CN110627681B - Protonated imine molecule and synthesis method of metal copper corrosion inhibitor thereof - Google Patents
Protonated imine molecule and synthesis method of metal copper corrosion inhibitor thereof Download PDFInfo
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- CN110627681B CN110627681B CN201811574680.2A CN201811574680A CN110627681B CN 110627681 B CN110627681 B CN 110627681B CN 201811574680 A CN201811574680 A CN 201811574680A CN 110627681 B CN110627681 B CN 110627681B
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- C07—ORGANIC CHEMISTRY
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- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/30—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having nitrogen atoms of imino groups quaternised
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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
- C23F11/147—Nitrogen-containing compounds containing a nitrogen-to-oxygen bond
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Abstract
The invention provides a method for synthesizing a protonated imine molecule and a metal copper corrosion inhibitor thereof. The protonized imine corrosion inhibitor molecule has a corrosion inhibition effect on metal copper in a sulfuric acid solution with the concentration of 0.5M; the number of heteroatoms, the number of carbon-carbon double bonds and the number of carbon-nitrogen double bonds in molecules are increased, so that the corrosion inhibition effect of the corrosion inhibitor molecules is improved; and the synthesis method is simple, and the raw materials are low in toxicity and environment-friendly.
Description
Technical Field
The invention relates to a corrosion inhibition technology of copper.
Background
The existing copper corrosion inhibitor has a certain corrosion inhibition effect on metal copper in a sulfuric acid solution with the concentration of 0.5M, but the corrosion inhibition efficiency is not high, and a compound of the copper corrosion inhibitor generally has toxicity and certain pollution to the environment.
Disclosure of Invention
The invention aims to provide a protonated imine molecule, which is characterized by having the following structural formula:
the invention claims the application of the compound as a metal copper corrosion inhibitor.
The invention claims a synthetic method of a metal copper corrosion inhibitor, which is characterized by comprising the following steps:
reaction of o-methoxycinnamaldehyde with H2N-(CH2)n-H2Adding N into a 100mL three-neck ground flask, and adding absolute ethyl alcohol as a solvent;
in this step, o-methoxycinnamaldehyde and H2N-(CH2)n-H2The mass ratio of N is: 2: 1-1.2, n is a natural number;
fully reacting at 45 ℃ under the protection of inert gas;
after the reaction is finished, removing the ethanol solution by spinning
Adding solvent into the reactor, crystallizing, filtering to obtain solid
Washing the solid, and recrystallizing to obtain a target compound intermediate product:
and 6, adding the intermediate product into a 1M sulfuric acid solution, stirring at 50 ℃, fully reacting, and spin-drying to obtain the metal copper corrosion inhibitor product.
In the step, the mass ratio of the intermediate product to the sulfuric acid is as follows: 1: 2-2.5.
The synthetic route is as follows:
further, in step 1), H2N-(CH2)n-H2N is a compound with a saturated carbon chain in the middle and amino groups at two ends.
Further, in step 1), H2N-(CH2)n-H2N is ethylenediamine, butanediamine, hexanediamine or octanediamine.
Further, in step 2 ], the sufficient reaction time is 24 hours.
Further, in the step 4), the solvent used for crystallization is a mixture of methanol and n-hexane, and the volume ratio of the methanol to the n-hexane is 1: 2.
Further, in step 5), the solvent used for recrystallization is a mixture of methanol and dichloromethane, and the volume ratio of the methanol to the dichloromethane is 2: 1.
Further, in the step 5 ], the reaction time is 1 hour.
Further, adding the metal copper corrosion inhibitor product into the acidic liquid with the concentration of 0.5mol/L when the metal copper to be protected is in the environment of soaking in the acidic liquid.
The corrosion inhibitor of the protonized imine has a corrosion inhibition effect on metal copper in a sulfuric acid solution with the concentration of 0.5M; the molecular structure increases the number of hetero atoms, carbon-carbon double bonds and carbon-nitrogen double bonds, which is beneficial to improving the corrosion inhibition effect of the corrosion inhibitor molecules; and the synthesis method is simple, and the raw materials are low in toxicity and environment-friendly.
Drawings
FIG. 1 example of (N1E, N2E) -N1, N2-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 2-diethylamine1H nuclear magnetic resonance spectrogram.
FIG. 2 electrochemical impedance spectra from electrochemical measurements with (N1E, N2E) -N1, N2-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 2-diethylamine.
FIG. 3 shows the spectrum obtained by IR spectroscopy using (N1E, N2E) -N1, N2-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 2-diethylamine.
FIG. 4 is a scanning electron microscope image of the polished smooth copper sheet surface.
FIG. 5 is a scanning electron micrograph of the copper surface after soaking a smooth copper sheet in a 0.5M sulfuric acid solution for 7 days.
FIG. 6 scanning electron micrograph of copper surface after soaking a smooth copper sheet in a sulfuric acid solution containing 0.1mM (N1E, N2E) -N1, N2-di- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 2-diethylamine for 7 days. FIG. 7 is a scanned surface of a corrosion solution containing a corrosion inhibitor.
Detailed Description
The present invention is further illustrated by the following examples, but it should not be construed that the scope of the above-described subject matter is limited to the following examples. Various substitutions and alterations can be made without departing from the technical idea of the invention and the scope of the invention is covered by the present invention according to the common technical knowledge and the conventional means in the field.
Example 1
Synthesis of (N1E, N2E) -N1, N2-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 2-diethylamine
Adding o-methoxycinnamaldehyde (2mmol,0.324g) and ethylenediamine (1mmol,60mg) into a three-neck ground flask, adding 30ml of dry absolute ethanol, rapidly turning the reaction liquid red, continuing to react for 24 hours at room temperature under the protection of argon, after the reaction is finished, placing the reaction product in a refrigerator for cooling until no solid is separated out, removing the ethanol solution, adding a proper amount of methanol solution, overnight separating out brown yellow solid, washing cyclohexane for several times, and recrystallizing methanol/dichloromethane to obtain the intermediate product of the target compound. And then adding the intermediate product into 1M sulfuric acid solution (the molar ratio of the intermediate product to sulfuric acid is 1: 2-2.5) to a 100mL three-neck flask, magnetically stirring for 1h at 50 ℃, and then carrying out spin-drying by using a rotary evaporator to obtain a yellow solid, thus obtaining the product.
Example 2
Synthesis of (N1Z) -N1, N4-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 4-butanediamine
Adding o-methoxycinnamaldehyde (2mmol,0.324g) and butanediamine (1mmol,88mg) into a three-neck ground flask, adding 30mL of dry absolute ethanol, rapidly turning the reaction liquid to red, continuing to react for 24 hours at room temperature under the protection of argon, after the reaction is finished, placing the reaction product in a refrigerator for cooling until no solid is separated out, removing the ethanol solution, adding a proper amount of methanol solution, standing overnight, separating out brown solid, washing for 3 times with cyclohexane, and recrystallizing with methanol/dichloromethane to obtain the intermediate product of the target compound. And then adding the intermediate product into 1M sulfuric acid solution (the molar ratio of the intermediate product to sulfuric acid is 1: 2-2.5), magnetically stirring for 1h in a 100mL three-neck flask at 50 ℃, and then spin-drying by using a rotary evaporator to obtain a yellow solid, thus obtaining the product.
Example 3
Synthesis of (N1E, N6Z) -N1, N6-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 6-hexanediamine
Adding o-methoxycinnamaldehyde (2mmol,0.324g) and hexamethylenediamine (1mmol,116mg) into a three-neck ground flask, adding 30mL of dry absolute ethanol, rapidly turning the reaction liquid to red, continuing to react for 24 hours at room temperature under the protection of argon, placing the reaction product into a refrigerator after the reaction is finished, cooling until no solid is separated out, removing the ethanol solution, adding a proper amount of methanol/n-hexane solution, separating out a light brown solid overnight, washing for 3 times with cyclohexane, and recrystallizing with methanol/dichloromethane to obtain the intermediate product of the target compound. Then adding the intermediate product into 1M sulfuric acid solution (the molar ratio of the intermediate product to the sulfuric acid is 1: 2-2.5) and magnetically stirring the mixture in a 100mL three-neck flask at 50 ℃ for 1h, and then carrying out rotary drying by using a rotary evaporator to obtain a yellow solid.
Example 4
Synthesis of (N1E, N8Z) -N1, N8-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 8-octanediamine
Adding o-methoxycinnamaldehyde (2mmol,0.324g) and octanediamine (1mmol,144mg) into a three-neck ground flask, adding 30mL of dry absolute ethanol, rapidly turning the reaction liquid red, continuing to react for 24 hours at room temperature under the protection of argon, placing the mixture in a refrigerator after the reaction is finished, cooling overnight until no solid is separated out, removing the ethanol solution, adding a proper amount of methanol/n-hexane solution, separating out a brownish yellow solid overnight, washing for 3 times with cyclohexane, and recrystallizing with methanol/dichloromethane to obtain an intermediate product of the target compound. And then adding the intermediate product into 1M sulfuric acid solution (the molar ratio of the intermediate product to sulfuric acid is 1: 2-2.5) to a 100mL three-neck flask, magnetically stirring for 1h at 50 ℃, and then carrying out spin-drying by using a rotary evaporator to obtain a yellow solid, thus obtaining the product.
Example 5
Nuclear magnetic hydrogen spectrum characterization of (N1E, N6Z) -N1, N6-di- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 6-hexanediamine
The nuclear magnetic hydrogen spectrum of the corrosion inhibitor (N1E, N6Z) -N1, N6-di- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 6-hexanediamine is shown as the figure 1.
Example 6
Electrochemical testing
At the temperature of 298K, in a medium containing (N1E, N6Z) -N1, N6-di- ((E) -3- (2-Electrochemical testing of copper samples was performed on copper samples in a 0.5M sulfuric acid solution of methoxyphenyl) -allylidene) -1, 6-hexamethylenediamine corrosion inhibitor. The copper material used in the experiment was externally packaged with an insulating material and processed into a cylindrical electrode with epoxy resin. One end of the electrode is welded with the copper wire to conduct the circuit. The working area of the electrode is 1cm2Except that the exposed surface of the working surface is contacted with the corrosive medium solution, the rest parts are sealed and embedded by epoxy resin. The processed copper electrode needs to be used for 800 before testing#、1200#、2000#Polishing the sand paper step by step to enable the surface of the sand paper to be bright and flat, soaking the sand paper in ethanol for ultrasonic cleaning, then drying the sand paper, and placing the sand paper in a dryer.
After an electrochemical experimental device is connected, a solution to be tested is carefully added into an electrolytic cell, a blank test is carried out by using a 0.5M sulfuric acid solution without adding a corrosion inhibitor, and then the solution to be tested containing (N1E, N6Z) -N1, N6-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 6-hexanediamine corrosion inhibitors with different concentrations is tested. And (3) switching on the circuit, testing the Open Circuit Potential (OCP) of the system after the stability lasts 1200s, and if the change of the open circuit potential is less than 3mV within 5min, determining that the system is in a stable state, and testing a potentiodynamic polarization curve (Tafel) and an Electrochemical Impedance Spectroscopy (EIS). The potential scan range of the polarization curve test is open circuit potential +/-250 mV, and the scan rate is 2mV-1The test frequency of the alternating current impedance is 100 kHz-0.01 Hz.
Tafel curve analysis and electrochemical impedance spectroscopy analysis of the assay, as shown in FIG. 2; the corresponding electrochemical parameters are presented in tables 1 and 2, respectively. The results show that (N1E, N6Z) -N1, N6-di- ((E) -3- (2-methoxyphenyl) -allyl idene) -1, 6-hexanediamine has good corrosion inhibition effect on copper, and the corrosion inhibition effect is optimal when the concentration is 0.1 mM.
TABLE 1 Tafel polarization analysis data from electrochemical testing with (N1E, N2E) -N1, N2-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 2-diethylamine.
TABLE 2 electrochemical impedance analysis data from electrochemical testing with (N1E, N2E) -N1, N2-bis- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 2-diethylamine.
Example 7
Infrared Spectrum testing
Performing infrared spectrum test, wherein the infrared spectrum method adopts a KBr tabletting method to prepare samples, and then the test wave number range is 500-4000cm-1。
And (3) total reflection infrared test: the copper electrode sheet needs to be used for 800 before testing#、1200#、2000#、 3000#Sanding the sand paper step by step to enable the surface to be bright and smooth, immersing the sand paper in ethanol for ultrasonic cleaning, then blowing and drying the sand paper, putting the sand paper into a sulfuric acid solution containing 5mL of corrosion inhibitor with the optimal concentration (N1E, N6Z) -N1, N6-di- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 6-hexanediamine for 5h in an electrochemical test, then cleaning the sand paper with distilled water, and blowing and drying the sand paper, wherein the test wave number range is 500 plus 4000cm-1。
The process of complexing copper, in which the action of the corrosion inhibitor on the copper surface is mainly C-N, is illustrated, so that a layer of complex film is formed on the copper surface, the copper surface is separated from the corrosion medium, and the metal copper is protected from corrosion. As shown in fig. 3.
Example 8
Surface analysis
Scanning the surface corrosion morphology by an electron microscope. The surface of a copper sample is subjected to flattening treatment, and 800 parts are used in sequence#、1200#、2000#、3000#Polishing with water-grinding abrasive paper step by step to make the surface of the copper sample flat and smooth, then ultrasonically cleaning the copper sample by distilled water and ethanol for about five minutes, taking out the copper sample, and respectively soaking the red copper sample in a 0.5M sulfuric acid blank solution without adding a corrosion inhibitor and a solution containing (N1E, N6Z) -N1, N6-di- ((E) -3- (2-methoxyphenyl) -allyl idene) -Soaking the 1, 6-hexamethylenediamine corrosion inhibitor in 0.5M sulfuric acid corrosion solution (the adding amount of corrosion agents in each system is the optimal corrosion inhibition concentration measured by the experiment), taking out a sample after 7 days, washing the surface of the sample by distilled water, then drying, carrying out surface corrosion morphology analysis on the sample by adopting an TESCAN VEGA III scanning electron microscope, and comparing the surface corrosion morphology analysis with the corrosion surface of a copper sample without the corrosion inhibitor in 0.5M sulfuric acid blank solution. The accelerating voltage of the scanning electron microscope is 5kV, and the scanning multiple is 10000.
Experiments show that (N1E, N6Z) -N1, N6-di- ((E) -3- (2-methoxyphenyl) -allylidene) -1, 6-hexanediamine has good corrosion inhibition effect on copper, as shown in figure 4 (polished copper sample), figure 6 (scanning of the surface after not putting in corrosion solution containing corrosion inhibitor), and figure 7 (scanning of the surface after putting in corrosion solution containing corrosion inhibitor).
Claims (8)
1. A synthetic method of a metal copper corrosion inhibitor is characterized by comprising the following steps:
reaction of o-methoxycinnamaldehyde with H2N-(CH2)n-H2Adding N into a 100mL three-neck ground flask, and adding absolute ethyl alcohol as a solvent;
in this step, o-methoxycinnamaldehyde and H2N-(CH2)n-H2The mass ratio of N is as follows: 2: 1-1.2, n is a natural number;
heating for full reaction under the protection of inert gas;
after the reaction is finished, removing the ethanol solution by spinning;
adding a solvent into the reactor, crystallizing and filtering to obtain a solid;
washing the solid, and recrystallizing to obtain a target compound intermediate product:
adding the intermediate product into a 1M sulfuric acid solution, heating and stirring, fully reacting, and spin-drying to obtain a metal copper corrosion inhibitor product;
in the step, the mass ratio of the intermediate product to the sulfuric acid is as follows: 1: 2-2.5.
2. According to the claimsThe synthesis method of the metal copper corrosion inhibitor in claim 1 is characterized by comprising the following steps: in step 1), H2N-(CH2)n-H2N is a compound with a saturated carbon chain in the middle and amino groups at two ends.
3. The method for synthesizing the metal copper corrosion inhibitor according to claim 1, wherein the method comprises the following steps: in step 1), H2N-(CH2)n-H2N is ethylenediamine, butanediamine, hexanediamine or octanediamine.
4. The method for synthesizing a metallic copper corrosion inhibitor according to claim 1 or 3, wherein the method comprises the following steps: in step 2 ], the sufficient reaction time is 24 hours.
5. The method for synthesizing the metallic copper corrosion inhibitor according to claim 4, wherein the method comprises the following steps: in the step 4), the solvent used for crystallization is a mixture of methanol and n-hexane.
6. The method for synthesizing the metal copper corrosion inhibitor according to claim 5, wherein the method comprises the following steps: in step 5), the solvent used for recrystallization is a mixture of methanol and dichloromethane.
7. The method for synthesizing the metal copper corrosion inhibitor according to claim 5, wherein the method comprises the following steps: in step 5), the reaction time is 1 h.
8. The use of a metallic copper corrosion inhibitor product obtained by the method according to any one of claims 1 to 7, characterized in that: and adding the metal copper corrosion inhibitor product into the acidic liquid when the metal copper to be protected is in the acidic liquid soaking environment.
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Citations (4)
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|---|---|---|---|---|
| GB1434354A (en) * | 1972-08-17 | 1976-05-05 | Ici Ltd | Inhibition of corrosion |
| EP0410925A1 (en) * | 1989-06-28 | 1991-01-30 | Ciba-Geigy Ag | Electrodepositable coating compositions |
| CN101099871A (en) * | 2006-03-31 | 2008-01-09 | 伊西康公司 | Hydrogen peroxide foam treatment |
| CN106278938A (en) * | 2016-08-11 | 2017-01-04 | 重庆大学 | The synthesis of one class water solublity bis-Schiff base potassium salt and application |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1434354A (en) * | 1972-08-17 | 1976-05-05 | Ici Ltd | Inhibition of corrosion |
| EP0410925A1 (en) * | 1989-06-28 | 1991-01-30 | Ciba-Geigy Ag | Electrodepositable coating compositions |
| CN101099871A (en) * | 2006-03-31 | 2008-01-09 | 伊西康公司 | Hydrogen peroxide foam treatment |
| CN106278938A (en) * | 2016-08-11 | 2017-01-04 | 重庆大学 | The synthesis of one class water solublity bis-Schiff base potassium salt and application |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis, characterization, antimicrobial screening and in silico studies of Schiff bases derived from trans-para-methoxycinnamaldehyde;Obasi, N. L.;《Journal of Molecular Structure》;20171231;8-16 * |
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