CN106543024B - A kind of bisacrylamide surfactant and its preparation method and application - Google Patents
A kind of bisacrylamide surfactant and its preparation method and application Download PDFInfo
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- CN106543024B CN106543024B CN201610548889.6A CN201610548889A CN106543024B CN 106543024 B CN106543024 B CN 106543024B CN 201610548889 A CN201610548889 A CN 201610548889A CN 106543024 B CN106543024 B CN 106543024B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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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
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
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- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/30—Viscoelastic surfactants [VES]
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Abstract
The invention discloses a kind of bisacrylamide surfactant, belong to surfactant field, it is the compound with structure shown in Formulas I：Wherein R represents C8~C20Alkyl.Present invention also offers the preparation method of the bisacrylamide surfactant, with long-chain bromoalkane, dimethylamine and N, N ' methylene-bisacrylamide for raw material, is prepared through quaterisation and halogen substitution reaction.The raw material that this method is related to is easy to get, and cost is low, and synthetic method is simple, and synthesis condition is gentle, and the yield and purity of products therefrom are higher.The bisacrylamide surfactant is applied to fracturing fluid field, the prepared viscoelastic surfactant fracturing fluid that obtains has excellent heat-resisting property and stability.
Description
Technical field
The present invention relates to a kind of Gemini surface active agent and preparation method thereof.More particularly it relates to a kind of sun from
Sub- bisacrylamide surfactant and its preparation method and application.
Background technology
Aqueous fracturing fluid is broadly divided into：Natural plants fracturing fluid, cellulose fracturing fluid and synthetic polymer hydrofracturing fluid.
Above-mentioned several fracturing fluid systems, at home and abroad each oil field is widely used, and obtains good effect of increasing production.But use
The defects of common be present in these fracturing fluid systems, be exactly after fracturing liquid rubber-breaking residue will remain in crack, remain in crack
Polymer will the serious permeability for reducing proppant pack, so as to injure payzone, cause fracturing effect to be deteriorated.
The novel water-based fracturing fluid for a kind of non-polymer that late 1990s develop successfully solves these and asked
Topic.Due to being wherein free of polymer, adsorbance of the residue with proppant filling tape in fracture faces is significantly reduced, is formed high
The crack of flow conductivity.It is only 30%~45% that field experiment, which shows that the row of returning of guar gum fracturing fluid leads, and such non-polymer pressure
Proppant stages permeability retention rate that liquid takes sand filling is split typically more than 90%, and will not leave behind filter cake.Therefore, to stratum
Pollution level is smaller, the seepage flow situation of proppant packed layer and Reservoir Fracture is improved, so as to add Oil ＆ Gas Productivity.It is this
New Fracturing Fluid is non-polymer system, is also clean fracturing fluid or non-injury fracturing fluid, viscoelastic surfactant fracturing fluid.
In surfactant, Gemini surface active agent is by coupling base by two hydrophilic radicals and two hydrophobic groupings
A kind of new surfactant that group's connection forms.Compared with traditional surfactant, Gemini surface active agent can be more
The surface tension of water is effectively reduced, there is lower critical micelle concentration, higher absorption property and peculiar aggregation row
For, thus Gemini surface active agent, especially cation Gemini surfactant the fields such as tertiary oil recovery, sterilization, printing and dyeing by
To the extensive concern of people.
But existing cation Gemini surfactant preparation technology is complicated, especially prepare containing amide groups, ester group,
The Gemini surface active agent of the linkers such as ether, it usually needs use more than 100 DEG C of high temperature and the step of complexity, and make
Standby raw material is difficult to obtain so for preparing costly.Therefore need a kind of synthesis material badly to be easy to get, synthetic method is simple, synthesizes bar
Part is gentle, at a lower temperature cation Gemini surfactant made from can.
The content of the invention
It is an object of the invention to overcome the technique in the presence of existing cation Gemini surfactant technology of preparing to answer
It is miscellaneous, synthesis condition is harsh, the unobtainable above-mentioned deficiency of raw material, there is provided a kind of bisacrylamide surfactant.
It is a further object of the present invention to provide a kind of preparation method of above-mentioned surfactant.
It is a further object of the present invention to provide purposes of the above-mentioned surfactant in terms of fracturing fluid is prepared.
In order to realize foregoing invention purpose, the invention provides following technical scheme：
A kind of bisacrylamide surfactant, it is the compound with structure shown in Formulas I：
Wherein R represents C8~C20Alkyl.
Above-mentioned C8~C20Alkyl refer to the alkyl of the straight or branched with 8~20 carbon atoms, it is preferable that R is represented
The alkyl of 10~20 carbon atoms, it is further preferred that R represents the alkyl of 12~18 carbon atoms, it is highly preferred that R represents 12
The alkyl of~18 carbon atoms, most preferably, R represent the straight chained alkyl of 12~18 carbon atoms.
The preparation method of the bisacrylamide surfactant of the present invention, comprises the following steps：
S1, first long-chain bromoalkane and N, N '-methylene bisacrylamide acyl dimethylamine are mixed, add solvent, carry out quaternary ammonium salt
Change reaction, obtain mixed liquor；
S2, the mixed liquor freezing and crystallizing obtained into the bisacrylamide surfactant.
Further, above-mentioned long-chain bromoalkane is with R1The compound of-Br structures, wherein R1Represent C8~C20Alkyl.
Further, above-mentioned long-chain bromoalkane and above-mentioned N, the mol ratio of N '-methylene bisacrylamide acyl dimethylamine is 1.5: 1
~4: 1.Preferably, above-mentioned long-chain bromoalkane and above-mentioned N, the mol ratio of N '-methylene bisacrylamide acyl dimethylamine is 2: 1~3: 1.
Further, above-mentioned solvent is the one or more in ethanol, acetone and isopropanol.
Further, the reaction temperature of above-mentioned quaternization reaction is 10~90 DEG C, and the reaction time is 8~24 hours.It is excellent
Selection of land, the reaction temperature of above-mentioned quaternization reaction is 20~80 DEG C, and the reaction time is 10~18 hours.
Further, above-mentioned steps S1 also includes preparing the N, the step of N '-methylene bisacrylamide acyl dimethylamine, wherein
N, N '-methylene bisacrylamide acyl dimethylamine are the compound with structure shown in Formula II：
Above-mentioned N, N '-methylene bisacrylamide acyl dimethylamine can be prepared by following method：
A, N, N '-methylene-bisacrylamide are mixed with dimethylamine, adds polar solvent, react 8 at 10~80 DEG C
~24 hours, obtain reaction solution, the mol ratio of above-mentioned N, N '-methylene-bisacrylamide and dimethylamine is 1: 1.5~1: 4；
B, reaction solution is evaporated, dried, obtain the N, N '-methylene bisacrylamide acyl dimethylamine.
Preferably, the mol ratio of above-mentioned N, N '-methylene-bisacrylamide and dimethylamine is 1: 2~1: 4.Preferably, on
Step a is stated to react under conditions of 20~60 DEG C.Preferably, step a reaction time is 10~18 hours.Above-mentioned polar solvent
For water, alcohol, ketone etc., preferably water.
In the preparation method of above-mentioned N, N '-methylene bisacrylamide acyl dimethylamine, the evaporation of the step b, drying steps can
To complete in two steps；It can also be completed with a step, such as the reaction solution is evaporated under low pressure using rotary evaporator, be dry
It is dry, obtain N, N '-methylene bisacrylamide acyl dimethylamine.Preferably, reaction solution is evaporated under low pressure using rotary evaporator, done
It is dry, obtain N, N '-methylene bisacrylamide acyl dimethylamine.
The present invention bisacrylamide surfactant fracturing fluid application, by above-mentioned bisacrylamide surfactant
Fracturing fluid is mixed and made into counter ion salt, the mol ratio of wherein bisacrylamide surfactant and counter ion salt is 1: 2~3:
1, bisacrylamide surfactant accounts for the 1~5% of fracturing fluid gross mass.
Further, counter ion salt described in above-mentioned fracturing fluid refers to that negatively charged ion can be ionized out in aqueous
Material, such as salt, such as at least one of sodium salt, sylvite, ammonium salt, calcium salt；It is preferred that the counter ion salt is sodium salt and/or potassium
Salt；More preferably described counter ion salt is the one or more in sodium salicylate, sodium benzoate, sodium chloride and potassium chloride.It is preferred that institute
The mol ratio for stating bisacrylamide surfactant and the counter ion salt is 1: 2~3: 1.
Compared with prior art, beneficial effects of the present invention：
The present invention with long-chain bromoalkane, dimethylamine and N, N '-methylene-bisacrylamide for raw material, through addition reaction and season
Amine saltization reaction prepares a kind of cationic gemini quaternary surfactant, and the raw material that this method is related to is easy to get, and cost is low, synthesis
Method is simple, and synthesis condition is gentle, and the yield and purity of products therefrom are higher.The bisacrylamide surfactant is applied to
Fracturing fluid field, the prepared viscoelastic surfactant fracturing fluid that obtains have excellent heat-resisting property and stability.
Embodiment
With reference to test example and embodiment, the present invention is described in further detail.But this should not be understood
Following embodiment is only limitted to for the scope of the above-mentioned theme of the present invention, it is all that this is belonged to based on the technology that present invention is realized
The scope of invention.
Embodiment 1
By N, N '-methylene-bisacrylamide and dimethylamine in molar ratio 1: 2 ratio be dissolved in water, and reacted at 20 DEG C
18 hours, obtain reaction solution.Reaction solution is evaporated under low pressure using rotary evaporator, dried, obtains N, N '-di-2-ethylhexylphosphine oxide third
Alkene acyl dimethylamine.
By the N of preparation, N '-methylene bisacrylamide acyl dimethylamine and 1- bromos n-tetradecane in molar ratio 1: 2 ratio it is molten
In acetone, and reacted 18 hours at 40 DEG C, obtain mixed liquor.Mixed liquor freezing and crystallizing is obtained into bisacrylamide surface-active
Agent 1II.
The bisacrylamide surfactant 1II is the compound with structure shown in formula 1A,
3wt% surfactant 1II is mixed with 2wt% sodium salicylate and is dissolved in water, obtains Viscoelastic surfactant
Agent clean fracturing fluid, its temperature resistance reach 90 DEG C.The method of testing of the heat-resisting property is documented in standard " SYT 5107-2005 water
In base fracturing fluid property evaluation method ".
Embodiment 2
By N, N '-methylene-bisacrylamide and dimethylamine in molar ratio 1: 3 ratio be dissolved in water, and reacted at 40 DEG C
12 hours, obtain reaction solution.Reaction solution is evaporated under low pressure using rotary evaporator, dried, obtains N, N '-di-2-ethylhexylphosphine oxide third
Alkene acyl dimethylamine.
By the N of preparation, N '-methylene bisacrylamide acyl dimethylamine and 1- bromos hexadecane in molar ratio 1: 3 ratio it is molten
In acetone, and reacted 12 hours at 60 DEG C, obtain mixed liquor.Mixed liquor freezing and crystallizing is obtained into bisacrylamide surface-active
Agent 2II.
The surfactant 2II is the compound with structure shown in formula 2A,
3wt% surfactant 2II is mixed with 3wt% potassium chloride and is dissolved in water, obtains viscoelastic surfactant
Clean fracturing fluid, temperature resistance reach 105 DEG C.The method of testing of the heat-resisting property is documented in standard " the water base pressures of SYT5107-2005
Split liquid method of evaluating performance " in.
Embodiment 3
By N, N '-methylene-bisacrylamide and dimethylamine in molar ratio 1: 4 ratio be dissolved in water, and reacted at 60 DEG C
8 hours, obtain reaction solution.Reaction solution is evaporated under low pressure using rotary evaporator, dried, obtains white solid N, N '-Asia
The double acryloyl dimethylamine of methyl.
By the N of preparation, N '-methylene bisacrylamide acyl dimethylamine and 1- bromos n-octadecane in molar ratio 1: 4 ratio it is molten
In acetone, and reacted 8 hours at 80 DEG C, obtain mixed liquor, mixed liquor freezing and crystallizing is obtained into surfactant 3II.
The surfactant 3II is the compound with structure shown in formula 3A,
3wt% surfactant 3II and 3wt% sodium benzoate are dissolved in water, it is clear to obtain viscoelastic surfactant
Clean fracturing fluid, temperature resistance reach 120 DEG C.The method of testing of the heat-resisting property is documented in standard " SYT5107-2005 water-based fracturings
In liquid method of evaluating performance ".
Although being described in detail with reference to embodiment to the present invention, those skilled in the art are come
Say, it is obvious that it, which is made various changes and modifications, on the premise of without departing from the scope.Implementation described herein
What mode was merely exemplary, it is not limiting as the present invention.Many of the invention disclosed herein changes and modifications
It is possible, and fall into the scope of the present invention.Therefore, protection domain is not limited by description set out above, and it is only
Limited by appended claim, its scope includes all equivalents of claim theme.Each claim is incorporated to
Bright book is as embodiments of the present invention.Thus, claim is further instruction book, and is that the present invention is preferable to carry out
The increase of mode.The disclosure of all patents referred to herein, patent application and publication is incorporated herein by reference, bag
Include in exemplary, program that they are provided or other detailed supplements.
Claims (9)
1. a kind of bisacrylamide surfactant, it is the compound with structure shown in formula I：
（Ⅰ）
Wherein R represents C8~C20Alkyl.
2. bisacrylamide surfactant according to claim 1, it is characterised in that wherein R represents C10~C20 Hydrocarbon
Base.
3. prepare the method for the bisacrylamide surfactant described in claim 1, it is characterised in that comprise the following steps：
S1, first long-chain bromoalkane and N, N'- methylene bisacrylamide acyl dimethylamine are mixed, add solvent, it is anti-to carry out quaternization
Should, obtain mixed liquor；The long-chain bromoalkane is with R1The compound of-Br structures, wherein R1Represent C8~C20Alkyl；
S2, the mixed liquor freezing and crystallizing obtained into the bisacrylamide surfactant.
4. preparation method according to claim 3, it is characterised in that the step S1 also includes preparing the N, and N'- is sub-
The step of methyl pair acryloyl dimethylamine, it is 1 specially by mol ratio:1.5~1:4 N, N'- methylene-bisacrylamide and two
Methylamine mixes, and adds water, is reacted 8 ~ 24 hours at 10 ~ 80 DEG C and obtain reaction solution, then evaporated reaction solution, be dried to obtain institute
State N, N'- methylene bisacrylamide acyl dimethylamine.
5. preparation method according to claim 3, it is characterised in that the long-chain bromoalkane and the N, N'- methylene
The mol ratio of double acryloyl dimethylamine is 1.5:1~4:1.
6. preparation method according to claim 3, it is characterised in that the solvent is in ethanol, acetone and isopropanol
It is one or more of.
7. preparation method according to claim 3, it is characterised in that the reaction temperature of quaternization reaction for 10 ~
90 DEG C, the reaction time is 8 ~ 24 hours.
8. bisacrylamide surfactant as claimed in claim 1 is in the application of fracturing fluid, it is characterised in that will be described double
Acrylamide surfactant and counter ion salt are mixed and made into fracturing fluid, the bisacrylamide surfactant with it is described instead from
The mol ratio of alite is 1:2~3:1, the bisacrylamide surfactant accounts for the 1 ~ 5% of fracturing fluid gross mass.
9. bisacrylamide surfactant according to claim 8 is in the application of fracturing fluid, it is characterised in that described anti-
Ion salt is sodium salt, sylvite or its any combination.
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| CN107987213B (en) * | 2017-12-28 | 2020-07-21 | 深圳市华星光电技术有限公司 | Polarizing film material and preparation method thereof, polarizing film and preparation method thereof |
| CN112521306A (en) * | 2019-09-18 | 2021-03-19 | 天津大学 | Zwitterionic monomer containing bisamide structure and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE936395C (en) * | 1952-02-17 | 1955-12-15 | Henkel & Cie Gmbh | Process for the preparation of bisquaterner ammonium compounds |
| CN101899293A (en) * | 2010-08-02 | 2010-12-01 | 天津科技大学 | Twin cationic surface active agent and viscoelastic fracturing fluid containing same |
| CN103289669A (en) * | 2013-05-28 | 2013-09-11 | 四川安东油气工程技术服务有限公司 | Surfactant for fracturing fluid and preparation method and fracturing fluid thereof |
-
2016
- 2016-07-13 CN CN201610548889.6A patent/CN106543024B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE936395C (en) * | 1952-02-17 | 1955-12-15 | Henkel & Cie Gmbh | Process for the preparation of bisquaterner ammonium compounds |
| CN101899293A (en) * | 2010-08-02 | 2010-12-01 | 天津科技大学 | Twin cationic surface active agent and viscoelastic fracturing fluid containing same |
| CN103289669A (en) * | 2013-05-28 | 2013-09-11 | 四川安东油气工程技术服务有限公司 | Surfactant for fracturing fluid and preparation method and fracturing fluid thereof |
Non-Patent Citations (2)
| Title |
|---|
| Effect of amide bonds on the self-assembly of gemini surfactants;Jiaul Hoque et al.;《Phys.Chem.Chem.Phys.》;20141231;11279-11288 * |
| Selective and broad spectrum amphiphilic small molecules to combat bacterial resistance and eradicate biofilms;Jiaul Hoque et al.;《Chem.Commun.》;20151231;13670-13673 * |
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