CN109371401B - Polyoxyethylene ether imidazoline sulfonate corrosion inhibitor and preparation method thereof - Google Patents
Polyoxyethylene ether imidazoline sulfonate corrosion inhibitor and preparation method thereof Download PDFInfo
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- 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 discloses a polyoxyethylene ether imidazoline sulfonate corrosion inhibitor and a preparation method thereof, wherein the corrosion inhibitor has a structural formula
Wherein R represents a carbon chain number of C11～C17N is an integer of 5 to 15; the intermediate is prepared by synthesizing a long-carbon-chain imidazoline intermediate by using long-carbon-chain carboxylic acid and diethylenetriamine as raw materials, performing addition reaction on the intermediate and ethylene oxide under an alkaline condition to generate polyoxyethylene ether imidazoline, and performing quaternization reaction on the polyoxyethylene ether imidazoline and 3-chloro-2-hydroxypropanesulfonic acid sodium salt. The corrosion inhibitor structure of the invention introduces active groups of-OH and-SO3 ‑The corrosion inhibitor has good solubility in water, greatly enhances the adsorption activity on the metal surface and shows excellent corrosion inhibition performance; and the compound has good biodegradability and low toxicity, and belongs to an environment-friendly corrosion inhibitor. The corrosion inhibitor of the invention can be applied to CO-containing2And H2S oil field produced water medium, and can be applied to CO2The corrosion of the fluid to the carbon steel is slowed down in a high-temperature and high-pressure medium of the oil displacement system.
Description
Technical Field
The invention belongs to the technical field of fine chemical products, and particularly relates to a polyoxyethylene ether imidazoline sulfonate corrosion inhibitor and a preparation method thereof.
Background
Introducing CO2Injected into oil layer to store CO2Can also greatly improve the recovery ratio of the oil-gas field to achieve CO2The win-win purpose of emission reduction and efficient oil reservoir development. CO injection2The oil displacement engineering is vigorously developed at home and abroad, and CO2The corrosion problem to low carbon steel equipment such as an injection system, an underground pipe column, a production system pipe network and the like is more and more prominent. By using corrosion inhibitor techniqueSuppression of CO ubiquitous in oil and gas fields2The corrosion has the advantages of low investment, small dosage, no need of changing original equipment and process flow and the like, and is widely applied to oil and gas fields. Tests show that imidazoline and derivatives thereof have good compatibility, high thermal stability and low toxicity, can inhibit scale and sterilize, and have good CO inhibition effect after being compounded with other additives2The corrosion effect belongs to an environment-friendly corrosion inhibitor.
Most of the imidazoline is applied in aqueous solution, and the conventional imidazoline is generally poor in water solubility, so that the quaternization of the imidazoline into imidazoline quaternary ammonium salt is a main technical approach for improving the water solubility of the imidazoline corrosion inhibitor. Most of the prior common quaternizing agents are benzyl chloride, sodium chloroacetate, diethyl sulfate, sulfamic acid and the like, and the polarity level of the quaternary ammonium salt is not enough to ensure the good water solubility of the whole imidazoline molecule, so the stability of the quaternary ammonium salt is poor, and the layering phenomenon is easy to cause after long-term storage.
Disclosure of Invention
The invention aims to provide a catalyst which has good water solubility and stable performance and contains CO2And H2Oil field produced water medium of S, or CO2The polyoxyethylene ether imidazoline sulfonate corrosion inhibitor has strong inhibition capability on corrosion caused by a high-temperature high-pressure medium in an oil displacement system, and provides a preparation method for the corrosion inhibitor.
Aiming at the purposes, the structural formula of the polyoxyethylene ether imidazoline sulfonate adopted by the invention is as follows:
wherein R represents a carbon chain number of C11～C17Saturated alkyl, carbon chain number C11～C17The mono alkenyl group and the carbon chain number of C11～C17Any one of the above-mentioned bisalkenyl groups, wherein n is an integer of 5 to 15.
In the above structural formula, R preferably represents any one of undecyl, 4-undecenyl, tridecyl, pentadecyl, pentadecenyl, 8, 11-pentadecenyl, 9-hexadecenyl, heptadecyl, 8-heptadecenyl, and 8, 11-heptadecadienyl.
The preparation method of the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor comprises the following steps:
1. and (2) carrying out reflux reaction on the long-carbon-chain carboxylic acid shown in the formula I and diethylenetriamine at 140-200 ℃ for 4-6 h by using dimethylbenzene as a solvent, and removing the dimethylbenzene by rotary evaporation when the removal amount is more than 85% of the theoretical dehydration amount to obtain a 1-aminoethyl-2-long-carbon-chain imidazoline intermediate shown in the formula II.
2. The 1-aminoethyl-2-long carbon chain imidazoline intermediate obtained in the step 1 and alkali are added into N2Stirring and heating to 100-120 ℃ under protection, introducing ethylene oxide gas, continuing stirring at constant temperature for 30-45 min, stopping introducing the gas, and separating and purifying to obtain the polyoxyethylene ether imidazoline shown in the formula III.
3. Heating the polyoxyethylene ether imidazoline and the 3-chloro-2-hydroxypropanesulfonic acid sodium salt obtained in the step 2 to 80-90 ℃, adjusting the pH of the system to 7.5-8.0, and then continuing to react for 2-3 hours to obtain the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor shown in the formula IV, wherein the reaction process is as follows:
in the step 1, the molar ratio of the long carbon chain carboxylic acid to diethylenetriamine is 1:1.05 to 1:1.20, and the preferable long carbon chain carboxylic acid is any one of lauric acid, 5-dodecenoic acid, myristic acid, palmitic acid, 2-hexadecenoic acid, 9, 12-hexadecadienyl, 10-heptadecenoic acid, stearic acid, oleic acid, and linoleic acid.
In the step 2, the molar ratio of the 1-aminoethyl-2-long carbon chain imidazoline intermediate to the ethylene oxide is 1: 5-1: 16, and the addition amount of the alkali is 0.3-0.7% of the mass of the ethylene oxide, wherein the alkali is any one of NaOH and KOH.
In the step 3, the molar ratio of the polyoxyethylene ether imidazoline to the 3-chloro-2-hydroxypropanesulfonic acid sodium salt is 1: 1.5-1: 2.0.
In the step 3, the pH value of the system is adjusted to 7.5-8.0 by using any one of NaOH and KOH.
Compared with the prior art, the invention has the beneficial effects that:
1. the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor structure of the invention introduces active groups-OH and-SO3 -Thus, multi-center adsorption with a plurality of groups simultaneously adsorbed can be formed on the surface of the metal, the adsorption activity of the metal on the surface of steel is greatly improved, excellent corrosion inhibition performance is shown, and the metal corrosion inhibitor can inhibit uniform corrosion and local corrosion.
2. The corrosion inhibitor has good water solubility, and can be applied to CO-containing2And H2S oil field produced water medium, and can be applied to CO2The corrosion to carbon steel is slowed down in a high-temperature and high-pressure medium of the oil displacement system, and the corrosion inhibition performance is excellent.
3. The corrosion inhibitor can be used independently, can be compounded with a bactericide, other corrosion inhibitors and a surfactant for use, has good biodegradability and low toxicity, and belongs to an environment-friendly corrosion inhibitor.
Drawings
FIG. 1 is an infrared spectrum of a polyoxyethylene ether imidazoline sulfonate of example 1.
FIG. 2 is an infrared spectrum of a polyoxyethylene ether imidazoline sulfonate of example 2.
FIG. 3 is an infrared spectrum of a polyoxyethylene ether imidazoline sulfonate of example 3.
Detailed Description
The present invention will be described in further detail with reference to examples, but the scope of the present invention is not limited to these examples.
Example 1
1. 56.52g (0.20mol) of 9-octadecenoic acid (formula I-1), 24.68g (0.24mol) of diethylenetriamine and 30mL of xylene are added into a 250mL reactor, heated and stirred, slowly and continuously heated, refluxed and reacted for 5h at 160-195 ℃, the dehydrated water amount is 6.22g (86.39 percent of theoretical dehydrated amount), and xylene is removed by rotary evaporation, thus obtaining a brown yellow viscous 1-aminoethyl-2- (8-heptadecenyl) imidazoline intermediate (formula II-1).
2. 69.96g (0.20mol) of the 1-aminoethyl-2- (8-heptadecenyl) imidazoline intermediate obtained in step 1 and 0.65g of sodium hydroxide were added to a reaction flask, and after evacuation of air, N was added2Stirring and heating to 110-120 ℃ under protection, slowly introducing 108.62g (2.47mol) of ethylene oxide gas, preserving heat for 38min after the ethylene oxide gas is added, stopping introducing the gas, and neutralizing the product by using 98% glacial acetic acid to obtain brown liquid 1-polyoxyethylene ether ethylamine-2- (8-heptadecenyl) imidazoline (formula III-1).
3. 175.61g (0.20mol) of the polyoxyethylene ether imidazoline obtained in the step 2 and 76.69g (0.39mol) of 3-chloro-2-hydroxypropanesulfonic acid sodium salt are added into a reaction bottle, the mixture is heated to 85-90 ℃ on a water bath, the pH value of the system is adjusted to 7.8 by using 10% NaOH aqueous solution by mass fraction, and the mixture is continuously reacted for 2.6 hours to obtain a reddish brown liquid 1, 1-polyoxyethylene ether ethylamine- (2-hydroxypropanesulfonic acid group) -2- (8-heptadecenyl) imidazoline corrosion inhibitor (formula IV-1).
Example 2
1. 58.39g (0.21mol) of octadecanoic acid (formula I-2), 22.73g (0.22mol) of diethylenetriamine and 30mL of xylene are added into a 250mL reactor, heated and stirred, slowly and continuously heated, refluxed and reacted for 4.5h at 155-190 ℃, the amount of dehydrated water is 6.48g (87.70 percent of theoretical dehydrated amount), and xylene is removed by rotary evaporation, so that a brown yellow viscous 1-aminoethyl-2-heptadecyl imidazoline intermediate (formula II-2) is obtained.
2. 72.18g (0.21mol) of the 1-aminoethyl-2-heptadecyl imidazoline intermediate obtained in step 1 and 0.86g of sodium hydroxide were added to a reaction flask, and after evacuation of air, N was added2Stirring and heating to 105-115 ℃ under protection, and slowly introducing 131.92g (3.00mol)Keeping the temperature for 42min after the addition of ethylene oxide gas, stopping introducing gas, and neutralizing the product with 98% glacial acetic acid to obtain brown liquid 1-polyoxyethylene ether ethylamine-2-heptadecyl imidazoline (formula III-2).
3. 180.56g (0.21mol) of 1-polyoxyethylene ether ethylamine-2-heptadecyl imidazoline obtained in the step 2 and 73.71g (0.38mol) of 3-chloro-2-hydroxypropanesulfonic acid sodium salt are added into a reaction bottle, the mixture is heated to 82-87 ℃ on a water bath, KOH aqueous solution with the mass fraction of 10% is used for adjusting the pH of the system to be 7.6, and the reaction is continued for 2.5 hours to obtain a red brown liquid 1, 1-polyoxyethylene ether ethylamine- (2-hydroxypropanesulfonic acid group) -2-heptadecyl imidazoline corrosion inhibitor (formula IV-2).
Example 3
1. 59.95g (0.30mol) dodecanoic acid (formula I-3), 32.69g (0.32mol) diethylenetriamine and 30mL dimethylbenzene are added into a 250mL reactor, heated and stirred, slowly and continuously heated, reflux reaction is carried out at 147-180 ℃ for 5.5h, the amount of dehydrated water is 9.52g (88.36% of theoretical dehydrated amount), and dimethylbenzene is removed by rotary evaporation, thus obtaining a brown yellow viscous 1-aminoethyl-2-undecylimidazoline intermediate (formula II-3).
2. 80.05g (0.30mol) of the intermediate 1-aminoethyl-2-undecylimidazoline, which was obtained as a brown-yellow viscous product in stage 1, and 0.43g of sodium hydroxide were added to the reaction flask, and after evacuation of the air, N was added2Stirring and heating to 100-110 ℃ under protection, slowly introducing 121.58(2.76mol) ethylene oxide gas, preserving heat for 35min after the addition is finished, stopping introducing the gas, and neutralizing the product by using 98% glacial acetic acid to obtain brown liquid 1-polyoxyethylene ether ethylamine-2-undecylimidazoline (formula III-3).
3. 238.06g (0.30mol) of 1-polyoxyethylene ether ethylamine-2-undecylimidazoline obtained in the step 2 and 89.43g (0.46mol) of sodium 3-chloro-2-hydroxypropanesulfonate are added into a reaction bottle, the mixture is heated to 85-90 ℃ on a water bath, the pH value of the system is adjusted to 7.9 by using 10 mass percent NaOH aqueous solution, and the reaction is continued for 2.2 hours to obtain a red brown liquid 1, 1-polyoxyethylene ether ethylamine- (2-hydroxypropanesulfonic acid group) -2-undecylimidazoline corrosion inhibitor (formula IV-3).
Example 4
1. 53.68g (0.21mol) hexadecenoic acid (formula I-4), 26.03g (0.25mol) diethylenetriamine and 30mL xylene were charged into a 250mL reactor, heated with stirring, slowly and continuously heated, and refluxed at 165 ℃ to 200 ℃ for 4.8 hours to remove 6.64g (87.42% based on the theoretical dehydration amount) of water, and xylene was removed by rotary evaporation to obtain a brown-yellow viscous 1-aminoethyl-2-pentadecenylimidazoline intermediate (formula II-4).
2. 67.85g (0.21mol) of the 1-aminoethyl-2-pentadecenyl imidazoline intermediate obtained in step 1 and 0.96g of sodium hydroxide were added to a reaction flask, and after evacuation of air, N was added2Stirring and heating to 102-112 ℃ under protection, slowly introducing 138.57g (3.15mol) of ethylene oxide gas, preserving heat for 45min after the addition is finished, stopping introducing the gas, and neutralizing the product by using 98% glacial acetic acid to obtain brown liquid 1-polyoxyethylene ether ethylamine-2-pentadecenyl imidazoline (formula III-4).
3. 179.25g (0.21mol) of 1-polyoxyethylene ether ethylamine-2-pentadecenyl imidazoline obtained in the step 2 and 72.42g (0.37mol) of 3-chloro-2-hydroxypropanesulfonic acid sodium salt are added into a reaction bottle, the mixture is heated to 80-85 ℃ on a water bath, the pH value of the system is adjusted to 7.5 by using 10 mass percent NaOH aqueous solution, and the reaction is continued for 2.4 hours to obtain a reddish brown liquid 1, 1-polyoxyethylene ether ethylamine- (2-hydroxypropanesulfonic acid group) -2-pentadecenyl imidazoline corrosion inhibitor (formula IV-4).
Example 5
In this example, 9-octadecenoic acid in example 1 was replaced with an equimolar amount of 9, 12-octadecadienoic acid, and the other steps were the same as in example 1 to obtain a corrosion inhibitor of 1, 1-polyoxyethylene ether-based ethylamine- (2-hydroxypropanesulfonic acid group) -2- (8, 11-heptadecadienyl) imidazoline of the following structural formula at a yield of 73%.
Example 6
In this example, the same procedure as in example 1 was repeated except for using tetradecanoic acid in an equimolar amount instead of the dodecanoic acid used in example 3 to obtain a corrosion inhibitor of 1, 1-polyoxyethylene ether ethylamine- (2-hydroxypropanesulfonic acid) -2-tridecylimidazoline having the following structural formula, which was produced at a yield of 68%.
Because the spectra obtained in the embodiments 1 to 6 are basically the same, the molecular structure of the polyoxyethylene ether imidazoline sulfonate prepared in the embodiments 1 to 3 is characterized by using a VERTEX70 type Fourier infrared spectrometer, and the infrared spectrum is shown in the figures 1 to 3.
Fig. 1 analysis of the main characteristic peaks: 2922cm-1And 2854cm-1Is represented by-CH2Has an asymmetric and symmetric telescopic vibration absorption peak of 1645cm-1C ═ N stretching vibration peak of typical imidazoline ring, which indicates that the synthesized product molecule contains imidazoline ring; from 1101cm-1The stretching vibration peak of C-O-C can judge that the synthesized product molecule contains polyether chain; in addition, 1248cm-1SO of (C)3 -The stretching vibration peak of the compound can be used for deducing that the synthesized product contains sulfonate; in conclusion, the target product is successfully synthesized.
Fig. 2 analysis of the main characteristic peaks: 2922cm-1And 2855cm-1Of (C is a-CH)2Has an asymmetric and symmetric telescopic vibration absorption peak of 1643cm-11100cm of C ═ N stretching vibration peak of imidazoline ring-1The peak of C-O-C stretching vibration at 1248cm-1SO of (C)3 -The stretching vibration peaks of the target compound all indicate that the target product is successfully synthesized.
Fig. 3 analysis of the main characteristic peaks: 2922cm-1And 2855cm-1Of (C is a-CH)2Is asymmetrical andsymmetric telescopic vibration absorption peak of 1644cm-11100cm of C ═ N stretching vibration peak of imidazoline ring-1The peak of C-O-C stretching vibration at 1248cm-1SO of (C)3 -The stretching vibration peaks of the target compound all indicate that the target product is successfully synthesized.
In order to prove the beneficial effects of the corrosion inhibitor, the inventors respectively evaluate the corrosion inhibitors prepared in examples 1-6 in the presence of only CO according to the requirements in appendix B in technical Specification for corrosion and scale inhibitors for oilfield water treatment (Q/SY 126-2The corrosion inhibition performance of the simulated on-site water on the Q235A steel sheet is shown in Table 1, wherein the temperature is 50 +/-2 ℃, the experimental time is 72 hours, the test solution amount is 1120mL, the mass concentration of the corrosion inhibitor is 50 mg/L.
TABLE 1 Corrosion inhibition Performance of polyoxyethylene ether imidazoline sulfonate corrosion inhibitor under static state
As can be seen from Table 1, only CO is contained2In the field simulation water, the uniform corrosion rate of the corrosion inhibitor prepared in the embodiments 1 to 6 of the invention on the Q235A steel sheet is far lower than that of a blank solution, and the corrosion inhibition performance meets the index requirements.
In order to further prove the high-temperature and high-pressure performance of the corrosion inhibitor, the inventor refers to the industrial standard 'performance index and evaluation method of corrosion inhibitor for water treatment of oilfield production' (SY/T5273-4mg/L of water in certain oil field layer to simulate CO2Oil displacement process conditions (temperature 60 ℃, CO)2Partial pressure of 6.0MPa), the corrosion inhibition performance of the corrosion inhibitor on N80 steel is tested when the mass concentration of the corrosion inhibitor is 100mg/L, the time is 72h, and the experimental results are shown in Table 2.
TABLE 2 polyoxyethylene ether imidazoline sulfonate corrosion inhibitor in CO2Corrosion inhibition performance under oil displacement process condition
As can be seen from Table 2, in simulating CO2Under the condition of an oil displacement process, the uniform corrosion rate of the corrosion inhibitor prepared in the embodiments 1 to 6 of the invention on the N80 steel sheet is far lower than that of a blank solution, and the corrosion inhibition rate of the corrosion inhibitor relative to the blank solution is more than 90%, which shows that the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor has good corrosion inhibition performance in a high-temperature high-pressure medium.
Claims (7)
1. A polyoxyethylene ether imidazoline sulfonate corrosion inhibitor is characterized in that the corrosion inhibitor has the following structural formula:
wherein R represents any one of undecyl, 4-undecenyl, tridecyl, pentadecyl, pentadecenyl, 8, 11-pentadecenyl, 9-hexadecenyl, heptadecyl, 8-heptadecenyl and 8, 11-heptadecenyl, and n is an integer of 5-15.
2. A method for preparing the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor of claim 1, which is characterized in that:
(1) refluxing and reacting long-carbon-chain carboxylic acid shown in a formula I and diethylenetriamine at 140-200 ℃ for 4-6 h by using dimethylbenzene as a solvent, and removing the dimethylbenzene by rotary evaporation when the dehydration amount is more than 85% of the theoretical dehydration amount to obtain a 1-aminoethyl-2-long-carbon-chain imidazoline intermediate shown in a formula II; the long-carbon-chain carboxylic acid is any one of lauric acid, 5-dodecenoic acid, myristic acid, palmitic acid, 2-hexadecenoic acid, 9, 12-hexadecadienyl, 10-heptadecenoic acid, stearic acid, oleic acid and linoleic acid;
(2) the 1-aminoethyl-2-long carbon chain imidazoline intermediate obtained in the step (1) and alkali are added into N2Stirring and heating to 100-120 ℃ under protection, introducing ethylene oxide gas, continuing stirring at constant temperature for 30-45 min, stopping introducing the gas, and separating and purifying to obtain polyoxyethylene ether imidazoline shown in formula III;
(3) heating the polyoxyethylene ether imidazoline obtained in the step (2) and 3-chloro-2-hydroxypropanesulfonic acid sodium salt to 80-90 ℃, adjusting the pH of the system to 7.5-8.0, and then continuing to react for 2-3 hours to obtain the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor shown in the formula IV.
3. The method for preparing the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor according to claim 2, wherein the method comprises the following steps: in the step (1), the molar ratio of the long carbon chain carboxylic acid to diethylenetriamine is 1:1.05 to 1: 1.20.
4. The method for preparing the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor according to claim 2, wherein the method comprises the following steps: in the step (2), the molar ratio of the 1-aminoethyl-2-long carbon chain imidazoline intermediate to the ethylene oxide is 1: 5-1: 16, and the addition amount of the alkali is 0.3-0.7% of the mass of the ethylene oxide.
5. The method for preparing the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor according to claim 2 or 4, wherein the method comprises the following steps: the alkali is any one of NaOH and KOH.
6. The method for preparing the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor according to claim 2, wherein the method comprises the following steps: in the step (3), the molar ratio of the polyoxyethylene ether imidazoline to the 3-chloro-2-hydroxypropanesulfonic acid sodium salt is 1: 1.5-1: 2.0.
7. The method for preparing the polyoxyethylene ether imidazoline sulfonate corrosion inhibitor according to claim 2, wherein the method comprises the following steps: in the step (3), the pH value of the system is adjusted to 7.5-8.0 by any one of NaOH and KOH.
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