CN106565968A - Preparation method and application of hyperbranched polymer with propylene diamine as initiator - Google Patents
Preparation method and application of hyperbranched polymer with propylene diamine as initiator Download PDFInfo
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- CN106565968A CN106565968A CN201610983264.2A CN201610983264A CN106565968A CN 106565968 A CN106565968 A CN 106565968A CN 201610983264 A CN201610983264 A CN 201610983264A CN 106565968 A CN106565968 A CN 106565968A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
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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
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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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1033—Oil well production fluids
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Abstract
The invention relates to a preparation method and application of a hyperbranched polymer with propylene diamine as the initiator. The preparation method includes the following steps that firstly, the promethylene diamine is dissolved in organic solvent, then, methyl acrylate is dropwise added, and an intermediate product is obtained through the Michael addition reaction lasting for 40-60 h at the room temperature; secondly, the temperature of the intermediate product obtained in the first step rises to 50-150 DEG C, the reduced pressure condensation reaction is conducted, and a rough product is obtained; and thirdly, the rough product obtained in the second step is subjected to diethyl ether separation and rotary evaporation, and the hyperbranched polymer with the propylene diamine as the initiator is obtained. The end group of the hyperbranched polymer is an amino group, a large number of amide groups and other structures are contained in the framework, a demulsifying agent can rapidly arrive at the oil-water interface due to the strong hydrophily of the amino group, the amide groups can be adsorbed to the oil-water interface in a multipoint manner, the effect of damaging an oil-water interface film is achieved, and the aim of rapid and efficient demulsifying is achieved.
Description
Technical field
The present invention relates to petroleum additive technical field, and in particular to a kind of hyperbranched polymerization with propane diamine as initiator
The preparation method and application of thing.
Background technology
Polyamide amine polymer is that a class studies to obtain more ripe dendroid branched polymer (Dendritic
Polymer), Tomalia in 2005 et al. (Progress in Polymer Science.2005,30,294-324.) synthesis
Polyamide-amide class dendritic (being designated as PAMAM), such polymer generally with ammonia or ethylenediamine as core, molecular weight
Highest is more than 930000g/mol, and polydispersity is less than 1.8, and, macroscopically for colourless to flaxen liquid, volatility is low for which,
Kinematic viscosity at 25 DEG C is 10～10000mm2/s。
Dissaving polymer is similar with dendritic (dendrimers) structure, because of its unique architectural feature, such as
Low-viscosity, high rheological variation, good dissolubility and a large amount of modifiable functional end-group etc., excite dense emerging of scientist
Interest.
But dissaving polymer requires perfect structure, hyperbranched poly different from dendritic (dendrimers)
Extensively, generally using " one kettle way " synthesis, simple synthetic method is easy, therefore it becomes field of polymer technology and grinds for compound raw material sources
Study carefully one of focus, and realize applying and taking in fields such as nano science, biomedicine, sensor, petrochemical industry and catalyst
Obtain good result.
In recent years, as the application (water drive, polymer flooding, binary combination flooding, ternary composite driving) of various production techniques makes
Obtain crude oil to be plucked out of in the form of emulsion more；Meanwhile, in Produced Liquid, salinity is very high.This gives the collection of crude oil, transports and add
Work process brings inconvenience, and corrodes Oilfield Pipelines, increases cost for oil production, and the synthesis of demulsifier and application are to oil field produced
Vital effect is played in the process or sewage disposal of liquid.
The content of the invention
Present invention aims to the deficiencies in the prior art, there is provided a kind of hyperbranched poly with propane diamine as initiator
The preparation method and application of compound, reaches the purpose of quick, efficient breakdown of emulsion.
Technical scheme provided by the present invention is：
A kind of preparation method of the dissaving polymer with propane diamine as initiator, comprises the steps：
1) propane diamine is dissolved in organic solvent, is then added dropwise over acrylic acid methyl ester., at room temperature through 40～60h's
Michael additive reaction, obtains intermediate product；
2) by step 1) intermediate product that obtains is warming up to 50～150 DEG C and carries out decompression condensation reaction, obtains crude product；
3) by step 2) crude product that obtains separated through ether, revolving, obtains hyperbranched with propane diamine as initiator
Polymer.
In above-mentioned technical proposal, propane diamine obtains dissaving polymer by " one kettle way " synthesis with acrylic acid methyl ester., institute
It is propane diamine to state dissaving polymer center, and end group is amido；Its number average molecular weight distribution is 3000～10000.Compared to
Dissaving polymer of the ethylenediamine for initiator, the dissaving polymer with propane diamine as initiator have lower static state and move
State interfacial tension value, can significantly reduce oil-water interfaces dynamical interfacial tension value, can not only be rapidly achieved breakdown of emulsion balance, obtain
Very high demulsification efficiency, and the water deviate from is very clear, and absorbance is very high.
As the end group of dissaving polymer is amido, containing the structures such as a large amount of amide groups, the strong hydrophilicity of amino in skeleton
Property give demulsifier and quickly reach oil-water interfaces, amide group can multipoint adsorption in oil-water interfaces, play destruction oil-water interfaces
The effect of film, reaches the purpose of quick, efficient breakdown of emulsion.
Preferably, the step 1) in the mass ratio of propane diamine and acrylic acid methyl ester. be 3:5～9:10.
Preferably, the step 2) in condensation reaction response time be 8～10h.
The present invention also provides the dissaving polymer with propane diamine as initiator that a kind of preparation method described above is obtained
As the application of demulsifier.
Preferably, the dissaving polymer with propane diamine as initiator is distributed in oil-in-water emulsion
Row breakdown of emulsion.
Preferably, the temperature of the breakdown of emulsion is 30～60 DEG C, the sedimentation time is 1～30min.
Preferably, addition of the dissaving polymer with propane diamine as initiator in oil-in-water emulsion
For 10～40mg/L.Addition is less than 10mg/L, and demulsification is not good；Addition is more than 40mg/L, and demulsification change is little,
But Financial cost increases a lot.
Preferably, the oil phase in the oil-in-water emulsion is simulation oil or actual oil.
Preferably, the simulation oil is decahydronaphthalene, n-dodecane, n-tetradecane or hexadecane, described actual oil
For kerosene, bavin Water Oil Or Gas.
Preferably, the salinity of the water phase in the oil-in-water emulsion is 0～10000mg/L, wherein in water phase
NaCl and CaCl2Mass ratio be 0.8～1.2.
Compared with the existing technology, beneficial effects of the present invention are embodied in：Dissaving polymer with propane diamine as initiator
End group be amido, containing the structure such as a large amount of amide groups in skeleton, the strongly hydrophilic of amino gives demulsifier and quickly reaches profit
Interface, amide group can multipoint adsorption in oil-water interfaces, play a part of to destroy oil-water interfacial film, reach quick, efficiently broken
The purpose of breast.
Description of the drawings
Structural representations of the Fig. 1 for the dissaving polymer (h-PAMAM) in embodiment 1 with propane diamine as initiator.
Specific embodiment
Following examples and application examples can make those skilled in the art be more fully understood from the present invention, but limit never in any form
The present invention.
Oil removal efficiency is obtained by ultraviolet spectrophotometer survey calculation, and the concentration of demulsifier is added in uniform temperature
With not plus demulsifier concentration difference divided by not plus the concentration of demulsifier obtains oil removal efficiency.
Absorbance is obtained by ultraviolet spectrophotometer survey calculation, and the absorbance of demulsifier is added in uniform temperature
Value with plus demulsifier absorbance difference divided by not plus the absorbance of demulsifier obtains absorbance.
Embodiment 1：It is prepared by the dissaving polymer (h-PAMAM) with propane diamine as initiator
Take 14.2g propane diamine to be dissolved in 25mL absolute methanols, weigh 17.2g acrylic acid methyl ester .s and dropwise instill reaction system,
It is stirred vigorously room temperature reaction 48h.Product carries out reducing pressure condensation reaction to obtain the product of high polymerization degree, arranges heating schedule
From 50 DEG C to 140 DEG C, the response time is 8h；Subsequently, crude product stirs 30min during 200mL ether is poured into after being cooled to room temperature, can
It was observed that the thick liquid of pale yellow transparent is sunken to lower floor, upper strata ether is discarded, repeat precipitation 2 times, lower 60 DEG C of vacuum is rotated, i.e.,
H-PAMAM is obtained.
The structural representation of the dissaving polymer (h-PAMAM) with propane diamine as initiator (needs explanation as shown in Figure 1
, as dissaving structure is changeable and complicated, shown structure is merely illustrative).
Embodiment 2：It is prepared by the dissaving polymer (h-PAMAM) with propane diamine as initiator
Take 14.8g propane diamine to be dissolved in 25mL absolute methanols, weigh 22.2g acrylic acid methyl ester .s and dropwise instill reaction system,
It is stirred vigorously room temperature reaction 60h.Product carries out reducing pressure condensation reaction to obtain the product of high polymerization degree, arranges heating schedule
From 60 DEG C to 140 DEG C, the response time is 10h；Subsequently, crude product stirs 60min during 300mL ether is poured into after being cooled to room temperature,
The thick liquid that pale yellow transparent can be observed is sunken to lower floor, discards upper strata ether, repeats precipitation 2 times, and lower 60 DEG C of vacuum is rotated,
H-PAMAM is obtained.
Application examples 1
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in n-dodecane as oil phase, oil-in-water emulsion of the salinity for 0mg/L.At 30 DEG C, under 40mg/L concentration, survey
Absorbance when the amount sedimentation time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is 72%,
Compared to the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator transmittance values be 45%, be obviously improved.
Application examples 2
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in decahydronaphthalene as oil phase, oil-in-water emulsion of the salinity for 5000mg/L.At 30 DEG C, under 40mg/L concentration,
Absorbance when the measurement sedimentation time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is
70%, compared to the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator transmittance values be 44%, improve
Substantially.
Application examples 3
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
Mix and be dissolved in n-tetradecane as oil phase, oil-in-water emulsion of the salinity for 2500mg/L.At 30 DEG C, 40mg/L concentration
Under, the absorbance when measurement sedimentation time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is
73%, compared to the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator transmittance values be 43%, improve
Substantially.
Application examples 4
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
Mix and be dissolved in hexadecane as oil phase, oil-in-water emulsion of the salinity for 7500mg/L.Survey sedimentation at 45 DEG C respectively
Oil removal efficiency when time is 1,10,20 and 30min.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
4% is respectively increased to 64%, 75%, 83% and 85%.
Application examples 5
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
Mix and be dissolved in decahydronaphthalene as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 45 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 4% point
Indescribably up to 66%, 77%, 83% and 86%.
Application examples 6
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 20mg/L
Mix and be dissolved in decahydronaphthalene as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 75%, 81%, 85% and 89%.
Application examples 7
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in n-tetradecane as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveyed the sedimentation time at 60 DEG C respectively
For 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7%
It is respectively increased to 80%, 84%, 87% and 91%.
Application examples 8
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in hexadecane as oil phase, oil-in-water emulsion of the salinity for 2500mg/L.Survey sedimentation at 60 DEG C respectively
Oil removal efficiency when time is 1,10,20 and 30min.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
7% is respectively increased to 78%, 83%, 86% and 89%.
Application examples 9
The h-PAMAM (number average molecular weight distribution is 3000～12000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in decahydronaphthalene as oil phase, oil-in-water emulsion of the salinity for 5000mg/L.When surveying sedimentation respectively at 60 DEG C
Between for 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
7% is respectively increased to 76%, 82%, 85% and 89%.
Application examples 10
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in n-dodecane as oil phase, oil-in-water emulsion of the salinity for 2500mg/L.Survey sedimentation at 60 DEG C respectively
Oil removal efficiency when time is 1,10,20 and 30min.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times by
7% is respectively increased to 78%, 84%, 86% and 90%.
Application examples 11
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 10mg/L
Mix and be dissolved in decahydronaphthalene as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 71%, 78%, 82% and 85%.
Application examples 12
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 30mg/L
Mix and be dissolved in decahydronaphthalene as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveying the sedimentation time at 60 DEG C respectively is
1st, 10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% point
Indescribably up to 78%, 82%, 86% and 89%.
Application examples 13
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in aerial kerosene as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveyed the sedimentation time at 60 DEG C respectively
For 1,10,20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7%
It is respectively increased to 81%, 85%, 87% and 90%.
Application examples 14
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in diesel oil as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveyed at 60 DEG C respectively the sedimentation time for 1,
10th, 20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% difference
Improve to 80%, 84%, 88% and 90%.
Application examples 15
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in gasoline as oil phase, oil-in-water emulsion of the salinity for 0mg/L.Surveyed at 60 DEG C respectively the sedimentation time for 1,
10th, 20 and 30min when oil removal efficiency.As a result show, oil removal efficiencies of the h-PAMAM under these sedimentation times is by 7% difference
Improve to 82%, 85%, 88% and 92%.
Application examples 16
The h-PAMAM (number average molecular weight distribution is 3000～10000) in embodiment 1 is weighed, is stirred with the concentration of 40mg/L
Mix and be dissolved in gasoline as oil phase, oil-in-water emulsion of the salinity for 0mg/L.At 30 DEG C, under 40mg/L concentration, measurement is heavy
Absorbance when the drop time is 360min.As a result show, absorbancies of the h-PAMAM under this sedimentation time is 77%, is compared
The transmittance values of the modified ultra-branching polymer under equal conditions with ethylenediamine as initiator are 45%, are obviously improved.
Do exemplary description above to the present invention, what deserves to be explained is, in the case of without departing from core of the present invention,
Any simple deformation, modification (including species of sedimentation time, breakdown of emulsion temperature and emulsion oil phase etc.) or other this areas
Technical staff can not spend the equivalent of creative work to each fall within protection scope of the present invention.
Claims (10)
1. a kind of preparation method of the dissaving polymer with propane diamine as initiator, it is characterised in that comprise the steps：
1) propane diamine is dissolved in organic solvent, is then added dropwise over acrylic acid methyl ester., at room temperature through 40～60h's
Michael additive reaction, obtains intermediate product；
2) by step 1) intermediate product that obtains is warming up to 50～150 DEG C and carries out decompression condensation reaction, obtains crude product；
3) by step 2) crude product that obtains separated through ether, revolving, obtains the hyperbranched polymerization with propane diamine as initiator
Thing.
2. the preparation method of the dissaving polymer with propane diamine as initiator according to claim 1, it is characterised in that
The step 1) in the mass ratio of propane diamine and acrylic acid methyl ester. be 3:5～9:10.
3. the preparation method of the dissaving polymer with propane diamine as initiator according to claim 1, it is characterised in that
The step 2) in condensation reaction response time be 8～10h.
4. the hyperbranched polymerization with propane diamine as initiator that a kind of preparation method as described in claims 1 to 3 is arbitrary is obtained
Application of the thing as demulsifier.
5. application of the dissaving polymer using propane diamine as initiator according to claim 4 as demulsifier, which is special
Levy and be, the dissaving polymer with propane diamine as initiator is distributed in oil-in-water emulsion carries out breakdown of emulsion.
6. application of the dissaving polymer using propane diamine as initiator according to claim 5 as demulsifier, which is special
Levy and be, the temperature of the breakdown of emulsion is 30～60 DEG C, and the sedimentation time is 1～30min.
7. application of the dissaving polymer using propane diamine as initiator according to claim 5 as demulsifier, which is special
Levy and be, addition of the dissaving polymer with propane diamine as initiator in oil-in-water emulsion be 10～
40mg/L。
8. application of the dissaving polymer using propane diamine as initiator according to claim 5 as demulsifier, which is special
Levy and be, the oil phase in the oil-in-water emulsion is simulation oil or actual oil.
9. application of the dissaving polymer using propane diamine as initiator according to claim 8 as demulsifier, which is special
Levy and be, the simulation oil is decahydronaphthalene, n-dodecane, n-tetradecane or hexadecane, and described actual oil is kerosene, diesel oil
Or gasoline.
10. application of the dissaving polymer using propane diamine as initiator according to claim 5 as demulsifier, which is special
Levy and be, the salinity of the water phase in the oil-in-water emulsion is 0～10000mg/L, wherein NaCl and CaCl in water phase2
Mass ratio be 0.8～1.2.
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| CN109370635A (en) * | 2018-10-19 | 2019-02-22 | 浙江大学 | The method that a kind of pair of oil-in-water emulsion is demulsified |
| CN111019127A (en) * | 2019-12-24 | 2020-04-17 | 中海油天津化工研究设计院有限公司 | Modified hyperbranched polyamidoamine polymer and preparation method thereof |
| CN111732735A (en) * | 2020-06-11 | 2020-10-02 | 长江大学 | Hyperbranched polymer-SiO2Composite demulsifier and preparation method and application thereof |
| CN116178708A (en) * | 2022-12-20 | 2023-05-30 | 山东秋水化学科技有限公司 | Preparation method of composite antioxidant |
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| CN106565968B (en) | 2019-10-15 |
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