A convenient synthesis of quaternary ammonium gemini surfactants from long-chain alkyldimethylamines and epichlorohydrin

Synlett

Volumn , Issue 11, 2002, Pages 1811-1814

  Ricci, C G ^a   Cabrera, M I ^a   Luna, J A ^a   Grau, R J ^a  

^a UNIVERSIDAD NACIONAL DEL LITORAL   (Argentina)

Author keywords

Bis quaternary ammonium compounds; Epichlorohydrin; Gemini surfactants; Micellar system; Quaternization

Indexed keywords

ALCOHOL; AMINE; DIMETHYLAMINE; EPICHLOROHYDRIN; QUATERNARY AMMONIUM DERIVATIVE; SURFACTANT; WATER;

AQUEOUS SOLUTION; ARTICLE; MICELLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036423025     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34876     Document Type: Article

References (32)

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25. 9
26. (a) Simultaneous determination of mono- and bis-quaternary salts 4a-c and 5a-c from crudes of reaction by ion-exchange HPLC was not successful due to the unacceptable reproducibility. We overcame these difficulties by combining reversed-phase ion-pair HPLC using sodium p-toluen-sulfonate as UV-absorbing ion-pair reagent, and UV quantification of quaternary ammonium-bromophenol blue complexes extracted with chloroform from a mixture of a suitable aliquot of the reaction mixture in alkaline solution (10% sodium carbonate) and bromophenol blue (0.001 N). After comparison with standard mixtures, the experimental error was found to be about 2-3%.
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29. A typical procedure was as follows. A stirred solution of N,N-dimethyloctylamine(1a) (1.26 g, 8 mmol) and N,N-dimethyloctylamine hydrochloride (3a, 0.78g, 4 mmol) in of ethanol-water (80:20, 5 mL) mixture was heated until complete dissolution at 50°C. The epichlorohydrin (2, 0.37g, 4 mmol) was then added under vigorous agitation. After being stirred for 8-10 hours, the reaction mixture was immediately cooled and the solvent was removed under vacuum at room temperature. The residue was washed with acetone, and the quaternary ammonium salts were isolated by recrystallization from acetone. It afforded the mono-quaternary ammonium salt 4a (0.96 g, 84% isolated yield, 90% analytical yield). The bis-quaternary ammonium salt 5a (1.53 g, 87% isolated yield, 92% analytical yield), was obtained by performing the reaction with the same amount of reagents and solvent, at 80°C.
30. 9 There was no problem to separate the surfactants 5a-c from the excess of 3a-c because these amine hydrochlorides are soluble in cold acetone, while the bis-quaternary ammonium salts are insoluble ones.
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