Synthesis of Ester Based Cationic Pyridinium Gemini Surfactants and Appraisal of Their Surface Active Properties

Abstract

New pyridinium gemini surfactants have been synthesized by esterification of halogenated carboxylic acids with long chain fatty alcohols furnishing respective esters (dodecyl‐2‐chloroacetate, tetradecyl‐2‐chloroacetate, hexadecyl‐2‐chloroacetate, dodecyl‐2‐bromoacetate, tetradecyl‐2‐bromoacetate and hexadecyl‐2‐bromoacetate) followed by their subsequent treatment with 4,4′‐trimethylene dipyridine resulting in the formation of title Gemini surfactants: 4,4′‐(propane‐1,3‐diyl)bis1‐{2‐(dodecyloxy)‐2‐oxoethyl}; 4,4′‐(propane‐1,3‐diyl)bis{1‐(2‐(tetradecyloxy)‐2‐oxoethyl}; 4,4′‐(propane‐1,3‐diyl)bis{1‐(2‐(hexadecyloxy)‐2‐oxoethyl} dipyridinium chlorides; 4,4′‐(propane‐1,3‐diyl)bis{1‐(2‐(dodecyloxy)‐2‐oxoethyl}; 4,4′‐(propane‐1,3‐diyl)bis{1‐(2‐(tetradecyloxy)‐2‐oxoethyl} and 4,4′‐(propane‐1,3‐diyl)bis{1‐(2‐(hexadecyloxy)‐2‐oxoethyl} dipyridinium bromides. Their identifications are based on IR, 1H‐NMR, 13C‐NMR, DEPT, COSY and Mass spectral studies. Their surface active properties were also evaluated on the basis of surface tension and conductivity measurements.

Gemini Pyridinium Surfactants: Synthesis and Their Surface Active Properties

“…The progress of reaction was monitored by thin layer chromatography [silica gel G coated (0.25 mm thick) glass plates using hexane: ethyl acetate (98:2) as mobile phase, the spots were visualized in iodine]. The reaction got completed in 3 h. The method of purification of the resulting esters was reported in our previous work [21]. The yields of resulting esters are reported in parenthesis [2-…”

“…for 1, 6.364 g; for 2, 5.816 g; for 3, 5.241 g; for 4, 7.244 g; for 5, 6.682 g; for 6, 612.24 g; and 4,4 0 -trimethylenedipyridine (1.982 g) were taken. In each case, the resulting crude product was crystallized with ether and subsequently recrystallized in cold acetone to get the pure compounds (7)(8)(9)(10)(11)(12) which were characterized on the basis of IR, 1 H-, 13 Conductivity Measurements [21,22] The CMC of these surfactants (7)(8)(9)(10)(11)(12) were determined by the conductivity method. The conductivity as a function of surfactant concentration was measured at 25°C.…”

Preparation, Characterization and Properties of Novel Cationic Gemini Surfactants with Rigid Amido Spacer Groups

“…Surfactants are widely applied in many fields from consumer products to industrial applications. In comparison with conventional single-chain surfactants, gemini surfactants exhibit superior aqueous solution properties, such as lower critical micelle concentration (CMC), higher surface activity, better emulsifying performances, lower Krafft point and unusual aggregation morphologies [1][2][3][4][5].…”

Comparison Between Phase Behavior of Gemini Imidazoliums and Monomeric Ionic Liquid Surfactants in W/O Microemulsion Systems

“…These surfactants consist of two hydrocarbon tails and two polar head groups connected through a rigid or flexible spacer. [1][2][3][4][5][6][7][8] These gemini surfactants possess better physicochemical properties such as much lower critical micelle concentration (cmc), higher solubilization ability, better wetting properties, etc., than the corresponding traditional single-chain surfactants. [9][10][11][12][13][14][15][16][17] They are also referred as ''green surfactants,'' as less amount of geminis can be used as compared to conventional surfactants owing to their very low cmc values.…”