CN112079968A - Acrylate polymer containing polyether and long carbon chain ester structure and preparation method thereof - Google Patents

Acrylate polymer containing polyether and long carbon chain ester structure and preparation method thereof Download PDF

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CN112079968A
CN112079968A CN201910516007.1A CN201910516007A CN112079968A CN 112079968 A CN112079968 A CN 112079968A CN 201910516007 A CN201910516007 A CN 201910516007A CN 112079968 A CN112079968 A CN 112079968A
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formula
monomer
polymer
initiator
demulsifier
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侯丹丹
徐伟
张天宇
许春梅
张增丽
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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Sinopec Beijing Research Institute of Chemical Industry
China Petroleum and Chemical Corp
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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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
    • 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

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Abstract

The invention provides an acrylic ester polymer containing polyether and long carbon chain ester structure, which comprises a copolymer generated by the reaction of a monomer shown in a formula A, a hydrophobic monomer and optionally acrylic acid, wherein the hydrophobic monomer has a structure shown in a formula B and a formula C,
Figure DDA0002095060900000011
R1comprising-CH2‑CH2-O-and
Figure DDA0002095060900000012
R2is C1‑C4Alkyl radical, R3Is C with side groups8An alkyl group. The polymer simultaneously contains a polyether structure and a long-chain acrylate structure with a side group, and when the polymer is used as a demulsifier, the surface activity of the demulsifier can be enhanced, the demulsification and dehydration performances of the demulsifier on crude oil-in-water emulsion, particularly high-wax crude oil emulsion, can be improved, the demulsification temperature can be reduced while the dehydration rate of the crude oil emulsion is ensured, and therefore, the purposes of energy conservation and consumption reduction are achieved.

Description

Acrylate polymer containing polyether and long carbon chain ester structure and preparation method thereof
Technical Field
The invention relates to an acrylate polymer containing polyether and long carbon chain ester structure and a preparation method thereof.
Background
Along with the continuous exploitation of crude oil, the water content of the crude oil gradually rises, and the oil-water mixed liquid gradually forms a relatively stable oil-water emulsion through an oil nozzle and a gathering and transportation pipeline, so that the emulsified crude oil needs to be demulsified and dehydrated. 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.
Demulsifiers have been studied and used for over 80 years. The molecular structure of the demulsifier is developed from the initial anionic surfactant to the block copolymer taking propylene oxide and ethylene oxide as monomers after the 40 th generation of 20 th century, and the research of the demulsifier is greatly advanced, wherein the block copolymer takes the propylene oxide and the ethylene oxide as monomers, and the conventional high-molecular nonionic surfactant, the multi-linear or three-dimensional polymer, the zwitterionic polymer, the compound thereof and the like. With the wide application of the chemical oil displacement method, the stability of the crude oil emulsion is gradually enhanced, the demulsification difficulty is increased, and the traditional polyoxyethylene polyoxypropylene block polyether demulsifier cannot meet the requirement of crude oil dehydration, so that a novel efficient crude oil demulsifier needs to be researched.
The structure of the acrylate monomer connected to the molecular skeleton of the polyether demulsifier is one of the fastest research and development directions of the recent demulsifiers, and the novel demulsifier has the advantages of high demulsification speed, high water yield and clear effluent water color, and is particularly suitable for demulsification and dehydration treatment of thick oil emulsion. The common acrylic ester monomers for copolymerization with the polyether demulsifier at present are low-carbon acrylates such as methyl acrylate, methyl methacrylate, butyl acrylate and the like. Crude oil contains waxes in addition to gums and asphaltenes. The content of wax in crude oil of different producing areas is different, the existing demulsifier has poor demulsification effect on high wax content crude oil, so that the demulsifier aiming at high wax content petroleum needs to be researched to realize effective demulsification and dehydration on high wax content crude oil emulsion.
Disclosure of Invention
The invention provides a novel acrylate polymer containing polyether and long carbon chain ester structures aiming at the characteristics of high wax content crude oil, wherein polyether with double bonds at end groups and acrylate monomers are subjected to free radical copolymerization to generate a polymer containing polyether and acrylate in a molecular structure, wherein the acrylate contains the long carbon chain ester structure, and when the polymer is used as a demulsifier, the demulsification and dehydration performances of the demulsifier on the oil-in-oil emulsion of the high wax content crude oil can be improved, the demulsification temperature is reduced while the dehydration rate of the crude oil emulsion is ensured, and the purposes of saving energy and reducing consumption are achieved.
In order to achieve the above object, according to a first aspect of the present invention, there is provided an acrylic polymer containing a polyether and a long carbon chain ester structure, comprising a copolymer produced by reacting a monomer represented by formula a with a hydrophobic monomer and optionally acrylic acid, the hydrophobic monomer having a structure represented by formula B and formula C,
Figure BDA0002095060890000021
wherein R is1Comprises that
Figure BDA0002095060890000022
R2Is C1-C4Alkyl radical, R3Is C with side groups8An alkyl group.
According to a preferred embodiment of the present invention, the monomer represented by formula A is present in an amount of 20 to 80 wt.%, based on the total mass of the monomers; and/or the content of the hydrophobic monomer is 20-80 wt%; and/or the acrylic monomer content is 0-15 wt%.
According to a preferred embodiment of the invention, the mass ratio of the hydrophobic monomer of the structure of formula B to the hydrophobic monomer of the structure of formula C is 0.5 to 5:1, for example 0.5:1, 0.6:1, 0.8:1, 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1, 5:1 and any value in between.
According to a preferred embodiment of the present invention, the polymer of the present invention contains a structural unit represented by formula a '(derived from the monomer represented by formula a), structural units represented by formula B' and formula C '(derived from the monomer represented by formula B and formula C), and a structural unit represented by formula D' (derived from the acrylic monomer).
Figure BDA0002095060890000023
Figure BDA0002095060890000031
The polymer of the present invention contains both structural units represented by the formula B 'and the formula C'. Waxes in crude oil have a variety of structures, both normal paraffins and isoparaffins with branched structures. According to the principle of similar phase solubility, a similar structure is introduced into the demulsifier molecules, which is beneficial to improving the affinity of the demulsifier molecules and crude oil, thereby improving the demulsification performance of the demulsifier. Therefore, the introduction of the long carbon chain ester unit with the structure shown in the formula C' into the copolymer can enhance the surface activity of the polymer, and when the long carbon chain ester unit is used as a demulsifier, the demulsification and dehydration performance of the demulsifier on crude oil water-in-oil emulsion, particularly high wax crude oil emulsion, can be improved.
According to a preferred embodiment of the invention, the monomer of formula C has the structure
Figure BDA0002095060890000032
2-ethylhexyl acrylate is an important acrylate monomer and is commonly used for preparing pressure-sensitive adhesive, but the application of the monomer in demulsifiers, particularly crude oil demulsification, is rarely reported. The inventor researches and discovers that the structural unit derived from 2-ethylhexyl acrylate is introduced into the polymer, so that the diffusion capacity of the demulsifier in a crude oil emulsion, particularly high-wax crude oil, can be improved, and the demulsification capacity of the demulsifier, particularly the demulsification and dehydration performance of the demulsifier on the crude oil emulsion in a low-temperature environment, can be improved. In addition, compared with other long carbon chain structure polyesters, the 2-ethylhexyl acrylate has a remarkably excellent effect when applied to highly waxy crude oil.
According to a preferred embodiment of the invention, the monomer of formula A has the structure
Figure BDA0002095060890000033
Wherein a is more than 0, b is more than 0, preferably, the number average molecular weight of the monomer shown in the formula A is more than or equal to 2000, and the hydroxyl value is 37-53 mgKOH/g.
According to another aspect of the present invention, there is provided a method for preparing the polymer by radical solution polymerization, comprising the steps of: dissolving a monomer represented by formula a, a hydrophobic monomer, and optionally acrylic acid in a solvent to obtain a mixture 1, and reacting the mixture 1 in the presence of an initiator.
Preferably, the preparation method comprises the following steps:
step S1, dissolving a first part of the monomer shown in the formula A and a first part of the hydrophobic monomer in a first part of the solvent to form a first solution, and adding a first part of the initiator into the first solution for a first time;
step S2, adding the residual monomer shown in formula A, a second part of hydrophobic monomer, a second part of solvent, optionally a first part of acrylic acid and a second part of initiator into the reaction product of step S1 for a second time;
and S3, mixing the residual hydrophobic monomer, the residual acrylic monomer, the initiator and the solvent, and adding the mixture into the reaction product obtained in the step S2 for reaction for a third time to obtain the polymer.
According to a preferred embodiment of the invention, the temperature of the reaction is between 60 and 90 ℃.
According to a preferred embodiment of the invention, the reaction is carried out in the absence of water and oxygen.
According to a preferred embodiment of the present invention, the solvent is selected from one or more of N, N-dimethylformamide, toluene, butyl ether, anisole, isopropanol, methyl ethyl ketone and ethyl acetate.
According to a preferred embodiment of the present invention, the initiator is a redox system initiator and/or an azo initiator, preferably the redox system initiator comprises benzoyl peroxide and/or benzoyl peroxide-dimethylaniline; and/or the azo initiator is selected from one or more of azobisisobutyronitrile, azobisisoheptonitrile and dimethyl azobisisobutyrate. Preferably, the initiator is used in an amount of 0.2 to 1.5% based on the total mass of the monomers.
According to a preferred embodiment of the invention, the first time is between 0.5 and 1h, and/or the second time is between 2 and 3h, and/or the third time is between 1 and 4h or more.
In the present invention, after the reaction of step S3 is completed, the following process may be performed:
optionally, step S4, removing the solvent and unreacted monomers from the reaction product of step S3, then precipitating with deionized water, and then washing and drying the resulting precipitate to obtain the product. The product is a yellowish or brownish yellow viscous liquid.
The invention also provides the application of the polymer as a demulsifier.
The polymer of the invention can be directly used as a demulsifier, or can be used as one of the components of the demulsifier to be matched with other conventional demulsifiers for use, so as to improve the performance of the demulsifier.
According to a preferred embodiment of the invention, the polymer is used as a demulsifier by contacting a water-in-oil emulsion with a demulsifier, wherein the demulsifier comprises the polymer.
According to a preferred embodiment of the invention, the demulsifier is a solution of the polymer, preferably the concentration of the polymer in the solution is from 0.5 to 30 wt%.
According to a preferred embodiment of the invention, the amount of polymer used is 30-200mg, preferably 50-150mg, for 1L of crude oil.
According to a preferred embodiment of the invention, the contact temperature is between 50 and 90 ℃ and/or the contact time is between 0.5 and 8h, preferably between 1 and 6 h.
According to a preferred embodiment of the invention, the water-in-oil emulsion contains from 20 to 70% by volume of water.
The polymer provided by the invention is prepared from polyoxyethylene polyoxypropylene ether with double bonds at the end group, a hydrophobic monomer and acrylic acid by a conventional free radical solution polymerization method, the prepared demulsifier molecule simultaneously contains two structures of polyether and acrylic ester, and the acrylic ester contains acrylic ester with a long carbon chain structure, so that the surface activity of the demulsifier can be enhanced, the demulsification and dehydration performances of the demulsifier on crude oil-in-water emulsion can be improved, the demulsification temperature can be reduced while the dehydration rate of the crude oil emulsion is ensured, and the purposes of energy conservation and consumption reduction can be achieved.
According to the physical properties of the crude oil, long-chain acrylate, such as 2-ethylhexyl acrylate, is introduced into the molecules of the demulsifier, so that the demulsification and dehydration performance of the demulsifier on crude oil water-in-oil emulsion, particularly high-wax crude oil emulsion, can be improved. The corresponding demulsifier can be prepared by selecting polymers with different proportions according to different crude oil water-in-oil emulsions, and the broad-spectrum performance of the reverse demulsifier is improved by compounding the demulsifier with other demulsifiers.
Detailed Description
The present invention will be described in detail with reference to examples, but the present invention is not limited to the examples.
The polyoxyethylene polyoxypropylene ether with double bonds at the end groups is purchased from Jiangsu Haian petrochemical plants, and the product model is polyether F6, and the structure of the polyoxyethylene polyoxypropylene ether is as follows:
Figure BDA0002095060890000051
wherein a is greater than 0, and a is greater than 0,b＞0。
example 1
Step S1, 8 g of polyoxyethylene polyoxypropylene ether (number average molecular weight is more than or equal to 2000, hydroxyl value is 45mg KOH/g), 6.4 g of butyl acrylate, 1.6 g of 2-ethylhexyl acrylate and 42 g of toluene are weighed and added into a reactor, and the mixture is fully stirred until the polyoxyethylene polyoxypropylene ether is completely dissolved.
And step S2, replacing the air in the reactor with nitrogen, continuously introducing the nitrogen, heating to 80 ℃, adding 0.096 g of benzoyl peroxide to start reaction, and reacting for 1 hour at 80 ℃.
Step S3, 6 g of polyoxyethylene polyoxypropylene ether with double bond at the end group, 3.2 g of butyl acrylate, 0.8 g of 2-ethylhexyl acrylate, 0.3 g of acrylic acid, 0.06 g of benzoyl peroxide and 37 g of toluene are weighed, mixed evenly, added into a reactor and reacted for 2 hours at 80 ℃.
Step S4, weighing 2 g butyl acrylate, 0.3 g acrylic acid, 0.1 g benzoyl peroxide and 14 g toluene, mixing evenly, adding into a reactor, and continuing to react for 4 hours at 80 ℃.
And step S5, cooling, removing most of solvent and unreacted monomers from the reaction mixture by using a rotary evaporator, precipitating by using deionized water, repeatedly washing by using absolute ethyl alcohol, and putting the mixture into a vacuum oven to be dried in vacuum at 40 ℃ to constant weight to obtain light yellow viscous liquid.
Example 2
Step S1, 3 g of polyoxyethylene polyoxypropylene ether (the number average molecular weight is more than or equal to 2000, the hydroxyl value is 45mg KOH/g), 3 g of butyl acrylate, 3 g of 2-ethylhexyl acrylate, 21 g of mixed solvent of butyl ether and anisole, wherein the end group of the polyoxyethylene polyoxypropylene ether contains double bonds, and the mixed solvent is added into a reactor and fully stirred until the polyoxyethylene polyoxypropylene ether and the butyl acrylate are completely dissolved.
And step S2, replacing the air in the reactor with nitrogen, continuously introducing the nitrogen, heating to 70 ℃, and adding 0.06 g of azobisisobutyronitrile to start the reaction. The reaction was carried out at 70 ℃ for 0.5 hour.
Step S3, weighing 1.5 g of acrylic acid, 1.5 g of 2-ethylhexyl acrylate, 0.03 g of azobisisobutyronitrile and a mixed solvent of 7.2 g of butyl ether and anisole, uniformly mixing, adding into a reactor, and continuously reacting for 1.5 hours at 70 ℃.
Step S4, weighing 2.4 g butyl acrylate, 0.6 g 2-ethylhexyl acrylate, 1.2 g acrylic acid, 0.04 g azobisisobutyronitrile and 10.8 g mixed solvent of butyl ether and anisole, mixing evenly, adding into a reactor, and continuing to react for 6 hours at 70 ℃.
And step S5, cooling, removing most of solvent and unreacted monomers from the reaction mixture by using a rotary evaporator, precipitating by using deionized water, repeatedly washing by using absolute ethyl alcohol, and putting the mixture into a vacuum oven to be dried in vacuum at 40 ℃ to constant weight to obtain light yellow viscous liquid.
Example 3
Step S1, 10 g of polyoxyethylene polyoxypropylene ether (number average molecular weight is more than or equal to 2000, hydroxyl value is 45mg KOH/g), 2 g of butyl acrylate, 3 g of 2-ethylhexyl acrylate and 28 g of N, N-dimethylformamide, wherein the terminal groups of the polyoxyethylene polyoxypropylene ether contain double bonds, are weighed and added into a reactor, and the mixture is fully stirred until the polyoxyethylene polyoxypropylene ether is completely dissolved.
And step S2, replacing the air in the reactor with nitrogen, continuously introducing the nitrogen, heating to 70 ℃, and adding 0.075 g of azobisisobutyronitrile to start the reaction. The reaction was carried out at 70 ℃ for 2 hours.
Step S3, weighing 10 g of polyoxyethylene polyoxypropylene ether with double bond at the end group, 2 g of butyl acrylate, 3 g of 2-ethylhexyl acrylate, 0.075 g of benzoyl peroxide and 30 g of toluene, uniformly mixing, adding into a reactor, raising the temperature to 80 ℃, and continuing to react for 2 hours at 80 ℃.
Step S4, weighing 0.6 g of acrylic acid, 0.09 g of benzoyl peroxide and 2 g of toluene, uniformly mixing, adding into a reactor, and continuing to react for 5.5 hours at 80 DEG C
And step S5, cooling, removing most of solvent and unreacted monomers from the reaction mixture by using a rotary evaporator, precipitating by using deionized water, repeatedly washing by using absolute ethyl alcohol, and putting the mixture into a vacuum oven to be dried in vacuum at 40 ℃ to constant weight to obtain brown yellow viscous liquid.
Comparative example 1
The demulsifier was prepared according to the method of example 1 of CN 102399576A.
Comparative example 2
The demulsifier is a polyether demulsifier which takes phenolic resin as an initiator and is provided by Shengli chemical estuary division companies. The crude oil density of the Yihe combination station is 0.9g/cm3The wax content is higher, more than 10%.
Application example 1
The compound demulsifier of the examples 1-3, the comparative examples 1-2 and the example 1 and the comparative example 2 in the weight ratio of 1:1 are respectively adopted to carry out demulsification on crude oil emulsion of a meaning and a united station of an oil extraction plant at the estuary of the Shengli oil field, the wax content of the crude oil of the meaning and the united station is higher, and the crude oil emulsion is in a solidification state at room temperature. The demulsification performance of the crude oil demulsifier is evaluated by an evaluation method specified by a service performance detection method (bottle test method) of a standard SY-Y5281-2000 crude oil demulsifier in the petroleum and natural gas industry. The demulsification temperature on site is 78 ℃, the test temperature is 8 ℃ lower than the temperature on site, and the results are shown in Table 1.
TABLE 1
Figure BDA0002095060890000071
Experiments prove that the demulsifying effect of the demulsifier prepared by the method is superior to that of the demulsifier prepared by the method disclosed by the patent CN102399576A under the condition that the actual demulsifying temperature is 8 ℃ lower than the actual demulsifying temperature on site. The demulsifying effect of example 1 on virgin oil was comparable to that of comparative example 2. The demulsifying effect of the demulsifier compounded by the embodiment 1 and the comparative example 2 is obviously better than that of other demulsifiers.
It should be noted that the above-mentioned embodiments are only for explaining the present invention, and do not constitute any limitation to the present invention. The present invention has been described with reference to exemplary embodiments, but the words which have been used herein are words of description and illustration, rather than words of limitation. The invention can be modified, as prescribed, within the scope of the claims and without departing from the scope and spirit of the invention. Although the invention has been described herein with reference to particular means, materials and embodiments, the invention is not intended to be limited to the particulars disclosed herein, but rather extends to all other methods and applications having the same functionality.

Claims (10)

1. An acrylic ester polymer containing polyether and long carbon chain ester structure comprises a copolymer generated by the reaction of a monomer shown as a formula A, a hydrophobic monomer and optionally acrylic acid, wherein the hydrophobic monomer has a structure shown as a formula B and a formula C,
Figure FDA0002095060880000011
R1comprising-CH2-CH2-O-and
Figure FDA0002095060880000012
R2is C1-C4Alkyl radical, R3Having side groups C8An alkyl group.
2. The polymer according to claim 1, wherein the monomer of formula A is present in an amount of 20 to 80 wt.%, based on the total mass of the monomers; and/or the content of the hydrophobic monomer is 20-80 wt%; and/or the acrylic monomer content is 0-15 wt%.
3. The polymer of claim 1 or 2, wherein the structure of formula C is
Figure FDA0002095060880000013
4. The polymer of any of claims 1-3, wherein the monomer of formula A has the structure
Figure FDA0002095060880000014
Wherein a is more than 0, b is more than 0, preferably, the number average molecular weight of the monomer shown in the formula A is more than or equal to 2000, and/or the hydroxyl value is 35-55 mgKOH/g.
5. A process for the preparation of a polymer as claimed in any one of claims 1 to 4 by free radical solution polymerization comprising the steps of:
dissolving a monomer shown in formula A, a hydrophobic monomer and optionally acrylic acid in a solvent to obtain a mixture 1, and reacting the mixture 1 in the presence of an initiator;
preferably, the preparation method comprises the following steps:
step S1, dissolving a first part of the monomer shown in the formula A and a first part of the hydrophobic monomer in a first part of the solvent to form a first solution, and adding a first part of the initiator into the first solution for a first time;
step S2, adding the residual monomer shown in formula A, a second part of hydrophobic monomer, a second part of solvent, optionally a first part of acrylic acid and a second part of initiator into the reaction product of step S1 for a second time;
and S3, mixing the residual hydrophobic monomer, the residual acrylic monomer, the initiator and the solvent, and adding the mixture into the reaction product obtained in the step S2 for reaction for a third time to obtain the polymer.
6. The method according to claim 5, wherein the solvent is selected from one or more of N, N-dimethylformamide, toluene, butyl ether, anisole, isopropanol, methyl ethyl ketone and ethyl acetate.
7. The method according to claim 5 or 6, characterized in that the initiator is a redox initiator and/or an azo initiator, preferably a redox initiator comprising benzoyl peroxide and/or benzoyl peroxide-dimethylaniline; and/or the azo initiator is selected from one or more of azobisisobutyronitrile, azobisisoheptonitrile and dimethyl azobisisobutyrate.
8. The method according to any of claims 5 to 7, wherein the first time is 0.5 to 2h, and/or the second time is 1 to 2h, and/or the third time is 4h or more.
9. Use of a polymer according to any one of claims 1 to 4 or produced by a process according to any one of claims 5 to 8 as a demulsifier.
10. Use according to claim 9, characterized in that a water-in-oil emulsion is contacted with the emulsion breaker, wherein the polymer is contained in the emulsion breaker.
CN201910516007.1A 2019-06-14 2019-06-14 Acrylate polymer containing polyether and long carbon chain ester structure and preparation method thereof Pending CN112079968A (en)

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
CN113201100A (en) * 2021-04-12 2021-08-03 中海油能源发展股份有限公司 In-situ demulsification functional associated polymer oil-displacing agent and preparation method thereof
CN113416575A (en) * 2021-06-23 2021-09-21 克拉玛依新科澳石油天然气技术股份有限公司 Demulsifier for dehydrating high-wax-content crude oil and preparation method thereof

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GB2174096A (en) * 1985-04-16 1986-10-29 Goldschmidt Ag Th Copolymers of polyoxyalkylene ethers and acrylic or methacrylic esters and their use as demulsifiers for petroleum containing water
CN102292359A (en) * 2009-04-28 2011-12-21 科莱恩金融(Bvi)有限公司 Use of biodegradable alkoxylated (meth)acrylate copolymers as crude oil demulsifiers
CN106811187A (en) * 2017-01-20 2017-06-09 中国石油大学(华东) Pour point depressant for crude oil and preparation method thereof

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
GB2174096A (en) * 1985-04-16 1986-10-29 Goldschmidt Ag Th Copolymers of polyoxyalkylene ethers and acrylic or methacrylic esters and their use as demulsifiers for petroleum containing water
CN102292359A (en) * 2009-04-28 2011-12-21 科莱恩金融(Bvi)有限公司 Use of biodegradable alkoxylated (meth)acrylate copolymers as crude oil demulsifiers
CN106811187A (en) * 2017-01-20 2017-06-09 中国石油大学(华东) Pour point depressant for crude oil and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113201100A (en) * 2021-04-12 2021-08-03 中海油能源发展股份有限公司 In-situ demulsification functional associated polymer oil-displacing agent and preparation method thereof
CN113416575A (en) * 2021-06-23 2021-09-21 克拉玛依新科澳石油天然气技术股份有限公司 Demulsifier for dehydrating high-wax-content crude oil and preparation method thereof

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