以油酸为原料的新型生物基支链十七烷基苯磺酸钠的合成及性质

doi:10.3866/PKU.WHXB201608231

物理化学学报 >> 2016, Vol. 32 >> Issue (11): 2753-2760.doi: 10.3866/PKU.WHXB201608231

以油酸为原料的新型生物基支链十七烷基苯磺酸钠的合成及性质

卞鹏程¹,张大鹏¹,刚洪泽¹,刘金峰¹,牟伯中^1,²,杨世忠^1,*()

¹ 华东理工大学应用化学研究所,生物反应器工程国家重点实验室,上海200237
² 上海生物制造技术合作创新中心,上海200237

收稿日期:2016-05-23 发布日期:2016-11-08
通讯作者: 杨世忠 E-mail:meor@ecust.edu.cn
基金资助:
国家自然科学基金(51574125);国家自然科学基金(21203063);国家高技术研究发展计划项目（863）(2013AA064403);国家教育部高等学校优秀青年教师研究基金(WJ1514313)

Synthesis and Properties of a Novel Bio-Based Branched Heptadecylbenzene Sulfonate Derived from Oleic Acid

Peng-Cheng BIAN¹,Da-Peng ZHANG¹,Hong-Ze GANG¹,Jin-Feng LIU¹,Bo-Zhong MU^1,²,Shi-Zhong YANG^1,*()

¹ State Key Laboratory of Bioreactor Engineering and Institute of Applied Chemistry, East China University of Science and Technology, Shanghai 200237, P. R. China
² Shanghai Collaborative Innovation Center for Biomanufacturing Technology, Shanghai 200237, P. R. China

Received:2016-05-23 Published:2016-11-08
Contact: Shi-Zhong YANG E-mail:meor@ecust.edu.cn
Supported by:
the National Natural Science Foundation of China(51574125);the National Natural Science Foundation of China(21203063);National High Technology Research and Development Program of China(2013AA064403);Foundation of the Ministry of Education of China for Outstanding Young Teachers in University(WJ1514313)

摘要/Abstract

摘要：

生物基表面活性剂由于其可再生资源和优异的表面/界面性质吸引了越来越多的关注。本文以可再生的油酸为原料，通过四步反应，制备了新型生物基支链表面活性剂，并评价了其表/界面性质、润湿性和生物降解性能。该新型生物基支链表面活性剂为4-（1-十七烷基）苯磺酸钠（9ΦC17S），依次经过烷基化反应、脱羧反应、磺化反应和中和反应而制得。其化学结构已通过电喷雾质谱、红外光谱和核磁共振波谱得以确认。4-（1-十七烷基）苯磺酸钠展现出良好的表/界面张力，临界胶束浓度（CMC）为317.5 mg·L^-1，CMC处的表面张力为32.54 mN·m^-1，当水溶液中碳酸钠浓度为8.48×10⁴ mg·L^-1、4-（1-十七烷基）苯磺酸钠浓度为8.36×10⁴ mg·L^-1时，油水的界面张力约为10^-2 mN·m^-1。此外，4-（1-十七烷基）苯磺酸钠在生物降解性和润湿性方面也显示出了良好的性能，最终生物降解评分为2.99，0.500 g·L^-1 9ΦC17S溶液的气液固接触角为63.08°。该新型生物基表面活性剂丰富了以可再生资源为原料的生物基表面活性剂的结构多样性。

关键词: 生物基表面活性剂, 支链十七烷基苯磺酸钠, 脱羧, 油酸, 可再生资源

Abstract:

Bio-based surfactants have attracted increasing attention because they are made from renewable resources and have excellent surface/interfacial properties. In this study we prepared a novel bio-based branched alkylbenzene sulfonate surfactant by a four-step route using renewable oleic acids as starting materials. We evaluated the surface behavior, wettability, and biodegradability of our surfactant. The surfactant, 4-(1-heptadecyl) benzene sodium sulfonate (9ΦC17S), was synthesized using a facile four-step route involving alkylation, decarboxylation, sulfonation and neutralization, respectively. The chemical structure of 4-(1-heptadecyl) benzene sodium sulfonate was confirmed by infrared (IR) spectroscopy, electrospray ionization high resolution mass spectrometry (ESI HRMS) and ¹H nuclear magnetic resonance (¹H NMR) spectroscopy. The surfactant demonstrated an excellent surface tension of 32.54 mN·m^-1 at the critical micelle concentration (CMC) of 317.5 mg·L^-1 and outstanding interfacial tension of~10^-2 mN·m^-1 at 8.36×10⁴ mg·L^-1 with 8.48×10⁴ mg·L^-1 Na₂CO₃. The surfactant also showed good biodegradability with an ultimate biodegradation score of 2.99. The surfactant had good wettability with an air/water/solid contact angle (θ_average) of 63.08° for a 0.500 g·L^-1 9ΦC17S solution. This novel bio-based branched surfactant contributes to the structural diversity of biobased surfactants from renewable feedstock.

Key words: Bio-based surfactant, Branched heptadecylbenzene sulfonate, Decarboxylation, Oleic acid, Renewable feedstock

MSC2000:

O647

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卞鹏程,张大鹏,刚洪泽,刘金峰,牟伯中,杨世忠. 以油酸为原料的新型生物基支链十七烷基苯磺酸钠的合成及性质[J]. 物理化学学报, 2016, 32(11): 2753-2760.

Peng-Cheng BIAN,Da-Peng ZHANG,Hong-Ze GANG,Jin-Feng LIU,Bo-Zhong MU,Shi-Zhong YANG. Synthesis and Properties of a Novel Bio-Based Branched Heptadecylbenzene Sulfonate Derived from Oleic Acid[J]. Acta Phys. -Chim. Sin., 2016, 32(11): 2753-2760.

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以油酸为原料的新型生物基支链十七烷基苯磺酸钠的合成及性质

Synthesis and Properties of a Novel Bio-Based Branched Heptadecylbenzene Sulfonate Derived from Oleic Acid

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