CN113667055B - Acrylate-polymerizable quaternary ammonium salt copolymer demulsifier and preparation method thereof - Google Patents
Acrylate-polymerizable quaternary ammonium salt copolymer demulsifier and preparation method thereof Download PDFInfo
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- 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
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- 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
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- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
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Abstract
The invention discloses an acrylate-polymerizable quaternary ammonium salt copolymer demulsifier and a preparation method thereof, wherein the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier is prepared by the following steps: adding acrylate, polymerizable quaternary ammonium salt, acrylamide, dispersant polyethylene glycol 20000 and chelating agent disodium ethylene diamine tetraacetate into a prepared ether-water mixed solvent, mixing and stirring uniformly to obtain a mixed solution, introducing nitrogen into the mixed solution to remove oxygen for 30min, adding an initiator, heating to a reaction temperature, keeping the temperature for reaction for a period of time, cooling and discharging to obtain a demulsifier; the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier provided by the invention has the characteristics of simple and convenient preparation method, safe raw materials and mild conditions, effectively reduces the safety risk in the production process of the conventional demulsifier, has good demulsification effect, and provides a new idea for selection and application of W/O type crude oil emulsion demulsifying agents.
Description
Technical Field
The invention relates to the technical field of oilfield chemicals, in particular to an acrylate-polymerizable quaternary ammonium salt copolymer demulsifier and a preparation method thereof.
Background
The demulsifier is one of common oil field chemicals for treating oil field produced liquid, and has the main function of reducing the water content of crude oil emulsion (W/O emulsion) and facilitating refining operation after crude oil extraction. At present, the nonionic block polyether is the most widely applied crude oil emulsion demulsifier, has the advantages of excellent demulsification performance, wide applicability, high dehydration speed and the like, and is usually prepared by using alcohols, phenolic resin, phenol amine resin and the like as initiators and performing anionic ring-opening polymerization on Ethylene Oxide (EO) and Propylene Oxide (PO). However, in the process of preparing the block polyether, the EO and PO used as raw materials belong to flammable and explosive dangerous chemicals, and high-temperature and high-pressure reaction conditions need to be provided in the synthesis process, so that the process flow is complex, namely, a relatively high safety risk exists in the conventional production process. Therefore, the search for other compounds to replace block polyethers as demulsifiers is one of the major development directions of the demulsifiers at present. In recent years, the acrylic ester amphiphilic polymer gradually attracts attention, has the characteristics of simple process and low cost, and is applied as a reverse demulsifier (for treating O/W emulsion) in the field of produced fluid treatment, but research reports and related applications of the demulsifier are less, so that the acrylic ester amphiphilic polymer with mild and simple synthesis conditions has wider research and application prospects when being applied to the demulsifier.
Disclosure of Invention
According to the defects of the application of the existing block polyether demulsifier, the invention provides the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier and the preparation method thereof, the non-block polyether demulsifier is prepared under relatively mild reaction conditions, the safety risk in the production process of the traditional block polyether demulsifier is effectively reduced, and meanwhile, a new medicament selection is provided for W/O type crude oil emulsion demulsification.
The invention discloses a preparation method of an acrylate-polymerizable quaternary ammonium salt copolymer demulsifier, which comprises the following steps:
adding acrylate, polymerizable quaternary ammonium salt, acrylamide, dispersant polyethylene glycol 20000 and chelating agent disodium ethylene diamine tetraacetate into a prepared ether-water mixed solvent, and uniformly mixing and stirring to obtain a mixed solution;
introducing nitrogen into the mixed solution obtained in the step (1) to remove oxygen for 30min, and then adding an initiator;
and (3) heating the mixed solution added with the initiator in the step (2) to a reaction temperature, keeping the temperature for reaction for a period of time, cooling and discharging to obtain the demulsifier.
One embodiment of the present invention is that the acrylate in the step (1) includes methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, isooctyl methacrylate, t-butyl methacrylate and 2-hydroxyethyl methacrylate.
Another embodiment of the present invention is that the polymerizable quaternary ammonium salts in the step (1) include methacryloyloxyethyl trimethyl ammonium chloride, acryloyloxyethyl trimethyl ammonium chloride and diallyldimethyl ammonium chloride.
Another embodiment of the present invention is that the ether constituting the ether-water mixture solvent in the step (1) includes ethylene glycol dimethyl ether, diethylene glycol butyl ether, ethylene glycol butyl ether, dipropylene glycol methyl ether and diethylene glycol butyl ether.
Another embodiment of the invention is that, in the step (1), the ether water in the ether water mixture solvent has a mass part ratio of 1: 0.6-1.5.
Another embodiment of the invention is that, in the step (1), the total of three monomers, namely acrylate, polymerizable quaternary ammonium salt and acrylamide, accounts for 20-35% of the total reaction liquid by mass fraction, wherein acrylamide accounts for 4.5-5.5% of the three monomers, and the mass fraction ratio of the polymerizable quaternary ammonium salt to the acrylate is 1: 1-3.5.
In another embodiment of the present invention, in the step (1), the dispersant polyethylene glycol 20000 accounts for 0.8% -1.2% of the total reaction solution, and the chelating agent disodium ethylene diamine tetraacetate accounts for 0.08% -0.12% of the total reaction solution by mass fraction.
Another embodiment of the present invention is that the initiator in the step (2) comprises V-50, VA-044, ammonium persulfate, potassium persulfate and azobisisobutyronitrile; and the initiator accounts for 0.3 to 1.0 percent of the total reaction liquid by mass fraction.
Another embodiment of the invention is that the reaction temperature in the step (3) is 50-70 ℃ and the reaction time is 8 h.
The invention also discloses the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier prepared by the preparation method.
Compared with the prior art, the invention has the technical effects that:
the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier provided by the invention is used as a non-block polyether demulsifier, has the characteristics of simple and convenient preparation method, safe raw materials and mild conditions, effectively reduces the safety risk in the production process of the demulsifier compared with the existing block polyether demulsifier, has good demulsification effect, and provides a new thought for the selection and application of W/O type crude oil emulsion demulsifying agents.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
Example 1
42.55g of dipropylene glycol methyl ether and 28.37g of deionized water are weighed in a three-necked bottle and uniformly mixed to prepare an ether-water mixed solvent, 11.88g of butyl acrylate, 14.85g of methacryloyloxyethyl trimethyl ammonium chloride in the form of 80% aqueous solution, 1.25g of acrylamide, 1g of PEG-20000 and 0.1g of disodium ethylene diamine tetraacetate are respectively added into the ether-water mixed solvent, the mixture is stirred and dissolved and uniformly mixed, then nitrogen is introduced to remove oxygen for 30min, 0.2g of azobisisobutyronitrile is added, the total reaction liquid is heated to 55 ℃, stirred and reacted for 8h, and after the reaction is finished, the mixture is cooled and discharged to obtain the demulsifier product.
Example 2
This example is the same as example 1 except that the amounts of dipropylene glycol methyl ether and deionized water added in this example were 38.68g and 32.24g, respectively.
Example 3
The embodiment of this example is the same as example 1, except that the amounts of dipropylene glycol methyl ether and deionized water added in this example are 35.46g and 35.46g, respectively.
Example 4
This example is the same as example 1 except that dipropylene glycol methyl ether and deionized water were added in amounts of 32.24g and 38.68g, respectively.
Example 5
This example is the same as example 1 except that dipropylene glycol methyl ether and deionized water were added in amounts of 28.37g and 42.55g, respectively.
Example 6
42.55g of dipropylene glycol methyl ether and 28.37g of deionized water are weighed in a three-necked bottle and uniformly mixed to prepare an ether-water mixed solvent, then 17.81g of butyl acrylate, 7.42g of methacryloyloxyethyl trimethyl ammonium chloride in the form of 80% aqueous solution, 1.25g of acrylamide, 1g of PEG-20000 and 0.1g of disodium ethylene diamine tetraacetate are respectively added into the ether-water mixed solvent, the mixture is stirred and dissolved and uniformly mixed, then nitrogen is introduced to remove oxygen for 30min, then 0.2g of azobisisobutyronitrile is added, then the total reaction liquid is heated to 55 ℃, stirred and reacted for 8h, and after the reaction is finished, the mixture is cooled and discharged to obtain the demulsifier product.
Example 7
This example is carried out in the same manner as example 2 except that in this example, butyl acrylate and methacryloyloxyethyltrimethyl ammonium chloride were 15.83g and 9.89g, respectively.
Example 8
The embodiment of this example is the same as example 1, except that in this example, butyl acrylate in example 1 is changed to ethyl acrylate.
Example 9
This example is carried out in the same manner as example 1 except that butyl acrylate in example 1 is replaced by ethyl methacrylate.
Example 10
This example is the same as example 1, except that butyl acrylate in example 1 is replaced with butyl methacrylate.
Example 11
This example is performed in the same manner as example 1 except that the butyl acrylate used in example 1 is replaced with isooctyl methacrylate.
Example 12
This example is the same as example 1 except that butyl acrylate in example 1 is changed to t-butyl methacrylate.
Example 13
This example is performed in the same manner as example 1 except that butyl acrylate in example 1 is replaced with 2-hydroxyethyl methacrylate.
Example 14
The embodiment of this example is the same as example 1, except that in this example, dipropylene glycol methyl ether in example 1 is changed to ethylene glycol dimethyl ether.
Example 15
The embodiment of this example is the same as example 1 except that dipropylene glycol methyl ether in example 1 is changed to ethylene glycol butyl ether in this example.
Example 16
The embodiment of this example is the same as example 1 except that dipropylene glycol methyl ether in example 1 is changed to diethylene glycol butyl ether in this example.
Example 17
This example is carried out in the same manner as example 1 except that methacryloyloxyethyltrimethyl ammonium chloride in example 1 is replaced with acryloyloxyethyltrimethyl ammonium chloride.
Example 18
This example is carried out in the same manner as in example 1 except that methacryloyloxyethyltrimethylammonium chloride in example 1 is replaced with diallyldimethylammonium chloride.
In order to further illustrate the technical effects of the present invention, the present invention further provides the related characterization and test of the above embodiments in practical application.
1. Evaluation of influence of mixed solvent ratio selection on demulsifier performance
The thick oil (density 0.9645 g/cm) of a certain oil field is used 3 ) 5 groups of W/O emulsions with water content of 50% are prepared as an oil phase, and as test objects, the demulsifiers prepared in the examples 1-5 are respectively added into the 5 groups of W/O emulsions at the concentration of 200mg/L for dehydration experiments, and when the test temperature is 70 ℃, the dehydration rate of the demulsifiers obtained in 4 hours is shown in Table 1:
TABLE 1 dehydration Effect of demulsifiers in examples 1-5
| Demulsifier | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 |
| Dehydration Rate (%) | 85.5 | 80.5 | 75.0 | 75.0 | 75.0 |
As can be seen from the data in Table 1, the dehydration effect of the demulsifier in examples 3-5 is substantially the same, and the dehydration effect is gradually improved from example 2 to example 1, while the difference between examples 1-5 is mainly that the ratio of ether to water in the mixed solvent of ether and water is gradually reduced, and this phenomenon is mainly caused by that when the ether content in the mixed solvent is higher, the raw material for preparing the demulsifier can have better dispersion effect in the mixed solvent, so that the molecular weight of the polymer of the produced product is controlled to a suitable level, i.e., the larger the amount of ether used, the smaller the molecular weight of the produced product is, and when the product with smaller molecular weight is used in the demulsification process, the product with smaller molecular weight is more easily diffused from the continuous phase to the dispersed phase, and finally the better dehydration effect is obtained.
2. Evaluation of the Effect of comonomer ratio selection on demulsifier Performance
The thick oil (density 0.9645 g/cm) of a certain oil field is used 3 ) 3 groups of W/O emulsions with water content of 50% are prepared as an oil phase, and as test objects, the demulsifiers prepared in examples 1, 6 and 7 are respectively added into the 3 groups of W/O emulsions at the concentration of 200mg/L for dehydration experiments, and when the test temperature is 70 ℃, the dehydration rate of the demulsifiers obtained in 4 hours is shown in Table 2:
TABLE 2 dehydration Effect of demulsifiers in examples 1, 6 and 7
| Demulsifier | Example 1 | Example 6 | Example 7 |
| Dehydration Rate (%) | 85.5 | 70.5 | 75.0 |
As can be seen from table 2, the dewatering effect is the best in example 1 compared with examples 6 and 7, and the main difference between examples 1, 6 and 7 is that the mass ratio of butyl acrylate to methacryloyloxyethyl trimethyl ammonium chloride is different, the mass ratio of butyl acrylate to methacryloyloxyethyl trimethyl ammonium chloride in example 1 is 1:1, and butyl acrylate has higher content in the other two examples, so that the finally obtained polymerization product has stronger lipophilicity, reduced amphiphilicity and reduced adsorption capacity at the oil-water interface, therefore, the adsorption capacity of the demulsifier synthesized in example 1 at the oil-water interface is higher than that of the demulsifiers in examples 6 and 7, and thus example 1 finally has better dewatering effect.
3. Evaluation of the Effect of comonomer type selection on demulsifier Performance
The heavy oil (density 0.9645 g/cm) of a certain oil field is used as the heavy oil 3 ) 6 groups of W/O emulsions with water content of 50% are prepared as an oil phase, and as test objects, the demulsifiers prepared in examples 8-13 are respectively added into the 6 groups of W/O emulsions at a concentration of 200mg/L for dehydration experiments, and when the test temperature is 70 ℃, the dehydration rate of the demulsifiers obtained in 4 hours is shown in Table 3:
TABLE 3 dehydration Effect of demulsifiers in examples 8-13
| Demulsifier | Example 8 | Example 9 | Example 10 | Example 11 | Example 12 | Example 13 |
| Dehydration Rate (%) | 72.5 | 88.5 | 90.5 | 84.0 | 88.5 | 74.0 |
As shown in Table 3, the dehydration effect of the demulsifier is best when butyl methacrylate is used as the comonomer in example 10, and the main difference between examples 8-13 is that the ester monomers used in the synthesis are changed, the lipophilicity of different ester monomers is different, the amphiphilicity of the final product is also different, and the polymer with proper amphiphilicity has better dehydration effect.
4. Evaluation of influence of selection of different components in mixed solvent on demulsifier performance
The thick oil (density 0.9645 g/cm) of a certain oil field is used 3 ) 5 groups of W/O emulsions with water content of 50% are prepared as an oil phase, and as test objects, the demulsifiers prepared in the examples 8-13 are respectively added into the 5 groups of W/O emulsions at the concentration of 200mg/L for dehydration experiments, and when the test temperature is 70 ℃, the dehydration rate of the demulsifiers obtained in 4 hours is shown in Table 4:
TABLE 4 dehydration Effect of demulsifiers in examples 14-18
| Demulsifier | Example 14 | Example 15 | Example 16 | Example 17 | Example 18 |
| Dehydration Rate (%) | 89.0 | 81.5 | 91.0 | 87.5 | 72.5 |
As shown in Table 4, the demulsifier for polymerization products obtained in example 16 using butyl diglycol as a raw material of the mixed solvent exhibited the best dewatering effect. The difference between examples 14-16 is that the ether used in the mixed solvent during synthesis is changed, and the different polarities of the different ethers result in different polarities of the mixed product, which ultimately affects the molecular weight of the product, and it can be seen that the demulsifier synthesized from the mixed solvent of butyl diglycol and water has the most suitable molecular weight, and the dehydration effect is the best. In addition, the main difference between examples 17 and 18 is that the polarity of different polymerizable quaternary ammonium salts is different by changing the type of the polymerizable quaternary ammonium salt during synthesis, thereby affecting the implementation effect of the demulsifier.
The evaluation and characterization of the above embodiments show that the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier has mild and simple preparation conditions, the average dehydration rate of the product can reach more than 80%, a good demulsification effect is realized, the requirements of oil field production can be effectively met, the safety problem existing in the production process of the existing block polyether demulsifier is solved, and a new choice is provided for the application of the crude oil demulsifier.
The above description is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the embodiments of the present invention are included in the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (9)
1. The preparation method of the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier is characterized by comprising the following steps:
adding acrylate, polymerizable quaternary ammonium salt, acrylamide, dispersant polyethylene glycol 20000 and chelating agent disodium ethylene diamine tetraacetate into a prepared ether-water mixed solvent, and uniformly mixing and stirring to obtain a mixed solution;
introducing nitrogen into the mixed solution obtained in the step (1) to remove oxygen for 30min, and then adding an initiator;
step (3), heating the mixed solution added with the initiator in the step (2) to a reaction temperature, keeping the temperature for reaction for a period of time, and cooling and discharging to obtain a demulsifier;
wherein, in the step (1), the sum of the three monomers of the acrylate, the polymerizable quaternary ammonium salt and the acrylamide accounts for 20-35% of the total reaction liquid, the acrylamide accounts for 4.5-5.5% of the three monomers, and the mass part ratio of the polymerizable quaternary ammonium salt to the acrylate is 1: 1-3.5.
2. The preparation method of the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier according to claim 1, wherein the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier comprises the following steps: the acrylic ester in the step (1) comprises methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, isooctyl methacrylate, tert-butyl methacrylate and 2-hydroxyethyl methacrylate.
3. The preparation method of the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier according to claim 1, wherein the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier comprises the following steps: the polymerizable quaternary ammonium salt in the step (1) comprises methacryloyloxyethyl trimethyl ammonium chloride, acryloyloxyethyl trimethyl ammonium chloride and diallyl dimethyl ammonium chloride.
4. The preparation method of the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier according to claim 1, wherein the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier comprises the following steps: the ether forming the ether-water mixture solvent in the step (1) comprises ethylene glycol dimethyl ether, diethylene glycol butyl ether, ethylene glycol butyl ether, dipropylene glycol methyl ether and diethylene glycol butyl ether.
5. The preparation method of the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier according to claim 1, wherein the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier comprises the following steps: the mass part ratio of ether to water in the ether-water mixture solvent in the step (1) is 1: 0.6-1.5.
6. The preparation method of the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier according to claim 1, wherein the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier comprises the following steps: in the step (1), the dispersant polyethylene glycol 20000 accounts for 0.8-1.2% of the total reaction solution, and the chelating agent disodium ethylene diamine tetraacetate accounts for 0.08-0.12% of the total reaction solution.
7. The method for preparing the demulsifier of the acrylate-polymerizable quaternary ammonium salt copolymer according to claim 1, wherein the method comprises the following steps: the initiator in the step (2) comprises V-50, VA-044, ammonium persulfate, potassium persulfate and azobisisobutyronitrile; and the initiator accounts for 0.3 to 1.0 percent of the total reaction liquid by mass fraction.
8. The preparation method of the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier according to claim 1, wherein the acrylate-polymerizable quaternary ammonium salt copolymer demulsifier comprises the following steps: the reaction temperature in the step (3) is 50-70 ℃, and the reaction time is 8 h.
9. An acrylate-polymerizable quaternary ammonium salt copolymer demulsifier prepared according to the preparation method of any one of claims 1 to 8.
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