Acta Phys. -Chim. Sin. ›› 2016, Vol. 32 ›› Issue (11): 2753-2760.doi: 10.3866/PKU.WHXB201608231

• ARTICLE • Previous Articles     Next Articles

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 MU1,2,Shi-Zhong YANG1,*()   

  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)

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 (θaverage) 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