CN107459473A - A kind of methionine derivative corrosion inhibiter and its synthetic method for pickling iron and steel - Google Patents
A kind of methionine derivative corrosion inhibiter and its synthetic method for pickling iron and steel Download PDFInfo
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- CN107459473A CN107459473A CN201710878406.3A CN201710878406A CN107459473A CN 107459473 A CN107459473 A CN 107459473A CN 201710878406 A CN201710878406 A CN 201710878406A CN 107459473 A CN107459473 A CN 107459473A
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- methionine
- thionyl chloride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide 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
- C23G1/065—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors sulfur-containing compounds
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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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Abstract
A kind of methionine derivative corrosion inhibiter and its synthetic method for pickling iron and steel, the methionine derivative corrosion inhibiter it is entitled：The methyl mercapto N octyl group butyramides of 2 amino 3, the derivative can spontaneously, effectively adsorb carbon steel surface, and based on chemisorbed, absorption affinity is stronger.Because the carbochain of introducing is 8 carbon atoms so that derivative is water-soluble preferable in the range of concentration, and corrosion inhibition rate is up to more than 98%.
Description
Technical field
This patent disclosure relates generally to a kind of restrainer, and in particular to a kind of methionine derivative for pickling iron and steel delays
Lose agent and its synthetic method.
Background technology
Recovered the oil etc. in sour environment in acid dipping, process equipment pickling descaling and acidifying, steel corrosion be it is a kind of extremely
Important destructive factor.Heavy corrosion caused by order to prevent pickling, addition corrosion inhibiter is a kind of extremely simple and effective side
Method.As environmental consciousness constantly strengthens the constantly improve with environmental regulation, at present there is an urgent need to develop it is nontoxic, can biology drop
The corrosion inhibiter of solution is come the virose corrosion inhibiter that substitutes those to apply in early days.The natural corrosion inhibiter extracted from plant and some nothings
The harmless organic inhibitor of poison is applied in many corrosion systems.Application of the amino acid in terms of corrosion inhibition for metal, it is inhibition
The Non-toxic of agent and efficient utilize open new field.Amino acid is obtained with higher in relatively simple production technology
Purity (>99%), production cost is relatively low, and dissolubility in aqueous is preferable, nontoxic to environment, biodegradable,
It is a kind of corrosion inhibiter for having very much development potentiality.
More as the research report of restrainer to amino acid both at home and abroad in the last few years, researcher is mainly from 20 kinds of marks
Several representational amino acid are filtered out in quasi- amino acid, carry out the comparison of corrosion mitigating effect, so as to study its inhibition mechanism.
M.Zerfaoui et al. uses weight-loss method, method of polarization curve and Study on AC impedance glycine, leucine, aspartic acid, essence
Several amino acid such as propylhomoserin and methionine are in pH=5 citric acid to the corrosion inhibition of iron.H.Ashassi-Sorkhabi etc.
People determines three kinds of amino acid such as alanine, glycine and leucine with electrokinetic potential polarozation curve method and carbon steel is delayed in hydrochloric acid
Erosion acts on.
With deepening continuously for research, it has been found that the amino acid of some sulfur atom-containings, such as methionine and cysteine, remove
Outside nitrogen-atoms, also contain sulphur atom, absorption that can be stronger suppresses the generation of corrosion, therefore have in metal surface
There is more excellent corrosion inhibition.Because molecular structure is simple, in metal surface, adsorptivity is not strong, adds for methionine or cysteine
Dosage is larger.In order to further improve corrosion inhibition rate, addition is reduced, researcher starts the derivative of synthesizing amino acid.
It is more at this stage directly as corrosion inhibiter or to be oxidized by the use of methionine as methionine sulfoxide, addition 250mgL-1
Methionine is 72.08% as corrosion inhibition rate of the inhibition to N80 in 3%NaCl solution.He Yi et al. is further improved (in
State patent CN105622471A), prepare into Fmoc- methionine amides, in 3%NaCl solution, addition 250mg
L-1When, 86.94% can be reached to N80 corrosion inhibition rate, corrosion inhibition rate has large increase.However, Fmoc- methionine amides are main
It is for the corrosion inhibiter in neutral NaCl watery solution, is had not been reported for the methionine derivative corrosion inhibiter in pickle.In addition,
Long chain hydrocarbon groups of the Fmoc- methionine amides due to introducing two phenyl ring and 18 carbon on methionine molecule so that final production
Product water solubility is bad.
The content of the invention
The invention aims to overcome above-mentioned of the prior art some or some problem, there is provided one kind is used for steel
The Novel egg threonine derivative corrosion inhibiter and its synthetic method of pickling.
According to the first aspect of the invention, there is provided a kind of methionine derivative corrosion inhibiter for pickling iron and steel, the egg ammonia
Acid derivative corrosion inhibiter it is entitled：2- amino -3- methyl mercaptos-N- octyl groups-butyramide, chemical structural formula are：
。
According to the second aspect of the invention, there is provided a kind of synthetic method of Novel egg threonine derivative corrosion inhibiter, synthesize road
Line is：
Under concrete condition, the synthetic method is divided into three steps：The preparation of thionyl chloride-methanol solution, methyl methionine
The synthesis of hydrochloride and the synthesis of the amide derivatives of methionine, it is specific as follows：
1) preparation of thionyl chloride-methanol solution
Methanol is added into reaction vessel, ice salt bath is cooled to less than -10 DEG C, stirs lower dropwise addition thionyl chloride, control drop
Acceleration makes reaction temperature be no more than 0 DEG C, is warmed to room temperature naturally after reacting 1h, obtains thionyl chloride-methanol solution, and wherein dichloro is sub-
The concentration of sulfone is 1-2mol/L；
2) synthesis of hydrochloride methyl methionine
Reflux condensing tube, dropping funel and thermometer are installed on three mouthfuls of containers, methanol is added in three mouthfuls of containers, uses ice
Salt bath is cooled to less than -10 DEG C, and thionyl chloride is slowly added dropwise under stirring, controls rate of addition to make reaction temperature not during dropwise addition
More than 0 DEG C, continue to stir；Methionine is added, the mol ratio of wherein methionine and thionyl chloride is：1:1~1:1.5, heating
Backflow, the thionyl chloride with evaporation solvent methanol and excess is evaporated under reduced pressure, to doing, above-mentioned solid is used again obtained in step 1)
Thionyl chloride-methanol solution dissolving, reheats backflow, is evaporated under reduced pressure evaporation solvent, extremely dry, obtains hydrochloride methyl methionine and consolidates
Body；
3) synthesis of the amide derivatives of methionine
The hydrochloride methyl methionine that step 2) is obtained is with n-octyl amine by mol ratio：1:3~1:In 80- after 5 mixing
Stirring reaction at 100 DEG C, after reaction product isopropanol, add alkali lye and neutralized；After filtering, then depressurize steaming
Evaporate, isopropanol and excessive n-octyl amine are removed, add n-hexane to solid precipitation and produce；Solid sediment is isolated, is used
After n-hexane washing, the derivative of dry methionine amide, i.e. 2- amino -3- methyl mercaptos-N- octyl groups-butyryl in atmosphere
Amine.Process conditions in this step are particularly important, control under above-mentioned specific process conditions and parameter, could cause methionine first
The oxygen methyl of ester hydrochloride is substituted by the carbochain of normal octane completely, so as to provide guarantee for the corrosion inhibition of synthetic product.
According to the third aspect of the invention we, there is provided the application of above-mentioned Novel egg threonine derivative corrosion inhibiter, wherein described
Addition concentration of the methionine derivative corrosion inhibiter in pickle is 20-200mg/L.In the case of further preferably, concentration is added
For 50-100mg/L, under the concentration, corrosion inhibition rate is satisfied between 95%-98% so as to reach with less addition
Corrosion mitigating effect.
The present invention has synthesized a kind of Novel egg threonine derivative 2- amino -3- using methionine as raw material using special process
Methyl mercapto-N- octyl groups-butyramide.The derivative contains unpaired electron element N and S, and due to the hydrophobic effect of octyl group, has
Preferable corrosion mitigating effect.Corrosion inhibition rate can reach more than 98%, and steel disc surface is smooth as before, and no spot corrosion and local corrosion show
As.It is probably due to containing two aspect reasons：First, contain two N atoms and a S atom in molecule；Second, the carbon of introducing
Chain makes its water-soluble suitably reduction, diaphragm of formation finer and close, more stable.The derivative spontaneously, effectively adsorb carbon steel
Surface, based on chemisorbed, absorption affinity is stronger.Because the carbochain of introducing is 8 carbon atoms so that derivative is in concentration
In the range of it is water-soluble preferably, corrosion inhibition rate is up to more than 98%.
Brief description of the drawings
Fig. 1 is the infared spectrum for the methionine derivative that the present invention synthesizes；
Fig. 2 is in 30 DEG C of 0.5M H2SO4The carbon steel surface of the methionine derivative of the present invention is added in solution
Langmuir adsorption isotherms.
Embodiment
To absolutely prove the characteristic of the present invention and implementing the mode of the present invention, embodiment is given below.
The entitled 2- amino -3- methyl mercaptos-N- octyl groups-butyramide of methionine derivative synthesized by the present invention, synthesize road
Line is as follows：
It is divided into three steps：The preparation of two sulphur sulfoxides-methanol solution, the synthesis of hydrochloride methyl methionine and methionine
The synthesis of amide derivatives.
1) preparation of thionyl chloride-methanol solution
150mL methanol is added in reaction vessel, ice salt bath is cooled to less than -10 DEG C, 21.60mL is added dropwise under electromagnetic agitation
Thionyl chloride, in order to avoid the chemical reaction of methanol and thionyl chloride therebetween, rate of addition should be controlled to make reaction temperature not
More than 0 DEG C, it is warmed to room temperature naturally after reacting 1h, obtains 150mL 2mol/L thionyl chloride-methanol solution.Above-mentioned solution is shifted
Into brown reagent bottle, sealing, it is kept in dark place.
2) synthesis of hydrochloride methyl methionine
Reflux condensing tube, dropping funel and thermometer are installed on three mouthfuls of containers.50mL methanol is added in reaction bulb, used
Ice salt bath is cooled to less than -10 DEG C, and 3.6mL thionyl chlorides are slowly added dropwise under stirring, and rate of addition and anti-is controlled during dropwise addition
Temperature (less than 0 DEG C) is answered, 10min or so is added dropwise, and continues to stir 1h.Methionine 7.52g is added, is heated to reflux 1h, is depressurized
Distillation is extremely dry with evaporation solvent methanol and the thionyl chloride of excess.In order that the methionine reaction in raw material is abundant, it is pure to obtain
High product is spent, above-mentioned solid need to be dissolved with the methanol solution of 50mL 2mol/L thionyl chlorides again, reheated backflow 1h, subtract
Pressure distillation evaporation solvent, to doing, obtains white solid.Thionyl chloride-methanol solution is both reactant and solvent in this step, is led to
Product purity and yield can be improved by crossing secondary back.
Three mouthfuls of containers in reaction vessel and step 2) wherein in step 1) are all respectively provided with CaCl2Drying device and alkali
Liquid absorption plant, drying device ensure do not have moisture in container, can be decomposed because thionyl chloride meets water, release sulfur dioxide, chlorine
It is precautionary measures to change irritative gas, the alkali liquor absorptions such as hydrogen, because not ensuring that all medicines 100% do not have moisture, is added
If thionyl chloride has a small amount of decompose, alkali lye can absorb sour gas, and thionyl chloride can also use alkali if having leakage in itself
Liquid absorbs.
3) synthesis of the amide derivatives of methionine
Hydrochloride methyl methionine 4.00g stirs 3.5h after being mixed with n-octyl amine 7.24mL at 90 DEG C, by reaction product
After 100mL isopropanols, then KOH1.12g is added in the mixture, stir 3h at room temperature.After filtering, then it is evaporated under reduced pressure,
So that isopropanol and excessive n-octyl amine to be removed, add n-hexane to solid precipitation and produce.Isolate solid sediment, use just oneself
After alkane washing, the derivative of dry methionine amide, i.e. 2- amino -3- methyl mercaptos-N- octyl groups-butyramide in atmosphere.This
From n-octyl amine as reactant in step, main n-octyl amine is that 8 carbon atom lengths are suitable, and carbochain is too because n-octyl amine has
It is long, derivative it is water-soluble bad, carbochain is too short, and derivative corrosion inhibition rate is not high.
From fig. 1, it can be seen that 1673cm-1And 1586cm-1For the stretching vibration peak of acid amides C=O double bonds；3421cm-1For amino-
N-H stretching vibration peak；2967cm-1、2668cm-1And 2573cm-1For the stretching vibration peak of saturation-c h bond.Thus deducibility
Go out, products therefrom is really the amide derivatives of methionine.
In 30 DEG C of 0.5M H2SO4The carbon steel surface of the methionine amide derivative prepared by the present invention is added in solution
Langmuir adsorption isotherms are as shown in Figure 2.Adsorption free energyIllustrate that methionine amide derives
Thing carbon steel surface absorption based on chemisorbed.Adsorption free energy is that negative value illustrates that absorption of the corrosion inhibiter on carbon steel surface is
Spontaneously, effectively adsorb.
The principle of the present invention：A sulphur atom and two nitrogen-atoms in methionine derivative molecular, these hetero atoms can be with
The d track bondings of metal hollow, are effectively adsorbed in metal surface so as to play a protective role, in addition, methionine derivative is also
Hydrophobic effect is played in alkyl containing 8 carbon, the orientable metal surface that is arranged in, and hetero atom and long alkyl mutually cooperate with work
With the absorption in metal surface being strengthened, so as to improve corrosion inhibition rate.
The pickling specific implementation method of Novel egg threonine derivative corrosion inhibiter：
25~55 DEG C of pickling temperature, pickle are 0.5mol/L sulfuric acid or 1mol/L hydrochloric acid, are added in every liter of pickle
Density of corrosion inhibitor be 20~200mg/L, pickling time is 4~16 hours.Experiment material is A3 carbon steel coupons, and surface area is
20cm2。
Embodiment 1：
Pickle is 0.5mol/L sulfuric acid, and pickling temperature is 30 DEG C.2- amino -3- methyl mercaptos-N- is added into pickle
Octyl group-butyramide, it is small that carbon steel coupon for 50mg/L is immersed in pickle 8 by the density of corrosion inhibitor added in every liter of pickle
When, after experiment terminates, removing surface, cold wind drying are carried out after removing carbon steel coupon, and calculate corrosion inhibition rate.
Conclusion：It is 95% by calculating corrosion inhibition rate, shows that the corrosion inhibiter has preferable corrosion mitigating effect.
Embodiment 2：
Pickle is 0.5mol/L sulfuric acid, and pickling temperature is 30 DEG C.2- amino -3- methyl mercaptos-N- is added into pickle
Octyl group-butyramide, it is small that carbon steel coupon for 100mg/L is immersed in pickle 8 by the density of corrosion inhibitor added in every liter of pickle
When, after experiment terminates, removing surface, cold wind drying are carried out after removing carbon steel coupon, and calculate corrosion inhibition rate.
Conclusion：It is 98% by calculating corrosion inhibition rate, shows that the corrosion inhibiter has preferable corrosion mitigating effect.
Embodiment 3：
Pickle is 0.5mol/L sulfuric acid, and pickling temperature is 30 DEG C.2- amino -3- methyl mercaptos-N- is added into pickle
Octyl group-butyramide, it is small that carbon steel coupon for 200mg/L is immersed in pickle 8 by the density of corrosion inhibitor added in every liter of pickle
When, after experiment terminates, removing surface, cold wind drying are carried out after removing carbon steel coupon, and calculate corrosion inhibition rate.
Conclusion：It is 99% by calculating corrosion inhibition rate, shows that the corrosion inhibiter has preferable corrosion mitigating effect, be high-efficient corrosion inhibition type
Agent.
Compared with prior art, the beneficial effects of the invention are as follows：Prepared methionine derivative dosage is small, inhibition efficiency
High (inhibition efficiency is up to more than 99%), it is nontoxic to environment, meet green corrosion inhibitor demand for development, in wider pickling temperature
It is applicable in degree and pickling concentration.
Claims (4)
1. a kind of methionine derivative corrosion inhibiter for pickling iron and steel, the methionine derivative corrosion inhibiter it is entitled：2- ammonia
Base -3- methyl mercaptos-N- octyl groups-butyramide, chemical structural formula are：
。
2. the synthetic method of the methionine derivative corrosion inhibiter described in claim 1, synthetic route are：
3. synthetic method according to claim 2, it is divided into three steps：The preparation of thionyl chloride-methanol solution, methionine
The synthesis of methyl ester hydrochloride and the synthesis of the amide derivatives of methionine, it is specific as follows：
1) preparation of thionyl chloride-methanol solution
Methanol is added into reaction vessel, ice salt bath is cooled to less than -10 DEG C, stirs lower dropwise addition thionyl chloride, and speed is added dropwise in control
Degree makes reaction temperature be no more than 0 DEG C, be warmed to room temperature naturally after reacting 1h, obtain thionyl chloride-methanol solution, wherein thionyl chloride
Concentration is 1-2mol/L；
2) synthesis of hydrochloride methyl methionine
Reflux condensing tube, dropping funel and thermometer are installed on three mouthfuls of containers, methanol is added in three mouthfuls of containers, uses ice salt bath
Less than -10 DEG C are cooled to, thionyl chloride is slowly added dropwise under stirring, controls rate of addition to be no more than reaction temperature during dropwise addition
0 DEG C, continue to stir；Methionine is added, the mol ratio of wherein methionine and thionyl chloride is：1:1~1:1.5, it is heated to reflux,
The thionyl chloride with evaporation solvent methanol and excess is evaporated under reduced pressure, to doing, above-mentioned solid is used into obtained dichloro in step 1) again
Sulfoxide-methanol solution dissolving, reheats backflow, is evaporated under reduced pressure evaporation solvent, extremely dry, obtains hydrochloride methyl methionine solid；
3) synthesis of the amide derivatives of methionine
The hydrochloride methyl methionine that step 2) is obtained is with n-octyl amine by mol ratio：1:3~1:At 80-100 DEG C after 5 mixing
Lower stirring reaction, after reaction product isopropanol, add alkali lye and neutralized；After filtering, then it is evaporated under reduced pressure, will
Isopropanol and excessive n-octyl amine remove, and add n-hexane to solid precipitation and produce；Solid sediment is isolated, is washed with n-hexane
After washing, the derivative of dry methionine amide, i.e. 2- amino -3- methyl mercaptos-N- octyl groups-butyramide in atmosphere.
4. the application of the methionine derivative corrosion inhibiter described in claim 1, wherein described methionine derivative corrosion inhibiter exists
Addition concentration in pickle is 20-200mg/L.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108754510A (en) * | 2018-06-22 | 2018-11-06 | 重庆工业职业技术学院 | A kind of compound restrainer and preparation method thereof containing Schiff |
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|---|---|---|---|---|
| CN101358353A (en) * | 2008-09-11 | 2009-02-04 | 河北理工大学 | Aminoacids composite restrainer and method of use thereof |
| CN105622471A (en) * | 2016-01-27 | 2016-06-01 | 西南石油大学 | Preparation method of methionine derivative corrosion inhibitor |
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2017
- 2017-09-26 CN CN201710878406.3A patent/CN107459473B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101358353A (en) * | 2008-09-11 | 2009-02-04 | 河北理工大学 | Aminoacids composite restrainer and method of use thereof |
| CN105622471A (en) * | 2016-01-27 | 2016-06-01 | 西南石油大学 | Preparation method of methionine derivative corrosion inhibitor |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108754510A (en) * | 2018-06-22 | 2018-11-06 | 重庆工业职业技术学院 | A kind of compound restrainer and preparation method thereof containing Schiff |
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Effective date of registration: 20200813 Address after: Haishu District of Zhejiang city in Ningbo province 315171 Ji Shi Gang Zhen Feng Village Patentee after: NINGBO DECHENG TOOLS Co.,Ltd. Address before: 063000 No. 38 Hua Yan Road, North Tangshan City Road, Hebei Patentee before: TANGSHAN College |