CN102115471A - Triazole compound as well as preparation method and application thereof - Google Patents
Triazole compound as well as preparation method and application thereof Download PDFInfo
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- CN102115471A CN102115471A CN 201010570436 CN201010570436A CN102115471A CN 102115471 A CN102115471 A CN 102115471A CN 201010570436 CN201010570436 CN 201010570436 CN 201010570436 A CN201010570436 A CN 201010570436A CN 102115471 A CN102115471 A CN 102115471A
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Abstract
The invention relates to a copper corrosion inhibitor used in seawater or a sodium chloride solution, in particular to preparation and application of a low-toxicity and high-efficiency corrosion inhibitor for inhibiting the corrosion of metal copper and products thereof in seawater or a sodium chloride medium. A triazole compound is 4-(furan-2-methylene amine)-5-phenyl-4H-1,2,4-triazole-3-thiol shown as a structural formula in the specifications. The triazole compound can be used as a copper seawater corrosion inhibitor for performing corrosion prevention on a copper product in the seawater or the sodium chloride medium. The corrosion inhibitor has the advantages of small using amount, low toxicity, high efficiency, strong capability in durative action and wide application prospect, can be used for effectively inhibiting corrosive destruction to the metal copper.
Description
Technical field
The present invention relates to the corrosion inhibitor of sea water of copper, promptly in order to suppress metallic copper and a kind of low toxicity of the corrosive of goods in seawater or sodium chloride medium thereof, nitrogen heterocyclic ring class inhibiter and application thereof efficiently.
Background technology
Along with the continuous consumption of the various resources in land, the development and utilization oceanic resources become the inevitable approach that solves current resource exhaustion.But seawater belongs to strong electrolyte solution, has intensive corrodibility, has limited the development and utilization of oceanic resources dramatically.Therefore, have only to have solved the etching problem of metallic substance in seawater, could really embody the development and utilization of marine resources and be worth.
Copper has characteristics such as good physical strength, workability, electroconductibility, thermal conductivity, weldability, is used widely in industry, field such as military and civilian for a long time.Yet, though copper comes hydrogen in metal reactivity sequence list after, activity is relatively poor, but copper is in containing corrosive medium systems such as chlorion, vitriol, nitrate, also very easily be subjected to corrosion failure in various degree, thereby lose its original various performances, even bring huge disaster.
At present, though having been arranged, many bibliographical informations cross the corrosion inhibitor of sea water of metallic copper, but the inhibiter quantity that can be applied in the actual production is but very rare, major part is still continued to use traditional benzotriazole compound as copper inhibitor, brings a series of economy and environmental problem to production process.Consumption of the present invention is low, efficient is high, weather resistance is strong, low toxic and environment-friendly, and wide material sources have vast market prospect and using value.
Summary of the invention
The object of the present invention is to provide a kind of low toxicity, environmental protection, effective constituent is nitrogen heterocyclic ring compounds inhibiter efficiently, in order to suppress metallic copper and the corrosion of goods in seawater or sodium chloride medium thereof.
For achieving the above object, the technical solution used in the present invention is:
A kind of triazole compound: 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan can be used as copper seawater corrosion inhibitor, and structural formula is:
Its preparation feedback equation is:
At first with phenylformic acid and methanol mixed, the reaction dehydration obtains methyl benzoate (I), with product (I) and hydrazine hydrate with the mol ratio 2～3h that in alcohol solvent, refluxed in 1: 1.5～1: 2, obtain benzoyl hydrazine (II), with the reaction product (II) that obtains, be added to (mass ratio 1: 5-10), slowly drip dithiocarbonic anhydride, normal-temperature reaction 4h in the ethanolic soln of potassium hydroxide, generate potassium salt compound (III), the dropping of dithiocarbonic anhydride is to adopt minim pipette to drip 30-60 minute with the speed of 1/4-5 second, with product (III) and excess hydrazine hydrate reaction, reflux 6h, reaction solution is poured in the frozen water, regulate pH value 4～5 with dilute hydrochloric acid, suction filtration obtains 3-phenyl-5-sulfydryl-1,2,4-triazole (IV) with compound (IV) and excessive furtural reaction, obtains target compound, prove 3-phenyl-5-sulfydryl-4-furans imido grpup-1 through the nucleus magnetic resonance sign, 2,4-triazole, its fusing point are 193-198 ℃.
Triazole compound can be used as copper seawater corrosion inhibitor, and the brass work in seawater or the sodium chloride medium is carried out corrosion prevention.
Before use, with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan is dissolved in the pimelinketone, the weight ratio of itself and pimelinketone is 1: 10, then at room temperature with ultrasonic disperser mixing solutions is carried out ultra-sonic dispersion 20 minutes, makes it to dissolve fully; Then, with fully the dissolving after solution join in the OP-10 emulsifying agent, the add-on of OP-10 emulsifying agent and pimelinketone and weight ratio be 1: 1, mix under the room temperature and obtain inhibiter, can use.
During use, inhibiter directly is added in the residing seawater of copper, contains 4-(furans-2-benzylidene amino)-5-phenyl-4H-1 in every liter of medium, 2, the amount of 4-triazole-3-mercaptan is 10-50mg, and the submergence temperature is 25 ℃, and the pH scope is 5.5-9.5.
The invention has the beneficial effects as follows:
1. cost is low.Inhibiter effective constituent of the present invention is 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan is synthetic simple, cheap.
2. low toxic and environment-friendly.Inhibiter of the present invention is compared with traditional organic copper inhibiter with inorganic copper inhibitor commonly used at present, and natural degradation is nontoxic or low toxicity material in the sun, can not bring load to environment, meets the trend of green corrosion inhibitor development.
3. suitability is strong.Inhibiter of the present invention applied widely all has good corrosion inhibition under different salinity, temperature, pH.
4. high efficiency.The present invention adds a spot of inhibiter just can effectively suppress the destruction of metallic copper in corrosive medium.
5. good endurance.Inhibiter of the present invention has good weather resistance, can keep higher corrosion inhibition for a long time.
Description of drawings
The 4-that Fig. 1 provides for the embodiment of the invention (furans-2-benzylidene amino)-5-phenyl-4H-1,2, the hydrogen spectrogram of 4-triazole-3-mercaptan.
Embodiment
The present invention adopts electrochemical impedance spectroscopy and two kinds of electrochemical methods of electrokinetic potential polarization to carry out corrosion inhibition and characterizes.Though the inhibition efficiency that two kinds of methods obtain has certain difference, the general trend of the whole bag of tricks is consistent, and this compound all has good corrosion inhibition under different condition as can be seen.
Embodiment 1
4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan preparation method:
Chemical equation is::
At first with phenylformic acid and methanol mixed, the reaction dehydration obtains methyl benzoate (I), with product (I) and hydrazine hydrate with the mol ratio 2～3h that in alcohol solvent, refluxed in 1: 1.5～1: 2, obtain benzoyl hydrazine (II), with the reaction product (II) that obtains, in the ethanolic soln of be added to mass ratio 1: 5～10 potassium hydroxide, slowly drip dithiocarbonic anhydride, normal-temperature reaction 4h generates potassium salt compound (III), and the dropping of dithiocarbonic anhydride is to adopt minim pipette to drip 30-60 minute with the speed of 1/4-5 second; With product (III) and excess hydrazine hydrate reaction, reflux 6h pours reaction solution in the frozen water into, regulate pH value 4～5 with dilute hydrochloric acid, suction filtration obtains 3-phenyl-5-sulfydryl-1,2,4-triazole (IV) is with compound (IV) and furtural reaction, obtain target compound, prove 3-phenyl-5-sulfydryl-4-furans imido grpup-1,2,4-triazole through the nucleus magnetic resonance sign, visible Fig. 1 of the displacement of each H on it, recording its fusing point is 193-198 ℃.
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.015g, temperature is 25 ℃, pH=7.5.
The preparation of microemulsion: with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan is dissolved in the pimelinketone, and the weight ratio of itself and pimelinketone is 1: 10, then at room temperature mixing solutions was carried out ultra-sonic dispersion 20 minutes, make it to dissolve fully with ultrasonic disperser; Then, the solution after the abundant dissolving is joined in the OP-10 emulsifying agent, the add-on of OP-10 emulsifying agent and pimelinketone and weight ratio be 1: 1, be stirred under the room temperature and present uniform microemulsion, can use.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 65.1%, electrokinetic potential polarization 58.8% is shown as the inhibiter that consumption is low, efficient is high.
Corrosion of metal is an electrochemical process, seriously corroded whether and protection whether proper, can judge from corrosion current and charge transfer resistance, and the main means of measuring galvanic corrosion are exactly electrochemical impedance spectroscopy and method of polarization curve.By ac impedance spectroscopy, can obtain the charge transfer resistance of copper, charge transfer resistance is big more, illustrates that the inhibiter molecule is fine and close more at the protective membrane on copper surface, and is also good more to the protection of copper, just can obtain the inhibition efficiency of inhibiter to copper by formula (1).On the other hand, by method of polarization curve, can obtain the corrosion current of copper, corrosion current is big more, illustrates that the corrosive situation is serious more, therefore utilizes corrosion current, obtains the inhibition efficiency of inhibiter according to formula (2), thereby estimates the protection effect of inhibiter.
IE％＝(R
ct-R
0 ct)/R
ct (1)
IE％＝(I
0 corr-I
corr)/I
0 corr (2)
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.025g, temperature is 25 ℃, pH=7.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 71.2%, electrokinetic potential polarization 70.7% is shown as the inhibiter that consumption is low, efficient is high.
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.030g, temperature is 25 ℃, pH=7.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 81.5%, electrokinetic potential polarization 78.9% is shown as the inhibiter that consumption is low, efficient is high.
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.040g, temperature is 25 ℃, pH=7.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 96.4%, electrokinetic potential polarization 94.7% is shown as the inhibiter that consumption is low, efficient is high.
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.050g, temperature is 25 ℃, pH=7.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 99.7%, electrokinetic potential polarization 90.2% is shown as the inhibiter that consumption is low, efficient is high.
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.050g, temperature is 25 ℃, pH=5.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 93.2%, electrokinetic potential polarization 90.3% is shown as high-level efficiency inhibiter under the acidic conditions.
Embodiment 7
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.050g, temperature is 25 ℃, pH=6.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 96.5%, electrokinetic potential polarization 93.8% is shown as high-level efficiency inhibiter under the solutions of weak acidity.
Embodiment 8
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.050g, temperature is 25 ℃, pH=8.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 95.6%, electrokinetic potential polarization 92.4% is shown as high-level efficiency inhibiter under the weak basic condition.
Embodiment 9
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, and medium is 3.5% sodium chloride solution, consumption 0.5L, add 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.050g, temperature is 25 ℃, pH=9.5.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 96.3%, electrokinetic potential polarization 91.2% is shown as high-level efficiency inhibiter under the alkaline condition.
Embodiment 10
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, medium is 3.5% sodium chloride solution, consumption 0.5L adds 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.050g, temperature is 25 ℃, pH=7.5, soak time 10 days.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 99.3% is shown as high-level efficiency inhibiter under the long period.
Embodiment 11
Condition: experiment material is red copper (99.999%), with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan and emulsifying agent are mixed with microemulsion, medium is 3.5% sodium chloride solution, consumption 0.5L adds 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan effective content is 0.050g, temperature is 25 ℃, pH=7.5, soak time 20 days.
Obtaining inhibition efficiency by experimental test is respectively: electrochemical impedance spectroscopy 99.5% is shown as long-time high-level efficiency inhibiter down.
Seawater is the corrosive environment of a complexity, but causes that the main chemical substance of metal corrosive in seawater is a chlorion, and therefore, we can substitute seawater by the configuration sodium chloride solution in the laboratory, and the simulation chlorion is to corrosion of metal.
Claims (7)
1. triazole compound is characterized in that: it is 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2, and 4-triazole-3-mercaptan, structural formula is::
2. the preparation method of a triazole compound is characterized in that:
Chemical equation is:
Concrete preparation process is as follows,
(1) at first with phenylformic acid and excessive methanol mixed, the reaction dehydration obtains methyl benzoate (I);
(2) with product (I) and hydrazine hydrate with the mol ratio 2～3h that in alcohol solvent, refluxed in 1: 1.5～1: 2, obtain benzoyl hydrazine (II);
(3) with the reaction product (II) that obtains, in the ethanolic soln of be added to mass ratio 1: 5～10 potassium hydroxide, slowly drip dithiocarbonic anhydride, normal-temperature reaction 4h generates potassium salt compound (III);
(4) with product (III) and excess hydrazine hydrate reaction, reflux 6h pours reaction solution in the frozen water into, regulates pH value 4～5 with dilute hydrochloric acid, and suction filtration obtains 3-phenyl-5-sulfydryl-1,2,4-triazole (IV);
(5) compound (IV) is continued and the reaction of excessive furtural, obtain target compound.
3. the application of a triazole compound, it is characterized in that: triazole compound can be used as copper seawater corrosion inhibitor, and the brass work in seawater or the sodium chloride medium is carried out corrosion prevention.
4. the application of triazole compound according to claim 3 is characterized in that: described triazole compound as copper seawater corrosion inhibitor is 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2, and 4-triazole-3-mercaptan, structural formula is:
5. the application of triazole compound according to claim 3 is characterized in that: described sodium chloride medium is that mass concentration is the sodium chloride solution of 0.1%-5%.
6. the application of triazole compound according to claim 4, it is characterized in that: described copper seawater corrosion inhibitor, before the application, with 4-(furans-2-benzylidene amino)-5-phenyl-4H-1,2,4-triazole-3-mercaptan is dissolved in the pimelinketone, and the weight ratio of itself and pimelinketone is 1: 10, then at room temperature carried out ultra-sonic dispersion 20 minutes, make it to dissolve fully; Then, with fully the dissolving after solution join in the OP-10 emulsifying agent, the add-on of OP-10 emulsifying agent and pimelinketone and weight ratio be 1: 1, stirring under the room temperature obtains inhibiter, can use.
7. according to the application of claim 4 or 6 described triazole compounds, it is characterized in that: with brass work be immersed in add inhibiter in seawater or the sodium chloride medium, the submergence temperature is 25 ℃, the pH scope is 5.5-9.5, wherein contain 4-(furans-2-benzylidene amino)-5-phenyl-4H-1 in every liter of seawater or the sodium chloride medium, 2,4-triazole-3-amount of mercaptans is 10-50mg.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329273A (en) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | Schiff base containing nitrogenous heterocyclic compound and preparation method and application thereof |
| CN102329274A (en) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | Triazole heterocyclic compound and preparation and application thereof |
| CN103233231A (en) * | 2013-04-25 | 2013-08-07 | 中国科学院海洋研究所 | Application of furan-containing triazole compound used as effective corrosion inhibitor |
| CN103288766A (en) * | 2012-03-01 | 2013-09-11 | 中国科学院海洋研究所 | Triazole compound, and preparation method and application thereof |
| CN114395136A (en) * | 2022-01-19 | 2022-04-26 | 合肥工业大学 | Preparation method and application of furyl 1,2, 4-tolyltriazole iron or copper coordination polymer |
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| CN101191226A (en) * | 2006-12-01 | 2008-06-04 | 中国科学院海洋研究所 | Schiff base heterocycle carbon steel pickling corrosion inhibitor and application thereof |
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| CN101191226A (en) * | 2006-12-01 | 2008-06-04 | 中国科学院海洋研究所 | Schiff base heterocycle carbon steel pickling corrosion inhibitor and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329273A (en) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | Schiff base containing nitrogenous heterocyclic compound and preparation method and application thereof |
| CN102329274A (en) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | Triazole heterocyclic compound and preparation and application thereof |
| CN103288766A (en) * | 2012-03-01 | 2013-09-11 | 中国科学院海洋研究所 | Triazole compound, and preparation method and application thereof |
| CN103233231A (en) * | 2013-04-25 | 2013-08-07 | 中国科学院海洋研究所 | Application of furan-containing triazole compound used as effective corrosion inhibitor |
| CN114395136A (en) * | 2022-01-19 | 2022-04-26 | 合肥工业大学 | Preparation method and application of furyl 1,2, 4-tolyltriazole iron or copper coordination polymer |
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