CN116004212B - CO (carbon monoxide) 2 Crude oil amphiphilic chemical agent and its preparation method and CO improvement 2 Method for driving recovery ratio - Google Patents
CO (carbon monoxide) 2 Crude oil amphiphilic chemical agent and its preparation method and CO improvement 2 Method for driving recovery ratio Download PDFInfo
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- CN116004212B CN116004212B CN202111230135.3A CN202111230135A CN116004212B CN 116004212 B CN116004212 B CN 116004212B CN 202111230135 A CN202111230135 A CN 202111230135A CN 116004212 B CN116004212 B CN 116004212B
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- 239000010779 crude oil Substances 0.000 title claims abstract description 91
- 239000013043 chemical agent Substances 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000011084 recovery Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims description 27
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 title claims description 3
- 230000006872 improvement Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 61
- 239000000126 substance Substances 0.000 claims abstract description 41
- 238000002347 injection Methods 0.000 claims abstract description 22
- 239000007924 injection Substances 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 6
- -1 hydrocarbon radicals Chemical class 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 57
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 238000006073 displacement reaction Methods 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 19
- 229920000570 polyether Polymers 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 239000006184 cosolvent Substances 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002430 hydrocarbons Chemical group 0.000 claims description 6
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 5
- 229940017219 methyl propionate Drugs 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 4
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims description 4
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 3
- 239000011736 potassium bicarbonate Substances 0.000 claims description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 claims description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 2
- FUZLRTGGPPIBJQ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetramethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=NC(N(C)C)=N1 FUZLRTGGPPIBJQ-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 claims description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229940072049 amyl acetate Drugs 0.000 claims description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
- 229940043232 butyl acetate Drugs 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- NFKGQHYUYGYHIS-UHFFFAOYSA-N dibutyl propanedioate Chemical compound CCCCOC(=O)CC(=O)OCCCC NFKGQHYUYGYHIS-UHFFFAOYSA-N 0.000 claims description 2
- 229960002097 dibutylsuccinate Drugs 0.000 claims description 2
- MOJJCFBDUWMVJK-UHFFFAOYSA-N dipentyl propanedioate Chemical compound CCCCCOC(=O)CC(=O)OCCCCC MOJJCFBDUWMVJK-UHFFFAOYSA-N 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 2
- ICBXOVYWGIDVQO-UHFFFAOYSA-N oct-1-en-4-yne Chemical compound CCCC#CCC=C ICBXOVYWGIDVQO-UHFFFAOYSA-N 0.000 claims description 2
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 27
- 230000001603 reducing effect Effects 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- 229920001451 polypropylene glycol Polymers 0.000 description 19
- 210000005239 tubule Anatomy 0.000 description 16
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 10
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- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 7
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- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 3
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- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 2
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- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
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- 125000001033 ether group Chemical group 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
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- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P90/00—Enabling technologies with a potential contribution to greenhouse gas [GHG] emissions mitigation
- Y02P90/70—Combining sequestration of CO2 and exploitation of hydrocarbons by injecting CO2 or carbonated water in oil wells
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a CO 2 Crude oil amphiphilic chemical agent, miscible pressure regulator composition, process for preparing the same and increasing CO 2 And (5) a method for driving recovery ratio. The CO 2 -the crude oil amphiphilic chemical agent has the structure of formula (I):the miscible pressure regulator composition comprises CO 2 Crude oil amphiphilic chemicals and co-solvents. The chemical agent has CO 2 And the amphiphilicity of crude oil can effectively reduce CO 2 And interfacial tension of crude oil. The chemical agent composition can be injected into oil reservoir in the form of pre-slug or concomitant injection to reduce CO 2 Interfacial tension with crude oil, thereby reducing minimum miscible pressure and improving CO 2 And (5) driving recovery ratio.
Description
Technical Field
The invention relates to the field of oilfield exploitation, in particular to a CO 2 Crude oil amphiphilic chemical agent and method for its preparation, minimum miscible pressure regulator composition and method for its preparation, and method for increasing CO 2 And (5) a method for driving recovery ratio.
Background
In recent years, emission reduction of greenhouse gases is increasingly high. Emission reduction measures proposed by the international energy agency include electrified reformation, utilization of hydrogen energy, bioenergy and CCUS (carbon capture, utilization and sequestration) technology, wherein the CCUS contribution accounts for 20%. The global large CCUS project has grown substantially over the last three years. By 2020, 65 projects are all over the world, and CO is trapped and buried in the year 2 About 4000 ten thousand tons of which 77.8% is used for CO 2 And (3) driving an enhanced oil recovery project. According to the prediction of the international energy resource agency, 2040 year global CO 2 The oil displacement yield reaches 150 ten thousand barrels per day, and CO 2 Drives are the primary enhanced recovery technology.
CO 2 The driving can be classified into a mixed-phase driving and an unmixed-phase driving by mechanism. Miscible flooding refers to CO under reservoir conditions 2 Diffusion and mass transfer effects are generated between the oil and the crude oil of the stratum, the oil and the crude oil are mutually dissolved, the interface is eliminated to achieve mixed phase, the interfacial tension is zero, and the theoretical displacement efficiency can reach 100%. Immiscible flooding refers to CO 2 And crude oil can not be completely mixed under the oil reservoir condition, interfaces exist, and the displacement efficiency is low. At reservoir temperature, CO 2 The minimum pressure of the mixed phase with the crude oil in multistage contact is CO 2 Driving a minimum miscible pressure. When the displacement pressure is higher than the minimum miscible pressure, miscible displacement can be realized; when the displacement pressure is lower than the minimum miscible pressure, only immiscible displacement can be performed.
The middle eastern oil reservoir in China has high stratum temperature, high content of heavy components in crude oil and CO 2 The minimum miscible pressure is generally high. CO of some blocks 2 The miscible pressure is even higher than the fracture pressure of the stratum, so that the miscible driving can not be realized, and the immiscible driving can only be carried out. The injection of chemical agents into the oil reservoir to reduce the minimum miscible pressure is an effective way for realizing miscible displacement of oil in a non-miscible displacement oil reservoir.
The Mobil Petroleum company (US patent 4678036;US 4899817;US 4736793) successively discloses the reduction of CO with chemicals such as liquefied petroleum gas, low molecular weight aliphatic hydrocarbons, lower alcohols, tall oil, and the like 2 Minimum miscible pressure with crude oil. Although these chemicals promote crude oil and CO 2 The method achieves the effect of reducing the pressure of the mixed phase, but the method requires a large amount of use to achieve the ideal effect of reducing the pressure of the mixed phase, and has low economic benefit.
The surfactant has an oil-water amphiphilic structure, so that the interfacial tension of oil/water can be greatly reduced, and the mutual solubility of the surfactant and the oil/water can be promoted. The surfactant can reduce interfacial tension of crude oil and water, reduce capillary force, crude oil cohesion and adhesion of crude oil on rock surface, greatly improve oil washing efficiency, and play a role in tertiary oil recovery chemical flooding. Inspired by the surfactant, the invention provides for the use of CO 2 Crude oil amphiphilic chemical agent to reduce CO 2 A new idea of driving minimum miscible pressure. CO 2 The amphiphilic chemical agent of crude oil can be distributed in CO like a surfactant 2 On the interface with crude oil, the interfacial tension of the two is reduced, and CO is promoted 2 Mixing with crude oil to reduce the minimum mixing pressure.
Disclosure of Invention
One of the technical problems to be solved by the invention is that the prior CO 2 CO in oil displacement technology 2 The problems of high minimum miscible pressure with crude oil and low oil displacement efficiency and the problems of low efficiency and large dosage of the existing minimum miscible pressure regulator are solved, and the oil displacement agent containing CO is provided 2 -a minimum miscible pressure regulator composition of a crude oil amphiphilic chemical agent. The chemical agent composition contains CO 2 The amphiphilic chemical agent of crude oil can efficiently reduce CO 2 The interfacial tension of the crude oil, in turn reducing its minimum miscible pressure. The chemical agent composition also comprises small molecule cosolvent such as esters, aromatic hydrocarbon and aliphatic hydrocarbon, which can improve CO on one hand 2 Crude oil amphiphilic chemical agent in supercritical CO 2 Solubility in water, on the other hand, can increase CO 2 The ability to extract light components can make the amphiphilic chemical agent exert the effect of reducing minimum miscible pressure and raise CO 2 Drive and gatherThe rate.
The second technical problem to be solved by the invention is to provide a method for improving CO corresponding to the first technical problem 2 And (5) a method for driving recovery ratio.
One of the objects of the present invention is to provide a CO 2 -a crude oil amphiphilic chemical agent having the structure of formula (I):
wherein R is 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 4; a, a 1 、a 2 Is substituted by R 1 The number of polyether groups b 1 、b 2 Is substituted by R 2 The number of polyether groups c 1 、c 2 Is substituted by R 3 The number of polyether groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 50, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >0；M 1 、M 2 Independently selected from hydrogen atoms, C 3 ～C 50 Straight or branched hydrocarbon radicals or of the formula- (C=O) -R 4 R is a group of (2) 4 Selected from C 6 ～C 50 Straight or branched hydrocarbon group, and M 1 、M 2 、R 1 、R 2 、R 3 Not both hydrogen atoms. a, a 1 、a 2 May be the same or different, b 1 、b 2 C, which may be identical or different 1 、c 2 May be the same or different.
In one embodiment of the present invention, R is preferably 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Not both hydrogen atoms; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer of 0 to 30, anda 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 all are hydrogen atoms;
in the above technical scheme, more preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Comprising at least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Are all hydrogen atoms.
In the second aspect of the present invention, preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Independently selected from hydrogen atoms or C 3 ～C 30 And not both hydrogen atoms.
In the above technical scheme, more preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Comprising at least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Independently selected from hydrogen atoms or from C 5 ～C 30 And not both hydrogen atoms.
In a third aspect of the present invention, preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Independently selected from hydrogen atoms or of the formula- (C=O) -R 4 And are not simultaneously hydrogen atoms, R 4 Selected from C 6 ～C 30 Straight or branched hydrocarbon radicals.
In the above technical scheme, more preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Comprising at least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Selected from hydrogen atoms or of the general formula- (C=O) -R 4 And are not simultaneously hydrogen atoms, R 4 Selected from C 6 ～C 30 Straight or branched hydrocarbon radicals.
In a fourth aspect of the present invention, preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 4, and R 1 、R 2 、R 3 At least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Is a hydrogen atom, or C 5 ～C 30 Straight or branched hydrocarbon radicals.
In a fifth aspect of the present invention, preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 4, and R 1 、R 2 、R 3 At least two kinds ofDifferent groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 、M 2 Is a hydrogen atom, or of the general formula- (C=O) -R 4 R is a group of (2) 4 Selected from C 6 ～C 30 Straight or branched hydrocarbon radicals.
It is a second object of the present invention to provide the CO 2 -a process for the preparation of a crude oil amphiphilic chemical agent comprising the steps of:
(1) reacting imidazoline with epoxy compound in the presence of catalyst A to obtain imidazoline polyether compound (M shown in formula (I) 1 、M 2 CO each being a hydrogen atom 2 -crude oil amphiphilic chemicals;
optionally, (2) reacting the imidazoline polyether compound obtained in step (1) with a base C in a solvent B to obtain an intermediate, and then with a halogenated hydrocarbon R 5 X undergoes nucleophilic substitution reaction to obtain M shown in formula (I) 1 、M 2 At least one is C 3 ～C 50 CO of straight-chain or branched hydrocarbon radicals 2 -crude oil amphiphilic chemicals; or,
optionally, (2)' reacting the polyether compound obtained in step (1) with a carboxylic acid R in the presence of a catalyst D 4 Esterification of COOH to give M of formula (I) 1 、M 2 At least one is- (c=o) -R 4 CO of (c) 2 Crude oil amphiphilic chemicals.
In the technical scheme, the reaction temperature in the step (1) is preferably 100-140 ℃, the catalyst A is preferably at least one of sodium carbonate, potassium carbonate, sodium hydroxide and potassium hydroxide, and the dosage of the catalyst A is preferably 1-5% of the mass of the imidazoline; the epoxy compound is preferably ethylene oxide, propylene oxide, butylene oxide, or the like.
In the above technical scheme, the reaction temperature in the step (2) is preferably 25-130 ℃, the solvent B is preferably benzene and/or toluene, the alkali C is preferably sodium hydroxide and/or potassium hydroxide, the halogenated hydrocarbon is preferably chlorinated hydrocarbon or brominated hydrocarbon, and R 5 Is C 3 ～C 50 Straight chain or of (2)Branched hydrocarbon groups.
In the technical scheme, the reaction temperature of the step (2)' is preferably 180-220 ℃, the catalyst D is preferably sodium bicarbonate and/or potassium bicarbonate, and the dosage of the catalyst D is preferably 0.5-3% of the mass of the polyether compound.
It is a further object of the present invention to provide a process for producing a CO-containing composition 2 -a miscible modifier composition of a crude oil amphiphilic chemical agent comprising said CO 2 Crude oil amphiphilic chemicals and co-solvents.
Wherein the CO 2 -the crude oil amphiphilic chemical agent is selected from at least one of the structures represented by formula (I):
in the formula (I), R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 4; a, a 1 、a 2 Is substituted by R 1 The number of polyether groups b 1 、b 2 Is substituted by R 2 The number of polyether groups c 1 、c 2 Is substituted by R 3 The number of polyether groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 50, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >0；M 1 ，M 2 Independently selected from hydrogen atoms, C 3 ～C 50 Straight or branched hydrocarbon radicals or of the formula- (C=O) -R 4 R is a group of (2) 4 Selected from C 6 ～C 50 Straight or branched hydrocarbon radicals; and M is 1 、M 2 、R 1 、R 2 、R 3 Not both hydrogen atoms.
Preferably, M 1 、M 2 When the two are hydrogen atoms, R 1 、R 2 、R 3 And cannot be hydrogen atoms at the same time.
The cosolvent is ester, aromatic hydrocarbon and aliphatic hydrocarbon, and the cosolvent comprises, but is not limited to, one or more chemical agents such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, amyl acetate, methyl propionate, ethyl propionate, propyl propionate, butyl propionate, pentyl propionate, dimethyl malonate, diethyl malonate, dibutyl malonate, dipentyl malonate, dimethyl succinate, diethyl succinate, dipropyl succinate, dibutyl succinate, dipentyl succinate, benzene, toluene, ethylbenzene, propyl benzene, xylene, trimethylbenzene, hexane, heptane, octane, nonane and the like and isomers thereof.
In the technical scheme, the cosolvent is preferably one or more of methyl acetate, isopropyl acetate, sec-butyl acetate, methyl propionate, propyl propionate, dimethyl malonate, dimethyl succinate, toluene, paraxylene, octane and nonane.
In one embodiment of the present invention, R is preferably 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Not both hydrogen atoms; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 All are hydrogen atoms;
in the above technical scheme, more preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Comprising at least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Are all hydrogen atoms.
In the second aspect of the present invention, preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Independently selected from hydrogen atoms or from C 3 ～C 30 And not both hydrogen atoms.
In the above technical scheme, more preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Comprising at least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Independently selected from hydrogen atoms or from C 5 ～C 30 And not both hydrogen atoms.
In a third aspect of the present invention, preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Independently selected from hydrogen atoms or of the formula- (C=O) -R 4 And are not simultaneously hydrogen atoms, R 4 Selected from C 6 ～C 30 Straight or branched hydrocarbon radicals.
In the above technical scheme, more preferably, R 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Comprising at least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Selected from hydrogen atoms or of the general formula- (C=O) -R 4 And are not simultaneously hydrogen atoms, R 4 Selected from C 6 ～C 30 Straight or branched hydrocarbon radicals.
In the above technical solution, the CO 2 The mass ratio of the crude oil amphiphilic chemical agent to the cosolvent is 1: (1 to 200), preferably 1: (10-100).
A fourth object of the present invention is to provide a process for preparing the miscible pressure regulator composition, which comprises reacting a mixture comprising the CO 2 Mixing and stirring the components including the crude oil amphiphilic chemical agent and the auxiliary agent to obtain the catalyst containing CO 2 -a composition of crude oil amphiphilic chemicals.
In the technical proposal, CO 2 The mass ratio of the crude oil amphiphilic chemical agent to the cosolvent is 1 (1-200), preferably 1: (10-100), for example, 1:10, 1:20, 1:30, 1:40, 1:50, 1:60, 1:70, 1:80, 1:90, 1:100, 1:120, 1:150, 1:200, etc. are possible.
In the technical scheme, the cosolvent can be commercial reagents.
The fifth object of the present invention is to provide a method for improving CO 2 Method for driving recovery ratio, and method for using CO 2 -the minimum miscible pressure regulator composition of the crude oil amphiphilic chemical is injected into the formation in the form of a pre-slug or a satellite for displacement of the crude oil of the formation.
In the above technical solution, the composition is preferably injected into the formation with CO 2 The total mass is 0.1 to 10%, more preferably 0.5 to 5%.
In the technical proposal, the operation steps of the pre-slug injection are that the chemical agent composition and a part of CO are firstly carried out 2 Pre-mixed injection into the formation (the CO 2 Crude oil amphiphilic chemicals approximately accounting for part of CO pre-injected 2 10-30% of the mass of the catalyst, and then injecting pure CO 2 And (3) displacement.
In the technical proposal, the operation steps of the accompanying injection form are as follows 2 The chemical agent composition and the chemical agent are continuously injected into the injection pipeline by adding branchesComposition and CO 2 Co-injection into the formation is mixed in-line.
The invention contains CO 2 The composition of crude oil amphiphilic chemicals comprises an imidazoline polyether (ester) amphiphilic chemical and a small molecule co-solvent. The imidazoline polyether (ester) parent nucleus contains two 'N' hetero atoms, the N atoms have a pair of lone pair electrons, and the N atoms have Lewis basicity and CO 2 Acid-base interaction is carried out between the two; the branched chain of the catalyst comprises polyether groups, ester groups and other CO 2 -a crude oil amphiphilic group and a hydrocarbon group compatible with crude oil such that it has CO 2 Amphiphilic with crude oil, can efficiently reduce CO 2 Interfacial tension with crude oil, thereby reducing its minimum miscible pressure. On the one hand, the micromolecular cosolvent can improve the supercritical CO of the imidazoline polyether/ester amphiphilic chemical agent 2 Medium solubility; on the other hand, due to similar compatibility, the small molecule cosolvent can improve CO 2 The extraction capacity of light and intermediate components in crude oil can make the amphiphilic chemical agent exert its efficiency for reducing minimum miscible pressure.
The invention improves CO 2 CO-containing in the method of flooding recovery 2 -the minimum miscible pressure regulator composition of the crude oil amphiphilic chemical agent has a low melting point, is a low viscosity liquid at-10 ℃ to 100 ℃, is free-flowing, and can be injected into the formation in the form of a pre-slug; in addition, the regulator composition is used in CO 2 Has good solubility, and can be used together with CO in the form of concomitance 2 And (3) co-injecting the crude oil into the stratum to displace the crude oil in the stratum. The proper injection mode can be flexibly selected according to the field condition of the oil field.
With the minimum miscible pressure regulator composition of the invention, CO is improved 2 The method for driving recovery ratio can be used for but not limited to CO with formation temperature of 20-180 ℃ and injection temperature of-10-100 DEG C 2 And (3) oil reservoir flooding. At injection pressure of CO 2 0.5 to 2 percent of chemical agent is added to develop CO 2 And (3) thin tube driving experiment. The experiment of the tubule shows that after the chemical agent composition is added, CO 2 The minimum miscible pressure of the oil is reduced by 36.7 percent at most, and the oil displacement efficiency is higher than that of pure CO 2 The driving is improved by 20.15 percent.
Drawings
FIG. 1 is an infrared spectrum of imidazoline polyoxypropylene ether laurate prepared in example 2.
CO prepared by the invention 2 Crude oil amphiphilic chemicals can be characterized by the following method: using Nicolet-5700 spectrometer and total reflection infrared spectroscopy (ATR) to perform infrared spectroscopy (scanning range 4000-650 cm) -1 ) The chemical structure of the sample to be tested is determined to achieve infrared characterization of the compounds of the invention.
As can be seen from FIG. 1, the wave number is 3501.9cm -1 Characteristic absorption peak at terminal O-H at wavenumber of 2922.6cm -1 、2866.5cm -1 Is characterized by C-H absorption peaks of methylene, methyl and methine on the intermediate heterocycle, ether chain and alkyl chain; 1735.2cm -1 Is a characteristic absorption peak of the ester carbonyl group (c=o); 1108.5cm -1 Is the characteristic absorption peak of ether bond (C-O-C).
Fig. 2 is a diagram of a tubule experimental setup.
Reference numerals illustrate: 1 is a high-pressure plunger pump, 2 is a back pressure valve, 3 is a receiving bottle, 4 is a buffer bottle, 5 is an HPLC pump, 6 is a high-pressure pump, 7 is a data acquisition system, 8 is an oven, and 9 is a tubule model.
Wherein the high-pressure plunger pump 1 is CO 2 The injection system, the HPLC pump 5 is a chemical agent injection system, the high-pressure pump 6 is an oiling system, and the oven 8 is a temperature control system.
Detailed Description
The present invention is described in detail below with reference to specific embodiments, and it should be noted that the following embodiments are only for further description of the present invention and should not be construed as limiting the scope of the present invention, and some insubstantial modifications and adjustments of the present invention by those skilled in the art from the present disclosure are still within the scope of the present invention.
The raw materials used in the examples and comparative examples of the present invention are all disclosed in the prior art, if not particularly limited, and may be obtained, for example, directly or prepared according to the preparation method disclosed in the prior art.
[ example 1 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
72g (1 mol) of imidazoline and 1.8g of sodium hydroxide are weighed into a reaction kettle, and N is replaced 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 348g (6 mol) of propylene oxide is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction, the temperature is reduced to 90 ℃, low-boiling-point substances are removed under reduced pressure, and the mixture is neutralized and dehydrated after being cooled, thus obtaining 406.6g of imidazoline polyoxypropylene (n=6) ether with the yield of 96.8 percent.
(b) Preparation of the composition:
at normal temperature, the imidazoline polyoxypropylene (n=6) ether prepared in the step (a) and ethyl acetate are mixed according to the mass ratio of 1:50, and stirring for 1 hour to obtain a mixture containing CO 2 Minimum miscible pressure regulator S01 of crude oil amphiphilic chemical agent.
[ example 2 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
(1) 72g (1 mol) of imidazoline and 1.8g of sodium hydroxide are weighed into a reaction kettle, and N is replaced 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 348g (6 mol) of propylene oxide is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction, the temperature is reduced to 90 ℃, low-boiling-point substances are removed under reduced pressure, and the mixture is neutralized and dehydrated after being cooled, thus obtaining 406.6g of imidazoline polyoxypropylene (n=6) ether with the yield of 96.8 percent.
(2) To the dried reaction vessel was added 210g (0.5 mol) of imidazoline polyoxypropylene (n=6) ether, 100g (0.5 mol) of lauric acid, 2g of sodium bicarbonate, and oxygen was removed in vacuo. At N 2 Under the protection, the system is heated to 210 ℃ and reacted for 4 hours. After cooling, the mixture was neutralized and dehydrated to obtain 289.7g of imidazoline polyoxypropylene (n=6) ether laurate, and the yield was 96.3%.
(b) Preparation of the composition:
at normal temperature, the imidazoline polyoxypropylene (n=6) ether laurate prepared in the step (a) and methyl propionate are mixed according to the mass ratio of 1:70, and stirring for 1 hour to obtain the CO-containing product 2 Minimum miscible pressure regulator S02 of crude oil amphiphilic chemical agent.
[ example 3 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
(1) 72g (1 mol) of imidazoline and 1.8g of sodium hydroxide are weighed into a reaction kettle, and N is replaced 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 348g (6 mol) of propylene oxide is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction, the temperature is reduced to 90 ℃, low-boiling-point substances are removed under reduced pressure, and the mixture is neutralized and dehydrated after being cooled, thus obtaining 406.6g of imidazoline polyoxypropylene (n=6) ether with the yield of 96.8 percent.
(2) To the dried reaction vessel was added 210g (0.5 mol) of imidazoline polyoxypropylene (n=6) ether, 2g of sodium hydroxide, 300mL of benzene. After heating to 100℃and refluxing for 30 minutes, 74.4g (0.5 mol) of 1-chlorooctane was slowly added dropwise to the reaction vessel, and the reaction was continued for 4 hours. After the reaction, cooling, neutralizing, separating the liquid, and concentrating the organic phase to obtain 241.1g of imidazoline polyoxypropylene (n=6) octyl ether with the yield of 90.5%.
(b) Preparation of the composition:
at normal temperature, the imidazoline polyoxypropylene (n=6) octyl ether prepared in the step (a) and toluene are mixed according to the mass ratio of 1:100, and stirring for 1 hour to obtain a mixture containing CO 2 Minimum miscible pressure regulator S03 of crude oil amphiphilic chemical agent.
[ example 4 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
(1) weighing 72g (1 mol) of imidazoline and 3.0g of sodium hydroxide in a reaction kettle, and replacing N 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 232g (4 mol) of propylene oxide is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction of the epoxypropane is finished, 176g (4 mol) of epoxyethane is slowly introduced, and the pressure is controlled to be less than or equal to 0.10MPa. After the reaction is finished, the temperature is reduced to 90 ℃, low-boiling-point substances are removed under reduced pressure, the mixture is neutralized and dehydrated after being cooled, and 458.4g of imidazoline polyoxypropylene (n=4) polyoxyethylene (n=4) ether is obtained, and the yield is 95.5%.
(b) Preparation of the composition:
at normal temperature, the imidazoline polymer prepared in the step (a) is polymerizedOxypropylene (n=4) polyoxyethylene (n=4) ether and propyl acetate in a mass ratio of 1:60, and stirring for 1 hour to obtain the CO-containing product 2 Minimum miscible pressure regulator S04 of crude oil amphiphilic chemical agent.
[ example 5 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
(1) weighing 72g (1 mol) of imidazoline and 3.0g of sodium hydroxide in a reaction kettle, and replacing N 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 232g (4 mol) of propylene oxide is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction of the epoxypropane is finished, 176g (4 mol) of epoxyethane is slowly introduced, and the pressure is controlled to be less than or equal to 0.10MPa. After the reaction is finished, the temperature is reduced to 90 ℃, low-boiling-point substances are removed under reduced pressure, the mixture is neutralized and dehydrated after being cooled, and 458.4g of imidazoline polyoxypropylene (n=4) polyoxyethylene (n=4) ether is obtained, and the yield is 95.5%.
(2) 240g (0.5 mol) of imidazoline polyoxypropylene (n=4) polyoxyethylene (n=4) ether, 128g (0.5 mol) of palmitic acid, 3g of potassium bicarbonate, and oxygen was removed in vacuo. At N 2 Under the protection, the system is heated to 220 ℃ and reacts for 4 hours. After cooling, the mixture was neutralized and dehydrated to obtain 348.1g of imidazoline polyoxypropylene (n=4) polyoxyethylene (n=4) ether palmitate with a yield of 97.0%.
(b) Preparation of the composition:
at normal temperature, the imidazoline polyoxypropylene (n=4) polyoxyethylene (n=4) ether palmitate prepared in the step (a) and the isoamyl acetate are mixed according to the mass ratio of 1:100, and stirring for 1 hour to obtain a mixture containing CO 2 -a minimum miscible pressure regulator S05 of the crude oil amphiphilic chemical agent.
[ example 6 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
(1) weighing 72g (1 mol) of imidazoline and 3.2g of potassium hydroxide in a reaction kettle, and replacing N 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 432g (6 mol) of epoxybutane is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction is finished, the temperature is reduced to 90 ℃, the low-boiling-point substances are removed by decompression,after cooling, the mixture was neutralized and dehydrated to obtain 476.8g of imidazoline polyoxybutylene (n=6) ether, with a yield of 94.6%.
(b) Preparation of the composition:
at normal temperature, the imidazoline polyoxybutylene (n=6) ether prepared in the step (a) and octane are mixed according to the mass ratio of 1:20, and stirring for 1 hour to obtain a mixture containing CO 2 Minimum miscible pressure regulator S06 of crude oil amphiphilic chemical agent.
[ example 7 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
(1) weighing 72g (1 mol) of imidazoline and 2.8g of sodium hydroxide in a reaction kettle, and replacing N 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 216g (3 mol) of epoxybutane is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction of the epoxybutane is finished, 132g (3 mol) of epoxyethane is slowly introduced, and the pressure is controlled to be less than or equal to 0.10MPa. After the reaction is finished, the temperature is reduced to 90 ℃, low-boiling-point substances are removed under reduced pressure, and the imidazoline polyoxybutylene (n=3) polyoxyethylene (n=3) ether 398.2g is obtained after neutralization and dehydration after cooling, and the yield is 94.8%.
(b) Preparation of the composition:
at normal temperature, the imidazoline polyoxybutylene (n=3) polyoxyethylene (n=3) ether prepared in the step (a) and dimethyl succinate are mixed according to the mass ratio of 1:50, and stirring for 1 hour to obtain a mixture containing CO 2 Minimum miscible pressure regulator of crude oil amphiphilic chemical S07.
[ example 8 ]
(a)CO 2 -crude oil amphiphilic chemical preparation:
(1) 72g (1 mol) of imidazoline and 3.2g of sodium hydroxide are weighed into a reaction kettle, and N is replaced 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 216g (3 mol) of epoxybutane is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction of the epoxybutane is finished, 174g (3 mol) epoxypropane is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction of the epoxypropane is finished, 132g (3 mol) of epoxyethane is slowly introduced, and the pressure is controlled to be less than or equal to 0.10MPa. After the reaction is finished, the temperature is reduced to 90 ℃ and the low-boiling-point substances are removed by decompressionAfter cooling, neutralizing and dehydrating, 550.4g of imidazoline polyoxybutylene (n=3) polyoxypropylene (n=3) ether polyoxyethylene (n=3) ether is obtained, and the yield is 92.6%.
(b) Preparation of the composition:
at normal temperature, the imidazoline polyoxybutylene (n=3) polyoxypropylene (n=3) ether polyoxyethylene (n=3) ether prepared in the step (a) and methyl propionate are mixed according to the mass ratio of 1:80, and stirring for 1 hour to obtain a mixture containing CO 2 Minimum miscible pressure regulator S08 of crude oil amphiphilic chemical.
[ example 9 ]
a)CO 2 -crude oil amphiphilic chemical preparation:
(1) weighing 72g (1 mol) of imidazoline and 2.8g of sodium hydroxide in a reaction kettle, and replacing N 2 And (3) removing oxygen in the reaction kettle for three times. At N 2 Under the protection, the reaction kettle is heated to 120 ℃, 216g (3 mol) of epoxybutane is slowly introduced, and the pressure is controlled to be less than or equal to 0.20MPa. After the reaction of the epoxybutane is finished, 132g (3 mol) of epoxyethane is slowly introduced, and the pressure is controlled to be less than or equal to 0.10MPa. After the reaction is finished, the temperature is reduced to 90 ℃, low-boiling-point substances are removed under reduced pressure, and the imidazoline polyoxybutylene (n=3) polyoxyethylene (n=3) ether 398.2g is obtained after neutralization and dehydration after cooling, and the yield is 94.8%.
(2) 210g (0.5 mol) of imidazoline polyoxybutylene (n=3) polyoxyethylene (n=3) ether, 2g of sodium hydroxide, 300mL of benzene were added to the dried reaction vessel. After heating at 100℃and refluxing for 30 minutes, 102.4g (0.5 mol) of 1-chlorododecane was slowly added dropwise to the reaction vessel, and the reaction was continued for 4 hours. After the reaction, the mixture was cooled, neutralized, separated, and the organic phase was concentrated to obtain 271.7g of polyoxyethylene (n=3) dodecyl ether (n=3) as imidazoline polyoxybutylene (n=3), with a yield of 92.3%.
(b) Preparation of the composition:
at normal temperature, polyoxybutylene (n=3) polyoxyethylene (n=3) dodecyl ether prepared in the step (a) and sec-butyl acetate are mixed according to a mass ratio of 1:120, and stirring for 1 hour to obtain a mixture containing CO 2 -minimum miscible pressure regulator of crude oil amphiphilic chemical S09.
[ comparative example 1 ]
The chemical agent was imidazoline polyoxypropylene (n=6) octyl ether S10 prepared in step (a) of example 3.
[ comparative example 2 ]
The cosolvent of example 3 was used as the chemical agent: toluene S11.
[ comparative example 3 ]
The imidazoline compound S12 in example 6 of Chinese patent CN112302588A was used as the chemical agent.
[ comparative example 4 ]
The chemical agent used in US 4678036 is: hexane S13.
[ example 10 ] minimum miscible pressure measurement
The invention adopts a tubule experimental method to research the chemical agent system on CO 2 Driving the reduction effect of the minimum miscible pressure. Referring to the standard "SY/T6573-2003", a tubule experiment was performed using the tubule device of FIG. 2. The parameters of the tubule are shown in the table I. The experimental procedure was as follows: 1. after the tubules were cleaned, they were saturated with crude oil at the temperature and pressure required for the experiment. 2. CO injection at experimental temperature, pressure and constant injection rate 2 And (3) displacing crude oil, measuring the volume of produced oil once when the pore volume of 0.1 is injected, and recording the upstream and downstream pressure of the tubule and the reading of the pump. 3. When CO 2 Displacement is stopped after accumulation of more than 1.5 pore volumes into the pump. 4. Calculation of the injected 1.2 times pore volume CO 2 The average value of the pressure on the tubule and the pressure on the downstream is recorded as the displacement pressure. 4. Selecting 4-6 pressure points, and repeating the steps 1-3 to perform tubule displacement experiments. Firstly, selecting an experiment under the original stratum pressure, and determining other displacement pressures by adopting a successive approximation minimum pressure method according to the miscibility and the degree thereof. Then, 2-3 pressure points are respectively taken in the mixed phase section and the non-mixed phase section for displacement experiments. 5. And drawing a relation curve of displacement pressure and displacement efficiency. The intersection point of the non-miscible phase section and the miscible phase section is the minimum miscible phase pressure (MMP).
Table one basic parameters of tubules
Crude oil used in the tubule experiment is provided for victory oil fields, and the experiment temperature is 80 ℃.
First, pure CO was measured by means of a tubule experiment 2 Minimum miscible pressure of the drive. Then injecting chemical agent composition with a certain mass into the supercritical CO by using an HPLC pump 2 Mixing, CO-injecting into tubule, and measuring "CO" by the same method 2 The minimum miscible pressure of the +chemical "drive. The test results are shown in Table II.
Surface two chemical agent composition pair CO 2 Reducing effect of minimum miscible pressure of driving
Example 10 oil displacement efficiency measurement
With reference to the standard SY/T6573-2003, an indoor oil displacement experiment was performed using the tubule described above. Pure CO is developed under the pressure of 26.0MPa at 80 DEG C 2 Flooding and CO 2 +chemical "drive experiments, record 1.2PVCO injected 2 And the oil displacement efficiency is improved. The experimental results are shown in Table III.
Table three indoor oil displacement test results
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Claims (17)
1. CO (carbon monoxide) 2 -a crude oil amphiphilic chemical agent having the structure of formula (I):
wherein R is 1 、R 2 、R 3 Independently selected from (CH) 2 ) e H, e is any integer from 0 to 4; a, a 1 、a 2 Is substituted by R 1 The number of polyether groups b 1 、b 2 Is substituted by R 2 The number of polyether groups c 1 、c 2 Is substituted by R 3 The number of polyether groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 50, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >0；M 1 、M 2 Independently selected from hydrogen atoms, C 3 ～C 50 Straight or branched hydrocarbon radicals of the formula- (C=O) -R 4 R is a group of (2) 4 Selected from C 6 ～C 50 Straight or branched hydrocarbon group, and M 1 、M 2 、R 1 、R 2 、R 3 Not both hydrogen atoms.
2. The CO of claim 1 2 -a crude oil amphiphilic chemical agent characterized in that:
R 1 、R 2 、R 3 independently selected from (CH) 2 ) e H, e is any integer from 0 to 3, and R 1 、R 2 、R 3 Not both hydrogen atoms; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Are all hydrogen atoms.
3. The CO of claim 1 2 -a crude oil amphiphilic chemical agent characterized in that:
R 1 、R 2 、R 3 independently selected from (CH) 2 ) e H, e is any integer from 0 to 3; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 、M 2 Independently selected from hydrogen atoms, or C 3 ～C 30 And not both hydrogen atoms.
4. The CO of claim 1 2 -a crude oil amphiphilic chemical agent characterized in that:
R 1 、R 2 、R 3 independently selected from (CH) 2 ) e H, e is any integer from 0 to 3; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 、M 2 Independently selected from hydrogen atoms, or of the general formula- (C=O) -R 4 And are not simultaneously hydrogen atoms, R 4 Selected from C 6 ～C 30 Straight or branched hydrocarbon radicals.
5. The CO of claim 1 2 -a crude oil amphiphilic chemical agent characterized in that:
R 1 、R 2 、R 3 independently selected from (CH) 2 ) e H, e is any integer from 0 to 4, and R 1 、R 2 、R 3 At least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 ，M 2 Is a hydrogen atom, or C 5 ～C 30 Straight or branched hydrocarbon radicals.
6. The CO of claim 1 2 -a crude oil amphiphilic chemical agent characterized in that:
R 1 、R 2 、R 3 independently selected from (CH) 2 ) e H, e is any integer from 0 to 4, and R 1 、R 2 、R 3 At least two different groups; a, a 1 、a 2 、b 1 、b 2 、c 1 、c 2 Independently selected from any integer from 0 to 30, and a 1+ a 2+ b 1+ b 2+ c 1+ c 2 >1；M 1 、M 2 Is a hydrogen atom, or of the general formula- (C=O) -R 4 R is a group of (2) 4 Selected from C 6 ～C 30 Straight or branched hydrocarbon radicals.
7. A CO according to any one of claims 1 to 6 2 -a process for the preparation of a crude oil amphiphilic chemical agent comprising the steps of:
(1) reacting imidazoline with epoxy compound in the presence of catalyst A to obtain imidazoline polyether compound (M shown in formula (I) 1 、M 2 CO each being a hydrogen atom 2 -crude oil amphiphilic chemicals;
optionally, (2) reacting the imidazoline polyether compound obtained in step (1) with a base C in a solvent B to obtain an intermediate, and then with a halogenated hydrocarbon R 5 X undergoes nucleophilic substitution reaction to obtain M shown in formula (I) 1 、M 2 At least one is C 3 ～C 50 CO of straight-chain or branched hydrocarbon radicals 2 -crude oil amphiphilic chemicals; or,
optionally, (2)' reacting the polyether compound obtained in step (1) with a carboxylic acid R in the presence of a catalyst D 4 Esterification of COOH to give M of formula (I) 1 、M 2 At least one is- (c=o) -R 4 CO of (c) 2 Crude oil amphiphilic chemicals.
8. The CO according to claim 7 2 -a process for the preparation of a crude oil amphiphilic chemical agent, characterized in that:
in the step (1), the reaction temperature is 100-140 ℃, the catalyst A is at least one of sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and the dosage of the catalyst A is 1-5% of the mass of the imidazoline; and/or the number of the groups of groups,
in the step (2), the reaction temperature is 25-130 ℃, the solvent B is benzene and/or toluene, the alkali C is sodium hydroxide and/or potassium hydroxide, the halogenated hydrocarbon is chlorinated hydrocarbon and/or brominated hydrocarbon, and R 5 Is C 3 ～C 50 Straight or branched hydrocarbon radicals; and/or the number of the groups of groups,
in the step (2)' the reaction temperature is 180-220 ℃, the catalyst D is sodium bicarbonate and/or potassium bicarbonate, and the dosage of the catalyst D is 0.5-3% of the mass of the polyether compound.
9. A miscible pressure regulator composition comprising the CO of any one of claims 1 to 6 2 -a crude oil amphiphilic chemical agent and a co-solvent, wherein the co-solvent is an ester, an aromatic hydrocarbon and an aliphatic hydrocarbon.
10. The miscible pressure regulator composition of claim 9, wherein:
the cosolvent is selected from at least one of methyl acetate, ethyl acetate, propyl acetate, butyl acetate, amyl acetate, methyl propionate, ethyl propionate, propyl propionate, butyl propionate, pentyl propionate, dimethyl malonate, diethyl malonate, dibutyl malonate, dipentyl malonate, dimethyl succinate, diethyl succinate, dipropyl succinate, dibutyl succinate, dipentyl succinate, benzene, toluene, ethylbenzene, propyl benzene, xylene, trimethylbenzene, hexane, heptane, octane, nonane and isomers thereof.
11. The miscible pressure regulator composition of claim 9, wherein:
the CO 2 The mass ratio of the crude oil amphiphilic chemical agent to the cosolvent is 1: (1-200).
12. The miscible pressure regulator composition of claim 11, wherein:
the CO 2 The mass ratio of the crude oil amphiphilic chemical agent to the cosolvent is 1: (10-100).
13. A process for the preparation of a miscible pressure regulator composition as claimed in any of claims 9 to 12 comprising reacting a mixture comprising said CO 2 -the crude oil amphiphilic chemical agent is mixed with the components including the co-solvent.
14. Improving CO 2 A method of driving recovery comprising combining the method of any one of claims 9 to 12The miscible modifier composition is injected into the formation in the form of a pre-slug or a satellite injection to displace crude oil from the formation.
15. Increasing CO according to claim 14 2 The method for driving recovery ratio is characterized in that:
the composition is used in an amount of CO injected into the stratum 2 0.1 to 10 percent of the total mass.
16. Increasing CO according to claim 15 2 The method for driving recovery ratio is characterized in that:
the composition is used in an amount of CO injected into the stratum 2 0.5 to 5 percent of the total mass.
17. Increasing CO according to claim 14 2 The method for driving recovery ratio is characterized in that:
the pre-slug injection is performed by first combining the composition with a portion of the CO 2 Pre-mix injection into a formation, wherein the CO 2 -the crude oil amphiphilic chemical agent comprises part of the CO 2 10-30% of the mass, and then injecting pure CO 2 Performing displacement;
the operation steps of the injection of the concomitant injection form are as follows 2 Adding a branch to the injection line for continuous injection of the composition, the composition and CO 2 Co-injection into the formation is mixed in-line.
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| CN103320797A (en) * | 2013-05-30 | 2013-09-25 | 天津科维津宏环保科技有限公司 | Water-soluble non-ionic imidazoline corrosion inhibitor and preparation method thereof |
| CN112707865A (en) * | 2019-10-25 | 2021-04-27 | 中国石油化工股份有限公司 | Zwitterionic surfactant and preparation method thereof |
| CN112876128A (en) * | 2021-01-22 | 2021-06-01 | 沈阳工业大学 | Efficient alkoxylated imidazoline derivative rust inhibitor and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103320797A (en) * | 2013-05-30 | 2013-09-25 | 天津科维津宏环保科技有限公司 | Water-soluble non-ionic imidazoline corrosion inhibitor and preparation method thereof |
| CN112707865A (en) * | 2019-10-25 | 2021-04-27 | 中国石油化工股份有限公司 | Zwitterionic surfactant and preparation method thereof |
| CN112876128A (en) * | 2021-01-22 | 2021-06-01 | 沈阳工业大学 | Efficient alkoxylated imidazoline derivative rust inhibitor and preparation method and application thereof |
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| Title |
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| 咪唑啉的合成、性能及其工业用途;萧越;;中国洗涤用品工业(第02期);48-50 * |
| 油溶性非离子咪唑啉的开发与性能评价;张浩;陆原;张勇;张颖;唐晓静;杨记涛;;油田化学(第03期);141-145 * |
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