CN104277816B - One class sulfonate amphoteric high molecular surfactant and its synthetic method - Google Patents

One class sulfonate amphoteric high molecular surfactant and its synthetic method Download PDF

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CN104277816B
CN104277816B CN201410525875.3A CN201410525875A CN104277816B CN 104277816 B CN104277816 B CN 104277816B CN 201410525875 A CN201410525875 A CN 201410525875A CN 104277816 B CN104277816 B CN 104277816B
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surfactant
high molecular
synthetic method
molecular surfactant
sulfonate
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CN104277816A (en
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叶仲斌
张轩
陈洪
韩利娟
蒋金芳
宋佳蓉
冯思思
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Southwest Petroleum University
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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
    • C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
    • C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses a class sulfonate amphoteric high molecular surfactant and its synthetic method, the high molecular surfactant prepares as follows：（1）1mol long chain alkyl dimethyl allylic bromination ammoniums, 1.2 ~ 20mol acrylonitrile are mixed, temperature control to 0oC, is added dropwise 1.2 ~ 20mol oleums, stirs 0.5 2h, is warming up to 20 50oC, both sexes sulfonate type surfactant is obtained after 12 48h of reaction；（2）By both sexes sulfonate type surfactant and the methyl propane sulfonic acid of 2 acrylamide 2 according to mol ratio 0.1~3：7~9.9 is soluble in water, and regulation pH value is 7, adds initiator, is warming up to 30 ~ 60 oC, react 3 ~ 10h.The high molecular surfactant can be viscosified in the saline solution of certain salinity scope, and with good surface-active and emulsifiability, its synthetic method mild condition, high income, it is easy to purification ＆ isolation.

Description

One class sulfonate amphoteric high molecular surfactant and its synthetic method
Technical field
The present invention relates to a class sulfonate amphoteric high molecular surfactant and its synthetic method.
Background technology
Exhaustion with people to petroleum resources in the sharp increase of energy demand and world wide, people will increasingly Many concerns focus on the crude oil how effectively exploited and remain in old filed block underground, and have developed many raising crude oil and adopt The new method of yield (EOR), such as thermal recovery, gas drive, mixed phase drive, microorganism drive, chemical flooding.Wherein, due to chemical flooding low cost, It is applied widely, oil recovery factor can be effectively improved and by wide popularization and application, and achieve breakthrough progress.
Chemical flooding improves recovery ratio measure and is broadly divided into three kinds：Polymer flooding, polymer-surfactant drives (SP), with And alkali-polymer-surfactant ternary composite driving drives (ASP).But these three measures all be present.In polymer flooding In, oil displacement system is mainly viscosified by adding water-soluble polymer to working solution, so as to improve injection fluid and in-place oil Mobility ratio, and improve the sweep efficiency of oil displacement system.But this kind of usual interfacial activity of working solution is low, it is impossible to effectively change rock Surface wettability, and substantially to crude oil without increase-volume and emulsifying capacity, therefore its application is limited.SP drives and ASP drives can be effective Improve the interfacial activity of working solution, can significantly reduce oil water interfacial tension, and can effectively emulsify with toughness reinforcing crude oil, but it significantly lacks Point is that, because surfactant and interpolymer interaction cause system viscosity low, and working solution is relatively costly.Further, since table Characterization of adsorption and the diffusivity difference of face activating agent and water soluble polymer are very big, in the porous media migration process of stratum, SP drives and ASP drives working solution and chromatographic fractionation effect easily occurs, so as to weaken working solution ability significantly, even results in its failure. In addition, ASP drive in due to the introducing of alkali, the problems such as extremely serious injury can be produced to pipeline and stratum.In view of the above problems, Develop new oil displacing material to make up the defect of current oil displacement system, as the task of top priority.
The present invention has synthesized a family macromolecule surfactant, and the high molecular surfactant was both poly- with classic water-soluble The feature of compound, can viscosify in aqueous, and with good surface-active, can effectively reduce oil water interfacial tension, emulsification Crude oil and hydro carbons.Due to its unique performance, as a kind of new oil displacement agent, there is important answering to improving oil recovery factor With value.
The content of the invention
It is an object of the invention to provide a class sulfonate amphoteric high molecular surfactant, the polymer is mainly applied In oil exploitation, drilling completion industry, both with the feature of classic water-soluble polymer, can be in the salt solution of certain salinity scope Viscosified in solution, and with good surface-active and emulsifiability, can effectively emulsified crude oil and hydro carbons, due to its unique property Can, there is important application value to improving oil recovery factor.
Another object of the present invention also resides in the synthetic method for providing above-mentioned sulfonate amphoteric high molecular surfactant, The method principle reliability, easy to operate, mild condition, high income, and it is easy to purification ＆ isolation, with wide market prospects.
To reach above technical purpose, the present invention provides following technical scheme.
One class sulfonate amphoteric high molecular surfactant, there is 2- acrylamide-2-methyl propane sulfonics (AMPS) and two Property sulfonate surfactant (AMCnDMAPS) two kinds of construction units, its structural formula is as follows：
Wherein x, y are construction unit number, and x is that 70~99%, y is 1~30%.
The synthetic method of one class sulfonate amphoteric high molecular surfactant, comprises the following steps successively：
(1) by 1mol long chain alkyl dimethyl allylic bromination ammoniums (CnDMAAB, n=12~22), 1.2~20mol propylene Nitrile is stirred in being added to there-necked flask, is controlled to 0 DEG C temperature of reaction system with ice salt bath, is dripped by constant pressure funnel Plus 1.2~20mol oleums, stir 0.5-2h, then heat to 20-50 DEG C, after isothermal reaction 12-48h, be filtered to remove The acrylonitrile of amount, obtains light yellow crystal, with acetone recrystallization, obtains clear crystal, i.e. both sexes sulfonate type surfactant (AMCnDMAPS, n=12~22)；
(2) by both sexes sulfonate type surfactant (AMCnDMAPS, n=12~22) and 2- acrylamide -2- methyl-props Sulfonic acid (AMPS) is soluble in water, and the mol ratio of both sexes sulfonate type surfactant and 2- acrylamide-2-methyl propane sulfonics is 0.1~3：7~9.9, it is 7 or so to adjust pH value with sodium bicarbonate solution, and total monomer is 10~30 mass %, is passed through nitrogen 30min carries out deoxygenation, adds the isobutyl imidazoline hydrochloride (AIBI) of initiator azo two, and initiator dosage is monomer gross mass 0.05~1.5%, system is warming up to 30~60 DEG C, after 3~10h of reaction, with ethanol and the repeated multiple times washing of precipitate of acetone, will Product dries 48h in 40 DEG C of vacuum drying ovens, after crushing granulation, obtains final product sulfonate amphoteric high molecular surfactant AMPS/ AMCnDMAPS (n=12~22).
In the present invention, it is solvent acrylonitrile to be used first, under the conditions of ice salt bath, long chain alkyl dimethyl allyl bromide, bromoallylene Change ammonium and obtain both sexes sulfonate type surfactant monomer (AMC with oleum and acrylonitrile reactornDMAPS, n=12~ 22).Then nothing is obtained using free yl solution polymerization method and returns micro- block copolymer.Its reaction equation is as follows：
Compared with prior art, the invention has the advantages that：
1. the sulfonate amphoteric high molecular surfactant that the present invention synthesizes, its synthesis material is simple and easy to get, its synthesis Method is convenient succinct.
2. the family macromolecule surfactant has good surface-active, can effectively reduce oil water interfacial tension, emulsification Performance is good, can effectively emulsify organic solvent and crude oil, improves oil recovery factor.
Brief description of the drawings
Fig. 1 is sulfonate amphoteric high molecular surfactant AMPS/AMC18DMAPS's1HNMR spectrograms
Fig. 2 is sulfonate amphoteric high molecular surfactant AMPS/AMC18DMAPS solution viscosities are acted on NaCl concentration Relation curve
Fig. 3 is sulfonate amphoteric high molecular surfactant AMPS/AMC18DMAPS is to oil water interfacial tension influence curve
Specific embodiment
The present invention is further illustrated below according to drawings and Examples.
First, sulfonate amphoteric high molecular surfactant AMPS/AMC18The preparation of DMAPS
Embodiment 1
Octadecyldimethyl allylic bromination ammonium 209.3g, acrylonitrile 265.3g are stirred in being added to there-necked flask Mix, controlled to 0 DEG C temperature of reaction system with ice salt bath, 1.2~20mol oleums are then added dropwise by constant pressure funnel Acid, stirs 0.5h, then heats to 40 DEG C, isothermal reaction 36h.After reaction terminates, then cooling reaction system was filtered to remove The acrylonitrile of amount, obtains crude product light yellow crystal.Crude product is recrystallized with acetone, clear crystal, i.e. both sexes is obtained Sulfonate surfactant monomer (AMC18DMAPS)。
By 7.40gAMC18DMAPS, 51.8gAMPS are soluble in water, and it is 7 or so to adjust pH value with sodium bicarbonate solution, single Body total concentration is 20 mass %, and being passed through nitrogen 30min carries out deoxygenation, adds the isobutyl imidazoline hydrochloric acid of 0.5g initiators azo two Salt, system is warming up to 50 DEG C, and reaction is terminated after reaction 5h, with ethanol and the repeated multiple times washing of precipitate of acetone after, in 40 DEG C of vacuum Dry 48h in baking oven, after crushing granulation, obtain to white powder as sulfonate amphoteric high molecular surfactant AMPS/AMC18DMAPS。
2nd, sulfonate amphoteric high molecular surfactant AMPS/AMC18The structural characterization of DMAPS
Fig. 1 is AMPS/AMC prepared by embodiment 118DMAPS's1HNMR spectrograms, by polymer AMPS/ AMC18After the integral area ratio of the feature H of DMAPS is compared calculating, AMPS and AMC in polymer is found18The ratio of DMAPS Example is basically identical with the input ratio of monomer, shows polymer AMPS/AMC18DMAPS successfully synthesizes.Between 5~7ppm, not There is the characteristic displacement value of alkene hydrogen, therefore do not have monomer residue in showing polymer.
3rd, sulfonate amphoteric high molecular surfactant AMPS/AMC18The anti-salt property test of DMAPS
Fig. 2 is NaCl concentration to AMPS/AMC18DMAPS viscosity influence curves.It can be seen that polymer AMPS/ AMC18DMAPS solution viscosities are raised with the increase of brine strength.When NaCl concentration is 2000mg/L, solution viscosity reaches Maximum, system viscosity is 161.2mPa.s.Continue to increase NaCl concentration, polymer solution viscosity viscosity starts to reduce, and works as NaCl When concentration is 10000mg/L, system viscosity is 10.43mPa.s.Test shows polymer AMPS/AMC18DMAPS has good Anti-salt property.
4th, sulfonate amphoteric high molecular surfactant AMPS/AMC18The oil water interfacial tension test of DMAPS
Fig. 3 is AMPS/AMC prepared by embodiment 118DMAPS is to oil water interfacial tension influence curve.Can from figure Go out, oil water interfacial tension is with polymer AMPS/AMC18The increase of DMAPS solution concentrations and reduce.Work as polymer solution concentration During for 1000mg/L, oil water interfacial tension is 5.73mN m-1.Continue to increase polymer AMPS/AMC18DMAPS solution concentrations, oil Water interfacial tension change is little.Test shows polymer AMPS/AMC18DMAPS solution has good surface-active, can be effective Reduce oil water interfacial tension.
5th, sulfonate amphoteric high molecular surfactant AMPS/AMC18The emulsifying effectiveness test of DMAPS
The concentration that will have been configured is the polymer solution of 5000mg/L, according to oil-water ratio 1：1 ratio be added to crude oil and In kerosene, after stirring, scale test tube is poured into, after standing 12h, record its water yield, calculate its emulsification rate, be shown in Table 1.
The emulsifiability test result of table 1
From table 1 it follows that sulfonate amphoteric high molecular surfactant AMPS/AMC18The emulsification rate of DMAPS is 100%, and the emulsification rate of HPAM is only 27%.With HPAM solutions ratio, polymer AMPS/AMC is added18After DMAPS solution Sample, emulsifying effectiveness substantially, has good dispersive property and emulsifiability to kerosene and crude oil.Additionally, its emulsion static Still there is not lamination after week and its stability of emulsion significantly rises, it is very high steady that this shows that formed emulsion has It is qualitative.And not adding the solution of polymer of the present invention not occur emulsion, there is layering quickly after stopping in stirring.

Claims (1)

1. the synthetic method of a class sulfonate amphoteric high molecular surfactant, the surfactant has 2- acrylamides -2- Two kinds of construction units of methyl propane sulfonic acid and both sexes sulfonate type surfactant, its structural formula is as follows：
Wherein x, y are construction unit number, and x is that 70~99%, y is 1~30%,
Its synthetic method, comprises the following steps successively：
(1) by the long chain alkyl dimethyl allylic bromination ammonium that 1mol carbon numbers are 12~22,1.2~20mol acrylonitrile is added to It is stirred in there-necked flask, by temperature of reaction system control to 0 DEG C, 1.2~20mol oleums is added dropwise, stirs 0.5-2h, 20-50 DEG C, after isothermal reaction 12-48h is warming up to, excessive acrylonitrile is filtered to remove, light yellow crystal is obtained, is tied again with acetone Crystalline substance, obtains both sexes sulfonate type surfactant；
(2) by both sexes sulfonate type surfactant and 2- acrylamide-2-methyl propane sulfonics according to mol ratio 0.1~3：7~ 9.9 is soluble in water, and regulation pH value is 7 or so, and total monomer is 10~30 mass %, and being passed through nitrogen 30min carries out deoxygenation, then The isobutyl imidazoline hydrochloride of initiator azo two is added, initiator dosage is the 0.05~1.5% of monomer gross mass, and system heats up To 30~60 DEG C, after 3~10h of reaction, washed with ethanol and acetone repeated precipitation, product is dried in 40 DEG C of vacuum drying ovens 48h, after crushing granulation, obtains final product sulfonate amphoteric high molecular surfactant.
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CN105040425B (en) * 2015-07-01 2018-03-02 广东灵捷制造化工有限公司 A kind of mercerising bleeding agent and preparation method thereof
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CN102660247A (en) * 2012-05-07 2012-09-12 西南石油大学 Amphoteric ionic polymer clay stabilizer and preparation method
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US4959432A (en) * 1986-05-19 1990-09-25 Union Carbide Chemicals And Plastics Company Inc. Acid viscosifier compositions
CN1268961A (en) * 1996-11-15 2000-10-04 贝茨迪尔博恩公司 Aqueous dispersion polymers
CN1285852A (en) * 1997-03-31 2001-02-28 卡尔冈公司 Ampholyte polymers for use in personal care products
JP2001181353A (en) * 1999-12-27 2001-07-03 Lion Corp Use of amphoteric and amphiphilic copolymer as surface treating agent and surface treating agent composition comprising copolymer
CN1543484A (en) * 2001-06-11 2004-11-03 ��ï��ʽ���� Amphoteric water-soluble polymer dispersion and use thereof
CN1662609A (en) * 2002-06-21 2005-08-31 海茂株式会社 Water-soluble polymer dispersion, process for producing the same and method of use therefor
CN1756780A (en) * 2002-12-30 2006-04-05 巴斯福股份公司 Ampholytic copolymer and use thereof
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CN102432747A (en) * 2010-09-29 2012-05-02 中国石油化工股份有限公司 Amine lactone type amphoteric high polymer emulsion as well as preparation method and application thereof
CN102585092A (en) * 2012-01-16 2012-07-18 西南石油大学 Betaine type salt-resistant polymer and preparation method thereof
CN102617792A (en) * 2012-04-01 2012-08-01 中国科学院长春应用化学研究所 Hydrophobic association polyampholyte and preparation method thereof
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