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Synthesis and Properties of N ‐Alkyl– N , N ‐Dimethyl‐ N ‐( o ‐Hydroxymethyl)Benzylammonium Chlorides
Author(s) -
Guo Xiangfeng,
Zhang Yingying,
Jia Lihua,
Liu Yanyan,
Zhu Zhanbo,
Zhang Yu,
Yang Rui
Publication year - 2015
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-015-1706-6
Subject(s) - chemistry , hydroxymethyl , alkyl , medicinal chemistry , amine gas treating , proton nmr , organic chemistry
A series of N ‐alkyl– N , N ‐dimethyl‐ N ‐( o ‐hydroxymethyl)benzylammonium chlorides surfactants (DHBA‐ m ) were synthesized using o ‐chloromethylbenzyl alcohol and N ‐alkyl– N , N ‐dimethyl tertiary amine as raw materials. The structure of the products was confirmed by FT‐IR, 1 H NMR, 13 C NMR and MS. DHBA‐ m surfactants exhibit low Krafft points and high surface activities. The process of micellization of DHBA‐ m is spontaneous, exothermic, and entropy‐driven. The hydroxymethyl substitution increases hydrophobicity of DHBA‐ m , thus making micellization more favorable compared with that of N ‐dodecyl– N , N ‐dimethyl‐ N ‐benzylammonium chlorides (DDBAC‐ m ). The bactericidal activity of DHBA‐ m is stronger on E. coli than that of DDBAC‐12, and DHBA‐16 shows strong bactericidal activity on Salmonella, S. aureus , and Streptococcus .