CN112250703A - Preparation method of borate crosslinking agent and product - Google Patents
Preparation method of borate crosslinking agent and product Download PDFInfo
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- CN112250703A CN112250703A CN202011109669.6A CN202011109669A CN112250703A CN 112250703 A CN112250703 A CN 112250703A CN 202011109669 A CN202011109669 A CN 202011109669A CN 112250703 A CN112250703 A CN 112250703A
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- Prior art keywords
- tetraethylenepentamine
- boric acid
- molar ratio
- borate
- borate ester
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- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 title claims abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- -1 borate ester Chemical class 0.000 claims abstract description 25
- 239000004327 boric acid Substances 0.000 claims abstract description 21
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000003756 stirring Methods 0.000 claims abstract description 16
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 3
- 239000004971 Cross linker Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012530 fluid Substances 0.000 abstract description 16
- 238000004132 cross linking Methods 0.000 abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 235000015110 jellies Nutrition 0.000 abstract description 3
- 239000008274 jelly Substances 0.000 abstract description 3
- 238000010008 shearing Methods 0.000 abstract description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920013818 hydroxypropyl guar gum Polymers 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- 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
- 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
- C09K8/685—Compositions based on water or polar solvents containing organic compounds containing cross-linking agents
-
- 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
- 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
- C09K8/84—Compositions based on water or polar solvents
- C09K8/86—Compositions based on water or polar solvents containing organic compounds
- C09K8/88—Compositions based on water or polar solvents containing organic compounds macromolecular compounds
- C09K8/887—Compositions based on water or polar solvents containing organic compounds macromolecular compounds containing cross-linking agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention relates to a preparation method of a borate ester cross-linking agent, which comprises the following steps of adding ethylene glycol into an ethanol solvent, uniformly stirring, slowly adding boric acid, wherein the molar ratio of the ethylene glycol to the boric acid is 1 (1.0-1.2), stirring and refluxing for 1-2h, and removing the ethanol solvent by a reduced pressure distillation method to obtain an intermediate; mixing the intermediate and tetraethylenepentamine together, wherein the molar ratio of the tetraethylenepentamine to the intermediate is 1 (5.0-5.5), heating to 120 ℃ at the speed of 2-5 ℃/min, continuing to react, and cooling to room temperature to obtain the product, namely the borate cross-linking agent. The borate ester crosslinking agent contains five borate ester groups, has the characteristics of controllable crosslinking time, small addition amount, good temperature resistance and shearing resistance of crosslinked jelly and the like, can be used for preparing fracturing fluid for crosslinking from produced water of an oil field, and effectively solves the two problems of environmental protection and water for fracturing.
Description
Technical Field
The invention belongs to the technical field of petroleum and natural gas exploitation, and particularly relates to a preparation method of a borate ester cross-linking agent and a product.
Background
The hydraulic fracturing transformation is an important yield increasing measure for effective development of oil and gas fields, and fracturing fluid is required to carry a propping agent into fractures in the fracturing process, so that the flow conductivity of a reservoir is improved, and the yield of an oil and gas well is improved. The guanidine gum fracturing fluid is a fracturing fluid system which is most widely applied in the fracturing operation of the oil-gas field at present, and the using amount of the guanidine gum fracturing fluid accounts for more than 80 percent of all the fracturing fluid systems. In the using process, a cross-linking agent is required to be added to form jelly, so that the sand carrying performance is improved. At present, the water for preparing the fracturing fluid is more and more tense, and the two problems of environmental protection and water for fracturing can be effectively relieved by directly preparing the fracturing fluid from the produced water of an oil field. Because the oil field produced water has complex components and high mineralization, the problems of unstable performance, poor temperature resistance and shear resistance after crosslinking and the like exist in the existing crosslinking agent for crosslinking, and therefore, the development of a novel crosslinking agent suitable for preparing the fracturing fluid from the oil field produced water is needed.
Aiming at the problems, the borate ester crosslinking agent and the preparation method thereof are provided for preparing the guanidine gum fracturing fluid system from the produced water of the oil field, and the problems of unstable performance of the existing crosslinking agent, poor temperature resistance and shear resistance after crosslinking and the like are solved, so that the borate ester crosslinking agent has important practical significance.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, provides a borate ester crosslinking agent for preparing a guanidine gum fracturing fluid system from oilfield produced water, and solves the problems of unstable performance, poor temperature resistance and shear resistance after crosslinking and the like of the existing crosslinking agent, and a preparation method thereof.
The technical problem to be solved by the invention is realized by adopting the following technical scheme:
a preparation method of a borate ester cross-linking agent comprises the following steps of adding ethylene glycol into an ethanol solvent, uniformly stirring, slowly adding boric acid, wherein the molar ratio of the ethylene glycol to the boric acid is 1 (1.0-1.2), stirring and refluxing for 1-2h, and removing the ethanol solvent by a reduced pressure distillation method to obtain an intermediate;
mixing the intermediate and tetraethylenepentamine together, wherein the molar ratio of the tetraethylenepentamine to the intermediate is 1 (5.0-5.5), heating to 100-120 ℃, continuing to react, and cooling to room temperature to obtain the product, namely the borate ester crosslinking agent.
Wherein the reaction time of the tetraethylenepentamine and the intermediate is 3-5 h; and the heating rate of the reaction of the tetraethylenepentamine and the intermediate is controlled to be 2-5 ℃/min.
The corresponding borate ester cross-linking agent product can be prepared according to the preparation method of the borate ester cross-linking agent.
The invention has the advantages and positive effects that:
the borate ester crosslinking agent contains five borate ester groups, has the characteristics of controllable crosslinking time, small addition amount, good temperature resistance and shearing resistance of crosslinked jelly and the like, can be used for preparing fracturing fluid for crosslinking from produced water of an oil field, and effectively solves the two problems of environmental protection and water for fracturing.
Drawings
The technical solutions of the present invention will be described in further detail below with reference to the accompanying drawings and examples, but it should be understood that these drawings are designed for illustrative purposes only and thus do not limit the scope of the present invention. Furthermore, unless otherwise indicated, the drawings are intended to be illustrative of the structural configurations described herein and are not necessarily drawn to scale.
FIG. 1 is a rheology diagram of a borate ester crosslinker provided in example 3 of the present invention;
FIG. 2 is a graph of a modified shear for a boronate ester crosslinker provided in example 3 of the present invention;
FIG. 3 is a sand-carrying hanging chart of the borate ester cross-linking agent provided in example 3 of the present invention;
wherein, line A in FIG. 1 represents a temperature curve and line B represents a viscosity curve; the curve in figure 2 is the viscosity curve with shear rate on the abscissa.
Detailed Description
First, it should be noted that the specific structures, features, advantages, etc. of the present invention will be specifically described below by way of example, but all the descriptions are for illustrative purposes only and should not be construed as limiting the present invention in any way. Furthermore, any individual technical features described or implicit in the embodiments mentioned herein may still be continued in any combination or subtraction between these technical features (or their equivalents) to obtain still further embodiments of the invention that may not be mentioned directly herein.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present application. As used herein, the singular forms "a", "an", and "the" are intended to include the plural forms as well, and furthermore, the terms "comprises" and "having", and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements expressly listed, but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict.
The present invention will be specifically described with reference to fig. 1 to 3. Wherein:
example 1:
feeding molar ratio: the feeding molar ratio of the ethanol to the glycol to the boric acid is 1:1.0: 0.3. Adding ethanol and ethylene glycol into a three-neck flask according to the feeding ratio, uniformly stirring, slowly adding boric acid, stirring and refluxing for 1.5h, and then removing the solvent to obtain an intermediate;
and (3) uniformly mixing tetraethylenepentamine and the intermediate according to the feeding molar ratio of 1:5.0, heating to 100 ℃ at the speed of 2.5 ℃/min, continuously reacting for 3.5h, and cooling to room temperature to obtain the product, namely the boric acid ester crosslinking agent.
Example 2:
feeding molar ratio: the feeding molar ratio of the ethanol to the glycol to the boric acid is 1:1.0: 0.3. Adding ethanol and ethylene glycol into a three-neck flask according to the feeding ratio, uniformly stirring, slowly adding boric acid, stirring and refluxing for 1h, and then removing the solvent to obtain an intermediate;
and (3) uniformly mixing tetraethylenepentamine and the intermediate according to the feeding molar ratio of 1:5.2, heating to 110 ℃ at the speed of 2.5 ℃/min, continuing to react for 4h, and cooling to room temperature to obtain the product, namely the boric acid ester cross-linking agent.
Example 3:
feeding molar ratio: the feeding molar ratio of the ethanol to the glycol to the boric acid is 1:1.1: 0.4. Adding ethanol and ethylene glycol into a three-neck flask according to the feeding ratio, uniformly stirring, slowly adding boric acid, stirring and refluxing for 2 hours, and then removing the solvent to obtain an intermediate;
and (3) uniformly mixing tetraethylenepentamine and the intermediate according to the feeding molar ratio of 1:5.4, heating to 120 ℃ at the speed of 3.0 ℃/min, continuing to react for 3h, and cooling to room temperature to obtain the product, namely the boric acid ester cross-linking agent.
Example 4:
feeding molar ratio: the feeding molar ratio of the ethanol to the glycol to the boric acid is 1:1.2: 0.5. Adding ethanol and ethylene glycol into a three-neck flask according to the feeding ratio, uniformly stirring, slowly adding boric acid, stirring and refluxing for 1.5h, and then removing the solvent to obtain an intermediate;
and (3) uniformly mixing tetraethylenepentamine and the intermediate according to the feeding molar ratio of 1:5.5, heating to 110 ℃ at the speed of 4.0 ℃/min, continuing to react for 4h, and cooling to room temperature to obtain the product, namely the boric acid ester cross-linking agent.
Example 5:
feeding molar ratio: the feeding molar ratio of the ethanol to the glycol to the boric acid is 1:1.2: 0.4. Adding ethanol and ethylene glycol into a three-neck flask according to the feeding ratio, uniformly stirring, slowly adding boric acid, stirring and refluxing for 1h, and then removing the solvent to obtain an intermediate;
and (3) uniformly mixing tetraethylenepentamine and the intermediate according to the feeding molar ratio of 1:5.3, heating to 110 ℃ at the speed of 5.0 ℃/min, continuing to react for 5h, and cooling to room temperature to obtain the product, namely the boric acid ester cross-linking agent.
Example 6:
0.45 percent hydroxypropyl guar gum solution is prepared by using the produced water of the oil field, the pH value is adjusted to 10-11 by using sodium carbonate, the borate ester cross-linking agents prepared in the examples 1-5 are respectively added, the cross-linking ratio is 100:0.2, the performance evaluation is carried out according to the standard SY/T5107-2005 water-based fracturing fluid performance evaluation method, and the test results are shown in the following table 1.
TABLE 1
As can be seen from Table 1, the borate ester crosslinking agent of examples 1-5 of the present invention has a delayed crosslinking time of 45-70s at a crosslinking ratio of 100:0.2, has good delayed crosslinking ability, and the gel is colorless and transparent after crosslinking, and can be completely picked up, the viscosity is more than 100 mPa.s after shearing for 90min at 120 ℃, the requirement of more than 50 mPa.s specified in the general technical conditions of SY/T6376-2008 fracturing fluid is met, wherein the viscosity of the sheared product of the example 3 is maintained at 148 mPas, a rheogram, a shear-changed graph and a sand-carrying hanging graph of the example 3 are respectively shown in a figure 1, a figure 2 and a figure 3, a curve in the figure 2 represents that under the condition of 90 ℃, the viscosity of the fracturing fluid changes at different shear rates, so that the fracturing fluid has better shear recovery capability, and the cross-linking agent has better temperature resistance and shear resistance.
The present invention has been described in detail with reference to the above examples, but the description is only for the preferred examples of the present invention and should not be construed as limiting the scope of the present invention. All equivalent changes and modifications made within the scope of the present invention shall fall within the scope of the present invention.
Claims (4)
1. A preparation method of a borate ester crosslinking agent is characterized by comprising the following steps: comprises the following steps of (a) carrying out,
adding ethylene glycol into an ethanol solvent, uniformly stirring, slowly adding boric acid, wherein the molar ratio of the ethylene glycol to the boric acid is 1 (1.0-1.2), stirring and refluxing for 1-2h, and removing the ethanol solvent by a reduced pressure distillation method to obtain an intermediate;
mixing the intermediate and tetraethylenepentamine together, wherein the molar ratio of the tetraethylenepentamine to the intermediate is 1 (5.0-5.5), heating to 100-120 ℃, continuing to react, and cooling to room temperature to obtain the product, namely the borate ester crosslinking agent.
2. The method of preparing a boronate ester crosslinker of claim 1, wherein: the reaction time of the tetraethylenepentamine and the intermediate is 3-5 h.
3. The method of preparing a boronate ester crosslinker of claim 1, wherein: and the heating rate of the reaction of the tetraethylenepentamine and the intermediate is controlled to be 2-5 ℃/min.
4. A borate crosslinker product made by the method of making a borate crosslinker as claimed in any of claims 1-3.
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CN202011109669.6A CN112250703A (en) | 2020-10-16 | 2020-10-16 | Preparation method of borate crosslinking agent and product |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111675729A (en) * | 2020-06-19 | 2020-09-18 | 西安石油大学 | Crosslinking agent for fracturing flow-back fluid repeated fluid and preparation method and application thereof |
CN115433362A (en) * | 2022-09-21 | 2022-12-06 | 河北工业大学 | Preparation method of cross-linking agent for low-concentration temperature-resistant and shear-resistant guanidine gum |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130220621A1 (en) * | 2008-10-21 | 2013-08-29 | Baker Hughes Incorporated | Polyboronic Compounds and Processes of Making and Using the Same |
CN109280547A (en) * | 2017-07-20 | 2019-01-29 | 中国石油化工股份有限公司 | A kind of organic borate cross-linker and guar gum fracturing fluid |
CN109825276A (en) * | 2017-11-23 | 2019-05-31 | 中国石油化工股份有限公司 | A kind of aqueous fracturing fluid composition and aqueous fracturing fluid |
-
2020
- 2020-10-16 CN CN202011109669.6A patent/CN112250703A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20130220621A1 (en) * | 2008-10-21 | 2013-08-29 | Baker Hughes Incorporated | Polyboronic Compounds and Processes of Making and Using the Same |
CN109280547A (en) * | 2017-07-20 | 2019-01-29 | 中国石油化工股份有限公司 | A kind of organic borate cross-linker and guar gum fracturing fluid |
CN109825276A (en) * | 2017-11-23 | 2019-05-31 | 中国石油化工股份有限公司 | A kind of aqueous fracturing fluid composition and aqueous fracturing fluid |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111675729A (en) * | 2020-06-19 | 2020-09-18 | 西安石油大学 | Crosslinking agent for fracturing flow-back fluid repeated fluid and preparation method and application thereof |
CN111675729B (en) * | 2020-06-19 | 2023-07-14 | 西安石油大学 | Cross-linking agent for repeated liquid preparation of fracturing flowback liquid, and preparation method and application thereof |
CN115433362A (en) * | 2022-09-21 | 2022-12-06 | 河北工业大学 | Preparation method of cross-linking agent for low-concentration temperature-resistant and shear-resistant guanidine gum |
CN115433362B (en) * | 2022-09-21 | 2023-09-15 | 河北工业大学 | Preparation method of cross-linking agent for low-concentration temperature-resistant shearing-resistant guanidine gum |
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Application publication date: 20210122 |