CN115872907B - Sulfonate thickened oil viscosity reducer and preparation method and application thereof - Google Patents
Sulfonate thickened oil viscosity reducer and preparation method and application thereof Download PDFInfo
- Publication number
- CN115872907B CN115872907B CN202111151123.1A CN202111151123A CN115872907B CN 115872907 B CN115872907 B CN 115872907B CN 202111151123 A CN202111151123 A CN 202111151123A CN 115872907 B CN115872907 B CN 115872907B
- Authority
- CN
- China
- Prior art keywords
- formula
- viscosity reducer
- hydrocarbon group
- oil
- viscosity
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000003638 chemical reducing agent Substances 0.000 title claims abstract description 71
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000011084 recovery Methods 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000000295 fuel oil Substances 0.000 claims abstract description 15
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 7
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims abstract description 7
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000006277 sulfonation reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000006396 nitration reaction Methods 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 230000033558 biomineral tissue development Effects 0.000 claims description 5
- 230000001546 nitrifying effect Effects 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 230000000802 nitrating effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 67
- 230000000694 effects Effects 0.000 abstract description 17
- -1 small molecule alcohols Chemical class 0.000 description 28
- 238000011156 evaluation Methods 0.000 description 24
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000006073 displacement reaction Methods 0.000 description 13
- 230000009467 reduction Effects 0.000 description 11
- 239000010779 crude oil Substances 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000001276 controlling effect Effects 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QMGOXEWNQKNUQO-UHFFFAOYSA-N 1-hexadecyl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2C(CCCCCCCCCCCCCCCC)CCC2=C1 QMGOXEWNQKNUQO-UHFFFAOYSA-N 0.000 description 1
- UHAGUGQCWXOWHP-UHFFFAOYSA-N 1-octyl-2,3-dihydro-1H-indene Chemical compound C(CCCCCCC)C1CCC2=CC=CC=C12 UHAGUGQCWXOWHP-UHFFFAOYSA-N 0.000 description 1
- PEACLFUSUWSZCP-UHFFFAOYSA-N C(CCCCCCCCCCC)C1CCC2=CC=CC=C12 Chemical compound C(CCCCCCCCCCC)C1CCC2=CC=CC=C12 PEACLFUSUWSZCP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008398 formation water Substances 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a sulfonate heavy oil viscosity reducer, which comprises at least one of the compounds shown in the following formula I, wherein R 1 Is C 6 ‑C 30 R is a hydrocarbon group of 2 Is H or C 1 ‑C 30 Is a hydrocarbon group of (2); m is an alkali metal ion or an alkaline earth metal ion, and n is the number of M which makes the compound shown in the formula I electrically neutral. The invention also discloses a preparation method of the viscosity reducer and application of the viscosity reducer in thick oil exploitation. The sulfonate thickened oil viscosity reducer has good affinity with thickened oil, can effectively reduce the viscosity of the thickened oil, has high interfacial activity, can effectively improve the recovery ratio of the thickened oil, and has good application prospect.
Description
Technical Field
The invention belongs to the field of heavy oil reservoir development, and particularly relates to a sulfonate heavy oil viscosity reducer, a preparation method and application thereof.
Background
At present, most tertiary oil recovery surfactants at home and abroad are surfactants (CN 1203935A, CN1566258A and CN 1426833A) modified by petroleum sulfonate, heavy alkylbenzenesulfonate and other oil refining byproducts, and the surfactants are characterized by wide material availability and low cost. However, these surfactants also have a series of problems such as poor salt tolerance, particularly divalent cation tolerance, and the like, and cannot be applied to high-temperature and high-mineralization oilfield blocks. Therefore, the development of the novel surfactant has extremely important significance for the tertiary oil recovery industry in China.
Surfactants have been successfully used in common reservoirs (first and second reservoirs) (CN 1458219 a), but for heavy oil reservoirs, the surfactant effect is limited and insufficient for the first and second reservoirs. For heavy oil reservoirs, conventional methods are difficult to produce, so special technological measures such as thermal oil production, chemical oil production, biological oil production, combination methods and the like are adopted. In recent years, chemical methods have received increasing attention. The main difficulties in heavy oil recovery are that the viscosity of crude oil is high, the fluidity of crude oil is poor, and the viscosity of crude oil is high, which causes poor wave and efficiency in the general displacement process of displacement fluid (such as hot water). The method is to reduce the viscosity of crude oil, reduce the interfacial tension of crude oil and water, change the wettability of stratum, etc.
Therefore, the development of the novel thickened oil viscosity reducer has important significance for the exploitation of a thickened oil reservoir.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a novel viscosity reducer which has good affinity with thick oil, can effectively reduce the viscosity of the thick oil, has high interfacial activity, can effectively improve the recovery ratio of the thick oil, and has good application prospect.
One of the technical problems to be solved by the invention is the problem of poor oil displacement effect of the surfactant in the heavy oil reservoir in the prior production technology, and the novel sulfonate heavy oil viscosity reducer is provided, which can effectively reduce the viscosity of heavy oil and has high interfacial activity, so that the recovery ratio of the heavy oil can be improved. The second technical problem to be solved by the invention is to provide a preparation method of the sulfonate thickened oil viscosity reducer corresponding to the first technical problem. The invention aims to solve the third technical problem of providing the viscosity reducer which is one of the technical problems or the application of the viscosity reducer prepared by the preparation method of the second technical problem in oilfield development, in particular in thickened oil exploitation.
To this end, the first aspect of the present invention provides a sulfonate heavy oil viscosity reducer comprising at least one of the compounds of formula I,
in the formula I, R 1 Is C 6 -C 30 R is a hydrocarbon group of 2 Is H or C 1 -C 30 Is a hydrocarbon group of (2); m is an alkali metal ion or an alkaline earth metal ion, and n is the number of M which makes the compound shown in the formula I electrically neutral.
According to some embodiments of the invention, the alkali metal ion is sodium ion or potassium ion and the alkaline earth metal ion is calcium ion or magnesium ion.
According to the invention, n is the number of M which makes the compound of formula I electrically neutral, for example, n=1 when M is an alkali metal ion and n=0.5 when M is an alkaline earth metal ion.
According to some embodiments of the invention, R 1 Is C 6 -C 30 Is a hydrocarbon group.
According to some embodiments of the invention, R 1 Is C 6 -C 20 Is a hydrocarbon group.
According to some embodiments of the invention, R 1 Is C 8 -C 16 Is a hydrocarbon group.
According to some embodiments of the invention, R 2 Is H or C 1 -C 30 Is a hydrocarbon group.
According to some embodiments of the invention, R 2 Is H or C 1 -C 18 Is a hydrocarbon group.
According to some embodiments of the invention, R 2 Is H or C 1 -C 10 Is a hydrocarbon group.
According to some embodiments of the invention, R 2 Is H or C 1 -C 6 Is a hydrocarbon group.
According to the invention, in formula I, the radicals-R 1 and-R 2 The substitution position on the five-membered ring of indane is not specifically limited and may be, for example, ortho substitution or meta substitution. In some embodiments, the group-R in formula I 1 and-R 2 Meta-substitution on the five-membered ring of indane.
According to the invention, in formula I, the amino acid sequence-NO 2 and-SO 3 (M) n The substitution position on the benzene ring of indane is not specifically limited, and may be, for example, ortho-, meta-, or para-substitution, and is preferably meta-substitution.
According to some embodiments of the invention, the viscosity reducer comprises at least one of the compounds of formula I-1,
in the formula I-1, R 1 ，R 2 M and n have the same definition as in formula I.
According to some embodiments of the invention, the viscosity reducer comprises at least one of the compounds of formula I-2,
in the formula I-2, R 1 ，R 2 M and n have the same definition as in formula I.
According to some embodiments of the invention, the viscosity reducer further comprises water having a total degree of mineralization of 0-80000 mg/L.
According to some embodiments of the invention, the viscosity reducer includes water having a total degree of mineralization of 100-30000 mg/L.
According to some embodiments of the invention, the water is present in an amount of 90wt% to 99.9wt% based on the total mass of the viscosity reducer, and in some embodiments, in an amount of 95wt% to 99.9wt%.
According to the present invention, the water having the total degree of mineralization of 0 to 80000mg/L may be at least one of oilfield injection water, formation water, sea water, rainwater, river water, and the like. The water is more preferably oil field injection water in terms of construction convenience, water resource saving and the like, for example, the oil field injection water is victory oil field injection water adopted in the embodiment of the invention, and the composition of the oil field injection water is shown in table 1.
According to the invention, the viscosity reducer of the invention can also comprise additives commonly used in the field, such as polyacrylamide, small molecule alcohols, DMSO, diethanolamine, CTAC and the like commonly used in the field for increasing the oil displacement effect.
In a second aspect, the present invention provides a method for preparing a viscosity reducer according to the first aspect of the present invention, comprising the steps of:
a) Mixing a compound shown in a formula II with a nitrifying agent to perform a nitrifying reaction to obtain a nitrified product shown in a formula III;
b) Mixing the obtained nitrified product with a sulfonating agent to carry out sulfonation reaction to obtain a sulfonated product shown in a formula IV;
c) Mixing the obtained sulfonated product with alkali to obtain a compound shown in a formula I;
in formula II, III, IV, R 1 And R is 2 Has the same definition as formula I.
According to some embodiments of the present invention, the compound of formula II has a structure as shown in formula II-1 below, the nitration product of formula III has a structure as shown in formula III-1 below, and the sulfonation product of formula IV has a structure as shown in formula IV-1 below:
in the formulas II-1, III-1 and IV-1, R 1 And R is 2 Has the same definition as formula I.
According to some embodiments of the invention, the nitrating agent is nitric acid and/or dinitrogen pentoxide or a mixture of at least one of nitric acid and dinitrogen pentoxide with at least one of concentrated sulfuric acid, glacial acetic acid, acetic anhydride, phosphorus pentoxide.
According to some embodiments of the invention, the sulfonating agent is selected from at least one of concentrated sulfuric acid, fuming sulfuric acid, and sulfur trioxide.
According to some embodiments of the invention, the base is at least one of an alkali metal hydroxide and an alkaline earth metal hydroxide. In some embodiments, the base is sodium hydroxide and/or potassium hydroxide.
According to some embodiments of the invention, in step a), the molar ratio of the compound of formula II to the nitrating agent is (1:1) - (3:1).
According to some embodiments of the invention, in step b), the molar ratio of the nitrated product to the sulphonating agent is (1:1) - (5:1).
According to some embodiments of the invention, in step c), the amount of base added is such that the pH of the mixture of the sulphonated product and base is adjusted to 7-14.
According to some embodiments of the invention, in step a), the temperature of the nitration reaction is from 0 to 80 ℃. In some embodiments, the temperature of the nitration reaction is from 30 to 70 ℃, such as 30 ℃, 40 ℃, 50 ℃, 60 ℃, 70 ℃ and any value therebetween.
According to some embodiments of the invention, in step a), the nitration is carried out for a time of from 1 to 10 hours. In some embodiments, the nitration reaction is for a period of time ranging from 1 to 5 hours, such as 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, and any value therebetween.
According to some embodiments of the invention, in step b), the temperature of the sulfonation reaction is 20-80 ℃. In some embodiments, the temperature of the sulfonation reaction is 30-60 ℃, such as 30 ℃, 35 ℃, 40 ℃, 45 ℃, 50 ℃, 55 ℃, 60 ℃, and any value therebetween.
According to some embodiments of the invention, in step b), the sulfonation reaction is for a time of 0.5 to 10 hours. In some embodiments, the sulfonation reaction is for a time of 0.5 to 5 hours, such as 0.5 hours, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours, and any value therebetween.
In a third aspect the present invention provides the use of a viscosity reducer as described in the first aspect of the invention or a viscosity reducer as produced by a method of manufacture as described in the second aspect of the invention in oilfield recovery, particularly heavy oil recovery, for example to enhance heavy oil recovery.
According to some embodiments of the invention, in the application, the viscosity reducer is used as an oil displacement agent.
According to some embodiments of the invention, the oilfield recovery is tertiary oil recovery.
The invention has the beneficial effects that:
the sulfonate thickened oil viscosity reducer has good surface and interfacial activities and good salt resistance, can form lower interfacial tension on an oil-water interface, can effectively reduce the viscosity of thickened oil, improves the recovery ratio of thickened oil, and has wide application prospect and practical significance.
Detailed Description
In order that the invention may be more readily understood, the invention will be described in detail below with reference to the following examples, which are provided for the purpose of illustration only and are not to be construed as limiting the scope of the invention. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
The related data in the embodiment of the invention are obtained according to the following test method:
and (3) evaluating the viscosity reduction effect of the thickened oil: and measuring the viscosity reduction rate by adopting a Brookfield viscometer DV-III according to the method of the general technical condition of the QSH1020 1519-2013 thick oil viscosity reducer.
Interfacial tension evaluation: the interfacial tension between the viscosity reducer and the thick oil was measured using a TX-500C rotary drop interfacial tensiometer produced by texas university, usa at 80 ℃ at a rotational speed of 4500 rpm.
Evaluating oil displacement experiment: according to the physical simulation oil displacement effect test of the compound oil displacement system in the SY/T6424-2000 compound oil displacement system performance test method, the length is 30cm, the diameter is 2.5cm, and the permeability is 1.5m at 80 DEG C 2 And (3) carrying out a simulated oil displacement experiment on the core. Firstly, water flooding is carried out by using winning injection water of a winning oil field until the water content is 98%, after the water flooding is finished, the prepared viscosity reducer with the volume of 0.3pv (core pore volume) is injected, then the water flooding is carried out until the water content is 98%, and the crude oil recovery ratio is calculated and improved.
Example 1
Synthesis of 1, 1-hexanyl-4-nitroindan-6-sulfonate
a) 1.0mol of 1-hexane-based indane is added into a reactor provided with a condensing device and a stirring device, 2.5mol of fuming nitric acid is dripped, the reaction temperature is controlled to be 50 ℃, and after the dripping is finished, the reaction is continued for 2 hours, so that 0.85mol of 1-hexane-4-nitroindane is obtained;
b) Adding 0.85mol of hexanyl nitroindane synthesized in the step a) into a membrane type sulfonation reaction device, and introducing 1.5mol of SO 3 And controlling the reaction temperature to be 45 ℃ for 30 minutes to obtain 0.81mol of 1-hexyl-4-nitroindan-6-sulfonic acid, and adding sodium hydroxide to adjust the pH to 9 to obtain 1-hexyl-4-nitroindan-6-sodium sulfonate.
2. Evaluation of viscosity reducer Property
A solution of 0.2wt% of the 1-hexyl-4-nitroindan-6-sodium sulfonate is prepared by using winning injection water of a winning oil field to obtain a thick oil viscosity reducer, and the thick oil viscosity reducer is used for thick oil viscosity reduction effect evaluation and interfacial tension evaluation, and the results are shown in the following table 3. The composition of the winning injection water in the victory oilfield is shown in table 1. The composition of the resulting viscosity reducer is shown in Table 2.
Example 2
Synthesis of 1, 1-octyl-4-nitroindan-6-sulfonate
a) 1.0mol of 1-octyl indan and 2.2mol of fuming nitric acid are added into a reactor provided with a condensing device and a stirring device, the reaction temperature is controlled to be 50 ℃, and after the dripping is finished, the reaction is continued for 2 hours, so that 0.82mol of 1-octyl-4-nitroindan is obtained;
b) Adding 0.82mol of 1-octyl-4-nitroindane synthesized in the step a) into a membrane type sulfonation reaction device, and introducing 1.5mol of SO 3 And controlling the reaction temperature to be 45 ℃ for 30 minutes to obtain 0.79mol of 1-octyl-4-nitroindan-6-sulfonic acid, and adding sodium hydroxide to adjust the pH to 9 to obtain 1-octyl-4-nitroindan-6-sodium sulfonate.
2. Evaluation of viscosity reducer Property
A solution of 0.5wt% of the sodium octyl nitroindansulfonate is prepared by using winning injection water of a winning oil field to obtain a thick oil viscosity reducer, and the thick oil viscosity reducer is used for thick oil viscosity reduction effect evaluation and interfacial tension evaluation, and the results are shown in the following table 3. The composition of the winning injection water in the victory oilfield is shown in table 1. The composition of the resulting viscosity reducer is shown in Table 2.
Example 3
Synthesis of 1, 1-dodecyl-4-nitroindan sulfonate
a) 1.0mol of 1-dodecyl indan and 1.5mol of fuming nitric acid are added into a reactor provided with a condensing device and a stirring device, the reaction temperature is controlled to be 50 ℃, and after the dripping is finished, the reaction is continued for 2 hours, so that 0.83mol of 1-dodecyl-4-nitroindan is obtained;
b) Adding 0.83mol of 1-dodecyl-4-nitroindane synthesized in the step a) into a membrane type sulfonation reaction device, and introducing 1.5mol of SO 3 And controlling the reaction temperature to be 45 ℃ for 30 minutes to obtain 0.78mol of 1-dodecyl-4-nitroindan-6-sulfonic acid, and adding sodium hydroxide to adjust the pH value to 9 to obtain 1-dodecyl-4-nitroindan-6-sodium sulfonate.
2. Evaluation of viscosity reducer Property
1.0wt% of the solution of the 1-dodecyl-4-nitroindan-6-sodium sulfonate is prepared by using winning injection water of a winning oil field to obtain a thick oil viscosity reducer which is used for thick oil viscosity reduction effect evaluation, interfacial tension evaluation and oil displacement experiments, wherein the thick oil viscosity reduction effect evaluation and interfacial tension evaluation results are shown in the following table 3. The composition of the winning injection water in the victory oilfield is shown in table 1. The composition of the resulting viscosity reducer is shown in Table 2.
The result shows that the viscosity reducer improves the recovery ratio of crude oil by 7.2 percent.
Example 4
Synthesis of 1, 1-hexadecyl-4-nitroindan sulfonate
a) 1.0mol of 1-hexadecyl indane and 2.1mol of fuming nitric acid are added into a reactor provided with a condensing device and a stirring device, the reaction temperature is controlled to be 50 ℃, and after the dripping is finished, the reaction is continued for 2 hours, so that 0.81mol of 1-hexadecyl-4-nitroindane is obtained;
b) Adding 0.81mol of 1-hexadecyl-4-nitroindane synthesized in the step a) into a membrane type sulfonation reaction device, and introducing 1.5mol of SO 3 And controlling the reaction temperature to be 45 ℃ for 30 minutes, obtaining 0.75mol of 1-hexadecyl-4-nitroindan-6-sulfonic acid, adding sodium hydroxide to adjust the pH value to 9, and obtaining the 1-hexadecyl-4-nitroindan-6-sodium sulfonate.
2. Evaluation of viscosity reducer Property
Preparing a solution of 0.5wt% of the 1-hexadecyl-4-nitroindan-6-sodium sulfonate by using winning injection water of a winning oil field to obtain a thick oil viscosity reducer, wherein the thick oil viscosity reducer is used for thick oil viscosity reduction effect evaluation, interfacial tension evaluation and oil displacement experiments, and the thick oil viscosity reduction effect evaluation and interfacial tension evaluation results are shown in the following table 3. The composition of the winning injection water in the victory oilfield is shown in table 1. The composition of the resulting viscosity reducer is shown in Table 2.
As a result, the viscosity reducer is measured to improve the recovery ratio of crude oil by 10.1 percent.
Example 5
Synthesis of 1, 1-octadecyl-4-nitroindan sulfonate
a) 1.0mol of 1-octadecyl indane is added into a reactor provided with a condensing device and a stirring device, 1.5mol of fuming nitric acid is dripped, the reaction temperature is controlled to be 50 ℃, and after the dripping is finished, the reaction is continued for 2 hours, so that 0.80mol of 1-octadecyl-4-nitroindane is obtained;
b) Adding 0.80mol of 1-octadecyl-4-nitroindane synthesized in the step a) into a membrane type sulfonation reaction device, and introducing 1.5mol of SO 3 And controlling the reaction temperature to be 45 ℃ for 30 minutes to obtain 0.72mol of 1-octadecyl-4-nitroindan-6-sulfonic acid, and adding sodium hydroxide for regulatingThe pH value is regulated to 9, and the sodium 1-octadecyl-4-nitroindane-6-sulfonate is obtained.
2. Evaluation of viscosity reducer Property
A solution of 0.5wt% of the 1-octadecyl-4-nitroindan-6-sodium sulfonate is prepared by using winning injection water of a winning oil field to obtain a thick oil viscosity reducer, and the thick oil viscosity reducer is used for thick oil viscosity reduction effect evaluation and interfacial tension evaluation, and the results are shown in the following table 3. The composition of the winning injection water in the victory oilfield is shown in table 1. The composition of the resulting viscosity reducer is shown in Table 2.
Example 6
Synthesis of 1, 1-dodecyl-3-octyl-4-nitroindan sulfonate
The procedure is as in example 3 except that 1-dodecyl-3-octyl indan is used as the starting material to give sodium 1-dodecyl-3-octyl-4-nitroindansulfonate.
2. Evaluation of viscosity reducer Property
1wt% of 1-dodecyl-3-octyl-4-nitroindan sodium sulfonate solution is prepared by using winning injection water of a winning oil field to obtain a thick oil viscosity reducer, and the thick oil viscosity reducer is used for thick oil viscosity reduction effect evaluation and interfacial tension evaluation, and the results are shown in the following table 3. The composition of the winning injection water in the victory oilfield is shown in table 1. The composition of the viscosity reducer is shown in Table 2.
Comparative example 1
The evaluation method was the same as in example 3 except that sodium petroleum sulfonate (victory refinery) was used instead of sodium 1-dodecyl-4-nitroindan-6-sulfonate in example 3, and the results are shown in Table 3. As a result, the obtained viscosity reducer improves the recovery ratio of crude oil by 1.6%.
TABLE 1 victory oilfield injection water
Table 2 viscosity reducer composition
TABLE 3 oil displacement agent Performance
| Viscosity reduction rate (%) | Interfacial tension (mN/m) | |
| Example 1 | 85 | 0.0091 |
| Example 2 | 91 | 0.0071 |
| Example 3 | 96 | 0.0056 |
| Example 4 | 92 | 0.0064 |
| Example 5 | 98 | 0.0041 |
| Example 6 | 99.2 | 0.0048 |
| Comparative example 1 | 48 | 0.13 |
It should be noted that the above-described embodiments are only for explaining the present invention and do not constitute any limitation of the present invention. The invention has been described with reference to exemplary embodiments, but it is understood that the words which have been used are words of description and illustration, rather than words of limitation. Modifications may be made to the invention as defined in the appended claims, and the invention may be modified without departing from the scope and spirit of the invention. Although the invention is described herein with reference to particular means, materials and embodiments, the invention is not intended to be limited to the particulars disclosed herein, as the invention extends to all other means and applications which perform the same function.
Claims (18)
1. A sulfonate heavy oil viscosity reducer comprises at least one of compounds shown in the following formula I,
in the formula I, R 1 Is C 6 -C 30 R is a hydrocarbon group of 2 Is H or C 1 -C 30 Is a hydrocarbon group of (2); m is an alkali metal ion or an alkaline earth metal ion, and n is the number of M which makes the compound shown in the formula I electrically neutral.
2. A viscosity reducer according to claim 1, wherein the alkali metal ion is sodium ion or potassium ion and the alkaline earth metal ion is calcium ion or magnesium ion.
3. The viscosity reducer according to claim 1, wherein n=1 when M is an alkali metal ion and n=0.5 when M is an alkaline earth metal ion.
4. A viscosity reducer according to any of claims 1 to 3, wherein in formula I, R 1 Is C 6 -C 30 Alkyl of (a);
and/or R 2 Is H, or C 1 -C 30 Is a hydrocarbon group.
5. The viscosity reducer of claim 4, wherein R 1 Is C 6 -C 20 Is a hydrocarbon group.
6. The viscosity reducer of claim 4, wherein R 1 Is C 8 -C 16 Is a hydrocarbon group.
7. The viscosity reducer of claim 4, wherein R 2 Is H or C 1 -C 18 Is a hydrocarbon group.
8. The viscosity reducer of claim 4, wherein R 2 Is H or C 1 -C 6 Is a hydrocarbon group.
9. The viscosity reducer according to any of claims 1 to 3 and 5 to 8, wherein the viscosity reducer comprises at least one of the compounds represented by the following formula I-1,
in the formula I-1, R 1 ，R 2 M and n have the same definition as in formula I.
10. A viscosity reducer according to any of claims 1-3, 5-8, further comprising water with a total degree of mineralization of 0-80000mg/L, wherein the mass content of water is 90-99.9 wt% based on the total mass of the viscosity reducer.
11. The viscosity reducer of claim 10, further comprising water having a total degree of mineralization of 100-30000 mg/L.
12. The method for producing a viscosity reducer according to any one of claims 1 to 11, comprising the steps of:
a) Mixing a compound shown in a formula II with a nitrifying agent to perform a nitrifying reaction to obtain a nitrified product shown in a formula III;
b) Mixing the obtained nitrified product with a sulfonating agent to carry out sulfonation reaction to obtain a sulfonated product shown in a formula IV;
c) Mixing the obtained sulfonated product with alkali to obtain a compound shown in a formula I;
in formula II, III, IV, R 1 And R is 2 Has the same definition as formula I.
13. The preparation method according to claim 12, wherein the compound of formula II has a structure represented by formula II-1, the nitrified product of formula III has a structure represented by formula III-1, and the sulfonated product of formula IV has a structure represented by formula IV-1:
in the formulas II-1, III-1 and IV-1, R 1 And R is 2 Has the same definition as formula I.
14. The preparation method according to claim 12, wherein the nitrifying agent is nitric acid and/or dinitrogen pentoxide or a mixture of at least one of nitric acid and dinitrogen pentoxide with at least one of concentrated sulfuric acid, glacial acetic acid, acetic anhydride, phosphorus pentoxide, and/or the sulfonating agent is selected from at least one of concentrated sulfuric acid, fuming sulfuric acid and sulfur trioxide; and/or the base is at least one of an alkali metal hydroxide and an alkaline earth metal hydroxide.
15. The method of claim 14, wherein the base is sodium hydroxide and/or potassium hydroxide.
16. The process according to any one of claims 12 to 15, wherein in step a), the molar ratio of the compound of formula II to the nitrating agent is (1:1) - (3:1); and/or in step b), the molar ratio of the nitrated product to the sulphonating agent is (1:1) - (5:1); and/or in step c) the amount of base added is such that the pH of the mixture of the sulphonation product and the base is adjusted to 7-14.
17. The process according to any one of claims 12 to 15, wherein in step a) the temperature of the nitration reaction is 0 to 80 ℃ and the time of the nitration reaction is 1 to 10 hours;
and/or in the step b), the temperature of the sulfonation reaction is 20-80 ℃, and the time of the sulfonation reaction is 0.5-10h.
18. Use of the viscosity reducer according to any of claims 1 to 11 or the viscosity reducer produced by the production process according to any of claims 12 to 17 in heavy oil recovery.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111151123.1A CN115872907B (en) | 2021-09-29 | 2021-09-29 | Sulfonate thickened oil viscosity reducer and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111151123.1A CN115872907B (en) | 2021-09-29 | 2021-09-29 | Sulfonate thickened oil viscosity reducer and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115872907A CN115872907A (en) | 2023-03-31 |
| CN115872907B true CN115872907B (en) | 2024-01-30 |
Family
ID=85756133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111151123.1A Active CN115872907B (en) | 2021-09-29 | 2021-09-29 | Sulfonate thickened oil viscosity reducer and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115872907B (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2264401A1 (en) * | 1971-11-22 | 1973-06-07 | Sandoz Ag | Red-scarlet reactive monazo dyes - from amino-indane -sulphonic acids and naphthols, for dyeing/printing cellulosics, wool |
| CS155849B1 (en) * | 1971-06-11 | 1974-06-24 | ||
| CN1043703A (en) * | 1988-12-22 | 1990-07-11 | 田边制药株式会社 | The method for preparing indan derivative |
| CN103773497A (en) * | 2012-10-24 | 2014-05-07 | 中国石油化工股份有限公司 | Method for increasing yield of clean fuel oil |
| CN104946226A (en) * | 2015-07-14 | 2015-09-30 | 中国石油化工股份有限公司 | Thick oil sulfonate preparing method |
-
2021
- 2021-09-29 CN CN202111151123.1A patent/CN115872907B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS155849B1 (en) * | 1971-06-11 | 1974-06-24 | ||
| DE2264401A1 (en) * | 1971-11-22 | 1973-06-07 | Sandoz Ag | Red-scarlet reactive monazo dyes - from amino-indane -sulphonic acids and naphthols, for dyeing/printing cellulosics, wool |
| CN1043703A (en) * | 1988-12-22 | 1990-07-11 | 田边制药株式会社 | The method for preparing indan derivative |
| CN103773497A (en) * | 2012-10-24 | 2014-05-07 | 中国石油化工股份有限公司 | Method for increasing yield of clean fuel oil |
| CN104946226A (en) * | 2015-07-14 | 2015-09-30 | 中国石油化工股份有限公司 | Thick oil sulfonate preparing method |
Non-Patent Citations (2)
| Title |
|---|
| Novel sulfamoyl benzamides as selective CB2 agonists with improved in vitro metabolic stability;Sellitto Ian et al;《Bioorganic & Medicinal Chemistry Letters》;第20卷(第1期);387-391 * |
| 稠油水热裂解采油技术的影响因素分析;王霞等;《内蒙古石油化工》(第8期);111-113 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115872907A (en) | 2023-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110218557B (en) | Salt-resistant Gemini zwitterionic viscoelastic surfactant and preparation method of high-salinity water-based clean fracturing fluid | |
| CN102464598B (en) | Fatty acid amide polyoxylethylene ether benzene sulfonate and preparation method thereof | |
| CN102277146B (en) | Composition for improving recovery ratio substantially and preparation method thereof | |
| CN100564476C (en) | A kind of tensio-active agent and the formula system in oil production technology | |
| CN102464974B (en) | Composition capable of greatly improving crude oil recovery ratio and preparation method thereof | |
| CN110790676B (en) | Salt-tolerant temperature-resistant zwitterion viscoelastic surfactant and preparation method of reservoir transformation working solution | |
| CN109868131B (en) | Gemini viscoelastic surfactant, preparation method and application thereof, and diverting acid | |
| CN105062458B (en) | A kind of preparation and application of the anhydrous fracturing liquid cross-linking agent of lower carbon number hydrocarbons suitable for unconventional reservoir | |
| CN105670590B (en) | Ternary composite system and surfactant suitable for high-temperature hypersalinity oil reservoir and preparation method of ternary composite system and surfactant | |
| CN102278102B (en) | Binary oil driving method for high-temperature and high-salt oil reservoir | |
| CN110665431A (en) | Preparation of sulfonic acid amphoteric gemini viscoelastic surfactant and application of surfactant in fracturing fluid | |
| CN102277148B (en) | Composition for improving recovery ratio of crude oil and preparation method thereof | |
| CN115872907B (en) | Sulfonate thickened oil viscosity reducer and preparation method and application thereof | |
| CN102277147B (en) | Oil displacement method for high-temperature high-salt oil reservoir | |
| CN104277808A (en) | Oil-displacement surfactant and preparation method thereof | |
| CN109880607A (en) | A kind of binary displacement oil agent and its application | |
| CN113652222A (en) | Temperature-resistant salt-tolerant anionic surfactant clean fracturing fluid and preparation method thereof | |
| CN116023308B (en) | Thickened oil viscosity reducer and preparation method and application thereof | |
| CN103031119A (en) | Sulfonate-containing anionic/nonionic surfactant composition and preparation method | |
| CN112707865B (en) | Zwitterionic surfactant and preparation method thereof | |
| CN103450056A (en) | Mahogany petroleum sulfonate preparation method for oil exploitation | |
| CN113896881A (en) | Alkyl naphthylamine polyether naphthalene sulfonate surfactant and preparation method and application thereof | |
| CN111087347A (en) | Alkyl imidazoline sulfonate zwitterionic surfactant, composition, preparation method and application thereof | |
| CN113881418B (en) | Alkylaniline polyether benzene sulfonate oil displacement surfactant and preparation method and application thereof | |
| CN104559987A (en) | Amide polyoxyethylene ether sulfonate betaine surfactant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |