CN114426641A - Bio-based demulsifier, preparation method thereof and treatment method of crude oil-in-water emulsion - Google Patents
Bio-based demulsifier, preparation method thereof and treatment method of crude oil-in-water emulsion Download PDFInfo
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- CN114426641A CN114426641A CN202011081331.4A CN202011081331A CN114426641A CN 114426641 A CN114426641 A CN 114426641A CN 202011081331 A CN202011081331 A CN 202011081331A CN 114426641 A CN114426641 A CN 114426641A
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- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/14—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G33/00—Dewatering or demulsification of hydrocarbon oils
- C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
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 a crude oil-in-water emulsion. The bio-based demulsifier comprises a polymer formed by polymerizing itaconic acid, dimethyl itaconate and dibutyl itaconate; the structural formula of the polymer comprises a structural unit shown as a formula M, N, X.
Description
Technical Field
The invention belongs to the technical field of demulsifiers, and particularly relates to a bio-based demulsifier, a preparation method thereof and a treatment method of a crude oil-in-water emulsion.
Background
The bio-based chemicals are a general term for organic matters directly or indirectly obtained by photosynthesis of green plants or microorganisms, and the process is bulk or fine chemicals produced by taking biomass resources as main raw materials through means of bioengineering, chemical engineering, physical methods and the like.
As early as the early 19 th century, people were aware of how to make food, chemicals and fuels from fermentation products of bio-based raw materials, and as bio-based conversion technology developed into the 40 th century in 19 th, nearly 30% of industrial chemicals were derived from plant materials. From the initial over 300 candidate lists of bio-based feedstocks, american scientists selected a batch of bio-based chemicals such as furandicarboxylic acid, 3-hydroxypropionic acid, glycerol, succinic acid, itaconic acid, xylitol, sorbitol, etc., as defined as bio-based chemical feedstocks in the modern chemical industry.
With the rapid development of the world economy and technology, the demand for energy resources is greatly increased, the problems of energy crisis, climate warming, environmental destruction and the like emerge, and under the background, the effective utilization of renewable resources becomes the inevitable choice for the development of the times. 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 a double bond and two carboxyl groups in the molecular structure, can carry out addition and polymerization reactions, and the formed polymer can be widely used in the chemical industry. Itaconic acid and its esters are also industrial raw materials for the production of chemical fibers, resins, plastics, rubbers, pharmaceuticals, herbicides, detergents, adhesives, surfactants, non-toxic food packaging materials, and the like.
The addition of chemicals to the crude oil emulsion to break the emulsion is known as chemical demulsification and can be used either alone or in combination with other methods. The crude oil demulsifier used in oil fields in China at present is mostly ethylene oxide propylene oxide block polyether demulsifier. From the aspects of safety, environmental protection and technical development, the development of a 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 a crude oil-in-water emulsion.
The invention provides a bio-based demulsifier, which comprises a polymer polymerized by itaconic acid, dimethyl itaconate and dibutyl itaconate;
the structural formula of the polymer comprises a structural unit shown as a formula M, N, X:
the second aspect of the present invention provides a preparation method of the above bio-based demulsifier, comprising: in the presence of an initiator and a solvent, carrying out solution free radical polymerization reaction on itaconic acid, dimethyl itaconate and dibutyl itaconate to prepare the polymer.
A third aspect of the present invention provides a method of treating a crude oil-in-water emulsion, the method comprising: and contacting the crude oil-in-water emulsion with the bio-based demulsifier or the bio-based demulsifier prepared by the preparation method.
The bio-based demulsifier contains itaconic acid and ester copolymer thereof, the polymer can be used as a crude oil water-in-oil emulsion demulsifier, and the bio-based demulsifier is a degradable demulsifier completely composed of bio-based raw materials. Itaconic acid is an important bio-based chemical base material. The polymer formed by the itaconic acid and the derivatives thereof is widely applied, can effectively solve the problems caused by petroleum resource exhaustion 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 in detail specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
According to a first aspect of the invention, there is provided a bio-based demulsifier comprising a polymer polymerized from itaconic acid, dimethyl itaconate, and dibutyl itaconate;
the structural formula of the polymer comprises a structural unit shown as a formula M, N, X:
according to the invention, M is present in an amount of 0. ltoreq. m.ltoreq.30%, preferably 5% or more and 12% by weight of the polymer; n accounts for 5 percent to 50 percent of the weight of the polymer, preferably 30 percent to 50 percent; x accounts for 20 to 95 weight percent of the polymer, and preferably 50 to 70 weight percent of the polymer.
The polymers of the present invention are viscous liquids or solids ranging in appearance from light red to deep red.
According to a second aspect of the present invention, there is provided a method of preparing the above bio-based demulsifier, the method comprising: in the presence of an initiator and a solvent, carrying out solution free radical polymerization reaction on itaconic acid, dimethyl itaconate and dibutyl itaconate to prepare the polymer.
In the present invention, the initiator may be an azo initiator, a peroxide initiator or an oxidation-reduction 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 oxidation-reduction initiator is benzoyl peroxide-dimethylaniline.
In the invention, the dosage of the itaconic acid is 0-30 parts by weight; the dosage of the itaconic acid dimethyl ester is 5-50 parts; the dosage of the dibutyl itaconate is 20-95 parts; the using amount of the initiator is 0.2-1.5 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 an amount such that the solid content of the reaction system is 15 to 70% by weight.
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 optional part of itaconic acid in a part of solvent to prepare a reaction solution;
2) under the protection of nitrogen, heating the reaction solution, and adding part of initiator for reaction;
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 monomer, the initiator and the 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 dosage of the dimethyl itaconate in the step 1) is 40-85% of the total weight of the dimethyl itaconate, and the dosage 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 dosage of the itaconic acid in the step 1) and the step 4) is not 0 at the same time, and the total dosage of the itaconic acid in the step 1) and the step 4) is less than 100 percent;
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 dosage of the initiator in the step 2) is 20-45% of the total weight of the initiator, and the dosage of the initiator in the step 3) is 15-25% of the total weight of the initiator.
According to the invention, in the 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 temperature of the reaction solution, the reaction time in the step 2) is 0.5 to 2 hours, the reaction time in the step 3) is 1 to 4 hours, and the reaction time in the step 4) is 2.5 to 6 hours.
According to the invention, the purification in step 5) comprises: the mixture was subjected to rotary evaporator 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 give 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: and contacting the crude oil-in-water emulsion with the bio-based demulsifier or the bio-based demulsifier prepared by the preparation method.
In the invention, the bio-based demulsifier can be an aqueous solution containing the polymer, and also can be an aqueous solution product prepared by the 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 water-in-oil emulsions of crude oils, the concentration of the solution being from 0.5 to 30% by weight, as desired.
The polymer can be used for the demulsifier independently, and can also be used as one of the components of the demulsifier to be matched with other conventional demulsifiers for use, so that the broad-spectrum performance of the demulsifier is improved. The prior other demulsifiers can be various polyoxyethylene polyoxypropylene ethers with different initiators, or non-polyether acrylate 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 the prior art. Preferably, the amount of the polymer in the bio-based demulsifier is 30 to 200mg, preferably 50 to 150mg, relative to 1L of the crude oil-in-water emulsion.
In the invention, the contact temperature can be 50-90 ℃, and different temperatures are selected according to 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 oil well production fluid in the oil field, and may contain water in an amount of 20% to 70% by volume.
The remaining parameters not defined in the present invention can be routinely selected according to the state of the art.
The present invention will be further described with reference to the following examples. But is not limited by these examples.
Examples 1-3 are intended to illustrate the bio-based demulsifiers of the present invention and methods of making the same.
Example 1
A preparation method of a bio-based demulsifier comprises the following steps:
step 1, weighing 2.5 g of dimethyl itaconate, 2.5 g of dibutyl itaconate and 5 g of N, N-dimethylformamide into a reactor, and fully stirring until the dimethyl itaconate, dibutyl itaconate and N, N-dimethylformamide are completely dissolved.
And 2, replacing air in the reactor with nitrogen, continuously introducing the nitrogen, heating to 80 ℃, and adding 0.02 g of benzoyl peroxide to start 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 the 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 as a formula M, N, X. The content of each structural unit in the polymer was calculated from the amount of raw material added, which is also a method conventionally expressed in the art, and M accounts for 10.4% by weight, N for 44.8% by weight and X for 44.8% by weight of the polymer.
Example 2
A preparation method of a bio-based demulsifier comprises the following steps:
step 1, weighing 2.5 g of dimethyl itaconate, 4 g of dibutyl itaconate and 15 g of N, N-dimethylformamide into a reactor, and fully stirring until the dimethyl itaconate, dibutyl itaconate and N, N-dimethylformamide are completely dissolved.
And 2, replacing air in the reactor with nitrogen, continuously introducing the nitrogen, heating to 80 ℃, and adding 0.02 g of benzoyl peroxide to start 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 the 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 as a formula M, N, X. The content of each structural unit in the polymer was calculated from the amount of raw material added, which is also a method conventionally expressed in the art, and M accounts for 7.4% by weight, N for 37% by weight and X for 55.6% by weight of the polymer.
Example 3
A preparation method of a bio-based demulsifier comprises the following steps:
step 1, weighing 2 g of itaconic acid, 1 g of dimethyl itaconate, 5 g of dibutyl itaconate and 12 g of N, N-dimethylacetamide, adding into a reactor, and fully stirring until the materials are completely dissolved.
And 2, replacing air in the reactor with nitrogen, continuously introducing the 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, weighing 1 g of dimethyl itaconate, 5 g of dibutyl itaconate, 0.05 g of benzoyl peroxide-dimethylaniline and 6 g of N, N-dimethylacetamide, uniformly mixing, adding into a reactor, and continuously reacting 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 into a reactor, and continuously reacting for 4 hours at 50 ℃.
And 5, cooling, removing most of the 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 as a formula M, N, X. The content of each structural unit in the polymer was calculated from the amount of raw material added, which is also a method conventionally expressed in the art, and M accounts for 25% by weight of the polymer produced, N accounts for 12.5% by weight of the polymer, and X accounts for 62.5% by weight of the polymer.
Comparative example 1
The demulsifier was prepared according to the method of example 1 of patent document CN 102399576A.
Comparative example 2
The demulsifier is a polyether demulsifier and is provided by the victory chemical industry.
Application examples
The polymer demulsifier prepared in the embodiment 1-3 and the demulsifier prepared in the comparative example 1-2 are respectively adopted to demulsify the heavy oil emulsion in the victory oil field island oil extraction six-island combined station, and the demulsification performance of the heavy oil emulsion is evaluated by an evaluation method specified by a service performance detection method (bottle test method) of a crude oil demulsifier in the petroleum and gas industry standard SY-Y5281-2000. The oil sample is named Chennan crude oil, contains 30 percent (volume) of water, and has the field demulsification temperature of 70 ℃ and the test temperature of 85 ℃, and the results are shown in Table 1.
TABLE 1
*: the dosage of the demulsifier refers to the mass of the demulsifier added in each liter of oil sample.
The demulsifiers of the comparative examples 1 and 2 have better demulsification and dehydration effects on water-in-oil emulsions of isolated triple combination stations for oil field islands, 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 example can be completely degraded and is environment-friendly.
Having described embodiments of the present invention, the foregoing description is intended to be exemplary, not exhaustive, and not 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 described embodiments.
Claims (10)
1. The bio-based demulsifier is characterized by comprising a polymer polymerized by itaconic acid, dimethyl itaconate and dibutyl itaconate;
the structural formula of the polymer comprises a structural unit shown as a formula M, N, X:
2. the bio-based demulsifier of claim 1 wherein M comprises 0% and 30% by weight of the polymer; n accounts for 5 to 50 percent of the weight of the polymer; x accounts for 20-95% of the polymer by weight percent;
preferably, m is more than or equal to 5% and less than or equal to 12%, n is more than or equal to 30% and less than or equal to 50%, and x is more than or equal to 50% and less than or equal to 70%.
3. The method of preparing the bio-based demulsifier of claim 1 or 2, comprising: in the presence of an initiator and a solvent, carrying out solution free radical polymerization reaction on itaconic acid, dimethyl itaconate and dibutyl itaconate to prepare the polymer.
4. The method of preparing a bio-based demulsifier of claim 3 wherein the initiator is an azo initiator, a peroxide initiator, or an oxidation-reduction initiator;
preferably, 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 preparing the bio-based demulsifier according to claim 3, wherein the itaconic acid is used in an amount of 0 to 30 parts by weight; the dosage of the itaconic acid dimethyl ester is 5-50 parts; the dosage of the dibutyl itaconate is 20-95 parts; the using amount of the initiator is 0.2-1.5 parts.
6. The method of preparing the bio-based demulsifier of claim 3 wherein the solvent is selected from at least one of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide, and dioxane; the amount of the solvent used is such that the solid content of the reaction system is from 15 to 70% by weight.
7. The method of preparing a bio-based demulsifier according to claim 3 wherein the method of preparing comprises the steps of:
1) dissolving part of dimethyl itaconate, part of dibutyl itaconate and optional part of itaconic acid in a part of solvent to prepare a reaction solution;
2) under the protection of nitrogen, heating the reaction solution, and adding part of initiator for reaction;
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 monomer, the initiator and the 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 preparing the bio-based demulsifier according to claim 7, wherein the amount of dimethyl itaconate used in step 1) is 40-85% of the total weight of dimethyl itaconate, and the amount of dimethyl itaconate used in step 4) is 15-60% 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 dosage of the itaconic acid in the step 1) and the step 4) is not 0 at the same time, and the total dosage of the itaconic acid in the step 1) and the step 4) is less than 100 percent;
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 dosage of the initiator in the step 2) is 20-45% of the total weight of the initiator, and the dosage of the initiator in the step 3) is 15-25% of the total weight of the initiator.
9. The method for preparing the bio-based demulsifier according to claim 7, wherein the temperature of the reaction solution in step 2) is increased to 50 to 90 ℃; the reaction time in the step 2) is 0.5-2h, the reaction time in the step 3) is 1-4h, and the reaction time in the step 4) is 2.5-6 h.
10. A method for treating a crude oil-in-water emulsion, the method comprising: contacting a crude oil water-in-oil emulsion with the bio-based demulsifier of claim 1 or 2 or the bio-based demulsifier prepared by the preparation method of any one of claims 3-9;
preferably, the contact time is 0.5-8h, and the contact temperature is 50-90 ℃;
preferably, the amount of polymer in the bio-based demulsifier is 30 to 200mg, preferably 50 to 150mg, relative to 1L of crude oil-in-water emulsion.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110144265A1 (en) * | 2009-12-16 | 2011-06-16 | Yvon Durant | Emulsion Polymerization Of Esters Of Itaconic Acid |
| CN104204008A (en) * | 2012-02-03 | 2014-12-10 | 帝斯曼知识产权资产管理有限公司 | Polymer, process and composition |
| CN105504143A (en) * | 2014-09-26 | 2016-04-20 | 中国石油化工股份有限公司 | Non-polyether demulsifier and preparation method thereof |
| CN111718441A (en) * | 2020-06-22 | 2020-09-29 | 陕西科技大学 | Biodegradable polymer heavy oil demulsifier and preparation method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110144265A1 (en) * | 2009-12-16 | 2011-06-16 | Yvon Durant | Emulsion Polymerization Of Esters Of Itaconic Acid |
| CN104204008A (en) * | 2012-02-03 | 2014-12-10 | 帝斯曼知识产权资产管理有限公司 | Polymer, process and composition |
| CN105504143A (en) * | 2014-09-26 | 2016-04-20 | 中国石油化工股份有限公司 | Non-polyether demulsifier and preparation method thereof |
| CN111718441A (en) * | 2020-06-22 | 2020-09-29 | 陕西科技大学 | Biodegradable polymer heavy oil demulsifier and preparation method thereof |
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