CN111518534B - Nano surfactant and preparation method thereof - Google Patents

Nano surfactant and preparation method thereof Download PDF

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CN111518534B
CN111518534B CN202010387859.8A CN202010387859A CN111518534B CN 111518534 B CN111518534 B CN 111518534B CN 202010387859 A CN202010387859 A CN 202010387859A CN 111518534 B CN111518534 B CN 111518534B
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CN111518534A (en
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刘艳华
史建民
王耀国
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Ningbo Fengcheng Nanotechnology Co ltd
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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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/265—Citric acid
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    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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    • 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
    • C09K2208/10—Nanoparticle-containing well treatment fluids

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  • Oil, Petroleum & Natural Gas (AREA)
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  • Crystallography & Structural Chemistry (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

The application discloses a nano surfactant and a preparation method thereof, wherein the nano surfactant is prepared by reacting fatty amine with a compound A; the compound A is a micromolecular organic matter or an oligomer; the molecular weight of the micromolecular organic matter and the oligomer is 50-6000. The nano surfactant is synthesized from bottom to top by adopting a one-step method, not only has nanoscale, but also has interfacial activity, simplifies the reaction process and reduces the cost.

Description

Nano surfactant and preparation method thereof
Technical Field
The application relates to a nano surfactant and a preparation method thereof, belonging to the field of chemistry.
Background
A surfactant is a substance that causes a significant change in the interfacial state of a solution system. Has fixed hydrophilic and lipophilic groups and can be directionally arranged on the surface of the solution. The nanometer material has unique electric, magnetic, optical, electric, thermal and other performances due to small size effect, surface effect and quantum effect. The nanometer surfactant integrates the advantages of the two components into a whole, the nanometer surfactant with large particle size plays a role in water shutoff and profile control, and the nanometer surfactant with small particle size continuously migrates to play a role in oil washing. If the nano surfactant flooding technology is applied to the oilfield chemical technology, the oilfield chemical application technology is rapidly developed.
The preparation method of the conventional surfactant is generally complex, a catalyst or an initiator is usually required, and the components of the prepared surfactant are complex under the anaerobic condition. The common nano-surface activity also generally needs to be synthesized into the nano-particles, and then the surface activity is adsorbed on the surface of the nano-particles, or the surface activity is combined with the nano-particles by using a coupling agent. The preparation steps are relatively complex and the cost is high.
Disclosure of Invention
According to one aspect of the application, a nano surfactant is provided, and the nano surfactant material with nano scale and interfacial activity is synthesized from bottom to top by adopting a one-step method, so that the reaction process is simplified, and the cost is reduced.
The one-step synthesis from bottom to top in the present application refers to decomposing compounds into atoms or molecules, and the atoms or molecules are aggregated and grown to synthesize the nano material.
According to one aspect of the application, a nano surfactant is provided, and is prepared by reacting fatty amine with a compound A;
the compound A is a micromolecular organic matter or oligomer;
the molecular weight of the micromolecular organic matter and the oligomer is 50-1000.
Optionally, the reaction is a chemical reaction.
Optionally, the small molecule organic matter is at least one selected from small molecule organic acid compounds and small molecule organic saccharide compounds; and/or
The oligomer comprises polyethylene glycol.
Preferably, the small molecular organic acid compound is selected from at least one of citric acid, ethylenediamine tetraacetic acid and malic acid;
the small molecular organic saccharide compound is at least one selected from sucrose, glucose and fructose.
Optionally, the particle size of the nano surfactant is 60-300 nm; interfacial tension of 10 0 ～10 -2 mN/m。
Optionally, the upper limit of the particle size of the nano-surfactant is independently selected from 300nm, 250nm, 200nm, 150nm, 100nm, 70nm, and the lower limit is independently selected from 250nm, 200nm, 150nm, 100nm, 70nm, 60nm.
Optionally, the fatty amine is selected from at least one of primary fatty amines;
preferably, the fatty primary amine is selected from at least one of dodecylamine, tetradecylamine, hexadecylamine and octadecylamine.
In another aspect of the present application, there is also provided a method for preparing the above-mentioned nano surfactant, the method at least comprising: and (3) reacting raw materials containing fatty amine and the compound A, and adjusting the pH value to a preset value to obtain the nano surfactant.
Optionally, the pH is adjusted to a predetermined value to make the nano surfactant safe for use.
Optionally, the reaction conditions are: the reaction temperature is 170-200 ℃; the reaction time is 2-6 h.
Alternatively, the upper limit of the reaction temperature is independently selected from 200 ℃, 190 ℃, 180 ℃, and the lower limit is independently selected from 170 ℃, 180 ℃, 190 ℃.
Optionally, the mass ratio of the fatty amine to the compound a is 1:1-1.
Alternatively, the upper limit of the mass ratio of the fatty amine to the compound a is independently selected from 1:10. 1: 9. 1: 8. 1: 7. 1: 6. 1:5. 1: 4. 1: 3. 1:2, the lower limit is independently selected from 1: 9. 1: 8. 1: 7. 1: 6. 1:5. 1: 4. 1: 3. 1: 2. 1:1.
optionally, the method comprises at least:
(1) Reacting raw materials containing fatty amine and a compound A to obtain an intermediate product;
(2) Obtaining a solution containing the intermediate product, and adjusting the pH of the solution to 6-9 to obtain the nano surfactant.
Optionally, the adjusting the pH of the solution to 6 to 9 comprises: adjusting the pH of the aqueous solution to 6-9 by a pH regulator;
the pH regulator comprises any one of sodium hydroxide, potassium hydroxide and sodium carbonate.
Optionally, the mass ratio of the pH regulator to the compound A is 1:3-1:5.
Optionally, the mass percentage of the intermediate product in the aqueous solution is 1-15%.
Specifically, the smaller the interfacial tension value, the better the nano surfactant effect in the present application, and the higher the interfacial activity.
The beneficial effects that this application can produce include:
the invention adopts a one-step method to synthesize the nano surface active material with nano scale and interface activity from bottom to top, which not only has the performance of the nano material, but also has the performance of a surfactant, and has good foaming performance and viscous oil reducing capability.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
The raw materials in the examples of the present application were all purchased commercially, unless otherwise specified.
The particle size of the Nano surfactant prepared in the examples of the present application was measured using a laser particle sizer (malvern Zetasizer Nano ZSE model Nano particle sizer).
Example 1
Weighing 10g of citric acid, adding into a ground conical flask, then weighing 5g of dodecylamine, adding into the conical flask, uniformly mixing the two raw materials, covering a bottle stopper, placing in an oven at 180 ℃, reacting for 6h, and taking out. Then cooling to room temperature, adding 200mL of deionized water for dissolution, and then adding 2.5g of NaOH to adjust the pH value to 7, thus obtaining the dispersion A containing the nano surfactant.
Example 2
Weighing 10g of sucrose, adding into a ground conical flask, then weighing 1g of tetradecylamine, adding into the conical flask, uniformly mixing the two raw materials, covering a bottle plug, placing into a 190 ℃ oven, reacting for 2h, and taking out. Then cooling to room temperature, adding 100mL of deionized water for dissolution, and then adding 1g of NaOH to adjust the pH value to 6, thus obtaining the dispersion liquid B containing the nano surfactant.
Example 3
Weighing 10g of glucose, adding into a ground conical flask, then weighing 1g of hexadecylamine, adding into the conical flask, uniformly mixing the two raw materials, covering a bottle stopper, placing into a 200 ℃ oven, reacting for 4h, and taking out. Then cooling to room temperature, adding 150mL of deionized water for dissolution, and then adding 1.5g of NaOH to adjust the pH value to 9, thus obtaining the dispersion liquid C containing the nano surfactant.
Example 4
Weighing 5g of malic acid, adding into a ground conical flask, then weighing 1g of octadecylamine, adding into the conical flask, mixing the two raw materials uniformly, covering the bottle stopper, placing in a 190 ℃ oven, reacting for 5h, and taking out. Then cooling to room temperature, adding 200mL of deionized water for dissolution, and then adding 3.3g of NaOH to adjust the pH value to 8, thus obtaining the dispersion liquid D containing the nano surfactant.
Example 5 Performance testing
(1) And (3) particle size testing:
the method comprises the following specific steps: the dispersions prepared in examples 1 to 4 were tested for the particle size of the nano surfactant therein using a laser particle sizer, and the results are shown in table 1.
TABLE 1
Dispersion liquid Particle size of nano surfactant
A 175nm
B 258nm
C 152nm
D 119nm
(2) And (3) interfacial tension test:
the samples of examples 1 to 4 were each subjected to an interfacial tension test using a TX500C series rotary droplet interfacial tensionA force meter; the test results are shown in table 2 and show that: the interfacial tension can reach 10 by using fatty amines with different chain lengths and adjusting the proportion of the fatty amines 0 ～10 -2 mN/m。
TABLE 2
Figure BDA0002484695110000041
Figure BDA0002484695110000051
(3) Foaming Property test
The samples of examples 1 to 4 were diluted with simulated saline in 500ml beakers to 3000ppm concentrations, respectively, and then stirred with a mechanical stirrer at 2200rpm for 1min, the foaming of the solution was observed, and the half-life of the solution and the half-life of the foam were recorded, as typified by example 1, and the results are shown in table 3.
TABLE 3
Figure BDA0002484695110000052
(4) Viscosity reduction capability test of thickened oil
The samples in the embodiments 1 to 4 are diluted to 3000ppm by saline, 14g of thick oil with the viscosity of 1700cP is taken, 6g of diluted sample is added into 14g of thick oil, the experiment temperature is 50 ℃, the stirring reaction is carried out for 60min, the viscosity and the viscosity reduction rate of the thick oil are measured, the viscosity of the thick oil is reduced from 1700cP at the temperature of 50 ℃ to 79P by taking the embodiment 1 as a typical representative, the viscosity reduction rate reaches more than 95%, and the fluidity of the thick oil is improved.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.

Claims (10)

1. A method for preparing a nano surfactant is characterized in that,
the method at least comprises the following steps: reacting raw materials containing fatty amine and a compound A, and adjusting the pH value to a preset value to obtain the nano surfactant;
the reaction conditions are as follows: the reaction temperature is 170 to 200 ℃; the reaction time is 2 to 6h;
the compound A is a micromolecular organic matter or oligomer;
the molecular weight of the small molecular organic matter and the molecular weight of the low molecular organic matter are 50 to 6000;
the micromolecular organic matter is at least one of micromolecular organic acid compounds and micromolecular organic carbohydrate compounds; and/or
The oligomer comprises polyethylene glycol.
2. The production method according to claim 1,
the small molecular organic acid compound is at least one selected from citric acid, ethylenediamine tetraacetic acid and malic acid;
the small molecular organic saccharide compound is at least one selected from sucrose, glucose and fructose.
3. The preparation method according to claim 1, wherein the particle size of the nano surfactant is 60 to 300nm; interfacial tension of 10 0 ~10 -2 mN/m。
4. The method according to claim 1, wherein the aliphatic amine is at least one selected from aliphatic primary amines.
5. The method according to claim 4, wherein the primary aliphatic amine is at least one selected from the group consisting of dodecylamine, tetradecylamine, hexadecylamine, and octadecylamine.
6. The preparation method according to claim 1, wherein the mass ratio of the aliphatic amine to the compound A is 1 to 1.
7. The method for preparing according to claim 1, characterized in that it comprises at least:
(1) Reacting raw materials containing fatty amine and a compound A to obtain an intermediate product;
(2) Obtaining a solution containing the intermediate product, and adjusting the pH of the solution to 6~9 to obtain the nano surfactant.
8. The method of claim 7, wherein the adjusting the pH of the solution to 6~9 comprises: adjusting the pH of the solution to 6~9 by a pH adjuster;
the pH regulator comprises any one of sodium hydroxide, potassium hydroxide and sodium carbonate.
9. The preparation method according to claim 8, wherein the mass ratio of the pH regulator to the compound A is 1 to 3-1.
10. The preparation method according to claim 7, wherein the mass percentage of the intermediate product in the solution is 1 to 15%.
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CN104974185A (en) * 2015-06-15 2015-10-14 陕西科技大学 Glucose gemini surfactant preparation method
CN109485844A (en) * 2018-11-27 2019-03-19 山东蓝星东大有限公司 The preparation method of high activity high molecular polyether polyol polyalcohol

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CN104974185A (en) * 2015-06-15 2015-10-14 陕西科技大学 Glucose gemini surfactant preparation method
CN109485844A (en) * 2018-11-27 2019-03-19 山东蓝星东大有限公司 The preparation method of high activity high molecular polyether polyol polyalcohol

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