CN107793531A - Acrylamido copolymer and its preparation method and application - Google Patents
Acrylamido copolymer and its preparation method and application Download PDFInfo
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Abstract
The invention belongs to oil-gas field development field, specifically provides a kind of acrylamido copolymer and preparation method and application.The acrylamido copolymer includes the construction unit A shown in formula (1), the construction unit C shown in construction unit B and formula (3) shown in formula (2), on the basis of the total mole number of construction unit in the acrylamido copolymer, the content of the construction unit A is 60 80 moles of %, the content of the construction unit B is 10 20 moles of %, and the content of the construction unit C is 5 20 moles of %；The number-average molecular weight of the acrylamido copolymer is 2,000,000 1,000 ten thousand.Relative to traditional PAM, the thickening and anti-shear ability of acrylamido copolymer of the invention increase, and the applicable target reservoir of the acrylamido copolymer is wider and has higher oil displacement efficiency.
Description
Technical field
The invention belongs to oil-gas field development field, in particular it relates to a kind of acrylamido copolymer and preparation method thereof,
And application of the acrylamido copolymer as oil displacement agent.
Background technology
Polyacrylamide (PAM) is high molecular weight water soluble polymer, is mainly used in oil exploitation, water process, papermaking, height
The fields such as water-absorbing resins, metallurgy and coal washing.In oil exploitation, PAM is mainly used in well-drilling slurry material and improved to recover the oil
Rate etc., it is widely used in the oilfield exploitation operation such as drilling well, completion, well cementation, pressure break, intensified oil reduction, there is thickening, drop filter
The functions such as mistake, rheology-modifying, gelling, shunting, section adjustment.China's oilfield exploitation has stepped into the middle and later periods at present, former to improve
Oil recovery, improve profit velocity ratio, improve production Central Plains oil content.China is due to special geological conditions, Daqing oil
Field and Shengli Oil Field have begun to widely used polymer displacement of reservoir oil tech.
Cyclodextrin (Cyclodextrin, CD) early in 1891 by Villiers first from the starch digestion liquid of amylobacter
In find, the existing history of more than 100 years so far.At present cyclodextrin used in industry be mainly α-, β-and gamma-cyclodextrin and
Its derivative, 6,7 and 8 glucose units are corresponded respectively to, wherein being most widely used especially with beta-schardinger dextrin.Cyclodextrin molecular
With the hollow cylinder three-dimensional ring structure tapered slightly, in its empty structure, outer upper end (larger open end) by C2 and
C3 secondary hydroxyl is formed, and lower end (smaller opening end) is made up of C6 primary hydroxyl, has hydrophily, and due to by C- in cavity
The shielding action of H keys forms hydrophobic region.Modified soluble cyclodextrine derivatives have stronger solubilising power, for insoluble
Spices, lipophilic agrochemicals, lipophilic drugs, organic reagent (such as trichloro ethylene, chlorobenzene, naphthalene, anthracene) have extraordinary solubilising effect
Fruit.Beta-cyclodextrin cross-linked polymer can adsorb the micropollutants (such as inorganic heavy metal ion and organic phenols, amine) in water sample.
(Zhou Yuyan, Pan Lijuan, Zheng Ying, the Xiang Shengchang such as Zhou Yuyan.The graft compound of beta cyclodextrin and polyacrylamide and
Its flocculation [J] chemical industry environmental protection to water pollutant, 2003,23 (6):362-366.) propose for water treatment agent
CD is modified PAM polymer and can prepared by way of synthesizing β-CD- P-TOLUENE SULFO ACID 99's ester intermediates, but this method causes on β-CD
All hydroxyls both participate in and react and be connected on PAM main chain, be unfavorable for controlling in modified PAM CD content and introduce new
Construction unit, CD content is higher in synthetic product (being more than 50%) and molecular weight of product wider distribution (being more than 1.5).
The content of the invention
Asked to solve existing heatproof when traditional PAM uses as oil displacement agent, salt resistance and the technologies such as anti-shearing force is poor
Topic, the invention provides the preparation method and application of a kind of acrylamido copolymer, and the acrylamido copolymer.
According to the first aspect of the invention, the invention provides a kind of acrylamido copolymer, the acrylic amide
Copolymer includes construction unit A, the construction unit C shown in construction unit B and formula (3) shown in formula (2) shown in formula (1), with
In the acrylamido copolymer on the basis of the total mole number of construction unit, the content of the construction unit A is rubbed for 60-80
You are %, and the content of the construction unit B is 10-20 moles of %, and the content of the construction unit C is 5-20 moles of %；Described third
The number-average molecular weight of acrylamide copolymer is 2,000,000-1,000 ten thousand；
According to the second aspect of the invention, should the invention provides a kind of preparation method of acrylamido copolymer
Method includes：Under the conditions of the solution polymerization of alkene, in the presence of initiator, monomer mixture is set to be polymerize in water
Reaction, the monomer mixture contain the monomer D shown in formula (4), the monomer E shown in formula (5) and the monomer F shown in formula (6), with
In the monomer mixture on the basis of the total mole number of monomer, the content of the monomer D is 60-80 moles of %, the monomer E's
Content is 10-20 moles of %, and the content of the monomer F is 5-20 moles of %；The condition of the polymerisation causes polymerisation
The number-average molecular weight of resulting polymers is 2,000,000-1,000 ten thousand afterwards；
According to the third aspect of the present invention, the invention provides acrylamido copolymer made from the preparation method.
According to the fourth aspect of the present invention, the answering as oil displacement agent the invention provides the acrylamido copolymer
With.
The present inventor it has been investigated that, because cyclodextrin carries hydrophilic molecule shell and hydrophobic intramolecular
Chamber, therefore solubility is very high in water, itself can solubilized crude oil.Relative to traditional PAM, acrylic amide of the invention is total to
The salt resistance of polymers and anti-shear ability increase, and the applicable target reservoir of the acrylamido copolymer is wider and has
Higher oil displacement efficiency.
Brief description of the drawings
Exemplary embodiment of the invention is described in more detail in conjunction with the accompanying drawings, it is of the invention above-mentioned and its
Its purpose, feature and advantage will be apparent.
Fig. 1 is the reacting flow chart that the embodiment of the present invention 1 prepares the acrylamido copolymer.
Embodiment
The embodiment of the present invention is described in detail below.It is it should be appreciated that described herein specific
Embodiment is merely to illustrate and explain the present invention, and is not intended to limit the invention.
According to the first aspect of the invention, the invention provides a kind of acrylamido copolymer, the acrylic amide
Copolymer includes construction unit A, the construction unit C shown in construction unit B and formula (3) shown in formula (2) shown in formula (1), with
In the acrylamido copolymer on the basis of the total mole number of construction unit, the content of the construction unit A is rubbed for 60-80
You are %, and the content of the construction unit B is 10-20 moles of %, and the content of the construction unit C is 5-20 moles of %；Described third
The number-average molecular weight of acrylamide copolymer is 2,000,000-1,000 ten thousand；
In formula (2),Refer to slough the group that a hydrogen is formed in the structure of beta-schardinger dextrin.Wherein,
Shown in the specific molecular structure such as formula (7) of beta-schardinger dextrin：
Selected according to the custom of this area, can also be by the structure representation of beta-schardinger dextrinSeparately
Outside, as shown in figure 1, the present invention willIt also is indicated as
The present inventor has found under study for action, is made up of the construction unit A, construction unit B and construction unit C
Oil displacement agent is made in use, fabulous oil displacement efficiency can be obtained in acrylamido copolymer.
In the present invention, corresponding monomer when the molar content of various construction units is by preparing the acrylamido copolymer
Inventory determines.
According to the second aspect of the invention, should the invention provides a kind of preparation method of acrylamido copolymer
Method includes：Under the conditions of the solution polymerization of alkene, in the presence of initiator, monomer mixture is set to be polymerize in water
Reaction, the monomer mixture contain the monomer D shown in formula (4), the monomer E shown in formula (5) and the monomer F shown in formula (6), with
In the monomer mixture on the basis of the total mole number of monomer, the content of the monomer D is 60-80 moles of %, the monomer E's
Content is 10-20 moles of %, and the content of the monomer F is 5-20 moles of %；The condition of the polymerisation causes polymerisation
The number-average molecular weight of resulting polymers is 2,000,000-1,000 ten thousand afterwards；
The method according to the invention, the weight of monomer mixture can be in interior selection in a big way, as long as ensureing that water can
Heat caused by polymerisation is fully distributed, for example, the dosage of the monomer mixture is always used with water and monomer mixture
The mass ratio of amount can be 0.05-0.5 ︰ 1.
In the method for the invention, all kinds of initiators for polymerisation in solution can be used in polymerisation, for example, azo
Class initiator, redox initiator etc..Preferably, the initiator is selected from redox initiator, the redox system
The dosage of initiator can be the 0.01-2 weight % of monomer mixture gross weight.Oxidant in the redox initiator
At least one of ammonium persulfate, potassium peroxydisulfate, sodium peroxydisulfate and hydrogen peroxide can be selected from, reducing agent can be selected from sulfurous acid
At least one of hydrogen sodium, sodium sulfite, rongalite, sodium thiosulfate, ferrous sulfate and sodium hydrosulfite.It is highly preferred that the oxygen
Agent is potassium peroxydisulfate, and the reducing agent is sodium sulfite.
The method according to the invention, the polymerisation can also be carried out in the presence of chelating agent.The chelating agent can
With selected from ethylenediamine tetra-acetic acid (EDTA) and its salt (such as EDTA-2Na).
The method according to the invention, the polymerisation are carried out in the presence of an inert gas, and the polymeric reaction condition can
With including：Temperature is 40-60 DEG C, and the time is 5-20 hours.
In the present invention, the monomer E is propylene group-beta-cyclodextrin (A- β-CD), and it, which is referred to prior art, makes bromination
Pi-allyl carries out reaction removing HBr with beta-schardinger dextrin and is made, and in one embodiment, specific steps can include：
1) at 20-35 DEG C, beta-schardinger dextrin, catalyst is made to be mixed with solvent, the mixing is carried out under agitation,
Mixing time is 0.5-1.5 hours；
2) at 40 DEG C to 60 DEG C, bromination pi-allyl is added in the solution obtained to step 1), reaction is carried out 40-60 small
When；
3) step 2) resulting solution is filtered, filter cake is washed and dried successively；
Preferably, the solvent is dimethyl sulfoxide (DMSO), and the catalyst is sodium hydroxide.
In step 2), by the reaction, yellow mercury oxide is produced；
In step 3), the filtering can be vacuum filter, and white powder is obtained by vacuum filter, can be by a large amount of
Acetone cleans to it, is then dried in vacuo, and obtains final products A- β-CD.
In aforesaid propylene group-beta-cyclodextrin preparation method, the specific dosage of each raw material can refer to prior art and be selected,
It will not be repeated here.
According to the third aspect of the present invention, the invention provides acrylic amide made from the preparation method to be copolymerized
Thing.
According to the fourth aspect of the present invention, the answering as oil displacement agent the invention provides the acrylamido copolymer
With.
As oil displacement agent in use, need to enter the copolymer according to method well known in the art according to certain degree of hydrolysis
Water-filling solution, used hydrolytic reagent are usually sodium hydroxide.There is higher oil displacement efficiency than traditional PAM.
The present invention will be described in detail by way of examples below.
Embodiment 1
The present embodiment is used to illustrate acrylamido copolymer of the present invention and preparation method thereof.Reaction process such as Fig. 1 institutes
Show.
(1) monomer E (A- β-CD) is prepared
At room temperature, 85g β-CD are dissolved in 350mL dimethyl sulfoxides (DMSO), add 15g catalyst sodium hydroxides
Afterwards, by solution magnetic agitation about 1 hour.Then at 0 DEG C, 33mL bromination pi-allyls are added dropwise in solution, 48 hours
After produce a large amount of yellow mercury oxides, then reaction solution is obtained into white powder by vacuum filter, the powder is cleaned with a large amount of acetone
End, then it is dried in vacuo at 20 DEG C, so as to which final product be made.
(2) copolymer is prepared
At ambient temperature by 17.8g acrylamides (AM), 58.8gA- β-CD and 21.4g octadecyldimethyl allyls
Ammonium chloride is dissolved in 800g distilled water and solution is moved into 2L three neck round bottom, magnetic agitation 20 minutes, then passes to lazy
Property gas is completely dissolved until reactant.After solution temperature is increased into 55 DEG C, by respectively total monomer weight 0.1wt% and
0.3wt% ethylenediamine tetra-acetic acid and initiator K2S2O8/Na2SO3(mol ratio is 1.2 ︰ 1), which is added in reaction solution, to be total to
Poly- reaction, generates transparent jelly after 5 hours, after it is cleaned into purification by liquid extraction with ethanol, and is dried in vacuo 48 at 50 DEG C
Hour, so as to which copolymer p 1 be made.
IR spectroscopic assays, in IR spectrum, 1662cm are carried out to copolymer p 1-1And 1633cm-1Place occurs belonging to acyl respectively
The amide Ⅰ absworption peak (C=O stretching vibrations) and acid amides II of amido are with absworption peak (N-H flexural vibrations), in 1020cm-1Place goes out
Existing C-N stretching vibration absworption peak；3425cm-1Locate the absworption peak for-OH occurred, 1148~1195cm-1The absworption peak at place is returned
Belong to-C-O-, in 1410cm-1There is CH on nitrogen-atoms at place3C-H flexural vibrations absworption peaks.
There is the structure shown in formula (8) as the copolymer molecule that the characteristic peak in above-mentioned IR spectrum can determine that to obtain, pass through
GPC measures its number-average molecular weight as 5,700,000.Wherein, formula (8) and x and y only represent the type of construction unit and mole contained
Amount, and do not indicate that the connected mode of construction unit.X and y concrete numerical value is determined by inventory.
Comparative example 1
Propionamides copolymer is prepared using method same as Example 1, except that, without using comonomer E,
And the addition of solution property is 44.8g, obtains acrylamido copolymer DP1, the propylene
The number-average molecular weight of acid amides analog copolymer is 5,300,000.By IR spectrum analyses, except lacking characteristic peak possessed by A- β-CD,
The appearance for going out the characteristic peak that peak position is showed with identical construction unit in P1 for the characteristic peak that its construction unit is shown
Position is similar.
Embodiment 2
The present embodiment is used to illustrate acrylamido copolymer of the present invention and preparation method thereof.
A- β-CD are prepared according to the method for embodiment 1.
At ambient temperature by 22.9g acrylamides (AM), 47g A- β-CD and 14.9g octadecyldimethyl pi-allyls
Ammonium chloride is dissolved in 800g distilled water and solution is moved into 2L three neck round bottom, magnetic agitation 20 minutes, then passes to inertia
Gas is completely dissolved until reactant.After solution temperature is increased into 55 DEG C, by respectively total monomer weight 0.3wt% and
0.3wt% ethylenediamine tetra-acetic acid and initiator K2S2O8/Na2SO3(mol ratio is 1.2 ︰ 1), which is added in reaction solution, to be total to
Poly- reaction, generates transparent jelly after 5 hours, after it is cleaned into purification by liquid extraction with ethanol, and is dried in vacuo 48 at 50 DEG C
Hour, obtain copolymer p 2.The characteristic peak shown by IR spectrum analyses, its construction unit goes out peak position and phase in P1
The appearance position for the characteristic peak that same construction unit is showed is similar.
Embodiment 3
The present embodiment is used to illustrate acrylamido copolymer of the present invention and preparation method thereof.
A- β-CD are prepared according to the method for embodiment 1.
At ambient temperature by 18.5g acrylamides, 94g A- β-CD and 22.4g octadecyldimethyl pi-allyl chlorinations
Ammonium is dissolved in 800g distilled water and solution is moved into 2L three neck round bottom, magnetic agitation 20 minutes, then passes to inert gas
Until reactant is completely dissolved.After solution temperature is increased into 55 DEG C, by respectively total monomer weight 0.3wt% and 0.5wt%
Ethylenediamine tetra-acetic acid and initiator K2S2O8/Na2SO3(mol ratio is 1.2 ︰ 1), which is added in reaction solution, carries out copolyreaction,
Transparent jelly is generated after 10 hours, after it is cleaned into purification by liquid extraction with ethanol, and is dried in vacuo 48 hours, obtains at 50 DEG C
To copolymer p 3.The characteristic peak shown by IR spectrum analyses, its construction unit goes out peak position and identical knot in P1
The appearance position for the characteristic peak that structure unit is showed is similar.
Test case
Test case is used for the oil displacement efficiency for illustrating copolymer p 1-P3 and DP1.
In order to test the oil displacement efficiency of copolymer, before test, first copolymer p 1-P3 and DP1 are hydrolyzed respectively.Specifically
Ground, copolymer is granulated respectively, according to degree of hydrolysis 30%, the sodium hydroxide grain alkali of obtained polymer billet and respective amount pinched
Splice grafting is touched, and 0.5h is hydrolyzed at 90 DEG C of temperature, after secondary granulation, the polymer after being hydrolyzed.
1st, thickening property：Under 45 DEG C of water bath conditions, the polymer configured with deionized water after the hydrolysis of various concentrations is molten
The relation of liquid, test polymer apparent viscosity and concentration, test result are as shown in table 1.
2nd, anti-shear performance：The polymer solution that aimed concn is 1500mg/L is taken, 20s is sheared for 1 grade with Rhein agitator,
The apparent viscosity before and after its polymeric shear under different salinities is determined, calculates viscosity retention ratio, the test structure such as institute of table 2
Show.
Above apparent viscosity is the 7.34s at 85 DEG C with Brookfield viscosimeters-1Under the conditions of test.
Table 1
| Polymer concentration (mg/L) | 0 | 500 | 1000 | 1500 |
| P1 viscosity (mPas) | 0 | 25.5 | 62.3 | 95.5 |
| DP2 viscosity (mPas) | 0 | 12.7 | 26.0 | 59.3 |
| P2 viscosity (mPas) | 0 | 22.2 | 60.4 | 83.2 |
| P3 viscosity (mPas) | 0 | 27.3 | 64.4 | 90.7 |
From table 1 it follows that with the increase of concentration, the viscosity of two kinds of polymer solution dramatically increases, and hydrolyzes
The P1-P3 aqueous solution viscosity be far above DP1 solution viscosity.
Table 2
| Salinity (mg/L) | 0 | 3000 | 5000 | 7000 |
| P1 viscosity retention ratios (%) | 60 | 55 | 56 | 58 |
| P2 viscosity retention ratios (%) | 62 | 57 | 59 | 60 |
| P3 viscosity retention ratios (%) | 57 | 56 | 55 | 58 |
| DP1 viscosity retention ratios (%) | 43 | 40 | 37 | 39 |
From table 2 it can be seen that in concentrated water, after the P1-P3 aqueous solution is clipped, viscosity retention ratio is maintained at
60% or so, higher than 40% or so of DP1 solution.
Therefore acrylic amide co-polymer of the invention is demonstrated by being better than the polyamide-based of unused A- β-CD modifications
Thickening and anti-shear performance, there is Oil Field application prospect.
The preferred embodiment of the present invention described in detail above, still, the present invention are not limited in above-mentioned embodiment
Detail, in the range of the technology design of the present invention, a variety of simple variants can be carried out to technical scheme, this
A little simple variants belong to protection scope of the present invention.In addition, it can also enter between a variety of embodiments of the present invention
Row any combination, as long as it without prejudice to the thought of the present invention, it should equally be considered as content disclosed in this invention.
Claims (9)
1. a kind of acrylamido copolymer, it is characterised in that the acrylamido copolymer includes the structure list shown in formula (1)
First A, the construction unit C shown in construction unit B and formula (3) shown in formula (2), with structure list in the acrylamido copolymer
On the basis of the total mole number of member, the content of the construction unit A is 60-80 moles of %, and the content of the construction unit B is 10-
20 moles of %, the construction unit C content are 5-20 moles of %；The number-average molecular weight of the acrylamido copolymer is
2000000-1,000 ten thousand；
2. a kind of preparation method of acrylamido copolymer, it is characterised in that this method includes：It is anti-in the polymerisation in solution of alkene
Under the conditions of answering, in the presence of initiator, monomer mixture is set to carry out polymerisation in water, the monomer mixture contains formula
(4) the monomer E shown in monomer D, formula (5) shown in the and monomer F shown in formula (6), with the monomer mixture monomer it is total
On the basis of molal quantity, the content of the monomer D is 60-80 moles of %, and the content of the monomer E is 10-20 moles of %, the list
Body F content is 5-20 moles of %；The condition of the polymerisation causes the number-average molecular weight of resulting polymers after polymerisation
For 2,000,000-1,000 ten thousand；
3. preparation method according to claim 2, wherein, the initiator is redox initiator, and the oxidation is also
The dosage of former initiator is the 0.01-2 weight % of monomer mixture gross weight；Oxidant choosing in the redox initiator
From at least one of ammonium persulfate, potassium peroxydisulfate, sodium peroxydisulfate and hydrogen peroxide, the reduction in the redox initiator
Agent is selected from least one of sodium hydrogensulfite, sodium sulfite, rongalite, sodium thiosulfate, ferrous sulfate and sodium hydrosulfite；It is described
The mol ratio of Oxidizing and Reducing Agents dosage is 0.5-2 ︰ 1；Preferably, the oxidant is potassium peroxydisulfate, and the reducing agent is
Sodium sulfite.
4. preparation method according to claim 2, wherein, the dosage and water and monomer mixture of the monomer mixture are total
The mass ratio of dosage is 0.05-0.5 ︰ 1.
5. preparation method according to claim 2, wherein, the polymerisation is carried out in the presence of an inert gas, described
The condition of polymerisation includes：Temperature is 40-60 DEG C, and the time is 5-20 hours.
6. preparation method according to claim 2, wherein, the monomer E is obtained by the following method：
1) at 20-35 DEG C, beta-schardinger dextrin, catalyst is made to be mixed with solvent, the mixing is carried out under agitation, stirring
Time is 0.5-1.5 hours；
2) at -5 DEG C to 10 DEG C, bromination pi-allyl is added in the solution obtained to step 1), reaction is carried out 40-60 hours；
3) step 2) resulting solution is filtered, filter cake is washed and dried successively.
7. preparation method according to claim 6, wherein, the solvent is dimethyl sulfoxide (DMSO), and the catalyst is hydrogen-oxygen
Change sodium.
8. acrylamido copolymer made from the preparation method in claim 2-7 described in any one.
9. application of the acrylamido copolymer as oil displacement agent described in claim 1 or 8.
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| CN101104665A (en) * | 2007-04-29 | 2008-01-16 | 西南石油大学 | AM/NaAA/allylcyclodextrin polymer with inclusion function and synthetic method thereof |
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| CN102746441A (en) * | 2011-04-22 | 2012-10-24 | 中国石油化工股份有限公司 | Acrylamide terpolymer and polymer and preparation method and application thereof |
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Application publication date: 20180313 |