: 10.11862/CJIC.20230435
15. [15]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
16. [16]
  Yujia LI , Tianyu WANG , Fuxue WANG , Chongchen WANG . Direct Z-scheme MIL-100(Fe)/BiOBr heterojunctions: Construction and photo-Fenton degradation for sulfamethoxazole. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 481-495. doi: 10.11862/CJIC.20230314
17. [17]
  Xiutao Xu , Chunfeng Shao , Jinfeng Zhang , Zhongliao Wang , Kai Dai . Rational Design of S-Scheme CeO₂/Bi₂MoO₆ Microsphere Heterojunction for Efficient Photocatalytic CO₂ Reduction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309031-. doi: 10.3866/PKU.WHXB202309031
18. [18]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
19. [19]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
20. [20]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013

Get Citation

PDF

XML

Metrics

PDF Downloads(34)
Abstract views(2914)
HTML views(620)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142