Document Detail

Novel synthesis of N-alkoxycarbonyl amino acids and surfactant properties of their sodium salts.
MedLine Citation:
PMID:  20299766     Owner:  NLM     Status:  MEDLINE    
N-Acyl amino acids have been prepared from fatty acid chlorides and amino acids, but it may not be easy to vary the hydrophobic groups on the view point of availability. In this work, instead of acid halides, long alkyl chloroformates were prepared by the facile reaction of alcohols and triphosgene as an induction agent of hydrophobic group on amino acids. N-Alkoxycarbonyl amino acids were synthesized from alkyl chloroformate and amino acids under Sch?tten-Baumann reaction condition with some modification. Surfactant properties of their sodium salts were studied by surface tension measurements, dynamic light scattering and foaming test, and compared with those of N-acyl amino acids. Sodium salts of N-alkoxycarbonyl amino acids showed an excellent surface tension lowering ability comparable to N-acyl amino acids, and they also exhibited good foaming ability and stability.
Tokuzo Kawase; Yukie Nishioka; Tatsuo Oida
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  Journal of oleo science     Volume:  59     ISSN:  1347-3352     ISO Abbreviation:  J Oleo Sci     Publication Date:  2010  
Date Detail:
Created Date:  2010-03-19     Completed Date:  2010-06-22     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101175339     Medline TA:  J Oleo Sci     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  191-201     Citation Subset:  IM    
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Kyoto 606-8585, Japan.
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MeSH Terms
Amino Acids / chemical synthesis*
Fatty Acids
Formic Acids
Organic Chemistry Processes
Phosgene / analogs & derivatives
Surface Tension*
Surface-Active Agents / chemical synthesis*
Reg. No./Substance:
0/Alcohols; 0/Amino Acids; 0/Chlorides; 0/Fatty Acids; 0/Formic Acids; 0/Surface-Active Agents; 32315-10-9/bis(trichloromethyl) carbonate; 463-73-0/chlorocarbonic acid; 75-44-5/Phosgene

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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