CN103484091B - 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 PDF

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Publication number
CN103484091B
CN103484091B CN201310448545.4A CN201310448545A CN103484091B CN 103484091 B CN103484091 B CN 103484091B CN 201310448545 A CN201310448545 A CN 201310448545A CN 103484091 B CN103484091 B CN 103484091B
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vanillin
polyethylene glycol
glycol monolaurate
aminobenzoic acid
base polyethylene
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CN103484091A (en
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刘峥
刘进
张菁
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Guilin University of Technology
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Guilin University of Technology
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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
    • 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
    • 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
    • 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)
    • 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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  • Life Sciences & Earth Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of tensio-active agent o-vanillin contracting acid Schiff-base polyethylene glycol monolaurate and the application thereof with corrosion inhibition, the structural formula of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is:

Description

O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate and application thereof
Technical field
The invention belongs to inhibiter technical field, particularly a kind of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate preventing carbon steel and goods thereof from corroding in oil-field water solution.
Background technology
Metallic substance is all widely used in every field, the corrosion of metallic substance can bring about great losses to the economy of national society, point out according to relevant report, 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, corrosion of metal means of defence is researched and developed significant to promotion socio-economic development.Tensio-active agent is one of its topmost application in the application in corrosion inhibition for metal field.The 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 geometry coating effect, thus plays corrosion inhibition to metal.In recent years, the development and application of Surfactant is the focus of region of chemistry and inhibition circle always, also the tensio-active agent kind that some are novel is constantly emerged, as Gemini surface active agent (GeminiSurfactant), Ionic Liquid as Surface Active Agent, Oligomeric Surfactants and New Schiff Base class tensio-active agent etc., these tensio-active agents, having surface-active while, have also made tremendous contribution to corrosion inhibition for metal.Take a broad view of the achievement in research of forefathers, great majority utilize merely the amphiphilic structure of tensio-active agent to reach inhibition object.Because Schiff bases compound contains imine group (-C=N-); some aromatic Schiff's base are except containing-C=N-double bond; some phenyl ring also has-OH group; and organic inhibition agent molecule contains the heteroatomss such as N, S, O or P and π-electron-conjugated system; easy and metal forms coordinate bond; thus can metallic surface be adsorbed on, form inhibition protection film.Therefore, if can introduce Containing Schiff-bases structure in surfactant molecule, the range of application of tensio-active agent is just expected to obtain expansion, corrosion inhibition is also 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 p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate tensio-active agent, and probe into this novel surfactant in simulated oil water in field to the corrosion inhibition of carbon steel.
Summary of the invention
The object of this invention is to provide a kind of tensio-active agent o-vanillin contracting acid Schiff-base polyethylene glycol monolaurate and the application thereof with corrosion inhibition.
The structural formula of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is:
。
Described O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is applied to and prevents carbon steel and goods thereof from corroding in oil-field water solution.
Advantage of the present invention is lived and Schiff's base coordination function by the superficiality of tensio-active agent, makes O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate in the easy absorption film-forming of steel surface, have higher corrosion inhibition.
Embodiment
embodiment:
(1) structural formula of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate:
。
(2) preparation method of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is:
A. O-vanillin p-aminobenzoic para-amino benzoic acid Schiff's base is prepared
Take 1.5214 grams of (0.01 mole) o-vanillins and be placed in 100 milliliters of there-necked flasks, with 30 milliliters of dehydrated alcohol ultrasonic dissolutions, take the 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 DEG C of waters bath with thermostatic control, magnetic agitation refluxes 2 hours, product takes out and leaves standstill 7 hours, filter after whole precipitation to be precipitated, much filtrate absolute ethanol washing 2 times, put into 40 DEG C of vacuum drying ovens dry 24 hours, obtain orange/yellow solid and be O-vanillin p-aminobenzoic para-amino benzoic acid Schiff's base.
B. polyoxyethylene glycol lauric acid monoester is prepared
Take the there-necked flask that 12 grams of (0.03 mole) polyoxyethylene glycol (400) and 0.6183 gram of (0.01 mole) boric acid are placed in 100 milliliters, this reaction system is vacuum decompression state, under the low pressure of 0.1MPa, oil bath is heated to 120 DEG C, sustained reaction 2 hours, after being cooled to room temperature, add 6.0096 grams of (0.03 mole) lauric acid and 0.226 gram of p-methyl benzenesulfonic acid more respectively, continue oil bath under the low pressure of 0.1MPa and be heated to 120 DEG C, sustained reaction 3 hours, be cooled to room temperature, then to add in 0.7 gram of sodium acetate and p-methyl benzenesulfonic acid in system, add 5 ml distilled waters again, 95 DEG C of stirred in water bath, selective hydrolysis 1 hour, then isopyknic saturated aqueous common salt is added, make paratoluenesulfonic acid sodium salt, the sodium acetate that unreacted is complete and the rear Sodium Tetraborate generated of hydrolysis are dissolved in saturated aqueous common salt, after cooling, isolate the product that upper strata is solidified, by the slow circumvolve evaporation in Rotary Evaporators of isolated product, removing moisture, obtain pale yellowish oil liquid and be polyoxyethylene glycol lauric acid monoester.
C. O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is prepared
Take 2 mmole a to walk obtained O-vanillin p-aminobenzoic para-amino benzoic acid Schiff's base and walk together with obtained polyoxyethylene glycol lauric acid monoester with 2 mmole b and be dissolved in 20 milliliters of N, in dinethylformamide solvent, after mixing, add 0.0196 gram of tosic acid as catalyzer, oil bath is heated to 130 DEG C, and sustained reaction 3 hours, after cooling, steaming desolventizes, and obtains burgundy oily liquids and is O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate.
(3) application of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate:
A. carbon steel test piece is prepared: prepare the carbon steel coupon that 16 specifications are 50 millimeters × 10 millimeters × 2 millimeters, use 240# respectively, carbon steel coupon is polished to flat smooth by the silicon carbide paper of 600# and 1500#, put into the beaker filling acetone to soak 5 minutes, dry with absorbent cotton, put into dehydrated alcohol immersion again and carry out further degreasing in 5 minutes, dry up with blower after taking out test piece, drying 5 hours in loft drier, with analytical balance accurate weighing to 0.0001 gram after taking out, and record data, no cross section is sealed with solid paraffin, stay the working face of 1 × 1 square centimeter for subsequent use.
B. simulated oil water in field is prepared: filling a prescription by table 1 takes medicine and adding distil water is stirred to and dissolves completely respectively, moves in 1 liter of volumetric flask and carry out constant volume, logical nitrogen deoxygenation in 15 minutes, more logical carbonic acid gas is to saturated, be i.e. acquisition simulated oil water in field.
Table 1 simulated oil water in field is filled a prescription
C. weight-loss method measures corrosion inhibition: get b and walk each 20 milliliters of the simulated oil water in field prepared and be contained in the identical beaker of 50 milliliters of 6 size specifications, wherein one group is blank group, other 5 groups of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate adding different mass respectively, the concentration of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate in simulated oil water in field is made to be respectively 20 mg/litre, 50 mg/litre, 100 mg/litre, 150 mg/litre, 200 mg/litre, respectively a is walked the carbon steel coupon handled well again to mark and put into 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 surface solid paraffin, after distilled water flushing, the corrosion product on surface is wiped gently with absorbent cotton, put into sherwood oil degreasing degreasing, after cleaning with absorbent cotton, use dehydrated alcohol ultrasonic cleaning further degreasing in 5 minutes again, put into loft drier after finally drying with filter paper dry 4 hours, finally use analytical balance accurate weighing to 0.0001 gram, record Weight loss data, experiment repetition 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 tquality before being respectively carbon steel test piece corrosion and after corrosion, g; S is the working area of 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 inhibiter condition.
Table 2 weightless test data
From table 2 weightless test data, weightless obviously minimizing after adding O-vanillin p-aminobenzoic contracting acid Schiff-base polyethylene glycol monolaurate, illustrate that O-vanillin p-aminobenzoic contracting acid Schiff-base polyethylene glycol monolaurate 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 change of corrosion inhibition rate is little, show when the concentration of 100 mg/litre, inhibition molecule is adsorbed on metallic surface preferably, form dense protective membrane.

Claims (2)

1. an O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate, is characterized in that the structural formula of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is:
；
Wherein repeating unit [CH 2cH 2o] nbe consistent with the repeating unit in poly(oxyethylene glycol) 400.
2. the application of O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate according to claim 1, is characterized in that described O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate is applied to and prevents carbon steel and goods thereof from corroding in oil-field water solution.
CN201310448545.4A 2013-09-27 2013-09-27 O-vanillin p-aminobenzoic acid Schiff-base polyethylene glycol monolaurate and application thereof Expired - Fee Related CN103484091B (en)

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