CN109731526A - A kind of fluorine-containing surfactant compound and preparation method and application - Google Patents
A kind of fluorine-containing surfactant compound and preparation method and application Download PDFInfo
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Abstract
The present invention relates to a kind of fluorine-containing surfactant compound and preparation method and applications.Fluorine-containing surfactant has structure shown in Formulas I.Preparation method includes: that (1) perfluoro-octanoyl chlorine compound reacts to obtain Formula II compound with positive heptyl amice, (2) Formula II compound reacts to obtain III compound of formula with chlorine enanthic acid compound, (3) III compound of formula is reacted with alkali, and compound of formula I fluorine-containing surfactant is made.Fluorine-containing surfactant of the invention has good hydrophobic oleophobic characteristic, reservoir significantly can be reversed to air humidity by liquid is moist, to keep fracture faces to clean, pit shaft working solution is reduced in the absorption of surface of stratum, especially in the small gaps of low permeability reservoir and hole are shouted, the mobility of fluid can be significantly improved, to achieve the purpose that volume increase.
Description
Technical field
The present invention relates to a kind of fluorine-containing surfactant for changing shale reservoir surface wettability and preparation method and application,
Belong to the technical field of petrochemical industry for improving shale gas recovery ratio.
Technical background
Surfactant refers to the substance that can reduce solvent surface tension significantly with extremely low concentration.Its molecule
Structure has the characteristics that common, i.e., its molecule is made of nonpolar hydrophobic group and polar hydrophilic group two parts.Two
The molecular fragment or group that partial structure and performance is completely contradicted are in the both ends of same molecule, and are connected with chemical bond,
Form a kind of asymmetric, polar structure.Thus the substance is not only hydrophilic, but also oleophylic, but is not whole hydrophilic or close
The characteristic of oil.It is a series of that emulsification, dispersion, solubilising, washing etc. can be played.
Fluorocarbon surfactant is as most important special surfactant, due to introducing fluorine (F) element in its molecule,
So that it has more unique, superior performances than conventional surfactants, surfactant is substantially increased
Use value, and then paid much attention to and be widely applied in all trades and professions.It is conventional carbon hydrogen meter face from structure
Hydrogen moiety in activating agent or all replaced fluorine atom, and fluorine electronegativity in all elements is maximum, Van der Waals is former
Sub- radius is that minimum, atomic polarizability are minimum in addition to hydrogen again.Therefore, the singly-bound that fluorine atom is formed is than carbon atom and other atoms
The singly-bound bond energy of formation is all big, and bond distance is shorter, and this structure also makes fluorocarbon chain hydrophobic effect not only than hydrocarbon stable structure
It is strong more than hydrocarbon chain, and interaction force is weak between fluorocarbon chain.It is living that its high surface is imparted just because of this special structure
Property, high heat resistance stability, high chemical stability and both hydrophobic and oleophobic good characteristic, there are other surfactants can not compare
Quasi- effect can be applied to some incompetent special application fields of other surfactants, wide market.But
Most of the fluorocarbon surfactant that can be applied in oilfield exploitation procedure change reservoir wettability currently on the market is high poly-
The fluorocarbon surfactant relative molecular mass of species type (such as CN101449026), the type is big, easily blocks porous Jie of reservoir
Matter reduces reservoir permeability, even more serious particularly with low permeability reservoir, and high polymer is difficult biodegrade, causes to stratum
Environmental pollution
Summary of the invention
In view of the deficiencies of the prior art, of the invention provide a kind of can be applied to change the new of shale reservoir surface wettability
Type small molecule fluorine-containing surfactant, the surfactant also have other than the advantage with high polymer fluorocarbon surfactant
There is molecular weight small, is not easy to plug porous media, the advantages that biodegradability is strong.
The present invention also provides the preparation method of the fluorine-containing surfactant and applications.
Technical scheme is as follows:
A kind of fluorine-containing surfactant has structure shown in Formulas I:
Wherein, M K, Na or Li.
Above-mentioned fluorine-containing surfactant has three chains hydrophobic or oleophobic structure.With good hydrophobic oleophobic characteristic.
According to the present invention, a kind of preparation method of fluorine-containing surfactant compound, comprising steps of
(1) in the presence of a catalyst, in anhydrous ethanol solvent, react perfluoro-octanoyl chlorine compound with positive heptyl amice, make
II compound of formula is obtained,
(2) in the presence of a catalyst, in acetone solvent, react Formula II compound with chlorine enanthic acid compound, be made formula
III compound,
(3) in acetone solvent, in the presence of alkali, III compound of formula is reacted with alkali, and it is living that fluorochemical surface shown in Formulas I is made
Property immunomodulator compounds:
Wherein, M K, Na or Li.
, according to the invention it is preferred to, reaction raw materials and reagent used are that analysis is pure or more in above step (1)-(4)
Purity.It reacts described in step (1)-(4) and is carried out in glass reaction kettle respectively.
, according to the invention it is preferred to, step (1) catalyst is selected from pyridine or dimethylformamide；
, according to the invention it is preferred to, step (2) catalyst is selected from pyridine or dimethylformamide.
, according to the invention it is preferred to, the reaction of step (1) includes the one or more of the following conditions:
A1: the amount of perfluoro caprylic acid and catalyst material ratio is 9-15:1, further preferred 10-12:1；
A2: the mass ratio of the material of perfluoro caprylic acid and positive heptyl amice is 1:2；
A3: reaction carries out under agitation, and 65-75 DEG C of reaction temperature；Preferably, the reaction time is 2-3 hours；
A4: being filtered after reaction, then rotates removing solvent, and drying obtains II compound products of formula.
, according to the invention it is preferred to, the reaction of step (2) includes the one or more of the following conditions:
B1: Formula II and the amount of catalyst material ratio are 9-15:1, further preferred 10-12:1；
B2: the mass ratio of the material of Formula II compound and chlorine enanthic acid compound is 1:1~2；Further preferably, Formula II compound
With chlorine enanthic acid 1:1.2~1.6.
B3: reaction carries out under agitation, and 50-55 DEG C of reaction temperature, pH value of reaction system 8；Preferably, when reaction
Between 8-10 hours；
B4: being filtered after reaction, then rotates removing solvent, and drying obtains III compound products of formula；
, according to the invention it is preferred to, the reaction of step (3) includes the one or more of the following conditions:
C1: the mass ratio of the material of formula III compound and alkali is 1:2~1.6；
C2: the alkali is added in the form of the aqueous solution of mass fraction 30-60%；
C3: the alkali is sodium hydroxide, potassium hydroxide or lithium hydroxide；
C4: reaction carries out under agitation, and 25-30 DEG C of reaction temperature；Preferably, reaction time 3-4 hours；
C5: revolving removes solvent after reaction, adds alcohol and is filtered to remove chloride, obtains compound of formula I finished product.
In the preparation method of present invention described above compound of formula I, the dosage of all solvents is meltage, is particularly limited to
Except.
Reaction route of the invention is as follows:
The application of fluorine-containing surfactant compound of the invention, for changing shale reservoir surface wettability, to improve
Shale gas recovery ratio.
The application of fluorine-containing surfactant compound of the invention, the method is as follows:
Fluorine-containing surfactant compound shown in Formulas I of the invention and deionized water are configured to solution, worked with pit shaft
Liquid is pressed into well together, and reservoir is reversed to air humidity by liquid is moist, reduces pit shaft working solution in the absorption of surface of stratum.It is fluorine-containing
If surfactant compounds and deionized water are configured to solution such as not use immediately, need to be sealed.Further preferably
, the solution that fluorine-containing surfactant compound of the invention adds deionized water to be configured to mass fraction 0.07-1.2% is made
With.
Excellent results of the invention:
1, the fluorine-containing surfactant compound provided by the invention has three chains hydrophobic or oleophobic structure, has good
Hydrophobic oleophobic characteristic, reservoir is reversed to air humidity (- Figure 14 referring to fig. 2) by liquid is moist with can dramatically, to keep crack table
Face cleaning reduces pit shaft working solution in the absorption of surface of stratum, especially in the small gaps of low permeability reservoir and hole are shouted, Ke Yiming
The aobvious mobility for improving fluid, to achieve the purpose that volume increase.And conventional fluorocarbon surfactant only has hydrophobic or oleophobic list
Chain structure cannot achieve the purpose of the present invention.
2, fluorine-containing surfactant compound provided by the invention is easily prepared, 86% or more yield, and highest is close to
90%, it can be configured to aqueous solution with water arbitrary proportion, reservoir surface can be changed into air humidity by liquid is moist, application effect is good
It is good, it is conducive to scene and promotes.
3, fluorine-containing surfactant preparation method of the invention is easy to operate, and reaction condition is mild, and by-product is few, is easy to control
System, key point are the presence that first step reaction cannot have water.
Detailed description of the invention
Fig. 1 water phase the core surface handled without fluorine-containing surfactant sprawl state and contact angle size θ, θ=
35°；
Fig. 2 water phase is in sprawling through treated the core surface of fluorine-containing surfactant solution described in the present embodiment 1
State and contact angle size θ, θ=101 °；
Fig. 3 water phase is in sprawling through treated the core surface of fluorine-containing surfactant solution described in the present embodiment 2
State and contact angle size θ, θ=125；
Fig. 4 water phase is in sprawling through treated the core surface of fluorine-containing surfactant solution described in the present embodiment 3
State and contact angle size θ, θ=128 °；
Fig. 5 water phase is in sprawling through treated the core surface of fluorine-containing surfactant solution described in the present embodiment 4
State and contact angle size θ, θ=133 °；
Fig. 6 water phase is in sprawling through treated the core surface of fluorine-containing surfactant solution described in the present embodiment 5
State and contact angle size θ, θ=134 °；
Fig. 7 water phase is in sprawling through treated the core surface of fluorine-containing surfactant solution described in the present embodiment 6
State and contact angle size θ, θ=133 °；
Fig. 8 oil mutually sprawls state and contact angle size θ, θ=0 in the shale surface handled without air humidity reversal agents；
Treated the core surface of fluorine-containing surfactant solution described in Fig. 9 oil Xiang Jing the present embodiment 1 is sprawled
State and contact angle size θ, θ=73 °；
Treated the core surface of fluorine-containing surfactant solution described in Figure 10 oil Xiang Jing the present embodiment 2 is sprawled
State and contact angle size θ, θ=95 °；
Treated the core surface of fluorine-containing surfactant solution described in Figure 11 oil Xiang Jing the present embodiment 3 is sprawled
State and contact angle size θ, θ=108 °；
Treated the core surface of fluorine-containing surfactant solution described in Figure 12 oil Xiang Jing the present embodiment 4 is sprawled
State and contact angle size θ, θ=115 °；
Treated the core surface of fluorine-containing surfactant solution described in Figure 13 oil Xiang Jing the present embodiment 5 is sprawled
State and contact angle size θ, θ=121 °；
Treated the core surface of fluorine-containing surfactant solution described in Figure 14 oil Xiang Jing the present embodiment 6 is sprawled
State and contact angle size θ, θ=120 °；
Wherein, water phase used is deionized water, and oil is mutually hexadecane, and fluorine-containing surfactant solution is now to match.
The infrared spectrum of prepared fluorocarbon surfactant compound in Figure 15 embodiment 1；Abscissa is wavelength (nm), is indulged
Coordinate is transmitance %.
Specific embodiment
The present invention will be described specifically by embodiment below, it will help further understand the present invention, but and unlimited
Raw materials used in the present invention, embodiment is commercially available material." % " in embodiment is mass percent, and special instruction is removed
Outside.
Embodiment 1
A kind of preparation of fluorine-containing surfactant compound, steps are as follows:
(1) in the round-bottomed flask for taking positive heptyl amice 138g (1.2mol) and pyridine 4.8g (0.06mol) Yu Peiyou magneton, with nothing
Water-ethanol perfluorooctane chloride 259g (0.6mol) is slowly added dropwise with constant pressure funnel under ice bath, is added dropwise, instead as solvent
75 DEG C are warming up to after answering 2 hours, is reacted 8 hours under oil bath, is filtered, precipitation, drying obtains Formula II compound.
(2) in the round-bottomed flask of Formula II compound 153g (0.3mol) the Yu Peiyou magneton for taking step (1) to prepare, with appropriate
Acetone as solvent, be warming up to 55 DEG C, after to be dissolved, chlorine enanthic acid 49.2g (0.3mol) slowly instilled with constant pressure funnel,
It is added dropwise, the molten lower reaction of oil 8 hours stands, filters, be concentrated, crystallization, drying obtains formula III compound.
(3) take formula III compound made from 63.7g (0.1mol) step (2) in glass reaction kettle, using acetone as molten
Agent is slowly added to the sodium hydrate aqueous solution of 9g (0.12mol) 50%, reaction 2 using constant pressure funnel under agitation
After hour, revolving removes solvent and water, is concentrated, and crystallization, drying obtains compound of formula I (66.5g).Yield 86.2%.
Its structural characterization infrared spectrum is as shown in figure 15.
Performance measurement:
By this example prepare fluorine-containing surfactant add deionized water be made into 0.5% solution, by pretreated rock core
It is impregnated in the solution of above-mentioned 0.5% fluorine-containing surfactant aging 48 hours, 90 DEG C of drying and room temperature 8 hours make
With the water phase of JC2000D contact angle instrument measurement after processing with oil mutually in core surface contact angle, contact angle is
101 ° (as shown in Figure 2), oil connect feeler be 73 ° (as shown in Figure 9).Water phase used is deionized water, and oil is mutually hexadecane
(similarly hereinafter).
Embodiment 2
Preparing for fluorine-containing surfactant is as described in Example 1, except that: the fluorine-containing surfactant of preparation is added
Deionized water is made into 0.7% solution, is impregnated rock core 48 hours with it, room temperature 8 hours after drying, measures water after processing
In the contact angle of core surface, contact angle is 125 ° (as shown in Figure 3) for phase and oily phase, and oil connects feeler for 95 ° of (such as figures
Shown in 10).
Embodiment 3
Preparing for fluorine-containing surfactant is as described in Example 1, except that: the fluorine-containing surfactant of preparation is added
Deionized water is made into 1.0% solution, is impregnated rock core 48 hours with it, room temperature 8 hours after drying, measures water after processing
Mutually and oil mutually core surface contact angle, contact angle be 128 ° (as shown in Figure 4), oil connect feeler for 108 ° (such as
Shown in Figure 11).
Embodiment 4
Preparing for fluorine-containing surfactant is as described in Example 1, the difference is that in step (2), Formula II compound and chlorine heptan
The amount ratio of acid substance is 1:1.2.Final product fluorine-containing surfactant is made through step (3).Yield 86.8%.
Performance measurement:
By this example prepare fluorine-containing surfactant add deionized water be made into 0.7% solution, by pretreated rock core
It is impregnated in above-mentioned 0.7% fluorine-containing surfactant solution aging 48 hours, 90 DEG C of drying simultaneously room temperature 8 hours, measurement
Mutually in core surface contact angle, contact angle is 133 ° (as shown in Figure 5) for water phase after processing and oil, and oil connects feeler
It is 115 °, as shown in figure 12.
Embodiment 5
Preparing for fluorine-containing surfactant is as described in Example 1, the difference is that in step (2), Formula II compound and chlorine heptan
The amount ratio of acid substance is 1:1.4.Final product fluorine-containing surfactant is made through step (3).Yield 88.6%.
Performance measurement:
By this example prepare fluorine-containing surfactant add deionized water be made into 0.7% solution, by pretreated rock core
It is impregnated in above-mentioned 0.7% fluorine-containing surfactant solution aging 48 hours, 90 DEG C of drying simultaneously room temperature 8 hours, measurement
Mutually in core surface contact angle, contact angle is 134 ° (as shown in Figure 6) for water phase after processing and oil, and oil connects feeler
For 121 ° (as shown in figure 13).
Embodiment 6
Preparing for fluorine-containing surfactant is as described in Example 1, the difference is that in step (2), Formula II compound and chlorine heptan
The amount ratio of acid substance is 1:1.6.Final product fluorine-containing surfactant is made through step (3).Yield 89.2%.
Performance measurement:
By this example prepare fluorine-containing surfactant add deionized water be made into 0.7% solution, by pretreated rock core
It is impregnated in above-mentioned 0.7% fluorine-containing surfactant solution aging 48 hours, 90 DEG C of drying simultaneously room temperature 8 hours, measurement
Mutually in core surface contact angle, contact angle is 133 ° (as shown in Figure 7) for water phase after processing and oil, and oil connects feeler
For 120 ° (as shown in figure 14).
In above embodiments, 1 fluorine-containing surfactant solution concentration of embodiment is small, and hydrophobic oleophobic ability is limited, implements
Example 2-3 concentration is high, has all reached air humidity effect, with the increase of fluorine-containing surfactant solution concentration, wettability reversal
Can be stronger, when concentration is more than 0.7%, performance change is little, it is contemplated that cost problem, therefore concentration 0.7% is used when application
It is preferred；Formula II compound and chlorine enanthic acid the mass ratio of the material have been investigated in embodiment 4-6, as reactant chlorine enanthic acid is excessive more,
In-between product Formula II compound reaction is more abundant, and when its mass ratio of the material is more than 1:1.4, yield variation is little.
Claims (9)
1. a kind of fluorine-containing surfactant has structure shown in Formulas I:
Wherein, M K, Na or Li.
2. a kind of preparation method of fluorine-containing surfactant compound, comprising steps of
(1) in the presence of a catalyst, in anhydrous ethanol solvent, react perfluoro-octanoyl chlorine compound with positive heptyl amice, be made formula
II compound,
(2) in the presence of a catalyst, in acetone solvent, react Formula II compound with chlorine enanthic acid compound, be made formula III change
Object is closed,
(3) in acetone solvent, in the presence of alkali, III compound of formula is reacted with alkali, and compound of formula I fluorine-containing surfactants are made
Agent:
Wherein, M K, Na or Li.
3. the preparation method of fluorine-containing surfactant compound according to claim 2, which is characterized in that step (1) institute
It states catalyst and is selected from pyridine or dimethylformamide；Step (2) catalyst is selected from pyridine or dimethylformamide.
4. the preparation method of fluorine-containing surfactant compound according to claim 2, which is characterized in that step (1)
Reaction includes the one or more of the following conditions:
A1: the amount of perfluoro caprylic acid and catalyst material ratio is 9-15:1, further preferred 10-12:1；
A2: the mass ratio of the material of perfluoro caprylic acid and positive heptyl amice is 1:2；
A3: reaction carries out under agitation, and 65-75 DEG C of reaction temperature；Preferably, the reaction time is 2-3 hours；
A4: being filtered after reaction, then rotates removing solvent, and drying obtains II compound products of formula.
5. the preparation method of fluorine-containing surfactant compound according to claim 2, which is characterized in that step (2)
Reaction includes the one or more of the following conditions:
B1: Formula II and the amount of catalyst material ratio are 9-15:1, further preferred 10-12:1；
B2: the mass ratio of the material of Formula II compound and chlorine enanthic acid compound is 1:1~2；Preferably, Formula II compound and chlorine enanthic acid
1:1.2~1.6；
B3: reaction carries out under agitation, and 50-55 DEG C of reaction temperature, pH value of reaction system 8；Preferably, reaction time 8-
10 hours；
B4: being filtered after reaction, then rotates removing solvent, and drying obtains III compound products of formula.
6. the preparation method of fluorine-containing surfactant compound according to claim 2, which is characterized in that step (3)
Reaction includes the one or more of the following conditions:
C1: the mass ratio of the material of formula III compound and alkali is 1:2~1.6；
C2: the alkali is added in the form of the aqueous solution of mass fraction 30-60%；
C3: the alkali is sodium hydroxide, potassium hydroxide or lithium hydroxide；
C4: reaction carries out under agitation, and 25-30 DEG C of reaction temperature；Preferably, reaction time 3-4 hours；
C5: revolving removes solvent after reaction, adds alcohol and is filtered to remove chloride, obtains compound of formula I finished product.
7. the application of fluorine-containing surfactant compound described in claim 1, for changing shale reservoir surface wettability, with
Improve shale gas recovery ratio.
8. the application of fluorine-containing surfactant compound as claimed in claim 7, the method is as follows:
Fluorine-containing surfactant compound shown in Formulas I by claim 1 and deionized water are configured to solution, with pit shaft working solution
It is pressed into well together, reservoir is reversed to air humidity by liquid is moist, reduces pit shaft working solution in the absorption of surface of stratum.
9. the application of fluorine-containing surfactant compound as claimed in claim 7, wherein contain shown in the Formulas I by claim 1
The solution that fluorinated surfactant compound adds deionized water to be configured to mass fraction 0.07-1.2% uses.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110903820A (en) * | 2019-11-06 | 2020-03-24 | 中国石油集团渤海钻探工程有限公司 | Shuangshuang synergistic cleanup additive and preparation method thereof |
| CN111111550A (en) * | 2019-12-27 | 2020-05-08 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008255094A (en) * | 2007-03-10 | 2008-10-23 | Japan Science & Technology Agency | Method for containing optically active homoallyl hydrazinoesters |
| CN101343242A (en) * | 2008-09-08 | 2009-01-14 | 四川大学 | Acryloyl di-quaternary ammonium salt and preparation thereof |
| CN102140338A (en) * | 2011-01-04 | 2011-08-03 | 中国石油大学(华东) | Fluorocarbon surfactant binary composite foam flooding system |
| CN102775381A (en) * | 2011-05-13 | 2012-11-14 | 中国科学院上海药物研究所 | Substituted hydrazide compound, and its preparation method, medicinal compositions and application |
-
2018
- 2018-12-25 CN CN201811592717.4A patent/CN109731526B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008255094A (en) * | 2007-03-10 | 2008-10-23 | Japan Science & Technology Agency | Method for containing optically active homoallyl hydrazinoesters |
| CN101343242A (en) * | 2008-09-08 | 2009-01-14 | 四川大学 | Acryloyl di-quaternary ammonium salt and preparation thereof |
| CN102140338A (en) * | 2011-01-04 | 2011-08-03 | 中国石油大学(华东) | Fluorocarbon surfactant binary composite foam flooding system |
| CN102775381A (en) * | 2011-05-13 | 2012-11-14 | 中国科学院上海药物研究所 | Substituted hydrazide compound, and its preparation method, medicinal compositions and application |
Non-Patent Citations (1)
| Title |
|---|
| 李永飞等: "特种氟碳表面活性剂的研究及应用进展", 《化工进展》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110903820A (en) * | 2019-11-06 | 2020-03-24 | 中国石油集团渤海钻探工程有限公司 | Shuangshuang synergistic cleanup additive and preparation method thereof |
| CN111111550A (en) * | 2019-12-27 | 2020-05-08 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
| CN111111550B (en) * | 2019-12-27 | 2021-11-30 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
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