CN106565968B - Using propane diamine as the preparation method and application of the dissaving polymer of initiator - Google Patents
Using propane diamine as the preparation method and application of the dissaving polymer of initiator Download PDFInfo
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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
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- C08G83/005—Hyperbranched macromolecules
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- 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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- 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
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- C10G2300/1033—Oil well production fluids
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Abstract
The present invention relates to a kind of using propane diamine as the preparation method and application of the dissaving polymer of initiator, include the following steps: that 1) propane diamine is dissolved in organic solvent, then methyl acrylate is added dropwise, passes through the Michael addition reaction of 40~60h at room temperature, obtains intermediate product；2) intermediate product for obtaining step 1) is warming up to 50~150 DEG C and carries out decompression condensation reaction, obtains crude product；3) crude product for obtaining step 2) obtains the dissaving polymer using propane diamine as initiator by ether separation, revolving.The end group of the dissaving polymer is amido, containing the structures such as a large amount of amide groups in skeleton, the strongly hydrophilic of amino assigns demulsifier and quickly reaches oil-water interfaces, amide group can multiple spot be adsorbed on oil-water interfaces, play the role of destroy oil-water interfacial film, achieve the purpose that it is quick, be efficiently demulsified.
Description
Technical field
The present invention relates to petroleum additive technical fields, and in particular to a kind of using propane diamine as the hyperbranched polymerization of initiator
The preparation method and application of object.
Background technique
Daiamid quasi polymer is a kind of dendroid branched polymer (Dendritic for studying more mature
Polymer), Tomalia in 2005 et al. (Progress in Polymer Science.2005,30,294-324.) synthesis
Polyamide-amide class dendritic (being denoted as PAMAM), the quasi polymer is usually using ammonia or ethylenediamine as core, molecular weight
Highest is more than 930000g/mol, and polydispersity is less than 1.8, be macroscopically it is colourless to flaxen liquid, volatility is low,
Kinematic viscosity at 25 DEG C is 10~10000mm2/s。
Dissaving polymer is similar with dendritic (dendrimers) structure, because of its unique structure 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, which is different from dendritic (dendrimers), requires perfect structure, hyperbranched poly
It is from a wealth of sources to close raw material, generallys use " one kettle way " synthesis, simple synthetic method is easy, therefore it grinds as the field of polymers
Study carefully one of hot spot, and realizes application in fields such as nano science, biomedicine, sensor, petrochemical industry and catalyst and take
Obtain good result.
In recent years, since the application (water drive, polymer flooding, binary combination flooding, ternary composite driving) of various production techniques makes
Crude oil is obtained mostly to be plucked out of in the form of emulsion；Meanwhile salinity is very high in Produced Liquid.This is to the acquisition of crude oil, transport and adds
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
The processing or sewage treatment of liquid are played the role of vital.
Summary of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of using propane diamine as the hyperbranched poly of initiator
Close object preparation method and application, achieve the purpose that it is quick, be efficiently demulsified.
Technical solution provided by the present invention are as follows:
It is a kind of using propane diamine as the preparation method of the dissaving polymer of initiator, include the following steps:
1) propane diamine is dissolved in organic solvent, methyl acrylate is then added dropwise, at room temperature by 40~60h's
Michael addition reaction, obtains intermediate product；
2) intermediate product for obtaining step 1) is warming up to 50~150 DEG C and carries out decompression condensation reaction, obtains crude product；
3) crude product for obtaining step 2) is obtained by ether separation, revolving using propane diamine as the hyperbranched of initiator
Polymer.
In above-mentioned technical proposal, propane diamine and methyl acrylate are synthesized by " one kettle way " and obtain dissaving polymer, institute
Stating dissaving polymer center is propane diamine, and end group is amido；Its number average molecular weight distribution is 3000~10000.Compared to
Ethylenediamine is the dissaving polymer of initiator, is had using propane diamine as the dissaving polymer of initiator lower static and dynamic
State interfacial tension value can significantly reduce oil-water interfaces dynamical interfacial tension value, can not only be rapidly achieved demulsification balance, obtain
Very high demulsification efficiency, and the water deviate from is very clear, and transmissivity is very high.
Since the end group of dissaving polymer is amido, contain the structures such as a large amount of amide groups, the strong hydrophilicity of amino in skeleton
Property assign demulsifier and quickly reach oil-water interfaces, amide group can multiple spot be adsorbed on oil-water interfaces, play destruction oil-water interfaces
The effect of film, achieve the purpose that it is quick, be efficiently demulsified.
Preferably, the mass ratio of propane diamine and methyl acrylate is 3:5~9:10 in the step 1).
Preferably, the reaction time of condensation reaction is 8~10h in the step 2).
The present invention also provides it is a kind of as above-mentioned preparation method obtain using propane diamine as the dissaving polymer of initiator
Application as demulsifier.
Preferably, by it is described using propane diamine as the dissaving polymer of initiator be distributed in oil-in-water emulsion into
Row demulsification.
Preferably, the temperature of the demulsification is 30~60 DEG C, the sedimentation time is 1~30min.
Preferably, the additive amount using propane diamine as the dissaving polymer of initiator in oil-in-water emulsion
For 10~40mg/L.Additive amount is less than 10mg/L, and demulsification is bad；Additive amount is greater than 40mg/L, and demulsification variation is little,
But economic cost increases very much.
Preferably, the oil in the oil-in-water emulsion is mutually simulation oil or practical oil.
Preferably, the simulation oil is decahydronaphthalene, n-dodecane, n-tetradecane or hexadecane, the practical 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, the beneficial effects of the present invention are embodied in: using propane diamine as the dissaving polymer of initiator
End group be amido, containing structures such as a large amount of amide groups in skeleton, the strongly hydrophilic of amino assigns demulsifier and quickly reaches grease
Interface, amide group can multiple spot be adsorbed on oil-water interfaces, play the role of destroying oil-water interfacial film, reach quick, efficiently broken
The purpose of cream.
Detailed description of the invention
Fig. 1 is in embodiment 1 using propane diamine as the structural schematic diagram of the dissaving polymer (h-PAMAM) of initiator.
Specific embodiment
Following embodiment and application examples can make those skilled in the art that the present invention be more fully understood, but not limit in any way
The present invention.
Oil removal efficiency is obtained by ultraviolet specrophotometer survey calculation, and the concentration of demulsifier is added in certain temperature
With not plus the difference of the concentration of demulsifier is not divided by plus the concentration of demulsifier obtains oil removal efficiency.
Transmissivity is obtained by ultraviolet specrophotometer survey calculation, and the absorbance of demulsifier is added in certain temperature
Value with not plus the difference of the absorbance of demulsifier is not divided by plus the absorbance value of demulsifier obtains transmissivity.
Embodiment 1: it is prepared by the dissaving polymer (h-PAMAM) of initiator of propane diamine
It takes 14.2g propane diamine to be dissolved in 25mL anhydrous methanol, weighs 17.2g methyl acrylate and instill reaction system dropwise,
It is vigorously stirred room temperature reaction 48h.Reaction product carries out decompression condensation reaction to obtain the product of high polymerization degree, and temperature program is arranged
From 50 DEG C to 140 DEG C, reaction time 8h；Then, it is poured into after crude product is cooled to room temperature in 200mL ether and stirs 30min, it can
It observes that the thick liquid of pale yellow transparent is sunken to lower layer, discards upper layer ether, repeat precipitating 2 times, the lower 60 DEG C of revolvings of vacuum, i.e.,
H-PAMAM can be obtained.
It as shown in Figure 1 (needs to illustrate using propane diamine as the structural schematic diagram of the dissaving polymer (h-PAMAM) of initiator
, since dissaving structure is changeable and complicated, shown structure is merely illustrative).
Embodiment 2: it is prepared by the dissaving polymer (h-PAMAM) of initiator of propane diamine
It takes 14.8g propane diamine to be dissolved in 25mL anhydrous methanol, weighs 22.2g methyl acrylate and instill reaction system dropwise,
It is vigorously stirred room temperature reaction 60h.Reaction product carries out decompression condensation reaction to obtain the product of high polymerization degree, and temperature program is arranged
From 60 DEG C to 140 DEG C, reaction time 10h；Then, it is poured into after crude product is cooled to room temperature in 300mL ether and stirs 60min,
The thick liquid that pale yellow transparent can be observed is sunken to lower layer, discards upper layer ether, repeats precipitating 2 times, the lower 60 DEG C of revolvings of vacuum,
H-PAMAM can be 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
It mixes and is dissolved in n-dodecane as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Under 30 DEG C, 40mg/L concentration, survey
Transmissivity when the amount sedimentation time is 360min.The result shows that transmissivity of the h-PAMAM under this sedimentation time is 72%,
Compared to by the transmittance values of the modified ultra-branching polymer of initiator of ethylenediamine being 45% under equal conditions, it is 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
It mixes and is dissolved in decahydronaphthalene as oily phase, salinity is the oil-in-water emulsion of 5000mg/L.Under 30 DEG C, 40mg/L concentration,
Transmissivity when the measurement sedimentation time is 360min.The result shows that transmissivity of the h-PAMAM under this sedimentation time is
70%, compared to by the transmittance values of the modified ultra-branching polymer of initiator of ethylenediamine being 44% under equal conditions, improve
Obviously.
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
It mixes and is dissolved in n-tetradecane as oily phase, salinity is the oil-in-water emulsion of 2500mg/L.At 30 DEG C, 40mg/L concentration
Under, the transmissivity when measurement sedimentation time is 360min.The result shows that transmissivity of the h-PAMAM under this sedimentation time is
73%, compared to by the transmittance values of the modified ultra-branching polymer of initiator of ethylenediamine being 43% under equal conditions, improve
Obviously.
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
It mixes and is dissolved in hexadecane as oily phase, salinity is the oil-in-water emulsion of 7500mg/L.Survey sedimentation respectively at 45 DEG C
Oil removal efficiency when time is 1,10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in decahydronaphthalene as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Surveying the sedimentation time respectively at 45 DEG C is
1, oil removal efficiency when 10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in decahydronaphthalene as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Surveying the sedimentation time respectively at 60 DEG C is
1, oil removal efficiency when 10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in n-tetradecane as oily phase, salinity is the oil-in-water emulsion of 0mg/L.The sedimentation time is surveyed respectively at 60 DEG C
Oil removal efficiency when for 1,10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in hexadecane as oily phase, salinity is the oil-in-water emulsion of 2500mg/L.Survey sedimentation respectively at 60 DEG C
Oil removal efficiency when time is 1,10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in decahydronaphthalene as oily phase, salinity is the oil-in-water emulsion of 5000mg/L.When surveying sedimentation respectively at 60 DEG C
Between be 1,10,20 and 30min when oil removal efficiency.The result shows that oil removal efficiency 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
It mixes and is dissolved in n-dodecane as oily phase, salinity is the oil-in-water emulsion of 2500mg/L.Survey sedimentation respectively at 60 DEG C
Oil removal efficiency when time is 1,10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in decahydronaphthalene as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Surveying the sedimentation time respectively at 60 DEG C is
1, oil removal efficiency when 10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in decahydronaphthalene as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Surveying the sedimentation time respectively at 60 DEG C is
1, oil removal efficiency when 10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in aviation kerosine as oily phase, salinity is the oil-in-water emulsion of 0mg/L.The sedimentation time is surveyed respectively at 60 DEG C
Oil removal efficiency when for 1,10,20 and 30min.The result shows that oil removal efficiency 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
It mixes and is dissolved in diesel oil as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Surveyed respectively at 60 DEG C the sedimentation time be 1,
10, oil removal efficiency when 20 and 30min.The result shows that oil removal efficiency of the h-PAMAM under these sedimentation times is by 7% difference
It improves 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
It mixes and is dissolved in gasoline as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Surveyed respectively at 60 DEG C the sedimentation time be 1,
10, oil removal efficiency when 20 and 30min.The result shows that oil removal efficiency of the h-PAMAM under these sedimentation times is by 7% difference
It improves 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
It mixes and is dissolved in gasoline as oily phase, salinity is the oil-in-water emulsion of 0mg/L.Under 30 DEG C, 40mg/L concentration, measurement is heavy
Transmissivity when the drop time is 360min.The result shows that transmissivity of the h-PAMAM under this sedimentation time is 77%, compare
By the transmittance values of the modified ultra-branching polymer of initiator of ethylenediamine it is 45% under equal conditions, is obviously improved.
Illustrative description has been done to the present invention above, it is worth noting that, in the case where not departing from core of the present invention,
Any simple deformation, modification (including sedimentation time, demulsification temperature and the type of emulsion oil phase etc.) or other this fields
Technical staff can not spend the equivalent replacement of creative work to each fall within protection scope of the present invention.
Claims (6)
1. it is a kind of using propane diamine be the dissaving polymer of initiator as the application of demulsifier, which is characterized in that will it is described with
Propane diamine is distributed in oil-in-water emulsion for the dissaving polymer of initiator and is demulsified；
It is described using propane diamine as the preparation method of the dissaving polymer of initiator, include the following steps:
1) propane diamine is dissolved in organic solvent, methyl acrylate is then added dropwise, at room temperature by 40~60h's
Michael addition reaction, obtains intermediate product；The mass ratio of the propane diamine and methyl acrylate is 3:5~9:10；
2) intermediate product that step 1) obtains setting temperature program DEG C is subjected to decompression condensation reaction from 50 DEG C to 140, obtained thick
Product；The reaction time of the condensation reaction is 8~10h；
3) crude product for obtaining step 2) obtains the hyperbranched polymerization using propane diamine as initiator by ether separation, revolving
Object, the number average molecular weight distribution of the dissaving polymer are 3000~10000.
2. it is according to claim 1 using propane diamine be the dissaving polymer of initiator as the application of demulsifier, it is special
Sign is that the temperature of the demulsification is 30~60 DEG C, and the sedimentation time is 1~30min.
3. it is according to claim 1 using propane diamine be the dissaving polymer of initiator as the application of demulsifier, it is special
Sign is, it is described using propane diamine as additive amount of the dissaving polymer of initiator in oil-in-water emulsion be 10~
40mg/L。
4. it is according to claim 1 using propane diamine be the dissaving polymer of initiator as the application of demulsifier, it is special
Sign is that the oil in the oil-in-water emulsion is mutually simulation oil or practical oil.
5. it is according to claim 4 using propane diamine be the dissaving polymer of initiator as the application of demulsifier, it is special
Sign is that the simulation oil is decahydronaphthalene, n-dodecane, n-tetradecane or hexadecane, and the practical oil is kerosene, diesel oil
Or gasoline.
6. it is according to claim 1 using propane diamine be the dissaving polymer of initiator as the application of demulsifier, it is special
Sign is that 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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