CN110724066B - Preparation method and application of pentanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor - Google Patents
Preparation method and application of pentanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor Download PDFInfo
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 35
- -1 pentanedialdehyde 2-aminofluorene Chemical compound 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- CFRFHWQYWJMEJN-UHFFFAOYSA-N 9h-fluoren-2-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3CC2=C1 CFRFHWQYWJMEJN-UHFFFAOYSA-N 0.000 claims abstract description 26
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- MMVWTWJHJXHKKW-UHFFFAOYSA-N ethanol;pentanedial Chemical compound CCO.O=CCCCC=O MMVWTWJHJXHKKW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 18
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- 238000006243 chemical reaction Methods 0.000 claims description 9
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- 239000003795 chemical substances by application Substances 0.000 claims description 3
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- 239000000126 substance Substances 0.000 claims description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 238000005536 corrosion prevention Methods 0.000 claims description 2
- 238000003760 magnetic stirring Methods 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 4
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- Mechanical Engineering (AREA)
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- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
The invention discloses a preparation method and application of a pentanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor. According to the invention, a glutaraldehyde ethanol solution and a 2-aminofluorene ethanol solution are mixed for condensation reaction to obtain glutaraldehyde-condensed 2-aminofluorene bis-Schiff base, and then water is used as a solvent to prepare the glutaraldehyde-condensed 2-aminofluorene bis-Schiff base corrosion inhibitor. The 2-aminofluorene bis-Schiff base for pentanedialdehyde condensation contains two functional groups with the carbon number = N, so that the adsorption effect of the base on the surface of carbon steel is enhanced, and the corrosion inhibitor can keep higher corrosion inhibition effect in circulating cooling water with high temperature and a large amount of dissolved oxygen, chloride ions, sulfate ions and microorganisms.
Description
Technical Field
The invention belongs to the field of corrosion inhibitors, and particularly relates to a preparation method and application of a pentanedialdehyde 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 glutaraldehyde condensed 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 2-aminofluorene bis-Schiff base corrosion inhibitor for the glutaraldehyde acetal comprises the following specific steps:
(1) 0.3987g of 2-aminofluorene and 0.2002g of glutaraldehyde are respectively weighed and respectively dissolved in 15mL of absolute ethanol to prepare a 2-aminofluorene ethanol solution and a glutaraldehyde ethanol solution; placing a 2-aminofluorene ethanol solution into a 50mL three-neck flask, adding 3 drops of acetic acid, adding a glutaraldehyde 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, carrying out TLC point plate tracking in the whole reaction process, adopting an iodine cylinder to climb a plate because aldehyde substances do not develop color on a silica gel plate, adopting a mixture of dichloromethane and petroleum ether with a volume ratio of 6:5 as a developing agent, stopping the reaction when glutaraldehyde does not exist in the plate after the reaction is carried out for 9 hours, and obtaining a solution containing glutaraldehyde-condensed 2-aminofluorene bis-schiff base.
(2) And (2) naturally cooling the solution containing the glutaraldehyde-condensed 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 glutaraldehyde-condensed 2-aminofluorene bis-Schiff base.
(3) Adding 2-200 mg of the glutaraldehyde 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 glutaraldehyde 2-aminofluorene bis-Schiff base corrosion inhibitor.
The structural formula of the 2-aminofluorene bis-Schiff base for glutaraldehyde bis-aldehyde is as follows:
the glutaraldehyde condensed 2-aminofluorene bis-Schiff base corrosion inhibitor is applied to corrosion prevention of carbon steel in a circulating cooling water system.
Compared with the prior art, the method of the invention has the following characteristics:
(1) the preparation method of the glutaraldehyde condensed 2-aminofluorene bis-Schiff base corrosion inhibitor has the advantages of simple synthesis process, mild reaction conditions and easy operation.
(2) The structure of the pentanedialdehyde condensed 2-aminofluorene Schiff base contains two C ═ N, and compared with a single Schiff base molecule, the pentanedialdehyde condensed 2-aminofluorene Schiff base has more active sites, can enhance the adsorption performance of the pentanedialdehyde condensed 2-aminofluorene Schiff base on the surface of carbon steel, and the corrosion inhibitor prepared by the method has better corrosion inhibition effect.
Drawings
FIG. 1 is an infrared spectrum of a glutaraldehyde-condensed 2-aminofluorene bis-Schiff base in an example of the present invention.
FIG. 2 is a mass spectrum of glutaraldehyde-condensed 2-aminofluorene bis-Schiff base in an example of the present 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 0.2002g of glutaraldehyde are weighed respectively and dissolved in 15mL of absolute ethanol respectively to prepare a 2-aminofluorene ethanol solution and a glutaraldehyde 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 glutaraldehyde 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, adopting an iodine cylinder to climb the plate, wherein a developing agent is Dichloromethane (DCM) and Petroleum Ether (PE) is 6:5, reacting for 9 hours, stopping the reaction when no glutaraldehyde exists in the point plate, naturally cooling to room temperature, decompressing and filtering, continuously leaching a filter cake with anhydrous ethanol, removing raw materials of 2-aminofluorene, glacial acetic acid and other impurities, vacuum drying the filtered product to obtain 0.3953g of glutaraldehyde-2-aminofluorene bis-schiff base, the pentanedialdehyde 2-aminofluorene bis-Schiff base is light yellow brown powder, the yield is 66%, and the m.p. is 225.6-226.3 ℃.
(3) And (3) weighing 2-200 mg of the glutaraldehyde 2-aminofluorene bis-Schiff base obtained in the step (2), adding into 1 liter of distilled water, stirring and dissolving to prepare an aqueous solution, namely the glutaraldehyde 2-aminofluorene bis-Schiff base corrosion inhibitor.
The synthesized glutaraldehyde-condensed 2-aminofluorene bis-Schiff base is subjected to 4000-500 cm by using a VECTOR22 type infrared spectrometer and a KBr tablet-1Scanning within the range, and carrying out infrared spectrum structural characterization. In FIG. 1, 1648cm-1And 2950cm-1Disappearance of characteristic peak of aldehyde group, 3444, 3357, 3200cm-1The characteristic absorption peak of primary amine N-H disappears; at 1612cm-1Where a stretching vibration occurs, vc ═ N. This indicates the presence of carbonAnd generating a nitrogen double bond, namely synthesizing the 2-aminofluorene bis-Schiff base of the pentanedialdehyde acetal.
Mass spectrometry of the synthesized glutaraldehyde-condensed 2-aminofluorene Schiff base was performed using a Bruker Solarix XR FTMS mass spectrometer. In FIG. 2, the excimer ion peak [ M + H ] + is 427.21790, which is presumed to have a relative molecular mass of 426.21790 and a theoretical value of 426. 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 0.3 cm is selected for corrosion weightlessness experiments, carbon steel samples before the experiments are polished 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 were tested and the average weight loss Δ W (g) was calculated as follows:
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
From table 1, it can be seen that the average weight loss of the carbon steel decreases with the increase of the concentration of the corrosion inhibitor, and the corrosion inhibition efficiency of the bis-schiff base corrosion inhibitor increases with the increase of the addition concentration. 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 glutaraldehyde condensed 2-aminofluorene bis-Schiff base corrosion inhibitor is characterized by comprising the following specific steps:
(1) 0.3987g of 2-aminofluorene and 0.2002g of glutaraldehyde are respectively weighed and respectively dissolved in 15mL of absolute ethanol to prepare a 2-aminofluorene ethanol solution and a glutaraldehyde ethanol solution; placing a 2-aminofluorene ethanol solution into a 50mL three-necked flask, adding 3 drops of acetic acid, adding a glutaraldehyde 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, carrying out TLC point plate tracking in the whole reaction process, adopting an iodine cylinder to climb a plate because aldehyde substances do not develop color on a silica gel plate, adopting a mixture of dichloromethane and petroleum ether with a volume ratio of 6:5 as a developing agent, stopping the reaction when glutaraldehyde does not exist in the plate after the reaction is carried out for 9 hours, and obtaining a solution containing glutaraldehyde-condensed 2-aminofluorene bis-Schiff base;
(2) naturally cooling the solution containing the glutaraldehyde-condensed 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 a filtered product to obtain the glutaraldehyde-condensed 2-aminofluorene bis-Schiff base;
(3) adding 2-200 mg of the glutaraldehyde 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 glutaraldehyde 2-aminofluorene bis-Schiff base corrosion inhibitor;
the structural formula of the 2-aminofluorene bis-Schiff base for glutaraldehyde bis-aldehyde is as follows:
2. the application of the pentanedialdehyde 2-aminofluorene bis-schiff base corrosion inhibitor prepared by the preparation method of claim 1, wherein the pentanedialdehyde 2-aminofluorene bis-schiff base corrosion inhibitor is applied to corrosion prevention of carbon steel in a circulating cooling water system.
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| CN106543029A (en) * | 2016-10-26 | 2017-03-29 | 桂林理工大学 | N,N`（2 aminofluorenes）The preparation method of contracting Biformyl Schiff's base iron complex |
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| Synthesis of 2-aminofluorene bis-Schiff base and corrosion inhibition performance for carbon steel in HCl;Chuxin Liang等;《Journal of Molecular Liquids》;20181220;第277卷;第330-340页 * |
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