CN111320611A - Polyether modified imidazoline corrosion inhibitor and preparation method thereof - Google Patents
Polyether modified imidazoline corrosion inhibitor and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of petrochemical industry and fine chemical industry, and particularly relates to a polyether modified imidazoline corrosion inhibitor and a preparation method thereof. The method comprises the steps of introducing two polyether chain segments into a cyanuric chloride structure by utilizing the reaction of polyethylene glycol monomethyl ether and cyanuric chloride to obtain polyether cyanuric chloride; meanwhile, preparing an imidazoline intermediate by using the dehydration reaction of organic acid and diethylenetriamine; and finally, preparing a target product by utilizing the reaction of the imidazoline intermediate and the polyether cyanuric chloride. The method has the advantages of high reaction efficiency, mild conditions, simple operation, no toxic or side reaction and easy realization of large-scale production. The polyether modified oleic imidazoline corrosion inhibitor prepared by the invention has good water solubility, and when the addition amount is 75ppm, the corrosion inhibition rate reaches more than 94%.
Description
Technical Field
The invention belongs to the technical field of petrochemical industry and fine chemical industry, and particularly relates to a polyether modified imidazoline corrosion inhibitor and a preparation method thereof.
Background
The metal corrosion is easy to cause equipment damage and material loss, and can even cause serious safety production accidents. The corrosion inhibitor is added into a corrosion medium, which is one of effective ways for preventing metal equipment from being corroded, is convenient to use, has obvious effect and is widely adopted.
The imidazoline corrosion inhibitor has the advantages of high corrosion inhibition efficiency, excellent thermal stability, low pungent smell, low toxicity and the like, and is the most widely applied corrosion inhibitor product at present. However, the poor water solubility of imidazoline corrosion inhibitors limits their application. Most of metal corrosion occurs near the water phase interface, so the poor water solubility directly influences the migration speed of the corrosion inhibitor to the vicinity of the water phase interface and influences the distribution of the corrosion inhibitor in a water phase system, the efficiency of the corrosion inhibitor is reduced to a great extent, and meanwhile, the organic solvent imidazoline also causes disadvantages to the product transportation and use environment and the like. Therefore, the development of water-soluble imidazoline products is the development direction of imidazoline corrosion inhibitors.
The polyether is a polymer with good water solubility, so that a hydrophilic polyether chain segment is introduced into an imidazoline molecular structure in a covalent bond mode to prepare the polyether-type imidazoline corrosion inhibitor, the water solubility of the imidazoline corrosion inhibitor can be improved, meanwhile, oxygen atoms in the polyether chain segment can also interact with a metal surface, the effective adsorption of corrosion inhibitor molecules on the metal surface can be further improved, the occurrence of metal surface pitting corrosion is reduced, and the corrosion inhibition efficiency of the corrosion inhibitor molecules can be improved. Therefore, the polyether modified imidazoline corrosion inhibitor has wide application prospect. At present, in industrial production, polyether modified imidazoline corrosion inhibitors are prepared by ring-opening polymerization of ethylene oxide monomers in the presence of imidazoline; because the ethylene oxide has a low boiling point (10.8 ℃), is gas at room temperature and belongs to a toxic substance, a reaction system needs measures such as closed pressurization or inert gas protection in the production process, the danger coefficient is high, and the environmental pollution is large. The invention patent (201911199784.4) discloses a gemini polyether imidazoline corrosion inhibitor and a preparation method thereof. But the preparation process involves the coupling reaction of ethylenediamine, the preparation process is complex, and the production cost is high; and two hydrophobic imidazoline structures are introduced into one molecular structure, so that the dissolving capacity of the product in water is limited. The solubility of the aqueous system is limited, and the application range of the aqueous system is limited.
Disclosure of Invention
In order to overcome the technical defects, the invention aims to provide the polyether modified imidazoline corrosion inhibitor and the preparation method thereof.
The realization process of the invention is as follows:
a polyether modified imidazoline corrosion inhibitor has the following structure:
wherein: n is an integer; n is more than or equal to 4; r is selected from phenyl, oleic acid group or naphthenic acid group.
Further, two polyether chain segments are introduced into the cyanuric chloride structure by utilizing the reaction of polyethylene glycol monomethyl ether and cyanuric chloride to obtain polyether cyanuric chloride; meanwhile, preparing an imidazoline intermediate by using the dehydration reaction of organic acid and diethylenetriamine; and finally, preparing a target product by utilizing the reaction of the imidazoline intermediate and the polyether cyanuric chloride.
The preparation method of the polyether modified imidazoline corrosion inhibitor comprises the following steps:
(1) adding polyethylene glycol monomethyl ether into a first round-bottom flask, heating to 40 ℃ to melt the polyethylene glycol monomethyl ether, dropwise adding an acetone solution of cyanuric chloride, simultaneously adding sodium hydroxide, and continuously reacting at 40-45 ℃ for 1-2 hours after dropwise adding to obtain a polyether cyanuric chloride solution;
(2) adding organic acid, diethylenetriamine and a water carrying agent xylene into a second round-bottom flask provided with a water separator and a condenser tube, heating to 145-152 ℃, reacting for 3 hours, continuing heating to 200-210 ℃, reacting for 6-10 hours, cooling to 150 ℃, and distilling under reduced pressure to remove redundant water carrying agent xylene and unreacted diethylenetriamine to obtain an imidazoline intermediate;
(3) and (3) fully mixing the imidazoline intermediate obtained in the step (2) with the polyether cyanuric chloride solution obtained in the step (1) in a third round-bottom flask, adding sodium hydroxide, heating to 80-90 ℃, and reacting for 2 hours to obtain the target product.
Further, in the step (1), the feeding molar ratio of cyanuric chloride to polyethylene glycol monomethyl ether is 1 (2.0-2.1); the mass ratio of the cyanuric chloride to the sodium hydroxide is (1.2-1.5) to 1, and the mass volume ratio of the cyanuric chloride to the acetone is 7.5g (9-10) mL.
Further, in the step (2), the organic acid is selected from one of benzoic acid, oleic acid or naphthenic acid.
Further, in the step (2), the feeding molar ratio of the organic acid to the diethylenetriamine is 1: (1.1-1.2); the mass volume ratio of the diethylenetriamine to the xylene as the water carrying agent is (11.5-12.5) g: 50 mL.
Further, in the step (3), the feeding molar ratio of the polyether cyanuric chloride solution to the imidazoline intermediate is 1 (1-1.05); the feeding molar ratio of the polyether cyanuric chloride solution to the sodium hydroxide is (2-2.1): 2.5.
the invention has the following positive effects:
(1) the invention provides a polyether modified imidazoline corrosion inhibitor, which is characterized in that polyether chain segments and imidazoline structures are respectively introduced by utilizing different activities of three chlorine reaction points of cyanuric chloride.
(2) In the molecular structure of the polyether modified oleic acid imidazoline corrosion inhibitor prepared by the invention, the double polyethylene glycol chain segment is connected with an imidazoline molecule by a chemical bond through cyanuric chloride, and the introduction of the two water-soluble polyethylene glycol chain segments greatly improves the water solubility of the imidazoline corrosion inhibitor.
(3) Meanwhile, the polyethylene glycol chain segment and imidazoline molecule of the polyether modified imidazoline corrosion inhibitor prepared by the invention can play a synergistic effect in the using process: the polyethylene glycol chain segment can improve water solubility, oxygen heteroatoms in the structure can act with the metal surface to promote adsorption, and the hydrophobic imidazoline structure can inhibit wetting of water molecules on the metal surface. The corrosion inhibition effect of the corrosion inhibitor is further ensured through synergistic effect.
(4) The preparation method of the polyether modified imidazoline corrosion inhibitor provided by the invention has the advantages of high reaction efficiency, mild conditions, simple operation, no toxic or side reaction and easy realization of large-scale production.
The reaction principle of the preparation method of the polyether modified imidazoline corrosion inhibitor provided by the invention is that the terminal amino group in the imidazoline molecular structure and the terminal hydroxyl group of polyethylene glycol monomethyl ether are respectively subjected to substitution reaction with active chlorine in cyanuric chloride, and the polyethylene glycol chain segment and imidazoline are combined through cyanuric chloride in a chemical bond mode to generate the polyether modified imidazoline corrosion inhibitor shown in figure 1.
Drawings
FIG. 1 is a reaction equation of a preparation method of the polyether modified imidazoline corrosion inhibitor of the present invention;
FIG. 2 is an infrared spectrum of the polyether modified oleic imidazoline corrosion inhibitor prepared in example 1.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1
(1) Heating 28g of polyethylene glycol monomethyl ether (MPEG350) (80mmol) with the molecular weight of 350g/mol to 40 ℃ in a first round-bottom flask to melt the polyethylene glycol monomethyl ether, dropwise adding 7.5g of cyanuric chloride (40mmol and dissolving the cyanuric chloride by using 10mL of acetone), adding 5g of sodium hydroxide particles, and continuing to react for 1 hour at the temperature of 40 ℃ after dropwise adding to obtain polyether cyanuric chloride (MPEG 350-TriC);
(2) a second round-bottomed flask equipped with a trap and condenser was charged with 28.3g of oleic acid (100mmol), 12.38g of diethylenetriamine (120mmol) and 50mL of xylene as a water-carrying agent. The temperature is raised to 150 ℃ and the reaction is carried out for 3 hours. Continuously heating to 210 ℃ for reaction for 6 hours, and after the reaction is finished, distilling under reduced pressure at 150 ℃ to remove redundant xylene and unreacted diethylenetriamine to obtain oleic acid imidazoline (OIM);
(3) and (3) fully mixing 7.0g of oleic acid imidazoline (20mmol) and 16.2g of polyether cyanuric chloride (MPEG350-TriC) (20mmol) in a third round-bottom flask, adding 1.0g of sodium hydroxide particles, heating to 85 ℃, and reacting for 2 hours to obtain the polyether modified oleic acid imidazoline corrosion inhibitor (MPEG 350-OIM). The infrared spectrogram of the polyether modified oleic imidazoline corrosion inhibitor shown in FIG. 2 is 1109cm-1The polyether chain segment has obvious ether bond stretching vibration peak, and the polyether chain segment is proved to be successfully introduced into the molecular structure of imidazoline.
Example 2
(1) 40g of polyethylene glycol monomethyl ether (MPEG500) (80mmol) with a molecular weight of 500g/mol are melted in a first round-bottomed flask by heating to 40 ℃ and 7.5g of cyanuric chloride (40mmol, dissolved in 9mL of acetone) are added dropwise, 5g of sodium hydroxide particles are added dropwise and the reaction is continued at 45 ℃ for 1 hour after the addition. Obtaining polyether cyanuric chloride (MPEG 500-TriC);
(2) a second round-bottomed flask equipped with a trap and condenser was charged with 12.2g of benzoic acid (100mmol), 11.5g of diethylenetriamine (110mmol) and 50mL of xylene as a water carrying agent. Heating to 150 deg.C, reacting for 3 hr, and heating to 210 deg.C for 10 hr. After the reaction was completed, excess xylene and unreacted diethylenetriamine were distilled off under reduced pressure at 150 ℃. Obtaining benzoic acid imidazoline (BIM);
(3) and (3) fully mixing 3.8g of benzoic acid imidazoline (BIM, 20mmol) and 22.3g of polyether cyanuric chloride (MPEG500-TriC, 20mmol) in a third round-bottom flask, adding 1.0g of sodium hydroxide particles, and heating to 80 ℃ for reaction for 2 hours to obtain the polyether modified benzoic acid imidazoline corrosion inhibitor (MPEG 500-BIM).
Example 3
(1) 63g of polyethylene glycol monomethyl ether (MPEG750) (84mmol) with a molecular weight of 750g/mol are melted in a first round-bottomed flask by heating to 40 ℃ and 7.5g of cyanuric chloride (40mmol, dissolved in 10mL of acetone) are added dropwise, 6.25g of sodium hydroxide particles are added dropwise and the reaction is continued for 2 hours at 40 ℃. Obtaining polyether cyanuric chloride (MPEG 750-TriC);
(2) a second round-bottomed flask equipped with a trap and condenser was charged with 17g of naphthenic acid (100mmol), 12.38g of diethylenetriamine (120mmol) and 50mL of xylene as a water-carrying agent. The temperature is raised to 145 ℃ and the reaction is carried out for 3 hours. The temperature is increased to 200 ℃ and the reaction is continued for 10 hours. After the reaction was completed, excess xylene and unreacted diethylenetriamine were distilled off under reduced pressure at 150 ℃. Naphthenic acid imidazoline (CIM) is obtained;
(3) 4.8g of naphthenic acid imidazoline (CIM, 20mmol) and 32.2g of polyether cyanuric chloride (MPEG750-TriC, 20mmol) are fully mixed in a third round-bottom flask, 1.0g of sodium hydroxide particles are added, and the temperature is raised to 85 ℃ for reaction for 2 hours, so that the polyether modified naphthenic acid imidazoline corrosion inhibitor (MPEG750-CIM) is obtained.
Example 4
(1) 60g of polyethylene glycol monomethyl ether (MPEG750) (80mmol) with a molecular weight of 750g/mol are melted in a first round-bottomed flask by heating to 40 ℃, 7.5g of cyanuric chloride (40 mmol) are added dropwise and dissolved with 10mL of acetone, 5g of sodium hydroxide particles are added dropwise, and the reaction is continued for 1 hour at 40 ℃ after the addition is complete. Obtaining polyether cyanuric chloride (MPEG 750-TriC);
(2) a second round-bottomed flask equipped with a trap and condenser was charged with 28.3g of oleic acid (100mmol), 12.38g of diethylenetriamine (120mmol) and 50mL of xylene as a water-carrying agent. The temperature is raised to 150 ℃ and the reaction is carried out for 3 hours. The temperature was increased to 210 ℃ and the reaction was continued for 6 hours. After the reaction was completed, excess xylene and unreacted diethylenetriamine were distilled off under reduced pressure at 150 ℃. Oleic Imidazoline (OIM) is obtained;
(3) and (3) fully mixing 7.0g of oleic acid imidazoline (OIM, 20mmol) and 32.2g of polyether cyanuric chloride (MPEG750-TriC, 20mmol) in a third round-bottom flask, adding 1.0g of sodium hydroxide particles, and heating to 90 ℃ to react for 2 hours to obtain the polyether modified oleic acid imidazoline corrosion inhibitor (MPEG 750-OIM).
Example 5
(1) 28g of polyethylene glycol monomethyl ether (MPEG350) with a molecular weight of 350g/mol (80mmol) were introduced into a first round-bottomed flask, the temperature was raised to 40 ℃ to melt the polyethylene glycol monomethyl ether, 7.5g of cyanuric chloride (40mmol, dissolved in 10mL of acetone) were added dropwise, 5g of sodium hydroxide particles were added, and the reaction was continued at 40 ℃ for 1 hour after the addition. Obtaining polyether cyanuric chloride (MPEG 350-TriC);
(2) a second round-bottomed flask equipped with a trap and condenser was charged with 17g of naphthenic acid (100mmol), 12.38g of diethylenetriamine (120mmol) and 50mL of xylene as a water-carrying agent. Heating to 150 deg.C, reacting for 3 hr, and heating to 200 deg.C for 6 hr. After the reaction was completed, excess xylene and unreacted diethylenetriamine were distilled off under reduced pressure at 150 ℃. Naphthenic acid imidazoline (CIM) is obtained;
(3) and (3) fully mixing 5.04g of naphthenic acid imidazoline (21mmol) and 16.2g of polyether cyanuric chloride (MPEG350-TriC) (20mmol) in a third round-bottom flask, adding 1.0g of sodium hydroxide particles, and heating to 85 ℃ to react for 2 hours to obtain the polyether modified oleic acid imidazoline corrosion inhibitor (MPEG 350-CIM).
Performance testing
1. Water solubility test
The water solubility of the polyether modified oleic imidazoline (MPEG350-OIM) and Oleic Imidazoline (OIM) prepared in comparative example 1 at a concentration of 100ppm, it was found that solutions of MPEG350-OIM at equivalent concentrations were significantly cleaner than OIM, and UV spectral transmittance tests also showed 98% transmittance of the MPEG350-OIM solution, while OIM was 71%. The polyether modified oleic acid imidazoline corrosion inhibitor prepared by the invention has good water solubility.
2. Experiment of Corrosion inhibition Performance
The corrosion inhibition rate of the MPEG350-OIM, the MPEG500-BIM, the MPEG750-OIM and the MPEG350-CIM prepared in the examples 1, 2, 4 and 5 is measured by a static coupon weight loss method, and the corrosion inhibition rate of the N80 steel in a 1M HCl solution at normal temperature is measured, so that the corrosion inhibition rates of the polyether modified imidazoline corrosion inhibitor are respectively 97.5%, 94%, 95% and 96.5% when the addition amount is 75ppm, and the corrosion inhibition effect is better.
The foregoing is a more detailed description of the invention in connection with specific preferred embodiments and is not intended to limit the invention to the particular forms disclosed. For those skilled in the art to which the invention pertains, several simple deductions or substitutions can be made without departing from the spirit of the invention, and all shall be considered as belonging to the protection scope of the invention.
Claims (7)
1. The polyether modified imidazoline corrosion inhibitor is characterized by having the following structure:
wherein: n is an integer; n is more than or equal to 4; r is selected from phenyl, oleic acid group or naphthenic acid group.
2. The process for preparing the polyether-modified imidazoline corrosion inhibitor of claim 1, wherein: introducing two polyether chain segments into a cyanuric chloride structure by utilizing the reaction of polyethylene glycol monomethyl ether and cyanuric chloride to obtain polyether cyanuric chloride; meanwhile, preparing an imidazoline intermediate by using the dehydration reaction of organic acid and diethylenetriamine; and finally, preparing a target product by utilizing the reaction of the imidazoline intermediate and the polyether cyanuric chloride.
3. The method for preparing the polyether modified imidazoline corrosion inhibitor of claim 2, which comprises the following steps:
(1) adding polyethylene glycol monomethyl ether into a first round-bottom flask, heating to 40 ℃ to melt the polyethylene glycol monomethyl ether, dropwise adding an acetone solution of cyanuric chloride, simultaneously adding sodium hydroxide, and continuously reacting at 40-45 ℃ for 1-2 hours after dropwise adding to obtain a polyether cyanuric chloride solution;
(2) adding organic acid, diethylenetriamine and a water carrying agent xylene into a second round-bottom flask provided with a water separator and a condenser tube, heating to 145-152 ℃, reacting for 3 hours, continuing heating to 200-210 ℃, reacting for 6-10 hours, cooling to 150 ℃, and distilling under reduced pressure to remove redundant water carrying agent xylene and unreacted diethylenetriamine to obtain an imidazoline intermediate;
(3) and (3) fully mixing the imidazoline intermediate obtained in the step (2) with the polyether cyanuric chloride solution obtained in the step (1) in a third round-bottom flask, adding sodium hydroxide, heating to 80-90 ℃, and reacting for 2 hours to obtain the target product.
4. The method for preparing the polyether modified imidazoline corrosion inhibitor of claim 3, wherein the method comprises the following steps: in the step (1), the feeding molar ratio of cyanuric chloride to polyethylene glycol monomethyl ether is 1 (2.0-2.1); the mass ratio of the cyanuric chloride to the sodium hydroxide is (1.2-1.5) to 1, and the mass volume ratio of the cyanuric chloride to the acetone is 7.5g (9-10) mL.
5. The method for preparing the polyether modified imidazoline corrosion inhibitor of claim 3, wherein the method comprises the following steps: in the step (2), the organic acid is selected from one of benzoic acid, oleic acid or naphthenic acid.
6. The method for preparing the polyether modified imidazoline corrosion inhibitor of claim 3, wherein the method comprises the following steps: in the step (2), the feeding molar ratio of the organic acid to the diethylenetriamine is 1: (1.1-1.2); the mass volume ratio of the diethylenetriamine to the xylene as the water carrying agent is (11.5-12.5) g: 50 mL.
7. The method for preparing the polyether modified imidazoline corrosion inhibitor of claim 3, wherein the method comprises the following steps: in the step (3), the feeding molar ratio of the polyether cyanuric chloride solution to the imidazoline intermediate is 1 (1-1.05); the feeding molar ratio of the polyether cyanuric chloride solution to the sodium hydroxide is (2-2.1): 2.5.
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| US6338819B1 (en) * | 1999-02-16 | 2002-01-15 | Baker Hughes Incorporated | Combinations of imidazolines and wetting agents as environmentally acceptable corrosion inhibitors |
| WO2014178738A1 (en) * | 2013-05-02 | 2014-11-06 | Instytut Nafty I Gazu - Panstwowy Instytut Badawczy | Water-soluble corrosion inhibitor for protection of lifting casings and natural gas pipelines as well as the method of its production. |
| CN110760853A (en) * | 2019-11-29 | 2020-02-07 | 陕西科技大学 | Water-soluble gemini polyether imidazoline corrosion inhibitor and preparation method thereof |
| CN110863204A (en) * | 2019-11-29 | 2020-03-06 | 陕西科技大学 | Water-soluble bis-imidazoline corrosion inhibitor and preparation method thereof |
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2020
- 2020-03-31 CN CN202010241954.7A patent/CN111320611A/en active Pending
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| US6338819B1 (en) * | 1999-02-16 | 2002-01-15 | Baker Hughes Incorporated | Combinations of imidazolines and wetting agents as environmentally acceptable corrosion inhibitors |
| WO2014178738A1 (en) * | 2013-05-02 | 2014-11-06 | Instytut Nafty I Gazu - Panstwowy Instytut Badawczy | Water-soluble corrosion inhibitor for protection of lifting casings and natural gas pipelines as well as the method of its production. |
| CN110760853A (en) * | 2019-11-29 | 2020-02-07 | 陕西科技大学 | Water-soluble gemini polyether imidazoline corrosion inhibitor and preparation method thereof |
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Application publication date: 20200623 |