ANTICORROSION PROPERTIES OF PRODUCTS
1667
To estimate inhibiting properties of initial vinyl
ether of amino alcohol I and compounds IV and VI
obtained from it, we have studied their effect on the
corrosion of St.20 steel in 20% hydrochloric acid. The
rate of metal dissolution was determined by a
gravimetric method using 2×20×6 mm steel samples
according to GOST 9.505-86 at 20°С and exposure
time of 3 h. At the concentration of compounds I and
IV 10–2 M and of compound VI 3.33×10–3 M the
following protective effect Z (%) was obtained: 97.5
(IV), 94.4 (VI), and 34.9 (I). Thus, it has been shown
that though N-(2-vinyloxyethyl)-1,2-ethylenediamine
(I) itself does not inhibit the acid corrosion process, the
products of its condensation with carbonyl compounds
IV and VI possess a good protective effect. It shows
searching for new corrosion inhibitors among such
compounds is promising.
N,N',N"-Tris-[2-(2-vinyloxyethyl)aminoethyl]-
hexahydro-1,3,5-triazine (VI). Similarly to the
previous synthesis from 25.6 g (90%) of compound VI,
bp 175–178°С (3 mm Hg), d420 1.0218, nD20 4960, was
obtained from 26 g (0.2 mol) of N-(2-vinyloxyethyl)-
1,2-ethylenediamineа (I) and 6 g (0.2 mol) of para-
formaldehyde (III). IR spectrum, ν, cm–1: 1605, 1625,
3025, 3075, 3110, 3280. 1Н NMR spectrum, δ, ppm (J,
3
3
Hz): 6.43 d.d (OCH=C, 1H, Jcis 6.9, Jtrans 14.3), 4.10
2
3
d.d (trans-CH=C, 1H, Jhem 1.8, Jtrans 14.3), 3.93 d.d
2
3
(cis-CH=C, 1H, Jhem 1.8, Jcis 6.9), 3.44 s(NCH2N,
2H), 3.73 t (ОCH2, 2H, 3J 5.6), 3.01 t (NHCH2CH2N,
3
3
2H, J 7.1), 2.73 t (NHCH2CH2O, 2H, J 5.6), 2.62 t
(NHCH2CH2N, 2H, J 7.1), 1.83 br.s (NH, 1H). 13C
3
NMR spectrum, δ, ppm: 151.60 (OCH=), 86.34
(=CH2), 75.32 (NCH2N), 66.66 (OCH2), 53.54
(NCH2CH2NH), 52.69 (NCH2CH2NH), 50.39
(NHCH2CH2O). Found, %: C 59.33, Н 10.03, N 19.51.
C21H42N6O3. Calculated, %: C 59.12, Н 9.92, N 19.70.
EXPERIMENTAL
Commercial paraformaldehyde (purity of 98.3%)
and cyclohexanone purified by fractionation up to a
base material content of no less than 99.8% were used
for the synthesis. N-(2-Vinyloxyethyl)-1,2-ethylenedi-
amine was obtained by a procedure described in [6].
CONCLUSIONS
(1) It has been shown that products of N-(2-
vinyloxyethyl)-1,2-ethylenediamine condensation with
cyclohexanone and formaldehyde have the imine and
symmetrical triazine structures, respectively.
N-(2-Vinyloxyethyl)-N'-cyclohexylidene-1,2-ethyl-
enediamine (IV). A mixture of 26 g (0.2 mol) of N-
(2) In the case of steel acid corrosion the protective
effect N-(2-vinyloxyethyl)-N'-cyclohexylidene-1,2-ethyl-
enediamine and N,N',N"-tris-[2-(2-vinyloxyethyl)amino-
ethyl]hexahydro-1,3,5-triazine is 94.4–97.5%.
(2-vinyloxyethyl)-1,2-ethylenediamine (I), 19.6
g
(0.2 mol) of cyclohexanone, and 100 ml of toluene
were boiled with a Dyne–Stark trap up to the termina-
tion of water separation. The reaction mixture was
cooled and distilled. Yield of compound IV 38.2 g
(91%), bp 119–121°С (3 mm Hg), nD20 1.500. IR spec-
trum, ν, cm–1: 1605, 1615, 1660, 3040, 3065, 3100,
REFERENCES
1
1. Rozenfel’d, I.L., Ingibitory korrozii (Corrosion
3285. Н NMR spectrum, δ, ppm (J, Hz): 6.44 d.d
Inhibitor), Moscow: Chemistry, 1977.
3
3
(OCH=C, 1H, Jcis 6.7, Jtrans 14.3), 4.13 d.d (trans-
CH=C, 1H, 2Jhem 1.8, 3Jtrans 14.3), 3.95 d.d (cis-CH=C,
1H, 2Jhem 1.8, 3Jcis 6.7), 3.73 t (ОCH2, 2H, 3J 6.1), 3.25
2. vanov, E.S., Ingibitory korrozii metallov v kislykh
sredakh (Corrosion Inhibitors of Metals in Acid Media),
Moscow: Metallurgiya, 1986.
3
br.s (NH, 1H), 3.01 t (=NCH2, 2Н, J 6.9), 2.86 t
3
3. Kukharev, B.F., Stankevich, V.K., and Klimenko, G.R.,
(=NCH2CH2, 2Н, 3J 6.9), 2.75 t (ОCH2CH2N, 2H, J
6.1), 1.30–1.80 m (C5H10, 10H). 13С NMR spectrum, δ,
ppm: 172.92 (N=С), 153.13 (OCH=), 87.80 (=CH2),
69.01 (OCH2), 52.69 (CH2N=), 49.88 (NHCH2·
CH2N=), 49.39 (OCH2CH2NH), 32.81 (CH2CH2·
CH2CH2CH2), 28.35 (sin-CN=СCH2CH2), 27.45 (anti-
CN=CCH2CH2), 25.11 (CH2CH2CH2CH2CH2). Found,
%: C 68.64, Н 10.62, N 13.17. C12H22N2O. Calculated,
%: C 68.53, Н 10.54, N 13.32.
Usp. Khim., 1995, vol. 64, no. 6, pp. 562–579.
4. Kukharev, B.F., Stankevich, V.K., Klimenko, G.R.,
et al., Zh. Prikl. Khim., 2000, vol. 73, pp. 161–163.
5. Riehl, M. and Laurent, P.A., Bull. Soc. Chim. France,
1969, no. 4, pp. 1223–1226.
6. Kukharev, B.F., Stankevich, V.K., Lobanova, N.A.,
et al., Zh. Org. Khim., 2007, vol. 43, no. 12, pp. 1872–
1873.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 83 No. 9 2010