CN104232073A - Preparation method of [1,5] benzodiazepine compound and application of [1,5] benzodiazepine compound - Google Patents
Preparation method of [1,5] benzodiazepine compound and application of [1,5] benzodiazepine compound Download PDFInfo
- Publication number
- CN104232073A CN104232073A CN201410459458.3A CN201410459458A CN104232073A CN 104232073 A CN104232073 A CN 104232073A CN 201410459458 A CN201410459458 A CN 201410459458A CN 104232073 A CN104232073 A CN 104232073A
- Authority
- CN
- China
- Prior art keywords
- benzodiazepine
- thienyl
- methylphenyl
- hydrochloric acid
- inhibiter
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/32—Anticorrosion additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a hydrochloric acid pickling inhibitor of carbon steel, and particularly relates to a preparation method of a [1,5] benzodiazepine compound and an application of the [1,5] benzodiazepine compound. The [1,5] benzodiazepine compound is 2-(2-thienyl)-4-p-methylphenyl [1,5] benzodiazepine, wherein the structural formula is as shown in the formula 1 in the specification. The product disclosed by the invention is capable of effectively preventing general corrosion and local corrosion of the carbon steel in the contact process with a hydrochloric acid solution. The compound at present is a brand-new compound, and has not been utilized as a metal inhibitor. By adopting the pickling inhibitor disclosed by the invention, the [1,5] benzodiazepine compound is little in dosage, small in toxicity, high in efficiency, good in stability, strong in sustained action ability, is capable of effectively inhibiting corrosion damage of the carbon steel, and has a wide application prospect.
Description
Technical field
The present invention relates to the hydrochloric acid pickling corrosion inhibitor of carbon steel, a kind of preparation method of [1,5] Benzodiazepine compounds and application thereof, belong to metal corrosion and protection technical field specifically.
Background technology
At present, acidifying is the important measures improving Oil/gas Well recovery ratio, and domestic most Oil/gas Well all needs to rely on Acidizing Technology process stratum, to improve the recovery ratio of Oil/gas Well, realizes volume increase and the stable yields of Oil/gas Well.But the process on acid solution note people stratum can produce serious corrosion to Oil/gas Well equipment and pipeline, greatly shorten the work-ing life of Oil/gas Well equipment and pipeline, formation can be damaged again by the metallic iron ion of acid-soluble erosion simultaneously, had a strong impact on the normal production of Oil/gas Well.And to add inhibiter be the effective way preventing Oil/gas Well equipment and pipeline corrosion.
Acidification corrosion inhibitor is a kind ofly present in acidic medium with suitable concentration and form, prevents and slow down the chemical substance of steel corrosion or the mixture of several chemical substance.Organic acidification corrosion inhibitor that Domestic Oil And Gas Fields is conventional mainly contains benzoglyoxaline, tetrahydroglyoxaline, quaternary ammonium salt, pyrimidine, thiadiazoles derivative etc.Metal inhibitor common in oil-gas field often also exists that toxicity is large, cost is high, poor stability, effect are undesirable and product and the problem such as separated from solvent is difficult in synthesis and application process thereof.At present, the research of inhibiter is just towards the future development of " environmentally friendly inhibiter ".The present invention proposes the synthetic method that a kind of novel environmental friendly is applied to the hcl acidifying inhibiter of carbon steel efficiently, the molecular structure of this inhibiter has larger conjugated system relative to traditional inhibiter, the internal layer d unoccupied orbital of its lone-pair electron contained and π-electron and metal Fe atom forms the chemical bond adsorbed more, more closely stable adsorption film is formed at steel surface, play the contact hindering corrosive medium and metallic surface, thus slow down the effect of corrosion of carbon steel.
Summary of the invention
The object of the invention is to the deficiency solving prior art existence, provide a kind of low toxicity, environmental friendliness by the compound molecule that project organization is new, the application of tall and erect compounds as efficient acidification corrosion inhibitor mixed by the efficient benzo containing aromatic heterocycle.
The present invention adopts technical scheme to be for achieving the above object:
A kind of benzo containing aromatic heterocycle is mixed the application of tall and erect compounds as Efficient Acid ring inhibiter, the described benzo containing aromatic heterocycle tall and erect compounds of mixing is 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine, its structural formula is such as formula shown in one:
Further, during using formula one compound as hydrochloric acid pickling corrosion inhibitor, by 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine is dissolved in the hydrochloric acid soln of 1.0 ~ 5.0mol/L respectively, then at room temperature to mixing solutions ultrasonic disperse 30min, make it to dissolve completely, stirring at room temperature evenly.
Further say, steel article is immersed in and adds in the 1.0mol/L hydrochloric acid soln of inhibiter, soak time is no less than 1h, submergence temperature is 25 ~ 55 DEG C, wherein in often liter of hydrochloric acid soln, 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine add-on is 10 ~ 100mg.
The preparation method of described formula one compound is as follows:
First 2 thiophene carboxaldehyde and p-methyl aceto phenone are reacted in the ethanolic soln of potassium hydroxide, stirring reaction 12h under normal temperature, decompress filter obtains lurid 1-p-methylphenyl-3-(2-thienyl) acrylketone, 1-p-methylphenyl-3-(2-thienyl) acrylketone obtained and O-Phenylene Diamine are reacted in acetic acid and dimethyl formamide mixing solutions, oil bath reflux, magnetic agitation 12h, refrigerator freezing spends the night 12h, decompress filter obtains brown crude product, then through washing, Recrystallisation from acetic acid obtains light yellow crystal.Be product 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine, hydrogen nuclear magnetic resonance characterization result is as follows:
1HNMR(dimethyl?sulfoxide(DMSO),400MHz):δ＝7.72-7.74(m,4H,Ar-H),7.54-7.62(m,4H,Ar-H),7.48(s,1H,NH),7.28-7.36(m,3H,Thiophene),4.5(s,1H,HC＝C-Ar),1.92(s,3H,CH
3-Ar)
The advantage that the present invention has:
1. cost is low.Inhibiter effective constituent of the present invention is 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine, and synthesis material abundance is simple and easy to get, cheap.
2. low toxic and environment-friendly.Inhibiter of the present invention is compared with traditional organic carbon steel corrosion inhibitor with acidification corrosion inhibitor conventional at present, can be nontoxic or low toxicity material at natural degradation under solar irradiation, can not bring negative impact, meet the development trend of environmentally friendly inhibiter to environment.
3. high efficiency.As long as inhibiter of the present invention in use adds can play on a small quantity effectively suppress the corrosion of carbon steel in acidic medium.
4. persistence is good.Inhibiter of the present invention has certain persistence, can keep higher corrosion inhibition for a long time.
5. suitability is good.Inhibiter of the present invention has advantage applied widely, under differing temps, acidity, all have excellent corrosion inhibition, and inhibition efficiency can reach 89%-98%.
Accompanying drawing explanation
Fig. 1 is the structural formula of 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine, and Fig. 2 is the building-up reactions equation of 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine.
Embodiment
The present invention adopts dynamic potential polarization curve and electrochemical AC impedance two kinds of electrochemical methods to carry out corrosion inhibition evaluation to inhibiter.Although the inhibition efficiency of two kinds of method acquisitions has difference a little, the general trend of two kinds of methods is basic coincideing, and can find out that this compound all has excellent corrosion inhibition at different conditions.
Embodiment 1
The synthesis of 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine, its final chemical reaction process such as formula two is:
First the p-methyl aceto phenone of mol ratio 1:1 and 2 thiophene carboxaldehyde are reacted in the ethanolic soln of potassium hydroxide, stirring reaction 12h under normal temperature, decompress filter obtains lurid 1-p-methylphenyl-3-(2-thienyl) acrylketone, 1-p-methylphenyl-3-(2-thienyl) acrylketone obtained and O-Phenylene Diamine are reacted in acetic acid and dimethyl formamide mixing solutions, oil bath reflux, magnetic agitation 12h, refrigerator freezing spends the night 12h, decompress filter obtains brown crude product, then through washing, Recrystallisation from acetic acid obtains light yellow crystal, be product 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine.
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, being immersed in by carbon steel electrode adds in the medium of inhibiter, soak 1h, temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.005g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 83.7%, electrochemical impedance spectroscopy 85.8%, shows that this inhibiter has the advantage that consumption is low, efficiency is high thus.
Embodiment 2
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, being immersed in by carbon steel electrode adds in the medium of inhibiter, soak 1h, temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.010g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 88.9%, electrochemical impedance spectroscopy 90.6%, shows that this inhibiter has the advantage that consumption is low, efficiency is high thus.
Embodiment 3
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, being immersed in by carbon steel electrode adds in the medium of inhibiter, soak 1h, temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.015g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 91.2%, electrochemical impedance spectroscopy 92.5%, shows that this inhibiter has the advantage that consumption is low, efficiency is high thus.
Embodiment 4
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, being immersed in by carbon steel electrode adds in the medium of inhibiter, soak 1h, temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.020g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 93.1%, electrochemical impedance spectroscopy 94.4%, shows that this inhibiter has the advantage that consumption is low, efficiency is high thus.
Embodiment 5
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 1h, , temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 96.5%, electrochemical impedance spectroscopy 97.3%, shows that this inhibiter has the advantage that consumption is low, efficiency is high thus.
Embodiment 6
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 10 days, , temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
By experiment test obtain inhibition efficiency be respectively: dynamic potential polarization curve 97.4%, electrochemical impedance spectroscopy 98.2%, show thus this inhibiter there is the long period under high inhibition efficiency.
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental by embodiment 7, condition: experiment material is Q235 carbon steel, composition is (mass%): C 0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 20 days, temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
By experiment test obtain inhibition efficiency be respectively: dynamic potential polarization curve 98.1%, electrochemical impedance spectroscopy 98.8%, show thus this inhibiter there is the long period under high inhibition efficiency.
Embodiment 8
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C 0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 2.5mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 1h, , temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
Test obtains inhibition efficiency and is respectively by experiment: dynamic potential polarization curve 90.3%, electrochemical impedance spectroscopy 91.2%, shows that this inhibiter is compared with having high inhibition efficiency under highly acidity thus.
Embodiment 9
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 5.0mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 1h, , temperature is 25 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
Test obtains inhibition efficiency and is respectively by experiment: dynamic potential polarization curve 83.2%, electrochemical impedance spectroscopy 84.1%, shows that this inhibiter is compared with having high inhibition efficiency under highly acidity thus.
Embodiment 10
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 1h, , temperature is 35 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 93.5%, electrochemical impedance spectroscopy 94.4%, shows that this inhibiter has high inhibition efficiency at relatively high temperatures thus.
Embodiment 11
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 1h, , temperature is 45 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 91.6%, electrochemical impedance spectroscopy 92.7%, shows that this inhibiter has high inhibition efficiency at relatively high temperatures thus.
Embodiment 12
Above-mentioned gained compound is carried out corrosion inhibition evaluation experimental, condition: experiment material is Q235 carbon steel, composition is (mass%): C0.17, Si 0.46, Mn 0.0047, S 0.17, P 0.0047, all the other are Fe, 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine is made into inhibiter, medium is the hydrochloric acid soln of 1.0mol/L, ultrasonic dissolution 30min, carbon steel electrode is immersed in the medium adding inhibiter and soaks 1h, , temperature is 55 DEG C, wherein consumption is 0.5L, 2-(2-thienyl)-4-p-methylphenyl [1 in medium, 5] Benzodiazepine add-on is 0.050g.
Test acquisition inhibition efficiency is respectively by experiment: dynamic potential polarization curve 89.9%, electrochemical impedance spectroscopy 90.6%, shows that this inhibiter has high inhibition efficiency at relatively high temperatures thus.
Claims (7)
1. one kind [1,5] Benzodiazepine compounds is as the application of efficient acidification corrosion inhibitor, it is characterized in that: [1,5] Benzodiazepine compounds is 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine, structural formula is such as formula shown in one:
Formula one.
2. one kind according to claim 1 [1, 5] preparation of Benzodiazepine compounds, it is characterized in that: first 2 thiophene carboxaldehyde and p-methyl aceto phenone are reacted in the ethanolic soln of potassium hydroxide, stirring reaction 12h under normal temperature, decompress filter obtains lurid 1-p-methylphenyl-3-(2-thienyl) acrylketone, 1-p-methylphenyl-3-(2-thienyl) acrylketone obtained and O-Phenylene Diamine are reacted in acetic acid and dimethyl formamide mixing solutions, oil bath reflux, magnetic agitation 12h, refrigerator freezing spends the night 12h, through decompress filter, washing, Recrystallisation from acetic acid obtains product 2-(2-thienyl)-4-p-methylphenyl [1, 5] Benzodiazepine.
3. by according to claim 2 [1,5] preparation of Benzodiazepine compounds, it is characterized in that: described 1-p-methylphenyl-3-(2-thienyl) acrylketone and O-Phenylene Diamine react in acetic acid and dimethyl formamide mixing solutions, oil bath reflux, magnetic agitation 12h, refrigerator freezing spends the night 12h, decompress filter, washing, Recrystallisation from acetic acid.
4. one kind according to claim 1 [1,5] application of Benzodiazepine compounds, it is characterized in that: described 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine can be used as carbon steel hydrochloric acid pickling corrosion inhibitor, carries out corrosion prevention to the steel article in hydrochloric acid medium.
5. the application of [1,5] Benzodiazepine compounds according to claim 4, is characterized in that: the hydrochloric acid soln of described hydrochloric acid medium to be volumetric molar concentration be 1.0 ~ 5.0mol/L.
6. according to claim 4 [1,5] application of Benzodiazepine compounds, it is characterized in that: described employing 2-(2-thienyl)-4-p-methylphenyl [1,5] when Benzodiazepine is as hydrochloric acid pickling corrosion inhibitor, 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine is dissolved in the hydrochloric acid soln of 1.0mol/L, then at room temperature to mixing solutions ultrasonic disperse 30min, make it to dissolve completely, stirring at room temperature evenly.
7. according to claim 4 [1,5] application of Benzodiazepine compounds, it is characterized in that: steel article is immersed in and adds in the 1.0mol/L hydrochloric acid soln of inhibiter, Immersion time is no less than 1h, submergence temperature is 25 ~ 55 DEG C, wherein in often liter of hydrochloric acid soln, 2-(2-thienyl)-4-p-methylphenyl [1,5] Benzodiazepine add-on is 10 ~ 100mg.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410459458.3A CN104232073B (en) | 2014-09-10 | 2014-09-10 | Preparation method of [1,5] benzodiazepine compound and application of [1,5] benzodiazepine compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410459458.3A CN104232073B (en) | 2014-09-10 | 2014-09-10 | Preparation method of [1,5] benzodiazepine compound and application of [1,5] benzodiazepine compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104232073A true CN104232073A (en) | 2014-12-24 |
| CN104232073B CN104232073B (en) | 2017-01-18 |
Family
ID=52220994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410459458.3A Active CN104232073B (en) | 2014-09-10 | 2014-09-10 | Preparation method of [1,5] benzodiazepine compound and application of [1,5] benzodiazepine compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104232073B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107602585A (en) * | 2017-10-23 | 2018-01-19 | 遵义医学院 | The preparation technology of thienopyridine bis-heterocyclic compounds |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453279A (en) * | 1963-11-27 | 1969-07-01 | Hoffmann La Roche | 2-dihalo lower alkyl-4-phenyl-quinazoline 3-oxide |
| CN102585796A (en) * | 2012-01-13 | 2012-07-18 | 西南石油大学 | Acidizing corrosion inhibitor N-(gamma-methylanthracene) pyridine chloride and preparation method thereof |
| CN103225083A (en) * | 2013-03-28 | 2013-07-31 | 中国科学院海洋研究所 | Application of acethydrazide type compound containing thiophene heterocycle and being used as corrosion inhibitor |
| CN103508570A (en) * | 2012-06-25 | 2014-01-15 | 上海思曼泰化工科技有限公司 | Environmental protection and high efficiency corrosion inhibitor for inhibiting salt water corrosion on carbon steel, preparation method and use method thereof |
-
2014
- 2014-09-10 CN CN201410459458.3A patent/CN104232073B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453279A (en) * | 1963-11-27 | 1969-07-01 | Hoffmann La Roche | 2-dihalo lower alkyl-4-phenyl-quinazoline 3-oxide |
| CN102585796A (en) * | 2012-01-13 | 2012-07-18 | 西南石油大学 | Acidizing corrosion inhibitor N-(gamma-methylanthracene) pyridine chloride and preparation method thereof |
| CN103508570A (en) * | 2012-06-25 | 2014-01-15 | 上海思曼泰化工科技有限公司 | Environmental protection and high efficiency corrosion inhibitor for inhibiting salt water corrosion on carbon steel, preparation method and use method thereof |
| CN103225083A (en) * | 2013-03-28 | 2013-07-31 | 中国科学院海洋研究所 | Application of acethydrazide type compound containing thiophene heterocycle and being used as corrosion inhibitor |
Non-Patent Citations (3)
| Title |
|---|
| A.TIMOTOU ET AL.: "Novel synthesis of benzimidazole by ring contraction rearrangement of benzodiazepine", 《INTERNATIONAL JOURNAL OF BIOLOGICAL AND CHEMICAL SCIENCES》 * |
| K.ISHWAR BHAT ET AL.: "Synthesis,Pharmacological,and Biological Screening of Novel Derivatives of Benzodiazepines", 《JOURNAL OF HETEROCYCLIC CHEMISTRY》 * |
| 徐国梅 等: "苯并三氮唑在金属清洗剂中缓蚀性研究", 《皖西学院学报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107602585A (en) * | 2017-10-23 | 2018-01-19 | 遵义医学院 | The preparation technology of thienopyridine bis-heterocyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104232073B (en) | 2017-01-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang | Inhibition of mild steel corrosion in phosphoric acid solution by triazole derivatives | |
| Deng et al. | Alizarin violet 3B as a novel corrosion inhibitor for steel in HCl, H2SO4 solutions | |
| CN102329273B (en) | Schiff base containing nitrogenous heterocyclic compound and preparation method and application thereof | |
| Al-Amiery et al. | Electrochemical studies of novel corrosion inhibitor for mild steel in 1 M hydrochloric acid | |
| CN103555313B (en) | A kind of imidazolium ionic liquid acidification corrosion inhibitor and preparation method thereof and application | |
| Thirumalairaj et al. | Corrosion protection of mild steel by a new binary inhibitor system in hydrochloric acid solution | |
| Berdimurodov et al. | 8–Hydroxyquinoline is key to the development of corrosion inhibitors: An advanced review | |
| CN103881697A (en) | Imidazoline compound corrosion inhibitor and preparation method thereof | |
| CN103046055A (en) | Imidazolyl lysine salt ionic liquid steel corrosion inhibitor and application thereof | |
| CN103820789B (en) | Compositional type carbon dioxide corrosion inhibitor | |
| CN105503855B (en) | A kind of preparation method of thiazole carbon steel restrainer | |
| Manickavasagam et al. | Poly (styrene sulphonic acid)‐doped polyaniline as an inhibitor for the corrosion of mild steel in hydrochloric acid | |
| Guo et al. | Extraction of a high efficiency and long-acting green corrosion inhibitor from silkworm excrement and its adsorption behavior and inhibition mechanism on copper | |
| Yang et al. | Indolizine quaternary ammonium salt inhibitors, part III: Insights into the highly effective low-toxicity acid corrosion inhibitor–synthesis and protection performance | |
| CN104232073A (en) | Preparation method of [1,5] benzodiazepine compound and application of [1,5] benzodiazepine compound | |
| CN107988601A (en) | A kind of hydrotalcite intercalation 5- methyl isophthalic acids, 3,4,-thiadiazoles -2- sulfydryls corrosion inhibitor and its application | |
| CN104357859A (en) | Preparation method and application of sulfo-formamyl pyrazoline compound | |
| CN103225083B (en) | A kind of application of acethydrazide compound as inhibiter containing thiophene heterocycle | |
| Wang et al. | High-efficiency corrosion inhibitor for acidizing: synthesis, characterization and anti-corrosion performance of novel indolizine derivative | |
| Al-Jeilawi et al. | Corrosion Inhibition Effects of Some New Synthesized N-Aroyl-N-Aryl thiourea Derivatives for Carbon Steel in Sulfuric Acid Media | |
| Yang et al. | Investigation of high-efficient acidizing inhibitors: structure and anti-corrosion performance of novel indolizine derivatives | |
| CN108341809A (en) | A kind of steel corrosion inhibitor and its preparation method and application | |
| CN109265456A (en) | A kind of preparation method and applications of thiazolyl-dihydro pyrazole compound | |
| CN103102311A (en) | Cinnamyl imidazoline derivative and its preparation method and use | |
| CN102433564A (en) | Preparation method of Schiff-base corrosion inhibitor by condensation of o-oxy-acetate-benzaldehyde and substituted aniline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20180925 Address after: 123100 fluorine chemical park, Fuxin County, Liaoning, Fuxin Patentee after: Fuxin Long Rui Pharmaceutical Co., Ltd. Address before: 256603 391 the Yellow River five road, Bincheng District, Binzhou, Shandong Patentee before: Binzhou College |