CN103173197A - Gemini surfactant, preparation method thereof, and application thereof in tertiary oil recovery - Google Patents
Gemini surfactant, preparation method thereof, and application thereof in tertiary oil recovery Download PDFInfo
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- CN103173197A CN103173197A CN2013100685447A CN201310068544A CN103173197A CN 103173197 A CN103173197 A CN 103173197A CN 2013100685447 A CN2013100685447 A CN 2013100685447A CN 201310068544 A CN201310068544 A CN 201310068544A CN 103173197 A CN103173197 A CN 103173197A
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Abstract
The invention discloses a Gemini surfactant represented by a structural formula (I), wherein R1 is C9, C11, C13, or C15 alkyl, R2 is CH2COONa or CH2CH(OH)CH2SO3Na, and R3 is CH2COO<-> or CH2CH(OH)CH2SO3<->. When the Gemini surfactant provided by the invention is used in oil field tertiary oil recovery, surface tension and oil-water interfacial tension can be effectively reduced. Especially, under relatively low alkalinity, crude oil oil-water interfacial tension can reach an ultralow level. The Gemini surfactant has high wetting efficiency, high penetration efficiency, high emulsification efficiency, and good formulation. The preparation process is simple, and the cost is low. The Gemini surfactant and the method are suitable for industrialized productions.
Description
Technical field
The present invention relates to a kind of Gemini surface active agent for the tertiary oil recovery chemical oil displacement agent and preparation method thereof.
Background technology
Along with the development of modern social economy, people make this non-renewable resource of oil become more and more valuable for the continuous increase of petroleum resources demand and the continuous minimizing of prospective oil.The oil field high moisture or ultra-high water-containing occurs at the later stage of secondary oil recovery, and the crude production rate rate of decline is accelerated, and economic benefit descends.In order to improve the recovery ratio in oil field, the Application and Development of tertiary oil recovery technology is imperative.Chemical combined flooding is the flooding system that forms with tensio-active agent, alkali, polymkeric substance, and wherein the effect of tensio-active agent is the interfacial tension that reduces between profit, improves displacement efficiency; The effect that adds alkali is that the acid of crude oil PetroChina Company Limited. is transformed into the oil hydrochlorate, makes it to become natural surface active agent, can reduce the consumption of tensio-active agent, reduces the cost of flooding system with this; The effect of polymkeric substance is to improve flooding system viscosity, is conducive to improve their sweep efficiency.Combination flooding is given full play to the synergy between each component, increases substantially oil displacement efficiency.
At present, the gordian technique of restriction combination flooding technology popularization application is the development that complex oil displacing is used tensio-active agent.In recent years, during " 12 ", the surfactant oil displacement demand will rise to 180,000 tons from 120,000 tons, and development is efficient, cheap, free of contamination complex oil displacing receives much concern with the work of tensio-active agent.Traditional tensio-active agent is that the single parent is water base, the amphiphile, amphiphilic molecule of single hydrophobic group, such molecular structure characteristics cause its form in solution the adsorption at gas-liquid surface layer with body mutually in the Ordering process of aggregate molecule, be subject to hydrophobic association and like charges and repel two kinds of opposite effect power, its surface-active raising is restricted.Gemini surface active agent is the brand-new tensio-active agent of a class, because this structure is by two hydrophilic radicals, two hydrophobic groupings and is connected and connects a base key and close the special construction compound that forms, make it have a series of peculiar properties such as ultra low interfacial tension, low micelle-forming concentration, low Kraff point, good lime soap dispersing power and wettability, thereby cause great concern.
Summary of the invention
The purpose of this invention is to provide a kind of Gemini surface active agent that has low toxicity, easily degrades.
Another object of the present invention is to provide the preparation method of above-mentioned Gemini surface active agent.
A further object of the invention is to provide the application as chemical oil displacement agent in tertiary oil recovery of above-mentioned Gemini surface active agent.
Implementation procedure of the present invention is as follows:
The Gemini surface active agent of structural formula (I) expression,
Wherein, R
1Be C
9, C
11, C
13, C
15Alkyl, R
2Be CH
2COONa or CH
2CH (OH) CH
2SO
3Na, R
3Be CH
2COO
-Or CH
2CH (OH) CH
2SO
3 -
The preparation method of the Gemini surface active agent of structural formula (I) expression comprises the following steps:
(1) with mol ratio be the R of 2:1
1COOH and diethylenetriamine mix;
(2) 150-170 ℃ of reaction, decompression steams the water that reaction generates;
(3) cooling, recrystallization gets wax-like intermediate
(4) intermediate, sodium chloroacetate or 3-chlorine-2-hydroxyl propanesulfonate, the sodium hydroxide of 1:2:2 is water-soluble, 80-90 ℃ of reaction 3h can obtain the Gemini surface active agent shown in structural formula (I);
Wherein, R
1Be C
9, C
11, C
13, C
15Alkyl.
In above-mentioned steps (3), recrystallization in acetone.
Advantage of the present invention and positively effect:
1, the Gemini surface active agent of gained of the present invention, be used for tertiary oil production in oil field, as oil-displacing agent preparation composite oil-displacing system, can effectively reduce surface tension and oil water interfacial tension, particularly under lower basicity, all can make the crude oil oil water interfacial tension reach ultralow (10
-3MN/m), and have wetting, infiltration efficiently and emulsification, compatibleness is good; 2, products obtained therefrom of the present invention has hypotoxicity, and biological degradation preferably is environment friendly and pollution-free, the characteristics such as good anti-salt, high temperature resistance; 3, raw material of the present invention is easy to get, and preparation technology is simple, and cost is low, is suitable for suitability for industrialized production.
Embodiment
For a more clear understanding of the present invention, the present invention is described in further detail for the embodiment that provides by the contriver below.
Embodiment 1
Add 200mol n-capric acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 150 ℃ by 50 ℃ in 5h, the water that constantly generates except dereaction.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add the Mono Chloro Acetic Acid by 100mol, the solution that 200mol sodium hydroxide, 1800L water are made into.Be warming up to 80-90 ℃ of reaction 3h, can synthesize and obtain Gemini surface active agent 1.
1H NMR(D
2O， 400MHz) δ (ppm): 4. 72(s， 2H)， 4.15 (s， 2H)， 3.71-3.80(m， 8H)， 2.33(t， 4H)， 1.61-1.68(m， 4H)， 1.27-1.40(m， 24H)， 0.93(t， 6H)。
Embodiment 2
Add 200mol lauric acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 160 ℃ by 50 ℃ in 5h, the water that constantly generates except dereaction.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add the Mono Chloro Acetic Acid by 100mol, the solution that 200mol sodium hydroxide, 1800L water are made into.Be warming up to 80-90 ℃ of reaction 3h, can synthesize and obtain Gemini surface active agent 2.
1H NMR(D
2O， 400MHz) δ (ppm): 4. 75(s， 2H)， 4.18 (s， 2H)， 3.69-3.82(m， 8H)， 2.38(t， 4H)， 1.60-1.66(m， 4H)， 1.27-1.45(m， 32H)， 0.95(t， 6H)。
Embodiment 3
Add 200mol myristic acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 170 ℃ by 50 ℃ in 5h, constantly go out the water that dereaction generates.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add the Mono Chloro Acetic Acid by 100mol, the solution that 200mol sodium hydroxide, 1800L water are made into.Be warming up to 80-90 ℃ of reaction 3h, can synthesize and obtain Gemini surface active agent 3.
1H NMR(D
2O， 400MHz) δ (ppm): 4. 74(s， 2H)， 4.17 (s， 2H)， 3.72-3.85(m， 8H)， 2.35(t， 4H)， 1.62-1.68(m， 4H)， 1.27-1.43(m， 40H)， 0.91(t， 6H)。
Embodiment 4
Add 200mol palmitinic acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 170 ℃ by 50 ℃ in 5h, the water that constantly generates except dereaction.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add the Mono Chloro Acetic Acid by 100mol, the solution that 200mol sodium hydroxide, 1800L water are made into.Be warming up to 80-90 ℃ of reaction 3h, can synthesize and obtain Gemini surface active agent 4.
1H NMR(D
2O， 400MHz) δ (ppm): 4. 70(s， 2H)， 4.15 (s， 2H)， 3.70-3.87(m， 8H)， 2.33(t， 4H)， 1.58-1.62(m， 4H)， 1.31-1.45(m， 48H)， 0.93(t， 6H)。
Embodiment 5
Add 200mol n-capric acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 160 ℃ by 50 ℃ in 5h, the water that constantly generates except dereaction.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add by 100mol 3-chlorine-2-hydroxyl propanesulfonate, the solution that 100mol sodium hydroxide, 1800L water are made into is warming up to 80-90 ℃ of reaction 3h, can synthesize to obtain Gemini surface active agent 5.
1H NMR(D
2O， 400MHz) δ (ppm): 4.30-4.34(m， 2H)， 3.87(d， 4H)， 3.75(t， 4H)， 3.70(t， 4H)， 3.50(t， 4H)， 2.28 (t， 4H)， 1.57(m， 4H)， 1.29-1.45(m， 24H)， 0.93(t， 6H)。
Embodiment 6
Add 200mol lauric acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 170 ℃ by 50 ℃ in 5h, the water that constantly generates except dereaction.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add by 100mol3-chlorine-2-hydroxyl propanesulfonate, the solution that 100mol sodium hydroxide, 1800L water are made into is warming up to 80-90 ℃ of reaction 3h, can synthesize to obtain Gemini surface active agent 6.
1H NMR(D
2O， 400MHz) δ (ppm): 4.32-4.35(m， 2H)， 3.90(d， 4H)， 3.78(t， 4H)， 3.68(t， 4H)， 3.51(t， 4H)， 2.33(t， 4H)， 1.58(m， 4H)， 1.29-1.48(m， 32H)， 0.96(t， 6H)。
Embodiment 7
Add 200mol myristic acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 170 ℃ by 50 ℃ in 5h, the water that constantly generates except dereaction.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add by 100mol3-chlorine-2-hydroxyl propanesulfonate, the solution that 100mol sodium hydroxide, 1800L water are made into is warming up to 80-90 ℃ of reaction 3h, can synthesize to obtain Gemini surface active agent 7.
1H NMR(D
2O， 400MHz) δ (ppm): 4.30-4.35(m， 2H)， 3.91(d， 4H)， 3.75(t， 4H)， 3.62(t， 4H)， 3.48(t， 4H)， 2.38(t， 4H)， 1.55(m， 4H)， 1.32-1.45(m， 40H)， 0.91(t， 6H)。
Embodiment 8
Add 200mol palmitinic acid and 100mol diethylenetriamine in reactor, heated and stirred makes fusing fully, obtains light yellow transparent liquid, under 26.7kPa, stir and separate hot mixt, make the temperature of reaction rising, rise to 170 ℃ by 50 ℃ in 5h, the water that constantly generates except dereaction.The decompression reaction mixture obtains light yellow solid to room temperature, and the crude product acetone recrystallization obtains wax-like intermediate.Get the 50mol intermediate, slowly add by 100mol3-chlorine-2-hydroxyl propanesulfonate, the solution that 100mol sodium hydroxide, 1800L water are made into is warming up to 80-90 ℃ of reaction 3h, can synthesize to obtain Gemini surface active agent 8.
1H NMR(D
2O， 400MHz) δ (ppm): 4.31-4.36(m， 2H)， 3.83(d， 4H)， 3.75(t， 4H)， 3.62(t， 4H)， 3.44(t， 4H)， 2.35(t， 4H)， 1.52(m， 4H)， 1.25-1.45(m， 48H)， 0.93(t， 6H)。
Embodiment 9
Ternary composite displacement system is comprised of compound alkali, compound surfactant and polymkeric substance, and wherein each constituent mass content is: compound alkali: 0.2-2.0 part, compound surfactant: 0.05-0.5 part, polymkeric substance: 0.8-1.2 part.
The Gemini surface active agent that embodiment 1-8 prepares is applied to the ternary composite driving experimental result and sees Table 1.The interfacial tension condition determination: measuring temperature is 45 ℃, and determining instrument is " TEXAS-500 " rotation interfacial tensimeter.
The experiment profit is oil recovery factory's deeply treating wastewater and dewatered oil.Compound alkali concn is 0.5%, and the high molecular polymerization substrate concentration is 1000mg/L.Gemini surface active agent involved in the present invention can be used as the tensio-active agent of ternary composite displacement system as can be seen from the above table, is applied among tertiary oil recovery, and all energy and crude oil form ultra low interfacial tension.
Claims (4)
1. the Gemini surface active agent of structural formula (I) expression,
Wherein, R
1Be C
9, C
11, C
13, C
15Alkyl, R
2Be CH
2COONa or CH
2CH (OH) CH
2SO
3Na, R
3Be CH
2COO
-Or CH
2CH (OH) CH
2SO
3 -
2. the preparation method of Gemini surface active agent claimed in claim 1 is characterized in that comprising the following steps:
(1) with mol ratio be the R of 2:1
1COOH and diethylenetriamine mix;
(2) 150-170 ℃ of reaction, decompression steams the water that reaction generates;
(3) cooling, recrystallization gets wax-like intermediate
(4) intermediate, sodium chloroacetate or 3-chlorine-2-hydroxyl propanesulfonate, the sodium hydroxide of 1:2:2 is water-soluble, 80-90 ℃ of reaction 3h can obtain the Gemini surface active agent shown in structural formula (I);
Wherein, R
1Be C
9, C
11, C
13, C
15Alkyl.
3. the preparation method of Gemini surface active agent according to claim 2 is characterized in that: in step (3), and recrystallization in acetone.
4. the application of Gemini surface active agent claimed in claim 1 in tertiary oil recovery.
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Cited By (6)
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| CN104927823A (en) * | 2015-05-19 | 2015-09-23 | 唐山冀油瑞丰化工有限公司 | Dianionic surfactant oil displacement agent and preparation method therefor and application thereof |
| CN105642185A (en) * | 2014-10-22 | 2016-06-08 | 中国石油化工股份有限公司 | Anionic-cationic-nonionic surfactant, preparation method therefor and application of anionic-cationic-nonionic surfactant |
| CN106582435A (en) * | 2016-11-30 | 2017-04-26 | 江南大学 | Synthetic process of bisamide type bisamide surfactant |
| CN109722230A (en) * | 2017-10-27 | 2019-05-07 | 中石化石油工程技术服务有限公司 | A kind of oil base drilling fluid emulsifier and preparation method thereof and drilling fluid |
| CN111154468A (en) * | 2020-01-06 | 2020-05-15 | 西南石油大学 | Selective water shutoff agent for oilfield water shutoff |
| CN116693429A (en) * | 2023-03-29 | 2023-09-05 | 重庆市泓择石油科技有限公司 | Variable viscosity amphiphilic structure type fracturing fluid thickener and preparation method and application thereof |
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| CN104927823A (en) * | 2015-05-19 | 2015-09-23 | 唐山冀油瑞丰化工有限公司 | Dianionic surfactant oil displacement agent and preparation method therefor and application thereof |
| CN104927823B (en) * | 2015-05-19 | 2018-01-26 | 唐山冀油瑞丰化工有限公司 | Dianionic surfactant oil displacement agent and its preparation method and application |
| CN106582435A (en) * | 2016-11-30 | 2017-04-26 | 江南大学 | Synthetic process of bisamide type bisamide surfactant |
| CN106582435B (en) * | 2016-11-30 | 2019-04-09 | 江南大学 | A kind of synthesis technology of bisamide type glycine surfactant |
| CN109722230A (en) * | 2017-10-27 | 2019-05-07 | 中石化石油工程技术服务有限公司 | A kind of oil base drilling fluid emulsifier and preparation method thereof and drilling fluid |
| CN111154468A (en) * | 2020-01-06 | 2020-05-15 | 西南石油大学 | Selective water shutoff agent for oilfield water shutoff |
| CN116693429A (en) * | 2023-03-29 | 2023-09-05 | 重庆市泓择石油科技有限公司 | Variable viscosity amphiphilic structure type fracturing fluid thickener and preparation method and application thereof |
| CN116693429B (en) * | 2023-03-29 | 2024-01-26 | 重庆市泓择石油科技有限公司 | Variable viscosity amphiphilic structure type fracturing fluid thickener and preparation method and application thereof |
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