CN103555313B - A kind of imidazolium ionic liquid acidification corrosion inhibitor and preparation method thereof and application - Google Patents
A kind of imidazolium ionic liquid acidification corrosion inhibitor and preparation method thereof and application Download PDFInfo
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- CN103555313B CN103555313B CN201310545698.0A CN201310545698A CN103555313B CN 103555313 B CN103555313 B CN 103555313B CN 201310545698 A CN201310545698 A CN 201310545698A CN 103555313 B CN103555313 B CN 103555313B
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- imidazolium ionic
- normal alkane
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/72—Eroding chemicals, e.g. acids
- C09K8/74—Eroding chemicals, e.g. acids combined with additives added for specific purposes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/32—Anticorrosion additives
Abstract
The present invention relates to a kind of imidazolium ionic liquid acidification corrosion inhibitor and preparation method thereof and application.Described imidazolium ionic liquid inhibiter is the compound with following general formula I.First synthesize N-alkyl imidazole intermediate by imidazoles and bromo normal alkane, then react obtained imidazolium ionic liquid inhibiter with bromo normal alkane.Described imidazolium ionic liquid as acidification corrosion inhibitor under DEG C hot conditions of temperature >=60 in oil well acidation process, for preventing acid solution to the corrosion of pipeline, hardware and down-hole string.
Description
Technical field
The present invention relates to a kind of imidazolium ionic liquid acidification corrosion inhibitor and preparation method thereof and application, belong to oilfield chemical inhibiter technical field.
Background technology
Inhibiter is economic and practical and efficient anti-corrosion method as one, plays an important role in reserved resource, minimizing material unaccounted-for (MUF).In the last few years, based on the needs of 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, there is larger harm, do not meet the demand for development of current Green Chemistry in production and use procedure to operator and ecotope.Ionic liquid does not almost have vapour pressure, non-volatile, colourless, tasteless; There is larger equilibrium temperature scope and good chemical stability; Very easily water-soluble being expected to becomes " green corrosion inhibitor " of new generation simultaneously.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, for the research in its inhibiter field and relevant report also fewer.Wang Yue reports the corrosion behavior (Anhui chemical industry, the 2009,35th volume, 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 under have studied 40 DEG C of temperature its to the corrosion inhibition of carbon steel and the mechanism of action (material protection, the 2009,42nd volume, the 7th phase).The imidazolium ionic liquid reported as iron and steel inhibiter at low temperatures (< 50 DEG C) there is excellent corrosion inhibition, under more than 50 DEG C high temperature, inhibiter performance is not then reported.
Summary of the invention
For the deficiencies in the prior art, the invention provides a kind of eco-friendly imidazolium ionic liquid acidification corrosion inhibitor, the present invention also provides its preparation method and application.
The present inventor has investigated imidazolium ionic liquid corrosion inhibition at high temperature, and explores the relation of chain alkyl imidazolium ionic liquid carbon chain lengths and corrosion inhibition, proposes the present invention.
Technical scheme of the present invention is as follows:
A kind of imidazolium ionic liquid inhibiter is the compound with following general formula I:
In formula I: R
1represent the short chain alkanes of C1-C6, R
2represent the long chain alkane of C10 ~ C20, Br represents bromo element, and 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 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 is 1-octadecyl-3-Methylimidazole bromine.
According to the present invention, the preparation method of described imidazolium ionic liquid inhibiter, comprises step as follows:
The first step: join in autoclave by 2 ~ 4:1 mol ratio by imidazoles and bromo normal alkane I, 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 15 ~ 20 times of imidazoles and the total mol ratio of bromo normal alkane.Autoclave sealing is placed in thermostatic drying chamber, 15 ~ 16h is reacted at 80 ~ 120 DEG C, filter after reacted product is cooled to 0 DEG C, after filtered product re-crystallizing in ethyl acetate, wash 2 times with the mixed solvent of first benzene and heptane, remove unreacted imidazoles and bromo normal alkane.Product after purification dry 6h in the vacuum drying oven of 80 DEG C obtains N-alkyl imidazole intermediate C
n+3h
2n+4n
2, 2≤n≤6;
Second step: the N-alkyl imidazole intermediate prepare N-Methylimidazole or the first step reaction and bromo normal alkane II join 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 15 ~ 20 times of N-Methylimidazole or N-alkyl imidazole intermediate and the total mol ratio of bromo normal alkane II.Autoclave sealing is placed in thermostatic drying chamber, at 130 DEG C, reacts 10 ~ 16h, obtain crude product, after crude product toluene wash purifying, obtain corresponding chain alkyl imidazolium ionic liquid.
According to the present invention, preferably, 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, preferably, the purifying described in second step is that washing or distillation method remove ethyl acetate, obtains the chain alkyl imidazolium 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.But 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 imidazolium ionic liquid of the present invention in oil field, it is characterized in that, described imidazolium ionic liquid as acidification corrosion inhibitor under DEG C hot conditions of temperature >=60 in oil well acidation process, prevent acid solution to the corrosion of 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 and metal active centres is covered, and stops medium to corrosion of metal.
The application of imidazolium ionic liquid of the present invention in oil field, is characterized in that, described imidazolium ionic liquid is joined in oil well acidation system, pH<1, makes the concentration of imidazolium ionic liquid be 150-250mg/L.
Preferred further, when imidazolium ionic liquid inhibiter mass concentration of the present invention is 200mg/L, be the corrosion that can suppress N80 steel disc in the HCl environment of 10-20% preferably at massfraction.Slowly-releasing efficiency can reach 87-94%.
Preferred further, imidazolium ionic liquid inhibiter of the present invention, under temperature 70 C hot conditions in oil well acidation process, the suppression corrosive power of 1-octadecyl-3-Methylimidazole bromine to pipeline, hardware and down-hole string is best.
Excellent results of the present invention:
The ionic liquid inhibiter of synthesis is have good inhibition to the corrosion of N80 steel disc in 20%HCl medium at massfraction.When the mass concentration of inhibiter is 200mg/L, 70 DEG C time, corrode 8h in 12%HCl environment, 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, 70 DEG C time, corrode 8h in 20%HCl environment, its erosion rate is 26.20g/m
2.h, slowly-releasing efficiency can reach 87.17%.The feature of this inhibiter is that the nitrogen-atoms in molecule on heterocycle contains lone-pair electron, absorption can be formed in metallic surface, form organic molecular film, suppress steel corrosion, contain long-chain substituted alkyl in imidazole molecule simultaneously, can be formed and there is certain thickness molecular film thus ensure corrosion inhibition.Compare with inorganic inhibitor with the organic of routine, ionic liquid is used as inhibiter does not have toxic action to environment and biology, environmental protection.The application of chain alkyl imidazolium ionic liquid in acidification corrosion inhibitor, solves the deficiency that existing inhibiter toxic side effect is large.
Accompanying drawing explanation
The imidazole ion liquid of Fig. 1 to be concentration be different alkyl chain lengths of the 200mg/L polarization curve of 50 DEG C in 12% hydrochloric acid, wherein, 1, do not add the blank 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 thereto.Embodiment is raw materials used is commercially available prod.
The preparation method of embodiment 1:1-dodecyl-3-Methylimidazole bromine ionic liquid
N-Methylimidazole 0.82g and 2.5g N-dodeeyl bromide are joined in 100mL autoclave, add 28g ethyl acetate solvent, thermostat container is put into after being sealed by autoclave, 10h is reacted at 130 DEG C, obtain crude product, after crude product toluene wash purifying, obtain 1-dodecyl-3-Methylimidazole bromine ionic liquid.
The preparation method of embodiment 2:1-tetradecyl-3-Methylimidazole bromine ionic liquid
N-Methylimidazole 0.82g and 3.6g bromo n-tetradecane are joined in 100mL autoclave, add 30g ethyl acetate solvent, thermostat container is put into after being sealed by autoclave, 10h is reacted at 130 DEG C, obtain crude product, after crude product toluene wash purifying, obtain 1-tetradecyl-3-Methylimidazole bromine ionic liquid.
The preparation method of embodiment 3:1-hexadecyl-3-Methylimidazole bromine ionic liquid
N-Methylimidazole 0.82g and 4.4g bromo n-tetradecane are joined in 100mL autoclave, add 30g ethyl acetate solvent, thermostat container is put into after being sealed by autoclave, 16h is reacted at 130 DEG C, obtain crude product, after crude product toluene wash purifying, obtain 1-hexadecyl-3-Methylimidazole bromine ionic liquid.
The preparation method of embodiment 4:1-octadecyl-3-Methylimidazole bromine ionic liquid
N-Methylimidazole 0.82g and 4.6g bromo Octadecane are joined in 100mL autoclave, add 32g ethyl acetate solvent, thermostat container is put into after being sealed by autoclave, 16h is reacted at 130 DEG C, obtain crude product, after crude product toluene wash purifying, obtain 1-octadecyl-3-Methylimidazole bromine ionic liquid.
The preparation method of embodiment 5:1-ten alkyl-3-imidazole-butyl bromide ionic liquid
Imidazoles 1.36g and bromination of n-butane hydrocarbon 1.32g is joined in autoclave, add 42g ethyl acetate solvent, autoclave sealing is placed in thermostatic drying chamber, 15h is reacted at 80 DEG C, filter after reacted product is cooled to 0 DEG C, after filtered product re-crystallizing in ethyl acetate, wash 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 product dry 6h in the vacuum drying oven of 80 DEG C 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, thermostat container is put into after being sealed by autoclave, 10h is reacted at 130 DEG C, obtain crude product, after crude product toluene wash purifying, obtain 1-ten alkyl-3-imidazole-butyl bromide ionic liquid.
The preparation method of embodiment 6:1-tetradecyl-3-imidazole-butyl bromide ionic liquid
Imidazoles 1.36g and bromination of n-butane hydrocarbon 1.32g is joined in autoclave, add 42g ethyl acetate solvent, autoclave sealing is placed in thermostatic drying chamber, 15h is reacted at 80 DEG C, filter after reacted product is cooled to 0 DEG C, after filtered product re-crystallizing in ethyl acetate, wash 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 product dry 6h in the vacuum drying oven of 80 DEG C 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, thermostat container is put into after being sealed by autoclave, 14h is reacted at 130 DEG C, obtain crude product, after crude product toluene wash purifying, obtain 1-tetradecyl-3-imidazole-butyl bromide ionic liquid.
Embodiment 7: static steel weight-loss method measures the corrosion inhibition of imidazolium ionic liquid inhibiter
In order to check corrosion mitigating effect of the present invention, evaluate with the corrosion inhibition of static steel weight-loss method to the ionic liquid inhibiter that embodiment 1 ~ 6 obtains, experiment test specimen is N-80 steel disc, and temperature of reaction is 70 DEG C, test duration is 8 hours, and experimental result is as shown in table 1 ~ 3.
200mg.L is added in table 112%HCl
-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 blank) | 204.28 | —— |
| 1-dodecyl-3-Methylimidazole bromine ionic liquid | 69.95 | 65.76 |
| 1-tetradecyl-3-Methylimidazole bromine ionic liquid | 17.56 | 91.41 |
| 1-hexadecyl-3-Methylimidazole bromine ionic liquid | 17.34 | 91.51 |
| 1-octadecyl-3-Methylimidazole bromine ionic liquid | 15.23 | 92.54 |
| 1-ten alkyl-3-imidazole-butyl bromide ionic liquid | 14.55 | 92.88 |
| 1-tetradecyl-3-imidazole-butyl bromide ionic liquid | 13.69 | 93.35 |
200mg.L is added under the different HCl concentration of table 2
-1erosion rate after inhibiter
The corrosion inhibition of table 31-hexadecyl-3-Methylimidazole bromine ionic liquid in 12%HCl solution
Embodiment 8: potentiostatic polarization curve method evaluates imidazolium ionic liquid inhibiter corrosion inhibition
The corrosion inhibition of inhibiter is evaluated with reference to the potentiostatic polarization curve method in oil and gas industry standard SY/5273-1991.Be in the HCl solution of 12% at 300mL massfraction, adding concentration is respectively 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 and 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 significantly reduces the corrosion of 12%HCl to Q235 steel disc, simultaneously along with chain alkyl imidazolium ionic liquid carbochain lengthens, the corrosion potential of system is shuffled, anodic polarization rate increases, and the corrosion showing antianode has stronger restraining effect.The experiment conclusion that simultaneous verification weight loss method draws: if polar group is identical, when the carbon chain lengths of non-polar group (as alkyl) is different, along with the lengthening of chain alkyl imidazolium ionic liquid carbochain, ionic liquid suppresses corrosive power to strengthen gradually, and the suppression corrosive power of 1-octadecyl-3-Methylimidazole bromine is best.
Claims (4)
1. the application of imidazolium ionic liquid in oil field, described imidazolium ionic liquid is 1-tetradecyl-3-imidazole-butyl bromide salt or 1-hexadecyl-3-imidazole-butyl bromide salt; Described imidazolium ionic liquid as acidification corrosion inhibitor under DEG C hot conditions of temperature >=60 in oil well acidation process, for preventing acid solution to the corrosion of pipeline, hardware and down-hole string;
Described imidazolium ionic liquid is joined in oil well acidation system, pH<1, make the concentration of imidazolium ionic liquid be 150-250mg/L.
2. the application of imidazolium ionic liquid in oil field as claimed in claim 1, it is characterized in that, when described imidazolium ionic liquid mass concentration is 200mg/L, be the corrosion suppressing N80 steel disc in the HCl environment of 10-20% at massfraction.
3., as the application of imidazolium ionic liquid in oil field of claim 1 or 2, wherein, described imidazolium ionic liquid is prepared as follows:
The first step: join in autoclave by 2 ~ 4:1 mol ratio by imidazoles and bromo normal alkane I, described bromo normal alkane I chemical formula is C
nh
2n+1br, wherein n=4; Add ethyl acetate, wherein ethyl acetate add-on is 15 ~ 20 times of imidazoles and the total mol ratio of bromo normal alkane; Autoclave sealing is placed in thermostatic drying chamber, at 80 ~ 120 DEG C, react 15 ~ 16h, filter after reacted product is cooled to 0 DEG C, after filtered product re-crystallizing in ethyl acetate, wash 2 times with the mixed solvent of first benzene and heptane, remove unreacted imidazoles and bromo normal alkane; Product after purification dry 6h in the vacuum drying oven of 80 DEG C obtains N-alkyl imidazole intermediate C
n+3h
2n+4n
2, n=4;
Second step: join in autoclave by the N-alkyl imidazole intermediate of the first step reaction preparation and bromo normal alkane II by 1:1 ~ 1.2 mol ratio, described bromo normal alkane II chemical formula is C
nh
2n+1br, wherein n=14,16; Add ethyl acetate solvent, wherein ethyl acetate add-on is 15 ~ 20 times of N-alkyl imidazole intermediate and the total mol ratio of bromo normal alkane II; Autoclave sealing is placed in thermostatic drying chamber, at 130 DEG C, reacts 10 ~ 16h, obtain crude product, after crude product toluene wash purifying, obtain corresponding chain alkyl imidazolium ionic liquid.
4. the application of imidazolium ionic liquid in oil field as claimed in claim 3, is characterized in that in the preparation the first step of described imidazolium ionic liquid, first benzene and heptane volume ratio 1:4 in the mixed solvent of described first benzene and heptane.
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| CN104497994A (en) * | 2014-11-19 | 2015-04-08 | 中国地质大学（北京） | Drilling fluid and application of ionic liquid in drilling fluid |
| CN104532254B (en) * | 2014-12-17 | 2017-06-23 | 天津工业大学 | Compound ion liquid steel corrosion inhibiter and application |
| CN105038739B (en) * | 2015-07-15 | 2017-10-13 | 中国地质大学（北京） | The purposes of a kind of drilling fluid and glyoxaline ion liquid wherein |
| CN106047328B (en) * | 2016-07-11 | 2017-11-14 | 扬州大学 | A kind of nanoemulsions corrosion inhibiter containing imidazolium ionic liquid and preparation method thereof |
| EA202091413A1 (en) * | 2018-07-11 | 2020-09-24 | Бейкер Хьюз Холдингз Ллк | WELL ASPHALTEN INHIBITORS BASED ON IONIC LIQUID AND METHODS OF THEIR APPLICATION |
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| CN111607373B (en) * | 2020-05-06 | 2023-02-10 | 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 |
| CN113026024B (en) * | 2021-03-08 | 2023-06-20 | 吉林化工学院 | Mixed ionic liquid corrosion inhibitor and preparation method and application thereof |
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| CN116657143B (en) * | 2023-07-17 | 2023-12-12 | 四川冠山科技有限公司 | Green corrosion inhibitor and preparation method thereof |
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