CN102276489A - Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof - Google Patents
Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof Download PDFInfo
- Publication number
- CN102276489A CN102276489A CN2010101996736A CN201010199673A CN102276489A CN 102276489 A CN102276489 A CN 102276489A CN 2010101996736 A CN2010101996736 A CN 2010101996736A CN 201010199673 A CN201010199673 A CN 201010199673A CN 102276489 A CN102276489 A CN 102276489A
- Authority
- CN
- China
- Prior art keywords
- alkylphenol polyoxyethylene
- reaction
- hours
- glycine
- carboxylic acid
- 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.)
- Granted
Links
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 carboxylic acid type trimethyl-glycine and preparation method thereof.
Background technology
The most oil fields of China nowadays are in the high water-cut stage mining phase, still have the oil " stay-at-home " more than sixty percent underground.And the oil field great majority of waterflooding all enter " two high " stage of high moisture, high recovery percent of reserves, and the problem of " many wells low yield " is difficult to avoid.According to 82 investigation that the waterflooding district carries out to 13 main oilfield of China, output liquid 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 development of technology, go to improve oil recovery rate, increase workable reserve comprehensively, imperative.If the down-hole residual petroleum is exploited out, the workable reserve that is equivalent to China doubles above.Therefore, the 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 only is about 10%.By the method for coming recover petroleum,, be called secondary oil recovery as water filling, gas injection etc. to the stratum supplementing energy.Existing in the world at present a large amount of Oilfield using secondary oil recovery methods, but recovery ratio generally also can only reach about 25% to 40%.Tertiary oil recovery then is to utilize means such as physics, chemistry and biology, continues the remaining oil of recovery of subterranean, improves the method for oil recovery factor with this.
In the 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 have effects such as reducing oil water interfacial tension, make polymer flooding after subterranean irreducible oil (oil film, cecum wet goods) restart, thereby improve recovery ratio.
According to
E
r＝E
v*E
d
E wherein
rThe expression recovery ratio, %; E
vThe expression sweep efficiency, %; E
dBe displacement efficiency, %.Therefore improve recovery ratio, must improve sweep efficiency and displacement efficiency.The character of tensio-active agent has then directly determined the displacement efficiency of compound oil displacement agent in the 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), tensio-active agent has been arranged by successful Application (CN1458219A), but oil reservoir for high temperature, high salinity, concerning one, two class oil reservoirs effect preferably tensio-active agent then can not effectively reduce interfacial tension, and show as the chemical structure mutability, serious chromatographic separation or the like is not competent.
Summary of the invention
One of technical problem to be solved by this invention is that to contain oil-displacing agent oil displacement efficiency under high temperature, high salinity condition of tensio-active agent in the prior art poor, simultaneously owing to contain alkali, injury is brought on stratum and oil well, and the problem of etching apparatus and transport pipe, a kind of novel alkylphenol polyoxyethylene carboxylic acid type beet alkali surface activator is provided.Alkylphenol polyoxyethylene carboxylic acid type beet alkali surface activator 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 with the corresponding alkylphenol polyoxyethylene carboxylic acid type of one of technical solution problem beet alkali surface activator is provided.This method has characteristics such as technology 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 carboxylic acid type beet alkali surface activator, its general molecular formula is
Wherein M be in basic metal, the 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 a.N is the arbitrary integer in 1～30, and preferable range is an 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 carboxylic acid type beet alkali surface activator may further comprise the steps:
A) the substituted alkyl phenol polyethenoxy ether is synthetic:
Is 0.1～5 with alkylphenol polyoxyethylene and excessive thionyl chloride in mol ratio, and temperature of reaction is 20～150 ℃, reacts 4～12 hours, and reaction obtains the haloalkyl phenol polyethenoxy ether after finishing after treatment;
B) basic phenol polyethenoxy ether-N, N-dimethyl amine synthetic:
With institute's synthetic haloalkyl phenol polyethenoxy ether in a) and dimethylamine agueous solution, be 30～150 ℃ in temperature, react 2～20 hours, obtain alkylphenol polyoxyethylene-N after treatment, the N-dimethyl amine after the reaction end;
C) basic phenol polyethenoxy ether hydroxy sulfonate type trimethyl-glycine is synthetic:
With b) in the synthetic alkylphenol polyoxyethylene-N of institute, N-dimethyl amine and sodium chloroacetate react and obtained target product in 2～8 hours under 60～100 ℃.
In the technique scheme, a) the mol ratio preferable range of alkylphenol polyoxyethylene and excessive thionyl chloride is 1～3: 1 in the step, and the temperature of reaction preferable range is 50～120 ℃, and the reaction times preferable range is 10 hours; B) the temperature preferable range is 70～90 ℃ in the step, and the reaction times preferable range is 10 hours; C) step reaction temperature and reaction times preferable range be 70 ℃ following 2 hours, be warming up to 90 ℃ then and continue down reaction 2～6 hours.
The betaine type surfactivity has good table, interfacial activity, can form than low interfacial tension at water-oil interface.Simultaneously, owing to its Stability Analysis of Structures, metal ion is had huge legendary turtle cooperation usefulness, thereby can attempt being used for the oil reservoir displacement of reservoir oil of high salinity, comparatively high temps.In addition, another characteristics of betaine type amphoteric surfactant are that its foaming properties is influenced not quite by the pH of salinity and medium, thereby can be in salinity higher or be used for foam flooding in the pH scope widely.But this type of tensio-active agent costs an arm and a leg at present, the research of structure activity relationship and oil-displacement mechanism is very few.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 the requirement that high temperature and high salt oil deposit improves recovery ratio, not only have very high theory significance, and be with a wide range of applications and practical significance.
The composition that alkylphenol polyoxyethylene carboxylic acid sodium type beet alkali surface activator is used for tertiary oil recovery among the present invention has the composition alkali-free, can significantly reduce the huge injury of alkali to stratum and oil well, compliance with environmental protection requirements, 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 greater than 30000mg/L in formation temperature, 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 about 10%, obtained better technical effect.This surfactant composition comprises following component by weight percentage:
1) 0.001～5.0% alkylphenol polyoxyethylene carboxylic acid type trimethyl-glycine;
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, after purification of products, use U.S. Nicolet-5700 infrared spectrometer, adopt liquid-film method to carry out Infrared spectroscopy (surface sweeping scope 4000～400cm
-1), and spectrogram and standard infrared spectrum contrasted, determine the chemical structure of sample, to reach 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.Among Fig. 1,2, be 1609,1512 in wave number, 830cm
-1The absorption characteristic peak of phenyl ring appears in the place, is 1120～1249cm in wave number
-1The characteristic peak of aryl oxide C-O-C appears in the place, is 1070～1160cm in wave number
-1There are the existence of EO, 600～800cm in the place
-1The place is the C-Cl characteristic peak.Among Fig. 3,4,3350cm
-1About locate stretching vibration (mainly being that product is the aqueous solution) for-OH, 1600cm
-1About locate to be phenyl ring, 1249cm
-1The place is aryl oxide C-O-C, 1070～1160cm
-1The place has EO to have 1083～1192cm
-1The place is the stretching vibration of C-N, 1550～1610cm
-1For-the COO-stretching vibration, prove that synthetic product of the present invention is a kind of alkylphenol polyoxyethylene carboxylic acid type trimethyl-glycine really.
The present invention is further elaborated below by embodiment.
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, be heated to 70 ℃ under stirring, slowly drip the 85g thionyl chloride with dropping funnel, dropwise the back and reacted 10 hours down at 90 ℃.Layering is left standstill, cooled off to reaction with reactant after finishing, and upper organic phase is a target product, and lower floor is a solid hydrochloric acid pyridinium salt.Sodium hydroxide solution with 30% is neutralized to neutrality or weakly alkaline with upper organic phase, tell inorganic salt, with upper organic phase hot saturated common salt water washing 5～6 times, obtain intermediate product chloro amyl group (R=5) phenol polyethenoxy (n=2) ether after the drying again, yield is 88%.
2) amyl group (R=5) phenol polyethenoxy (n=2) ether-N, N-dimethyl amine synthetic
Synthetic chloro amyl group (R=5) phenol polyethenoxy (n=2) ether 70g adding in the step (1) is had in the four-hole boiling flask of 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), slowly drip in the flask with dropping funnel then, after dropwising 1 hour, in system, add the hydrogen chloride gas that the 2g solid sodium hydroxide generates in order to absorption reaction, and measure system pH this moment; After reacting 1 hour again, add the 2g solid sodium hydroxide again, the system that makes remains weakly alkaline, reacts after 10 hours and finishes, standing demix.The upper strata is an organic phase, and lower floor is a water.Unnecessary dimethylamine, ethanol are removed in the upper organic phase underpressure distillation, use hot saturated common salt water washing 5～6 times then, obtain target intermediate product amyl group (R=5) phenol polyethenoxy (n=2) ether-N, N-dimethyl amine, yield are 83%.
3) amyl group (R=5) phenol polyethenoxy (n=2) ether carboxylic acid sodium trimethyl-glycine is synthetic
With step 2) middle synthetic amyl group (R=5) phenol polyethenoxy (n=2) ether-N, N-dimethyl amine 40g joins in the four-hole boiling flask that has reflux condensate device, thermometer, agitator, be heated to 70 ℃, the sodium chloroacetate aqueous solution 66g of slow dropping 70%, after reacting 2 hours under 70 ℃, be warming up to 90 ℃ and continue reaction 6 hours and finish until reaction, during add an amount of normal-butyl bromination ammonium and ethanol, to guarantee the two-phase thorough mixing.After reaction finished, ethanol and less water were 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, be heated to 70 ℃ under stirring, slowly drip the 32.5g thionyl chloride with dropping funnel, dropwise the back and reacted 8 hours down at 70 ℃.Layering is left standstill, cooled off to reaction with reactant after finishing, and upper organic phase is a target product, and lower floor is a solid hydrochloric acid pyridinium salt.Sodium hydroxide solution with 30% is neutralized to neutrality or weakly alkaline with upper organic phase, tell inorganic salt, with upper organic phase hot saturated common salt water washing 5～6 times, obtain intermediate product chloro nonyl (R=9) phenol polyethenoxy (n=10) ether after the drying again, yield is 85%.
2) nonyl (R=9) phenol polyethenoxy (n=10) ether-N, N-dimethyl amine synthetic
Synthetic chloro nonyl (R=9) phenol polyethenoxy (n=10) ether 70g adding in the step (1) is had in the four-hole boiling flask of 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), slowly drip in the flask with dropping funnel then, after dropwising 1 hour, in system, add the hydrogen chloride gas that the 2g solid sodium hydroxide generates in order to absorption reaction, and measure system pH this moment; After reacting 1 hour again, add the 2g solid sodium hydroxide again, the system that makes remains weakly alkaline, reacts after 6 hours and finishes, standing demix.The upper strata is an organic phase, and lower floor is a water.Unnecessary dimethylamine, ethanol are removed in the upper organic phase underpressure distillation, use hot saturated common salt water washing 5～6 times then, obtain target intermediate product nonyl (R=9) phenol polyethenoxy (n=10) ether-N, N-dimethyl amine, yield are 80%.
3) nonyl (R=9) phenol polyethenoxy (n=10) ether carboxylic acid sodium trimethyl-glycine is synthetic
With step 2) middle synthetic nonyl (R=9) phenol polyethenoxy (n=10) ether-N, N-dimethyl amine 56g joins in the four-hole boiling flask that has reflux condensate device, thermometer, agitator, be heated to 70 ℃, slowly drip sodium chloroacetate aqueous solution 76g, after reacting 2 hours under 70 ℃, be warming up to 90 ℃ and continue reaction 6 hours and finish until reaction, during add an amount of normal-butyl bromination ammonium and ethanol, to guarantee the two-phase thorough mixing.After reaction finished, ethanol and less water were 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, be heated to 60 ℃ under stirring, slowly drip the 18.7g thionyl chloride with dropping funnel, dropwise the back and reacted 10 hours down at 80 ℃.Layering is left standstill, cooled off to reaction with reactant after finishing, and upper organic phase is a target product, and lower floor is a solid hydrochloric acid pyridinium salt.Sodium hydroxide solution with 30% is neutralized to neutrality or weakly alkaline with upper organic phase, tell inorganic salt, with upper organic phase hot saturated common salt water washing 5～6 times, obtain intermediate product chlorinated dodecane base phenol polyethenoxy (n=20) ether after the drying again, yield is 81%.
2) dodecyl phenol polyethenoxy (n=20) ether-N, N-dimethyl amine synthetic
Synthetic chlorinated dodecane base phenol polyethenoxy (n=20) ether 70g adding in the step (1) is had in the four-hole boiling flask of 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), slowly drip in the flask with dropping funnel then, after dropwising 1 hour, in system, add the hydrogen chloride gas that the 2g solid sodium hydroxide generates in order to absorption reaction, and measure system pH this moment; After reacting 1 hour again, add the 2g solid sodium hydroxide again, the system that makes remains weakly alkaline, reacts after 10 hours and finishes, standing demix.The upper strata is an organic phase, and lower floor is a water.Unnecessary dimethylamine, ethanol are removed in the upper organic phase underpressure distillation, use hot saturated common salt water washing 5～6 times then, obtain target intermediate product dodecyl phenol polyethenoxy (n=20) ether-N, N-dimethyl amine, yield are 83%.
3) dodecyl phenol polyethenoxy (n=20) ether carboxylic acid sodium trimethyl-glycine is synthetic
With step 2) middle synthetic dodecyl phenol polyethenoxy (n=20) ether-N, N-dimethyl amine 40g joins in the four-hole boiling flask that has reflux condensate device, thermometer, agitator, be heated to 75 ℃, the sodium chloroacetate aqueous solution 60g of slow dropping 70%, after reacting 2 hours under 75 ℃, be warming up to 85 ℃ and continue reaction 4 hours and finish until reaction, during add an amount of normal-butyl bromination ammonium and ethanol, to guarantee the two-phase thorough mixing.After reaction finished, ethanol and less water were 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 synthetic nonyl (R=9) phenol polyethenoxy ether (n=10) carboxylic acid sodium type beet alkali surface activator in [embodiment 2], polyacrylamide 0.15wt%, the marine crude oil oilfield of Shengli Oil Field water stirred 30 minutes, obtained a kind of tensio-active agent/polymer composition.The marine former oilfield water quality analysis of Shengli Oil Field sees Table 1.Under 65 ℃, interfacial tension such as table 2 between the dewatered oil of the marine former oilfield extraction of said composition and Shengli Oil Field.The interfacial tension data are dripped interfacial tensimeter mensuration by the TX-500 rotation that Texas ,Usa university produces.
The marine former oilfield water quality analysis of table 1 Shengli Oil Field
| 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 the marine former oilfield extraction of table 2 composition and Shengli Oil Field
| 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 is 30cm, and diameter is 2.5cm, and rate of permeation is 1.5m
2Rock core on carry out imitation oil displacement experiment experiment.Earlier with Shengli Oil Field sea oilfield water drive to moisture 92%, surfactant composition among the metaideophone 0.3pv (rock pore volume) [embodiment 4], water drive can improve oil recovery factor about 10% to moisture 100% on the basis of water drive.
Claims (5)
1. alkylphenol polyoxyethylene carboxylic acid type trimethyl-glycine, its general molecular formula is:
Wherein, wherein M be in basic metal, the alkaline-earth metal any one, R is C
1～C
20Alkyl, n is the arbitrary integer in 1～30;
2. according to alkylphenol polyoxyethylene carboxylic acid type trimethyl-glycine described in the claim 1, it is characterized in that basic metal is selected from sodium, potassium, alkaline-earth metal and is selected from calcium, magnesium.
3. describe alkylphenol polyoxyethylene carboxylic acid type trimethyl-glycine according to claim 2, it is characterized in that R is C
5～C
15Alkyl, thiazolinyl, C
6～C
15Aryl at least a.
4. according to alkylphenol polyoxyethylene carboxylic acid type trimethyl-glycine described in the claim 1, the span that it is characterized in that the polymerization degree n of Soxylat A 25-7 is 2～20.
5. claim 1 preparation method that describes alkylphenol polyoxyethylene carboxylic acid type trimethyl-glycine may further comprise the steps:
A) preparation of alkylphenol polyoxyethylene:
Is 0.1～5: 1 with alkylphenol polyoxyethylene and thionyl chloride in mol ratio, and temperature of reaction is 20～150 ℃, reacts 4～12 hours, and reaction obtains the haloalkyl phenol polyethenoxy ether after finishing after treatment;
B) phenol polyethenoxy ether-N, the preparation of N-dimethyl amine:
With a) institute's synthetic haloalkyl phenol polyethenoxy ether and dimethylamine agueous solution, be 30～150 ℃ in temperature, to react 2～20 hours, reaction obtains alkylphenol polyoxyethylene-N, the N-dimethyl amine after finishing after treatment;
C) preparation of phenol polyethenoxy ether hydroxy sulfonate type trimethyl-glycine:
With b) the synthetic alkylphenol polyoxyethylene-N of institute, N-dimethyl amine and sodium chloroacetate react and obtained target product in 2～8 hours under 60～100 ℃.
In the technique scheme, a) mol ratio of rapid middle alkylphenol polyoxyethylene and excessive thionyl chloride is preferably 1～3: 1, and the temperature of reaction preferable range is 50～120 ℃, the reaction times is preferably 10 hours; B) preferred temperature is 70～90 ℃ in rapid, and the reaction times is preferably 10 hours; C) rapid temperature of reaction and reaction times be preferably 70 ℃ following 2 hours, be warming up to 90 ℃ then and continue reaction 2～6 hours down.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010199673.6A CN102276489B (en) | 2010-06-11 | 2010-06-11 | Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010199673.6A CN102276489B (en) | 2010-06-11 | 2010-06-11 | Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102276489A true CN102276489A (en) | 2011-12-14 |
| CN102276489B CN102276489B (en) | 2014-03-26 |
Family
ID=45102280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201010199673.6A Active CN102276489B (en) | 2010-06-11 | 2010-06-11 | Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102276489B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103897678A (en) * | 2012-12-27 | 2014-07-02 | 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 |
| CN111013484A (en) * | 2019-11-25 | 2020-04-17 | 南京科技职业学院 | Alkyl glycoside carboxyl betaine type zwitterionic surfactant and preparation method thereof |
| CN112694412A (en) * | 2019-10-22 | 2021-04-23 | 中国石油化工股份有限公司 | Betaine and preparation method and application thereof |
| CN115403750A (en) * | 2022-09-29 | 2022-11-29 | 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106905944A (en) * | 2017-02-28 | 2017-06-30 | 陕西延长石油(集团)有限责任公司研究院 | A kind of preparation method of carboxylic acid betaine type Molecular Deposition Film Oil-displacing Agent used for tertiary oil recovery |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329268A (en) * | 1979-10-03 | 1982-05-11 | Gaf Corporation | Polyethyleneoxy sulfonate surfactants |
| EP0206678A1 (en) * | 1985-06-15 | 1986-12-30 | The British Petroleum Company p.l.c. | Preparation of surfactants |
| CN101220237A (en) * | 2008-01-22 | 2008-07-16 | 武汉理工大学 | Self-emulsifying aqueous epoxide resin paint and method for producing the same |
-
2010
- 2010-06-11 CN CN201010199673.6A patent/CN102276489B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329268A (en) * | 1979-10-03 | 1982-05-11 | Gaf Corporation | Polyethyleneoxy sulfonate surfactants |
| EP0206678A1 (en) * | 1985-06-15 | 1986-12-30 | The British Petroleum Company p.l.c. | Preparation of surfactants |
| CN101220237A (en) * | 2008-01-22 | 2008-07-16 | 武汉理工大学 | Self-emulsifying aqueous epoxide resin paint and method for producing the same |
Non-Patent Citations (2)
| Title |
|---|
| ESTEVE VALLS等: "Synthesis and characterization of new amphiphilic phosphines and palladium metallosurfactants", 《ORGANOMETALLICS》, vol. 21, no. 12, 16 May 2002 (2002-05-16), pages 2473 - 2480 * |
| 韩霞等: "驱油用石油磺酸盐的研究及其应用", 《日用化学品科学》, vol. 31, no. 11, 25 November 2008 (2008-11-25), pages 38 - 41 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103897678A (en) * | 2012-12-27 | 2014-07-02 | 中国石油化工股份有限公司 | Water-in-oil drilling fluid and preparation method thereof |
| 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 |
| CN112694412A (en) * | 2019-10-22 | 2021-04-23 | 中国石油化工股份有限公司 | Betaine and preparation method and application thereof |
| 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 |
| CN111013484A (en) * | 2019-11-25 | 2020-04-17 | 南京科技职业学院 | Alkyl glycoside carboxyl betaine type zwitterionic surfactant and preparation method thereof |
| CN115403750A (en) * | 2022-09-29 | 2022-11-29 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102276489B (en) | 2014-03-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102276822B (en) | Alkylphenol polyoxyethylene ether hydroxyl sulfonate type betaine and preparation method thereof | |
| CN102276489B (en) | Alkylphenol polyoxyethylene ether carboxylate type betaine and preparation method thereof | |
| CN102277146B (en) | Composition for improving recovery ratio substantially and preparation method thereof | |
| Ayirala et al. | A state-of-the-art review to develop injection-water-chemistry requirement guidelines for IOR/EOR projects | |
| WO2009058846A1 (en) | Systems and methods for producing oil and/or gas | |
| CN110325617B (en) | Surfactant for enhanced oil recovery | |
| CN102464598A (en) | Fatty acid amide polyoxylethylene ether benzene sulfonate and preparation method thereof | |
| CN104109519A (en) | Betaine-polymer oil displacement composition and preparation method thereof | |
| CN104559988B (en) | Beet alkali surface activator, preparation method and the application in intensified oil reduction | |
| CN102278102B (en) | Binary oil driving method for high-temperature and high-salt oil reservoir | |
| WO2015161812A1 (en) | Compounds, compositions thereof and methods for hydrocarbon extraction using the same | |
| CN102277147B (en) | Oil displacement method for high-temperature high-salt oil reservoir | |
| CN104559985B (en) | The displacement of reservoir oil is applied in poly- table pack object and its tertiary oil recovery | |
| CA3089899A1 (en) | Methods and compositions for diversion during enhanced oil recovery | |
| CN102277148B (en) | Composition for improving recovery ratio of crude oil and preparation method thereof | |
| CN105368430A (en) | Oil-displacing agent, preparing method of oil-displacing agent and intensified oil production method | |
| CN104277806A (en) | Oil displacement composition and preparation method and application thereof | |
| CN112707865B (en) | Zwitterionic surfactant and preparation method thereof | |
| CN105273704B (en) | Salt tolerant oil displacement surfactant and preparation method thereof | |
| CN113930226B (en) | Surfactant composition containing polyether quaternary ammonium salt and preparation method thereof and method for improving oil and gas yield | |
| CN103540306B (en) | Three adopt surfactant composition and preparation method thereof | |
| CN104559989A (en) | Hydrocarbyl amine polyoxyethylene ether polyoxypropylene ether sulfonate type betaine | |
| CN104559986B (en) | Binary is driven poly- table pack thing and its is applied in intensified oil reduction | |
| CN104559990B (en) | Chemical flooding surface activator composition and its application | |
| CN101280182B (en) | Surfactant composition and use thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |