CN109134304A - A kind of preparation method of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter - Google Patents
A kind of preparation method of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter Download PDFInfo
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- CN109134304A CN109134304A CN201811035938.1A CN201811035938A CN109134304A CN 109134304 A CN109134304 A CN 109134304A CN 201811035938 A CN201811035938 A CN 201811035938A CN 109134304 A CN109134304 A CN 109134304A
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- corrosion inhibiter
- vanillin
- propane diamine
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- schiff bases
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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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
- C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
- C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
- C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
- C23G1/068—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors compounds containing a C=C bond
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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
- C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
- C23G1/08—Iron or steel
- C23G1/081—Iron or steel solutions containing H2SO4
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation methods of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter.(1) it measures 1.1411 g o-vanillins to be placed in the round-bottomed flask for filling 15mL dehydrated alcohol, magnetic agitation is uniform.(2) 0.1853g is added and analyzes pure 1,2- propane diamine and 0.15mL glacial acetic acid, 65 DEG C are stirred, and back flow reaction 6 hours, whole nitrogen protection.(3) it cools down at room temperature, decompression filters, and is constantly eluted with dehydrated alcohol, takes out filter cake, filter cake is dried in vacuo, is placed into the beaker equipped with 40mL dehydrated alcohol, suction filtration is depressurized in stirring again, it takes filter cake to be dried in vacuo, obtains 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter.Corrosion inhibiter can be used for the anticorrosion in pickling solution to carbon steel.Present invention process is simple, reproducible, yield is high；Corrosion inhibiter is good to the corrosion mitigating effect of dilute sulfuric acid medium carbon steel.
Description
Technical field
The present invention relates to organic synthesis fields, are related to a kind of preparation method of bis-schiff base-containing corrosion inhibiter, and in particular to one
The preparation method of kind 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter.
Background technique
The history of existing more than 100 years of the application of carbon steel corrosion inhibitor, domestic corrosion inhibiter research were started in for the 50's with application
Aniline-aldehyde condensation polymer object, start to rapidly develop after the seventies.It is domestic from imitated foreign countries' Rodine, Nbit product to being formed
The seriations corrosion inhibitor formulas such as quaternary ammonium salt (IMC), organic amine (SH), composite corrosion inhibitor (FH), river day, 7081, technology
Performance has been approached advanced international standard.Some corrosion inhibiter have reached in terms of water process and souring operation or are more than external similar production
Product.Currently, corrosion inhibiter just slowly changes to environment-friendly corrosion inhibitor, to reduce corrosion of carbon steel and to the pollution of environment.
Domestic carbon steel corrosion inhibitor type mainly has imidazoline type, schiff's base type, quaternary, alkynol type, pyridine type etc.,
Wherein schiff's base type corrosion inhibiter has synthesis simply, low in cost, the good advantage of corrosion mitigating effect.In schiff base compounds containing N,
O, S hetero atom and unsaturation C=N key, easily form firm and stable chemical bond, to slow down in metal surface in the solution
Acid solution has excellent corrosion inhibition to corrosion of metal, to carbon steel.Simultaneously schiff bases have it is at low cost, be easily-synthesized and purify,
Good water solubility, nontoxicity and it is many kinds of the features such as, the favor by corrosion inhibiter researcher.
From the point of view of the development status of schiff bases corrosion inhibiter, research work relates generally to corrosion inhibiter pair under normal temperature and pressure
The inhibition of acid solution medium carbon steel, there are the problem of mainly have the following:
(1) research Schiff bases corrosion inhibiter use condition is more single both at home and abroad at present, and the temperature of oil field, building, power generation etc.
Degree pressure is very high, and corrosion suffered by equipment is just more serious, and common acidification corrosion inhibitor is easy under high temperature or extremely low temperature both at home and abroad at present
Coking, dissolution dispersity are poor, therefore corrosion inhibiter performance is greatly reduced, and corrosion mitigating effect is undesirable.
(2) for carbon steel material is not had to, the anticorrosion research in different acid mediums also needs to further investigate.
(3) compounding of corrosion inhibiter can increase adsorption coverage and absorption stability, reduce inhibiter consumption and reduce at
This, while improving corrosion inhibition.The synergistic effect mechanism of schiff bases corrosion inhibiter and other organic matters is studied, there are no understand fully.
(4) schiff bases corrosion inhibiter is incomplete and mature in practice.Especially environment-friendly corrosion inhibitor is ground
Study carefully still in the experimental exploring stage, it is still necessary to be done in terms of improving inhibition efficiency, mechanism study and inexpensive low pollution
Deeper into research.
The invention discloses the preparation methods of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter.The method be with
1,2- propane diamine and o-vanillin are raw material, using glacial acetic acid as catalyst, can prepare the double seats of 1,2- Propane Diamine o-vanillin
Husband's alkali corrosion inhibiter.
Summary of the invention
The object of the present invention is to provide the preparation methods of one kind 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter.
Specific steps are as follows:
(1) it measures 1.1411g o-vanillin to be placed in the round-bottomed flask for filling 15mL dehydrated alcohol, magnetic agitation is uniform.
(2) pure 1, the 2- propane diamine of analysis and the 0.15mL analysis that 0.1853g is added dropwise into step (1) gains are pure
Glacial acetic acid catalyst, under 65 DEG C of constant temperatures, magnetic agitation, back flow reaction 6 hours, whole nitrogen protection.
(3) step (2) acquired solution is cooled down at room temperature, there are a large amount of light yellow crystals to be precipitated, decompression filters, with anhydrous second
Alcohol constantly elutes, and takes out filter cake, filter cake is dried in vacuo, is placed into the beaker equipped with 40mL dehydrated alcohol, magnetic force stirs
It mixes 2 hours, to remove the impurity such as excessive o-vanillin, glacial acetic acid, then depressurizes suction filtration, take filter cake to be dried in vacuo, finally obtain
1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter.
1, the 2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter can be used for the anticorrosion in pickling solution to carbon steel, and 1,
The dosage of 2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter energy is 0.001-0.01mol/L.
The present invention has many advantages, such as that simple process, reproducible, yield is high；1,2- Propane Diamine o-vanillin Bis-Schiff Bases
Corrosion inhibiter is applied in pickling solution, and the inhibition to carbon steel works well.
Detailed description of the invention
Fig. 1 is 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter infrared spectrogram in the embodiment of the present invention.
Fig. 2 is the nuclear magnetic resonance spectroscopy of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter in the embodiment of the present invention
Figure.
Specific embodiment
The present invention is furture elucidated combined with specific embodiments below, but embodiment is not intended to limit protection scope of the present invention.
Embodiment:
Prepare the specific steps of above-mentioned 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter are as follows:
(1) it measures 1.1411g o-vanillin to be placed in the round-bottomed flask for filling 15mL dehydrated alcohol, magnetic agitation is uniform.
(2) pure 1, the 2- propane diamine of analysis and the 0.15mL analysis that 0.1853g is added dropwise into step (1) gains are pure
Glacial acetic acid catalyst, under 65 DEG C of constant temperatures, magnetic agitation, back flow reaction 6 hours, whole nitrogen protection.
(3) step (2) acquired solution is cooled down at room temperature, there are a large amount of light yellow crystals to be precipitated, decompression filters, with anhydrous second
Alcohol constantly elutes, and takes out filter cake, filter cake is dried in vacuo, is placed into the beaker equipped with 40mL dehydrated alcohol, magnetic force stirs
It mixes 2 hours, to remove the impurity such as excessive o-vanillin, glacial acetic acid, then depressurizes suction filtration, take filter cake to be dried in vacuo, finally obtain
0.6529g 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter, yield 64.96%, m.p.118.7~120.8 DEG C.
Reaction equation is as follows:
It is double to prepared 1,2- Propane Diamine o-vanillin using KBr tabletting using VECTOR22 type infrared spectrometer
Schiff bases corrosion inhibiter scans within the scope of 4000~500cm-1, carries out infrared spectroscopy structural characterization.By attached drawing 1 it is found that
3411cm-1 does not nearby have the stretching vibration peak of appearance-NH2, without the flexible of discovery aldehyde radical (- COH) near 1653 cm-1
Vibration peak, and there is new chemical bond C=N double bond, illustrate to generate schiff bases.
Using AUANCEAv500Hz NMR spectrometer with superconducting magnet, with 1.0 × 10-4The methylene chloride of mol/L corrosion inhibiter
Or dimethyl sulfoxide or chloroform make solvent, carry out to prepared 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter
Nuclear magnetic resonance spectroscopy test.It is two hydrogen originals of two-CH=N- groups at 8.31ppm and at 8.35ppm as shown in attached drawing 2
Two peaks of son, the place 6.92ppm are the multiplet for aligning upper hydrogen atom on phenyl ring with methoxyl group, the place 6.86ppm be on phenyl ring and
The multiplet of hydrogen atom in hydroxyl contraposition, the place 6.79 ppm are the multiplet of the hydrogen atom on phenyl ring in methoxyl group adjacent bit,
It is the multiplet of six hydrogen atoms on two methoxyl groups being connected with phenyl ring at 3.92ppm, is N-CH-C skeleton hydrogen at 3.70ppm
The doublet of atom is C-CH at 3.77ppm2The doublet of-N skeleton hydrogen atom, at 1.43ppm on methyl hydrogen atom it is double
Weight peak, does not find the peak of hydrogen atom on hydroxyl at 5ppm, may be deuterated by deuterated reagent.6.86ppm is deuterated dichloromethane
It is Chong Die with the hydrogen atom in hydroxyl contraposition on the peak phenyl ring of alkane solvents remnants hydrogen atom.Hydrogen nuclear magnetic resonance spectrum analysis result and 1,2-
Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter structural formula matches.
1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter corrosion mitigating effect is taken using weight-loss method investigation.Drying for standby
3 groups of experiment carbon steel sample precises on assay balance, processed low-carbon steel disc is immersed in and does not add and add difference
Concentration is respectively 0.001mol/L, 0.005mol/L, 0.01mol/L 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter
50mL1mol/L dilute sulfuric acid in, impregnated 4 hours at 30 DEG C.Sample is then taken out, with distilled water flushing, is dehydrated in ethyl alcohol, third
Degreasing in ketone is weighed after 4 hours dry.Parallel test three times, calculates corrosion inhibition rate.0.001mol/L, 0.005mol/L,
0.01mol/L1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter is respectively to the corrosion inhibition rate of dilute sulfuric acid medium carbon steel
36.58%, 59.58%, 65.88%.
Claims (2)
1. one kind 1, the preparation method of 2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter, it is characterised in that specific steps are as follows:
(1) it measures 1.1411 g o-vanillins to be placed in the round-bottomed flask for filling 15mL dehydrated alcohol, magnetic agitation is uniform；
(2) the pure 1,2- propane diamine of analysis and 0.15mL that 0.1853 g is added dropwise into step (1) gains analyze pure ice vinegar
Acid catalyst, under 65 DEG C of constant temperatures, magnetic agitation, back flow reaction 6 hours, whole nitrogen protection；
(3) step (2) acquired solution is cooled down at room temperature, there are a large amount of light yellow crystals to be precipitated, decompression filters, and is drenched with dehydrated alcohol
It washes, takes out filter cake, filter cake is dried in vacuo, is placed into the beaker equipped with 40mL dehydrated alcohol, magnetic agitation 2 hours,
Suction filtration is depressurized again, filter cake is taken to be dried in vacuo, and obtains 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter.
2. the application of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter according to claim 1, it is characterised in that institute
Anticorrosion in pickling solution to carbon steel, 1,2- Propane Diamine can be used for by stating 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter
The dosage of o-vanillin Bis-Schiff Bases corrosion inhibiter energy is 0.001-0.01 mol/L.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811035938.1A CN109134304A (en) | 2018-09-06 | 2018-09-06 | A kind of preparation method of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter |
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| CN201811035938.1A CN109134304A (en) | 2018-09-06 | 2018-09-06 | A kind of preparation method of 1,2- Propane Diamine o-vanillin Bis-Schiff Bases corrosion inhibiter |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103642547A (en) * | 2013-12-24 | 2014-03-19 | 济南开发区星火科学技术研究院 | Compound diesel additive and preparation method thereof |
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2018
- 2018-09-06 CN CN201811035938.1A patent/CN109134304A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103642547A (en) * | 2013-12-24 | 2014-03-19 | 济南开发区星火科学技术研究院 | Compound diesel additive and preparation method thereof |
Non-Patent Citations (5)
| Title |
|---|
| M.G. HOSSEINI等: "Protection of mild steel corrosion with Schiff bases in 0.5M H2SO4 solution", 《ELECTROCHIMICA ACTA》 * |
| RAYATI, SAEED 等: "Electronic effects of substituents on the oxidation potentials of vanadyl complexes with tetradentate Schiff base ligands derived from 1,2-propylenediamine", 《CATALYSIS COMMUNICATIONS》 * |
| WU,JIANFENG 等: "Enhancement of Magnetocaloric Effect through Fixation of Carbon Dioxide:Molecular Assembly from Ln4 to Ln4 Cluster Pairs", 《INORGANIC CHEMISTRY》 * |
| 石晶 等: "一种席夫碱的合成及其缓蚀性能研究", 《清洗世界》 * |
| 齐德强 等: "新型席夫碱的合成及光学性质研究", 《广东化工》 * |
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Application publication date: 20190104 |