CN110724959A - Preparation method and application of bromopropanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor - Google Patents
Preparation method and application of bromopropanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor Download PDFInfo
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- CN110724959A CN110724959A CN201910888920.4A CN201910888920A CN110724959A CN 110724959 A CN110724959 A CN 110724959A CN 201910888920 A CN201910888920 A CN 201910888920A CN 110724959 A CN110724959 A CN 110724959A
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- aminofluorene
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/146—Nitrogen-containing compounds containing a multiple nitrogen-to-carbon bond
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
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Abstract
The invention discloses a preparation method and application of a bromo-malondialdehyde-condensed 2-aminofluorene bis-Schiff base corrosion inhibitor. The bromomalonaldehyde 2-aminofluorene bis-Schiff base corrosion inhibitor is prepared by mixing a bromomalonaldehyde ethanol solution and a 2-aminofluorene ethanol solution for condensation reaction to obtain bromomalonaldehyde condensed 2-aminofluorene bis-Schiff base and then using water as a solvent. The bromopropanaldehyde-2-aminofluorene bis-Schiff base contains two functional groups with the carbon number = N, the adsorption effect of the bromopropanaldehyde-2-aminofluorene bis-Schiff base on the surface of carbon steel is enhanced, and the corrosion inhibitor can keep a high corrosion inhibition effect in circulating cooling water at a high temperature and in which a large amount of dissolved oxygen, chloride ions, sulfate ions and microorganisms exist.
Description
Technical Field
The invention belongs to the field of corrosion inhibitors, and particularly relates to a preparation method and application of a bromo-malondialdehyde condensed 2-aminofluorene bis-Schiff base corrosion inhibitor.
Background
The circulating cooling water is a large item of water used in industrial water, and in the industries of petrochemical industry, electric power, steel, metallurgy and the like, the consumption of the circulating cooling water accounts for 50-90% of the total water used by enterprises. Cooling water is continuously recycled in a circulating system, and due to the combined action of various factors such as water temperature rise, flow rate change, evaporation, concentration of various inorganic ions and organic substances, sunlight irradiation, wind and rain, dust and sundries entering of a cooling tower and a cooling water tank outdoors, and the structure and materials of equipment, a plurality of problems can be caused, for example, carbonate can be deposited on the heat transfer surface of a heat exchanger due to evaporation concentration of the circulating cooling water, so that scale adhesion is generated, and the heat transfer efficiency of the heat exchanger is reduced; oxygen dissolved in the circulating cooling water, chloride ions, sulfate ions and microorganisms can cause corrosion and perforation of the pipe wall of the equipment to form leakage, thereby influencing safe production. For scale adhesion, scale inhibitors such as polyphosphate, organic polyphosphonic acid and the like are generally added into circulating cooling water in production to destroy carbonate precipitates, which is the most widely used method for controlling scale formation at present. For equipment corrosion, corrosion inhibitors such as Mercaptobenzothiazole (MBT), Benzotriazole (BTA) and the like are usually added into circulating cooling water in production, and the corrosion inhibitors can form a corrosion inhibition film layer on the surface of metal so as to inhibit the corrosion of a corrosion medium to the metal. The corrosion inhibitor does not need to be added in too large amount, special equipment or pre-treatment of the equipment when in use, so the corrosion inhibitor is an economical and applicable metal corrosion protection technology. Therefore, the corrosion inhibitor is added to become a preferred method for preventing harmful ions from corroding the equipment pipeline by circulating cooling water.
The circulating cooling water has the characteristics of higher temperature, and larger existence amount of dissolved oxygen, existing chloride ions, sulfate ions, microorganisms and the like, so that the corrosion inhibitor and carbon steel have stronger binding force, and the corrosion inhibition effect can meet the industrial corrosion inhibition requirement. Compared with single Schiff base, the structure of the bis-Schiff base prepared by the invention contains two-C-N-groups, and more heteroatoms such as O, N, S can be introduced into the Schiff base structure, so that the bis-Schiff base has more active sites and stronger adsorption capacity on the surface of carbon steel, and thus the bis-Schiff base is expected to be an ideal corrosion inhibitor used in circulating cooling water.
Disclosure of Invention
The invention aims to provide a preparation method and application of a bromopropanediamyl 2-aminofluorene bis-Schiff base corrosion inhibitor. The corrosion inhibitor can keep a high corrosion inhibition effect in circulating cooling water with high temperature and a large amount of dissolved oxygen, chloride ions, sulfate ions and microorganisms.
The preparation method of the bromopropanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor comprises the following specific steps:
(1) 0.3987g of 2-aminofluorene and 0.1510g of bromomalondialdehyde are respectively weighed and respectively dissolved in 15mL of absolute ethanol to prepare a 2-aminofluorene ethanol solution and a bromomalondialdehyde ethanol solution; placing a 2-aminofluorene ethanol solution into a 50mL three-neck flask, adding 3 drops of acetic acid, adding a bromomalondialdehyde ethanol solution, placing the three-neck flask into a constant-temperature water bath kettle, setting the temperature at 45 ℃, carrying out magnetic stirring, reacting under the protection of nitrogen, tracking a TLC point plate in the whole reaction process, using a developing agent which is a mixture of ethyl acetate and petroleum ether with the volume ratio of 1:2, stopping the reaction after 6 hours, and obtaining a solution containing bromomalondialdehyde 2-aminofluorene bis-Schiff base, wherein the point plate does not have bromomalondialdehyde any more.
(2) And (2) naturally cooling the solution containing the bromo-propandialdehyde 2-aminofluorene bis-Schiff base obtained in the step (1) to room temperature, carrying out vacuum filtration, continuously leaching the filter cake with absolute ethyl alcohol, removing redundant 2-aminofluorene, glacial acetic acid and other impurities, and carrying out vacuum drying on the filtered product to obtain the bromo-propandialdehyde 2-aminofluorene bis-Schiff base.
(3) Adding 2-200 mg of the bromomalondialdehyde 2-aminofluorene bis-Schiff base prepared in the step (2) into 1 liter of distilled water, stirring and dissolving to prepare an aqueous solution, namely the bromomalondialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor.
The structural formula of the bromo-propandialdehyde 2-aminofluorene bis-Schiff base is as follows:
the bromomalondialdehyde condensed 2-aminofluorene bis-Schiff base corrosion inhibitor can be used for corrosion prevention of carbon steel in circulating cooling water.
Compared with the prior art, the method of the invention has the following characteristics:
(1) the preparation method of the bromo-malondialdehyde-condensed 2-aminofluorene bis-Schiff base corrosion inhibitor has the advantages of simple synthesis process, mild reaction conditions and easy operation.
(2) The bromomalondialdehyde condensed 2-aminofluorene bis-Schiff base structure contains two C-N, and compared with a single Schiff base molecule, the bromomalondialdehyde condensed 2-aminofluorene bis-Schiff base structure has more active sites, can enhance the adsorption performance of the bromomalondialdehyde condensed 2-aminofluorene bis-Schiff base on the surface of carbon steel, and has better corrosion inhibition effect.
Drawings
FIG. 1 is an infrared spectrum of bromopropandialdehyde 2-aminofluorene bis-Schiff base in the example of the invention.
FIG. 2 is a mass spectrum of bromopropandialdehyde 2-aminofluorene bis-Schiff base in the example of the invention.
Detailed Description
The technical solution of the present invention is further illustrated by the following examples.
Example (b):
(1) 0.3987g of 2-aminofluorene and 0.1510g of bromomalondialdehyde are respectively weighed and respectively dissolved in 15mL of absolute ethanol to prepare a 2-aminofluorene ethanol solution and a bromomalondialdehyde ethanol solution.
(2) Placing the 2-aminofluorene ethanol solution obtained in the step (1) into a 50mL three-neck flask, adding 3 drops of acetic acid, then adding the bromomalondialdehyde ethanol solution obtained in the step (1), placing the three-neck flask into a constant-temperature water bath kettle, setting the temperature to be 45 ℃, magnetically stirring, reacting under the protection of nitrogen, tracking a TLC point plate in the whole reaction process, wherein a developing agent is ethyl acetate (DCM) and Petroleum Ether (PE) at a ratio of 1:2, reacting for 6 hours, then, the point plate does not have bromomalondialdehyde, stopping the reaction, naturally cooling to room temperature, performing vacuum filtration, continuously leaching a filter cake with absolute ethanol, removing redundant 2-aminofluorene, glacial acetic acid and other impurities, performing vacuum drying on a filtered product to obtain 0.3738g of bromomalonaldehyde-2-aminofluorene bis-Schiff base, and brown powder of bromomalonaldehyde-2-aminofluorene bis-Schiff base, the yield is 68%, and the m.p is 218.3-218.9 ℃.
(3) Adding 2-200 mg of bromopropandialdehyde 2-aminofluorene bis-Schiff base obtained in the step (2) into 1 liter of distilled water, stirring and dissolving to prepare an aqueous solution, namely the bromopropandialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor.
Using VECTOR22 typeAn infrared spectrometer adopts KBr tablet pressing to synthesize bromomalondialdehyde condensed 2-aminofluorene bis-Schiff base with the thickness of 4000-500 cm-1Scanning within the range, and carrying out infrared spectrum structural characterization. In FIG. 1, 1614cm-1At a distance of 2860cm-1Disappearance of characteristic peak of aldehyde group, 3444, 3357, 3200cm-1The characteristic absorption peak of primary amine N-H disappears; and at 1612cm-1Where a stretching vibration occurs, vc ═ N. This indicates that a carbon-nitrogen double bond is formed, i.e., bromopropanal-2-aminofluorene bis-Schiff base is formed.
And (3) carrying out mass spectrum analysis on the synthesized bromomalondialdehyde condensed 2-aminofluorene bis-Schiff base by using a Bruker Solarix XR FTMS mass spectrum analyzer. In FIG. 2, the excimer ion peak [ M + H ] + is 477.09622, and the relative molecular mass is presumed to be 476.09622, which is theoretical 476. The test result is shown to be matched with the relative molecular mass of the target product.
Evaluation methods and results of the corrosion inhibitor products of the examples.
Evaluation method-weight loss method:
(1) carbon steel pattern pretreatment
A20 # carbon steel coupon with the size of 3.0cm multiplied by 1.0cm multiplied by 0.3cm is selected for corrosion weightlessness experiments, carbon steel samples before the experiments are ground by No. 400, No. 800 and No. 1200 metallographic abrasive paper, washed by distilled water, placed in absolute ethyl alcohol for ultrasonic oscillation dehydration, degreased by acetone, blown dry by cold air, sealed by molten paraffin, wrapped by filter paper and placed in a dryer for drying for 4 hours. The dimensions were measured and the surface area was determined prior to testing.
(2) Weight loss experiment
Accurately weighing dried 3 groups of experiment 20# carbon steel samples on an analytical balance, soaking the treated carbon steel sheets in a solution with different concentrations of 5 multiplied by 10 respectively without adding or with adding-6mol/L，1×10-5mol/L，5×10-5mol/L、1×10-4mol/L 5×10-4Soaking the product in 50mL of simulated circulation cooling of mol/L bis-Schiff base corrosion inhibitor at 25 ℃ for 48 h. Then taking out the carbon steel sample, washing with distilled water, dehydrating in ethanol, degreasing in acetone, drying for 4h, and weighing. Three replicates of average weight loss Δ W (g) are given byAnd (3) calculating:
ΔW＝W0-W1(1)
in the formula W0And W1Respectively, the average weight of the sample before and after soaking.
According to the formulas (2), (3) and (4), calculating the corrosion rate (A), the surface coverage rate (theta) and the corrosion inhibition rate (eta) of the corrosion inhibitorW％)。
Wherein, Δ W is the mass difference (g) of the carbon steel sample before and after soaking, and S is the total soaking area (cm) of the carbon steel sample2) T is the soaking time (h); a. theocorrAnd AcorrThe corrosion rate (g cm) of carbon steel in simulated circulating cooling water without and with corrosion inhibitor-2·h-1)。
Evaluation method results-weight loss method experimental data:
and performing a weightlessness experiment according to a weightlessness method, and performing the experiment on each sample in parallel for three times. The average weight loss Δ w (g), the corrosion rate (a), the surface coverage (θ), and the corrosion inhibition rate η w (%) of the corrosion inhibitor were calculated according to the formulas (1), (2), (3), and (4), respectively, and the calculation results are shown in table 1.
TABLE 1 Corrosion parameters of carbon steel samples immersed in recirculated cooling water without and with different concentrations of bis-Schiff base corrosion inhibitor for 48 hours at 25 deg.C
As can be seen from Table 1, the average weight loss of the carbon steel is reduced with the increase of the concentration of the corrosion inhibitor, and the corrosion inhibition efficiency of the bis-Schiff base corrosion inhibitor is increased with the addition of the corrosion inhibitorThe concentration increases. The addition concentration of the corrosion inhibitor is 5 multiplied by 10-4At mol/L, the corrosion inhibitor has the best corrosion inhibition effect.
Claims (2)
1. A preparation method of a bromopropanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor is characterized by comprising the following specific steps:
(1) 0.3987g of 2-aminofluorene and 0.1510g of bromomalondialdehyde are respectively weighed and respectively dissolved in 15mL of absolute ethanol to prepare a 2-aminofluorene ethanol solution and a bromomalondialdehyde ethanol solution; placing a 2-aminofluorene ethanol solution into a 50mL three-necked flask, adding 3 drops of acetic acid, adding a bromomalondialdehyde ethanol solution, placing the three-necked flask into a constant-temperature water bath kettle, setting the temperature at 45 ℃, carrying out magnetic stirring, reacting under the protection of nitrogen, tracking a TLC point plate in the whole reaction process, using a developing agent which is a mixture of ethyl acetate and petroleum ether with the volume ratio of 1:2, stopping the reaction after 6 hours, and obtaining a solution containing bromomalondialdehyde 2-aminofluorene bis-Schiff base, wherein the point plate does not have bromomalondialdehyde any more;
(2) naturally cooling the solution containing the bromo-propandialdehyde 2-aminofluorene bis-Schiff base obtained in the step (1) to room temperature, carrying out vacuum filtration, continuously leaching a filter cake with absolute ethyl alcohol, removing redundant 2-aminofluorene, glacial acetic acid and other impurities, and carrying out vacuum drying on the filtered product to obtain the bromo-propandialdehyde 2-aminofluorene bis-Schiff base;
(3) adding 2 ~ 200mg of the bromomalonaldehyde condensed 2-aminofluorene bis-Schiff base prepared in the step (2) into 1 liter of distilled water, stirring and dissolving to prepare an aqueous solution, namely the bromomalonaldehyde condensed 2-aminofluorene bis-Schiff base corrosion inhibitor;
the structural formula of the bromo-propandialdehyde 2-aminofluorene bis-Schiff base is as follows:
2. the application of the bromopropandialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor prepared by the preparation method of claim 1 is characterized in that the bromopropandialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor is applied to corrosion prevention of carbon steel in circulating cooling water.
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