Design And Synthesis Of Novel Gemini Surfactant

With the fast development of society and economy and the increasing deterioration of environment, the low activity and non-environment-friendly traditional surfactant hasn't met with the need of the economy of nation and the life of people. Consequently, it is urgen mission of chemists to research and develop the high efficient and environment-friendly surfactants. Gemini surfactants are honored as "nouveau surfactant" with superior performance of physics and chemistry, which emerges as the times required. It is another milestone of phylogeny of surfactant industry.As a new generational surfactant, Gemini surfactants have commercial development value. However, the synthesis of Gemini surfactants is difficult, and the required materials are expensive. Most of the Gemini surfactants are still in the experimental stage or only in research, it is a long distance away from large-scale industrialization. Though with excellent properties, the Gemini surfactants aren't accepted because of high cost.There are two ways to solve the above problems: (1) Compound with ordinary surfactants and look for some good synergistic effect systems that the interaction parameter (β) is very low. (2) Adopt cheap raw materials and apply environment-friendly process from the perspective of synthesis. Comparing the two methods, the last is the focus of the future research.The author designed and synthesized some new Gemini surfactants with relatively cheap raw materials and environment-friendly process. Main aspects are followed:First, the synthesis of cationic Gemini surfactants.Three series of cationic Gemini surfactants were synthesized:1) The long chain alkyl glycidyl ethers were prepared by the long chain alcohols reacting with epichlorohydrin, then, the long chain alkyl glycidyl ethers reacted with dimethyl amine and were converted to the corresponding tertiary amines, at last, the synthesis of bis-quaternary ammonium salts with two alkyl chains were achieved by the forementioned tertiary amine reacting with 1,4-dibromobutane.2) The long chain alkyl glycidyl ethers were synthesized in the same way, which reacted with long-chain alkyldimethylamines and their hydrochlorides, mono-quaterary ammonium salts with two alkyl chains were prepared.3) Hydroquinone diglycidyl ether was synthesized by the successive treatment of a mixture of epichlorohydrin and hydroquinone. Hydroquinone diglycidyl ether reacted with long-chain alkyldimethylamines and their hydrochlorides, then the ultimate targets were obtained.Their structures were identified by NMR and IR.Second, the synthesis of zwitterion Gemini surfactants.Two series of zwitterion Gemini surfactants were synthesized:1) The long chain alkyl glycidyl ether were prepared by the long chain alcohols reacting with epichlorohydrin, which reacted with long-chain alkyldimethylamines and their hydrochlorides, then the resultant mono-quaterary ammonium salts with two alkyl chains reacted with chlorosulfonic acid and yielded zwitterion Gemini surfactants containing sulphonate.2) In the same way, the mono-quaterary ammonium salts with two alkyl chains were synthesized, and then chlorosulfonic acid was replaced by phosphorus oxychloride and obtained zwitterion Gemini surfactants containing phosphate.Their structures were identified by IR and NMR.Third, the synthesis of nonionic Gemini surfactants containing β-CD.Gemini surfactants containing β-cyclodextrins were tried.to be synthesized. Firstly, mono-6-deoxy-6(p-toIylsulfonyl)-β-cyclodextrin were synthesized by β-cyclodextrin reacting with p-tolylsulfonyl chloride, which reacted with 1,2-ethylenediamine ( or 1,6-Diaminohexane) and yielded the β-cyclodextrin dimer bridged with 1,2-diaminoethane (or 1,6-Diaminohexane). Secondly, the synthesis of Gemini surfactants containing β-cyclodextrins were achieved by the β-cyclodextrin dimer reacting with the long chain alkyl glycidyl ether. The structures of the corresponding compounds were identified by NMR. The main innovations of the dissertation were as follows:1) The author firstly designed and synthesized two new types Gemini surfactants which haven't been reported.2) The author adopted relatively cheap raw materials and environment-friendly process. Furthermore, the author optimized the reaction steps and improved the yield of the reaction products.3) The author improved the methods of purification, and obtained the high purified products.