CN109206338A - A kind of preparation method of 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter - Google Patents

A kind of preparation method of 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter Download PDF

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Publication number
CN109206338A
CN109206338A CN201811035887.2A CN201811035887A CN109206338A CN 109206338 A CN109206338 A CN 109206338A CN 201811035887 A CN201811035887 A CN 201811035887A CN 109206338 A CN109206338 A CN 109206338A
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dibromosalicylaldehyde
corrosion inhibiter
propane diamine
bis
schiff bases
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刘峥
韩佳星
梁楚欣
李汝
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Guilin University of Technology
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Guilin University of Technology
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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
    • 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
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)

Abstract

The invention discloses a kind of preparation methods of 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter.(1) by 2.0993g 3,5- Dibromosalicylaldehyde is placed in the round-bottomed flask for filling 15mL dehydrated alcohol, stirs evenly.(2) 0.1853g is added and analyzes pure 1,2- propane diamine and 0.15mL glacial acetic acid, under 65 DEG C of constant temperatures, stirring, back flow reaction 6 hours, whole nitrogen protection.(3) it cools down at room temperature, decompression filters, and is eluted with dehydrated alcohol, filter cake is dried in vacuo, it places into the beaker equipped with 40mL dehydrated alcohol, suction filtration is depressurized in stirring again, and filter cake is taken to be dried in vacuo, obtain 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde 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

A kind of preparation of 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter Method
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 3,5- Dibromosalicylaldehyde 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 are started in the fifties with application Aniline-aldehyde condensation polymer object, started to rapidly develop after the seventies.From imitated foreign countries' Rodine, Nbit product to formation domestic season The seriations corrosion inhibitor formulas such as ammonium salt class (IMC), organic amine (SH), composite corrosion inhibitor (FH), river day, 7081, it is technical Advanced international standard can be had been approached.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 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter.The side Method is with 1,2- propane diamine and 3, and 5- Dibromosalicylaldehyde can prepare 1,2- Propane Diamine using glacial acetic acid as catalyst for raw material 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter.
Summary of the invention
The object of the present invention is to provide a kind of 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter of preparing Preparation method.
Specific steps are as follows:
(1) 2.0993g 3 is measured, 5- Dibromosalicylaldehyde is placed in the round-bottomed flask for filling 15mL dehydrated alcohol, and magnetic force stirs It mixes uniformly.
(2) 0.1853g is added dropwise into step (1) gains and analyzes pure 1,2- propane diamine and the pure ice vinegar of 0.15mL analysis 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 3,5- Dibromosalicylaldehyde, glacial acetic acid, then depressurizes suction filtration, take filter cake to be dried in vacuo, most After obtain 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter.
Obtained 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter can be used in pickling solution to carbon steel Anticorrosion, the dosage of the corrosion inhibiter 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 3,5- Dibromosalicylaldehyde is double 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 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter infrared spectroscopy in the embodiment of the present invention Figure.
Fig. 2 is the nuclear magnetic resonance of 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter in the embodiment of the present invention Hydrogen spectrogram.
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:
(1) 3, the 5- Dibromosalicylaldehyde for measuring 2.0993g is placed in the round-bottomed flask for filling 15mL dehydrated alcohol, and magnetic force stirs It mixes uniformly.
(2) the pure 1,2- propane diamine of analysis and 0.15mL that 0.1853g is added dropwise into step (1) gains analyze pure ice Acetate 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 3,5- Dibromosalicylaldehyde, glacial acetic acid, then depressurizes suction filtration, take filter cake to be dried in vacuo, obtain 1, the 2- Propane Diamine 3 of 0.9667g, 5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter, yield 81.10%, m.p.156-158 DEG C.
Reaction equation is as follows:
Using VECTOR22 type infrared spectrometer, using KBr tabletting, to prepared 1,2- Propane Diamine 3, bis- bromine water of 5- Poplar aldehyde Bis-Schiff Bases corrosion inhibiter is in 4000~500cm-1Scanning in range, carries out infrared spectroscopy structural characterization.By attached drawing 1 it is found that In 3411cm-1There is no discovery-NH nearby2Stretching vibration peak, in 1660cm-1Nearby without discovery aldehyde radical (- COH) stretching vibration Peak, and there is new chemical bond C=N characteristic absorption peak, illustrate to generate schiff bases.
Using AUANCEAv500Hz NMR spectrometer with superconducting magnet, with the methylene chloride of 1.0 × 10-4mol/L corrosion inhibiter Or dimethyl sulfoxide or chloroform make solvent, to prepared 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases inhibition Agent carries out nuclear magnetic resonance spectroscopy test.It is the double of two hydrogen atoms of two-CH=N- groups at 8.36ppm as shown in attached drawing 2 Peak is the doublet of a hydrogen atom on-C=CH- on phenyl ring at 7.45ppm, and the place 5.37ppm is in two aromatic rings on hydroxyl The multiplet of hydrogen atom is the triplet of two hydrogen atoms on C-CH2-N skeleton at 3.81ppm, and 2.20ppm is deuterated dimethyl The peak of remaining hydrogen atom in sulfoxide solvent, the place 1.45ppm are the double peak of three hydrogen atoms on methyl.Nuclear magnetic resonance spectroscopy point Analysis result matches with 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter structural formula.
1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibitor inhibition is taken to imitate using weight-loss method investigation Fruit.3 groups of experiment carbon steel sample precises on assay balance of drying for standby, processed low-carbon steel disc is immersed in and is not added Adduction addition various concentration is respectively 0.001mol/L, 0.005mol/L, 0.01mol/L1,2- Propane Diamine 3,5- dibromo bigcatkin willow In the 50mL 1mol/L dilute sulfuric acid of aldehyde Bis-Schiff Bases corrosion inhibitor, impregnated 4 hours at 30 DEG C.Sample is then taken out, with steaming Distilled water is rinsed, and is dehydrated in ethyl alcohol, degreasing in acetone, 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 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibitor Corrosion inhibition rate to dilute sulfuric acid medium carbon steel is respectively 36.65%, 45.33%, 62.24%.

Claims (2)

1. one kind 1,2- Propane Diamine 3, the preparation method of 5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter, it is characterised in that specific step Suddenly are as follows:
(1) 3, the 5- Dibromosalicylaldehyde for measuring 2.0993g is placed in the round-bottomed flask for filling 15mL dehydrated alcohol, magnetic agitation Uniformly；
(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, not with dehydrated alcohol Disconnected elution, takes out filter cake, filter cake is dried in vacuo, is placed into the beaker equipped with 40mL dehydrated alcohol, magnetic agitation 2 is small When, to remove the impurity such as excessive 3,5- Dibromosalicylaldehyde, glacial acetic acid, then suction filtration is depressurized, takes filter cake to be dried in vacuo, finally obtain 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter.
2. 1,2- Propane Diamine 3 according to claim 1, the application of 5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter, feature It is that the 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter can apply to the anti-corrosion in pickling solution to carbon steel Erosion, 1,2- Propane Diamine 3, the dosage of 5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter are 0.001-0.01 mol/L.
CN201811035887.2A 2018-09-06 2018-09-06 A kind of preparation method of 1,2- Propane Diamine 3,5- Dibromosalicylaldehyde Bis-Schiff Bases corrosion inhibiter Pending CN109206338A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110552008A (en) * 2019-09-19 2019-12-10 桂林理工大学 Preparation method and application of 2, 6-pyridine dimethyl acetal 2-aminofluorene Schiff base corrosion inhibitor
CN110724959A (en) * 2019-09-19 2020-01-24 桂林理工大学 Preparation method and application of bromopropanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor
CN114105812A (en) * 2020-08-26 2022-03-01 中国石油化工股份有限公司 Method for synthesizing N, N' -bis (salicylidene) -1, 2-propane diamine by using chloropropene byproduct 1, 2-dichloropropane

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WO2014047180A1 (en) * 2012-09-21 2014-03-27 Exxonmobil Research And Engineering Company Lubricant and fuel dispersants and methods of preparation thereof
CN107573366A (en) * 2017-09-17 2018-01-12 桂林理工大学 The preparation method of 2-carboxybenzaldehyde 1,3 propane diamine schiff bases copper complexes of contracting

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110552008A (en) * 2019-09-19 2019-12-10 桂林理工大学 Preparation method and application of 2, 6-pyridine dimethyl acetal 2-aminofluorene Schiff base corrosion inhibitor
CN110724959A (en) * 2019-09-19 2020-01-24 桂林理工大学 Preparation method and application of bromopropanedialdehyde 2-aminofluorene bis-Schiff base corrosion inhibitor
CN114105812A (en) * 2020-08-26 2022-03-01 中国石油化工股份有限公司 Method for synthesizing N, N' -bis (salicylidene) -1, 2-propane diamine by using chloropropene byproduct 1, 2-dichloropropane

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