CN106083727B - A kind of mixing-in fat base bis- (benzimidazole hyamines) and the preparation method and application thereof - Google Patents
A kind of mixing-in fat base bis- (benzimidazole hyamines) and the preparation method and application thereof Download PDFInfo
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- CN106083727B CN106083727B CN201610398838.XA CN201610398838A CN106083727B CN 106083727 B CN106083727 B CN 106083727B CN 201610398838 A CN201610398838 A CN 201610398838A CN 106083727 B CN106083727 B CN 106083727B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and 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
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/24—Cleaning or pickling metallic material with solutions or molten salts with neutral solutions
- C23G1/26—Cleaning or pickling metallic material with solutions or molten salts with neutral solutions using inhibitors
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Abstract
The invention belongs to fine organic chemical industry fields more particularly to a kind of mixing-in fat base bis- (benzimidazole hyamines) and the preparation method and application thereof.The present invention provides a kind of structures of mixing-in fat base bis- (benzimidazole hyamines), and the present invention also provides the preparation method and applications of above-mentioned mixing-in fat base bis- (benzimidazole hyamines).After introducing mixing-in fat base and quaternary ammonium group in benzimidazoline molecule, the hydrophobicity of protective film had both been increased, has reduced rate of metal corrosion, and has increased the water solubility of corrosion inhibiter.It can be obtained through measuring, corrosion inhibiter involved in technical solution provided by the invention, corrosion mitigating effect is substantially better than existing corrosion inhibiter.It solves in the prior art, there is corrosion mitigating effect difference and the technological deficiencies of poorly water-soluble for corrosion inhibiter.Moreover, raw material used in the present invention is gutter oil, while reducing production cost, also have the advantages that protect environment.
Description
Technical field
The invention belongs to fine organic chemical industry field more particularly to a kind of mixing-in fat base are bis- (benzimidazole hyamine)
And the preparation method and application thereof.
Background technique
In oil gas well mining and industrial heat power equipment acid cleaning process, acid solution is to oil pipe, casing and boiler in order to prevent
Etc. equipment corrosion, in acid solution add corrosion inhibiter be essential anti-corrosion measure, in recent years, imidazoline corrosion inhibitor is in oil
Using especially extensively in field pipeline anti-corrosion and pickling industry.
Currently, the synthesis of benzimidazoline is mainly with o-phenylenediamine or substituted o-phenylenediamine using organic carboxyl acid as raw material,
Using ladder-elevating temperature technology, it is prepared by amidation and cyclodehydration.The prior art specific the preparation method comprises the following steps: with C7~
Fatty acid, o-phenylenediamine or the substituted o-phenylenediamine of C20 is raw material, and azeotropic agent is added and catalyst carries out acylated, cyclization
A kind of fat-based benzimidazoline or fat-based substituted benzimidazole quinoline are synthesized, however, the inhibition that such preparation method obtains
Agent still remains the technological deficiency of corrosion mitigating effect difference.
Therefore, it develops and a kind of mixing-in fat base bis- (benzimidazole hyamines) and the preparation method and application thereof, uses
In the prior art in solution, it is urgently to be resolved to become those skilled in the art there is corrosion mitigating effect difference technological deficiency for corrosion inhibiter
The problem of.
Summary of the invention
In view of this, the present invention provides a kind of mixing-in fat base bis- (benzimidazole hyamines) and preparation method thereof with
Using for solving in the prior art, there is corrosion mitigating effect difference technological deficiencies for corrosion inhibiter.
It is bis- (benzimidazole hyamine) that the present invention provides a kind of mixing-in fat bases, bis- (benzimidazoline quaternary ammoniums
Salt) chemical structural formula are as follows:
Wherein, RnFor mixing-in fat base, R CH3Or C6H5, Z be-CH=CH- or
The present invention also provides a kind of preparation method of mixing-in fat base bis- (benzimidazole hyamines), feature exists
In, the preparation method is that: Step 1: gutter oil is hydrolyzed, fatty acid mixed is obtained, gained fatty acid mixed is the first product；
It is reacted Step 2: with N- substituted o-phenylenediamine amidation-cyclodehydration occurs for the first product, generates the second product；Step 3: institute
After stating the cooling of the second product, two bromo-hydrocarbons are added, quaternization reaction occurs, obtains product.
Preferably, the mass ratio of first product and N- substituted o-phenylenediamine is 1:(0.61~0.70).
Preferably, the amidation-cyclodehydration reaction carries out under nitrogen protection.
Preferably, the amidation-cyclodehydration reaction carries out in three stages: stage one, first product and N- take
Amidation process occurs for o-phenylenediamine, steams the water of amidation process generation immediately using dimethylbenzene as solvent, in reaction process；
After stage two, the stage one, heating steams the solvent；After stage three, the stage two, it is anti-that cyclisation occurs
It answers, vacuum distillation to no liquid generates, and obtains the second product.
Preferably, the time of the amidation process is 4~6h, and the temperature of the amidation process is 130~140 DEG C.
Preferably, 170~180 DEG C of the reaction temperature in the stage 2, the reaction time in the stage two are 4~5h.
Preferably, the time of the cyclization is 3h, and the temperature of the cyclization is 210~220 DEG C；Three institute of stage
The condition for the vacuum distillation stated is 20~25mmHg.
The temperature of the preferably described cooling is 60 DEG C.The mass ratio of first product and two bromo-hydrocarbons is 1:
(0.39~0.46), reaction time of the quaternization reaction are 1~1.5h, the reaction temperature of the quaternary ammonium words reaction is 60~
70℃。
The present invention also provides a kind of above-mentioned bis- (benzimidazole hyamines) of mixing-in fat base or above-mentioned preparation method to obtain
To application of the product in corrosion inhibiter.
In conclusion the present invention provides a kind of structure of mixing-in fat base bis- (benzimidazole hyamines), the present invention
Additionally provide the preparation method and application of above-mentioned mixing-in fat base bis- (benzimidazole hyamines).It is introduced in imidazoline molecule
After mixing-in fat base and quaternary ammonium group, the hydrophobicity of protective film had both been increased, rate of metal corrosion is reduced, and increased slow
Lose the water solubility of agent.It can be obtained through measuring, corrosion inhibiter involved in technical solution provided by the invention, corrosion mitigating effect is obvious
Better than existing corrosion inhibiter.It solves in the prior art, there is corrosion mitigating effect difference and the technological deficiencies of poorly water-soluble for corrosion inhibiter.
Moreover, raw material used in the present invention is gutter oil, while reducing production cost, also have the advantages that protect environment.
Specific embodiment
The present invention provides a kind of mixing-in fat bases bis- (benzimidazole hyamines) and the preparation method and application thereof, are used for
It solves in the prior art, there is corrosion mitigating effect difference technological deficiencies for corrosion inhibiter.
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
Technical staff's every other embodiment obtained without making creative work belongs to the model that the present invention protects
It encloses.
In order to which the present invention is described in more detail, below with reference to embodiment to provided by the invention, it is specifically described.
Embodiment 1
The present embodiment is preparation 1,4- bis- (2- mixing-in fat base -1- benzimidazoline phenyl quaternary ammonium group) -2- butylene inhibition
The specific embodiment of agent.
The chemical equation of the reaction principle of the present embodiment are as follows:
Gutter oil is hydrolyzed into obtain fatty acid mixed, it is spare.
In the three-necked flask equipped with water segregator, thermometer, condenser pipe and agitating device, addition 27.2g fatty acid mixed,
16.6gN- phenyl o-phenylenediamine and 60ml dimethylbenzene are passed through nitrogen protection, are constantly isolated from system with water segregator in reaction
By-product water is slowly heated to 140 DEG C, reacts 3.5~4.0h.When the close theoretical water yield of collection water, then it is warming up to 170
~180 DEG C steam solvent, are heated to reflux 4~5 hours.Continue after 210~220 DEG C of cyclization 3h, subtracts in 20~25mmHg
Pressure distillation, until not having liquid outflow.
Reaction system is cooled to 60 DEG C, 9.7g1, the bromo- 2- butylene of 4- bis- are added into mixture, mixture is warming up to 60
~70 DEG C, after being stirred to react 1.5h, vacuum distillation obtains water-soluble-two (2- mixing-in fat base -1- benzimidazoline quaternary ammonium of Isosorbide-5-Nitrae
Base) -2- butylene corrosion inhibiter, as product 1.Receive product 1 amounts to 36.6g.
Embodiment 2
The present embodiment is preparation 1,4- bis- (2- mixing-in fat base -1- benzimidazoline methylmethylene quaternary ammonium group) benzene inhibition
The specific embodiment of agent.
The chemical equation of the reaction principle of the present embodiment are as follows:
Gutter oil is hydrolyzed into obtain fatty acid mixed, it is spare.
In the three-necked flask equipped with water segregator, thermometer, condenser pipe and agitating device, addition 27.2g fatty acid mixed,
17.5gN- methyl-o-phenylenediamine and 80ml dimethylbenzene are passed through nitrogen protection, are constantly isolated from system with water segregator in reaction
By-product water is slowly heated to 140 DEG C, reacts 3.5~4.0h.When the close theoretical water yield of collection water, then it is warming up to 170
~180 DEG C steam solvent, are heated to reflux 4~5 hours.Continue after 210~220 DEG C of cyclization 3h, subtracts in 20~25mmHg
Pressure distillation, until not having liquid outflow.
Reaction system is cooled to 60 DEG C, 11.9g1,4- bis- (bromomethyl) benzene are added into mixture, mixture is warming up to
60~70 DEG C, after being stirred to react 1h, vacuum distillation obtains water-soluble-two (2- mixing-in fat base -1- benzimidazoline methyl of Isosorbide-5-Nitrae
Quaternary ammonium methylene) benzene corrosion inhibiter, as product 2.Receive product 2 amounts to 36.6g.
Embodiment 3
The present embodiment is that preparation (2- mixing-in fat base -1- benzimidazoline ylmethyl the quaternary ammonium group) -2- butylene of 1,4- bis- is slow
Lose the specific embodiment of agent.
The chemical equation of the reaction principle of the present embodiment are as follows:
Gutter oil is hydrolyzed into obtain fatty acid mixed, it is spare.
In the three-necked flask equipped with water segregator, thermometer, condenser pipe and agitating device, addition 27.2g fatty acid mixed,
18.5gN- methyl-o-phenylenediamine and 40ml dimethylbenzene are passed through nitrogen protection, are constantly isolated from system with water segregator in reaction
By-product water is slowly heated to 140 DEG C, reacts 3.5~4.0h.When the close theoretical water yield of collection water, then it is warming up to 170
~180 DEG C steam solvent, are heated to reflux 4~5 hours.Continue after 210~220 DEG C of cyclization 3h, subtracts in 20~25mmHg
Pressure distillation, until not having liquid outflow.
Reaction system is cooled to 60 DEG C, 9.7g1, the bromo- 2- butylene of 4- bis- are added into mixture, mixture is warming up to 60
~70 DEG C, after being stirred to react 1h, vacuum distillation obtains water-soluble-two (2 '-mixing-in fat bases -1 '-benzimidazoline methyl of Isosorbide-5-Nitrae
Quaternary ammonium group) -2- butylene corrosion inhibiter, as product 3.Receive product 3 amounts to 36.3g.
Embodiment 4
The present embodiment is preparation 1,4- bis- (2- mixing-in fat base -1- benzimidazoline phenylmethylene quaternary ammonium group) benzene inhibition
The specific embodiment of agent.
The chemical equation of the reaction principle of the present embodiment are as follows:
By the test method for implementing 2, N- methyl-o-phenylenediamine is substituted with N- phenyl o-phenylenediamine, obtains water-soluble Isosorbide-5-Nitrae-
Two (2- mixing-in fat base -1- benzimidazoline phenyl quaternary ammonium methylene) benzene corrosion inhibiter, as product 4.Receive product 4 is total
32.2g。
Embodiment 5
The present embodiment is the specific experiment for measuring the corrosion mitigating effect of product 1~4.
The present embodiment illustrates the corrosion mitigating effect of product 1~6 by measurement simulation oil field pipeline corrosion protection inhibition experiment.Due to
Oil field pipe is mainly Q235 steel, thus the present embodiment using Q235 metal material come simulated experiment, examine the performance of corrosion inhibiter.
In the present embodiment, used reference substance is water-soluble oleic imidazolinone.
Product 1 is added into the 5%HCl solution of 1000ml, in the solution by the suspension of Q235 steel disc, 60 DEG C of water bath with thermostatic control,
After placing 6h, using the etching extent of weight-loss method measurement steel disc.In the present embodiment, the mass percentage concentration of product 1 is 0.25%.
The corrosion mitigating effect measurement experiment of 2~product of product 4 and reference substance is same as above, and details are not described herein.After measuring
It calculates resulting corrosion inhibition rate result and please refers to table 1.
Table 1: corrosion inhibition rate experimental result
| Product | Product 1 | Product 2 | Product 3 | Product 4 | Reference substance |
| Corrosion inhibition rate | 98.2 | 96.5 | 95.9 | 98.4 | 92.5 |
It can be obtained from table 1, the corrosion inhibition rate of product 1~4 will be apparently higher than control, illustrate, technical solution provided by the invention
Corresponding product has the advantages that corrosion mitigating effect is good.
In conclusion the present invention provides a kind of structure of mixing-in fat base bis- (benzimidazole hyamines), the present invention
Additionally provide the preparation method and application of above-mentioned mixing-in fat base bis- (benzimidazole hyamines).It is introduced in imidazoline molecule
After mixing-in fat base and quaternary ammonium group, the hydrophobicity of protective film had both been increased, rate of metal corrosion is reduced, and increased slow
Lose the water solubility of agent.It can be obtained through measuring, corrosion inhibiter involved in technical solution provided by the invention, corrosion mitigating effect is obvious
Better than existing corrosion inhibiter.It solves in the prior art, there is corrosion mitigating effect difference and the technological deficiencies of poorly water-soluble for corrosion inhibiter.
Moreover, raw material used in the present invention is gutter oil, while reducing production cost, also have the advantages that protect environment.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (9)
1. a kind of preparation method of mixing-in fat base bis- (benzimidazole hyamines), which is characterized in that
The chemical structural formula of bis- (imidazoline quaternary ammonium salts) are as follows:
Wherein, RnFor mixing-in fat base, R CH3Or C6H5, Z be-CH=CH- or
The preparation method is that:
Step 1: gutter oil is hydrolyzed, fatty acid mixed is obtained, gained fatty acid mixed is the first product；
It is reacted Step 2: with N- substituted o-phenylenediamine amidation-cyclodehydration occurs for the first product, generates the second product, it is described
N- substituted o-phenylenediamine is selected from N- phenyl o-phenylenediamine or N- methyl-o-phenylenediamine；
Step 3: two bromo-hydrocarbons are added after second product is cooling, quaternization reaction occurs, obtains product；Two bromo-hydrocarbons
Selected from (bromomethyl) benzene of 1,4- bis- or the bromo- 2- butylene of 1,4- bis-.
2. preparation method according to claim 1, which is characterized in that the matter of first product and N- substituted o-phenylenediamine
Amount is than being 1:(0.61~0.70).
3. preparation method according to claim 2, which is characterized in that the amidation-cyclodehydration reaction is protected in nitrogen
Shield is lower to be carried out.
4. preparation method according to claim 2, which is characterized in that the amidation-cyclodehydration reaction is in three stages
It carries out:
Amidation process, using dimethylbenzene as solvent, reaction process occur for stage one, first product and N- substituted o-phenylenediamine
In steam immediately amidation process generation water；
After stage two, the stage one, heating steams the solvent；
After stage three, the stage two, cyclization occurs, vacuum distillation to no liquid generates, and obtains the second product.
5. the preparation method according to claim 4, which is characterized in that the time of the amidation process is 4~6h, described
The temperature of amidation process is 130~140 DEG C.
6. the preparation method according to claim 4, which is characterized in that 170~180 DEG C of the reaction temperature in the stage 2,
The reaction time in the stage two is 4~5h.
7. the preparation method according to claim 4, which is characterized in that the time of the cyclization is 3h, the cyclisation
The temperature of reaction is 210~220 DEG C；The condition of vacuum distillation described in stage three is 20~25mmHg.
8. the preparation method according to claim 4, which is characterized in that the temperature of the cooling is 60 DEG C.Described first produces
The mass ratio of object and two bromo-hydrocarbons is 1:(0.39~0.46), the reaction time of the quaternization reaction is 1~1.5h, institute
The reaction temperature for stating quaternization reaction is 60~70 DEG C.
9. a kind of application of product obtained including preparation method described in claim 1 to 8 any one in corrosion inhibiter.
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| CN112876483A (en) * | 2021-01-18 | 2021-06-01 | 邓颖菁 | Dicationic benzimidazole corrosion inhibitor and preparation method thereof |
| CN114106788B (en) * | 2021-12-15 | 2024-07-26 | 湖南省希润弗高分子新材料有限公司 | Industrial circulating cooling liquid |
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|---|---|---|---|---|
| WO2004092447A2 (en) * | 2003-04-11 | 2004-10-28 | Nalco Energy Services | Imidazoline corrosion inhibitors |
| CN101565608A (en) * | 2009-05-25 | 2009-10-28 | 新疆大学 | Preparation method of novel acidified corrosion inhibitor and use thereof |
| CN101613622A (en) * | 2009-07-29 | 2009-12-30 | 中国石油化工集团公司 | A kind of composite inhibiter and its production and use |
| CN103289671A (en) * | 2013-05-28 | 2013-09-11 | 四川安东油气工程技术服务有限公司 | Corrosion inhibitor and preparation method thereof |
| CN105088252A (en) * | 2015-08-19 | 2015-11-25 | 广东工业大学 | Benzimidazoline corrosion inhibitor prepared from refined swill-cooked dirty oil |
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- 2016-06-06 CN CN201610398838.XA patent/CN106083727B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004092447A2 (en) * | 2003-04-11 | 2004-10-28 | Nalco Energy Services | Imidazoline corrosion inhibitors |
| CN101565608A (en) * | 2009-05-25 | 2009-10-28 | 新疆大学 | Preparation method of novel acidified corrosion inhibitor and use thereof |
| CN101613622A (en) * | 2009-07-29 | 2009-12-30 | 中国石油化工集团公司 | A kind of composite inhibiter and its production and use |
| CN103289671A (en) * | 2013-05-28 | 2013-09-11 | 四川安东油气工程技术服务有限公司 | Corrosion inhibitor and preparation method thereof |
| CN105088252A (en) * | 2015-08-19 | 2015-11-25 | 广东工业大学 | Benzimidazoline corrosion inhibitor prepared from refined swill-cooked dirty oil |
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