Synthesis And Deirvation Of Lipidic Amino Acids

The lipidic amino acids which both have long chain lipid lipophilicity andamphoteric characteristic of amino acid are widely used in biological medicine,cosmetics and personal care industry. In this paper, a synthesis route of lipidic aminoacids was developed，which was based on α-chloro fatty acids(CFA) derived fromnatural fatty acid as raw materials. α-amino decanoic acid(ADA), α-aminotetradecanoic acid(ATA), α-amino hexadecanoic acid(AHA) and N-methyl-α-aminodecanoic acid(NMADA) were synthesized. After optimizing the synthetic technologyof α-amino decanoic acid(ADA) and N-methyl-α-amino decanoic acid(NMADA), theyield of ADA and NMADA can reach90%, respectively. What’s more, the technologyof synthesising fatty amine by decarboxylation of ADA and NMADA is exploreed,aiming to provide new ideas for fatty amine industry. The main research conclusionswere as follows:ADA、ATA、AHA were synthesized by the amination of α-chloro fatty acid(CFA) and their structures were identified by FTIR and1H-NMR, the relativemolecular weight were confirmed by ESI-MS. The effects of reaction temperature,reaction time, catalyst, ratio of raw materials on the yield of ADA were investigated.The yield of ADA was81%under the optimum condition which was accounted as thecompetition of the side hydrolysis reaction. Based on the optimization of reactioncondition, a temperature programming was applied and the yield of ADA achieved91%under the optimal temperature programming technology when the aminationproceeded at70℃for12h following100℃for4h with n(ammonia): n(CDA)=20:1.NMADA were synthesized by the amination of α-chloro dodecanoic acid (CDA)with methylamine and the molecular structure of NMADA were identified by FTIRand1H-NMR, the relative molecular weight were confirmed by ESI-MS. The effectsof reaction temperature, reaction time, ratio of raw materials on the yield of NMADAwere investigated. The yield of NMADA was92%under the optimum condition. Atemperature programming technology was applied to to further improve the yield ofNMADA. The yield of NMADA achieved94%under the optimal temperatureprogramming technology when the amination proceeded at70℃for14h following110℃for8h with n(MA): n (CDA)=5:1.Undecylamine and N-methyl undecylamine were synthesised by decarboxylationof ADA and NMADA, and the products were characterized by FT-IR, ESI-MS and1H-NMR.The decarboxylation of different molecular forms of ADA and NMADA with water as reaction medium were explored. The decarboxylation of amphotericforms of ADA and NMADA with ethnol as reaction medium was also explored. Theresults indicate that amphoteric forms of ADA and NMADA can decarboxylate withwater or ethnol as reaction medium, the yield of fatty amine of by decarboxylation ofamphoteric forms of ADA and NMADA in ethnol is better than in water, the yield offatty amine by decarboxylation of amphoteric forms of NMADA is better than theyield of fatty amine by decarboxylation of amphoteric forms of ADA in ethnol.