CN106554313B - A kind of acylthioureas imidazoline inhibitor and preparation method thereof - Google Patents
A kind of acylthioureas imidazoline inhibitor and preparation method thereof Download PDFInfo
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- CN106554313B CN106554313B CN201610960907.1A CN201610960907A CN106554313B CN 106554313 B CN106554313 B CN 106554313B CN 201610960907 A CN201610960907 A CN 201610960907A CN 106554313 B CN106554313 B CN 106554313B
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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
- C07D233/04—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
- 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
- C07D233/16—Radicals substituted by nitrogen atoms
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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
- C07D233/04—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
- 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
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- C—CHEMISTRY; METALLURGY
- 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
- 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
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
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Abstract
The invention discloses a kind of acylthioureas imidazoline corrosion inhibitors and preparation method thereof.The structural formula of acylthioureas imidazoline of the present invention is as follows:
Description
Technical field
The present invention relates to oil field chemical technical fields, specially acylthioureas imidazoline inhibitor structure feature and preparation
Method, and in particular to acylthioureas imidazoline inhibitor synthetic method.
Background technique
Addition corrosion inhibiter be solve oil gas field etching problem common method, because its with it is at low cost, easy to operate, take effect
Fastly, integral device can be protected, be suitble to the features such as digital preservation, and obtained during oil and gas exploitation sum aggregate is defeated extensive
Using.Currently, the most widely used in oil gas field is imidazoline corrosion inhibitor, can effectively solve the problem that common in the production of oil field
CO2/H2S is to corrosion of metal problem, studies have shown that its inhibition efficiency can be improved in imidazoline inhibitor compounding thiocarbamide, the two can
Synergistic effect, but imidazoline inhibitor and thiocarbamide collaboration proportion are easy to be influenced by the changeable factor in scene, therefore collaboration is caused to be made
It fails under certain condition, causes the generation of spot corrosion.
Summary of the invention
The present invention enhances the synergistic effect of imidazoline and thiocarbamide, not by outer to overcome the shortcomings of the prior art
Under conditions of the influence of boundary's factor, thiourea group is introduced into imidazoline molecule, forms acylthioureas imidazoline inhibitor, structure
In simultaneously contain O, S, N, enhance the absorption with iron, promote the corrosion inhibition of corrosion inhibiter, therefore develop acylthioureas imidazoline
Corrosion inhibiter.
Acylthioureas imidazoline corrosion inhibitor of the invention, the structural formula of the acylthioureas imidazoline are as follows:
Wherein: R1, R2 are identical or different, and are respectively, separately or cooperatively the linear chain or branched chain with 1~20 C atom
Alkyl, aryl, naphthenic base；N is the integer between 1~8.
In acylthioureas imidazoline inhibitor of the present invention, wherein the R1Preferably-Ph, naphthenic base ,-C11H23,-
C8H17,-C15H31, 17 carbon -9- alkenyls, along 21 carbon -13- alkenyls；R2Preferably acrylic ,-Ph, ethyl；N=1,2.
The present invention also provides a kind of preparation methods of above-mentioned acylthioureas imidazoline inhibitor, include the following steps:
(1) it using organic acid and organic amine as reaction raw materials, is dehydrated through two steps, synthesizes imidazoline intermediate, reaction equation is as follows:
Wherein R1Linear chain or branched chain alkyl, aryl, naphthenic base with 1~20 C atom, n are 1~8；
(2) organic acyl halide, rhodanate and imidazoline intermediate are successively reacted, generates acylthioureas imidazoline, reaction
Formula is as follows:
Wherein R1,R2Linear chain or branched chain alkyl, aryl, naphthenic base for 1~20 C atom, R1,R2It is identical or different, M
For K, Na, NH4；X is Cl, Br, the integer that n is 1~8；
Specific steps are as follows:
(1) synthesis of imidazoline
Under nitrogen protection, to thermometer, blender, condenser pipe and water segregator four-hole bottle in successively precise
Organic acid and organic amine, molar ratio 1:0.8-1.5, while dry benzene kind solvent being added into reactor, reactant with
The mass ratio of benzene kind solvent is 1:0.5-1；Heating reflux 1h~4h at 120-140 DEG C isolates amidation process generation
Water；It is gradually heated to 140 DEG C~210 DEG C heat preservation 1h~2h again, solvent and the complete raw material of unreacted is evaporated off；Then it is gradually heated to
210 DEG C~250 DEG C heat preservation 2h~4h steam the water of cyclization generation；It is finally that reactant is cooling, obtain imidazoline；
(2) synthesis of acylthioureas imidazoline inhibitor
To with thermometer, blender, condenser pipe four-hole bottle in sequentially add acyl chlorides and dichloromethane solvent, acyl chlorides with
The mass ratio of dichloromethane solvent is 1:0.5-1, opens mechanical stirring and rhodanate is added portionwise at 0 DEG C~10 DEG C
In reactor, rhodanate and acyl chlorides molar ratio are that 0.9-1.2:1 is stirred to react 0.5~2h, finally 10 at this temperature
DEG C~40 DEG C at be added the imidazoline of step 1 preparation, imidazoline and acyl chlorides molar ratio be 0.9-1.2:1 at this temperature, stirring
0.5~2h is reacted, acylthioureas imidazoline inhibitor is made in evaporating solvent under reduced pressure.
The advantages of acylthioureas imidazoline inhibitor of the present invention, is for thiourea group to be introduced into imidazoline molecular structure, shape
At acylthioureas imidazoline inhibitor, the synergistic effect of intramolecular is formed, contains O, S, N simultaneously in structure, corrosion inhibiter can be promoted
Corrosion inhibition.
Specific embodiment
The present invention is further described again below by embodiment
Embodiment 1
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Oleic acid and diethylenetriamine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added molten
In the 2.5h that flows back at 120 DEG C after agent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature 1h,
Solvent and the complete amine of unreacted is evaporated off；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally will
Reactant is cooling, obtains imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
Acryloyl chloride and dichloromethane solvent, acyl are sequentially added into the four-hole bottle for having thermometer, blender, condenser pipe
The mass ratio of chlorine and dichloromethane solvent is 1:1, opens mechanical stirring and reactor is added portionwise in sodium sulfocyanate at 0 DEG C
In, sodium sulfocyanate and acryloyl chloride molar ratio are that 1:1 is stirred to react 2h at this temperature, and step finally is added at 10 DEG C
(1) preparation has imidazoline, imidazoline and acryloyl chloride molar ratio at this temperature, to be stirred to react 2h for 1:1, remove under reduced pressure molten
Acylthioureas imidazoline inhibitor is made in agent.
Embodiment 2
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Oleic acid and triethylene tetramine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added molten
In the 2.5h that flows back at 120 DEG C after agent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature 1h,
Solvent and the complete amine of unreacted is evaporated off；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally will
Reactant is cooling, obtains imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
Acryloyl chloride and dichloromethane solvent, acyl are sequentially added into the four-hole bottle for having thermometer, blender, condenser pipe
The mass ratio of chlorine and dichloromethane solvent is 1:1, opens mechanical stirring and reactor is added portionwise in potassium rhodanide at 0 DEG C
In, potassium rhodanide and acryloyl chloride molar ratio are that 1:1 is stirred to react 2h at this temperature, and step finally is added at 10 DEG C
(1) preparation has imidazoline, imidazoline and acryloyl chloride molar ratio at this temperature, to be stirred to react 2h for 1:1, remove under reduced pressure molten
Acylthioureas imidazoline inhibitor is made in agent.
Embodiment 3
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Benzoic acid and diethylenetriamine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added
In the 2.5h that flows back at 120 DEG C after solvent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature
Solvent and the complete amine of unreacted is evaporated off in 1h；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally
Reactant is cooling, obtain imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
To with thermometer, blender, condenser pipe four-hole bottle in sequentially add acryloyl chloride and dichloromethane solvent, third
The mass ratio of alkene acyl chlorides and dichloromethane solvent is 1:1, opens mechanical stirring and ammonium thiocyanate is added portionwise anti-at 0 DEG C
It answers in device, ammonium thiocyanate and acryloyl chloride molar ratio are that 1:1 is stirred to react 2h at this temperature, and step is finally added at 10 DEG C
Suddenly (1) preparation has imidazoline, imidazoline and acryloyl chloride molar ratio at this temperature, to be stirred to react 2h for 1:1, remove under reduced pressure
Acylthioureas imidazoline inhibitor is made in solvent.
Embodiment 4
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Erucic acid and diethylenetriamine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added molten
In the 2.5h that flows back at 120 DEG C after agent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature 1h,
Solvent and the complete amine of unreacted is evaporated off；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally will
Reactant is cold, obtains imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
To with thermometer, blender, condenser pipe four-hole bottle in sequentially add acryloyl chloride and dichloromethane solvent, third
The mass ratio of alkene acyl chlorides and dichloromethane solvent is 1:1, opens mechanical stirring and potassium rhodanide is added portionwise anti-at 0 DEG C
It answers in device, potassium rhodanide and acryloyl chloride molar ratio are that 1:1 is stirred to react 2h at this temperature, and step is finally added at 10 DEG C
Suddenly (1) preparation has imidazoline, and imidazoline and acryloyl chloride molar ratio are 1:1, at this temperature, is stirred to react 2h, decompression is steamed
Except acylthioureas imidazoline inhibitor is made in solvent.
Embodiment 5
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Oleic acid and diethylenetriamine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added molten
In the 2.5h that flows back at 120 DEG C after agent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature 1h,
Solvent and the complete amine of unreacted is evaporated off；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally will
Reactant is cooling, obtains imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
Chlorobenzoyl chloride and dichloromethane solvent, benzene are sequentially added into the four-hole bottle for having thermometer, blender, condenser pipe
The mass ratio of formyl chloride and dichloromethane solvent is 1:1, opens mechanical stirring and sodium sulfocyanate is added portionwise anti-at 0 DEG C
It answers in device, sodium sulfocyanate and chlorobenzoyl chloride molar ratio are that 1:1 is stirred to react 2h at this temperature, and step is finally added at 10 DEG C
Suddenly (1) preparation has imidazoline, and imidazoline and chlorobenzoyl chloride molar ratio are 1:1, at this temperature, is stirred to react 2h, decompression is steamed
Except acylthioureas imidazoline inhibitor is made in solvent.
Embodiment 6
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Oleic acid and diethylenetriamine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added molten
In the 2.5h that flows back at 120 DEG C after agent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature 1h,
Solvent and the complete amine of unreacted is evaporated off；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally will
Reactant is cooling, obtains imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
Chlorobenzoyl chloride and dichloromethane solvent, benzene are sequentially added into the four-hole bottle for having thermometer, blender, condenser pipe
The mass ratio of formyl chloride and dichloromethane solvent is 1:0.5, opens mechanical stirring and sodium sulfocyanate is added portionwise at 0 DEG C
In reactor, sodium sulfocyanate and chlorobenzoyl chloride molar ratio are that 0.9:1 is stirred to react 2h at this temperature, are finally added at 10 DEG C
Entering the imidazoline that has of step (1) preparation, imidazoline and chlorobenzoyl chloride molar ratio are that 0.9:1 is stirred to react 2h at this temperature,
Acylthioureas imidazoline inhibitor is made in evaporating solvent under reduced pressure.
Embodiment 7
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Oleic acid and diethylenetriamine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added molten
In the 2.5h that flows back at 120 DEG C after agent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature 1h,
Solvent and the complete amine of unreacted is evaporated off；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally will
Reactant is cooling, obtains imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
Chlorobenzoyl chloride and dichloromethane solvent, benzene are sequentially added into the four-hole bottle for having thermometer, blender, condenser pipe
The mass ratio of formyl chloride and dichloromethane solvent is 1:0.5, opens mechanical stirring and sodium sulfocyanate is added portionwise at 0 DEG C
In reactor, sodium sulfocyanate and chlorobenzoyl chloride molar ratio are that 1.2:1 is stirred to react 2h at this temperature, are finally added at 10 DEG C
Entering the imidazoline that has of step (1) preparation, imidazoline and chlorobenzoyl chloride molar ratio are that 1.2:1 is stirred to react 2h at this temperature,
Acylthioureas imidazoline inhibitor is made in evaporating solvent under reduced pressure.
Embodiment 8
(1) synthesis of imidazoline
Under nitrogen protection, successively accurate into the reactor with thermometer, blender, condenser pipe and water segregator to be added
Oleic acid and diethylenetriamine, molar ratio 1:1.1, and dry dimethylbenzene 50g is added into reactor and makees solvent, it is added molten
In the 2.5h that flows back at 120 DEG C after agent, the water of amidation process generation is isolated；It is gradually heated to 210 DEG C again, and keeps the temperature 1h,
Solvent and the complete amine of unreacted is evaporated off；240 DEG C of insulation reaction 3h are then heated to, the water of cyclization generation is steamed；Finally will
Reactant is cooling, obtains imidazoline.
(2) synthesis of acylthioureas imidazoline inhibitor
To with thermometer, blender, condenser pipe four-hole bottle in sequentially add acryloyl chloride and dichloromethane solvent, third
The mass ratio of alkene acyl chlorides and dichloromethane solvent is 1:1, opens mechanical stirring and potassium rhodanide is added portionwise at 10 DEG C
In reactor, potassium rhodanide and acryloyl chloride molar ratio are that 0.9:1 is stirred to react 0.5h at this temperature, finally at 40 DEG C
The imidazoline that has of step (1) preparation is added, imidazoline and acryloyl chloride molar ratio are that 0.9:1 is stirred to react at this temperature
Acylthioureas imidazoline inhibitor is made in 0.5h, evaporating solvent under reduced pressure.
Effect experiment
The experiment condition of use:
Test piece material: A3Carbon steel area: 12.6cm2
Temperature: 95 DEG C of CO2Partial pressure: 0.8Mpa
Stagnation pressure: 2.0Mpa revolving speed: 450 turns
The experimental results are shown inthe following table:
Acylthioureas imidazoline inhibitor henchnmrk test result table
From the point of view of experiment effect, under the above conditions, the corrosion inhibition for the acylthioureas imidazoline inhibitor researched and developed is excellent
More, synergistic effect is preferable.
Claims (3)
1. a kind of acylthioureas imidazoline corrosion inhibitor, which is characterized in that the structural formula of the acylthioureas imidazoline is as follows:
Wherein: the R1For-C15H31, 17 carbon -9- alkenyls, along 21 carbon -13- alkenyls；R2For with 1~20 C atom
Linear chain or branched chain alkyl, or-Ph, 2- pyridyl group；N is 1 or 2.
2. acylthioureas imidazoline inhibitor according to claim 1, which is characterized in that the R2For acrylic ,-Ph, second
Base, 2- pyridyl group；N=1,2.
3. the preparation method of acylthioureas imidazoline inhibitor described in a kind of claim 1, which is characterized in that including walking as follows
It is rapid:
(1) synthesis of imidazoline
Under nitrogen protection, into the four-hole bottle with thermometer, blender, condenser pipe and water segregator, successively precise is organic
Acid and organic amine, molar ratio 1:0.8-1.5, while dry benzene kind solvent being added into reactor, reactant and benzene class
The mass ratio of solvent is 1:0.5-1；Heating reflux 1h~4h at 120 DEG C -140 DEG C, isolates the water of amidation process generation；
It is gradually heated to 140 DEG C~210 DEG C heat preservation 1h~2h again, solvent and the complete raw material of unreacted is evaporated off；Then 210 are gradually heated to
DEG C~250 DEG C of heat preservation 2h~4h, steam the water of cyclization generation；It is finally that reactant is cooling, obtain imidazoline；
Reaction equation is as follows:
The wherein R1For-C15H31, 17 carbon -9- alkenyls, along 21 carbon -13- alkenyls；N is 1 or 2；
(2) synthesis of acylthioureas imidazoline inhibitor
Acyl chlorides and dichloromethane solvent, acyl chlorides and dichloro are sequentially added into the four-hole bottle for having thermometer, blender, condenser pipe
The mass ratio of methane solvent is 1:0.5-1, opens mechanical stirring and reaction is added portionwise in rhodanate at 0 DEG C~10 DEG C
In device, rhodanate and acyl chlorides molar ratio are that 0.9-1.2:1 is stirred to react 0.5~2h at this temperature, finally 10 DEG C~
The imidazoline of step 1 preparation is added at 40 DEG C, imidazoline and acyl chlorides molar ratio are 0.9-1.2:1, and at this temperature, stirring is anti-
0.5~2h is answered, acylthioureas imidazoline inhibitor is made in evaporating solvent under reduced pressure；
Reaction equation is as follows:
The wherein R1For-C15H31, 17 carbon -9- alkenyls, along 21 carbon -13- alkenyls；R2For with 1~20 C atom
Linear chain or branched chain alkyl, or-Ph, 2- pyridyl group；N is 1 or 2；M is K, Na, NH4, X Cl, Br.
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| CN108129463B (en) * | 2018-01-24 | 2021-03-16 | 广东工业大学 | Dioxolane imidazoline compound, preparation method thereof and corrosion inhibitor |
| CN110105943B (en) * | 2019-06-04 | 2021-07-09 | 中海油常州涂料化工研究院有限公司 | High-temperature acidizing corrosion inhibitor and preparation method thereof |
| CN110344063A (en) * | 2019-08-27 | 2019-10-18 | 山东益丰生化环保股份有限公司 | A kind of modified imidazoline corrosion inhibiter and preparation method thereof |
| CN111718298A (en) * | 2020-04-26 | 2020-09-29 | 西南石油大学 | Imidazoline derivative, synthesis method and application thereof |
| CN111719158B (en) * | 2020-05-27 | 2022-08-23 | 东营东方化学工业有限公司 | Corrosion inhibitor composition suitable for wide flow rate range and preparation method thereof |
| CN112940700B (en) * | 2021-01-19 | 2023-02-10 | 中国石油天然气股份有限公司 | Nitrogen-containing corrosion inhibition main agent, gas-liquid two-phase corrosion inhibitor, and preparation method and application thereof |
| CN114456148A (en) * | 2022-01-11 | 2022-05-10 | 中海油天津化工研究设计院有限公司 | Oil field corrosion inhibitor with good compatibility and preparation method thereof |
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