CN105085804A - Polystyrene butenedioic acid dibenzyl ester and preparation method and application thereof - Google Patents
Polystyrene butenedioic acid dibenzyl ester and preparation method and application thereof Download PDFInfo
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- CN105085804A CN105085804A CN201510423112.2A CN201510423112A CN105085804A CN 105085804 A CN105085804 A CN 105085804A CN 201510423112 A CN201510423112 A CN 201510423112A CN 105085804 A CN105085804 A CN 105085804A
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- Prior art keywords
- dibenzyl ester
- acid dibenzyl
- polystyrene
- preparation
- dioic acid
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims abstract description 46
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 239000004793 Polystyrene Substances 0.000 title claims abstract description 43
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 239000000700 radioactive tracer Substances 0.000 claims abstract description 28
- 238000012544 monitoring process Methods 0.000 claims abstract description 19
- 239000004342 Benzoyl peroxide Substances 0.000 claims abstract description 17
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims abstract description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 235000019400 benzoyl peroxide Nutrition 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002612 dispersion medium Substances 0.000 claims abstract description 3
- 239000000178 monomer Substances 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 46
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 23
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 23
- -1 polyoxyethylene Polymers 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 abstract description 31
- 239000010779 crude oil Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000007788 liquid Substances 0.000 abstract description 3
- CPZVJYPXOWWFSW-UHFFFAOYSA-N dibenzyl but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)C=CC(=O)OCC1=CC=CC=C1 CPZVJYPXOWWFSW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- CPZVJYPXOWWFSW-QXMHVHEDSA-N dibenzyl (z)-but-2-enedioate Chemical compound C=1C=CC=CC=1COC(=O)\C=C/C(=O)OCC1=CC=CC=C1 CPZVJYPXOWWFSW-QXMHVHEDSA-N 0.000 description 14
- 239000002245 particle Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000007599 discharging Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000010696 ester oil Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000004313 potentiometry Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Abstract
The invention provides polystyrene butenedioic acid dibenzyl ester and a preparation method and application thereof. The preparation method comprises the steps of taking styrene and dibenzyl butenedioate as reaction monomers, and carrying out polymerization reaction by taking water as a dispersion medium in the presence of polyethylene glycol and benzoyl peroxide to obtain the polystyrene dibenzyl butenedioate. The invention also provides polystyrene butenedioic acid dibenzyl ester prepared by the preparation method, application of the polystyrene butenedioic acid dibenzyl ester in preparing a tracer for monitoring the oil production profile of a horizontal well, and the tracer containing the polystyrene butenedioic acid dibenzyl ester for monitoring the oil production profile of the horizontal well. The polystyrene butenedioic acid dibenzyl ester can be completely dissolved in crude oil, and can be used for monitoring the oil production condition of each section of a horizontal well after multi-stage fracturing, so that the purposes of analyzing the oil production condition of each section and drawing the oil production liquid profile of each section can be achieved.
Description
Technical field
The present invention relates to a kind of polystyrene butene dioic acid dibenzyl ester and preparation method thereof and application, belong to petroleum exploration and development technical field.
Background technology
At present in In Oil Field Exploration And Development process, prospect pit many employings horizontal well, and multi-layer multi-stage pressure break is the first-selected technique of stratum transformation, but in the process that layer position is selected, there is no specific aim, be all by experience to select layering, therefore post-fracturing Data acquisition and issuance fracturing effect just seemed particularly important.In prior art, by the monitoring of the method such as micro seismic method, potentiometry and fracture intensity after pressure break can be analyzed, more whether have commercial oil by the row's of returning situation awareness reservoir, but effective monitoring method is not still had for the produce oil situation of each section after staged fracturing.
Therefore, after developing a kind of level monitoring well multistage fracturing, the processing method of each section of produce oil situation has great importance to the evaluation of fracturing effect and the deployment of next step well location.
Multistage fracturing technique building technology and relevant support equipment ripe, realized 30 grades of pressure breaks in the world, largest domestic pressure break progression is more than 15 grades.Because pressure break progression is more, in addition at long horizontal sections, physical property there are differences, and after every grade of pressure break, discharge opeing situation has great importance for the evaluation of fracturing effect and next step well site deployment, but does not have effective monitoring method for the produce oil situation of each section after staged fracturing.Because current largest domestic pressure break progression is more than 15 grades, correspondingly need the horizontal well produce oil profile monitoring tracer agent of more than 15 kinds.Existing oil field tracer agent is water-soluble tracer, and the kind of tracer agent is few, consumption is large, is not suitable for the monitoring of each section of produce oil situation after horizontal well multi-layer multi-stage pressure break.
Therefore, develop a kind of suitable horizontal well produce oil profile monitoring tracer agent and become the technical problem that this area needs solution badly.
Summary of the invention
For solving the problems of the technologies described above, the object of the present invention is to provide a kind of preparation method of polystyrene butene dioic acid dibenzyl ester.
The present invention also aims to provide a kind of polystyrene butene dioic acid dibenzyl ester prepared by the preparation method of above-mentioned polystyrene butene dioic acid dibenzyl ester.
The present invention also aims to provide a kind of above-mentioned polystyrene butene dioic acid dibenzyl ester in the application preparing horizontal well produce oil profile monitoring tracer agent.
The present invention also aims to provide a kind of horizontal well produce oil profile monitoring tracer agent comprising above-mentioned polystyrene butene dioic acid dibenzyl ester.
For reaching above-mentioned purpose, the invention provides a kind of preparation method of polystyrene butene dioic acid dibenzyl ester, the method comprises with vinylbenzene and butene dioic acid dibenzyl ester for reaction monomers, under the existence of polyoxyethylene glycol and benzoyl peroxide, be that dispersion medium carries out polyreaction with water, obtain described polystyrene butene dioic acid dibenzyl ester;
Wherein, polyoxyethylene glycol is dispersion agent, and benzoyl peroxide is initiator.
Wherein said butene dioic acid dibenzyl ester ((CHCOOCH
2c
6h
5)
2), polyoxyethylene glycol (HO (CH
2cH
2o) nH), vinylbenzene (C
8h
8) and benzoyl peroxide (C
6h
5c (O) O
2) being the conventional reagent of this area, conventional butene dioic acid dibenzyl ester, polyoxyethylene glycol, vinylbenzene and the benzoyl peroxide in any commercially available this area may be used to the present invention.
Described butene dioic acid dibenzyl ester both can be the ester that maleic acid and benzylalcohol are formed, and also can be the ester that FUMARIC ACID TECH GRADE and benzylalcohol are formed;
The molecular-weight average of above-mentioned polyoxyethylene glycol is 3600-4400, and wherein, molecular-weight average is sticky equal molecular-weight average.
According to preparation method of the present invention, preferably, the whole material gross weights added in reaction are for 100%, institute adds each weight of material per-cent and is respectively: butene dioic acid dibenzyl ester is 35wt%-45wt%, vinylbenzene is 2.5wt%-5wt%, polyoxyethylene glycol is 1wt%-1.5wt%, benzoyl peroxide is 0.2wt%-0.9wt%, and surplus is water.
According to preparation method of the present invention, preferably, the temperature of reaction of described polyreaction is 80 DEG C-90 DEG C, and more preferably described temperature of reaction is 85 DEG C.
According to preparation method of the present invention, preferably, the reaction times of described polyreaction is 8-10h, and more preferably the described reaction times is 10h.
In the preparation process of polystyrene butene dioic acid dibenzyl ester of the present invention, the change of temperature of reaction and time is little on its impact, as long as control temperature of reaction at 80 DEG C-90 DEG C, the reaction times controls at 8-10h.
According to preparation method of the present invention, preferably, described method comprises: first polyoxyethylene glycol is dissolved in water, adds the mixing solutions of butene dioic acid dibenzyl ester, vinylbenzene and benzoyl peroxide, is obtained by reacting described polystyrene butene dioic acid dibenzyl ester after having added.
According to preparation method of the present invention, preferably, described method comprises: first polyoxyethylene glycol is dissolved in 80 DEG C of-90 DEG C of hot water, then adds the mixing solutions of butene dioic acid dibenzyl ester, vinylbenzene and benzoyl peroxide.
According to preparation method of the present invention, preferably, described method comprises: first polyoxyethylene glycol is dissolved in water, is warmed up to 80 DEG C-90 DEG C constant temperature 20-30min, then adds the mixing solutions of butene dioic acid dibenzyl ester, vinylbenzene and benzoyl peroxide.
According to preparation method of the present invention, preferably, dropping is incorporated as described in; More preferably, the speed of dropping is that 5-10 drips/min, and rate of addition is too fast easily causes sticky still.
According to preparation method of the present invention, preferably, described method also comprises: after being obtained by reacting described polystyrene butene dioic acid dibenzyl ester, be cooled to room temperature discharging again.
Present invention also offers the polystyrene butene dioic acid dibenzyl ester prepared by the preparation method of above-mentioned polystyrene butene dioic acid dibenzyl ester.
Present invention also offers above-mentioned polystyrene butene dioic acid dibenzyl ester in the application preparing horizontal well produce oil profile monitoring tracer agent.
According to application of the present invention; in multistage fracturing process; different types of solid oil dissolubility tracer particles is mixed in every section of fracturing propping agents; along with the output of crude oil; solid oil dissolubility tracer particles can constantly be dissolved in crude oil; by analyzing the concentration of tracer agent in production fluid, just can reach and analyzing every section of produce oil situation and the object of drawing every section of produce oil liquid section.
Present invention also offers a kind of horizontal well produce oil profile monitoring tracer agent, this tracer agent comprises above-mentioned polystyrene butene dioic acid dibenzyl ester.
The horizontal well produce oil profile monitoring tracer agent prepared by polystyrene butene dioic acid dibenzyl ester of the present invention is oil soluble tracer agent, and it can be dissolved in crude oil completely, and when concentration is low, accuracy of detection is high, and consumption is low.In multistage fracturing process, every section is mixed into different types of solid oil dissolubility tracer particles in fracturing propping agents, along with the output of crude oil, solid oil dissolubility tracer particles is constantly dissolved in crude oil, by analyzing the concentration of polystyrene butene dioic acid dibenzyl ester tracer agent in production fluid, can reach and analyze every section of produce oil situation and the object of drawing every section of produce oil liquid section.
Embodiment
The beneficial effect of implementation process of the present invention and generation will be explained by specific embodiment below, be intended to help reader to understand essence of the present invention and feature better, but not as can the restriction of practical range to this case.
Embodiment 1
Present embodiments provide a kind of preparation method of polystyrene maleic acid dibenzyl ester, it comprises the following steps:
A, 1.0g polyoxyethylene glycol (PEG4000) is dissolved in the hot water of 50g, is warmed up to 85 DEG C of constant temperature 30min, obtains the aqueous solution of polyoxyethylene glycol;
B, again with 5-10 drip/speed of min slowly drips the mixing solutions of 45g maleic acid dibenzyl ester, 4.5g vinylbenzene and 0.9g benzoyl peroxide in the aqueous solution of above-mentioned polyoxyethylene glycol, be added dropwise to complete rear reaction 10h, be cooled to room temperature discharging, obtain polystyrene maleic acid dibenzyl ester, its particle diameter is 0.600mm-0.850mm (20 order-30 order).
Embodiment 2
Present embodiments provide a kind of preparation method of polystyrene maleic acid dibenzyl ester, it comprises the following steps:
A, 1.3g polyoxyethylene glycol (PEG4000) is dissolved in the hot water of 55g, is warmed up to 85 DEG C of constant temperature 30min, obtains the aqueous solution of polyoxyethylene glycol;
B, again with 5-10 drip/speed of min drips the mixing solutions of 40g maleic acid dibenzyl ester, 4g vinylbenzene and 0.8g benzoyl peroxide in the aqueous solution of above-mentioned polyoxyethylene glycol, be added dropwise to complete rear reaction 10h, be cooled to room temperature discharging, obtain polystyrene maleic acid dibenzyl ester, its particle diameter is 0.180mm-0.425mm (40 order-80 order).
Embodiment 3
Present embodiments provide a kind of preparation method of polystyrene maleic acid dibenzyl ester, it comprises the following steps:
A, 1.5g polyoxyethylene glycol (PEG4000) is dissolved in the hot water of 60g, is warmed up to 85 DEG C of constant temperature 30min, obtains the aqueous solution of polyoxyethylene glycol;
B, again with 5-10 drip/speed of min drips the mixing solutions of 35g maleic acid dibenzyl ester, 3.5g vinylbenzene and 0.7g benzoyl peroxide in the aqueous solution of above-mentioned polyoxyethylene glycol, be added dropwise to complete rear reaction 10h, be cooled to room temperature discharging, obtain polystyrene maleic acid dibenzyl ester, its particle diameter is 0.150mm-0.250mm (60 order-100 order).
Embodiment 4
Present embodiments provide polystyrene maleic acid dibenzyl ester that above-described embodiment 1, embodiment 2 and embodiment 3 prepare in the application preparing horizontal well produce oil profile monitoring tracer agent, this application process can each section of produce oil situation after level monitoring well multistage fracturing, and it comprises the following steps:
Respectively by 0.1g embodiment 1, the polystyrene maleic acid dibenzyl ester oil soluble tracer agent that embodiment 2 and embodiment 3 prepare is dissolved in 100g emerging buried hill block crude oil, be warmed up to 70 DEG C to make tracer agent dissolution rate raising in a solvent, shorten evaluation time, after polystyrene maleic acid dibenzyl ester oil soluble tracer agent dissolves mix completely, get the above-mentioned mixed solution of 1g, sherwood oil is used to dilute 20 times, use the content of polystyrene maleic acid dibenzyl ester oil soluble tracer agent in gas chromatograph-mass spectrometer working sample again, test result is as shown in table 1.
Polystyrene maleic acid dibenzyl ester measurement result in table 1 sample
Claims (10)
1. the preparation method of a polystyrene butene dioic acid dibenzyl ester, wherein, described method comprises with vinylbenzene and butene dioic acid dibenzyl ester for reaction monomers, under the existence of polyoxyethylene glycol and benzoyl peroxide, be that dispersion medium carries out polyreaction with water, obtain described polystyrene butene dioic acid dibenzyl ester.
2. preparation method according to claim 1, wherein, the whole material gross weights added in reaction are for 100%, institute adds each weight of material per-cent and is respectively: butene dioic acid dibenzyl ester is 35wt%-45wt%, vinylbenzene is 2.5wt%-5wt%, polyoxyethylene glycol is 1wt%-1.5wt%, benzoyl peroxide is 0.2wt%-0.9wt%, and surplus is water.
3. preparation method according to claim 1 and 2, wherein, the temperature of reaction of described polyreaction is 80 DEG C-90 DEG C.
4. preparation method according to claim 1 and 2, wherein, the temperature of reaction of described polyreaction is 8-10h.
5. preparation method according to claim 1 and 2, wherein, described method comprises: first polyoxyethylene glycol is dissolved in water, adds the mixing solutions of butene dioic acid dibenzyl ester, vinylbenzene and benzoyl peroxide, is obtained by reacting described polystyrene butene dioic acid dibenzyl ester after having added;
Dropping is incorporated as preferably; The speed of preferred dropping is that 5-10 drips/min.
6. preparation method according to claim 5, wherein, described method comprises: first polyoxyethylene glycol is dissolved in 80 DEG C of-90 DEG C of hot water, then adds the mixing solutions of butene dioic acid dibenzyl ester, vinylbenzene and benzoyl peroxide.
7. preparation method according to claim 5, wherein, described method comprises: first polyoxyethylene glycol is dissolved in water, is warmed up to 80 DEG C-90 DEG C constant temperature 20-30min, then adds the mixing solutions of butene dioic acid dibenzyl ester, vinylbenzene and benzoyl peroxide.
8. the polystyrene butene dioic acid dibenzyl ester that the preparation method of the polystyrene butene dioic acid dibenzyl ester described in any one of claim 1-7 prepares.
9. polystyrene butene dioic acid dibenzyl ester according to claim 8 is in the application preparing horizontal well produce oil profile monitoring tracer agent.
10. a horizontal well produce oil profile monitoring tracer agent, wherein, this tracer agent comprises polystyrene butene dioic acid dibenzyl ester according to claim 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510423112.2A CN105085804B (en) | 2015-07-17 | 2015-07-17 | Polystyrene butenedioic acid dibenzyl ester and preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510423112.2A CN105085804B (en) | 2015-07-17 | 2015-07-17 | Polystyrene butenedioic acid dibenzyl ester and preparation method and application thereof |
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| Publication Number | Publication Date |
|---|---|
| CN105085804A true CN105085804A (en) | 2015-11-25 |
| CN105085804B CN105085804B (en) | 2018-02-02 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795845A1 (en) * | 1964-06-27 | 1976-11-25 | Texaco Ag | METHOD FOR MANUFACTURING THERMOPLASTIC COPOLYMERIZES FROM STYRENE AND FUMAR ACID ESTERS OF SECONDARY ALCOHOLS |
| CN103752289A (en) * | 2014-01-26 | 2014-04-30 | 福州大学 | Organic solvent absorbing agent and preparation method thereof |
| CN104018822A (en) * | 2014-05-23 | 2014-09-03 | 中国石油化工股份有限公司江汉油田分公司采油工艺研究院 | Oil well staged fracturing effect monitoring method |
-
2015
- 2015-07-17 CN CN201510423112.2A patent/CN105085804B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795845A1 (en) * | 1964-06-27 | 1976-11-25 | Texaco Ag | METHOD FOR MANUFACTURING THERMOPLASTIC COPOLYMERIZES FROM STYRENE AND FUMAR ACID ESTERS OF SECONDARY ALCOHOLS |
| CN103752289A (en) * | 2014-01-26 | 2014-04-30 | 福州大学 | Organic solvent absorbing agent and preparation method thereof |
| CN104018822A (en) * | 2014-05-23 | 2014-09-03 | 中国石油化工股份有限公司江汉油田分公司采油工艺研究院 | Oil well staged fracturing effect monitoring method |
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