双十八烷基四羟乙基二溴丙二铵的微波合成及其性能研究

彭思玉; 郑成; 毛桃嫣; 魏渊; 宋华峰

doi:10.11949/j.issn.0438-1157.20181393

您当前的位置：

首页 >

文章列表页 >

双十八烷基四羟乙基二溴丙二铵的微波合成及其性能研究

材料化学工程与纳米技术 | 更新时间：2020-06-24

- 双十八烷基四羟乙基二溴丙二铵的微波合成及其性能研究
- Microwave synthesis and properties of dioctadecyl tetrahydroxyethyl dibromopropane diammonium
- 化工学报 2019年第S1期页码：202-210
- 作者机构：
  
  1.广州大学精细化工研究所，广东广州 510006
  2.广州科技职业技术学院，广东广州 510550
- 作者简介：
  
  彭思玉（1994—），女，硕士研究生，575570774@qq.com
  郑成（1955—），男，博士，教授，zhengcheng5512@163.com
- 基金信息：
  
  国家自然科学基金项目(21878058)
- DOI：10.11949/j.issn.0438-1157.20181393
  中图分类号： TQ 423.99
- 收稿：2018-11-21，
  
  修回：2018-11-26，
- 稿件说明：
移动端阅览
彭思玉, 郑成, 毛桃嫣, 魏渊, 宋华峰. 双十八烷基四羟乙基二溴丙二铵的微波合成及其性能研究[J]. 化工学报, 2019, 70(S1): 202-210

PENG Siyu, ZHENG Cheng, MAO Taoyan, WEI Yuan, SONG Huafeng. Microwave synthesis and properties of dioctadecyl tetrahydroxyethyl dibromopropane diammonium[J]. CIESC Journal, 2019, 70(S1): 202-210
彭思玉, 郑成, 毛桃嫣, 魏渊, 宋华峰. 双十八烷基四羟乙基二溴丙二铵的微波合成及其性能研究[J]. 化工学报, 2019, 70(S1): 202-210 DOI： 10.11949/j.issn.0438-1157.20181393.

PENG Siyu, ZHENG Cheng, MAO Taoyan, WEI Yuan, SONG Huafeng. Microwave synthesis and properties of dioctadecyl tetrahydroxyethyl dibromopropane diammonium[J]. CIESC Journal, 2019, 70(S1): 202-210 DOI： 10.11949/j.issn.0438-1157.20181393.

摘要

以十八烷基二乙醇胺、1

3-二溴丙烷为主要原料，在微波高压条件下进行季铵化反应合成了一种双子表面活性剂双十八烷基四羟乙基二溴丙二铵（DTDD），通过红外光谱（IR）和核磁共振（

H NMR）对DTDD进行了表征，并用液相色谱-质谱联用（LC-MS）测定了其纯度。通过单因素、正交实验得到了微波法合成目标产物的最佳合成条件为：设置微波功率为900 W，反应时间8 h，反应温度为140℃，产品收率达92%以上。与传统加热法对比

使用微波合成法反应速率大大提高。性能测试结果表明：对比单链季铵盐（OMDAB），目标产物DTDD具有良好的表面性能，其临界胶束浓度为0.087 g/L，相应的表面张力

(CMC)

为31.09 mN/m。

Abstract

A gemini surfactant called dioctadecyl tetrahydroxyethyl dibromopropane diammonium (DTDD) was synthesized

via

quaternization reaction under the condition of microwave and high pressure using octadecyl diethanolamine and 1

3-dibromopropane as the main raw materials. The target compound was characterized by IR and

H NMR

and its purity was determined by HPLC-ELSD. By analysing the single-factor and orthogonal array design experiments

the optimal synthesis conditions for the synthesis of DTDD by microwave method were determined as follows: microwave power was set to 900W

reaction time was 8h and reaction temperature was 140°C

reaching a yeild of 92%. Compared with the traditional heating method

the reaction rate using microwave synthesis was greatly increased. The critical micelle concentration (CMC)

surface tension

Kraft point

and foam properties of the product and the traditional surfactant octadecylmethyldihydroxyethyl ammonium bromide (OMDAB) were determined. The performance test results showed that compared with OMDAB

the target product had good surface properties with the critical micelle concentration of 0.087 g/L and the corresponding surface tension

(CMC)

of 31.09 mN/m.

关键词

Keywords

references

Ji X , Tian M , Wang Y . Temperature-induced aggregate transitions in mixtures of cationic ammonium gemini surfactant with anionic glutamic acid surfactant in aqueous solution [J]. Langmuir the ACS Journal of Surfaces & Colloids , 2016 , 32 ( 4 ): 972 - 981 .

Mobin M , Aslam R , Aslam J . Non toxic biodegradable cationic gemini surfactants as novel corrosion inhibitor for mild steel in hydrochloric acid medium and synergistic effect of sodium salicylate: experimental and theoretical approach [J]. Materials Chemistry & Physics , 2017 , 191 : 151 - 167 .

Zhou Y , Wang Z , Hursthouse A , et al . Gemini surfactant-modified activated carbon for remediation of hexavalent chromium from water [J]. Water , 2018 , 10 ( 1 ): 91 .

Brunsveld L , Schill J , van Dun S , et al . Synthesis and self-assembly of bay-substituted perylene diimide gemini-type surfactants as off-on fluorescent probes for lipid bilayers [J]. Chemistry - A European Journal , 2018 , 24 ( 30 ): 7734 - 7741 .

Kumar A , Banjare M K , Sinha S , et al . Imidazolium-based ionic liquid as modulator of physicochemical properties of cationic, anionic, nonionic, and gemini surfactants [J]. Journal of Surfactants & Detergents , 2018 , 21 ( 3 ): 355 - 366 .

Asadov Z H , Ahmadova G A , Rahimov R A , et al . Effect of spacer nature on surface properties of new counterion coupled gemini surfactants based on dodecyldiisopropylol amine and dicarboxylic acids [J]. Colloids & Surfaces A Physicochemical & Engineering Aspects , 2018 , 550 : 115 - 122 .

El-Said W A , Moharram A S , Hussein E M , et al . Design, synthesis, anticorrosion efficiency, and applications of novel Gemini surfactants for preparation of small-sized hollow spheres mesoporous silica nanoparticles [J]. Materials Chemistry & Physics , 2018 , 211 : 123 - 136 .

聂红艳 , 徐宝财 , 周雅文 . 特种表面活性剂和功能性表面活性剂(Ⅵ): 双子表面活性剂的性质及应用 [J]. 日用化学工业 , 2009 , 39 ( 5 ): 348 - 353 .

Nie H Y , Xu B C , Zhou Y W . Special surfactants and functional surfactants(Ⅵ): Properties and application of gemini surfactants [J]. China Surfactant Detergent & Cosmetics , 2009 , 39 ( 5 ): 348 - 353 .

高阳 , 刘佳 . 单链型苯并咪唑阳离子与双子型苯并咪唑阳离子表面活性剂的性能比较 [J]. 工程技术研究 , 2017 , ( 6 ): 241 - 242 .

Gao Y , Liu J . Comparison of the properties of benzimidazole cationic imidazoles and benzimidazole cationic surfactants [J]. Engineering and Technological Research , 2017 , ( 6 ): 241 - 242 .

Faure D , Gravier J , Labrot T , et al . Photoinduced morphism of gemini surfactant aggregates [J]. Chemical Communications , 2005 , ( 9 ): 1167 - 1169 .

Chang H , Wang Y , Cui Y , et al . Equilibrium and dynamic surface tension properties of Gemini quaternary ammonium salt surfactants with hydroxyl [J]. Colloids & Surfaces A Physicochemical & Engineering Aspects , 2016 , 500 : 230 - 238 .

Xu Q , Wang L , Xing F . Synthesis and properties of dissymmetric gemini surfactants [J]. Journal of Surfactants & Detergents , 2011 , 14 ( 1 ): 85 - 90 .

卢庆祥 , 傅式洲 , 尹宝霖 , 等 . 季铵盐型双子表面活性剂的合成和性能 [J]. 日用化学工业 , 2009 , 39 ( 2 ): 81 - 84 .

Lu Q X , Fu S Z , Yin B L , et al . Synthesis and properties of quaternary ammonium Gemini surfactants [J]. China Surfactant Detergent & Cosmetics , 2009 , 39 ( 2 ): 81 - 84 .

郭乃妮 , 郑敏燕 , 杨连利 . 季铵盐阳离子双酯表面活性剂CDESA的合成研究 [J]. 化学研究与应用 , 2018 , 30 ( 1 ): 105 - 109 .

Guo N N , Zheng M Y , Yang L L . Research on synthesis of quaternary ammonium salt cationic diester surfactants CDESA [J]. Chemical Research and Application , 2018 , 30 ( 1 ): 105 - 109 .

Neochoritis C G , Zarganestzitzikas T , Tsoleridis C A , et al . One-pot microwave assisted synthesis under green chemistry conditions, antioxidant screening, and cytotoxicity assessments of benzimidazole Schiff bases and pyrimido[1,2-a]benzimidazol-3(4H)-ones [J]. European Journal of Medicinal Chemistry , 2011 , 46 ( 1 ): 297 - 306 .

毛展 . 微波辅助非均相催化剂用于绿色有机合成的研究 [D]. 上海 : 上海师范大学 , 2016 .

Mao Z . Microwave-assisted heterogeneous catalysts for green organic synthesis [D]. Shanghai : Shanghai Normal University , 2016 .

胡雪原 . 离子液体和微波技术在绿色有机合成中的应用 [D]. 新乡 : 河南师范大学 , 2005 .

Hu X Y . Application of ionic liquid and microwave technology in green organic synthesis [D]. Xinxiang : Henan Normal University , 2005 .

Ergan B T , Bayramoglu M . Investigation of the microwave effect: a new approach for the solvent effect on the microwave-assisted decomposition reaction of 2,2′-azobis(isobutyronitrile) [J]. Industrial & Engineering Chemistry Research , 2014 , 53 ( 33 ): 13016 - 13022 .

Lin J , Zhu M , Wu X , et al . Microwave-assisted synthesis of trisiloxane superspreader and its superspreading behavior on plant leaves surfaces [J]. Colloids & Surfaces A Physicochemical & Engineering Aspects , 2016 , 511 : 190 - 200 .

Umrao S , Gupta T K , Kumar S , et al . Microwave-assisted synthesis of boron and nitrogen co-doped reduced graphene oxide for the protection of electromagnetic radiation in Ku-band [J]. ACS Applied Materials & Interfaces , 2015 , 7 ( 35 ): 19831 - 19842 .

韦星船 , 郑成 , 刘晓国 , 等 . 一种季铵盐双子表面活性剂的微波合成及性能研究 [J]. 化学研究与应用 , 2009 , 21 ( 3 ): 338 - 343 .

Wei X C , Zheng C , Liu X G , et al . Microwave synthesis and properties of a quaternary ammonium Gemini surfactant [J]. Chemical Research and Application , 2009 , 21 ( 3 ): 338 - 343 .

孙莉 , 张强 , 李春义 , 等 . 双子季铵盐的静态合成及表征 [J]. 化学试剂 , 2015 , 37 ( 10 ): 913 - 915 .

Shun L , Zhang Q , Li C Y , et al . Static synthesis and characterization of cationic Gemini surfactants [J]. Chemical Reagents , 2015 , 37 ( 10 ): 913 - 915 .

程文静 , 郑成 , 毛桃嫣 , 等 . 十八烷基甲基二羟乙基溴化铵的微波合成及性能 [J]. 化工学报 , 2011 , 62 ( 2 ): 566 - 573 .

Cheng W J , Zheng C , Mao T Y , et al . Microwave synthesis technique and properties of octadecylmethyldihydroxyethyl ammonium bromide [J]. CIESC Journal , 2011 , 62 ( 2 ): 566 - 573 .

于涛 , 刘华沙 , 王超群 , 等 . 烷基芳基磺酸钠对烷烃的乳化性能 [J]. 应用化学 , 2011 , 28 ( 5 ): 560 - 564 .

Yu T , Liu H S , Wang C Q , et al . Sodium alkyl sulfonate emulsifying performance on alkanes [J]. Chinese Journal of Applied Chemistry , 2011 , 28 ( 5 ): 560 - 564 .

吕彤 . 表面活性剂合成技术 [M]. 北京 : 化学工业出版社 , 2016 : 133 .

Lyu T . Surfactant Synthesis Technology [M]. Beijing : Chemical Industry Press , 2016 : 133 .

Bekrek V , Nevecn T . A study of effect of temperature on the influence of medium on the reaction of triethylamine with ethyl iodide [J]. Collection of Czechoslovak Chemical Communications , 1991 , 56 ( 4 ): 874 - 879 .

冯刚 . 微波辅助有机反应及微波合成中的“非热效应”研究 [D]. 重庆 : 重庆大学 , 2009 .

Feng G . Microwave-assisted organic reactions and “non-thermal effects” in microwave synthesis [D]. Chongqing : Chongqing University , 2009 .

Alcalde M A , Jover A , Meijide F , et al . Synthesis and characterization of a new gemini surfactant derived from 3α,12α-dihydroxy-5β-cholan-24-amine (steroid residue) and ethylenediamintetraacetic acid (spacer) [J]. Langmuir the ACS Journal of Surfaces & Colloids , 2008 , 24 ( 12 ): 6060 - 6066 .

Han L , Ye Z , Chen H , et al . The interfacial tension between cationic gemini surfactant solution and crude oil [J]. Journal of Surfactants & Detergents , 2009 , 12 ( 3 ): 185 - 190 .

李晓萍 , 金向军 . Gemini表面活性剂的结构特性及其应用 [J]. 白城师范学院学报 , 2006 , 20 ( 4 ): 29 - 31 .

Li X P , Jin X J . Structural properties of Gemini surfactants and their applications [J]. Journal of Baicheng Normal University , 2006 , 20 ( 4 ): 29 - 31 .

王丽艳 , 赵明 , 邢凤兰 , 等 . 双子表面活性剂 [M]. 北京 : 化学工业出版社 , 2013 : 33 .

Wang L Y , Zhao M , Xing F L , et al . Gemini Surfactants [M]. Beijing : Chemical Industry Press , 2013 : 33 .

浏览量

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

新型磁性纳米粒子Fe3O4@CPAM对稠油微波破乳的促进效应研究

双十八烷基二羟乙基溴化铵的微波合成及性能

季铵盐氟碳表面活性剂复配体系的性能研究

异质结构MoS2/RGO/NiFe2O4复合材料的构筑及电磁波吸收性能研究

片状LiFePO4/C正极材料制备及其电化学性能研究