CN103484091A - O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate and application thereof - Google Patents
O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate and application thereof Download PDFInfo
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- CN103484091A CN103484091A CN201310448545.4A CN201310448545A CN103484091A CN 103484091 A CN103484091 A CN 103484091A CN 201310448545 A CN201310448545 A CN 201310448545A CN 103484091 A CN103484091 A CN 103484091A
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- vanillin
- schiff
- polyethylene glycol
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- aminobenzoic acid
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- 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
- C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
- C08G2650/04—End-capping
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
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- 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
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Abstract
The invention discloses a surfactant, namely o-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate with the corrosion inhibition effect and application thereof. The structural formula of the o-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is shown in the specification. The o-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is applicable to prevent corrosion of carbon steel and carbon steel products in an oilfield water solution. The o-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate and the application have the advantages that the o-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is adsorbed on the surface of the carbon steel to form a membrane by means of the surface activity and the Schiff-base coordination function of the surfactant, and higher corrosion inhibition performance is obtained.
Description
Technical field
The invention belongs to the inhibiter technical field, particularly a kind of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester that prevents that carbon steel and goods thereof from corroding in oil-field water solution.
Background technology
Metallic substance all is widely used in every field, the corrosion meeting of metallic substance brings about great losses to the economy of national society, according to relevant report, point out, the financial loss that industrially developed country is caused by metallic corrosion every year accounts for the 2%-4% of gross national product then.Therefore, research and development corrosion of metal means of defence is to promoting socio-economic development significant.The application of tensio-active agent in the corrosion inhibition for metal field is one of its topmost application.Tensio-active agent with corrosion inhibition can form adsorption film in metallic surface, and hydrophilic radical is adsorbed on metallic surface, and physics or chemisorption occur, and forms coating effect how much, thereby metal is played to corrosion inhibition.In recent years, the development and application of Surfactant is the focus of region of chemistry and inhibition circle always, also constantly emerge some novel tensio-active agent kinds, as Gemini surface active agent (Gemini Surfactant), Ionic Liquid as Surface Active Agent, Oligomeric Surfactants and New Schiff Base class tensio-active agent etc., these tensio-active agents have the surface-active while, and corrosion inhibition for metal has also been made to huge contribution.Take a broad view of forefathers' achievement in research, great majority are to utilize merely the amphiphilic structure of tensio-active agent to reach the inhibition purpose.Because the Schiff bases compound contains imine group (C=N-); some aromatic Schiff's base are except the two keys of contain-C=N-; on some phenyl ring, also have-the OH group; and the organic inhibition agent molecule contains heteroatoms and the π-electron conjugated systems such as N, S, O or P; easy and metal forms coordinate bond; thereby can be adsorbed on metallic surface, form the inhibition protection film.Therefore, if can in surfactant molecule, introduce the Containing Schiff-bases structure, the range of application of tensio-active agent just is expected to be enlarged, corrosion inhibition also is expected to be improved.Based on above thinking, the present invention is by schiff base structure and the condensation of polyoxyethylene glycol lauric acid monoester long-chain, synthesize o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester tensio-active agent, and probed into this novel surfactant corrosion inhibition to carbon steel in the simulated oil water in field.
Summary of the invention
The purpose of this invention is to provide a kind of tensio-active agent o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester and application thereof with corrosion inhibition.
The structural formula of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester is:
。
Described o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester is applied to prevent that carbon steel and goods thereof from corroding in oil-field water solution.
Advantage of the present invention is to live and Schiff's base coordination function by the superficiality of tensio-active agent, makes o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester in the easy absorption film-forming of steel surface, has higher corrosion inhibition.
Embodiment
embodiment:
(1) structural formula of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester:
(2) preparation method of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester is:
A. prepare o-vanillin contracting para-amino benzoic acid Schiff's base
Take 1.5214 grams (0.01 mole) o-vanillin and be placed in 100 milliliters of there-necked flasks, with 30 milliliters of dehydrated alcohol ultrasonic dissolutions, take para-amino benzoic acid 1.3714 grams (0.01 mole) of equimolar amount in beaker, with 40 milliliters of dehydrated alcohol ultrasonic dissolutions, after above-mentioned two kinds of solution mix under 65 ℃ of waters bath with thermostatic control, magnetic agitation refluxes 2 hours, product takes out standing 7 hours, after all separating out, precipitation filters, leach thing absolute ethanol washing 2 times, put into 40 ℃ of vacuum drying ovens dry 24 hours, obtain orange/yellow solid and be o-vanillin contracting para-amino benzoic acid Schiff's base.
B. prepare the polyoxyethylene glycol lauric acid monoester
Take 12 grams (0.03 mole) polyoxyethylene glycol (400) and 0.6183 gram (0.01 mole) boric acid and be placed in the there-necked flask of 100 milliliters, this reaction system is the vacuum decompression state, under the low pressure of 0.1MPa, oil bath is heated to 120 ℃, sustained reaction 2 hours, after being cooled to room temperature, add respectively again 6.0096 grams (0.03 mole) lauric acid and 0.226 gram p-methyl benzenesulfonic acid, continuation oil bath under the low pressure of 0.1MPa is heated to 120 ℃, sustained reaction 3 hours, be cooled to room temperature, then add in 0.7 gram sodium acetate and system in p-methyl benzenesulfonic acid, add again 5 ml distilled waters, 95 ℃ of stirred in water bath, selective hydrolysis 1 hour, then add isopyknic saturated aqueous common salt, make paratoluenesulfonic acid sodium salt, the Sodium Tetraborate generated after the sodium acetate that unreacted is complete and hydrolysis is dissolved in saturated aqueous common salt, after cooling, isolate the product that solidify on upper strata, by the slow circumvolve evaporation in Rotary Evaporators of isolated product, remove moisture, obtain light yellow oily liquid and be the polyoxyethylene glycol lauric acid monoester.
C. prepare o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester
Be dissolved in 20 milliliters of N together with taking o-vanillin contracting para-amino benzoic acid Schiff's base that 2 mmole a steps make and 2 mmole b walking the polyoxyethylene glycol lauric acid monoester made, in the dinethylformamide solvent, after mixing, add 0.0196 gram tosic acid as catalyzer, oil bath is heated to 130 ℃, sustained reaction 3 hours, cooling after, steaming desolventizes, and obtains the burgundy oily liquids and is o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester.
(3) application of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester:
A. prepare the carbon steel test piece: prepare the carbon steel coupon that 16 specifications are 50 millimeters * 10 millimeters * 2 millimeters, use respectively 240#, the silicon carbide paper of 600# and 1500# is extremely smooth smooth by the carbon steel coupon polishing, putting into the beaker that fills acetone soaks 5 minutes, with absorbent cotton, dry, put into again the dehydrated alcohol immersion and within 5 minutes, carry out further degreasing, after taking out test piece, with blower, dry up, in loft drier, drying is 5 hours, use analytical balance accurate weighing to 0.0001 gram after taking out, and record data, seal no cross section with solid paraffin, stay the working face of 1 * 1 square centimeter standby.
B. prepare the simulated oil water in field: take respectively medicine adding distil water by table 1 formula and be stirred to fully and dissolve, move in 1 liter of volumetric flask and carry out constant volume, logical nitrogen deoxygenation in 15 minutes, more logical carbonic acid gas obtains the simulated oil water in field to saturated.
Table 1 simulated oil water in field formula
C. weight-loss method is measured corrosion inhibition: get each 20 milliliters, simulated oil water in field that the b step prepares and be contained in the beaker of 50 milliliters that 6 size specifications are identical, wherein one group is the blank group, other 5 groups of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoesters that add respectively different mass, make the concentration of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester in the simulated oil water in field be respectively 20 mg/litre, 50 mg/litre, 100 mg/litre, 150 mg/litre, 200 mg/litre, the carbon steel coupon mark of respectively a step being handled well is again put into well 6 beakers, the zero-G test cycle is 72 hours, in experimentation, beaker needs sealing, take out carbon steel coupon after 72 hours and remove surperficial solid paraffin, after distilled water flushing, wipe gently surperficial corrosion product with absorbent cotton, put into the sherwood oil degreasing degreasing, use again dehydrated alcohol ultrasonic cleaning further degreasing in 5 minutes after cleaning with absorbent cotton, put into loft drier after finally drying with filter paper dry 4 hours, finally use analytical balance accurate weighing to 0.0001 gram, record weightless data, experiment repeats twice, averages.
Erosion rate V calculates by formula (1), and inhibition efficiency IE calculates by formula (2):
V=(W
0－W
t)/(S×t) （1）
In formula, V is erosion rate, gm
-2h
-1; W
0and W
tbe respectively the quality after front and corrosion are corroded in the carbon steel test piece, g; The working area that S is test piece, m
2; T is the corrosion experiment time, h.
IE= [ (V
0 –V
t) / V
0 ] × 100% （2）
In formula, IE is inhibition efficiency, %; V
0for erosion rate under blank condition, gm
-2h
-1; V
tfor adding the erosion rate under the inhibiter condition.
Table 2 weightless test data
From table 2 weightless test data, after adding o-vanillin contracting contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester, weightlessness obviously reduces, illustrate that o-vanillin contracting contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester has better corrosion inhibition, when concentration is 20 mg/litre, corrosion inhibition rate just reaches more than 65%, when concentration is 50 mg/litre, corrosion inhibition rate just reaches more than 80%, along with concentration continues to raise, when concentration is 100 mg/litre, corrosion inhibition rate just reaches more than 82%, along with concentration continues to raise, the variation of corrosion inhibition rate is little, show when the concentration of 100 mg/litre, the inhibition molecule has been adsorbed on metallic surface preferably, form dense protective membrane.
Claims (2)
1. the tensio-active agent o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester with corrosion inhibition is characterized in that the structural formula of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester is:
2. the application of o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester according to claim 1, is characterized in that described o-vanillin contracting para-amino benzoic acid Containing Schiff-bases polyoxyethylene glycol lauric acid monoester is applied to prevent that carbon steel and goods thereof from corroding in oil-field water solution.
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|---|---|---|---|
| CN201310448545.4A CN103484091B (en) | 2013-09-27 | 2013-09-27 | O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate and application thereof |
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| CN201310448545.4A CN103484091B (en) | 2013-09-27 | 2013-09-27 | O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate and application thereof |
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| CN103484091A true CN103484091A (en) | 2014-01-01 |
| CN103484091B CN103484091B (en) | 2015-12-23 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101988202A (en) * | 2009-08-07 | 2011-03-23 | 中国科学院海洋研究所 | Carboxymethyl chitosan oligosaccharide schiff base organic carbon steel seawater corrosion inhibitor and application thereof |
| CN101805906B (en) * | 2010-04-15 | 2011-09-07 | 桂林理工大学 | Composite corrosion inhibitor for restraining corrosion of carbon steel in seawater and preparation method thereof |
| CN102311863A (en) * | 2010-07-09 | 2012-01-11 | 气体产品与化学公司 | Method for wafer dicing and composition useful thereof |
| CN103265454A (en) * | 2013-06-11 | 2013-08-28 | 桂林理工大学 | In situ synthesis method of o-vanillin shrinkage hydrazine hydrate bis-Schiff base |
-
2013
- 2013-09-27 CN CN201310448545.4A patent/CN103484091B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101988202A (en) * | 2009-08-07 | 2011-03-23 | 中国科学院海洋研究所 | Carboxymethyl chitosan oligosaccharide schiff base organic carbon steel seawater corrosion inhibitor and application thereof |
| CN101805906B (en) * | 2010-04-15 | 2011-09-07 | 桂林理工大学 | Composite corrosion inhibitor for restraining corrosion of carbon steel in seawater and preparation method thereof |
| CN102311863A (en) * | 2010-07-09 | 2012-01-11 | 气体产品与化学公司 | Method for wafer dicing and composition useful thereof |
| CN103265454A (en) * | 2013-06-11 | 2013-08-28 | 桂林理工大学 | In situ synthesis method of o-vanillin shrinkage hydrazine hydrate bis-Schiff base |
Non-Patent Citations (1)
| Title |
|---|
| NABEL A. NEGM ET AL: "Corrosion inhibition efficiency", 《COLLOIDS AND SURFACES A: PHYSICOCHEM. ENG. ASPECTS》 * |
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