CN114316926B - Chitosan oil field clay stabilizer based on Mannich reaction and preparation method thereof - Google Patents
Chitosan oil field clay stabilizer based on Mannich reaction and preparation method thereof Download PDFInfo
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Abstract
The invention provides a chitosan oil field clay stabilizer based on Mannich reaction and a preparation method thereof, wherein chitosan, an acid component and an aldehyde component are mixed and heated to obtain a mixed solution, and the pH value of the mixed solution is adjusted to be acidic to obtain a solid product; and washing the solid product, and then freeze-drying to obtain the modified chitosan clay stabilizer. According to the invention, chitosan is used as an amine component, the chitosan, an acid component and an aldehyde component are mixed for Mannich reaction, the modification of chitosan cations is realized, and an anionic group containing acid radical is introduced into the structure of the chitosan, so that the clay stabilizer with temperature resistance and salt tolerance is obtained, the clay stabilizer can be strongly adsorbed to the clay surface, is not easy to decompose, has long effective period, has the temperature resistance up to 250 ℃ and the anti-swelling rate more than 90%.
Description
Technical Field
The invention belongs to the technical field of oilfield development, and particularly belongs to a chitosan oilfield clay stabilizer based on Mannich reaction and a preparation method thereof.
Background
The clay minerals are widely present in oil layers, and most of the oil layers in which the oil reservoirs are located belong to sandstone oil reservoirs and also commonly contain the clay minerals. With the deep development of an oil reservoir, in the processes of well drilling, well completion, perforation, acidification, fracturing, water injection, oil extraction and the like, the contact of an external additive and clay minerals in an oil layer can destroy the original physical and chemical balance in the stratum, so that the clay minerals are dispersed and transported to block the stratum void structure, the stratum permeability is reduced, and the oil layer is damaged finally. Secondly, in the exploration and development process of petroleum, the influence of hydration expansion of clay minerals on the quality of an oil layer is large, so that the problems of low permeability, high temperature and high mineralization degree of the oil reservoir can be caused, the reservoir is seriously damaged, and the yield of an oil well is reduced or even the production is stopped.
The clay stabilizer is a chemical which can be adsorbed on the clay surface, avoids the damage of the water-sensitive minerals caused by hydration expansion and dispersion transfer to the oil-gas layer, and can effectively prevent the damage to the oil layer in the exploitation process. The clay stabilizer is mainly divided into inorganic salt and inorganic alkali clay stabilizer, inorganic polynuclear polymer clay stabilizer, cationic surfactant and organic cationic polymer clay stabilizer. The organic cation polymer clay stabilizer has the advantages of wide application range, good stabilizing effect, long effective time and strong acid, alkali, oil and water resistance washing capability. The current research and development on this class of materials mainly includes the use of various types of natural polymers, such as starch, lignin, caoutchouc, illegal cooking oil, polymeric sugar, cellulose, etc. (drilling and production process, 2015, 38, 98; forestry chemistry and industry, 1998, 3. Part of raw materials or products have groups which are high in toxicity and difficult to degrade, such as benzene rings, chlorophenols, thiophene and the like in the molecular structure, so that the clay stabilizer is high in toxicity, pollutes the environment and causes damage to a reservoir; secondly, some processes need to strictly control experimental reaction conditions, the process is complicated, and the production efficiency is low. And some clay stabilizers are not suitable for high temperature environments, limiting their application in stabilizing clays.
Disclosure of Invention
In order to solve the problems of high toxicity, environmental pollution, complex process and low production efficiency of the clay stabilizer prepared in the prior art, the invention provides a chitosan oil field clay stabilizer based on Mannich reaction and a preparation method thereof.
In order to achieve the purpose, the invention provides the following technical scheme: a chitosan oil field clay stabilizer based on Mannich reaction comprises the following specific steps:
s1, mixing chitosan, an acid component and an aldehyde component, heating to obtain a mixed solution, and adjusting the pH value of the mixed solution to acidity to obtain a solid product;
s2, washing the solid product, and then carrying out freeze drying to obtain the modified chitosan clay stabilizer.
Further, in the step S1, the mass ratio of the chitosan, the acid component and the aldehyde component is 1 (0.16-0.6) to 0.2-1.15.
Further, in step S1, the acid component is one of 2-acrylamide-2-methylpropanesulfonic acid, phosphorous acid, methacrylic acid, and acetic acid.
Further, in step S1, the aldehyde component is one of glutaraldehyde, salicylaldehyde, methylglyoxal, glyoxal, and furfural.
Further, in the step S1, the heating is carried out for 4 to 12 hours at the temperature of 45 ℃.
Further, in step S1, naOH with the concentration of 0.2-0.6 mol/L is adopted to adjust the pH value of the mixed solution to 4.5-6.5.
Further, in step S2, ethanol and distilled water are used for washing.
Further, in step S2, the freeze drying is carried out for 10 to 24 hours under the conditions of 3 to 15MPa and-40 to-60 ℃.
The invention also provides a chitosan oil field clay stabilizer based on Mannich reaction, which is prepared according to the preparation method, wherein the clay stabilizer has the temperature resistance of 250 ℃ and the anti-swelling rate of more than 90%.
Compared with the prior art, the invention has at least the following beneficial effects:
the invention discloses a chitosan oil field clay stabilizer and a preparation method thereof, wherein a Mannich reaction is adopted, chitosan, acid and aldehyde are used as raw materials to prepare the clay stabilizer, wherein the chitosan is used as a natural organic high molecular polymer, has the advantages of wide source, low price, better biodegradability and the like, and can utilize-OH-NH contained in the molecule thereof 2 The active groups are modified, so that a foundation is laid for synthesizing the clay stabilizer with excellent performance, and the problems of high toxicity and environmental pollution in the preparation of the clay stabilizer in the prior art are solved.
The invention also discloses the chitosan oil field clay stabilizer prepared by the preparation method, the Mannich reaction has the advantages of simple and convenient operation, low energy consumption, mild reaction conditions and high grafting efficiency, and the synthesized clay stabilizer containing cations has the properties of temperature resistance and salt tolerance. The introduced acid radical anions such as carboxyl, sulfonic acid group and the like are taken as strong hydration groups to form multi-point adsorption with the surfaces of a plurality of clay particles, so that a compact hydration film is formed, water molecules are prevented from contacting with the surfaces of the clay, and finally the effect of preventing the hydration expansion of the clay is achieved; meanwhile, nitrogen cations contained in the side chains have larger freedom of movement, have strong control effect on the dispersion and migration of clay particles, have strong washing resistance, also have the effects of high temperature resistance, salt resistance and pollution resistance, are clay stabilizers with excellent performance, and further promote the application in stabilizing clay. The chitosan is generally dissolved in inorganic acid or organic acid and can not be directly dissolved in water, and an acid component in the Mannich reaction can be just used as a reaction raw material and can assist in dissolving the chitosan, so that the reaction is promoted, and the reaction efficiency is improved.
The invention also discloses application of the chitosan oil field clay stabilizer. The material can be strongly adsorbed on the clay surface, is not easy to decompose, has long effective period, and has the temperature resistance of 250 ℃ and the anti-swelling rate of more than 90 percent.
Drawings
FIG. 1 schematic representation of the Mannich reaction of the present invention.
Detailed Description
In order to make the technical solutions of the present invention better understood, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It should be noted that the terms "first," "second," and the like in the description and claims of the present invention and in the drawings described above are used for distinguishing between similar elements and not necessarily for describing a particular sequential or chronological order. It is to be understood that the data so used is interchangeable under appropriate circumstances such that the embodiments of the invention described herein are capable of operation in sequences other than those illustrated or described herein. Furthermore, the terms "comprises," "comprising," and "having," and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements expressly listed, but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
As shown in figure 1, a chitosan oil field clay stabilizer based on Mannich reaction comprises the following steps:
(1) Adding chitosan and an acid component which are used as amine components into 100mL of water under the stirring condition to obtain a uniform mixed solution;
(2) Adding an aldehyde component into the mixed solution, stirring for 4-12 h at 45 ℃, adjusting the pH value of the mixed solution to 4.5-6.5 by adopting NaOH, and separating out a solid product, wherein the solid product comprises a polymer after reaction and an unreacted monomer;
(3) Filtering and washing the solid product with ethanol and distilled water, washing off unreacted monomers on the polymer, and freeze-drying for 10-24 h under the conditions of 3-15 MPa, -40-60 ℃ to obtain the modified chitosan clay stabilizer.
FIG. 1 is a schematic diagram of a Mannich reaction of the present invention, wherein R1 is an acid component, specifically comprising one of 2-acrylamide-2-methylpropanesulfonic acid, phosphorous acid, methacrylic acid, and acetic acid; r2 is an aldehyde component, and specifically comprises one of glutaraldehyde, salicylaldehyde, methylglyoxal, glyoxal and furfural.
Wherein the mass ratio of the chitosan, the acid component and the aldehyde component is 1 (0.16-0.6) to 0.2-1.15.
Wherein the concentration of NaOH is 0.2-0.6 mol/L.
Example 1:
(1) Under the condition of stirring, 2g of chitosan and 1.09g of 2-acrylamide-2-methylpropanesulfonic acid are added into 100mL of water to obtain a uniform mixed solution;
(2) Adding 0.53g of glutaraldehyde into the mixed solution, stirring for 4h at 45 ℃, then slowly adding 0.2mol/L NaOH, adjusting the pH of the mixed solution to 4.5, and finally precipitating to obtain a solid product, wherein the mass ratio of the chitosan to the 2-acrylamide-2-methylpropanesulfonic acid to the glutaraldehyde is 1;
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-40 ℃ and the pressure of 3MPa for 10 hours to obtain the modified chitosan clay stabilizer.
Example 2:
(1) Adding 2g of chitosan and 0.41g of phosphorous acid into 100mL of water under the condition of stirring to obtain a uniform mixed solution;
(2) Adding 1.22g of salicylaldehyde solution into the mixed solution, stirring for 6 hours at 45 ℃, then slowly adding 0.3mol/L NaOH, adjusting the pH of the mixed solution to 5, and finally precipitating to obtain a solid product, wherein the mass ratio of the chitosan to the phosphorous acid to the salicylaldehyde is 1;
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-45 ℃ and under the pressure of 6MPa for 15 hours to obtain the modified chitosan clay stabilizer.
Example 3:
(1) Adding 2g of chitosan and 0.86g of methacrylic acid into 100mL of water under the stirring condition to obtain a uniform mixed solution;
(2) Adding 1.15g of methylglyoxal solution into the mixed solution, stirring for 7h at 45 ℃, then slowly adding 0.4mol/L NaOH, adjusting the pH value of the mixed solution to 5.5, and finally precipitating to obtain a solid product, wherein the mass ratio of chitosan to methacrylic acid to methylglyoxal is 1;
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-50 ℃ and the pressure of 10MPa for 18 hours to obtain the modified chitosan clay stabilizer.
Example 4:
(1) Adding 2g of chitosan and 0.6g of acetic acid into 100mL of water under the condition of stirring to obtain a uniform mixed solution;
(2) Adding 1.16g of glyoxal solution into the mixed solution, stirring for 8h at 45 ℃, then slowly adding 0.6mol/L NaOH, adjusting the pH of the mixed solution to 6.5, and finally precipitating to obtain a solid product, wherein the mass ratio of chitosan to acetic acid to glyoxal is 1;
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-60 ℃ and under the pressure of 15MPa for 24 hours to obtain the modified chitosan clay stabilizer.
Example 5:
(1) Adding 2g of chitosan and 0.32g of acetic acid into 100mL of water under the condition of stirring to obtain a uniform mixed solution;
(2) Adding 0.4g of furfural solution into the mixed solution, stirring at 45 ℃ for 9h, then slowly adding 0.5mol/L NaOH, adjusting the pH value of the mixed solution to 6, and finally precipitating to obtain a solid product, wherein the mass ratio of chitosan to acetic acid to furfural is 1;
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-50 ℃ and the pressure of 13MPa for 22 hours to obtain the modified chitosan clay stabilizer.
Example 6:
(1) Adding 2g of chitosan and 0.32g of acetic acid into 100mL of water under the condition of stirring to obtain a uniform mixed solution;
(2) Adding 2.3g of glyoxal solution into the mixed solution, stirring for 10h at 45 ℃, then slowly adding 0.2mol/L NaOH, adjusting the pH of the mixed solution to 6, and finally precipitating to obtain a solid product, wherein the mass ratio of chitosan to acetic acid to glyoxal is 1;
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-50 ℃ and the pressure of 3MPa for 15 hours to obtain the modified chitosan clay stabilizer.
Example 7:
(1) Under the condition of stirring, 2g of chitosan and 1.2g of methacrylic acid are added into 100mL of water to obtain a uniform mixed solution;
(2) Adding 0.77g of methylglyoxal solution into the mixed solution, stirring for 11h at 45 ℃, then slowly adding 0.4mol/L NaOH, adjusting the pH value of the mixed solution to 5, and finally precipitating to obtain a solid product, wherein the mass ratio of chitosan, methacrylic acid and methylglyoxal is 1;
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-40 ℃ and under the pressure of 15MPa for 22 hours to obtain the modified chitosan clay stabilizer.
Example 8:
(1) Under the condition of stirring, 2g of chitosan and 1.2g of phosphorous acid are added into 100mL of water to obtain a uniform mixed solution; then slowly adding 0.6mol/L NaOH, adjusting the pH value of the mixed solution to 4.5, and finally separating out to obtain a solid product;
(2) Adding 2.3g of salicylaldehyde solution into the mixed solution, stirring at 45 ℃ for 12h, wherein the mass ratio of the chitosan to the phosphorous acid to the salicylaldehyde is 1.6,
(3) And filtering and washing the solid product by using ethanol and distilled water, and then freeze-drying at the temperature of-60 ℃ and the pressure of 13MPa for 22 hours to obtain the modified chitosan clay stabilizer.
The anti-swelling rate and the effective period of the product under the conditions of the temperature of 250 ℃ and the degree of mineralization of 200000mg/L are evaluated according to the performance evaluation method of the clay stabilizer for water injection SY/T5971-94, and the results are shown in Table 1.
TABLE 1 comparison of Clay stabilizers
The performance data of the clay stabilizer prepared by mixing chitosan, an acid component and an aldehyde component according to different proportions are shown in Table 1, and it can be seen that the anti-swelling rates of the chitosan oil field clay stabilizers prepared based on the Mannich reaction in examples 1-8 are all more than 90%, and the temperature resistance is all more than 250 ℃, which indicates that the clay stabilizer developed by the invention has good capability of preventing the hydration expansion of bentonite under the conditions of 250 ℃ and 200000mg/L mineralization.
Claims (4)
1. A preparation method of a chitosan oil field clay stabilizer based on Mannich reaction is characterized by comprising the following specific steps:
s1, mixing chitosan, an acid component and an aldehyde component, heating to obtain a mixed solution, and adjusting the pH value of the mixed solution to 4.5-6.5 to obtain a solid product;
s2, washing the solid product, and then carrying out freeze drying to obtain a modified chitosan clay stabilizer;
in the step S1, the mass ratio of the chitosan to the acid component to the aldehyde component is 1 (0.16-0.6) to 0.2-1.15;
in the step S1, the acid component is one of 2-acrylamide-2-methylpropanesulfonic acid, phosphorous acid, methacrylic acid and acetic acid;
in the step S1, the aldehyde component is one of glutaraldehyde, salicylaldehyde, methylglyoxal, glyoxal and furfural;
in the step S1, heating for 4h to 12h at 45 ℃;
in the step S2, the freeze drying is carried out for 10 to 24 hours under the conditions of 3 to 15MPa and-40 to-60 ℃.
2. The preparation method of the chitosan oilfield clay stabilizer based on the Mannich reaction as claimed in claim 1, wherein in the step S1, naOH with a concentration of 0.2 to 0.6mol/L is used to adjust the pH value of the mixed solution.
3. The preparation method of the chitosan oil field clay stabilizer based on Mannich reaction according to claim 1, wherein in step S2, ethanol and distilled water are used for washing.
4. A chitosan oil field clay stabilizer based on Mannich reaction, which is prepared according to the preparation method of any one of claims 1 to 3, and has temperature resistance of 250 ℃ and swelling resistance rate of more than 90%.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106336467A (en) * | 2016-08-25 | 2017-01-18 | 中国石油大学(北京) | Modified chitosan, preparation method thereof, application of chitosan as shale inhibitor, drilling fluid and application thereof |
| CN106367042A (en) * | 2016-08-25 | 2017-02-01 | 中国石油大学(北京) | Application of modified chitosan as shale inhibitor and application of anti-temperature and environment-friendly water-based drilling fluid |
| CN109553701A (en) * | 2017-09-25 | 2019-04-02 | 西南石油大学 | A kind of preparation method of modification of chitosan polymer |
| CN111748048A (en) * | 2020-08-03 | 2020-10-09 | 西南石油大学 | Preparation method of modified chitosan acidizing corrosion inhibitor |
| CN112391155A (en) * | 2021-01-19 | 2021-02-23 | 东营浩辰石油技术开发有限公司 | Polymer drag reducer for oil and gas exploitation and preparation process thereof |
| CN113698510A (en) * | 2020-08-26 | 2021-11-26 | 中国石油大学(北京) | Modified chitosan as environment-friendly bionic shale inhibitor for water-based drilling fluid |
| CN113897187A (en) * | 2021-11-27 | 2022-01-07 | 石家庄华莱鼎盛科技有限公司 | Polymer clean drilling fluid system |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6358889B2 (en) * | 1998-12-28 | 2002-03-19 | Venture Innovations, Inc. | Viscosified aqueous chitosan-containing well drilling and servicing fluids |
| US6291404B2 (en) * | 1998-12-28 | 2001-09-18 | Venture Innovations, Inc. | Viscosified aqueous chitosan-containing well drilling and servicing fluids |
| CA3042626C (en) * | 2016-12-07 | 2022-08-09 | Halliburton Energy Services, Inc. | Embedded treatment fluid additives for use in subterranean formation operations |
-
2022
- 2022-01-11 CN CN202210026817.0A patent/CN114316926B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106336467A (en) * | 2016-08-25 | 2017-01-18 | 中国石油大学(北京) | Modified chitosan, preparation method thereof, application of chitosan as shale inhibitor, drilling fluid and application thereof |
| CN106367042A (en) * | 2016-08-25 | 2017-02-01 | 中国石油大学(北京) | Application of modified chitosan as shale inhibitor and application of anti-temperature and environment-friendly water-based drilling fluid |
| CN109553701A (en) * | 2017-09-25 | 2019-04-02 | 西南石油大学 | A kind of preparation method of modification of chitosan polymer |
| CN111748048A (en) * | 2020-08-03 | 2020-10-09 | 西南石油大学 | Preparation method of modified chitosan acidizing corrosion inhibitor |
| CN113698510A (en) * | 2020-08-26 | 2021-11-26 | 中国石油大学(北京) | Modified chitosan as environment-friendly bionic shale inhibitor for water-based drilling fluid |
| CN112391155A (en) * | 2021-01-19 | 2021-02-23 | 东营浩辰石油技术开发有限公司 | Polymer drag reducer for oil and gas exploitation and preparation process thereof |
| CN113897187A (en) * | 2021-11-27 | 2022-01-07 | 石家庄华莱鼎盛科技有限公司 | Polymer clean drilling fluid system |
Non-Patent Citations (2)
| Title |
|---|
| an environmental friendly and biodegradable shale inhibitor based on chitosan quaternary ammonium salt;An YX;《journal of petroleum science and engineering》;20151130;第135卷;第235-260页 * |
| 环保型页岩抑制剂壳聚糖铵盐的性能研究;刘建设;《云南化工》;20190530;第46卷(第5期);第26-30页 * |
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