Design,synthesis and surface activity of adamantyl Bola-form surfactant

doi:10.3969/j.issn.0438-1157.2013.08.036

CIESC Journal ›› 2013, Vol. 64 ›› Issue (8): 2956-2961.DOI: 10.3969/j.issn.0438-1157.2013.08.036

Previous Articles Next Articles

Design,synthesis and surface activity of adamantyl Bola-form surfactant

FU Shuqin, GUO Jianwei, FU Chang'an, ZHONG Xing, CUI Yingde

Faculty of Chemical Engineering & Light Industry, Guangdong University of Technology, Guangzhou 510006, Guangdong, China

Received:2012-12-21 Revised:2013-03-13 Online:2013-08-05 Published:2013-08-05
Supported by:
supported by University Science and Technology Innovation Key Projects of Guangdong Province(100187),Science and Technology Project of Guangzhou City(2010J-D00051)and the Major Program of Guangdong University of Technology(405095220).

金刚烷基Bola型表面活性剂的设计、合成及表面活性

傅淑琴, 郭建维, 付长安, 钟星, 崔英德

广东工业大学轻工化工学院, 广东广州 510006

通讯作者: 郭建维
作者简介:傅淑琴(1989- ),女,硕士研究生。
基金资助:
广东省高校重点技术创新项目(100187);广州市科技计划项目(2010J-D00051);广东工业大学重大培育专项(405095220)。

Abstract

Abstract: 1,3-Bis(4-hydroxyphenyl)adamantanea(DPAD)was synthesized via Friedel-Crafts alkylation of 1,3-dibromoadamantane and phenol with the catalyst of Lewis acid.Williamson condensation reaction of 1,3-bis(4-hydroxyphenyl)adamantane and halogenated sulfone alkylating reagent and neutralization led to 1,3-bis(4-(2-ethoxyl sodium sulfonate)phenyl)adamantane in alkaline condition.The structures of compounds were characterized by IR,¹H NMR and elemental analysis measurements.The surface tensions of the target compound in different concentrations were tested.The effects of reaction solvent,halogenated sulfone alkylating reagent,reaction temperature and time,and raw material ratio on the yield of the target compound were discussed.The optimal reaction conditions were as follows:DMF as solvent,n(DPAD):n(BrC₂H₄SO₃Na)=1:2.2,then the mixture reacted for 3 h at 60℃.Under the optimized reaction condition,the total-yield of the target compound can reach 72%.

Key words: adamantine, Bola compound, surfactant, synthesis

摘要： 以1,3-二溴金刚烷为起始原料,首先在Lewis酸催化作用下与苯酚发生傅-克烷基化反应生成1,3-二(4-羟苯基)金刚烷(DPAD);DPAD再经Williamson缩合反应和中和反应合成了新型金刚烷基Bola型表面活性剂1,3-二(4-(2-乙氧基磺酸钠)-苯基)金刚烷。采用IR、¹H NMR和元素分析等手段确定了各中间物及产物的结构,测试了1,3-二(4-(2-乙氧基磺酸钠)-苯基)金刚烷的表面活性。考察了关键反应步骤(Williamson缩合反应)溶剂、卤代磺烷基化试剂、反应温度、反应时间和物料比对产物收率的影响。在优化的反应条件下,1,3-二(4-(2-乙氧基磺酸钠)-苯基)金刚烷的总收率可达72%。

关键词: 金刚烷, Bola化合物, 表面活性剂, 合成

CLC Number:

FU Shuqin, GUO Jianwei, FU Chang'an, ZHONG Xing, CUI Yingde. Design,synthesis and surface activity of adamantyl Bola-form surfactant[J]. CIESC Journal, 2013, 64(8): 2956-2961.

傅淑琴, 郭建维, 付长安, 钟星, 崔英德. 金刚烷基Bola型表面活性剂的设计、合成及表面活性[J]. 化工学报, 2013, 64(8): 2956-2961.

References 18

[1]	Raymond M Fuoss,David Edelson.Bolaform electrolytes(Ⅰ):Di-(β-trimethylammonium ethyl)succinate dibromide and related compounds[J].J.Am.Chem.Soc.,1951,73(1):269-273
[2]	Menger F M,Wrenn S.Interfacial and micellar properties of Bolaform electrolytes[J].J.Phys.Chem.,1974,78(14):1387-1390
[3]	Meguro K,Ikeda K,Otsuji A.Physicochemical properties of the α,ω-type surfactant in aqueous solution[J].J.Colloid Interface Sci.,1987,118(2):372-378
[4]	Abid S K,Hamid S M,Sherrington D C.Micellization and surface activity of long-chain monoquaternary and diquaternary ammonium salts[J].J.Colloid Interface Sci.,1987,120(1):245-255
[5]	Jin Yong(金勇),Miao Qing(苗青),Zhang Biao(张彪),Cao Zhifeng(曹志峰).The synthesis and application of Bola surfactants[J].Progress in Chemistry(化学进展),2008,20(6):918-930
[6]	Okahata Yoshio,Kunitake Toyoki.Formation of stable monolayer membranes and related structures in dilute aqueous solution from two-headed ammonium amphiphiles[J].J.Am.Chem.Soc.,1979,101(10):5231-5234
[7]	Wang Mingfeng,Qiu Dengli,Zou Bo,Wu Tao,Zhang Xi.Stabilizing Bolaform amphiphile interfacial assemblies by introducing mesogenic groups[J].Chem.Eur.J.,2003,9(8):1876-1880
[8]	Celine Satge,Robert Granet,Bernard Verneuil,Yves Champavier,Pierre Krausz.Synthesis and properties of new Bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis[J].Carbohydrate Research,2004,339(7):1243-1254
[9]	Jayasuriya N,Bosak S,Regen S L.Design,synthesis and activity of membrane-disrupting Bolaphiles[J].J. Am. Chem.Soc.,1990,112(15):5844-5850
[10]	Burstein M E,Serbin A V,Khakhulina T V,Alymova I V,Stotskaya L L,Bogdan O P,Manukchina E E,Jdanov V V,Sharova N K,Bukrinskaya A G.Inhibition of HIV-1 replication by newly developed adamantane-containing polyanionic agents[J].Antiviral Research,1999,41:135-144
[11]	Fu Chang'an(付长安),Guo Jianwei(郭建维),Liu Sa(刘卅),Cui Yingde(崔英德),Peng Jinping(彭进平),Cui Yihua(崔亦华).A novel synthesis of adamantane polyhydric alcohols by direct oxidation of adamanane[J].CIESC Journal(化工学报),2011,62(12):3428-3433
[12]	Cai Lu(蔡璐),Guo Jianwei(郭建维),Liu Sa(刘卅).Synthesis of adamantane-based betaine and quaternary ammonium surfactants[J].Chinese Journal of Organic Chemistry(有机化学),2011,31(8):1290-1294
[13]	Jean-Paul Mazaleyrat,Michel Wakselman.The Williamson reaction:a new and efficient method for the alternate resolution of 2,2'-bis(bromomethyl)-1,1'-binaphthyl and 1,1'-binaphthalene-2,2'-diol[J].J.Org.Chem.,1996,61(8):2695-2698
[14]	Su X M,Jing X L.Novel adamantine-containing epoxy resin[J].Journal of Applied Polymer Science,2007,106:737-742
[15]	Jiang Huiliang(蒋惠亮),Wang Changjian(王昌建),Yin Fushan(殷福珊),Bao Xingnan(包星南).Synthesis of Bolaform surfactant sodium polypropylene glycol sulphate[J].Journal of Southern Yangtze University(江南大学学报),2005,4(8):367-370
[16]	Negm Nabel A,Mohamed Ammona S.Surface and thermodynamic properties of diquaternary Bola-form amphiphiles containing an aromatic spacer[J].Journal of Surfactants and Detergents,2004,7(1):23-30
[17]	Yan Yun(阎云),Huang Jianbin(黄建滨),Li Zichen(李子臣),Zhao Xiaoli(赵小莉),Ma Jiming(马季铭).Surface property and aggregation behavior of anionic Bolaform surfactant/C12Et3 mixed system[J].Acta Chimica Sinica(化学学报),2002,60(7):1147~1150
[18]	Virginie Neto,Robert Granet,Pierre Krausz.Novel class of non-ionic monocatenary and Bolaform alkylglycoside surfactants.Synthesis by microwave-assisted glycosylation and olefin cross-metathesis or by 'click-chemistry':physicochemical studies[J].Tetrahedron,2010,66(25):4633-4646

Design,synthesis and surface activity of adamantyl Bola-form surfactant

金刚烷基Bola型表面活性剂的设计、合成及表面活性

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

References 18

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Qi WANG, Bin ZHANG, Xiaoxin ZHANG, Hujian WU, Haitao ZHAN, Tao WANG. Synthesis of isoxepac and 2-ethylanthraquinone catalyzed by chloroaluminate-triethylamine ionic liquid/P₂O₅ [J]. CIESC Journal, 2023, 74(S1): 245-249.
[2]	Xin YANG, Xiao PENG, Kairu XUE, Mengwei SU, Yan WU. Preparation of molecularly imprinted-TiO₂ and its properties of photoelectrocatalytic degradation of solubilized PHE [J]. CIESC Journal, 2023, 74(8): 3564-3571.
[3]	Bin LI, Zhenghu XU, Shuang JIANG, Tianyong ZHANG. Clean and efficient synthesis of accelerator CBS by hydrogen peroxide catalytic oxidation method [J]. CIESC Journal, 2023, 74(7): 2919-2925.
[4]	Jiali GE, Tuxiang GUAN, Xinmin QIU, Jian WU, Liming SHEN, Ningzhong BAO. Synthesis of FeF₃ nanoparticles covered by vertical porous carbon for high performance Li-ion battery cathode [J]. CIESC Journal, 2023, 74(7): 3058-3067.
[5]	Yuming TU, Gaoyan SHAO, Jianjie CHEN, Feng LIU, Shichao TIAN, Zhiyong ZHOU, Zhongqi REN. Advances in the design, synthesis and application of calcium-based catalysts [J]. CIESC Journal, 2023, 74(7): 2717-2734.
[6]	Tan ZHANG, Guang LIU, Jinping LI, Yuhan SUN. Performance regulation strategies of Ru-based nitrogen reduction electrocatalysts [J]. CIESC Journal, 2023, 74(6): 2264-2280.
[7]	Wenchao XU, Zhigao SUN, Cuimin LI, Juan LI, Haifeng HUANG. Effect of surfactant E-1310 on the formation of HCFC-141b hydrate under static conditions [J]. CIESC Journal, 2023, 74(5): 2179-2185.
[8]	Yuntong GE, Wei WANG, Kai LI, Fan XIAO, Zhipeng YU, Jing GONG. AFM study of the interaction forces between micro-oil droplets and modified silica surfaces in multiphase dispersion systems [J]. CIESC Journal, 2023, 74(4): 1651-1659.
[9]	Runzhu LIU, Tiantian CHU, Xiaoa ZHANG, Chengzhong WANG, Junying ZHANG. Synthesis and properties of phenylene-containing α,ω-hydroxy-terminated fluorosilicone polymers [J]. CIESC Journal, 2023, 74(3): 1360-1369.
[10]	Feng WANG, Yu CHEN, Hongyan PEI, Dongdong LIU, Jing ZHANG, Lixin ZHANG. Design, synthesis and anti-fungal activity of 1,2,4-oxadiazole derivatives [J]. CIESC Journal, 2023, 74(3): 1390-1398.
[11]	Haiou YUAN, Fangjun YE, Shuo ZHANG, Yiqing LUO, Xigang YUAN. Synthesis of heat-integrated distillation sequences with intermediate heat exchangers [J]. CIESC Journal, 2023, 74(2): 796-806.
[12]	Mengbo ZHANG, Linjin LOU, Yirong FENG, Yuting ZHENG, Haomiao ZHANG, Jingdai WANG, Yongrong YANG. Research progress on synthesis of alkylaluminoxanes [J]. CIESC Journal, 2023, 74(2): 525-534.
[13]	Guojia YU, Dongyu JIN, Zhiyong ZHOU, Fan ZHANG, Zhongqi REN. Advances in the design, synthesis and application of porous liquids [J]. CIESC Journal, 2023, 74(1): 257-275.
[14]	Qiuhua ZHANG, Manlu LIU, Zheng WANG, Yiming ZHANG, Haijia SU. Biosynthesis of vitamin K2 and functional analysis of the biosynthetic enzymes involved in its menadione moiety [J]. CIESC Journal, 2023, 74(1): 342-354.
[15]	Yi LIAO, Yabin NIU, Yanqiu PAN, Lu YU. Modeling the effects of mixed surfactants on the behaviors and properties of the oil-water interface with molecular dynamics [J]. CIESC Journal, 2022, 73(9): 4003-4014.