CN102276489B - Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof - Google Patents
Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof Download PDFInfo
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Abstract
The invention relates to an alkylphenol polyoxyethylene ether carboxylate type betaine surfactant and a preparation method thereof. The objective of the invention is mainly to solve the problems in the prior art that a surfactant used as an oil displacement agent has a poor displacement effect under the condition of high temperature and high salinity and poses immense damage to strata and oil wells, corrosion to equipment and conveying pipelines, pollution to environment and the like due to presence of alkali in the surfactant. According to the invention, the technical scheme that alkylphenol polyoxyethylene ether carboxylate type betaine having a general molecular formula as described in the specification is employed, M in the formula is any one selected from the group consisting of alkali metals and alkaline earth metal, R is C1 to C20 alkyl, and n is an arbitrary integer in the range from 1 to 30 enables the problems in the prior art to be solved well and can be used in reinforced oil production in oil fields.
Description
Technical field
The present invention relates to a kind of alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof.
Background technology
The most oil fields of China, nowadays in high water-cut stage mining phase, still have more than sixty percent oil " stay-at-home " underground.And the oil field great majority of waterflooding all enter " two high " stage of high moisture, high recovery percent of reserves, the problem of " many wells low yield " is difficult to avoid.The investigation of carrying out according to the 82Ge waterflooding district to 13 main oilfield of China, production fluid water content reaches 90% at present, and output is successively decreased 1,500 ten thousand tons every year.In the face of these problems, rely on the progress of technology, go to improve oil recovery rate, increase workable reserve comprehensively, imperative.If down-hole residual petroleum is exploited out, the workable reserve that is equivalent to China doubles above.Therefore, development tertiary oil recovery is the only way which must be passed of China's oil exploitation.
So-called tertiary oil recovery, contrast primary oil recovery, secondary oil recovery.Generally, at the oil production initial stage, just utilize the natural energy recover petroleum on stratum, be called primary oil recovery, its recovery ratio is only 10% left and right.By carry out the method for recover petroleum to stratum supplementing energy, as water filling, gas injection etc., be called secondary oil recovery.Have in the world at present a large amount of Oilfield using secondary oil recovery methods, but recovery ratio generally also can only reach 25% to 40% left and right.Tertiary oil recovery, is to utilize physics, chemistry and the means such as biological, continues the remaining oil of recovery of subterranean, with this, improves the method for oil recovery factor.
In tertiary oil recovery technology means, combination flooding (polymkeric substance-tensio-active agent) has become the focus of current research, and facts have proved that this technology can improve oil recovery factor preferably.Wherein promoting agent (comprising tensio-active agent and alkali) is owing to having effects such as reducing oil water interfacial tension, make polymer flooding after underground irreducible oil (oil film, cecum wet goods) restart, thereby improve recovery ratio.
According to
E
r＝E
v*E
d
E wherein
rrepresent recovery ratio, %; E
vrepresent sweep efficiency, %; E
dfor displacement efficiency, %.Therefore improve recovery ratio, must improve sweep efficiency and displacement efficiency.The character of tensio-active agent has directly determined the displacement efficiency of compound oil displacement agent in actual production.Therefore the tensio-active agent of development of new has very important meaning for China's tertiary oil recovery industry.At present, in common oil reservoir (one, two class oil reservoirs), there is tensio-active agent to be successfully applied (CN1458219A), but the oil reservoir for high temperature, high salinity, concerning one, two class oil reservoirs, the good tensio-active agent of effect can not effectively reduce interfacial tension, and show as chemical structure mutability, serious chromatographic separation etc. is not competent.
Summary of the invention
One of technical problem to be solved by this invention is that in prior art, the oil-displacing agent oil displacement efficiency under high temperature, high salinity condition containing tensio-active agent is poor, simultaneously owing to containing alkali, injury is brought in stratum and oil well, and the problem of etching apparatus and transport pipe, a kind of Novel alkyl phenol polyethenoxy ether carboxylic acid type beet alkali surface activator is provided.Alkylphenol polyoxyethylene ether carboxylate type betaine tensio-active agent has under alkali-free, high temperature and high salt condition still can form 10
-3the advantage of the ultra low interfacial tension of mN/m, thus oil recovery factor can be improved.Technical problem solved by the invention two for the preparation method of the alkylphenol polyoxyethylene ether carboxylate type betaine tensio-active agent corresponding with one of technical solution problem is provided.This method has the features such as technique is simple, reaction conditions is gentle, and equipment requirements is lower.
For one of addressing the above problem, the technical solution used in the present invention is as follows: a kind of alkylphenol polyoxyethylene ether carboxylate type betaine tensio-active agent, its general molecular formula is
Wherein M be in basic metal, alkaline-earth metal any one, basic metal is selected from sodium, potassium, alkaline-earth metal and is selected from calcium, magnesium.R is C
1～C
20alkyl, preferable range is C
5～C
15alkyl, thiazolinyl, C
6～C
15aryl at least one.N is the arbitrary integer in 1～30, and preferable range is arbitrary integer between 2～20.
For solve the problems of the technologies described above two, the present invention adopts following technical scheme: a kind of alkylphenol polyoxyethylene ether carboxylate type betaine tensio-active agent, comprises the following steps:
A) substituted alkyl phenol polyethenoxy ether is synthetic:
By alkylphenol polyoxyethylene and excessive thionyl chloride, in mol ratio, be 0.1～5, temperature of reaction is 20～150 ℃, reacts 4～12 hours, after reaction finishes, obtains after treatment haloalkyl phenol polyethenoxy ether;
B) base phenol polyethenoxy ether-N, N-dimethyl amine synthetic:
By haloalkyl phenol polyethenoxy ether and the dimethylamine agueous solution of synthesized in a), in temperature, be 30～150 ℃, react 2～20 hours, react after finishing and obtain after treatment alkylphenol polyoxyethylene-N, N-dimethyl amine;
C) base phenol polyethenoxy ether hydroxy sulfonate type trimethyl-glycine is synthetic:
By b) in the alkylphenol polyoxyethylene-N of synthesized, N-dimethyl amine and sodium chloroacetate, at 60～100 ℃, react and within 2～8 hours, obtain target product.
In technique scheme, a) in step, the mol ratio preferable range of alkylphenol polyoxyethylene and excessive thionyl chloride is 1～3: 1, and temperature of reaction preferable range is 50～120 ℃, and reaction times preferable range is 10 hours; B) in step, temperature preferable range is 70～90 ℃, and reaction times preferable range is 10 hours; C) step reaction temperature and reaction times preferable range are at 70 ℃ 2 hours, are then warming up to and at 90 ℃, continue reaction 2～6 hours.
Betaine type surfactivity has good table, interfacial activity, can form compared with low interfacial tension at water-oil interface.Meanwhile, due to its Stability Analysis of Structures, metal ion is had to huge legendary turtle cooperation use, thereby can attempt the oil reservoir displacement of reservoir oil for high salinity, comparatively high temps.In addition, another feature of betaine type amphoteric surfactant is that its foaming properties is affected not quite by the pH of salinity and medium, thus can be in salinity higher or within the scope of pH widely for foam flooding.But expensive, the structure activity relationship of this type of tensio-active agent and oil-displacement mechanism research are very few at present.Therefore, from synthetic angle, adopt cheap raw material, development environment close friend's operational path, develop efficient, cheap, green betaine type amphoteric surfactant system, and structure activity relationship is studied, to adapt to high temperature and high salt oil deposit, improve the requirement of recovery ratio, not only there is very high theory significance, and be with a wide range of applications and practical significance.
In the present invention, alkylphenol polyoxyethylene carboxylic acid sodium type beet alkali surface activator has composition alkali-free for the composition of tertiary oil recovery, can greatly reduce the huge injury of alkali to stratum and oil well, meets environmental requirement, and can form 10 with underground crude oil
-3the ultra low interfacial tension of the mN/m order of magnitude, reaches best oil displacement efficiency and heatproof, the superior advantage of salt resistant character.
The composition that contains alkylphenol polyoxyethylene carboxylic acid sodium type beet alkali surface activator surpasses 65 ℃, salinity in formation temperature and is greater than 30000mg/L, Ca
2+, Mg
2+concentration is still can form 10 with crude oil under the marine block condition of the Shengli Oil Field of 0～1000mg/L
-3the ultra low interfacial tension of the mN/m order of magnitude, thus drive crude oil, improve recovery ratio 10% left and right, obtained good technique effect.This surfactant composition comprises following component by weight percentage:
1) 0.001～5.0% alkylphenol polyoxyethylene ether carboxylate type betaine;
2) 0.01～3.0% polymkeric substance;
3) water of surplus;
Wherein said polymkeric substance is a kind of of polyacrylamide, xanthan gum or modified polyacrylamide.
All synthetic products of the present invention can characterize by the following method, and by after purification of products, application U.S. Nicolet-5700 infrared spectrometer, adopts liquid-film method to carry out Infrared spectroscopy (surface sweeping scope 4000～400cm
-1), and spectrogram is contrasted with standard infrared spectrum, determine the chemical structure of sample, to reach the Infrared Characterization to compound of the present invention.Fig. 1～Fig. 4 is respectively alkylphenol polyoxyethylene, chloro alkylphenol polyoxyethylene, alkylphenol polyoxyethylene-N, the infrared spectrum of N dimethylamine and alkylphenol polyoxyethylene carboxylic acid sodium type trimethyl-glycine.In Fig. 1,2, in wave number, be 1609,1512,830cm
-1there is the Absorption Characteristics peak of phenyl ring in place, in wave number, is 1120～1249cm
-1there is the characteristic peak of aryl oxide C-O-C in place, in wave number, is 1070～1160cm
-1there are the existence of EO, 600～800cm in place
-1place is C-Cl characteristic peak.In Fig. 3,4,3350cm
-1the stretching vibration (being mainly that product is the aqueous solution) that left and right place is-OH, 1600cm
-1place, left and right is phenyl ring, 1249cm
-1place is aryl oxide C-O-C, 1070～1160cm
-1place has EO to exist, 1083～1192cm
-1place is the stretching vibration of C-N, 1550～1610cm
-1for-COO-stretching vibration, prove that the synthetic product of the present invention is a kind of alkylphenol polyoxyethylene ether carboxylate type betaine really.
Below by embodiment, the present invention is further elaborated.
Embodiment
[embodiment 1]
Synthesizing of amyl group (R=5) phenol polyethenoxy (n=2) ether carboxylic acid sodium type trimethyl-glycine
1) chloro amyl group (R=5) phenol polyethenoxy (n=2) ether is synthetic
In being housed, the four-hole round-bottomed flask of reflux condensate device, thermometer, agitator and gas absorbing device adds 100g amyl group (R=5) phenol polyethenoxy (n=2) ether and 57g pyridine, under stirring, be heated to 70 ℃, with dropping funnel, slowly drip 85g thionyl chloride, after dropwising, at 90 ℃, react 10 hours.After reaction finishes, by standing, the cooling layering of reactant, upper organic phase is target product, and lower floor is solid hydrochloric acid pyridinium salt.Sodium hydroxide solution with 30% is neutralized to neutrality or weakly alkaline by upper organic phase, separate inorganic salt, by hot saturated common salt water washing 5～6 times for upper organic phase, after being dried, obtain intermediate product chloro amyl group (R=5) phenol polyethenoxy (n=2) ether again, yield is 88%.
2) amyl group (R=5) phenol polyethenoxy (n=2) ether-N, N-dimethyl amine synthetic
Chloro amyl group (R=5) phenol polyethenoxy (n=2) ether 70g synthetic in step (1) is added in the four-hole boiling flask with reflux condensate device, thermometer, agitator, be heated to 77 ℃, with ethanol, dimethylamine agueous solution (33wt%) is diluted to 16wt% (be mainly and prevent dimethylamine transition volatilization), then with dropping funnel, slowly drip in flask, dropwise after 1 hour, in system, add 2g solid sodium hydroxide in order to the hydrogen chloride gas of absorption reaction generation, and measure now system pH; React again after 1 hour, then add 2g solid sodium hydroxide, make system remain weakly alkaline, react after 10 hours and finish, stratification.Upper strata is organic phase, and lower floor is water.Upper organic phase underpressure distillation is removed to unnecessary dimethylamine, ethanol, then use hot saturated common salt water washing 5～6 times, obtain target intermediate product amyl group (R=5) phenol polyethenoxy (n=2) ether-N, N-dimethyl amine, yield is 83%.
3) amyl group (R=5) phenol polyethenoxy (n=2) ether carboxylic acid sodium trimethyl-glycine is synthetic
By step 2) in synthetic amyl group (R=5) phenol polyethenoxy (n=2) ether-N, N-dimethyl amine 40g joins in the four-hole boiling flask with reflux condensate device, thermometer, agitator, be heated to 70 ℃, slowly drip 70% sodium chloroacetate aqueous solution 66g, at 70 ℃, react after 2 hours, be warming up to 90 ℃ and continue reaction 6 hours until reaction finishes, during add appropriate normal-butyl bromination ammonium and ethanol, to guarantee that two-phase fully mixes.After reaction finishes, ethanol and a small amount of water are fallen in underpressure distillation, obtain thick liquid, are ultimate aim product amyl group (R=5) phenol polyethenoxy (n=2) ether carboxylic acid sodium trimethyl-glycine.
[embodiment 2]
Synthesizing of nonyl (R=9) phenol polyethenoxy ether (n=10) carboxylic acid sodium type trimethyl-glycine
1) chloro nonyl (R=9) phenol polyethenoxy (n=10) ether is synthetic
In being housed, the four-hole round-bottomed flask of reflux condensate device, thermometer, agitator and gas absorbing device adds 100g nonyl (R=9) phenol polyethenoxy (n=10) ether and 22g pyridine, under stirring, be heated to 70 ℃, with dropping funnel, slowly drip 32.5g thionyl chloride, after dropwising, at 70 ℃, react 8 hours.After reaction finishes, by standing, the cooling layering of reactant, upper organic phase is target product, and lower floor is solid hydrochloric acid pyridinium salt.Sodium hydroxide solution with 30% is neutralized to neutrality or weakly alkaline by upper organic phase, separate inorganic salt, by hot saturated common salt water washing 5～6 times for upper organic phase, after being dried, obtain intermediate product chloro nonyl (R=9) phenol polyethenoxy (n=10) ether again, yield is 85%.
2) nonyl (R=9) phenol polyethenoxy (n=10) ether-N, N-dimethyl amine synthetic
Chloro nonyl (R=9) phenol polyethenoxy (n=10) ether 70g synthetic in step (1) is added in the four-hole boiling flask with reflux condensate device, thermometer, agitator, be heated to 85 ℃, with ethanol, dimethylamine agueous solution (33wt%) is diluted to 16wt% (be mainly and prevent dimethylamine transition volatilization), then with dropping funnel, slowly drip in flask, dropwise after 1 hour, in system, add 2g solid sodium hydroxide in order to the hydrogen chloride gas of absorption reaction generation, and measure now system pH; React again after 1 hour, then add 2g solid sodium hydroxide, make system remain weakly alkaline, react after 6 hours and finish, stratification.Upper strata is organic phase, and lower floor is water.Upper organic phase underpressure distillation is removed to unnecessary dimethylamine, ethanol, then use hot saturated common salt water washing 5～6 times, obtain target intermediate product nonyl (R=9) phenol polyethenoxy (n=10) ether-N, N-dimethyl amine, yield is 80%.
3) nonyl (R=9) phenol polyethenoxy (n=10) ether carboxylic acid sodium trimethyl-glycine is synthetic
By step 2) in synthetic nonyl (R=9) phenol polyethenoxy (n=10) ether-N, N-dimethyl amine 56g joins in the four-hole boiling flask with reflux condensate device, thermometer, agitator, be heated to 70 ℃, slowly drip sodium chloroacetate aqueous solution 76g, at 70 ℃, react after 2 hours, be warming up to 90 ℃ and continue reaction 6 hours until reaction finishes, during add appropriate normal-butyl bromination ammonium and ethanol, to guarantee that two-phase fully mixes.After reaction finishes, ethanol and a small amount of water are fallen in underpressure distillation, obtain thick liquid, are ultimate aim product nonyl (R=9) phenol polyethenoxy (n=10) ether carboxylic acid sodium trimethyl-glycine.
[embodiment 3]
Synthesizing of dodecyl phenol polyethenoxy ether (n=20) carboxylic acid sodium type trimethyl-glycine
1) chlorinated dodecane base phenol polyethenoxy (n=20) ether is synthetic
In being housed, the four-hole round-bottomed flask of reflux condensate device, thermometer, agitator and gas absorbing device adds 100g dodecyl phenol polyethenoxy (n=20) ether and 13g pyridine, under stirring, be heated to 60 ℃, with dropping funnel, slowly drip 18.7g thionyl chloride, after dropwising, at 80 ℃, react 10 hours.After reaction finishes, by standing, the cooling layering of reactant, upper organic phase is target product, and lower floor is solid hydrochloric acid pyridinium salt.Sodium hydroxide solution with 30% is neutralized to neutrality or weakly alkaline by upper organic phase, separate inorganic salt, by hot saturated common salt water washing 5～6 times for upper organic phase, after being dried, obtain intermediate product chlorinated dodecane base phenol polyethenoxy (n=20) ether again, yield is 81%.
2) dodecyl phenol polyethenoxy (n=20) ether-N, N-dimethyl amine synthetic
Chlorinated dodecane base phenol polyethenoxy (n=20) ether 70g synthetic in step (1) is added in the four-hole boiling flask with reflux condensate device, thermometer, agitator, be heated to 80 ℃, with ethanol, dimethylamine agueous solution (33wt%) is diluted to 16wt% (be mainly and prevent dimethylamine transition volatilization), then with dropping funnel, slowly drip in flask, dropwise after 1 hour, in system, add 2g solid sodium hydroxide in order to the hydrogen chloride gas of absorption reaction generation, and measure now system pH; React again after 1 hour, then add 2g solid sodium hydroxide, make system remain weakly alkaline, react after 10 hours and finish, stratification.Upper strata is organic phase, and lower floor is water.Upper organic phase underpressure distillation is removed to unnecessary dimethylamine, ethanol, then use hot saturated common salt water washing 5～6 times, obtain target intermediate product dodecyl phenol polyethenoxy (n=20) ether-N, N-dimethyl amine, yield is 83%.
3) dodecyl phenol polyethenoxy (n=20) ether carboxylic acid sodium trimethyl-glycine is synthetic
By step 2) in synthetic dodecyl phenol polyethenoxy (n=20) ether-N, N-dimethyl amine 40g joins in the four-hole boiling flask with reflux condensate device, thermometer, agitator, be heated to 75 ℃, slowly drip 70% sodium chloroacetate aqueous solution 60g, at 75 ℃, react after 2 hours, be warming up to 85 ℃ and continue reaction 4 hours until reaction finishes, during add appropriate normal-butyl bromination ammonium and ethanol, to guarantee that two-phase fully mixes.After reaction finishes, ethanol and a small amount of water are fallen in underpressure distillation, obtain thick liquid, are ultimate aim product dodecyl phenol polyethenoxy (n=20) ether carboxylic acid sodium trimethyl-glycine.
[embodiment 4]
Get nonyl (R=9) phenol polyethenoxy ether (n=10) carboxylic acid sodium type beet alkali surface activator synthetic in [embodiment 2], polyacrylamide 0.15wt%, Shengli Oil Field Crude Oil at Sea oilfield water, stirs 30 minutes, obtains a kind of Surfactant/Polymer composition.The water quality analysis of Shengli Oil Field Crude Oil at Sea block is in Table 1.At 65 ℃, the interfacial tension between said composition and the dewatered oil of Shengli Oil Field Crude Oil at Sea block extraction is as table 2.The TX-500 rotation interfacial tensimeter that interfacial tension data are produced by Texas ,Usa university is measured.
The water quality analysis of table 1 Shengli Oil Field Crude Oil at Sea block
| Project | Total mineralization mg/L | K ++Na + mg/L | Cl - mg/L | SO 4 2- mg/L | HCO 3 - mg/L | Ca 2+ mg/L | Mg 2+ mg/L |
| mg/L | 30000 | 9369 | 17703 | 1035 | 174 | 417 | 1160 |
Interfacial tension between the dewatered oil of table 2 composition and the extraction of Shengli Oil Field Crude Oil at Sea block
| Tensio-active agent (wt%) | 0.05 | 0.1 | 0.15 | 0.3 |
| Interfacial tension (mN/m) | 0.0091 | 0.0075 | 0.0069 | 0.0056 |
[embodiment 5]
In length, be 30cm, diameter is 2.5cm, and rate of permeation is 1.5m
2rock core on carry out imitation oil displacement experiment experiment.First use Shengli Oil Field sea oilfield water drive to moisture 92%, surfactant composition in metaideophone 0.3pv (rock pore volume) [embodiment 4], water drive, to moisture 100%, can improve oil recovery factor 10% left and right on the basis of water drive.
Claims (5)
1. an alkylphenol polyoxyethylene ether carboxylate type betaine, its general molecular formula is:
Wherein, wherein M is basic metal, and R is C
1～C
20alkyl, n is the arbitrary integer in 1～30.
2. according to alkylphenol polyoxyethylene ether carboxylate type betaine described in claim 1, it is characterized in that basic metal is selected from sodium, potassium.
3. according to alkylphenol polyoxyethylene ether carboxylate type betaine that claim 2 is described, it is characterized in that R is C
5～C
15alkyl, thiazolinyl, C
6～C
15aryl at least one.
4. according to alkylphenol polyoxyethylene ether carboxylate type betaine described in claim 1, the span that it is characterized in that the polymerization degree n of Soxylat A 25-7 is 2～20.
5. the preparation method of alkylphenol polyoxyethylene ether carboxylate type betaine that claim 1 is described comprises the following steps:
A) preparation of alkylphenol polyoxyethylene:
By alkylphenol polyoxyethylene and thionyl chloride, in mol ratio, be 0.1～5:1, temperature of reaction is 20～150 ℃, reacts 4～12 hours, after reaction finishes, obtains after treatment haloalkyl phenol polyethenoxy ether;
B) phenol polyethenoxy ether-N, the preparation of N-dimethyl amine:
By a) haloalkyl phenol polyethenoxy ether and the dimethylamine agueous solution of synthesized, in temperature, be 30～150 ℃, react 2～20 hours, after finishing, reaction obtains after treatment alkylphenol polyoxyethylene-N, N-dimethyl amine;
C) preparation of alkylphenol polyoxyethylene ether carboxylate type betaine:
By b) alkylphenol polyoxyethylene-N of synthesized, N-dimethyl amine and sodium chloroacetate, at 60～100 ℃, react and within 2～8 hours, obtain target product.
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| CN102964260A (en) * | 2012-12-17 | 2013-03-13 | 江南大学 | Preparation method of N,N-dimethyl-N-fatty alcohol polyethenoxy ether-base carboxymethyl lycine |
| CN103897678B (en) * | 2012-12-27 | 2016-09-07 | 中国石油化工股份有限公司 | water-in-oil drilling fluid and preparation method thereof |
| CN104479009A (en) * | 2014-11-24 | 2015-04-01 | 江南大学 | Technology for separating phycocyanin in spirulina by using polyvinyl ether carboxylate through two aqueous phase extraction |
| CN112694412B (en) * | 2019-10-22 | 2023-07-04 | 中国石油化工股份有限公司 | Betaine and preparation method and application thereof |
| CN111013484B (en) * | 2019-11-25 | 2022-02-15 | 南京科技职业学院 | Alkyl glycoside carboxyl betaine type zwitterionic surfactant and preparation method thereof |
| CN115403750B (en) * | 2022-09-29 | 2023-04-18 | 山东宝斯泰医用材料有限公司 | Carboxylic acid betaine end group-containing polyethylene glycol-polyester block copolymer and preparation method thereof |
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