Allylacetylenes and their derivatives as inhibitors of steel corrosion in sulfuric acid

Article abstract of DOI:10.1134/S1070427206110176

New functionalized derivatives of allylacetylenes were prepared, and their ability to inhibit corrosion of St.3 low-carbon steel in 5 N sulfuric acid was studied. The effectiveness of inhibition of steel corrosion was studied in relation to the structure of acetylene derivatives, their concentration, and temperature of acidic medium.

Full text of DOI:10.1134/S1070427206110176

ISSN 1070-4272, Russian Journal of Applied Chemistry, 2006, Vol. 79, No. 11, pp. 1829 1834. Pleiades Publishing, Inc., 2006.
Original Russian Text M.G. Veliev, N.M. Agaev, M.I. Shatirova, A.Z. Chalabieva, G.D. Geidarova, S.S. Alieva, 2006, published in Zhurnal Prikladnoi
Khimii, 2006, Vol. 79, No. 11, pp. 1848 1854.
APPLIED ELECTROCHEMISTRY
AND CORROSION PROTECTION OF METALS
Allylacetylenes and Their Derivatives as Inhibitors
of Steel Corrosion in Sulfuric Acid
M. G. Veliev, N. M. Agaev, M. I. Shatirova, A. Z. Chalabieva,
G. D. Geidarova, and S. S. Alieva
Institute of Polymeric Materials, Azerbaijan National Academy of Sciences, Sumgait, Azerbaijan
Received August 3, 2005; in final form, March 2006
Abstract New functionalized derivatives of allylacetylenes were prepared, and their ability to inhibit corro-
sion of St.3 low-carbon steel in 5 N sulfuric acid was studied. The effectiveness of inhibition of steel corrosion
was studied in relation to the structure of acetylene derivatives, their concentration, and temperature of acidic
medium.
DOI: 10.1134/S1070427206110176
Functionalized unsaturated compounds are efficient
inhibitors of the steel acid corrosion [1 4]. Acetylene
derivatives strongly decelerate corrosion of steel in
hydrochloric acid [5 9]. The multiple bonds with
where X = R = H (I); X = H, R = CH (II); X = CH ,
3 3
R = H (III); X = R = CH (IV); X = Cl, R = H (V);
3
X = Cl, R = CH (VI).
3
The other functionalized allylacetylene derivatives
VII XXII were prepared from appropriate alcohols
I VI in accordance with procedures given in [10 12]
mobile
electrons determine high adsorption and
protective properties of acetylene compounds. It was
found that inhibition of the acid corrosion of steel
with allylacetylenes only slightly depends on the
nature of functional groups and substituents at un-
saturated bonds; the decisive effect is exerted by
acetylene and ethylene bonds.
(
Scheme 1), where X = R = H (VII), X = CH , R =
3
H (VIII, XI, XIV, XVII, XIX; X) = Cl, R = H (IX);
X = Cl, R = CH (X); X = R = CH (XII, XV, XVIII,
XX, XXI); X = H, R = CH (XIII, XVI, and XXII).
3
3
3
The physicochemical properties of compounds I
XXII are listed in Table 1. The structure and composi-
tion of the resulting compounds were studied by thin-
layer (TLC) and gas liquid (GLC) chromatography
Proceeding with studies of high-performance acid
inhibitors, in this work we prepared new allylacetyl-
enes and their derivatives and studied their inhibition
properties in 5 M sulfuric acid in relation to the struc-
ture (nature of substituents).
1
and by IR and H NMR spectroscopy (Table 2) [10,
1
1, 13].
Previously [10, 11] we studied the reaction of alke-
nyl halides with monosubstituted primary and tertiary
acetylenic alcohols in the presence of EtMgBr/CuCl
As seen from Scheme 1, the resulting allylacet-
ylenes can be divided in two groups: (a) primary and
tertiary alcohols of allylacetylene series and (b) ethers
and esters of allylacetylene compounds, also contain-
ing functional groups.
and NH Cl/CuCl, which are not universal reagents for
4
preparing the corresponding allylacetylenic alcohols in
a high yield. In this study, allylacetylenic alcohols
I VI were prepared by reaction of alkenyl halides
with the corresponding monosubstituted acetylenyl-
carbinols in dimethylformamide (DMF) in the pres-
ence of copper iodide, triethylamine (TEA), and
potassium carbonate:
When choosing the inhibitor structure, we took into
account the fact that multiple (double and especially
triple) bonds and functional groups [OH, OCOCH3,
OCH(OC H )CH ] provide efficient adsorption of
2
5
3
the compounds on the steel surface with the formation
of a protective film decelerating the corrosion.
R
TEA,CuI,
K CO
X
X
R
R
2
3
+
H
EXPERIMENTAL
OH
OH,
Cl
R
The IR spectra were recorded on a UR-20 spectro-
photometer in the 4000 400 cm 1 range (thin
I VI
1829

1
830
VELIEV et al.
Table 1. Properties of allylacetylenes and their derivatives I XXII
Found, %
Calculated, %
Com- Yield,
bp,
C
2
0
20
n
d
Formula
D
4
pound
%
(P, mm Hg)
C
H
Cl(N)
C
H
Cl(N)
I
II
III
IV
V
VI
VII
VIII
IX
74.2
80.7
82.9
80 81 (18)
70 71 (12)
92 94 (13)
1.4762 0.9373
1.4596 0.8997
1.4765 0.9284
1.4625 0.8839
1.4820 1.0680
1.4770 1.0428
1.4540 0.9769
1.4590 0.9700
1.4720 1.1209
1.4660 1.0659
1.4591 0.9287
1.4572 0.9075
1.4767 1.0445
1.4894 1.0818
1.4780 1.0293
1.4841 0.9539
1.4820 0.9843
1.4665 0.9666
1.4878 0.9505
1.4674 0.9236
1.4556 0.9467
1.4584 0.9620
74.81
77.50
76.46
8.46
9.63
9.30
C H O
74.97
77.37
76.32
8.38
9.74
9.15
6
8
C H O
8 12
C H O
7 10
85.3 86.5 87 (13)
78.01 10.34
C H O
78.21 10.21
9
14
68.5
78.6
82.4
85.8
79.1
70.1
75.2
80.1
71 72 (0.5)
64 65 (0.5)
84 85 (10)
95 96 (10)
72 73 (0.5)
69 70 (0.5)
60 61 (1)
55.30
60.45
69.68
71.18
55.60
59.70
72.55
5.10 27.20 C H ClO
6.80 22.20 C H ClO
7.13
7.79
5.18 20.63 C H ClO
6.60 17.50 C H ClO
9.86
55.19
60.55
69.54
71.02
55.67
59.86
72.48
5.41
6.99
7.30
7.95
5.25
6.53
9.95
27.15
22.34
6
7
8 11
C H O
8 10
2
2
C H O
9
12
20.54
17.67
8
9
2
X
XI
10 13
C H O
11 18
2
2
2
XII
XIII
XIV
XV
XVI
XVII
XVIII
XIX
XX
XXI
XXII
58 59 (1)
74.30 10.35
C H O
74.24 10.54
1
3 22
78.8 115 116 (1)
63.2 122 123 (1)
67.1 123 124 (1.5)
85.2
66.4
78.2
82.2 145 146 (1.5)
66.6 124 125 (1.5)
72.1 104 105 (0.5)
61.22
59.19
62.39
73.40
72.19
74.31
70.04 10.32
71.69 10.75
71.20
70.68
7.80 16.51 C H ClO
7.43 17.60 C H ClO
8.19 15.55 C H ClO
8.92
8.55
9.15
60.97
59.26
62.46
73.30
72.26
74.19
70.19 10.44
71.80 10.84
71.39
70.55
7.90
7.46
8.30
8.94
8.49
9.33
16.36
17.49
15.36
1
1
17
2
2
2
1
0 15
1
2 19
78 79 (1)
98 99 (1.5)
86 87 (1)
C H O
11 16
2
2
2
C H O
1
0 14
C H O
1
2 18
6.00 C H NO
5.85
5.23
1
4 23
5.30 C H NO
1
6 28
9.71
9.29
C H O
9.59
9.30
1
5
24
3
3
76.1
89 90 (1)
C H O
14 22
Table 2. 1H NMR and IR data for I XXII
Com-
pound
1H NMR, , ppm
IR, , cm 1
V
5.20 s, 5.55 s (2H, CH =C), 3.10 s (2H, CH ), 4.05 s (2H, CH O), 630, 1395, 1650, 2230, 3100, 3350
2
2
2
3
.80 br.s (1H, OH)
VI
5.15 s, 5.45 s (2H, CH =C), 3.05 s (2H, CH ), 1.40 s [6H, (CH ) ], 650, 1400, 1645, 2225, 3010, 3400
2
2
3 2
3
.90 br.s (1H, OH)
VII
VIII
IX
4.90 5.43 m (2H, CH =C), 5.50 6.00 m (1H, C=CH), 2.85 3.05 m 875, 990, 1160, 1248, 1656, 1746, 2235,
2
(
2H, CH ), 4.50 4.70 m (2H, CH O), 2.00 s (3H, COCH )
3010
2
2
3
4.75 s, 4.90 s (2H, CH =C), 1.75 s (3H, CH ), 2.85 s (2H, CH ), 890, 910, 1175, 1645, 1740, 2240, 3100
2
3
2
4
.55 s (2H, CH O), 2.10 s (3H, COCH )
2
3
5.10 s, 5.60 s (2H, CH =C), 3.15 s (2H, CH ), 4.10 s (2H, CH O), 640, 1170, 1246, 1380, 1656, 1745, 2235,
2
2
2
2
.08 s (3H, COCH3)
3090
X
5.15 s, 5.80 s (2H, CH =C), 3.10 s (2H, CH ), 1.53s [6H, (CH ) ], 660, 1135, 1250, 1395, 1660, 1740, 2220,
2
2
3 2
1
.96 s (3H, COCH3)
3010
XI
4.70 s, 4.96 s (2H, CH =C), 1.80 s (3H, CH ), 2.72 s (2H, CH ), 885, 915, 1095, 1160, 1410, 1655, 2235,
2
3
2
4
.45 s (2H, CH O), 4.40 q (1H, OCH), 3.26 q (2H, OCH ), 1.15 d
2
2
(
3H, CH CH), 1.00 t (3H, CH CH )
3 3 2
XII
4.76 s, 4.87 s (2H, CH =C), 1.75 s (3H, CH ), 2.86 s (2H, CH ), 890, 920, 1100, 1175, 1645, 2240, 3100
2 3 2
1
.40 s [6H, (CH ) ], 4.42 q (1H, OCH), 3.30 q (2H, OCH ), 1.17 d
3 2 2
(
3H, CH CH), 1.05 t (3H, CH CH )
3 3 2
XIII
4.90 5.40 m (2H, CH =C), 5.60 6.10 m (1H, C=CH), 2.75
725, 880, 910, 1170, 1670, 2235, 3100,
2
3
.05 m (2H, CH ), 1.30 s [6H, (CH ) ], 3.30 3.70 m (4H, CH , 3400
2
3 2
2
CH Cl), 375 4.00 m (1H, CH O), 2.35 br.s (1H, OH)
2
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 79 No. 11 2006

ALLYLACETYLENES AND THEIR DERIVATIVES
1831
Table 2. (Contd.)
Com-
pound
1H NMR, , ppm
IR, , cm 1
XIV
XV
4.80 s, 4.95 s (2H, CH =C), 1.80 s (3H, CH ), 2.90 s (2H, 730, 885, 905, 1165, 1660, 2245, 3010,
2
3
CH ), 4.15 t (2H, CH O), 3.45 d (2H, CH Cl), 3.55 d (2H, OCH ), 3380
2
2
2
2
3
.90 m (1H, CHO), 3.10 br.s. (1H, OH)
4.85 s, 4.70 s (2H, CH =C), 1.70 s (3H, CH ), 2.75 s (2H, CH ), 726, 890, 990, 1170, 1665, 2230, 3100,
2
3
2
1
.36 s [6H, (CH ) ], 3.40, 3.55 m (4H, CH Cl, CH ), 3.65 m (1H, 3400
3 2 2 2
OCH), 3.15s (1H, OH)
4.86 5.38 m (2H, CH =C), 5.57 6.05 m (1H, C=CH), 2.70 3.05 m 880, 910, 950, 1180, 1248, 1660, 2235,
XVI
XVII
XVIII
XIX
XX
2
(
2H, CH ), 1.38 s [6H, (CH ) ], 3.65 3.80 m (2H, OCH ), 3010, 3065
2 3 2 2
2
.85 3.00 m (1H, CHO), 2.30 2.65 m (2H, CH2)
4.80 s, 4.95 s (2H, CH =C), 1.86 s (3H, CH ), 2.90 s (2H, OCH ), 885, 915, 950, 990, 1170, 1255, 1640,
2
3
2
4
2
.20 t (2H, CH O), 3.50 m (2H, CH ), 3.05 m (1H, OCH), 2225, 3010, 3065
.45 2.70 m (2H, OCH2)
2
2
4.70 s, 4.90 s (2H, CH =C), 1.70 s (3H, CH ), 2.86 s (2H, CH ), 890, 910, 953, 1167, 1250, 1645, 2210,
2
3
2
1
.30 s [6H, (CH ) ], 3.45 m (2H, CH ), 2.90 m
3060, 3100
3
2
2
(
1H, OCH), 2.30 2.65 m (2H, OCH2)
4.75 s, 4.86 s (2H, CH =C), 1.76 s (3H, CH ), 2.88 s (2H, CH ), 886, 990, 1180, 1650, 2230, 2785, 3010,
2
3
2
4
.10 t (2H, CH O), 3.20 3.60 m (1H, CH, 2H, CH ), 2.33 2.65 q 3400
2
2
[
6H, N(CH ) ], 1.36 s [6H, (CH ) ]
2 3 3 2
4.70 s, 4.95 s (2H, CH =C), 1.70 s (3H, CH ), 2.85 s (2H, CH ), 890, 985, 1160, 1655, 2240, 2786, 3100,
2
3
2
1
.35 s [6H, (CH ) ], 3.25 3.65 m (3H, CH, CH ), 2.30 2.60 q [6H, 3450
3 2 2
N(CH ) ], 1.30 s [6H, (CH ) ]
2
3
3 2
XXI
XXII
4.73 s, 4.92 s (2H, CH =C), 1.80 s (3H, CH ), 2.30 s (2H, CH ), 880, 915, 1045, 1175, 1650, 2230, 3100
.35 s [6H, (CH ) ], 3.30 3.65 m (2H, OCH ), 2.80 3.00 m (1H,
3 2 2
CHO), 2.40 2.70 m (2H, CH O), 1.38 s [6H, (CH ) ]
4.80 5.40 m (2H, CH =C), 5.55 6.00 m (1H, C=CH), 2.75 2.90 m 885, 990, 1050, 1150, 1640, 2235, 3010
2 3 2
1
2
3 2
2
(
2H, CH ), 1.32 s [6H, (CH ) ], 3.25 3.60 m (2H, OCH ), 2.95
2 3 2 2
3
.15 m (1H, CHO), 2.30 2.65 m (2H, CH O), 1.36 s [6H, (CH ) ]
2 3 2
Note: The data for compounds I IV, which are not included in the table, are given in [10].
layer). The 1H NMR spectra were recorded on a
Tesla BS-487 B spectrometer (80 MHz) in carbon
tetrachloride solutions using HMDS internal refer-
ence. The purity of the resulting compounds was con-
trolled by thin-layer chromatography using Silufol
UV-254 plates in various solvent mixtures and by
gas liquid chromatography on an LKhM-8 MD-5
device.
chloride) (0.1 mol) was added dropwise. The resulting
mixture was stirred for an additional 8 h at 50 55 C.
After cooling, the mixture was washed with water and
extracted with ether. The ether layer was separated,
dried with MgSO , and evaporated in a vacuum.
4
The yield of products I VI was 65 80%. The physi-
cochemical properties of the resulting compounds
were close to those of the compounds prepared by the
published procedure [10].
The physicochemical properties and spectra of
compounds I XXII are listed in Tables 1 and 2.
1-Acetoxy-5-hexen-2-yne VII. Acetic anhydride
(4.1 g, 0.04 mol) was added with stirring to a mixture
To prepare primary and tertiary allylacetylenic
of allylacetylenic alcohol I (2 g, 0.02 mol) and con-
centrated sulfuric acid (0.1 ml) at 6 9 C, and the
reaction mixture was left overnight. Then, the mixture
was stirred for 1.5 h on heating to 65 70 C. After
cooling, the reaction mixture was diluted with water,
alcohols I VI, dimethylformamide (100 ml), K CO3
2
(
1.5 g), CuI (9.5 g), and triethylamine (0.5 ml) were
placed in a three-necked flask and stirred for 15
0 min in a nitrogen flow at 50 C. Appropriate acetyl-
2
ene compound (propargyl alcohol or dimethylethynyl-
carbinol) (0.05 mol) was added, the reaction mixture
was stirred for 2 h, and then appropriate alkenyl
halide (allyl chloride, 2,3-dichloropropene, methallyl
neutralized with K CO , and extracted with ether.
2
3
The ether layer was dried (MgSO ) and evaporated in
4
a vacuum to yield compound VII.
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 79 No. 11 2006

1
832
VELIEV et al.
Scheme 1.
VII X
XI, XII
I VI
XIII XV
XVI XVIII
XXI, XXII
XIX, XX
Compounds VIII X were prepared by similar
procedures using alcohols III, V, and VI.
ide etherate (0.1 ml). The reaction mixture was stirred
for 4 h at 25 C, and compound XIII was isolated by
vacuum distillation.
2-Methyl-7-oxa-8-ethoxy-1-nonen-4-yne XI. Hy-
drochloric acid (33%, 0.3 ml) was added with stirring
at 11 C to a mixture of allylacetylenic alcohol III
Chlorohydrins XIV and XV were prepared by
similar procedures from alcohols III and IV.
(0.06 mol) and vinyl ethyl ether (0.06 mol). The flask
1
-(1,1-Dimethyl-5-hexen-2-ynyloxy)-2,3-epoxy-
was intermittently shaken; in so doing, the tempera-
ture of the reaction mixture increased to 42 C. The
reaction mixture was left overnight. Then, the reaction
mixture was neutralized and extracted with ether.
The ether layer was dried (K CO ), the solvent was
propane XVI. Powdered KOH (8.4 g, 0.15 mol) was
added with stirring at 8 10 C to a solution of chloro-
hydrin XIII (10.8 g, 0.05 mol) in ether (60 ml).
The reaction mixture was stirred for 3 h at 12 14 C.
After common work-up and removal of the solvent,
compound XVI was isolated by vacuum distillation.
2
3
evaporated in a vacuum, and compound XI was iso-
lated by vacuum sublimation.
Epoxides XVII, XVIII were prepared similarly
from chlorohydrins XIV and XV.
Acetal XII was prepared by a similar procedure
using alcohol IV.
3
-Chloro-1-(1,1-dimethyl-5-hexen-2-ynyloxy)-
1-(5-Methyl-5-hexen-2-ynyloxy)-3-diethylamino-
propan-2-ol XIX. A mixture containing epoxide
XVII (3 g, 0.018 mol) and diethylamine (6.5 g,
0.5 mol) was stirred in the presence of water (2 ml)
propan-2-ol XIII. Epichlorohydrin (4 g, 0.043 mol)
was added with stirring at 0 5 C to allylacetylenic
alcohol II (12.4 g, 0.1 mol) containing boron trifluor-
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 79 No. 11 2006

ALLYLACETYLENES AND THEIR DERIVATIVES
1833
Table 3. Allylacetylene inhibitors of steel corrosion in 5 M H SO4
2
Inhibitor
Corrosion rate, g m 2 h 1
60
Degree of corrosion protection, %
Compound concentration,
1
g l
40
80
40
60
80
I
0.5
.0
0.5
.0
0.5
.0
0.5
.0
0.5
.0
0.5
.0
0.5
.0
0.5
.0
0.5
.0
0.5
.0
5.7
3.1
5.7
3.8
6.3
4.2
5.3
1.9
3.3
2.4
0.3
0.2
1.35
2.0
1.34
2.2
3.8
2.4
11.4
9.1
8.4
5.3
11.4
9.7
17.5
8.6
10.4
5.5
5.3
1.1
1.3
0.6
21.0
3.8
3.8
2.4
7.9
4.5
14.0
10.6
86.2
92.5
86.3
90.8
84.8
90.1
95.4
91.0
92.6
96.2
99.2
99.4
96.7
95.1
96.8
93.9
93.1
96.7
88.9
94.6
93.3
94.6
72.7
85.7
80.4
87.2
91.0
96.8
92.4
97.4
99.3
99.7
98.0
98.4
95.8
97.9
97.9
98.9
94.0
96.0
98.7
99.2
98.3
98.5
97.4
98.7
98.4
99.2
99.2
98.8
99.8
99.9
98.0
99.7
93.1
96.7
98.8
99.6
97.2
98.4
1
III
46.5
24.3
33.4
21.7
13.9
5.4
13.0
4.7
1.1
1
V
1
VII
VIII
XI
1
1
1
0.6
XII
XIX
XX
XXI
3.3
2.6
6.2
3.6
3.3
2.1
10.3
5.0
1
1
1
4.36
2.60
1
for 8 h at 50 C, then dioxane (about 10 ml) was added
to obtain the homogeneous mixture; in so doing, the
temperature of the reaction mixture increased. The
mixture was heated at 40 C for 3 h. Then it was ex-
tracted with ether and the ether layer was dried
The inhibition effect of compounds was studied by
gravimetric procedure simulating the conditions of
acidic etching of steel and rolled metal. Before ex-
periments, the specimens (30 20 3 mm) were
cleaned on a polishing device with rubber discs, de-
greased with acetone, and stored for 1 day in a desic-
(
K CO ). The solvent was removed in a vacuum and
2 3
1
compound XIX was isolated by vacuum distillation.
cator. The inhibitor concentration was 0.5 1.0 g l ;
the required temperature of the acid medium of 40,
Amino alcohol XX was prepared similarly from
epoxide XVIII.
6
0, or 80 C was maintained with a thermostat. The
experimental results listed in Table 3 show that all
the above compounds are highly effective inhibitors of
steel corrosion in sulfuric acid.
2
,2-Dimetyl-4-(3,3,7-trimethyl-2-oxo-7-octen-
4
0
0
0
-ynyl)-1,3-dioxolane XXI. Epoxide XVI (1.8 g,
.01 mol) was added to a mixture of acetone (8,1 g,
.14 mol) containing boron trifluoride etherate (1.8 g,
.01 mol); in so doing, the temperature of the reaction
Along with studying the protective properties of
compounds, we also tried to evaluate the correlation
between the structure of organic compounds and their
inhibiting performance and to determine the role of
various functional groups in the total protection effect.
mixture increased. After storage for 24 h, the reaction
mixture was treated with a saturated aqueous solution
of K CO , and the organic layer was separated and
2
3
dried (MgSO ). The solvent was removed in a vacuum
4
As seen, all the allylacetylenes studied exhibit pro-
nounced activity in inhibition of the acid corrosion of
steel. The degree of steel corrosion protection Z is
84 99%.
and 1,3-dioxolane XXI was isolated by vacuum dis-
tillation.
1,3-Dioxolane XXII was prepared similarly from
epoxide XVIII.
The compounds with normal structure with a ter-
minal alcohol group I, III, and V are highly effective
inhibitors. Substitution of the hydrogen atoms with
chlorine atom and methyl groups slightly decreases
the inhibiting performance of compounds V and III as
Among all the allyl derivatives prepared, ten com-
pounds (namely, I, III, V, VII, VIII, XI, XII, XIX
XXI) were studied as inhibitors of the acid corrosion
of steel in 5 N H SO .
2
4
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1
834
VELIEV et al.
compared to I. Allylacetylenes VII and VIII with
a terminal acetoxy group are also effective inhibitors.
Addition of the methylene group at the double bond
enhances the inhibition properties at 40 and 60 C, but
Z remains almost unchanged at 80 C.
in 5 N sulfuric acid. The inhibition effect is primarily
determined by the presence of double and triple bonds
and is virtually independent of the nature of functional
groups.
(3) With increasing temperature of the reaction
Substitution of two hydrogen atoms with methyl
groups (acetals XI, XII) slightly decreases the inhibit-
ing performance of allylacetylenes. The protective
effectiveness of amino alcohols XIX and XX is
ambiguous.
mixture and concentration of the inhibitor, the protec-
tion effect increases.
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1
2
. Rozenfel’d, I.L., Ingibitory korrozii (Corrosion In-
hibitors), Moscow: Khimiya, 1977.
. Podobaev, N.I. and Avdeev, Ya.G., Zashch. Met.,
On the whole, our experimental results suggest that
functionalized allylacetylenes are highly effective
inhibitors of the acid corrosion of steel; with increas-
ing concentration of inhibitors their protection effect
increases.
2
002, vol. 38, no. 1, pp. 51 56.
3. Kukharev, B.F., Stankevich, V.K., Klimenko, G.R.,
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The performance of inhibitors increases with in-
creasing temperature of the corrosion medium (es-
pecially at 80 C), which is probably due to the activa-
tion of chemisorption of the particles and molecular
fragments on the metal surface. On substitution of
methyl groups for hydrogen atoms, the structure of
inhibitors becomes more branched, which hinders
their adsorption on the metal surface and thus ordering
in the resulting protective film. We assumed that the
protection effect of allylacetylenes as inhibitors of
the acid corrosion of steel is due to the -electron
interaction of the double and triple bonds with metal,
resulting in the formation of chemisorption bonds
at elevated temperatures. The contribution of the other
fragments to corrosion inhibition is not decisive,
because the overall inhibition effect is extremely high.
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. RF Patent 2056406.
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CONCLUSIONS
(
1) Methods were developed for preparing primary
Azerb. Khim. Zh., 2003, no. 3, pp. 41 46.
and tertiary allylacetylenic alcohols in high yields by
the reaction of alkenyl halides with the corresponding
monosubstituted acetylenic alcohols in the presence of
copper(I) iodide, triethylamine, and potassium carbo-
nate in dimethylformamide.
2. Veliev, M.G., Shatirova, M.I., and Nadirova, M.I.,
Abstracts of Papers, 6-e soveshchanie po khimiche-
skim reaktivam (6th Meet. on Chemical Reagents),
Baku, October 5 9, 1993, p. 80.
3. Gordon, A.J. and Ford, R.A., The Chemist’s Compa-
nion. A Handbook of Practical Data, Techniques and
References, New York: Wiley Interscience, 1972.
1
(
2) A series of functionalized allylacetylenes pre-
pared are highly effective inhibitors of steel corrosion
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