CN103555313A - Imidazolium salt ionic liquid acidizing corrosion inhibitor as well as preparation method and application thereof - Google Patents
Imidazolium salt ionic liquid acidizing corrosion inhibitor as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to an imidazolium salt ionic liquid acidizing corrosion inhibitor as well as a preparation method and application thereof. The imidazolium salt ionic liquid corrosion inhibitor is a compound with the structure of a general formula I. The preparation method comprises steps of firstly synthesizing a N-alkyl imidazole intermediate through imidazole and bromo-n-alkane, and carrying out reaction on the N-alkyl imidazole intermediate and the bromo-n-alkane so as to prepare the imidazolium salt ionic liquid corrosion inhibitor. The imidazolium salt ionic liquid which is taken as the acidizing corrosion inhibitor is used in oil well acidization at the temperature more than or equal to 60 DEG C, so as to prevent acid liquor from corroding pipelines, metallic equipment and down-hole pipe columns.
Description
Technical field
The present invention relates to a kind of imidazole salts ionic liquid acidification corrosion inhibitor and preparation method thereof and application, belong to oilfield chemical inhibiter technical field.
Background technology
Inhibiter, as a kind of economic and practical and efficient anti-corrosion method, is playing an important role aspect reserved resource, minimizing material unaccounted-for (MUF).In the last few years, the needs based on environment protection and the strategy of sustainable development, eco-friendly inhibiter becomes the important directions of following inhibiter development.Existing inhibiter all has toxic side effect mostly, in production and use procedure, operator and ecotope is existed to larger harm, does not meet the demand for development of current Green Chemistry.Ionic liquid does not almost have vapour pressure, non-volatile, colourless, tasteless; There is larger equilibrium temperature scope and good chemical stability; Simultaneously very easily water-soluble " green corrosion inhibitor " that is expected to become a new generation.Initial ionic liquid is mainly used in electrochemical research, at present, the applied research of ionic liquid is mainly concentrated on to the fields such as letex polymerization, separating-purifying, desulfurization, chromatogram and biological enzyme reaction, also fewer for research and the relevant report in its inhibiter field.Wang Yue has reported the corrosion behavior (Anhui chemical industry, 2009, the 35 volumes, the 2nd phase) of aluminium foil under the effect of chain alkyl imidazoles, and result shows that temperature, concentration of hydrochloric acid and chain alkyl imidazole concentration have important impact to aluminium foil corrosion.Gaoyang report has synthesized the N-alkyl benzimidazole positively charged ion (NBIC) of a series of different chain length, and has studied at 40 ℃ of temperature it to the corrosion inhibition of carbon steel and the mechanism of action (material protection, 2009, the 42 volumes, the 7th phase).The imidazole salts ionic liquid of having reported as iron and steel inhibiter at low temperatures (50 ℃ of <) there is good corrosion inhibition, inhibiter performance report not under 50 ℃ of above high temperature.
Summary of the invention
For the deficiencies in the prior art, the invention provides a kind of eco-friendly imidazole salts ionic liquid acidification corrosion inhibitor, the present invention also provides its preparation method and application.
The inventor has investigated imidazole salts ionic liquid corrosion inhibition at high temperature, and has explored the relation of chain alkyl imidazole salts ionic liquid carbon chain lengths and corrosion inhibition, proposes the present invention.
Technical scheme of the present invention is as follows:
An ionic liquid inhibiter is the compound with following general formula I structure:
In formula I: R
1represent the short chain alkanes of C1-C6, R
2the long chain alkane that represents C10～C20, Br represents bromo element, N represents nitrogen element.
Preferred R
1for-CH
3,-C
2h
5,-C
4h
9.
According to the present invention, preferred R
2for-C
10h
23,-C
12h
25,-C
14h
29,-C
16h
33,-C
18h
37.
According to the present invention, preferably, the compound of general formula I structure is 1-dodecyl-3-Methylimidazole bromine salt, 1-tetradecyl-3-Methylimidazole bromine, 1-hexadecyl-3-Methylimidazole bromine, 1-octadecyl-3-Methylimidazole bromine, 1-ten alkyl-3-imidazole-butyl bromide salt, 1-tetradecyl-3-imidazole-butyl bromide salt, 1-hexadecyl-3-imidazole-butyl bromide salt.
Further preferably, the compound of general formula I structure is 1-octadecyl-3-Methylimidazole bromine.
According to the present invention, the preparation method of described imidazole salts ionic liquid inhibiter, comprises that step is as follows:
The first step: imidazoles and bromo normal alkane I are joined in autoclave by 2～4:1 mol ratio, and described bromo normal alkane I chemical formula is C
nh
2n+1br, wherein 2≤n≤6; Add ethyl acetate, wherein ethyl acetate add-on is imidazoles and the total mol ratio of bromo normal alkane 15～20 times.Autoclave sealing is placed in thermostatic drying chamber, at 80～120 ℃, react 15～16h, after being cooled to 0 ℃, filters reacted product, by filtered product with after re-crystallizing in ethyl acetate, with the mixed solvent of first benzene and heptane, wash 2 times, remove unreacted imidazoles and bromo normal alkane.Product after purification dry 6h in the vacuum drying oven of 80 ℃ obtains N-alkyl imidazole intermediate C
n+3h
2n+4n
2, 2≤n≤6;
Second step: N-alkyl imidazole intermediate and the bromo normal alkane II of N-Methylimidazole or the first step reaction preparation are joined in autoclave by 1:1～1.2 mol ratio, and described bromo normal alkane II chemical formula is C
nh
2n+1br, wherein 10≤n≤20; Add ethyl acetate solvent, wherein ethyl acetate add-on is N-Methylimidazole or N-alkyl imidazole intermediate and the total mol ratio of bromo normal alkane II 15～20 times.Autoclave sealing is placed in thermostatic drying chamber, at 130 ℃, reacts 10～16h, obtain crude product, crude product obtains corresponding chain alkyl imidazole salts ionic liquid after purifying by toluene wash.
According to the present invention, preferred, first benzene and heptane volume ratio 1:4 in the mixed solvent of first benzene and heptane described in the first step;
According to the present invention, preferred, the purifying described in second step is that washing or distillation method are removed ethyl acetate, obtains the chain alkyl imidazole salts ionic liquid of purity >=99%.
Reaction scheme of the present invention is as follows:
The first step:
Second step:
Along with oil, the carrying out of natural gas exploration and development, usually needs to improve recovery ratio by acidifying.Yet in acidization, the injection of acid may cause the heavy corrosion of Oil/gas Well tubing and down-hole hardware.At present, the most frequently used anti-corrosion method in each oil field adds inhibiter exactly, not only economical and effective but also do not affect the normal production in oil field.
The application of imidazole salts ionic liquid of the present invention in oil field, it is characterized in that, described imidazole salts ionic liquid as acidification corrosion inhibitor under ℃ hot conditions of temperature >=60 for oil well acidation process, prevent the corrosion of acid solution to pipeline, hardware and down-hole string.Its inhibition mechanism is that inhibiter can form coordinate bond with metallic surface chemisorption occurs.Inhibiter is with its absorption of hydrophilic group and metallic surface, and hydrophobic grouping, away from metallic surface, forms adsorption layer metal active center is covered, and stops medium to corrosion of metal.
The application of imidazole salts ionic liquid of the present invention in oil field, is characterized in that, described imidazole salts ionic liquid joined in oil well acidation system, and pH<1, the concentration that makes imidazole salts ionic liquid is 150-250mg/L.
Further preferred, when imidazole salts ionic liquid inhibiter mass concentration of the present invention is 200mg/L, in the HCl environment that is 10-20% at massfraction, can suppress preferably the corrosion of N80 steel disc.Slowly-releasing efficiency can reach 87-94%.
Further preferred, imidazole salts ionic liquid inhibiter of the present invention, under temperature 70 C hot conditions, in oil well acidation process, 1-octadecyl-3-Methylimidazole bromine is best to the inhibition corrosive power of pipeline, hardware and down-hole string.
Excellent results of the present invention:
Synthetic ionic liquid inhibiter is that in 20%HCl medium, to N80 steel disc, corrosion has good inhibition at massfraction.When the mass concentration of inhibiter is 200mg/L, in the time of 70 ℃, in 12%HCl environment, corrode 8h, its erosion rate is 15.23g/m
2.h, slowly-releasing efficiency can reach 92.54%.When the mass concentration of inhibiter is 200mg/L, in the time of 70 ℃, in 20%HCl environment, corrode 8h, its erosion rate is 26.20g/m
2.h, slowly-releasing efficiency can reach 87.17%.The feature of this inhibiter is that in molecule, the nitrogen-atoms on heterocycle contains lone-pair electron, can in metallic surface, form absorption, form organic molecular film, suppress steel corrosion, in imidazole molecule, contain long-chain substituted alkyl simultaneously, thereby can form, there is certain thickness molecular film assurance corrosion inhibition.Compare with the organic and inorganic inhibitor of routine, ionic liquid does not have toxic action to environment and biology, environmental protection as inhibiter.The application of chain alkyl imidazole salts ionic liquid in acidification corrosion inhibitor, has solved the large deficiency of existing inhibiter toxic side effect.
Accompanying drawing explanation
Fig. 1 is that concentration is the imidazole ion liquid of different alkyl chain lengths of the 200mg/L polarization curve of 50 ℃ in 12% hydrochloric acid, wherein, and 1, do not add the blank contrast of inhibiter; 2,1-dodecyl-3-Methylimidazole bromine; 3,1-tetradecyl-3-Methylimidazole bromine; 4,1-hexadecyl-3-Methylimidazole bromine; 5,1-octadecyl-3-Methylimidazole bromine.
Embodiment
Below in conjunction with the accompanying drawing of embodiment, the present invention is further described, but be not limited to this.The raw materials used commercially available prod that is of embodiment.
The preparation method of embodiment 1:1-dodecyl-3-Methylimidazole bromine salt ion liquid
N-Methylimidazole 0.82g and 2.5g N-dodeeyl bromide are joined in 100mL autoclave, add 28g ethyl acetate solvent, to after autoclave sealing, put into thermostat container, at 130 ℃, react 10h, obtain crude product, crude product obtains 1-dodecyl-3-Methylimidazole bromine salt ion liquid after purifying by toluene wash.
The preparation method of embodiment 2:1-tetradecyl-3-Methylimidazole bromine salt ion liquid
N-Methylimidazole 0.82g and 3.6g bromo n-tetradecane are joined in 100mL autoclave, add 30g ethyl acetate solvent, to after autoclave sealing, put into thermostat container, at 130 ℃, react 10h, obtain crude product, crude product obtains 1-tetradecyl-3-Methylimidazole bromine salt ion liquid after purifying by toluene wash.
The preparation method of embodiment 3:1-hexadecyl-3-Methylimidazole bromine salt ion liquid
N-Methylimidazole 0.82g and 4.4g bromo n-tetradecane are joined in 100mL autoclave, add 30g ethyl acetate solvent, to after autoclave sealing, put into thermostat container, at 130 ℃, react 16h, obtain crude product, crude product obtains 1-hexadecyl-3-Methylimidazole bromine salt ion liquid after purifying by toluene wash.
The preparation method of embodiment 4:1-octadecyl-3-Methylimidazole bromine salt ion liquid
N-Methylimidazole 0.82g and 4.6g bromo Octadecane are joined in 100mL autoclave, add 32g ethyl acetate solvent, to after autoclave sealing, put into thermostat container, at 130 ℃, react 16h, obtain crude product, crude product obtains 1-octadecyl-3-Methylimidazole bromine salt ion liquid after purifying by toluene wash.
The preparation method of embodiment 5:1-ten alkyl-3-imidazole-butyl bromide salt ion liquid
Imidazoles 1.36g and bromination of n-butane hydrocarbon 1.32g are joined in autoclave, add 42g ethyl acetate solvent, autoclave sealing is placed in thermostatic drying chamber, at 80 ℃, react 15h, after being cooled to 0 ℃, filters reacted product, filtered product, with after re-crystallizing in ethyl acetate, is washed 2 times with the mixed solvent (first benzene and heptane volume ratio 1:4) of first benzene and heptane, remove unreacted imidazoles and bromination of n-butane hydrocarbon.Then the dry 6h in the vacuum drying oven of 80 ℃ of the product after purifying obtains N-butyl imidazole intermediate C
n+3h
2n+4n
2, n=4;
The N-butyl imidazole intermediate 0.82g of described preparation and 2.2g bromo decane are joined in 100mL autoclave, add 28g ethyl acetate solvent, to after autoclave sealing, put into thermostat container, at 130 ℃, react 10h, obtain crude product, crude product obtains 1-ten alkyl-3-imidazole-butyl bromide salt ion liquid after purifying by toluene wash.
The preparation method of embodiment 6:1-tetradecyl-3-imidazole-butyl bromide salt ion liquid
Imidazoles 1.36g and bromination of n-butane hydrocarbon 1.32g are joined in autoclave, add 42g ethyl acetate solvent, autoclave sealing is placed in thermostatic drying chamber, at 80 ℃, react 15h, after being cooled to 0 ℃, filters reacted product, filtered product, with after re-crystallizing in ethyl acetate, is washed 2 times with the mixed solvent (first benzene and heptane volume ratio 1:4) of first benzene and heptane, remove unreacted imidazoles and bromination of n-butane hydrocarbon.Then the dry 6h in the vacuum drying oven of 80 ℃ of the product after purifying obtains N-butyl imidazole intermediate C
n+3h
2n+4n
2, n=4; .
N-butyl imidazole intermediate 0.82g and 2.6g bromo n-tetradecane are joined in 100mL autoclave, add 32g ethyl acetate solvent, to after autoclave sealing, put into thermostat container, at 130 ℃, react 14h, obtain crude product, crude product obtains 1-tetradecyl-3-imidazole-butyl bromide salt ion liquid after purifying by toluene wash.
Embodiment 7: static steel weight-loss method is measured the corrosion inhibition of imidazole salts ionic liquid inhibiter
In order to check corrosion mitigating effect of the present invention, by static steel weight-loss method, the corrosion inhibition of the resulting ionic liquid inhibiter of embodiment 1～6 is evaluated, experiment test specimen is N-80 steel disc, and temperature of reaction is 70 ℃, test duration is 8 hours, and experimental result is as shown in table 1～3.
In table 112%HCl, add 200mg.L
-1steel disc erosion rate and corrosion inhibition rate after ionic liquid inhibiter
| Sample | Erosion rate (g/m 2.h) | Corrosion inhibition rate (%) |
| Do not add inhibiter (12% hydrochloric acid is done blank contrast) | 204.28 | —— |
| 1-dodecyl-3-Methylimidazole bromine salt ion liquid | 69.95 | 65.76 |
| 1-tetradecyl-3-Methylimidazole bromine salt ion liquid | 17.56 | 91.41 |
| 1-hexadecyl-3-Methylimidazole bromine salt ion liquid | 17.34 | 91.51 |
| 1-octadecyl-3-Methylimidazole bromine salt ion liquid | 15.23 | 92.54 |
| 1-ten alkyl-3-imidazole-butyl bromide salt ion liquid | 14.55 | 92.88 |
| 1-tetradecyl-3-imidazole-butyl bromide salt ion liquid | 13.69 | 93.35 |
Under the different HCl concentration of table 2, add 200mg.L
-1erosion rate after inhibiter
The corrosion inhibition of table 31-hexadecyl-3-Methylimidazole bromine salt ion liquid in 12%HCl solution
Embodiment 8: potentiostatic polarization curve method is evaluated imidazole salts ionic liquid inhibiter corrosion inhibition
With reference to the potentiostatic polarization curve method in oil and gas industry standard SY/5273-1991, evaluate the corrosion inhibition of inhibiter.In the HCl solution that is 12% at 300mL massfraction, adding respectively concentration is 200mg.L
-11-ten alkyl-3-Methylimidazole bromine, 1-dodecyl-3-Methylimidazole bromine, 1-tetradecyl-3-Methylimidazole bromine, 1-hexadecyl-3-Methylimidazole bromine, 1-octadecyl-3-Methylimidazole bromine inhibiter, then add Q235 steel disc to carry out electro-chemical test.Polarization curve test result as shown in Figure 1, the corrosion current that adds of inhibiter significantly reduces, show that inhibiter has reduced the corrosion of 12%HCl to Q235 steel disc effectively, simultaneously along with chain alkyl imidazole salts ionic liquid carbochain lengthens, the corrosion potential of system is shuffled, anodic polarization rate increases, and the corrosion that shows antianode has stronger restraining effect.Simultaneous verification the experiment conclusion that draws of weight loss method: if polar group is identical, when the carbon chain lengths of non-polar group (as alkyl) is different, lengthening along with chain alkyl imidazole salts ionic liquid carbochain, ionic liquid suppresses corrosive power to be strengthened gradually, and the inhibition corrosive power of 1-octadecyl-3-Methylimidazole bromine is best.
Claims (9)
1. an imidazole salts ionic liquid inhibiter is the compound with following general formula I structure:
In formula I: R
1represent the short chain alkanes of C1-C6, R
2the long chain alkane that represents C10～C20, Br represents bromo element, N represents nitrogen element.
2. imidazole salts ionic liquid inhibiter as claimed in claim 1, is characterized in that the R in formula I
1for-CH
3,-C
2h
5,-C
4h
9; R
2for-C
10h
23,-C
12h
25,-C
14h
29,-C
16h
33,-C
18h
37.
3. imidazole salts ionic liquid inhibiter as claimed in claim 1, it is characterized in that, the compound of general formula I structure is 1-dodecyl-3-Methylimidazole bromine salt, 1-tetradecyl-3-Methylimidazole bromine, 1-hexadecyl-3-Methylimidazole bromine, 1-octadecyl-3-Methylimidazole bromine, 1-ten alkyl-3-imidazole-butyl bromide salt, 1-tetradecyl-3-imidazole-butyl bromide salt, 1-hexadecyl-3-imidazole-butyl bromide salt.
4. the preparation method of the imidazole salts ionic liquid inhibiter described in claim 1～3 any one, comprises that step is as follows:
The first step: imidazoles and bromo normal alkane I are joined in autoclave by 2～4:1 mol ratio, and described bromo normal alkane I chemical formula is C
nh
2n+1br, wherein 2≤n≤6; Add ethyl acetate, wherein ethyl acetate add-on is imidazoles and the total mol ratio of bromo normal alkane 15～20 times.Autoclave sealing is placed in thermostatic drying chamber, at 80～120 ℃, react 15～16h, after being cooled to 0 ℃, filters reacted product, by filtered product with after re-crystallizing in ethyl acetate, with the mixed solvent of first benzene and heptane, wash 2 times, remove unreacted imidazoles and bromo normal alkane.Product after purification dry 6h in the vacuum drying oven of 80 ℃ obtains N-alkyl imidazole intermediate C
n+3h
2n+4n
2, 2≤n≤6;
Second step: N-alkyl imidazole intermediate and the bromo normal alkane II of N-Methylimidazole or the first step reaction preparation are joined in autoclave by 1:1～1.2 mol ratio, and described bromo normal alkane II chemical formula is C
nh
2n+1br, wherein 10≤n≤20; Add ethyl acetate solvent, wherein ethyl acetate add-on is N-Methylimidazole or N-alkyl imidazole intermediate and the total mol ratio of bromo normal alkane II 15～20 times; Autoclave sealing is placed in thermostatic drying chamber, at 130 ℃, reacts 10～16h, obtain crude product, crude product obtains corresponding chain alkyl imidazole salts ionic liquid after purifying by toluene wash.
5. the preparation method of imidazole salts ionic liquid inhibiter as claimed in claim 4, is characterized in that first benzene and heptane volume ratio 1:4 in the mixed solvent of first benzene and heptane described in the first step.
6. the application of the imidazole salts ionic liquid described in claim 1～3 any one in oil field, described imidazole salts ionic liquid as acidification corrosion inhibitor under ℃ hot conditions of temperature >=60 for oil well acidation process, for preventing the corrosion of acid solution to pipeline, hardware and down-hole string.
7. the application of imidazole salts ionic liquid as claimed in claim 6 in oil field, is characterized in that, described imidazole salts ionic liquid joined in oil well acidation system, and pH<1, the concentration that makes imidazole salts ionic liquid is 150-250mg/L.
8. the application of imidazole salts ionic liquid as claimed in claim 6 in oil field, is characterized in that, when described imidazole salts ionic liquid inhibiter mass concentration is 200mg/L, suppresses the corrosion of N80 steel disc at massfraction in the HCl environment that is 10-20%.
9. the application of imidazole salts ionic liquid as claimed in claim 6 in oil field, it is characterized in that, under temperature 70 C hot conditions, in oil well acidation process, the 1-octadecyl-3-Methylimidazole bromine in described imidazole salts ionic liquid inhibiter is best to the inhibition corrosive power of pipeline, hardware and down-hole string.
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| CN104532254A (en) * | 2014-12-17 | 2015-04-22 | 天津工业大学 | Composite ionic liquid steel corrosion inhibitor and application |
| CN105038739A (en) * | 2015-07-15 | 2015-11-11 | 中国地质大学（北京） | Drilling fluid and use of imidazole ionic liquid therein |
| CN106047328A (en) * | 2016-07-11 | 2016-10-26 | 扬州大学 | Nano-emulsion corrosion inhibitor containing imidazolyl ionic liquid and preparation method of nano-emulsion corrosion inhibitor containing imidazolyl ionic liquid |
| CN109705770A (en) * | 2019-01-11 | 2019-05-03 | 成都其其小数科技有限公司 | A kind of elastic conduction microballoon and preparation method for anisotropic conductive film |
| WO2020014534A1 (en) * | 2018-07-11 | 2020-01-16 | Baker Hughes, A Ge Company, Llc | Methods of using ionic liquids as corrosion inhibitors |
| CN111607373A (en) * | 2020-05-06 | 2020-09-01 | 中国石油天然气集团有限公司 | Corrosion inhibitor for oil-gas field gathering and transportation pipeline capable of resisting corrosion of high-calcium produced water |
| CN113026024A (en) * | 2021-03-08 | 2021-06-25 | 吉林化工学院 | Mixed ionic liquid corrosion inhibitor and preparation method and application thereof |
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| WO2023124953A1 (en) * | 2021-12-31 | 2023-07-06 | 中国石油天然气股份有限公司 | Bactericidal corrosion inhibitor as well as preparation method therefor and use thereof |
| CN116657143A (en) * | 2023-07-17 | 2023-08-29 | 四川冠山科技有限公司 | Green corrosion inhibitor for inhibiting corrosion of low-carbon steel in high-concentration hydrochloric acid medium and preparation method thereof |
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