CN111378974A - Polyethylene glycol-coupled oleic acid imidazoline water-soluble corrosion inhibitor and preparation method thereof - Google Patents
Polyethylene glycol-coupled oleic acid imidazoline water-soluble corrosion inhibitor and preparation method thereof Download PDFInfo
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- 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
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- 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
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- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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- 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
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Abstract
The invention belongs to the technical field of fine chemical product synthesis, and particularly relates to a polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor and a preparation method thereof. Firstly, adding polyethylene glycol or polyethylene glycol monomethyl ether into an isocyanate coupling system; secondly, after reacting for a certain time, adding hydroxyl oleic acid imidazoline for end capping; finally, the solvent is distilled off to obtain the target product. The principle of the preparation method provided by the invention is the coupling reaction of isocyanate, and the preparation method has the advantages of high reaction efficiency and short reaction time, can effectively save production energy consumption, and is easy to realize green production. Meanwhile, the method can adjust the molecular polarity of the product by regulating and controlling the length of the polyethylene glycol chain segment, thereby meeting the requirements of different application fields on the performance of the corrosion inhibitor.
Description
Technical Field
The invention belongs to the technical field of fine chemical product synthesis, and particularly relates to a polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor and a preparation method thereof.
Background
The use of corrosion inhibitors is an effective way to inhibit corrosion of metals in the ambient medium. The corrosion inhibitor product is also widely applied to the fields of petrochemical industry, industrial pickling, domestic water and the like.
The imidazoline corrosion inhibitor is a corrosion inhibitor product which is most widely applied, and has the advantages of good stability, high corrosion inhibition efficiency, corrosion inhibition function, sterilization property and the like. However, imidazoline corrosion inhibitors generally have the defect of poor water solubility. Compared with the oil soluble corrosion inhibitor, the water soluble corrosion inhibitor has wider application field, safer transportation and use process, more convenient filling and easy complex use with other auxiliary agents. Therefore, the development of water-soluble corrosion inhibitors has attracted much attention in recent years.
At present, measures for improving the water solubility of imidazoline corrosion inhibitors by chemical means mainly rely on quaternization. The preparation idea of the product mainly adopts benzyl chloride, benzyl bromide, dimethyl phosphite, dimethyl sulfate and the like as quaternizing agents. The quaternizing agents are generally characterized by strong toxicity, easy volatilization and the like, and not only bring risks to the production and use process, but also easily cause environmental pollution.
Polyethylene glycol (PEG) and polyethylene glycol monomethyl ether (mPEG) are non-toxic, non-irritating and well water-soluble polymers. Because the molecular structure of the polyethylene glycol has a large number of oxygen heteroatoms, the polyethylene glycol is easy to form adsorption on the surface of metal, and therefore, related researches prove that the polyethylene glycol products have certain corrosion inhibition performance. The polyethylene glycol chain segment is keyed into the imidazoline molecular structure in a chemical bond mode to prepare the polyethylene glycol imidazoline product, so that the water solubility of the imidazoline corrosion inhibitor can be improved, and the corrosion inhibition performance of the imidazoline corrosion inhibitor can be guaranteed. Therefore, the development of corresponding polyethylene glycol imidazoline products and preparation methods thereof according to the molecular structure characteristics of imidazoline is urgently needed. Currently, imidazolines are classified into hydroxyimidazolines and aminoimidazolines according to their terminal groups. The hydroxy imidazoline has higher yield due to lower production cost.
Disclosure of Invention
In order to overcome the inherent defect of poor water solubility of the existing hydroxyoleic acid imidazoline corrosion inhibitor product, the invention aims to provide a polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor and a preparation method thereof. The method takes the terminal hydroxyl in the hydroxyoleic acid imidazoline structure as a reactive group, and keys a nontoxic polyethylene glycol chain segment with good water solubility into the oleic acid imidazoline molecular structure in a chemical bond form to improve the water solubility of the product.
The realization process of the invention is as follows:
a polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor has the following structure:
wherein R is selected from
n is an integer, n is not less than 2; o represents an oxygen element, H represents a hydrogen element, C represents a carbon element, and N represents a nitrogen element.
Further, firstly, adding polyethylene glycol or polyethylene glycol monomethyl ether into an isocyanate coupling system; secondly, after reacting for a certain time, adding hydroxyl oleic acid imidazoline for end capping; finally, the solvent is distilled off to obtain the target product.
Further, the method comprises the following steps:
(1) dissolving a coupling agent in an anhydrous solvent, heating to 70-90 ℃, slowly adding polyethylene glycol or polyethylene glycol monomethyl ether into a coupling agent system, and continuously stirring and reacting at 70-90 ℃ for 2-6 hours after the addition is finished to obtain an isocyanate group-terminated polyethylene glycol intermediate product or an isocyanate group-terminated polyethylene glycol monomethyl ether intermediate product, wherein the coupling agent is selected from isophorone diisocyanate, toluene diisocyanate or diphenylmethane diisocyanate;
(2) adding hydroxyoleic acid imidazoline into the reaction system, and continuously stirring and reacting for 2-6 h at the temperature of 70-90 ℃;
(3) and after the reaction is finished, distilling to remove the solvent to obtain the target product.
Further, in the step (1), the anhydrous solvent is anhydrous toluene or anhydrous tetrahydrofuran.
Further, in the step (1), polyethylene glycol or polyethylene glycol monomethyl ether is slowly added into the coupling agent system, wherein the slow adding rate is 0.5 mol/h.
Further, in the step (1), the molecular weight of the polyethylene glycol and the polyethylene glycol monomethyl ether is 200-10000 g/mol.
Further, in the step (1), the feeding molar ratio of the coupling agent to the polyethylene glycol is (2-2.4): 1; in the step (2), the feeding molar ratio of the hydroxyoleic acid imidazoline to the polyethylene glycol is (2-2.4): 1.
Further, in the step (1), the feeding molar ratio of the coupling agent to the polyethylene glycol monomethyl ether is (1-1.2): 1; in the step (2), the feeding molar ratio of the hydroxyoleic acid imidazoline to the polyethylene glycol monomethyl ether is (1-1.2): 1.
Furthermore, in the step (1), the feeding mass-volume ratio of the coupling agent to the anhydrous solvent is 1g (5-50) mL.
The method is characterized in that hydroxyoleic acid imidazoline is used as a reaction initiator, and a water-soluble chain segment of polyethylene glycol or polyethylene glycol monomethyl ether is keyed into a molecular structure of the reaction initiator in a covalent bond mode through a coupling reaction of isocyanate to obtain a target product.
The invention has the following positive effects:
(1) the principle of the preparation method provided by the invention is the coupling reaction of isocyanate, and the preparation method has the advantages of high reaction efficiency and short reaction time, can effectively save production energy consumption, and is easy to realize green production.
(2) The preparation method provided by the invention can adjust the molecular polarity of the product by regulating the length of the polyethylene glycol chain segment, and meets the performance requirements of different application fields on the corrosion inhibitor.
(3) The polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor prepared by the invention has the advantages that the molecules of the corrosion inhibitor present a relatively large linear structure through the coupling reaction of isocyanate, a large amount of hetero atoms in the molecules can promote the adsorption of the corrosion inhibitor on the metal surface, and meanwhile, the large molecular size is beneficial to forming a more compact adsorption film on the metal surface, so that the wetting of a corrosion medium on the metal surface is better inhibited, and the corrosion inhibition effect is exerted.
Drawings
FIG. 1 is an infrared spectrum of the water-soluble corrosion inhibitor of polyethylene glycol-coupled imidazoline oleate prepared in example 1;
FIG. 2 is a nuclear magnetic hydrogen spectrum of the water-soluble corrosion inhibitor of polyethylene glycol-coupled oleic acid imidazoline prepared in example 1.
Detailed Description
The present invention will be further described with reference to the following examples.
Example 1 coupling agent is isophorone diisocyanate
(1) Dissolving 22.2g of isophorone diisocyanate (0.1mol) in 222mL of anhydrous tetrahydrofuran in a reaction container, heating to 70 ℃, slowly adding 100g of polyethylene glycol (0.05mol) with the molecular weight of 2000g/mol, keeping the adding process for 1h, and continuously stirring and reacting at 70 ℃ for 3h after the adding is finished to obtain an isocyanate group-terminated polyethylene glycol intermediate product;
(2) adding 35g of hydroxyoleic imidazoline (0.1mol) into the reaction system, and continuously stirring and reacting for 4 hours at the temperature of 70 ℃;
(3) after the reaction is finished, distilling to remove the solvent to obtain a polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor product, and testing an infrared spectrum and a nuclear magnetic hydrogen spectrum, wherein the infrared spectrum and the nuclear magnetic hydrogen spectrum are shown in a figure 1 and a figure 2.
1082cm in the infrared spectrum shown in FIG. 1-1Has a remarkable ether bond stretching vibration peak at 1726cm-1Has a distinct ester carbonyl stretching vibration peak at 1533cm-1Having a C-N bond absorption peak of 1620cm-1Has obvious imidazole ring characteristic absorption, and at the same time, 2270cm-1The characteristic absorption peak of the isocyanate group disappears completely, which proves that the coupling agent participates in the reaction completely, and the polyethylene glycol chain segment is successfully introduced into the imidazoline structure.
The nuclear magnetic hydrogen spectrum shown in fig. 2 can clearly detect the proton chemical shift in the imidazole ring structure, the proton chemical shift in the methylene in the polyethylene glycol structure and the chemical shift of the methyl proton in the isocyanate group, and confirms that the obtained target product has a correct structure.
The reaction equation is specifically as follows:
example 2 coupling agent is isophorone diisocyanate
(1) 13.32g of isophorone diisocyanate (0.06mol) are dissolved in 666mL of anhydrous toluene and heated to 90 ℃ in a reaction vessel, and 500g of polyethylene glycol monomethyl ether (0.05mol) having a molecular weight of 10000g/mol are slowly added over a period of 1 h. After the addition is finished, continuously stirring and reacting for 6 hours at the temperature of 90 ℃ to obtain an isocyanate group-terminated polyethylene glycol monomethyl ether intermediate product;
(2) adding 17.5g of hydroxyoleic imidazoline (0.05mol) into the reaction system, and continuously stirring and reacting for 6 hours at 90 ℃;
(3) and after the reaction is finished, distilling to remove the solvent to obtain the polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor product.
The reaction equation is specifically as follows:
example 3 coupling agent is toluene diisocyanate
(1) 8.7g of toluene diisocyanate (0.05mol) are dissolved in 43.5mL of anhydrous tetrahydrofuran and heated to 70 ℃ in a reaction vessel, 10g of polyethylene glycol monomethyl ether (0.05mol) having a molecular weight of 200g/mol are slowly added over the course of 1 h. After the addition is finished, continuously stirring and reacting for 2h at 70 ℃ to obtain an isocyanate group-terminated polyethylene glycol monomethyl ether intermediate product;
(2) adding 17.5g of hydroxyoleic imidazoline (0.05mol) into the reaction system, and continuously stirring and reacting for 2 hours at the temperature of 70 ℃;
(3) and after the reaction is finished, distilling to remove the solvent to obtain the polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor product.
The reaction equation is specifically as follows:
example 4 coupling agent is toluene diisocyanate
(1) In a reaction vessel 17.42g of toluene diisocyanate (0.1mol) were dissolved in 348.4mL of anhydrous tetrahydrofuran and heated to 70 ℃ and 200g of polyethylene glycol (0.05mol) having a molecular weight of 400g/mol were slowly added over the course of 1 h. After the addition is finished, continuously stirring and reacting for 2h at 70 ℃ to obtain an isocyanate group-terminated polyethylene glycol intermediate product;
(2) adding 35g of hydroxyoleic acid imidazoline (0.1mol) into the reaction system, and continuously stirring and reacting for 2 hours at the temperature of 70 ℃;
(3) and after the reaction is finished, distilling to remove the solvent to obtain the polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor product.
The reaction equation is specifically as follows:
example 5 coupling agent is diphenylmethane diisocyanate
(1) 15g of diphenylmethane diisocyanate (0.06mol) were dissolved in 750mL of anhydrous toluene and heated to 90 ℃ in a reaction vessel, and 500g of polyethylene glycol monomethyl ether (0.05mol) having a molecular weight of 10000g/mol were slowly added over a period of 1 h. After the addition is finished, continuously stirring and reacting for 6 hours at the temperature of 90 ℃ to obtain an isocyanate group-terminated polyethylene glycol monomethyl ether intermediate product;
(2) adding 21g of hydroxyoleic imidazoline (0.06mol) into the reaction system, and continuously stirring and reacting for 6 hours at the temperature of 90 ℃;
(3) and after the reaction is finished, distilling to remove the solvent to obtain the polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor product.
The reaction equation is specifically as follows:
example 6 coupling agent is diphenylmethane diisocyanate
(1) In a reaction vessel 30g of diphenylmethane diisocyanate (0.12mol) were dissolved in 300mL of anhydrous toluene and heated to 90 ℃ and 100g of polyethylene glycol having a molecular weight of 2000g/mol (0.05mol) were slowly added over the course of 1 h. After the addition is finished, continuously stirring and reacting for 6 hours at the temperature of 90 ℃ to obtain an isocyanate group-terminated polyethylene glycol intermediate product;
(2) 42g of hydroxyoleic acid imidazoline (0.12mol) is added into the reaction system, and the mixture is continuously stirred and reacted for 6 hours at the temperature of 90 ℃;
(3) and after the reaction is finished, distilling to remove the solvent to obtain the polyethylene glycol coupled oleic acid imidazoline water-soluble corrosion inhibitor product.
The reaction equation is specifically as follows:
performance testing
(1) Water solubility
The water solubility test was carried out on the corrosion inhibitor product obtained in example 1 with isophorone diisocyanate as coupling agent and polyethylene glycol molecular weight of 2000 g/mol. The results show that at a concentration of 100ppm, the product solution is clear and transparent, whereas the imidazoline oleic solution without polyethylene glycol incorporation is cloudy. The transmittance test of ultraviolet visible spectrum under 500nm shows that the transmittance of the product obtained in example 1 is more than 95%, which indicates that the product is in a dissolved state, and the transmittance of oleic acid imidazoline without polyethylene glycol is 70-80%.
(2) Corrosion inhibition performance
The corrosion inhibition performance of the product obtained in example 1 was tested by a static coupon weight loss method. Before the test, the Q235 standard steel sheet is washed by acetone and deionized water in sequence, dried to constant weight and weighed for corrosion test. The corrosion medium is 1M HCl solution, the corrosion temperature is 30 ℃, the addition concentration of the corrosion inhibitor is 100ppm, the result shows that the corrosion inhibition rate is 93.8%, and the corrosion inhibition performance of the product is excellent.
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 (9)
1. The water-soluble corrosion inhibitor of polyethylene glycol coupled oleic acid imidazoline is characterized by having the following structure:
wherein R is selected from
n is an integer, n is not less than 2; o represents an oxygen element, H represents a hydrogen element, C represents a carbon element, and N represents a nitrogen element.
2. The preparation method of the polyethylene glycol-coupled oleic acid imidazoline water-soluble corrosion inhibitor as claimed in claim 1, wherein the preparation method comprises the following steps: firstly, adding polyethylene glycol or polyethylene glycol monomethyl ether into an isocyanate coupling system; secondly, after reacting for a certain time, adding hydroxyl oleic acid imidazoline for end capping; finally, the solvent is distilled off to obtain the target product.
3. The preparation method of the water-soluble corrosion inhibitor of polyethylene glycol coupled oleic acid imidazoline according to claim 2, which is characterized by comprising the following steps:
(1) dissolving a coupling agent in an anhydrous solvent, heating to 70-90 ℃, slowly adding polyethylene glycol or polyethylene glycol monomethyl ether into a coupling agent system, and continuously stirring and reacting at 70-90 ℃ for 2-6 hours after the addition is finished to obtain an isocyanate group-terminated polyethylene glycol intermediate product or an isocyanate group-terminated polyethylene glycol monomethyl ether intermediate product, wherein the coupling agent is selected from isophorone diisocyanate, toluene diisocyanate or diphenylmethane diisocyanate;
(2) adding hydroxyoleic acid imidazoline into the reaction system, and continuously stirring and reacting for 2-6 h at the temperature of 70-90 ℃;
(3) and after the reaction is finished, distilling to remove the solvent to obtain the target product.
4. The preparation method of the water-soluble corrosion inhibitor of the polyethylene glycol-coupled oleic acid imidazoline according to claim 3, which is characterized in that: in the step (1), the anhydrous solvent is anhydrous toluene or anhydrous tetrahydrofuran.
5. The preparation method of the water-soluble corrosion inhibitor of the polyethylene glycol-coupled oleic acid imidazoline according to claim 3, which is characterized in that: in the step (1), polyethylene glycol or polyethylene glycol monomethyl ether is slowly added into a coupling agent system, wherein the slow adding speed is 0.5 mol/h.
6. The preparation method of the water-soluble corrosion inhibitor of the polyethylene glycol-coupled oleic acid imidazoline according to claim 3, which is characterized in that: in the step (1), the molecular weight of the polyethylene glycol and the polyethylene glycol monomethyl ether is 200-10000 g/mol.
7. The preparation method of the water-soluble corrosion inhibitor of the polyethylene glycol-coupled oleic acid imidazoline according to claim 3, which is characterized in that: in the step (1), the feeding molar ratio of the coupling agent to the polyethylene glycol is (2-2.4) to 1; in the step (2), the feeding molar ratio of the hydroxyoleic acid imidazoline to the polyethylene glycol is (2-2.4): 1.
8. The preparation method of the water-soluble corrosion inhibitor of the polyethylene glycol-coupled oleic acid imidazoline according to claim 3, which is characterized in that: in the step (1), the feeding molar ratio of the coupling agent to the polyethylene glycol monomethyl ether is (1-1.2): 1; in the step (2), the feeding molar ratio of the hydroxyoleic acid imidazoline to the polyethylene glycol monomethyl ether is (1-1.2): 1.
9. The preparation method of the water-soluble corrosion inhibitor of the polyethylene glycol-coupled oleic acid imidazoline according to claim 3, which is characterized in that: in the step (1), the feeding mass-volume ratio of the coupling agent to the anhydrous solvent is 1g (5-50) mL.
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| CN111793798A (en) * | 2020-07-21 | 2020-10-20 | 广东粤首新科技有限公司 | Water-soluble corrosion inhibitor for hydrogenation device and preparation method and application thereof |
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| CN111793798A (en) * | 2020-07-21 | 2020-10-20 | 广东粤首新科技有限公司 | Water-soluble corrosion inhibitor for hydrogenation device and preparation method and application thereof |
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