CN105085794B - Polystyrene acrylic acid-2-hydroxypropyl ester and synthetic method and application thereof - Google Patents
Polystyrene acrylic acid-2-hydroxypropyl ester and synthetic method and application thereof Download PDFInfo
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- CN105085794B CN105085794B CN201510422346.5A CN201510422346A CN105085794B CN 105085794 B CN105085794 B CN 105085794B CN 201510422346 A CN201510422346 A CN 201510422346A CN 105085794 B CN105085794 B CN 105085794B
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- styrene
- polyethylene glycol
- tracer
- water
- azodiisobutyronitrile
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 14
- 239000004793 Polystyrene Substances 0.000 title abstract description 24
- 229920002223 polystyrene Polymers 0.000 title abstract description 24
- AYEFIAVHMUFQPZ-UHFFFAOYSA-N propane-1,2-diol;prop-2-enoic acid Chemical compound CC(O)CO.OC(=O)C=C AYEFIAVHMUFQPZ-UHFFFAOYSA-N 0.000 title abstract description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 26
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000012544 monitoring process Methods 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 4
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 31
- 239000000700 radioactive tracer Substances 0.000 claims description 26
- 239000011259 mixed solution Substances 0.000 claims description 9
- 238000010792 warming Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229920001909 styrene-acrylic polymer Polymers 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 16
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000010779 crude oil Substances 0.000 abstract description 5
- 238000012360 testing method Methods 0.000 abstract description 3
- 239000002270 dispersing agent Substances 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract description 2
- 239000002612 dispersion medium Substances 0.000 abstract 1
- 238000010557 suspension polymerization reaction Methods 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 16
- 239000002245 particle Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 5
- 238000007599 discharging Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UAGJVSRUFNSIHR-UHFFFAOYSA-N Methyl levulinate Chemical compound COC(=O)CCC(C)=O UAGJVSRUFNSIHR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ONJMNXFNTYIEEA-UHFFFAOYSA-N benzene ethene Chemical compound C1=CC=CC=C1.C=C.C=C.C=C ONJMNXFNTYIEEA-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- -1 hydroxy propyl esters Chemical class 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 238000004313 potentiometry Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention provides a polystyrene acrylic acid-2-hydroxypropyl ester and a synthetic method and application thereof. The polystyrene acrylic acid-2-hydroxypropyl ester is prepared by the method comprising the following steps: acrylic acid-2-hydroxypropyl ester and styrene are taken as reaction monomers, and suspension polymerization reaction is carried out by taking water as a dispersion medium in the presence of dispersant polyethylene glycol and initiator azobisisobutyronitrile. The polystyrene acrylic acid-2-hydroxypropyl ester has the following advantages: the test result shows that the polystyrene acrylic acid-2-hydroxypropyl ester prepared by the synthetic method can be completely dissolved in the crude oil, the concentration of the polystyrene acrylic acid-2-hydroxypropyl ester can be accurately measured by a gas chromatograph-mass spectrometer, the using amount is small, and the requirement of monitoring the oil production section of the horizontal well is met.
Description
Technical field
The present invention relates to oil exploration and development fields, specifically, are related to a kind of polystyrene acrylic acid -2- hydroxy propyl esters
And its synthetic method and application.
Background technology
At present during In Oil Field Exploration And Development, prospect pit uses horizontal well more, and multi-layer multi-stage pressure break is stratum transformation
Preferred technique, but during layer position selects, be all to select to be layered by experience without specific aim, thus for pressure break after
Data acquisition and issuance fracturing effect be just particularly important.In the prior art, can be supervised by micro seismic method, potentiometry etc.
Fracture intensity after pressure break is surveyed and analyzed, whether has commercial oil by the row's of returning situation awareness reservoir, but for staged fracturing
Each section of oil-producing situation does not have effective monitoring method afterwards.
Multistage fracturing technique building technology and corollary equipment are ripe, have realized 30 grades of pressure breaks, largest domestic in the world
Pressure break series is more than 15 grades.Because pressure break series is more, long horizontal sections physical property has differences in addition, discharge opeing feelings after every grade of pressure break
Evaluation and next step well site deployment of the condition for fracturing effect have great importance, but for each section after staged fracturing of oil-producing
Situation does not have effective monitoring method.To solve the technical problem, during multistage fracturing, every section is mixed in fracturing propping agents
Enter different types of solid oil-soluble tracer particles, be constantly dissolved in original with the output solid oil-soluble tracer particles of crude oil
In oil, by analyzing the concentration of tracer in production fluid, reach the mesh that every section of oil-producing situation of analysis draws every section of oil-producing liquid section
's.Because current largest domestic pressure break series is more than 15 grades, therefore mutually in requisition for 15 kinds of level above well oil-producing profile monitorings
Use tracer.
Conventional oil field is water solubility with tracer, and the few dosage of species is big, is not suitable for horizontal well multi-layer multi-stage pressure
The monitoring of rear each section of oil-producing situation is split, tracer of the present invention is oil-soluble, and accuracy of detection is high when concentration is low, and dosage is low.
During multistage fracturing, every section is mixed into different types of solid oil-soluble tracer particles in fracturing propping agents, with original
The output solid oil-soluble tracer particles of oil are constantly dissolved in crude oil, by analyzing the concentration of tracer in production fluid, are reached
Analyze the purpose that every section of oil-producing situation draws every section of oil-producing liquid section.
The content of the invention
It is an object of the present invention to provide a kind of synthetic method of polystyrene acrylic acid -2- hydroxy propyl esters；
Polystyrene acrylic acid -2- the hydroxyls third being prepared another object of the present invention is to provide the synthetic method
Ester；
It is still another object of the present invention to provide described polystyrene acrylic acid -2- hydroxy propyl esters to prepare horizontal well production
The application of oily profile monitoring tracer；
A further object of the present invention is to provide the horizontal well production containing described polystyrene acrylic acid -2- hydroxy propyl esters
Oily profile monitoring tracer.
For the above-mentioned purpose, on the one hand, the invention provides a kind of synthesis side of polystyrene acrylic acid -2- hydroxy propyl esters
Method, methods described is included using 2-hydroxypropyl acrylate and styrene as reaction monomers, in polyethylene glycol and azodiisobutyronitrile
In the presence of, carry out polymerisation by decentralized medium of water.
Polyethylene glycol therein is dispersant, and azodiisobutyronitrile is initiator.
Wherein described 2-hydroxypropyl acrylate (C6H10O3), azodiisobutyronitrile (C8H12N4), styrene (C8H8) and
Polyethylene glycol (HO (CH2CH2O) nH) it is this area conventional reagent, any commercially available methyl acrylate commonly used in the art, azo two
Isobutyronitrile, styrene and polyethylene glycol may be used to the present invention.
According to some preferred embodiments of the invention, described polyethylene glycol is the poly- of viscosity average molecular weigh 3600-4400
Ethylene glycol.
According to some preferred embodiments of the invention, in described synthetic method, to react the whole things added
It is 100% meter to expect gross weight, and adding each weight of material percentage is respectively：2-hydroxypropyl acrylate is 25-45%, benzene
Ethene is 2.5-5%, polyethylene glycol 0.1-0.2%, azodiisobutyronitrile 0.5-1% and water are 50-70%.
According to some of the invention preferred embodiments, the reaction temperature of polymerisation of the present invention can be 70 DEG C~
80℃；Wherein it is preferably 75 DEG C.
According to some preferred embodiments of the invention, the reaction time of the polymerisation can be 8-10h；It is wherein excellent
Elect 8h as.
According to some preferred embodiments of the invention, methods described includes：Polyethylene glycol is dissolved into water first, added
Enter the mixed solution of 2-hydroxypropyl acrylate, styrene and azodiisobutyronitrile, reacted after the completion of addition and obtain the polyphenyl
Ethylene acrylic -2- hydroxy propyl esters.
According to some preferred embodiments of the invention, methods described includes：First polyethylene glycol be dissolved into 70 DEG C~
In 80 DEG C of water, the mixed solution of 2-hydroxypropyl acrylate, styrene and azodiisobutyronitrile is added.
According to some preferred embodiments of the invention, methods described includes：Polyethylene glycol is dissolved into water first, risen
For temperature to 70 DEG C~80 DEG C constant temperature 30min, the mixing for adding 2-hydroxypropyl acrylate, styrene and azodiisobutyronitrile is molten
Liquid.
According to some preferred embodiments of the invention, methods described includes：Polyethylene glycol is dissolved into water first, risen
Temperature is to 75 DEG C of constant temperature 30min.
It is described to be incorporated as being added dropwise according to some preferred embodiments of the invention；
According to some preferred embodiments of the invention, the speed of the dropwise addition is 5-10 drops/min.
According to some preferred embodiments of the invention, methods described also includes：The polystyrene third is obtained in reaction
After olefin(e) acid -2- hydroxy propyl esters, it is cooled to room temperature and discharges again.
The present invention provides a kind of synthetic method of oil-soluble tracer polystyrene acrylic acid -2- hydroxy propyl esters, with weight
Percentages, 0.1%~0.2% polyethylene glycol is dissolved into 50%~70% hot water first, is warming up to 70 DEG C~80
DEG C constant temperature 30min, 25%~45% 2-hydroxypropyl acrylate, 2.5%~5% benzene are added dropwise with the speed of per minute 5~10 drops
The mixed solution of ethene and 0.5%~1% azodiisobutyronitrile, 8h~10h is reacted after being added dropwise to complete, be cooled to room temperature discharging.
On the other hand, present invention also offers the polystyrene third that synthetic method described in any one of the present invention is prepared
Olefin(e) acid -2- hydroxy propyl esters.
Another further aspect, present invention also offers described polystyrene acrylic acid -2- hydroxy propyl esters to prepare horizontal well production
The application of oily profile monitoring tracer.
Another aspect, present invention also offers the production of the horizontal well containing described polystyrene acrylic acid -2- hydroxy propyl esters
Oily profile monitoring tracer.
In summary, the invention provides a kind of polystyrene acrylic acid -2- hydroxy propyl esters and its synthetic method and application.
Polystyrene acrylic acid -2- the hydroxy propyl esters of the present invention have the following advantages that：
Test result shows can be complete using the polystyrene acrylic acid -2- hydroxy propyl esters that the synthetic method of the present invention is produced
Fully dissolved into crude oil, by gas chromatograph-mass spectrometer can Accurate Determining its concentration, dosage is few, meets horizontal well oil-producing profile monitoring
Needs.
Embodiment
The implementation process of the present invention and caused beneficial effect are described in detail below by way of specific embodiment, it is intended to which help is read
Reader more fully understand the present invention essence and feature, not as to this case can practical range restriction.
Embodiment 1
0.1g polyethylene glycol (PEG4000 mean molecule quantities 3600~4400) is dissolved into 55g hot water, is warming up to 75
DEG C constant temperature 30min, the mixing that 40g 2-hydroxypropyl acrylates, 4g styrene and 0.9g azodiisobutyronitriles is slowly added dropwise are molten
Liquid, 8h is reacted after being added dropwise to complete, be cooled to room temperature discharging.Obtain that particle diameter is 0.425mm-0.850mm (mesh of 20 mesh -40)
Grain.
Embodiment 2：
0.15g polyethylene glycol (PEG4000 mean molecule quantities 3600~4400) is dissolved into 60g hot water, is warming up to
75 DEG C of constant temperature 30min, are slowly added dropwise the mixing of 35g 2-hydroxypropyl acrylates, 3.5g styrene and 0.8g azodiisobutyronitriles
Solution, 8h is reacted after being added dropwise to complete, be cooled to room temperature discharging.Obtain that particle diameter is 0.425mm-0.212mm (mesh of 40 mesh -70)
Grain.
Embodiment 3：
0.2g polyethylene glycol (PEG4000 mean molecule quantities 3600~4400) is dissolved into 65g hot water, is warming up to 75
DEG C constant temperature 30min, the mixing that 30g 2-hydroxypropyl acrylates, 3g styrene and 0.6g azodiisobutyronitriles is slowly added dropwise are molten
Liquid, 8h is reacted after being added dropwise to complete, be cooled to room temperature discharging.Obtain that particle diameter is 0.212mm-0.090mm (mesh of 70 mesh -170)
Grain.
Application examples 1
0.1g polystyrene acrylic acid -2- hydroxy propyl esters prepared by embodiment 1 are dissolved in 100g crude oil, are warming up to 70 DEG C
1g is taken to dilute 20 times with petroleum ether after being completely dissolved and being well mixed, with polystyrene propylene in gas chromatograph-mass spectrometer determination sample
Acid -2- hydroxy propyl ester contents, test result are shown in Table 1.
Polystyrene acrylic acid -2- hydroxy propyl ester measurement results in the sample of table 1
Claims (17)
1. a kind of horizontal well oil-producing profile monitoring tracer, it is characterised in that the synthetic method of the tracer is included with third
Olefin(e) acid -2- hydroxy propyl esters and styrene are reaction monomers, in the presence of polyethylene glycol and azodiisobutyronitrile, are situated between using water to be scattered
Matter carries out polymerisation, is counted using reacting the whole material gross weights added as 100%, adds each weight of material percentage score
It is not：2-hydroxypropyl acrylate is 25-45%, styrene 2.5-5%, polyethylene glycol 0.1-0.2%, azo two are different
Butyronitrile is 0.5-1%, surplus is water.
2. tracer according to claim 1, it is characterised in that the reaction temperature of the polymerisation is 70 DEG C~80
℃。
3. tracer according to claim 1, it is characterised in that the reaction time of the polymerisation is 8-10h.
4. tracer according to claim 1, it is characterised in that methods described includes：Polyethylene glycol is dissolved into first
In water, the mixed solution of 2-hydroxypropyl acrylate, styrene and azodiisobutyronitrile is added, reacts and obtains after the completion of addition
The tracer.
5. tracer according to claim 4, it is characterised in that described to be incorporated as being added dropwise.
6. tracer according to claim 5, it is characterised in that the speed of dropwise addition is 5-10 drops/min.
7. tracer according to claim 4, it is characterised in that methods described includes：Polyethylene glycol is dissolved into first
In 70-80 DEG C of water, the mixed solution of 2-hydroxypropyl acrylate, styrene and azodiisobutyronitrile is added.
8. tracer according to claim 4, it is characterised in that methods described includes：Polyethylene glycol is dissolved into first
In water, 70 DEG C~80 DEG C constant temperature 20-30min are warming up to, add 2-hydroxypropyl acrylate, styrene and the isobutyl of azo two
The mixed solution of nitrile.
9. the preparation method of the tracer described in claim 1~8 any one, methods described is included with acrylic acid -2- hydroxyls
Propyl ester and styrene are reaction monomers, in the presence of polyethylene glycol and azodiisobutyronitrile, are polymerize by decentralized medium of water
Reaction.
Poly- 10. (styrene acrylic -2- hydroxy propyl esters) is preparing the application of horizontal well oil-producing profile monitoring tracer, described
The synthetic method of poly- (styrene acrylic -2- hydroxy propyl esters) includes single as reaction using 2-hydroxypropyl acrylate and styrene
Body, in the presence of polyethylene glycol and azodiisobutyronitrile, polymerisation is carried out by decentralized medium of water, is added with reaction complete
Portion's material gross weight is 100% meter, and adding each weight of material percentage is respectively：2-hydroxypropyl acrylate is 25-
45%th, styrene 2.5-5%, polyethylene glycol 0.1-0.2%, azodiisobutyronitrile 0.5-1%, surplus are water.
11. application according to claim 10, it is characterised in that the reaction temperature of the polymerisation is 70 DEG C~80
℃。
12. application according to claim 10, it is characterised in that the reaction time of the polymerisation is 8-10h.
13. application according to claim 10, it is characterised in that methods described includes：Polyethylene glycol is dissolved into first
In water, the mixed solution of 2-hydroxypropyl acrylate, styrene and azodiisobutyronitrile is added, reacts and obtains after the completion of addition
Poly- (styrene acrylic -2- hydroxy propyl esters).
14. application according to claim 12, it is characterised in that described to be incorporated as being added dropwise.
15. application according to claim 14, it is characterised in that the speed of dropwise addition is 5-10 drops/min.
16. application according to claim 13, it is characterised in that methods described includes：Polyethylene glycol is dissolved into first
In 70-80 DEG C of water, the mixed solution of 2-hydroxypropyl acrylate, styrene and azodiisobutyronitrile is added.
17. application according to claim 13, it is characterised in that methods described includes：Polyethylene glycol is dissolved into first
In water, 70 DEG C~80 DEG C constant temperature 20-30min are warming up to, add 2-hydroxypropyl acrylate, styrene and the isobutyl of azo two
The mixed solution of nitrile.
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| 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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| US5342877A (en) * | 1992-07-06 | 1994-08-30 | Eastman Chemical Company | Blends of polyesters and alkylhydroxy (meth)acrylate compounds |
| JP4967324B2 (en) * | 2005-11-28 | 2012-07-04 | 富士ゼロックス株式会社 | Hydroxyl group-containing magnetic polymer and method for producing the same |
| CN101538339B (en) * | 2009-04-23 | 2011-01-05 | 杭州精彩化工有限公司 | Preparation method of fluorescent pigment latex |
| CN102649826A (en) * | 2011-02-25 | 2012-08-29 | 常州均益新材料科技有限公司 | Preparation method of particle diameter controllable monodisperse polystyrene microspheres |
| CN102505566A (en) * | 2011-11-22 | 2012-06-20 | 上海东升新材料有限公司 | Pre-coating liquor for blueprint paper and preparation method thereof |
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| 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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| "丙烯酸-β-羟丙酯存在下无皂白交联型聚苯乙烯胶乳的合成与表征";戴李宗等;《高等学校化学学报》;19930928;第14卷(第9期);第1312-1316页 * |
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