CN114426641B - Bio-based demulsifier, preparation method thereof and treatment method of crude oil water-in-oil emulsion - Google Patents
Bio-based demulsifier, preparation method thereof and treatment method of crude oil water-in-oil emulsion Download PDFInfo
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Abstract
The invention belongs to the technical field of demulsifiers, and discloses a bio-based demulsifier, a preparation method thereof and a treatment method of crude oil water-in-oil emulsion. The bio-based demulsifier comprises a polymer polymerized from itaconic acid, dimethyl itaconate and dibutyl itaconate; the structural formula of the polymer comprises structural units shown in a formula M, N, X.
Description
Technical Field
The invention belongs to the technical field of demulsifiers, and in particular relates to a bio-based demulsifier, a preparation method thereof and a treatment method of crude oil water-in-oil emulsion.
Background
The bio-based chemicals are a general term for organic matters obtained directly or indirectly through photosynthesis of green plants or microorganisms, and the process is bulk or fine chemicals produced by means of bioengineering, chemical engineering, physical methods and the like by taking biomass resources as main raw materials.
As early as the 19 th century, it was known how to use fermentation products of biobased feedstocks to make foods, chemicals and fuels, and biobased conversion technology developed into the 40 th 19 th century, with nearly 30% of industrial chemicals being derived from plant materials. The american scientist has selected a collection of bio-based chemicals such as furandicarboxylic acid, 3-hydroxypropionic acid, glycerol, succinic acid, itaconic acid, xylitol, sorbitol, etc., from the initial candidate list of 300 bio-based materials, as defined as bio-based chemical base materials in the modern chemical industry.
With the rapid development of world economy and technology, the demand for energy resources has also increased greatly, and the problems of energy crisis, climate warming, environmental destruction and the like emerge, so that the effective utilization of renewable resources becomes a necessary choice for the development of the era under the background. The bio-based chemicals can get rid of the dependence on petrochemical raw materials, and the development of renewable and environment-friendly novel polymers based on the bio-based chemicals has important significance.
Itaconic acid is prepared by fermenting corn or potato starch and the like, has one double bond and two carboxyl groups in the molecular structure, can carry out addition and polymerization reactions, and can be widely used in chemical industry. Itaconic acid and its esters are also industrial materials for the production of chemical fibers, resins, plastics, rubber, pharmaceuticals, herbicides, scale removers, adhesives, surfactants, non-toxic food packaging materials, and the like.
The addition of chemicals to crude oil emulsions to break the emulsion is known as chemical breaking, and this method can be used either alone or in combination with other methods. At present, most crude oil demulsifiers used in oil fields in China are ethylene oxide propylene oxide block polyether demulsifiers. From the aspects of safety, environmental protection and technical development, the development of the novel demulsifier has important significance.
Disclosure of Invention
The invention aims to provide a bio-based demulsifier, a preparation method thereof and a treatment method of crude oil water-in-oil emulsion, wherein the polymer contained in the bio-based demulsifier is prepared from itaconic acid, dimethyl itaconate and dibutyl itaconate through free radical polymerization, and the bio-based demulsifier has a good demulsification and dehydration effect on crude oil produced liquid, can be completely degraded, and is environment-friendly.
In a first aspect the present invention provides a bio-based demulsifier comprising a polymer that is polymerized from itaconic acid, dimethyl itaconate and dibutyl itaconate;
the structural formula of the polymer comprises a structural unit shown in a formula M, N, X:
the second aspect of the present invention provides a preparation method of the bio-based demulsifier, which comprises the following steps: and (3) carrying out solution free radical polymerization on itaconic acid, dimethyl itaconate and dibutyl itaconate in the presence of an initiator and a solvent to obtain the polymer.
A third aspect of the present invention provides a method of treating a crude oil water-in-oil emulsion, the method comprising: the crude oil water-in-oil emulsion is contacted with the bio-based demulsifier described above or prepared by the preparation method described above.
The bio-based demulsifier of the invention contains itaconic acid and copolymers of esters thereof, and the polymer can be used as a crude oil water-in-oil emulsion demulsifier. Itaconic acid is an important class of bio-based chemical base stock. The wide application of the polymer formed by the itaconic acid and the derivative thereof can effectively solve the problems caused by the exhaustion of petroleum resources and environmental pollution, and has very important significance.
The invention can select polymers with different proportions to prepare corresponding demulsifiers according to different crude oil water-in-oil emulsions, and can also improve the broad-spectrum performance of the reverse demulsifier by compounding with other demulsifiers.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Detailed Description
The following describes specific embodiments of the present invention in detail. It should be understood that the detailed description and specific examples, while indicating and illustrating the invention, are not intended to limit the invention.
According to a first aspect of the present invention there is provided a bio-based demulsifier comprising a polymer that is polymerized from itaconic acid, dimethyl itaconate and dibutyl itaconate;
the structural formula of the polymer comprises a structural unit shown in a formula M, N, X:
according to the invention, M represents 0.ltoreq.m.ltoreq.30%, preferably 5.ltoreq.m.ltoreq.12% by weight of the polymer; n is 5% to 50% by weight of the polymer, preferably 30% to 50%; x is 20% or more and 95% or less, preferably 50% or less and 70% or less, by weight of the polymer.
The polymer of the present invention has the appearance of a light red to dark red viscous liquid or solid.
According to a second aspect of the present invention, there is provided a method of preparing the above bio-based demulsifier, the method comprising: and (3) carrying out solution free radical polymerization on itaconic acid, dimethyl itaconate and dibutyl itaconate in the presence of an initiator and a solvent to obtain the polymer.
In the present invention, the initiator may be an azo initiator, a peroxide initiator or a redox initiator;
preferably, the azo initiator is selected from at least one of azobisisobutyronitrile, azobisisoheptonitrile and dimethyl azobisisobutyrate.
Preferably, the peroxide initiator is benzoyl peroxide.
Preferably, the redox initiator is benzoyl peroxide-dimethylaniline.
In the invention, the dosage of the itaconic acid is 0-30 parts by weight; the dosage of the dimethyl itaconate is 5-50 parts; the dosage of the dibutyl itaconate is 20-95 parts; the initiator is used in an amount of 0.2 to 1.5 parts.
Preferably, the solvent is selected from at least one of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide and dioxane. The solvent may be used in such an amount that the solid content of the reaction system is 15 to 70wt%.
According to a preferred embodiment of the invention, the preparation method comprises the following steps:
1) Dissolving part of dimethyl itaconate, part of dibutyl itaconate and optionally part of itaconic acid in part of solvent to prepare a reaction solution;
2) Heating the reaction solution under the protection of nitrogen, and adding part of initiator to react;
3) Uniformly mixing part of dimethyl itaconate, part of dibutyl itaconate, optional part of itaconic acid, part of initiator and part of solvent, and adding the mixture into the reaction system obtained in the step 2) for reaction;
4) Uniformly mixing the rest reaction monomers, an initiator and a solvent, and adding the mixture into the reaction system obtained in the step 3) for reaction;
5) Cooling, purifying and drying the mixture obtained by the reaction in the step 4) to obtain the polymer;
preferably, the amount of the dimethyl itaconate in the step 1) is 40-85% of the total weight of the dimethyl itaconate, and the amount of the dimethyl itaconate in the step 4) is 15-60% of the total weight of the dimethyl itaconate;
the dosage of the dibutyl itaconate in the step 1) is 40-85% of the total weight of the dibutyl itaconate, and the dosage of the dibutyl itaconate in the step 4) is 15-60% of the total weight of the dibutyl itaconate;
the dosage of the itaconic acid in the step 1) is 0-50% of the total weight of the itaconic acid, and the dosage of the itaconic acid in the step 4) is 0-75% of the total weight of the itaconic acid; the amounts of itaconic acid used in step 1) and step 4) are not 0 at the same time, and the total amount of itaconic acid used in step 1) and step 4) is less than 100%;
the dosage of the solvent in the step 1) is 30-50% of the total weight of the solvent, and the dosage of the solvent in the step 3) is 20-35% of the total weight of the solvent;
the amount of the initiator in the step 2) is 20-45% of the total weight of the initiator, and the amount of the initiator in the step 3) is 15-25% of the total weight of the initiator.
According to the invention, in step 2), the temperature of the reaction solution is raised to 50-90 ℃; the reaction temperature in each step is the same as the temperature rise of the reaction solution, the reaction time in step 2) is 0.5-2h, the reaction time in step 3) is 1-4h, and the reaction time in step 4) is 2.5-6h.
According to the invention, the purification in step 5) comprises: the mixture was subjected to rotary evaporation to remove most of the solvent and unreacted monomers, precipitated with petroleum ether, and repeatedly washed with absolute ethanol or acetone.
The polymer of the invention can be discharged directly as a solution product to obtain the polymer solution.
According to a third aspect of the present invention, there is provided a method of treating a crude oil water-in-oil emulsion, the method comprising: the crude oil water-in-oil emulsion is contacted with the bio-based demulsifier described above or prepared by the preparation method described above.
In the present invention, the bio-based demulsifier may be an aqueous solution containing the above polymer, or may be a solution product prepared by the above preparation method or an aqueous solution of a prepared solid product. In general, the polymers of the invention are used in the form of solutions for the treatment of crude oil water-in-oil emulsions, the concentration of which may be from 0.5 to 30% by weight, as desired.
The polymer can be independently used for demulsifiers, and can also be used as one of the components of the demulsifiers to be matched with other demulsifiers in the prior art so as to improve the broad-spectrum performance of the demulsifiers. The existing other demulsifiers can be various polyoxyethylene polyoxypropylene ethers with different initiators or non-polyether acrylic demulsifiers, special surfactants containing silicon and phosphorus and the like.
In the present invention, the amount of bio-based demulsifier used may be the same as or different from that of the prior art. Preferably, the amount of polymer in the bio-based demulsifier is from 30 to 200mg, preferably from 50 to 150mg, relative to 1L of crude oil water-in-oil emulsion.
In the invention, the contact temperature can be 50-90 ℃, and different temperatures are selected according to the different properties of the crude oil emulsion; the contact time is 0.5 to 8 hours, preferably 1 to 6 hours.
The crude oil water-in-oil emulsion of the present invention may be an oilfield oil well produced fluid, which may have a water content of 20% to 70% by volume.
The remaining parameters not defined in the present invention may be routinely selected according to the art in the field.
The invention will be further illustrated with reference to the following examples. But are not limited by these examples.
Examples 1-3 illustrate bio-based demulsifiers according to the present invention and methods for preparing the same.
Example 1
A preparation method of a bio-based demulsifier comprises the following steps:
step 1, 2.5 g of dimethyl itaconate, 2.5 g of dibutyl itaconate and 5 g of N, N-dimethylformamide are weighed into a reactor and stirred fully until completely dissolved.
Step 2, replacing air in the reactor with nitrogen, continuously introducing nitrogen, heating to 80 ℃, and adding 0.02 g of benzoyl peroxide to start the reaction. The reaction was carried out at 80℃for 1 hour.
Step 3, weighing 0.2 g of itaconic acid, 0.5 g of dimethyl itaconate, 0.5 g of dibutyl itaconate, 0.02 g of benzoyl peroxide and 5 g of N, N-dimethylformamide, uniformly mixing, adding into a reactor, and continuously reacting for 2 hours at 80 ℃.
Step 4, weighing 0.5 g of itaconic acid, 0.05 g of benzoyl peroxide and 5 g of N, N-dimethylformamide, uniformly mixing, adding into a reactor, and continuously reacting for 3 hours at 80 ℃.
And 5, cooling, removing most of solvent and unreacted monomers from the reaction mixture by using a rotary evaporator, precipitating by using petroleum ether, repeatedly washing by using absolute ethyl alcohol, and drying to obtain red viscous liquid.
According to the added raw materials, the structural formula of the prepared polymer comprises a structural unit shown in a formula M, N, X. The content of each structural unit in the polymer is calculated according to the addition amount of the raw materials, which is a conventional expression method in the field, M accounts for 10.4 percent of the weight of the prepared polymer, N accounts for 44.8 percent of the weight of the polymer, and X accounts for 44.8 percent of the weight of the polymer.
Example 2
A preparation method of a bio-based demulsifier comprises the following steps:
step 1, 2.5 g of dimethyl itaconate, 4 g of dibutyl itaconate and 15 g of N, N-dimethylformamide are weighed into a reactor and stirred fully until completely dissolved.
Step 2, replacing air in the reactor with nitrogen, continuously introducing nitrogen, heating to 80 ℃, and adding 0.02 g of benzoyl peroxide to start the reaction. The reaction was carried out at 80℃for 1 hour.
Step 3, weighing 0.3 g of itaconic acid, 1.5 g of dimethyl itaconate, 2 g of dibutyl itaconate, 0.06 g of benzoyl peroxide and 5 g of N, N-dimethylformamide, uniformly mixing, adding into a reactor, and continuously reacting for 2 hours at 80 ℃.
Step 4, weighing 0.5 g of itaconic acid, 0.04 g of benzoyl peroxide and 5 g of N, N-dimethylformamide, uniformly mixing, adding into a reactor, and continuously reacting for 3 hours at 80 ℃.
And 5, cooling, removing most of solvent and unreacted monomers from the reaction mixture by using a rotary evaporator, precipitating by using petroleum ether, repeatedly washing by using absolute ethyl alcohol, and drying to obtain red viscous liquid.
According to the added raw materials, the structural formula of the prepared polymer comprises a structural unit shown in a formula M, N, X. The content of each structural unit in the polymer is calculated according to the addition amount of the raw materials, which is a conventional expression method in the field, M accounts for 7.4 percent of the weight of the prepared polymer, N accounts for 37 percent of the weight of the polymer, and X accounts for 55.6 percent of the weight of the polymer.
Example 3
A preparation method of a bio-based demulsifier comprises the following steps:
step 1, 2 g of itaconic acid, 1 g of dimethyl itaconate, 5 g of dibutyl itaconate and 12 g of N, N-dimethylacetamide are weighed and added into a reactor, and the mixture is fully stirred until the mixture is completely dissolved.
Step 2, replacing air in the reactor with nitrogen, continuously introducing nitrogen, heating to 50 ℃, and adding 0.1 g of benzoyl peroxide-dimethylaniline to start the reaction. The reaction was carried out at 50℃for 2 hours.
Step 3, 1 g of dimethyl itaconate, 5 g of dibutyl itaconate, 0.05 g of benzoyl peroxide-dimethylaniline and 6 g of N, N-dimethylacetamide are weighed, uniformly mixed, added into a reactor and reacted for 4 hours at 50 ℃.
Step 4, weighing 2 g of itaconic acid, 0.09 g of benzoyl peroxide-dimethylaniline and 5 g of N, N-dimethylacetamide, uniformly mixing, adding the mixture into a reactor, and continuously reacting for 4 hours at 50 ℃.
And 5, cooling, removing most of solvent and unreacted monomers from the reaction mixture by using a rotary evaporator, precipitating by using petroleum ether, repeatedly washing by using absolute ethyl alcohol, and drying to obtain a dark red solid.
According to the added raw materials, the structural formula of the prepared polymer comprises a structural unit shown in a formula M, N, X. The content of each structural unit in the polymer is calculated according to the addition amount of the raw materials, which is a conventional expression method in the field, wherein M accounts for 25 percent of the weight of the prepared polymer, N accounts for 12.5 percent of the weight of the polymer, and X accounts for 62.5 percent of the weight of the polymer.
Comparative example 1
Demulsifiers were prepared according to the method of example 1 of patent document CN102399576 a.
Comparative example 2
The demulsifier used in the solitary island oil extraction and six-united station of the victory oil field is polyether demulsifier provided by victory chemical industry.
Application examples
The polymer demulsifier prepared in example 1-3 and the demulsifier prepared in comparative example 1-2 are adopted to demulsifi the thick oil emulsion of the solitary oil extraction six-joint station of the victory oil field, and the demulsification performance of the polymer demulsifier is evaluated by an evaluation method specified by a performance detection method (bottle test method) of the crude oil demulsifier of the oil and gas industry standard SY-Y5281-2000. Crude oil with the name Chen Na oil sample containing 30% water (volume) and having an in-situ demulsification temperature of 70 ℃ and a test temperature of 85 ℃ is shown in Table 1.
TABLE 1
* : the amount of demulsifier used refers to the mass of demulsifier added per liter of oil sample.
The demulsifiers of the comparative examples 1 and 2 have good demulsification and dehydration effects on water-in-oil emulsion of the isolated island oil extraction and solitary coupling station of the victory oil field, the demulsification effect of the example 2 is obviously better than that of the comparative examples 1 and 2, and the bio-based demulsifier adopted in the examples can be completely degraded, so that the demulsifier is environment-friendly.
The foregoing description of embodiments of the invention has been presented for purposes of illustration and description, and is not intended to be exhaustive or limited to the embodiments disclosed. Many modifications and variations will be apparent to those of ordinary skill in the art without departing from the scope and spirit of the various embodiments described.
Claims (12)
1. A method for treating a crude oil water-in-oil emulsion, comprising: contacting a crude oil water-in-oil emulsion with a bio-based demulsifier;
the bio-based demulsifier comprises a polymer polymerized from itaconic acid, dimethyl itaconate and dibutyl itaconate;
the structural formula of the polymer comprises a structural unit shown in a formula M, N, X:
m accounts for 5-12% of the weight of the polymer; n accounts for 30-50% of the weight of the polymer; x accounts for 50-70% of the weight of the polymer.
2. The method for treating a crude oil water-in-oil emulsion according to claim 1, wherein the method for preparing the bio-based demulsifier comprises: in the presence of an initiator and a solvent, itaconic acid, dimethyl itaconate and dibutyl itaconate are subjected to solution free radical polymerization to prepare a polymer.
3. The method for treating a crude oil water-in-oil emulsion according to claim 2, wherein the initiator is an azo initiator, a peroxide initiator or a redox initiator.
4. The method for treating a crude oil water-in-oil emulsion according to claim 3, wherein the azo initiator is selected from at least one of azobisisobutyronitrile, azobisisoheptonitrile and dimethyl azobisisobutyrate; the peroxide initiator is benzoyl peroxide; the oxidation-reduction initiator is benzoyl peroxide-dimethylaniline.
5. The method for treating a crude oil water-in-oil emulsion according to claim 2, wherein the itaconic acid is used in an amount of 0 to 30 parts by weight; the dosage of the dimethyl itaconate is 5-50 parts; the dosage of the dibutyl itaconate is 20-95 parts; the initiator is used in an amount of 0.2 to 1.5 parts.
6. The method for treating a crude oil water-in-oil emulsion according to claim 2, wherein the solvent is at least one selected from the group consisting of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide and dioxane; the solvent is used in such an amount that the solid content of the reaction system is 15 to 70wt%.
7. The method for treating a crude oil water-in-oil emulsion according to claim 2, wherein the preparation method comprises the steps of:
1) Dissolving part of dimethyl itaconate, part of dibutyl itaconate and optionally part of itaconic acid in part of solvent to prepare a reaction solution;
2) Heating the reaction solution under the protection of nitrogen, and adding part of initiator to react;
3) Uniformly mixing part of dimethyl itaconate, part of dibutyl itaconate, optional part of itaconic acid, part of initiator and part of solvent, and adding the mixture into the reaction system obtained in the step 2) for reaction;
4) Uniformly mixing the rest reaction monomers, an initiator and a solvent, and adding the mixture into the reaction system obtained in the step 3) for reaction;
5) And (3) cooling, purifying and drying the mixture obtained by the reaction in the step (4) to obtain the polymer.
8. The method for treating a crude oil water-in-oil emulsion according to claim 7, wherein the amount of dimethyl itaconate in step 1) is 40 to 85% of the total weight of dimethyl itaconate, and the amount of dimethyl itaconate in step 4) is 15 to 60% of the total weight of dimethyl itaconate;
the dosage of the dibutyl itaconate in the step 1) is 40-85% of the total weight of the dibutyl itaconate, and the dosage of the dibutyl itaconate in the step 4) is 15-60% of the total weight of the dibutyl itaconate;
the dosage of the itaconic acid in the step 1) is 0-50% of the total weight of the itaconic acid, and the dosage of the itaconic acid in the step 4) is 0-75% of the total weight of the itaconic acid; the amounts of itaconic acid used in step 1) and step 4) are not 0 at the same time, and the total amount of itaconic acid used in step 1) and step 4) is less than 100%;
the dosage of the solvent in the step 1) is 30-50% of the total weight of the solvent, and the dosage of the solvent in the step 3) is 20-35% of the total weight of the solvent;
the amount of the initiator in the step 2) is 20-45% of the total weight of the initiator, and the amount of the initiator in the step 3) is 15-25% of the total weight of the initiator.
9. The method for treating a crude oil water-in-oil emulsion according to claim 7, wherein in step 2), the temperature of the reaction solution is raised to 50 to 90 ℃; the reaction time in step 2) is 0.5-2h, the reaction time in step 3) is 1-4h, and the reaction time in step 4) is 2.5-6h.
10. The method for treating a crude oil water-in-oil emulsion according to claim 1, wherein the contact time is 0.5 to 8 hours and the contact temperature is 50 to 90 ℃.
11. The method for treating a crude oil water-in-oil emulsion according to claim 1, wherein the amount of the polymer in the bio-based demulsifier is 30 to 200mg relative to 1 liter of the crude oil water-in-oil emulsion.
12. The method for treating a crude oil-in-water emulsion according to claim 11, wherein the amount of the polymer in the bio-based demulsifier is 50 to 150mg per 1 liter of the crude oil-in-water emulsion.
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