PHYSICO-CHEMICAL PROPERTIES OF N,N-DI(2-HYDROXYETHYL)ALKYLAMINES
477
G × 106, mol/m2
chloride electrodes. In particular, the 0.1000 g
specimen was dissolved in 4 mL of KСl solution
(1 mol/L) and titrated with 0.1 mol/L aqueous HC1.
Content of N-alkyldiethanolamines and their рΚа
values were calculated as described in [13].
G × 106, mol/m2
Compounds solubility was determined by
gravimetry [23]. Their thermal stability was estimated
using the Q−1500D Paulig–Paulig–Erdei derivato-
graph (in air, at 20–600°С and 10 deg/min).
2
1
The compounds resistance towards acid hydrolysis
was studied by incubation of the 5 × 10–2 mol
specimen during 1 day at 20 and 60°С. The reaction
mixture was regularly sampled and analyzed by TLC
(Silufol plates, 1 : 2 chloroform–methanol, develop-
ment with 3% chloranil in toluene at 70°С, visual
inspection with the reference sample).
с, mmol/L
с, mmol/L
Fig. 2. Isotherm of C8H17N(CH2CH2OH)2 adsorption at the
water–air interphase boundary (1) and at 0.1 mol/L HCl–air
interphase boundary (2).
Surface tension at the interphase boundary between
the compounds solution (either in water or in 0.1 mol/L
HCl) and air was measured with stalagmometer [20].
Critical micelle concentration was determined
graphically as the kink of surface tension plot as func-
tion of concentration.
At lower concentrations, the surfactant adsorption
at the liquid surface occurred due to hydrogen
bonding. With increasing concentration, interaction of
the alkyl tails of the surface-adsorbed surfactant mole-
cules with micelles in solution was possible. Likely,
that was the reason for appearance of the maxima in
adsorption isotherms. Adsorption reached the limit at
sufficiently high surfactant concentration, when no
further growth of micelles in the solution was possible.
REFERENCES
1. Lange, K.R., Surfactants. A Practical Handbook,
Hanser Gardner Publications, 1999.
2. Taub, B., USA Patent 4014841, 1977.
3. Gernon, M.D. and Dowlingm, C.M.F., USA Patent
Appl. 0005463, 2006.
4. Gernon, M.D., USA Patent 7553882, 2009.
EXPERIMENTAL
Compounds I were prepared from diethanolamine
and the corresponding primary alkyl halogenides as
described in [22]. Liquid products were purified by
vacuum distillation. Solid compound I (R = C14Н29)
was purified by the reaction mixture washing with
hexane followed by repeated recrystallization (two or
three times) from hexane–ethyl acetate 2 : 1 mixture.
5. Del’ Ducha, V., Mazotti, V., and Stsialla, S., RF Patent
2168578, 2001.
6. Govoni, G. and Patronchini, D., RF Patent 2466144,
2012.
7. Gernon, M.D., Martyak, N.M., Dowling, C.M., and
Alford, D., USA Patent Appl. 0209798, 2008.
8. Govoni, G. and Patronchini, D., RF Patent 2124026,
1998.
9. Titkov, S.N., Panteleeva, N.N., Konoplev, E.V.,
Al’zhev, I.A., and Groshnikova, G.V., RF Patent
2278739 S 2, 2006.
10. Stefanovic, G. and Ciric, J., Rec. Trav. Shim., 1954,
vol. 73, no. 5, p. 401.
11. Szarvasi, E., Eur. J. Med. Chem., 1976, vol. 11, no. 2,
Purity and identity of the products was confirmed
by IR, 1Н NMR, and elemental analysis data. 1H NMR
spectra were recorded using the MERCURY plus 300
spectrometer (CDCl3 solution). IR spectra were re-
corded using the IFS 66 Bruker spectrometer (Vaseline
oil suspension, KBr window, 100 scans at 1 cm–1).
Elemental analysis was performed using the
CHNS−932 analyzer (LECO Corporation).
p. 115.
12. Limanov, V.E. and Myazina, N.V., Zh. Prikl. Khim.,
Content of the main component in the samples
(>98%) was determined by potentiomentric titration
using the I–160M ionomer with glass and silver
1988, vol. 61, no. 10, p. 2365.
13. Radushev, A.V., Koltashev, D.V., Nasrtdinova, T.Yu.,
Shcherban’, M.G., Chekanova, L.G., and Plotniko-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014