CN107118756B - A kind of efficient thick-oil thinner and preparation method thereof - Google Patents
A kind of efficient thick-oil thinner and preparation method thereof Download PDFInfo
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- CN107118756B CN107118756B CN201710463257.4A CN201710463257A CN107118756B CN 107118756 B CN107118756 B CN 107118756B CN 201710463257 A CN201710463257 A CN 201710463257A CN 107118756 B CN107118756 B CN 107118756B
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/588—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific polymers
Abstract
The invention discloses a kind of efficient thick-oil thinners and preparation method thereof.Heavy crude thinner provided by the present invention is made of two kinds of effective ingredients.Effective ingredient I is humic acid condensation polymer (HA)n, effective ingredient II is polydiene propyl alkyl ammonium chloride (PDAC).The efficient thick-oil thinner in 40 DEG C, 60 DEG C and 80 DEG C viscosity break ratios up to 80% or more, especially (HA)n(n=25) with PDAC (x=15, y=7, m is about mass ratio 500) when being 5:5, it is respectively 91.27% in 40 DEG C, 60 DEG C and 80 DEG C viscosity break ratios, 96.73% and 98.55%, illustrate under the conditions of higher temperature and salinity, heavy crude thinner of the invention has good reducing thick oil viscosity performance.
Description
Technical field
The invention belongs to Petroleum Processing Technology fields, and in particular to a kind of efficient thick-oil thinner and preparation method thereof.
Background technique
With the reduction of light oil recoverable reserves and the raising of oil exploitation technology, specific gravity shared by viscous crude constantly increases
Greatly.Viscous crude is that mainly have that viscosity is big, grease density contrast is small, mobility is poor rich in there is the complex mixture of asphalitine, colloid
The features such as.Colloid, asphalitine in viscous crude inherently have surface-active, when mixing with water flooding, easily because emulsification is led
Cause the raising of viscosity of thickened oil.Therefore, reducing thick oil viscosity is link indispensable in the production of oil field.
Chemical viscosity reduction technology is one of measure maximum to reducing thick oil viscosity amplitude at present and the most economic, and in each viscous crude
It is widely used in oil field.The effects of chemical viscosity reduction agent can be effectively disperseed, emulsify for viscous crude, significant decrease viscosity of thickened oil,
Reduce viscous crude flow resistance in stratum and pit shaft, this is adopted for reducing recovery process energy consumption, reduction exhaust emission, improving viscous crude
Yield is of great significance.
Humic acid (HA) is product of the natural plant residuum after rotting to decompose, and is that a kind of natural macromolecular of complexity has
Machine matter, shown in structural formula such as formula (a).
Its intramolecular contains the various actives such as carbonyl, carboxyl, alcoholic extract hydroxyl group and phenolic hydroxyl group functional group, makes it have acid, parent
Aqueous, interfacial activity, cation exchange capacity (CEC), complexing and absorption dispersibility, thus humic acid substance is in environmental protection, stone
Fields such as oily exploitation, agricultural gardening, medicine, analytical chemistry, battery industry etc. all have a wide range of applications.
Summary of the invention
The object of the present invention is to provide a kind of heavy crude thinners and preparation method thereof.
Heavy crude thinner provided by the present invention, is made of effective component and solvent, wherein the quality percentage of effective component
Content is 40%-60%.
The effective component is made of two kinds of compositions, and composition I is humic acid condensation polymer (HA)n, structural formula such as formula (b) institute
Show:
In formula (b), HA indicates humic acid, shown in structural formula such as formula (a):
Humic acid is a kind of mixture of unformed macromolecular of complexity, and the humic acid of separate sources also has very in structure
Big difference, so there are no an accurate unified conclusions for structure of the people to humic acid, currently, in the world to HA two-dimensional structure
Model is it is generally accepted that Stevenson structural model, as shown in formula (b).
In formula (b), n is condensation degree, value range 2~100, concretely 25-75,25-50,50-75,25,50 or 75；
Composition II is polydiene propyl alkyl ammonium chloride (PDAC), shown in structural formula such as formula (c):
In formula (c), R1ForAlkyl structure, wherein x is the integer of 0-15, R2ForAlkyl structure,
Y is the integer of 0-7, such as works as x=0, when y=0, i.e. R1、R2It is methyl；M is the degree of polymerization, and range is 5~1000, specifically may be used
For 100-800,200-800 or 500.
The solvent can be one or more of water, methanol and ethyl alcohol.
In above-mentioned thinner, humic acid condensation polymer (HA)nAccount for the 30%-50% of effective ingredient gross mass, polydiene propyl
Alkyl ammomium chloride (PDAC) accounts for the 50%-70% of effective ingredient gross mass.
In above-mentioned thinner, the humic acid condensation polymer (HA)nIt is total with polydiene propyl dialkylammonium chloride (PDAC)
The mass ratio of quality and the solvent concretely 1:1.
In above-mentioned thinner, the humic acid condensation polymer (HA)nWith the matter of polydiene propyl dialkylammonium chloride (PDAC)
Measuring score ratio can be (3-5): (5-7), concretely 3:7,4:6 or 5:5.
Above-mentioned humic acid condensation polymer (HA)nIt is that method as steps described below is prepared: with triphenyl phosphorus (PPh3) and
Diethyl azodiformate (DEAD) is catalyst, under concentrated sulfuric acid effect, so that polycondensation reaction occurs for humic acid, obtains formula
(b) humic acid condensation polymer (HA) shown inn。
The temperature of the polycondensation reaction is 50-180 DEG C, and the time is 3-10 hours.
Above-mentioned polydiene propyl alkyl ammonium chloride (PDAC) is that method as steps described below is prepared:
(1) make diallylamine and alkyl halide (R1- X, wherein R1For-(CH2)XCH3Alkyl structure, wherein x is the whole of 0-15
Number, X are chlorine, bromine or iodine) reaction, obtain product M；
(2) make product M and alkyl halide (R2- X, wherein R2For-(CH2)yCH3Alkyl structure, y be 0-7 integer, X be chlorine,
Bromine or iodine) reaction, obtain product N；
(3) it polymerize product N, obtains polydiene propyl alkyl ammonium chloride (PDAC).
In above method step (1), diallylamine and alkyl halide R1The molar ratio of-X is 1:0.5-1.
The temperature of the reaction is 30-45 DEG C, and the time is 72-168 hours.
In above method step (2), product M and alkyl halide R2The molar ratio of-X is 1:1-3.
The temperature of the reaction is 30-45 DEG C, and the time is 120-336 hours.
In above method step (3), the temperature of the polymerization is 50-80 DEG C, and the time is 3-6 hours.
Above-mentioned heavy crude thinner can be prepared by the method included the following steps: by humic acid condensation polymer (HA)n, it is poly-
Poly (dially dialkyl) ammonium chloride (PDAC) and solvent are uniformly mixed up to the heavy crude thinner.
Application of the above-mentioned heavy crude thinner in thickened oil recovery also belongs to protection scope of the present invention.
Above-mentioned structure feature makes efficient thick-oil thinner of the invention have good interface participation ability and viscosity reduction
Effect partially breaks plane overlapping heap by entering between resin and asphalt sheet molecule by strong infiltration, peptizaiton
Aggregation made of block, form colloid, asphaltene molecules and visbreaking agent molecule be collectively formed it is random pile up, structure it is more open
Aggregation, to reduce Viscosity of Heavy Crude Oil.
Experimental data show above-mentioned efficient thick-oil thinner in 40 DEG C, 60 DEG C and 80 DEG C viscosity break ratios up to 80% or more, especially
It is (HA)n(n=25) with PDAC (x=15, y=7, m are about mass ratio 500) be 5:5 when, at 40 DEG C, 60 DEG C and 80
DEG C viscosity break ratio is respectively 91.27%, 96.73% and 98.55%, is illustrated under the conditions of higher temperature and salinity, of the invention
Heavy crude thinner has good reducing thick oil viscosity performance.
Specific embodiment
The present invention will be described below by way of specific embodiments, but the present invention is not limited thereto.
Experimental method used in following embodiments is conventional method unless otherwise specified；Institute in following embodiments
Reagent, material etc., are commercially available unless otherwise specified.
Effective component I humic acid condensation polymer (HA) in the present inventionnIt is prepared by the following method: by humic acid, three
Phenyl phosphorus (PPh3) and diethyl azodiformate (DEAD) be added in the water segregator containing a certain amount of toluene, reflux point
Water is slowly dropped into the concentrated sulfuric acid by constant pressure funnel, after 180 ± 5 DEG C, reaction 3 hours are warming up to after stirring 1 hour at 60 DEG C
It terminates.Filtering is washed, and is separated, recrystallization, the polymer (HA) after being condensedn, condensation degree is 2~100.
II polydiene propyl alkyl ammonium chloride (PDAC) of effective component in the present invention is prepared by the following method:
(1) by diallylamine and idoalkane (R1- I) it is mixed with the ratio of molar ratio 1:1, it is dissolved in 100mL acetone, and
0.5% hydroquinone of idoalkane quality is added, after being stirred 24 hours under conditions of 40 degree, be slowly added dropwise with idoalkane etc.
The chloroformic solution for the triethylamine that molal quantity and mass fraction are 30%, the reaction was continued 72 hours, after removing part acetone under reduced pressure, to
Excessive ether is added in reaction solution solid is precipitated, filters off solid, solvent is evaporated off after obtaining filtrate, is washed repeatedly with ether 3 times, receives
Collect filtrate, evaporating solvent under reduced pressure obtains product (M).
(2) by back product (M) and bromoalkane (R2- Br) it is mixed with the ratio of molar ratio 1:4, it is dissolved in 100mL acetone
In, and the hydroquinone of 4% KI and 0.5% of bromoalkane quality is added, it is stirred 96 hours under conditions of 40 degree, decompression is steamed
After part acetone, excessive ether is added into reaction solution, solid is precipitated, with the mixed solvent volume ratio of acetone/diethyl ether (3:
7) it recrystallizes 3 times repeatedly, obtains product (N).
(3) a certain amount of product (N) is added in the reaction vessel to be dissolved in 200mL deionized water, ice bath is simultaneously passed through nitrogen
30min or more is polymerize (oxidant and reducing agent with redox initiation system ammonium persulfate and iron ammonium sulfate to it
Mass ratio is respectively 1.2:1,1.5:1,2:1), product polydiene propyl alkyl ammonium chloride (PDAC) is filtered to obtain in dialysis.
The humic acid condensation polymer and polydiene propyl alkyl ammonium chloride are dissolved in water, it is molten to be configured to polymer
Liquid, then 1:1 ratio mixes in mass ratio therebetween, carries out the test of performance index screening.
Thinner of the present invention is a kind of to mix humic acid condensation polymer in a solvent with polydiene propyl alkyl ammonium chloride
Compound system.Each composition proportion has a certain impact to viscosity-reducing performance.
Specific preparation step is as follows:
The preparation of embodiment 1, new type compound heavy crude thinner A
By the humic acid of 24.16g, 5.4g triphenyl phosphorus (PPh3) and 2.173g diethyl azodiformate (DEAD) addition
Into the water segregator containing 100mL toluene, reflux water-dividing is slowly included in the concentrated sulfuric acid, total 30mL, 60 by constant pressure funnel
DEG C 180 ± 5 DEG C are warming up to after stirring 1 hour, reaction terminates after 3 hours.Filtering is washed, and is separated, and recrystallization obtains condensation degree
For 25 (HA)n。
30g effective component I humic acid condensation polymer (HA)n(n=25), 70g polydiene propyl alkyl ammonium chloride (PDAC) (x
=15, y=7, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 3:7, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 2, new type compound heavy crude thinner B
By the humic acid of 24.16g, 5.4g triphenyl phosphorus (PPh3) and 2.173g diethyl azodiformate (DEAD) addition
Into the water segregator containing 100mL toluene, reflux water-dividing is slowly included in the concentrated sulfuric acid, total 30mL, 60 by constant pressure funnel
DEG C 180 ± 5 DEG C are warming up to after stirring 1 hour, reaction terminates after 3 hours.Filtering is washed, and is separated, and recrystallization obtains condensation degree
For 25 (HA)n。
The condensation polymer (HA) of 40g effective component I humic acidn(n=25), 60g polydiene propyl alkyl ammonium chloride (PDAC)
(x=15, y=7, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 4:6, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 3, new type compound heavy crude thinner C
By the humic acid of 24.16g, 5.4g triphenyl phosphorus (PPh3) and 2.173g diethyl azodiformate (DEAD) addition
Into the water segregator containing 100mL toluene, reflux water-dividing is slowly included in the concentrated sulfuric acid, total 30mL, 60 by constant pressure funnel
DEG C 180 ± 5 DEG C are warming up to after stirring 1 hour, reaction terminates after 3 hours.Filtering is washed, and is separated, and recrystallization obtains condensation degree
For 25 (HA)n。
The condensation polymer (HA) of 50g effective component I humic acidn(n=25), 50g polydiene propyl alkyl ammonium chloride (PDAC)
(x=15, y=7, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 5:5, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 4, new type compound heavy crude thinner D
By the humic acid of 30.16g, 1.3g triphenyl phosphorus (PPh3) and 4.773g diethyl azodiformate (DEAD) addition
Into the water segregator containing 100mL toluene, reflux water-dividing is slowly included in the concentrated sulfuric acid, total 30mL, 60 by constant pressure funnel
DEG C 180 ± 5 DEG C are warming up to after stirring 1 hour, reaction terminates after 3 hours.Filtering is washed, and is separated, and recrystallization obtains condensation degree
For 50 (HA)n。
The condensation polymer (HA) of 50g effective component I humic acidn(n=50), 50g polydiene propyl alkyl ammonium chloride (PDAC)
(x=7, y=0, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 5:5, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 5, new type compound heavy crude thinner E
By the humic acid of 30.16g, 1.3g triphenyl phosphorus (PPh3) and 4.773g diethyl azodiformate (DEAD) addition
Into the water segregator containing 100mL toluene, reflux water-dividing is slowly included in the concentrated sulfuric acid, total 30mL, 60 by constant pressure funnel
DEG C 180 ± 5 DEG C are warming up to after stirring 1 hour, reaction terminates after 3 hours.Filtering is washed, and is separated, and recrystallization obtains condensation degree
For 50 (HA)n。
The condensation polymer (HA) of 50g effective component I humic acidn(n=50), 50g polydiene propyl alkyl ammonium chloride (PDAC)
(x=7, y=7, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 5:5, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 6, new type compound heavy crude thinner F
By the humic acid of 30.16g, 1.3g triphenyl phosphorus (PPh3) and 4.773g diethyl azodiformate (DEAD) addition
Into the water segregator containing 100mL toluene, reflux water-dividing is slowly dropped into the concentrated sulfuric acid, total 30mL, 60 by constant pressure funnel
DEG C 180 ± 5 DEG C are warming up to after stirring 1 hour, reaction terminates after 3 hours.Filtering is washed, and is separated, and recrystallization obtains condensation degree
For 50 (HA)n。
The condensation polymer (HA) of 50g effective component I humic acidn(n=50), 50g polydiene propyl alkyl ammonium chloride (PDAC)
(x=11, y=7, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 5:5, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 7, new type compound heavy crude thinner G
By the humic acid of 38.261g, 5.71g triphenyl phosphorus (PPh3) and 8.682g diethyl azodiformate (DEAD) plus
Enter into the water segregator containing 200mL toluene, reflux water-dividing, the concentrated sulfuric acid is slowly included in by constant pressure funnel, total 30mL,
60 DEG C are warming up to 180 ± 5 DEG C after stirring 1 hour, and reaction terminates after 5 hours.Filtering is washed, and is separated, and recrystallization is condensed
(HA) that degree is 75n。
The condensation polymer (HA) of 50g effective component I humic acidn(n=75), 50g polydiene propyl alkyl ammonium chloride (PDAC)
(x=7, y=0, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 5:5, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 8, new type compound heavy crude thinner H
By the humic acid of 38.261g, 5.71g triphenyl phosphorus (PPh3) and 8.682g diethyl azodiformate (DEAD) plus
Enter into the water segregator containing 200mL toluene, reflux water-dividing, the concentrated sulfuric acid is slowly included in by constant pressure funnel, total 30mL,
60 DEG C are warming up to 180 ± 5 DEG C after stirring 1 hour, and reaction terminates after 5 hours.Filtering is washed, and is separated, and recrystallization is condensed
(HA) that degree is 75n。
The condensation polymer (HA) of 50g effective component I humic acidn(n=75), 50g polydiene propyl alkyl ammonium chloride (PDAC)
(x=7, y=7, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 5:5, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
The preparation of embodiment 9, new type compound heavy crude thinner I
By the humic acid of 38.261g, 5.71g triphenyl phosphorus (PPh3) and 8.682g diethyl azodiformate (DEAD) plus
Enter into the water segregator containing 200mL toluene, reflux water-dividing, the concentrated sulfuric acid is slowly included in by constant pressure funnel, total 30mL,
60 DEG C are warming up to 180 ± 5 DEG C after stirring 1 hour, and reaction terminates after 5 hours.Filtering is washed, and is separated, and recrystallization is condensed
(HA) that degree is 75n。
The condensation polymer (HA) of 50g effective component I humic acidn(n=75), 50g polydiene propyl alkyl ammonium chloride (PDAC)
(x=11, y=7, m are about 500) to be uniformly mixed with 100g ethyl alcohol, obtain a kind of efficient thick-oil thinner, are labeled as A, wherein
(HA)nMass ratio with PDAC is 5:5, (HA)nIt is 1:1 with the gross mass of PDAC and the mass ratio of ethyl alcohol.
Embodiment 10, embodiment 1-9 compound heavy crude thinner A, B, C, D, E, F, G, H and I viscosity reducing effect experiment
Bottle is carried out to sample viscous crude and tries method viscosity reduction, viscosity of thickened oil is 11000mPas at 30 DEG C.Experimental result such as table 1 to
Shown in table 3.
Specific experiment step are as follows:
Heavy crude thinner (A-I) prepared by embodiment 1-9 uses salinity 3 × 104The salt water of mg/L is formulated as respectively
This heavy crude thinner is added separately to the tool equipped with 50mL dehydration degassing viscous crude sample by the reducing thick oil viscosity agent solution of various concentration
It fills in test tube, thinner dosage is 1200mg/L, and solution and viscous crude sample volume ratio are 1:1.After covering tightly test tube plug, test tube is put
It sets in oscillation case, horizontal oscillations 80-100 times, amplitude should be greater than 20cm.After being sufficiently mixed, respectively at 40 DEG C, 60 DEG C, 80 DEG C
Lower viscosity (the shear rate 7.34s using Brookfield viscosity meter mixed system-1).Reducing thick oil viscosity result such as table 1
To shown in table 3.
To the viscosity reduction experimental result of sample viscous crude at 40 DEG C of heavy crude thinner of 1 embodiment 1-9 of table
To the viscosity reduction experimental result of sample viscous crude at 60 DEG C of heavy crude thinner of 2 embodiment 1-9 of table
To the viscosity reduction experimental result of sample viscous crude at 80 DEG C of heavy crude thinner of 3 embodiment 1-9 of table
The above result shows that heavy crude thinner of the invention has preferable viscosity-reducing performance for viscous crude, at 40 DEG C, 60 DEG C
It is respectively 91.27% in 40 DEG C, 60 DEG C and 80 DEG C viscosity break ratios with 80 DEG C of viscosity break ratios up to 80% or more, especially thinner C,
96.73% and 98.55%, show good viscosity reduction ability.
Claims (4)
1. a kind of heavy crude thinner, is made of effective component and solvent, wherein effective component is made of two kinds of compositions, and composition I is
Humic acid condensation polymer,
The humic acid condensation polymer is to be prepared as follows to obtain: being catalysis with triphenyl phosphorus and diethyl azodiformate
Agent, so that polycondensation reaction occurs for humic acid, obtains humic acid condensation polymer under concentrated sulfuric acid effect；
The temperature of the polycondensation reaction is 50-180 DEG C, and the time is 3-10 hours；
Composition II is polydiene propyl alkyl ammonium chloride, shown in structural formula such as formula (c):
In formula (c), R1ForAlkyl structure, wherein x is the integer of 0-15, R2ForAlkyl structure, y are
The integer of 0-7；M is the degree of polymerization, m=200-800；
The solvent is one or more of water, methanol and ethyl alcohol.
2. heavy crude thinner according to claim 1, it is characterised in that: in the thinner, the quality hundred of effective component
Dividing content is 40%-60%；
Humic acid condensation polymer accounts for the 30%-50% of effective ingredient gross mass, and it is total that polydiene propyl alkyl ammonium chloride accounts for effective ingredient
The 50%-70% of quality.
3. the method for preparing heavy crude thinner described in claims 1 or 2, comprising:
The humic acid condensation polymer, polydiene propyl dialkylammonium chloride and solvent are uniformly mixed up to the reducing thick oil viscosity
Agent.
4. application of the heavy crude thinner described in claims 1 or 2 in thickened oil recovery.
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| CN110317333B (en) * | 2018-03-29 | 2021-10-29 | 中国石油化工股份有限公司 | Humic acid modified viscosity reducer and preparation method thereof |
| CN109181670B (en) * | 2018-09-07 | 2020-06-09 | 中国科学院化学研究所 | Efficient thick oil viscosity reducer and preparation method thereof |
| CN110041904B (en) * | 2019-04-23 | 2021-08-31 | 中国海洋石油集团有限公司 | Humic acid and alkylamine compound type thick oil viscosity reducer and preparation method and application thereof |
| CN110713824B (en) * | 2019-09-24 | 2021-09-07 | 大港油田集团有限责任公司 | Anti-adsorption composite oil displacement system and preparation method thereof |
| CN111453791B (en) * | 2020-04-30 | 2022-06-03 | 大庆华营化工有限公司 | Water purification viscosity reducer and preparation method thereof |
| CN115353620B (en) * | 2022-08-29 | 2023-10-31 | 中海石油(中国)有限公司 | Polyphenol nanoparticle and preparation method and application thereof |
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| CN101768462A (en) * | 2008-12-31 | 2010-07-07 | 中国石油化工股份有限公司 | Emulsifying and viscosity-decreasing method of thick oil |
| WO2011021125A1 (en) * | 2009-08-20 | 2011-02-24 | Schlumberger Canada Limited | Methods for increasing the recovery rate of a hydrocarbon from an underground reservoir |
| CN103045224A (en) * | 2013-01-08 | 2013-04-17 | 陕西科技大学 | Preparation method of viscous oil viscosity reducer containing quaternary ammonium salt structure |
| CN106753284A (en) * | 2017-01-05 | 2017-05-31 | 中国科学院化学研究所 | A kind of viscosity reducer for crude oil and preparation method thereof |
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