N-十二烷基葡萄糖胺型表面活性剂的合成

以n(葡萄糖):n(十二胺)=1:1.3合成了中间体N-十二烷基葡萄糖亚胺。中间体在35～45℃,压力为3.5MPa,Raney-Ni作催化剂条件下高压催化加氢合成了N-十二烷基葡萄糖胺,纯化后产率为55.7%;中间体在氧化剂H2O2和缓冲剂NaHCO3存在下,N2环境0～5℃反应3h后,55℃无水条件下反应20h合成了硝酮类化合物N-氧自由基-N-十二烷基葡萄糖亚胺,纯化后产率为60.2%。通过IR,元素分析和1HNMR对产品和中间体进行了结构表征。测定了N-十二烷基葡萄糖胺和N-氧自由基-N-十二烷基葡萄糖亚胺对钙、镁离子的键合能力,分别为157.40mgCaO.g-1、252.30mgMgO.g-1和154.75mgCaO.g-1、283.4mgMgO.g-1。考察了两者的生物降解性能,在10d内降解度分别为96.1%、98.5%,达到了欧盟议会和欧盟委员会关于洗涤剂的(EC)No648/2004法规对表面活性剂生物降解性的要求,属于易降解表面活性剂。

Synthesis of N-Alkylglucosamine Surfactants

The intermediate N-dodecylglucosimine was synthesized using glucose and dodecylamine in molar ratio 1∶1.3.Then,catalyzed by Raney-Ni,the intermediate was hydrogenated at 35～45 ℃ under 3.5 MPa.The yield of N-dodecylglucosamine after purification was 55.7%.The intermediate was treated with oxidizing agent H2O2 and buffering agent NaHCO3 under the protection of N2.The reaction temperature should be controlled between 0～5 ℃ for 3 h,then controlled bellow 55 ℃ for 20 h in the anhydrous condition.The yield of oxidized N-dodecylglucosimine nitrone after purification was 60.2%.Structures of the target products and the key intermediate were characterized with IR,1HNMR and elementary analysis.The capability of N-dodecylglucosamine and N-dodecylglucosimine nitrone for complexometry of calcium ion and magnesium ion was determined as 57.40 mg CaO·g-1,252.30 mg MgO·g-1 and 154.75 mg CaO·g-1,283.4mg MgO·g-1,respectively.The biodegradability of two target products were 96.1% and 98.5%,respectively.Such results meet the requirement of regulation(EC) No 648/2004 of the European Parliament and of the Council of 31 March 2004 on Detergents,and these surfactants are all belong to easily biodegradable surfactants.