A route to simple nonionic surfactants

Figures & data

Scheme 1. Reaction scheme showing the acylation reaction of primary amines with ethylene carbonate.

Table 1. Yields and analyses of surfactants–carbamates

Surfactant	Yield, %	M.p.,°C	Analyses, %*			^1H-NMR spectra, δ, ppm**			IR spectra, cm^−1***
			C	H	N	CH2OC	CH2OH	CH2N	νC=O	νN–H	δN–H
3a	79.8	78–80	$\frac{69.46}{69.25}$	$\frac{12.16}{11.93}$	$\frac{4.28}{4.25}$	4.20	3.80	3.17	1,685	3,353	1,541
3b	79.1	58–60	$\frac{66.01}{65.89}$	$\frac{11.60}{11.43}$	$\frac{5.14}{5.12}$	4.20	3.80	3.17	1,685	3,298	1,568
3c	79.0	45–46	$\frac{60.75}{60.80}$	$\frac{10.84}{10.67}$	$\frac{6.26}{6.45}$	4.19	3.79	3.16	1,699	3,311	1,551

^* Found results vs. calculated data.

^** Determined in CDCl₃ solution on Varian 400 NMR spectrometer, internal standard TMS.

^*** Registered in KBr tablet on the instrument Perkin Elmer Spectrum One.

Table 2. The behavior of surfactants–carbamates in water solutions

Surfactant	Surface tension, mN/cm*	cmc, mg/L
3a	42.1	11.9
3b	38.5	9.8
3c	32.5	8.4

^* Determined by the du Noüy ring method at 25°C at concentrations of surfactants 100 mg/L.