CN110904459A - Lauric acid tetracyclic imidazoline corrosion inhibitor and preparation method thereof - Google Patents
Lauric acid tetracyclic imidazoline corrosion inhibitor and preparation method thereof Download PDFInfo
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- CN110904459A CN110904459A CN201911247533.9A CN201911247533A CN110904459A CN 110904459 A CN110904459 A CN 110904459A CN 201911247533 A CN201911247533 A CN 201911247533A CN 110904459 A CN110904459 A CN 110904459A
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Abstract
The invention discloses a lauric acid tetracyclic imidazoline corrosion inhibitor and a preparation method thereof, belonging to the technical field of corrosion inhibitor production. The invention prepares the lauric acid tetracyclic imidazoline corrosion inhibitor by heating sebacic acid and tetraethylenepentamine for reaction in the presence of xylene, then adding lauric acid into a reaction system, heating for amidation reaction, and heating again for cyclization reaction after the amidation reaction of the participation of the lauric acid. The lauric acid tetracyclic imidazoline corrosion inhibitor belongs to a green corrosion inhibitor, has low toxicity, environmental protection and good corrosion inhibition effect, has good fluidity at normal temperature, is slightly soluble in water, and is easily soluble in an organic solvent.
Description
Technical Field
The invention relates to the technical field of corrosion inhibitors, in particular to a lauric acid tetracyclic imidazoline corrosion inhibitor and a preparation method thereof.
Background
The imidazoline corrosion inhibitor is a green corrosion inhibitor commonly used in an acidification environment, and has the functions of inhibiting metal corrosion, slowing down corrosion rate and the like. The imidazoline corrosion inhibitor belongs to an adsorption film type corrosion inhibitor, and imidazoline molecules have polar groups and nonpolar groups. The polar group is mainly adsorbed on the metal surface by nitrogen element. The nonpolar group is mainly a hydrophobic group with a long carbon chain, and can form a layer of hydrophobic film between the metal and the solution, so that the corrosion of the metal surface can be prevented.
The imidazoline corrosion inhibitor is mainly prepared by synthesizing fatty acid, polyamine and other raw materials, and has one or more imidazoline rings in a chemical structural formula, wherein the imidazoline ring is a five-membered ring, and two nitrogen atoms can provide lone electron pairs to form coordination bonds with empty orbitals of iron atoms, so that the adsorption capacity between corrosion inhibitor molecules and metals is enhanced, and the corrosion inhibitor molecules are stably adsorbed on the metal surfaces.
There are generally two methods for synthesizing imidazolines: vacuum process and solvent process. The vacuum method is mainly used for removing water generated by amidation reaction and cyclization reaction by reducing pressure and raising temperature. The solvent method mainly uses toluene or xylene as a water carrying agent, can form an azeotrope with water, and has boiling points of 84.1 ℃ and 92.0 ℃ respectively so as to achieve the effect of removing water. At present, imidazoline corrosion inhibitors are widely synthesized by a solvent method, the reaction temperature is low, and the implementation is simpler compared with a vacuum method. The corrosion inhibitor evaluation method is more complete, and the common methods comprise a weight loss method, electrochemical measurement, a scanning electron microscope and the like.
Along with the gradual improvement of environmental protection consciousness of people, the research and development requirements of the corrosion inhibitor are also continuously improved. The corrosion inhibitor is required to have high-efficiency corrosion inhibition performance, environment-friendly raw materials and chemical reactions are adopted, and the product is low-toxicity or non-toxic. The imidazoline corrosion inhibitor is mainly characterized by low toxicity, economy and high efficiency. Therefore, the imidazoline corrosion inhibitor meets the requirement of a green high-efficiency corrosion inhibitor.
At present, most imidazoline corrosion inhibitors in China only have one or two imidazoline rings, and have the advantages of few adsorption sites, weak adsorption capacity and low corrosion inhibition effect. The polycyclic imidazoline molecule has two or more imidazoline rings, can be more effectively adsorbed on the metal surface due to more adsorption sites and strong activity, and also has two hydrophobic groups, so that a hydrophobic protective layer is formed on the metal surface to play a role in inhibiting corrosion. Therefore, the research on the polycyclic imidazoline corrosion inhibitor still has great research value.
Disclosure of Invention
The invention aims to provide a lauric acid tetracyclic imidazoline corrosion inhibitor and a preparation method thereof, and aims to solve the problem of poor corrosion inhibition effect of the existing imidazoline corrosion inhibitor.
The technical scheme for solving the technical problems is as follows:
a lauric acid tetracyclic imidazoline corrosion inhibitor has a molecular structural formula as follows:
according to the preparation method of the lauric acid tetracyclic imidazoline corrosion inhibitor, sebacic acid and tetraethylenepentamine are subjected to heating reaction in the presence of xylene, then lauric acid is added into a reaction system and heated for amidation reaction, and after the amidation reaction with participation of lauric acid is finished, heating is carried out again for cyclization reaction, so that the lauric acid tetracyclic imidazoline corrosion inhibitor is prepared.
The invention adopts sebacic acid as a basis for synthesizing the tetracyclic imidazoline corrosion inhibitor, and utilizes carboxylic acid groups at two ends of a molecule of the sebacic acid to respectively perform amidation reaction with fatty acid, thereby playing a role in connection for synthesizing the tetracyclic imidazoline corrosion inhibitor as a basis.
Carboxylic acid groups at two ends of sebacic acid are respectively subjected to amidation reaction with tetraethylenepentamine, so that the tetraethylenepentamine is connected to two ends of sebacic acid, then lauric acid is added to perform amidation reaction, and finally cyclization reaction is performed to synthesize the corrosion inhibitor with four imidazoline rings.
Further, in a preferred embodiment of the present invention, the preparation method comprises the following steps:
(1) dissolving 0.05-0.1 mol of sebacic acid in dimethylbenzene, heating to 80-100 ℃, adding 0.12-0.2 mol of tetraethylenepentamine, heating to 120-140 ℃, and reacting for 2.5-4 hours;
(2) cooling the product obtained in the step (1) to 80-100 ℃, adding 0.8-1.2 mol of lauric acid, heating to 140-160 ℃, and reacting for 2.5-3 h;
(3) and (3) heating the product obtained in the step (2) to 220-240 ℃ and reacting for 3-4 h to obtain the lauric acid tetracyclic imidazoline corrosion inhibitor.
In the step (1), the sebacic acid is dissolved in xylene and then undergoes a first amide ring reaction with tetraethylenepentamine, the xylene is used as a solvent to dissolve the sebacic acid on one hand, and can form an azeotrope with water generated in an amidation reaction on the other hand, the boiling point of the azeotrope is relatively reduced, and evaporation, condensation and separation of water are facilitated, so that the xylene is used as the solvent, and removal of water generated in the reaction process is facilitated. The temperature of the first heating reaction system is 80-100 ℃, the aim is to enable sebacic acid to be dissolved in dimethylbenzene more fully, the second heating temperature is 120-140 ℃ for reaction for 2.5-4 hours, the most suitable reaction condition is provided for the first amidation reaction, the reaction of sebacic acid and tetraethylenepentamine is enabled to be carried out fully, and water generated in the first amidation reaction can be removed.
In the step (2), cooling an amidated product obtained after the first amidation reaction, stopping the reaction in the step (1) by cooling, and then adding lauric acid for heating to carry out a second amidation reaction; by controlling the reaction conditions as follows: the reaction temperature is 140-160 ℃, the reaction time is 2.5-3 h, so that lauric acid is subjected to amidation reaction and gradually undergoes cyclization reaction towards imidazoline, and the water in a reaction system is removed favorably.
In step (3), the final cyclization reaction is carried out by raising the temperature to obtain the imidazoline corrosion inhibitor with four rings.
Further, in a preferred embodiment of the present invention, in the step (1), the amount of the xylene is 50 to 70 ml.
Further, in a preferred embodiment of the present invention, in the step (1), the temperature is raised to 130-140 ℃ after the tetraethylenepentamine is added.
Further, in a preferred embodiment of the present invention, in the step (3), the temperature of the product obtained in the step (2) is increased to 230-240 ℃.
The invention has the following beneficial effects:
the lauric acid tetracyclic imidazoline corrosion inhibitor provided by the invention has four imidazoline rings and a plurality of adsorption centers, and the N atom can provide a lone electron pair to form a coordination bond with an iron atom, so that corrosion inhibitor molecules can be better adsorbed on the metal surface, and the corrosion is prevented. The synthesized tetracyclic imidazoline is firstly prepared by adopting sebacic acid, utilizing the characteristic that two ends of the sebacic acid are respectively provided with a carboxylic acid, is connected with tetraethylenepentamine, and then is subjected to amidation reaction with lauric acid.
Compared with single-ring and double-ring lauric acid corrosion inhibitors, the lauric acid tetracyclic imidazoline corrosion inhibitor has better corrosion inhibition effect and better metal corrosion inhibition capability. The corrosion inhibitor with four imidazoline rings has stronger adsorption capacity, and can be better adsorbed on the metal surface.
The lauric acid tetracyclic imidazoline corrosion inhibitor belongs to a green corrosion inhibitor, has low toxicity, environmental protection and good corrosion inhibition effect, has good fluidity at normal temperature, is slightly soluble in water, is easily soluble in an organic solvent, and is a brown viscous liquid. The preparation method has the advantages of simple process, easily obtained raw materials, low raw material cost, short synthesis time and proper synthesis temperature.
Drawings
FIG. 1 is a diagram of the synthetic route to a preparation process according to an embodiment of the present invention;
FIG. 2 is a Nyquist plot of lauric acid bicyclic imidazoline corrosion inhibitor;
FIG. 3 is a Nyquist plot of a lauric acid tetracyclic imidazoline corrosion inhibitor of an embodiment of the present invention;
fig. 4 is an equivalent circuit diagram.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Referring to a synthesis scheme for preparing the lauric acid tetracyclic imidazoline corrosion inhibitor shown in fig. 1, sebacic acid and tetraethylenepentamine are subjected to amidation reaction in the presence of a solvent xylene to obtain sebacic acid and tetraethylenepentamine amination products; adding lauric acid, and carrying out amidation reaction again, wherein the amidation reaction is carried out on the lauric acid tetracyclic imidazoline; then, heating again for cyclization reaction, wherein the cyclization process is the cyclization of the lauric acid tetracyclic imidazoline, and finally the corrosion inhibitor with tetracyclic imidazoline is obtained.
The present application is further illustrated below with reference to examples.
Example 1:
a lauric acid tetracyclic imidazoline corrosion inhibitor comprises the following steps:
(1) dissolving 0.08mol of sebacic acid in dimethylbenzene, heating to 80 ℃, adding 0.2mol of tetraethylenepentamine, heating to 120 ℃ and reacting for 4 hours;
(2) cooling the product obtained in the step (1) to 80 ℃, then adding 0.8mol of lauric acid, and then heating to 160 ℃ for reaction for 2.5 h;
(3) and (3) heating the product obtained in the step (2) to 220 ℃ to react for 3.5h to obtain the lauric acid tetracyclic imidazoline corrosion inhibitor.
Example 2:
a lauric acid tetracyclic imidazoline corrosion inhibitor comprises the following steps:
(1) dissolving 0.1mol of sebacic acid in dimethylbenzene, heating to 100 ℃, adding 0.18mol of tetraethylenepentamine, heating to 130 ℃, and reacting for 3 hours;
(2) cooling the product obtained in the step (1) to 100 ℃, then adding 0.12mol of lauric acid, and heating to 150 ℃ for reaction for 3 h;
(3) and (3) heating the product obtained in the step (2) to 240 ℃ and reacting for 3h to obtain the lauric acid tetracyclic imidazoline corrosion inhibitor.
Example 3:
a lauric acid tetracyclic imidazoline corrosion inhibitor comprises the following steps:
(1) dissolving 0.05mol of sebacic acid in 50ml of dimethylbenzene, heating to 90 ℃, adding 0.12mol of tetraethylenepentamine, heating to 140 ℃ and reacting for 2.5 hours;
(2) cooling the product obtained in the step (1) to 90 ℃, then adding 0.1mol of lauric acid, and then heating to 140 ℃ for reaction for 2.5 h;
(3) and (3) heating the product obtained in the step (2) to 230 ℃ for reaction for 4h to obtain the lauric acid tetracyclic imidazoline corrosion inhibitor.
Example 4:
a lauric acid tetracyclic imidazoline corrosion inhibitor comprises the following steps:
(1) dissolving 0.05mol of sebacic acid in 50ml of dimethylbenzene, heating to 90 ℃, adding 0.12mol of tetraethylenepentamine, heating to 135 ℃ and reacting for 2.5 hours;
(2) cooling the product obtained in the step (1) to 90 ℃, then adding 0.1mol of lauric acid, and then heating to 140 ℃ for reaction for 2.5 h;
(3) and (3) heating the product obtained in the step (2) to 235 ℃ and reacting for 4h to obtain the lauric acid tetracyclic imidazoline corrosion inhibitor.
Experimental example 1:
the corrosion inhibitor prepared by the embodiment of the invention is added into an electrode system for electrochemical test according to the following method: the electrochemical workstation is CS310H, a three-electrode system is adopted in the test, the auxiliary electrode is a platinum electrode, the reference electrode is a saturated calomel electrode, and the working electrode is made of L360. The working electrode is sequentially polished by 600, 800, 1000 and 1200 meshes of abrasive paper, washed by absolute ethyl alcohol and finally dried for later use. AC impedance test frequency of 10-2～105Hz, amplitude of 10 mV. The experiment was carried out at 60 ℃ with 3.5% NaCl in saturated CO 2. The test was started after the open circuit potential had stabilized. Fitting data obtained by the alternating-current impedance spectrum through an equivalent circuit diagram, and calculating the corrosion inhibition rate, wherein the calculation formula is as follows:
in the formula IEEISCorrosion inhibition rate,%;
is a blank set of charge transfer resistances, Ω; rctThe resistance is the charge transfer resistance omega after the corrosion inhibitor is added;
the alternating current impedances of the lauric acid bicyclic imidazoline corrosion inhibitor and the lauric acid tetracyclic imidazoline corrosion inhibitor are shown in fig. 2 and fig. 3.
The fitting was performed using an equivalent circuit, which is shown in fig. 4.
The fitting data are shown in table 1 and table 2:
TABLE 1 lauric acid bicyclic imidazoline corrosion inhibitor impedance plot fitting data
| Blank space | 20 | 50 | 80 | 100 | 200 | |
| R1 | 4.066 | 4.134 | 4.483 | 4.578 | 5.204 | 4.628 |
| CPE,Y | 0.0004488 | 4.02E-04 | 0.0002463 | 1.51E-04 | 1.12E-04 | 1.17E-04 |
| CPE,n | 0.7958 | 0.8163 | 0.8858 | 0.8182 | 0.8653 | 0.831 |
| R2 | 134.9 | 186.1 | 660.9 | 602.3 | 1111 | 945.6 |
| IEEIS(％) | - | 27.51％ | 79.59％ | 77.60％ | 87.86％ | 85.73％ |
TABLE 2 lauric acid tetracyclic imidazoline corrosion inhibitor impedance plot fitting data
| Blank space | 20 | 50 | 80 | 100 | 200 | |
| Rs | 4.066 | 4.356 | 4.826 | 5.06 | 4.446 | 4.738 |
| CPE,Y | 0.0004488 | 2.66E-04 | 0.0002584 | 2.02E-04 | 1.08E-04 | 1.29E-04 |
| CPE,n | 0.7958 | 0.8083 | 0.7655 | 0.7649 | 0.8669 | 0.8222 |
| Rct | 134.9 | 357.3 | 773.5 | 1079 | 1330 | 1650 |
| IEEIS(％) | - | 62.24％ | 82.56％ | 87.50％ | 89.86％ | 91.82％ |
The data obtained by fitting are shown in the table, and the blank group without the corrosion inhibitor has smaller charge transfer resistance and can generate serious corrosion. After the lauric acid double-ring and lauric acid four-ring imidazoline corrosion inhibitor is added, the charge transfer resistance is obviously increased, which shows that the corrosion inhibiting effect is achieved. The corrosion inhibition rate can be seen that the lauric acid tetracyclic imidazoline corrosion inhibitor is obviously higher than the lauric acid bicyclic imidazoline corrosion inhibitor, particularly under the condition of low concentration, the corrosion inhibition rate of the 20ppm lauric acid bicyclic imidazoline corrosion inhibitor is 27.51%, the lauric acid tetracyclic imidazoline reaches 62.24%, and the corrosion inhibition effect is obviously improved. Therefore, the corrosion inhibition effect of the lauric acid tetracyclic imidazoline corrosion inhibitor disclosed by the embodiment of the invention is obviously better than that of the lauric acid bicyclic imidazoline corrosion inhibitor, and the economic benefit is higher.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (6)
1. The lauric acid tetracyclic imidazoline corrosion inhibitor is characterized by having a molecular structural formula as follows:
2. the preparation method of the lauric acid tetracyclic imidazoline corrosion inhibitor as claimed in claim 1, wherein the lauric acid tetracyclic imidazoline corrosion inhibitor is prepared by heating sebacic acid and tetraethylenepentamine in the presence of xylene for reaction, then adding lauric acid into the reaction system and heating for amidation reaction, and heating again for cyclization reaction after the amidation reaction in which lauric acid participates is finished.
3. The preparation method of the lauric acid tetracyclic imidazoline corrosion inhibitor according to claim 2, wherein the preparation method comprises the following steps:
(1) dissolving 0.05-0.1 mol of sebacic acid in dimethylbenzene, heating to 80-100 ℃, adding 0.12-0.2 mol of tetraethylenepentamine, heating to 120-140 ℃, and reacting for 2.5-4 hours;
(2) cooling the product obtained in the step (1) to 80-100 ℃, adding 0.8-1.2 mol of lauric acid, heating to 140-160 ℃, and reacting for 2.5-3 h;
(3) and (3) heating the product obtained in the step (2) to 220-240 ℃ and reacting for 3-4 h to obtain the lauric acid tetracyclic imidazoline corrosion inhibitor.
4. The preparation method of the lauric acid tetracyclic imidazoline corrosion inhibitor according to claim 3, wherein in the step (1), the addition amount of the xylene is 50-70 ml.
5. The preparation method of the lauric acid tetracyclic imidazoline corrosion inhibitor according to claim 3, wherein in the step (1), the temperature is increased to 130-140 ℃ after the tetraethylenepentamine is added.
6. The preparation method of the lauric acid tetracyclic imidazoline corrosion inhibitor according to any one of claims 3 to 5, wherein in the step (3), the temperature of the product obtained in the step (2) is raised to 230-240 ℃.
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| CN116023920A (en) * | 2022-11-11 | 2023-04-28 | 天津大港油田滨港集团博弘石油化工有限公司 | Environment-friendly tetracyclic imidazoline solid corrosion inhibitor and preparation method thereof |
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