不同功能基团的有机盐作为低相对分子质量凝胶因子对原油的成胶性能

doi:10.11944/j.issn.1000-0518.2018.12.180010

摘要/Abstract

摘要：

低相对分子质量凝胶作为治理原油泄漏的材料具有一些优异的性能,但其在水油相中的成胶规律仍不明确,本文以有机酸及有机胺为原料设计合成了一系列有机盐。通过核磁共振波谱仪(NMR)、傅里叶红外光谱仪(FTIR)、扫描电子显微镜(SEM)和倒挂实验等技术手段表征了有机盐的结构和成胶性能。结果表明,有机盐A3C3(A3:肉桂酸;C3:月桂胺)在室温下能使原油形成稳定凝胶,成胶溶度为质量分数6%,该分子在溶剂中自组装形成树枝状三维网状结构。凝胶的形成需要分子间π-π堆积作用、氢键、静电作用和范德华力等多种作用力协同作用,分子间的π-π堆积作用有利于凝胶的形成,含有多个苯环的凝胶因子更易在芳香族溶剂中形成凝胶。这些成胶规律对处理原油泄漏的低相对分子质量凝胶因子的设计合成具有实际的指导意义。

关键词: 低相对分子质量凝胶因子, 原油泄漏, 回收, 超分子作用力

Abstract:

Low relative molecular mass gelators have attracted much attention due to their promising properties in oil spill recovery. However, designing a gelator is still challenging. In this paper, a series of organic salts was synthesized. Their structures and gelling properties were characterized by nuclear magnetic resonance spectroscopy(NMR), Fourier transform infrared spectrometer(FTIR), scanning electron microscope(SEM), vial inversion test. The results show that A3C3(A3-cinnamic acid, C3-Laurylamine) can readily gel in crude oil at room temperature. The critical gelation concentration is 6%(mass fraction). A3C3 self-assembles into dendritic three-dimensional entangled network. The formation of gel is due to the synergy between different supramolecular interactions. The increased π-π stacking interactions of the gelator made it easier to gelate. The gelators with phenyl groups are tending to gel in aromatic solvent. This gelling performance will contribute significantly toward the development of the design of organic soft materials.

Key words: low relative molecular mass gelator, oil spill, recovery, supramolecular interaction

王雪松, 陈银珠, 夏立全, 李运, 陈丽萍, 陈雯丹. 不同功能基团的有机盐作为低相对分子质量凝胶因子对原油的成胶性能[J]. 应用化学, 2018, 35(12): 1462-1469.

WANG Xuesong, CHEN Yinzhu, XIA Liquan, LI Yun, CHEN Liping, CHEN Wendan. Gelation Properties of Organic Salts as Low Relative Molecular Mass Gelators with Various Functional Groups in Raw Petroleum[J]. Chinese Journal of Applied Chemistry, 2018, 35(12): 1462-1469.

参考文献

[1]	Han W H,Ju H J.A Study on the Prevention of Spill of Fuel Oils and Lubricating Oils for Sunken Ships[J]. J Korean Soc Mar Environ Saf,2015,21(3):309-314.
[2]	Dou X Q,Zhang D,Feng C L.Research Progress and Prospect of Low Molecular Weight Gel[J]. Sci Technol Eng,2011,12(7):1671-1815.
[3]	Basu K,Nandi N.Peptide-Based Ambidextrous Bifunctional Gelator:Applications in Oil Spill Recovery and Removal of Toxic Organic Dyes for Waste Water Management[J]. Interface Focus,2017,7(6):6-11.
[4]	Das U K,Trivedi D R,Adarsh N N.Supramolecular Synthons in Noncovalent Synthesis of a Class of Gelators Derived from Simple Organic Salts:Instant Gelation of Organic Fluids at Room Temperature via in Situ Synthesis of the Gelators[J]. J Org Chem,2009,74(18):7111-7121.
[5]	Buerkle L E,Rowan S J.Supramolecular Gels Formed from Multi-component Low Molecular Weight Species[J]. Chem Soc Rev,2012,41(18):6089-6102.
[6]	Yu X D,Chen L M,Zhang M M.Low-Molecular-Mass Gels Responding to Ultrasound and Mechanical Stress:Towards Self-Healing Materials[J]. Chem Soc Rev,2014,43(15):5346-5371.
[7]	Darshak R,Trivedi A B,Parthasarathi D.An Easy to Prepare Organic Salt as a Low Molecular Mass Organic Gelator Capable of Selective Gelation of Oil from Oil/Water Mixtures[J]. Chem Mater,2003,21(15):3971-3973.
[8]	Darshak R T,Parthasarathi D.Instant Gelation of Various Organic Fluids Including Petrol at Room Temperature by a New Class of Supramolecular Gelators[J]. Chem Mater,2006,18(6):1470-1478.
[9]	Lu J R,Hu J,Liu C L,et al. Water-induced Gel Formation of an Oleanlic Acid-Adenine Conjugate and the Effects of Uracil Derivative on the Gel Stability[J] . Soft Matter,2012,37(8):9576-9580.
[10]	Shen Y T,Li C S,Chang K C,et al. Synthesis, Optical, and Mesomorphic Properties of Self-Assembled Organogels Featuring Phenylethynyl Framework with Elaborated Long-Chain Pyridine-2,6-Dicarboxamides[J]. Langmuir,2009,25(15):8714-8722.
[11]	Amar B,Darshak R T,Parthasarathi D.New Series of Organogelators Derived from a Combinatorial Library of Primary Ammonium Monocarboxylate Salts[J]. Chem Mater,2006,18(16):3795-3800.
[12]	Yang H K,Zhao H,Yang P R,et al. How do Molecular Structures Affect Gelation Properties of Supramolecular Gels? Insights from Low-molecular-weight Gelators with Different Aromatic Cores and Alkyl Chain Lengths[J]. Colloids Surf A,2017,535(44):242-250.
[13]	Zhao C X,Wang H T,Bai B L,et al. Organogels from Unsymmetrical p-Conjugated 1,3,4-Oxadiazole Derivatives[J]. New J Chem,2013,37(5):1454-1460.
[14]	Lofman M,Koivukorpi J,Noponen V.Bile Acid Alkylamide Derivatives as Low Molecular Weight Organogelators:Systematic Gelation Studies and Qualitative Structural Analysis of the Systems[J]. J Colloid Interface Sci,2011,360(112):633-644.