CN106543024A - 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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- CN106543024A CN106543024A CN201610548889.6A CN201610548889A CN106543024A CN 106543024 A CN106543024 A CN 106543024A CN 201610548889 A CN201610548889 A CN 201610548889A CN 106543024 A CN106543024 A CN 106543024A
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- bisacrylamide
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- fracturing fluid
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- 0 C*(C)(*)*[Mn][N+](C)[O-] Chemical compound C*(C)(*)*[Mn][N+](C)[O-] 0.000 description 1
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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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- C—CHEMISTRY; METALLURGY
- 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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- C—CHEMISTRY; METALLURGY
- 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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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/30—Viscoelastic surfactants [VES]
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of bisacrylamide surfactant, belongs to surfactant field, which 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, Jing quaterisations and halogen substiuted reaction are prepared.The raw material that the method is related to is easy to get, low cost, and synthetic method is simple, and synthesis condition is gentle, and the yield and purity of products therefrom is higher.The bisacrylamide surfactant is applied to into 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
There is common defect in these fracturing fluid systems, be exactly after fracturing liquid rubber-breaking residue will remain in crack, remain in crack
Polymer by the serious permeability for reducing proppant pack, so as to injure payzone, cause fracturing effect to be deteriorated.
The novel water-based fracturing fluid of the class non-polymer that late 1990s develop successfully solves these and asks
Topic.Due to wherein not containing polymer, adsorbance of the residue with proppant filling tape in fracture faces is significantly reduced, form high
The crack of flow conductivity.It is only 30%～45% that field experimentation shows that the row of returning of guar gum fracturing fluid leads, and such non-polymer pressure
Split liquid and the proppant stages permeability retention rate of sand filling is taken typically more than 90%, and will not leave behind filter cake.Therefore, to stratum
Pollution level is less, improves the seepage flow situation of proppant packed layer and Reservoir Fracture, so as to increased 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 groups and two hydrophobic group
Roll into a ball the new surfactant of a class of connection.Compared with traditional surfactant, Gemini surface active agent can be more
The surface tension of water is effectively reduced, with lower critical micelle concentration, higher absorption property and peculiar aggregation row
For, therefore Gemini surface active agent, especially cation Gemini surfactant received in fields such as tertiary oil recovery, sterilization, printing and dyeing
To the extensive concern of people.
But existing cation Gemini surfactant complicated process of preparation, 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 that preparation cost is expensive.Therefore need a kind of synthesis material badly to be easy to get, synthetic method is simple, synthesize bar
Part is gentle, at a lower temperature just can be with obtained cation Gemini surfactant.
The content of the invention
It is an object of the invention to the technique in the presence of overcoming existing cation Gemini surfactant technology of preparing is multiple
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 technical scheme below：
A kind of bisacrylamide surfactant, which 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 represents 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 by long-chain bromoalkane and N, N '-methylene bisacrylamide acyl dimethylamine mixing, add solvent, carry out quaternary ammonium salt
Change reaction, obtain mixed liquor；
S2, the mixed liquor freezing and crystallizing is obtained into the bisacrylamide surfactant.
Further, above-mentioned long-chain bromoalkane is with R1The compound of-Br structures, wherein R1Represent C8～C20Alkyl.
Further, the mol ratio of above-mentioned long-chain bromoalkane and above-mentioned N, N '-methylene bisacrylamide acyl dimethylamine is 1.5: 1
～4: 1.Preferably, the mol ratio of above-mentioned long-chain bromoalkane and above-mentioned N, N '-methylene bisacrylamide acyl dimethylamine is 2: 1～3: 1.
Further, above-mentioned solvent is one or more in ethanol, acetone and isopropanol.
Further, the reaction temperature of above-mentioned quaternization reaction is 10～90 DEG C, and the response 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 response time is 10～18 hours.
Further, above-mentioned steps S1 also include the step of preparing the N, N '-methylene bisacrylamide acyl dimethylamine, wherein
N, N '-methylene bisacrylamide acyl dimethylamine is the compound with structure shown in Formula II：
Above-mentioned N, N '-methylene bisacrylamide acyl dimethylamine can be prepared by following method：
A, by N, N '-methylene-bisacrylamide is mixed with dimethylamine, add polar solvent, react 8 at 10～80 DEG C
～24 hours, reactant liquor is obtained, above-mentioned N, N '-methylene-bisacrylamide are 1: 1.5～1: 4 with the mol ratio of dimethylamine；
B, by reactant liquor evaporation, be dried, obtain the N, N '-methylene bisacrylamide acyl dimethylamine.
Preferably, above-mentioned N, N '-methylene-bisacrylamide are 1: 2～1: 4 with the mol ratio of dimethylamine.Preferably, on
State step a to react under conditions of 20～60 DEG C.Preferably, the response time of step a 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 step b, drying steps can
To complete in two steps；Can also be completed with a step, for example, under low pressure the reactant liquor be evaporated, is done using rotary evaporator
It is dry, obtain N, N '-methylene bisacrylamide acyl dimethylamine.Preferably, under low pressure reactant liquor is evaporated, is done using rotary evaporator
It is dry, obtain N, N '-methylene bisacrylamide acyl dimethylamine.
Application of the bisacrylamide surfactant of the present invention in fracturing fluid, by above-mentioned bisacrylamide surfactant
Fracturing fluid is mixed and made into counter ion salt, wherein bisacrylamide surfactant and the mol ratio of counter ion salt are 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 is referred to and can ionize out negatively charged ion in aqueous
Material, such as salt, such as sodium salt, potassium salt, ammonium salt, at least one of calcium salt；It is preferred that the counter ion salt is sodium salt and/or potassium
Salt；More preferably described counter ion salt is one or more in sodium salicylate, sodium benzoate, Sodium Chloride and potassium chloride.It is preferred that institute
The mol ratio that bisacrylamide surfactant is stated with the counter ion salt is 1: 2～3: 1.
Compared with prior art, beneficial effects of the present invention：
The present invention is with long-chain bromoalkane, dimethylamine and N, N '-methylene-bisacrylamide for raw material, Jing additive reaction and season
Amine saltization reaction prepares a cationoid gemini surfactant, and the raw material that the method is related to is easy to get, low cost, synthesis
Method is simple, and synthesis condition is gentle, and the yield and purity of products therefrom is 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.
Specific embodiment
With reference to test example and specific embodiment, the present invention is described in further detail.But this should not be understood
Scope for above-mentioned theme of the invention is only limitted to below example, and all technologies realized based on present invention belong to this
The scope of invention.
Embodiment 1
By N, N '-methylene-bisacrylamide and dimethylamine in molar ratio 1: 2 ratio be dissolved in water, and react at 20 DEG C
18 hours, obtain reactant liquor.Under low pressure reactant liquor is evaporated, is dried using rotary evaporator, obtain N, N '-di-2-ethylhexylphosphine oxide third
Alkene acyl dimethylamine.
The N that will be prepared, N '-methylene bisacrylamide acyl dimethylamine and 1- bromos n-tetradecane in molar ratio 1: 2 ratio it is molten
In acetone, and react 18 hours at 40 DEG C, obtain mixed liquor.Mixed liquor freezing and crystallizing is obtained into bisacrylamide surface activity
Agent 1II.
The bisacrylamide surfactant 1II is the compound with structure shown in formula 1A,
The surfactant 1II of 3wt% is mixed with the sodium salicylate of 2wt% and is dissolved in water, obtain 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 methodology ".
Embodiment 2
By N, N '-methylene-bisacrylamide and dimethylamine in molar ratio 1: 3 ratio be dissolved in water, and react at 40 DEG C
12 hours, obtain reactant liquor.Under low pressure reactant liquor is evaporated, is dried using rotary evaporator, obtain N, N '-di-2-ethylhexylphosphine oxide third
Alkene acyl dimethylamine.
The N that will be prepared, N '-methylene bisacrylamide acyl dimethylamine and 1- bromos hexadecane in molar ratio 1: 3 ratio it is molten
In acetone, and react 12 hours at 60 DEG C, obtain mixed liquor.Mixed liquor freezing and crystallizing is obtained into bisacrylamide surface activity
Agent 2II.
The surfactant 2II is the compound with structure shown in formula 2A,
The surfactant 2II of 3wt% is mixed with the potassium chloride of 3wt% and is dissolved in water, obtain 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 react at 60 DEG C
8 hours, obtain reactant liquor.Under low pressure reactant liquor is evaporated, is dried using rotary evaporator, obtain white solid N, N '-Asia
The double acryloyl dimethylamine of methyl.
The N that will be prepared, N '-methylene bisacrylamide acyl dimethylamine and 1- bromos n-octadecane in molar ratio 1: 4 ratio it is molten
In acetone, and react 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,
The sodium benzoate of the surfactant 3II of 3wt% and 3wt% is dissolved in into water, viscoelastic surfactant is obtained clear
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 to the present invention with reference to specific embodiment, those skilled in the art are come
Say, it is obvious which to be made various changes and modifications on the premise of without departing from the scope.Enforcement described herein
What mode was merely exemplary, which is not limiting as the present invention.The many of the present invention disclosed herein changes and modifications and is
It is possible, and fall into the scope of the present invention.Therefore, protection domain is not limited by description set out above, and which is only
Limited by appended claim, its scope includes all equivalents of claim theme.Each claim is incorporated to
Bright book is used 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 their the exemplary of offer, program or other detailed supplements.
Claims (10)
1. a kind of bisacrylamide surfactant, which is the compound with structure shown in Formulas I：
Wherein R represents C8～C20Alkyl.
2. bisacrylamide surfactant according to claim 1, it is characterised in that wherein R represents C10～C20Hydrocarbon
Base.
3. the method for preparing the bisacrylamide surfactant described in claim 1, it is characterised in that comprise the following steps：
S1, first by long-chain bromoalkane and N, N '-methylene bisacrylamide acyl dimethylamine mixing, add solvent, carry out quaternization anti-
Should, obtain mixed liquor；
S2, the mixed liquor freezing and crystallizing is obtained into the bisacrylamide surfactant.
4. preparation method according to claim 3, it is characterised in that step S1 also includes preparing the N, N '-Asia
The step of methyl double acryloyl dimethylamine, specially by mol ratio for 1: 1.5～1: 4 N, N '-methylene-bisacrylamide with
Dimethylamine mixes, and adds water, and the reaction at 10～80 DEG C obtains reactant liquor in 8～24 hours, subsequently by reactant liquor evaporation, dry
To the N, N '-methylene bisacrylamide acyl dimethylamine.
5. preparation method according to claim 3, it is characterised in that the long-chain bromoalkane is with R1The change of-Br structures
Compound, wherein R1Represent C8～C20Alkyl.
6. 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.
7. preparation method according to claim 3, it is characterised in that during the solvent is ethanol, acetone and isopropanol
One or more.
8. preparation method according to claim 3, it is characterised in that the reaction temperature of the quaternization reaction is 10～
90 DEG C, the response time is 8～24 hours.
9. application of the bisacrylamide surfactant as claimed in claim 1 in 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 it is anti-from
The mol ratio of alite is 1: 2～3: 1, and the bisacrylamide surfactant accounts for the 1～5% of fracturing fluid gross mass.
10. application of the bisacrylamide surfactant in fracturing fluid according to claim 9, it is characterised in that described anti-
Ion salt is sodium salt, potassium salt or its combination in any.
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| CN201610548889.6A CN106543024B (en) | 2016-07-13 | 2016-07-13 | A kind of bisacrylamide surfactant and its preparation method and application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107987213A (en) * | 2017-12-28 | 2018-05-04 | 深圳市华星光电技术有限公司 | Polarisation membrane material and preparation method thereof, light 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 |
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| 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 |
|---|
| JIAUL HOQUE ET AL.: "Effect of amide bonds on the self-assembly of gemini surfactants", 《PHYS.CHEM.CHEM.PHYS.》 * |
| JIAUL HOQUE ET AL.: "Selective and broad spectrum amphiphilic small molecules to combat bacterial resistance and eradicate biofilms", 《CHEM.COMMUN.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107987213A (en) * | 2017-12-28 | 2018-05-04 | 深圳市华星光电技术有限公司 | Polarisation membrane material and preparation method thereof, light 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 |
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| CN106543024B (en) | 2018-03-30 |
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