CN102219897B - Disulfonate gemini surfactant with high temperature and salt resistance and preparation method thereof - Google Patents
Disulfonate gemini surfactant with high temperature and salt resistance and preparation method thereof Download PDFInfo
- Publication number
- CN102219897B CN102219897B CN201010147142A CN201010147142A CN102219897B CN 102219897 B CN102219897 B CN 102219897B CN 201010147142 A CN201010147142 A CN 201010147142A CN 201010147142 A CN201010147142 A CN 201010147142A CN 102219897 B CN102219897 B CN 102219897B
- Authority
- CN
- China
- Prior art keywords
- acyl group
- fatty acyl
- diamines
- neopentanoic
- carbochain
- 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
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a disulfonate gemini surfactant with high temperature and salt resistance and a preparation method thereof, mainly solving problems in the prior art that the oil driving agent containing the surfactant has poor oil displacement efficiency and high concentration of use under the condition of high temperature and salt, alkali takes the corrosion and the scale deposition to the ground floor and the oil well in ASP (alkali, surfactant and polymer) driving. The invention better solves the problems by taking the technical scheme, in which N,N-bisfatty acyl diamine dimethyl propanoic acid dipolyoxyethylene ether disulfonate with the molecular formula of FORMULA is adopted, wherein M is any one of metal ions of potassium, sodium and lithium, R1 is alkyl group of C9-C17, R2 is alkyl group of C2-C6, n is the addition number of ethoxy (EO) group and is any one integer of 2-7. The invention can be used in the production of tertiary oil recovery.
Description
Technical field
The present invention relates to a kind of resisting high temperature, high salt bissulfosalt double surface active agent and preparation method thereof, particularly about N, two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-and preparation method thereof.
Background technology
Chemical flooding is the main method of TOR, and surfactant flooding is considered to improve by a relatively large margin a kind of chemical agent of RF, applied widely, tool development prospect.No matter tensio-active agent is as host or as the auxiliary agent displacement of reservoir oil, all plays immeasurable effect to increasing substantially RF.
The dominant mechanism of using tensio-active agent can improve oil recovery factor is: after the oil field gets into high water-cut stage; Surplus oil with discontinuous oil film by trap in the hole of reservoir rocks; Two main power that act on the oil droplet are viscaps; If select suitable surfactant system for use, reduce the IT between profit, make the IT between the oil bearing reservoir profit reduce to lower or ultralow value (10 from 20～30mN/m
-3～10
-4MN/m), just can reduce the resistance that the oil droplet distortion was brought when surplus oil was moved, thereby significantly improve oil displacement efficiency.Surfactant flooding improves oil recovery factor and depends mainly on sweep efficiency and the oil displacement efficiency of tensio-active agent in oil reservoir.
Be Er=E υ Ed
In the formula: Er representes RF, %; E υ representes sweep efficiency, %; Ed representes oil displacement efficiency, %.
Therefore, improving Er must start with from improving Ev and Ed.Promoting agent (comprising tensio-active agent and alkali) can improve Ed (oil displacement efficiency) owing to have effects such as reducing oil water interfacial tension.This effect can be described by combined effect parameter hollow billet number (N):
Ed∝N
N=motivating force/viscous force ∝ μ υ/Y
Ow
In the formula: μ representes to inject phase viscosity; υ representes to inject the phase flow stream velocity; Y
OwIT between the expression profit.
Practice proves, reduce residual oil saturation effectively, must the hollow billet number be improved 3～4 one magnitude.Because oil reservoir IR and pressure are limited, it is not enough therefore depending merely on raising μ and υ, but can be with oil water interfacial tension Y
OwReduce by 3 or the higher order of magnitude, thereby improve the hollow billet number greatly and Ed (oil displacement efficiency) is significantly improved, this also is the main oil-displacement mechanism of promoting agent.And to improve sweep efficiency, and main way is the mobility that reduces displacing fluid, this point can realize through adding polymkeric substance increase displacing fluid viscosity.Adopt in the operation three; Utilization ASP ternary composite driving flooding system; The ultra low interfacial tension that can obtain between profit through the adding tensio-active agent increases the displacement of reservoir oil (Ed) rate of imitating; Inject fluid viscosity raising sweep efficiency (Ev) through injection of polymer to increase, inject alkali to reduce the absorption of tensio-active agent.Make full use of the useful synergistic combination effect of ASP, improve oil recovery factor (Er).
The tensio-active agent industrialization product of external used for tertiary oil recovery mainly contains two big types: the one, and sulfonated petro-leum is main tensio-active agent; The 2nd, sulfonated alkylbenzene is main tensio-active agent; These two types of tensio-active agent raw materials are all taken from crude oil; Raw material sources are wide, quantity is big, thereby also are the maximum tensio-active agents of external TOR consumption.Because sulfonate surfactant is anionic, it and the divalent cation (Ca in the local water
2+, Mg
2+Deng) can precipitate, work as Ca
2+, Mg
2+Just lose oil displacement efficiency when surpassing 300 μ g/g.For this reason, also continuing the suitable high saliferous of development research, high Ca abroad
2+, Mg
2+The tensio-active agent that the ion stratum is used comprises the research of multi-functional tensio-active agent, Gemini surface active agent and sacrifice agent, and pays attention to the composite research of various tensio-active agents.
Sulfonated petro-leum is real a large amount of tensio-active agent as oil-displacing agent, and this is because sulfonated petro-leum has the following advantages: 1. production technique is simple, and price is low; 2. derive from crude oil, it is strong to reduce the IT ability.But the sulfonated petro-leum salt tolerance is poor, and the absorption loss is bigger, and owing to reasons such as raw material is formed complicacy, and different batches product performance difference is big have limited its further broadened application.Therefore inapplicable for the high temperature and high salt oil deposit sulfonated petro-leum.
The anion-nonionic amphoterics is one of focus of TOR (EOR) area research in recent years always; Owing in its molecular structure two kinds of non-ionic groups of different nature and anionic group are designed in same surfactant molecule; Make it have the advantage of negatively charged ion and nonionogenic tenside concurrently; Therefore mutual supplement with each other's advantages, excellent property have shown good prospects for application, the binary combination flooding system that especially exists to alkali-free; Owing to do not have the existence of alkali not only to avoid the problems such as obstruction, fouling and corrosion of oil reservoir, and can form ultra low interfacial tension with crude oil.And Gemini surface active agent is to be connected base key with one and to be closed the special construction compound that forms by two hydrophilic radicals, two hydrophobic groupings, has more good performance than conventional surfactant.Gemini surface active agent have micelle-forming concentration low, reduce that the IT ability is strong, ability is than characteristics such as high salinity and particular rheological properties and visco-elasticity-viscosifying actions; Be that one type of raising RF that is rich in application prospect is used tensio-active agent, for new approach is opened up in the TOR in oil field.
In the patented claim at beginning of the thirties late 1920s, Degroot (De Groot) just once proposed the RF that the water soluble surfactant active helps to improve oil.
At present; The main Gemini surface active agent of domestic research and development mainly is the positively charged ion double quaternary ammonium salt type, has reported in succession that like Chinese patent CN 1528853, CN 1817431, CN 1066137 etc. the bisamide type is cationic, fluorine-containing cationic and contain the pyridyl cation Gemini surfactant.Shortcomings such as the absorption loss is big because positively charged ion has, cost height; The research and development of anionic and non-ionic type Gemini surface active agent have in recent years also obtained increasing attention, have reported the synthetic of the asymmetric Shuangzi of a kind of negatively charged ion like Chinese patent CN 101073757.And since aniorfic surfactant to have salt tolerance poor, and non-ionic type has the shortcoming of temperature tolerance difference, makes that these products can't being applied at high temperature and high salt oil deposit.
In addition, in the existing ternary composite oil-displacing system, contain the alkali of high density; Like sodium hydroxide, yellow soda ash etc., in use, to bringing huge injury in stratum and oil well etc.; Employed tensio-active agent is difficult for by biological degradation; And human body also there is certain hazardness, as: 1991, Zhao Guoxi was at " tensio-active agent physical chemistry " P495; 1994, disclosed content among Liu Chengzai " tensio-active agent the is complete works of " P35.So to those harsh oil reservoirs, we ought to seek a kind of under alkali-free, high temperature (FT is greater than 85 ℃), high salt (more than the salinity 40000mg/L) condition Stability Analysis of Structures, and can form 10 with crude oil
-3～10
-4The mN/m ultra low interfacial tension effectively improves the displacing surfactant system of oil recovery factor.Of the present invention this just under the alkali-free situation, be suitable for high temperature and high salt oil deposit the moon-non-Gemini surface active agent, its preparation method, binary is compound and the application in TOR.
Summary of the invention
One of technical problem to be solved by this invention is that the oil-displacing agent that contains tensio-active agent in the prior art exists under the high temperature and high salt condition oil displacement efficiency poor; The corrosion that alkali brings stratum and oil well in working concentration height and the ternary composite driving and the problem of incrustation injury; A kind of new double type N is provided, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-.Contain N, the surfactant compsn of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-still can form 10 with crude oil under alkali-free, high temperature and high salt condition
-3～10
-4Milli ox/rice ultra low interfacial tension improves the high temperature and high salt oil deposit RF.Two of technical problem to be solved by this invention provides one of a kind of and technical solution problem corresponding N, the preparation method of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-.
In order one of to solve the problems of the technologies described above, the technical scheme that the present invention adopts is following: a kind of N, and the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-, its general molecular formula is:
Wherein: R
1Be C
9～C
17Alkyl, R
2Be C
2～C
6Alkyl, n is the adduction number of ethoxy group EO, its span is any integer in 2～7; M is any one metals ion that is selected from potassium, sodium or the lithium.
In the technique scheme, the M preferred version is potassium and sodium, and more preferably scheme is for being selected from sodium; R
1It is to have best hydrophile-lipophile balance value, its water-soluble fluid power and crude oil formation 10 at 3～4 o'clock that carbon number adds ratio preferable range that 1 sum and EO count n
-3～10
-4Ultra low interfacial tension; N, the R in the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-
1Carbonatoms is preferably nine, 11,15 or 17, R
2Carbonatoms be preferably two, four or six.
For solve the problems of the technologies described above two, the technical scheme that the present invention adopted is following: a kind of N, the preparation method of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-may further comprise the steps:
(a) N, the preparation of the two fatty acyl group diamines neopentanoic acids of N-:
With the carbochain number of required proportioning is 10～18 lipid acid, thionyl chloride and N, and dinethylformamide (DMF) was 70～100 ℃ of reactions 2～5 hours, and excessive thionyl chloride is extracted in decompression out, and it is 10～18 fat acyl chloride that the transparent liquid that obtains is the carbochain number
1In addition be 2～6 diamines, TEB 3K and solvent 1 with the carbon number of required proportioning, after the 4-dioxane mixed, 40～70 ℃ of reactions 2～5 hours, unreacted raw material was removed in decompression and solvent gets the diamines dimethylated methyl propionate
2, regulate pH=9～10 with alkaline solution, drip under the vigorous stirring
1, in 40～70 ℃ of reactions 2～6 hours, getting N again, N-two carbochain numbers are 10～18 fatty acyl group diamines dimethylated methyl propionates
3, the ethanol of adding aequum is regulated pH=11～12 with alkaline solution, and back flow reaction 2～6 hours gets N after the acidifying, and the two carbochain numbers of N-are 10～18 fatty acyl group diamines neopentanoic acids; Wherein, preparation
1The time, the carbochain number is 10～18 lipid acid, thionyl chloride and N, the mol ratio of dinethylformamide is 1: 1.0～2.0: 0.03～0.1; Preparation
2The time, solvent is 1, and 4-dioxane, consumption are 3～6 times of 2～6 diamines quality for the carbochain number, and the carbochain number is that 2～6 the diamines and the mol ratio of TEB 3K are 1: 1.0～4.0; Preparation
3The time, the carbochain number is that the mol ratio that 10～18 fat acyl chloride and carbochain number are 2～6 diamines dimethylated methyl propionates is 1.9～2.5: 1; Preparation N, when the two carbochain numbers of N-were 10～18 fatty acyl group diamines neopentanoic acids, amount of ethanol was 5～10 times of 2～6 diamines quality for the carbochain number.
(b) N, the preparation of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ethers of N-:
Step (a) the synthetic N of institute; The two carbochain numbers of N-are that 10～18 fatty acyl group diamines neopentanoic acids and oxyethane are 85～160 ℃ by required proportioning in temperature of reaction; Pressure is less than under the 0.80MPa gauge pressure condition; The basic cpd of calcium is a catalyzer, react N, the two carbochain numbers of N-are 10～18 fatty acyl group diamines neopentanoic acids, two polyoxy Vinyl Ethers.Wherein, N, the two carbochain numbers of N-are that 10～18 fatty acyl group diamines neopentanoic acids and oxyethane mol ratio are 1: 4～14, and catalyst levels is N, and the two carbochain numbers of N-are 0.5～5.0% of 10～18 fatty acyl group diamines neopentanoic acid quality.
(c) N, the preparation of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-:
With step (b) the synthetic N of institute; The two carbochain numbers of N-are that 10～18 fatty acyl group diamines neopentanoic acids, two polyoxy Vinyl Ethers are by required proportioning and 3-chloro-2-hydroxypropionate sodium, Pottasium Hydroxide or sodium hydroxide and Tetrabutyl amonium bromide catalyst mix; With toluene is solvent, 50～130 ℃ of temperature of reaction, reacts 3～15 hours; Reaction finishes after aftertreatment gets N, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-.Wherein, N, the two carbochain numbers of N-are mol ratio=1: 2～6: 2～8: 0.05～0.3 of 10～18 fatty acyl group diamines neopentanoic acids, two polyoxy Vinyl Ethers, 3-chloro-2-hydroxypropionate sodium, Pottasium Hydroxide or sodium hydroxide and Tetrabutyl amonium bromide.
In the technique scheme, (a) prepare in the step
1The time, the carbochain number is 10～18 lipid acid, thionyl chloride and N, the mol ratio of dinethylformamide is preferably 1: 1.2～and 2.0: 0.05～0.1; Preparation
2The time solvent be 1; It is 4～5 times of 2～6 diamines quality that 4-dioxane, consumption are preferably the carbochain number, the carbochain number be the mol ratio of 2～6 diamines and TEB 3K be preferably 1: 2.2～3.0; Temperature of reaction is preferably 50～60 ℃, and the reaction times is preferably 3～4 hours; Preparation
3The time, the carbochain number is that the mol ratio that 10～18 fat acyl chloride and carbochain number are 2～6 diamines dimethylated methyl propionates is preferably 2.0～2.2: 1, and temperature of reaction is preferably 60～70 ℃, and the reaction times is preferably 3～4 hours; Preparation N, when the two carbochain numbers of N-were 10～18 fatty acyl group diamines neopentanoic acids, it was 6～8 times of 2～6 diamines quality that amount of ethanol is preferably the carbochain number, the reaction times is preferably 3～5 hours.(b) N, the two carbochain numbers of N-be 10～18 fatty acyl group diamines neopentanoic acids and oxyethane mol ratio be preferably 1: 6～12, catalyst levels is preferably N, N-pair of carbochain numbers are 1.0～3.0% of 10～18 fatty acyl group diamines neopentanoic acid quality.(c) N in the step; The two carbochain numbers of N-be the mol ratio of 10～18 fatty acyl group diamines neopentanoic acids, two polyoxy Vinyl Ethers, 3-chloro-2-hydroxypropionate sodium, sodium hydroxide (Pottasium Hydroxide) and Tetrabutyl amonium bromide be preferably 1: 2.5～5.5: 3～7: 0.1～0.2; Temperature of reaction is preferably 70～110 ℃, and the reaction times is preferably 5～12 hours.
The N of the present invention's preparation; The two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-; Owing to contain aerobic ethene non-ionic group and azochlorosulfonate acid anion group simultaneously in its molecular structure; Make the salt tolerant advantage of its heat resistance that has AS concurrently and nonionogenic tenside; And symmetric Shuangzi constitutional features, make again its have micelle-forming concentration low, reduce strong, anti-high salinity of IT ability and characteristics such as particular rheological properties and visco-elasticity-viscosifying action, have more good performance than conventional surfactant.Do not contain aromatic ring structure in its molecule in addition, be easier to biological degradation, therefore less to the harm of human body and environment, be a kind of green surfactant that is suitable for the used for tertiary oil recovery of high temperature and high salt oil deposit.
Adopt the N of the present invention's preparation; The two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-; With consumption is that the temperature resistant antisalt polymkeric substance of 0.1～0.3wt% and 0.1～0.2wt% (forms with acrylic amide, 2-acrylamido-2-methyl propane sulfonic acid, 2-acrylamido dodecyl sodium sulfonate and four kinds of monomer copolymerizations of allyl group oleyl ether; Its molar percentage is 76: 18: 5: 1) form the displacement of reservoir oil and use compsn; Under the alkali-free condition, can be used for FT and be 85 ℃, salinity 16000～32000 mg/litre, Ca
2+, Mg
2+The Shengli Oil Field that is 450～890 mg/litre wins Tuo Er district's local water and crude oil, has measured this oil-displacing agent aqueous solution and Shengli Oil Field and has won the dynamic interface tension value between the Tuo Er district crude oil, can reach 10
-3～10
-4The ultra low interfacial tension of mN/m; Can on the water drive basis, can reach 16.5% by (water drive improves oil recovery factor and reaches 40.9%) raising oil recovery factor through the indoor evaluation of physical simulation displacement test at this oil-displacing agent on high temperature, the high salinity reservoir, obtain better technical effect.
Description of drawings
Fig. 1 is N, the infrared spectrogram of the two fatty acyl group diamines neopentanoic acids of N-.
Fig. 2 is N, the infrared spectrum of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ethers of N-.
Fig. 3 is N, the infrared spectrum of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-.
The N of the present invention's preparation; The two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-and each midbody can characterize through following method: after synthetics is purified; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), confirm the chemical structure of sample, to reach IR Characterization to compound according to the invention.
Can be known by Fig. 1, be 2850～2950cm in wave number
-1Methyl and the flexible characteristic peak of methylene radical C-H on the alkyl chain, 1475cm appear in the place
-1C-H flexural vibration on the alkyl chain, 3129cm
-1～3613cm
-1Wide bag appears in the place, explain that the H of the N-H in the secondary amide is substituted, and replace on the resultant-OH among the COOH is flexible and form the residuary water of acid increase, thus formed the wide bag here, 1634cm
-1The acid amides I key band vC=O peak at place broadens and at 1710cm
-1An acromion can be seen by the place, and this is the vC=O on the COOH, and proved response has generated N really thus, the two fatty acyl group diamines neopentanoic acids of N-.
Fig. 2 comparison diagram 1 has increased 1106cm
-1Locate a broad peak, this peak is that the last C-O-C asymmetric stretch of EO bands of a spectrum cause owing to connected EO, because this peak is very wide, and original 1058cm
-1The peak at place is capped, because the viscosity of sample increases, all peaks are broadening to some extent all, and proved response has generated N really thus, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ethers of N-.
Comparison diagram 3 and Fig. 2 can find from Fig. 2 to Fig. 3 1106cm
-1About the obvious broadening in peak located, and wave number moves on to 1117cm
-1The place, 1350cm
-1About also broadening and obviously growing tall to some extent of peak, the characteristic peak of sulphonate, the symmetrical stretching vibration of S=O is at 1155cm
-1About, antisymmetric stretching vibration is at 1345cm
-1About, so 1117cm
-1The peak at place is owing to C-O-C asymmetric stretch bands of a spectrum stack on the symmetrical stretching vibration of S=O and the EO causes 1350cm
-1About the peak be that vibration causes because the antisymmetric stretching vibration of S=O is with skeleton carbon, proved response has generated N really thus, N-pair of fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates.
Through embodiment the present invention is done further elaboration below.
Embodiment
[embodiment 1]
(a) N, the two lauroyl quadrol neopentanoic acids of N-synthetic
With LAURIC ACID 99 MIN 300 grams (1.5 moles), sulfur oxychloride 267.8 grams (2.25 moles) and 4.5 gram DMF; Add and be furnished with in 1000 milliliters of four-hole boiling flasks of sealing machine stirring, TM, prolong etc.; After 3 hours, decompression steams excessive thionyl chloride, obtains lauroyl chloride in 90 ℃ of reactions.Another is furnished with and adds anhydrous ethylenediamine 45.0 grams (0.75 mole), 180 grams 1 in 2000 milliliters of four-hole boiling flasks of sealing machine stirring, TM, prolong; The 4-dioxane is warming up to 50 ℃, slowly drips TEB 3K 165.0 grams (1.65 moles); Drip off and continue reaction 3 hours; Unreacted TEB 3K and solvent 1 are removed in decompression, and 4-dioxane, residuum are the quadrol dimethylated methyl propionate.With 50wt% sodium hydroxide conditioned reaction liquid pH=8～10, slowly drip lauroyl chloride under the vigorous stirring, constantly add simultaneously 50wt% sodium hydroxide with the pH that keeps reaction 8～10, drip off the back and continue reaction 3 hours in 60 ℃; Get N, the two lauroyl quadrol dimethylated methyl propionates of N-continue in reaction flask, to add 270 gram ethanol, again with 50wt% sodium hydroxide accent pH=11～12; Refluxed 4 hours, cooling, filtration is desalted; Pressure reducing and steaming ethanol, residuum is neutralized to strongly-acid with hydrochloric acid, branch vibration layer; Get N, two lauroyl quadrol neopentanoic acids 306.2 grams of N-, molar yield 68.5%.
(b) N, the two lauroyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=4) of N-synthetic
With step (a) synthetic N; The basic cpd of two lauroyl quadrol neopentanoic acid 306.2 grams (0.514 mole) of N-, 3.4 gram calcium adds to be furnished with in the high-pressure reactor of condensing works, whipping appts and gas distributor; When limit logical nitrogen limit heating is made 135 ℃; Add 20 gram water, stirring reaction 1 hour.After removing moisture content, be cooled to 80 ℃, the sulfuric acid (20wt%) that slowly drips the catalyst neutralisation theoretical amount makes the compound oxidizing calcium alkoxylating catalyst reaction solution system of high reactivity, highly selective; System temperature is heated to 80～90 ℃; The open vacuum system, dehydration is 2 hours under high vacuum, uses nitrogen purging then 3～4 times; The system temperature of reaction is transferred to 140 ℃ slowly feed 181.1 gram (4.116 moles) oxyethane, control pressure≤0.60MPa.Reaction is used the nitrogen purging system after finishing, and cooling post neutralization, dehydration get N, the two lauroyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=4) of N-428.3 grams, molar yield 87.9%.
(c) N, two lauroyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=4) disulfonates of N-synthetic
With step (b) the synthetic N of institute; The two lauroyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=4) of N-428.3 grams (0.452 mole) and 152.3 gram (2.72 moles) Pottasium Hydroxide, 355.4 gram (1.81 moles) 3-chloro-2-hydroxypropionate sodiums, 16.3 gram Tetrabutyl amonium bromides, 1500 milliliters of toluene are mixed in to be furnished with mechanical stirring, in 5000 milliliters the reaction kettle of TM and reflux condensing tube, to be heated to 90 ℃ of reactions 8 hours.Cooling, neutralization divides and to remove inorganic salt, alkalize N, two lauroyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=4) disulfonates of N-, molar yield 75.8%.
To [embodiment 1] synthetic N; Two lauroyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=4) disulfonate and each midbody of N-; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), have all charateristic avsorption bands in Fig. 1～3.
[embodiment 2]
(a) N, the two lauroyl hexanediamine neopentanoic acids of N-synthetic
With [embodiment 1] (a), difference substitutes 45.0 gram (0.75 mole) anhydrous ethylenediamines with the anhydrous hexanediamine of 87.0 grams (0.75 mole), and all the other are identical, get N, two lauroyl hexanediamine neopentanoic acid 328.6 grams of N-, molar yield 67.2%.
(b) N, the two lauroyl hexanediamine neopentanoic acid two polyoxy Vinyl Ethers (n=3) of N-synthetic
With [embodiment 1] (b); Difference is with the N of 328.6 grams (0.504 mole), and the two lauroyl hexanediamine neopentanoic acids of N-substitute 306.2 gram (0.514 mole) N, and the usage quantity of the two lauroyl quadrol neopentanoic acids of N-, oxyethane is 133.1g (3.024 moles); The usage quantity of the basic cpd of calcium is 7.5 grams; Get N, the two lauroyl hexanediamine neopentanoic acid two polyoxy Vinyl Ethers (n=3) of N-409.5 grams, molar yield 88.2%.
(c) N, two lauroyl hexanediamine neopentanoic acid two polyoxy Vinyl Ether (n=3) disulfonates of N-synthetic
With step (b) the synthetic N of institute; The two lauroyl hexanediamine neopentanoic acid two polyoxy Vinyl Ethers (n=3) of N-409.5 grams (0.447 mole) and 100.5 gram (1.79 moles) Pottasium Hydroxide, 377.3 gram (1.92 moles) 3-chloro-2-hydroxypropionate sodiums, 16.3 gram Tetrabutyl amonium bromides, 1500 milliliters of toluene are mixed in to be furnished with mechanical stirring, in 5000 milliliters the reaction kettle of TM and reflux condensing tube, to be heated to 100 ℃ of reactions 6 hours.Cooling, neutralization divides and to remove inorganic salt, alkalize N, two lauroyl hexanediamine neopentanoic acid two polyoxy Vinyl Ether (n=3) disulfonates of N-, molar yield 75.5%.
To [embodiment 2] synthetic N; Two lauroyl hexanediamine neopentanoic acid two polyoxy Vinyl Ether (n=3) disulfonate and each midbody of N-; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), have all charateristic avsorption bands in Fig. 1～3.
[embodiment 3]
(a) N, the two ten acyl group tetramethylenediamine neopentanoic acids of N-synthetic
With [embodiment 1] (a); Difference substitutes 300.0 gram (1.5 moles) LAURIC ACID 99 MIN with the capric acid of 261.0 grams (1.5 moles); Anhydrous tetramethylenediamine with 66.0 grams (0.75 mole) substitutes 45.0 gram (0.75 mole) anhydrous ethylenediamines, and all the other are identical, get N; The two ten acyl group tetramethylenediamine neopentanoic acids of N-283.3 grams, molar yield 66.5%.
(b) N, two ten acyl group tetramethylenediamine neopentanoic acids, the two polyoxy Vinyl Ethers (n=3) of N-synthetic
With [embodiment 1] (b); Difference is with the N of 283.3 grams (0.499 mole), and the two ten acyl group tetramethylenediamine neopentanoic acids of N-substitute 306.2 gram (0.514 mole) N, and the usage quantity of the two lauroyl quadrol neopentanoic acids of N-, oxyethane is 131.7g (2.994 moles); The usage quantity of the basic cpd of calcium is 6.4 grams; Get N, the two ten acyl group tetramethylenediamine neopentanoic acids of N-two polyoxy Vinyl Ethers (n=3) 371.6 grams, molar yield 89.5%.
(c) N, two ten acyl group tetramethylenediamine neopentanoic acids, two polyoxy Vinyl Ether (n=3) disulfonates of N-synthetic
With step (b) the synthetic N of institute; The two ten acyl group tetramethylenediamine neopentanoic acids of N-two polyoxy Vinyl Ethers (n=3) 371.6 grams (0.447 mole) and 100.3 gram (1.79 moles) Pottasium Hydroxide, 263.3 gram (1.34 moles) 3-chloro-2-hydroxypropionate sodiums, 18.8 gram Tetrabutyl amonium bromides, 1500 milliliters of toluene are mixed in to be furnished with mechanical stirring, in 5000 milliliters the reaction kettle of TM and reflux condensing tube, to be heated to 80 ℃ of reactions 8 hours.Cooling, neutralization divides and to remove inorganic salt, alkalize N, two ten acyl group tetramethylenediamine neopentanoic acids, two polyoxy Vinyl Ether (n=3) disulfonates of N-, molar yield 73.5%.
To [embodiment 3] synthetic N; Two ten acyl group tetramethylenediamine neopentanoic acids, two polyoxy Vinyl Ether (n=3) disulfonate and each midbody of N-; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), have all charateristic avsorption bands in Fig. 1～3.
[embodiment 4]
(a) N, the two palmitoyl quadrol neopentanoic acids of N-synthetic
With palmitinic acid 422.4 grams (1.65 moles), sulfur oxychloride 235.6 grams (1.875 moles) and 6.3 gram DMF; Add and be furnished with in 1000 milliliters of four-hole boiling flasks of sealing machine stirring, TM, prolong etc.; After 5 hours, decompression steams excessive thionyl chloride, obtains palmityl chloride in 80 ℃ of reactions.Another is furnished with and adds anhydrous ethylenediamine 45.0 grams (0.75 mole), 225 grams 1 in 2000 milliliters of four-hole boiling flasks of sealing machine stirring, TM, prolong; The 4-dioxane is warming up to 60 ℃, slowly drips TEB 3K 187.5 grams (1.875 moles); Drip off and continue reaction 4 hours; Unreacted TEB 3K and solvent 1 are removed in decompression, and 4-dioxane, residuum are the quadrol dimethylated methyl propionate.With 50wt% sodium hydroxide conditioned reaction liquid pH=8～10, slowly drip lauroyl chloride under the vigorous stirring, constantly add simultaneously 50wt% sodium hydroxide with the pH that keeps reaction 8～10, drip off the back and continue reaction 4 hours in 70 ℃; Get N, the two palmitoyl quadrol dimethylated methyl propionates of N-continue in reaction flask, to add 360 gram ethanol, again with 50wt% sodium hydroxide accent pH=11～12; Refluxed 4 hours, cooling, filtration is desalted; Pressure reducing and steaming ethanol, residuum is neutralized to strongly-acid with hydrochloric acid, branch vibration layer; Get N, two palmitoyl quadrol neopentanoic acids 360.0 grams of N-, molar yield 67.8%.
(b) N, the two palmitoyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=5) of N-synthetic
With [embodiment 1] (b); Difference is with the N of 360.0 grams (0.508 mole), and the two palmitoyl quadrol neopentanoic acids of N-substitute 306.2 gram (0.514 mole) N, and the usage quantity of the two lauroyl quadrol neopentanoic acids of N-, oxyethane is 223.5g (5.08 moles); The usage quantity of the basic cpd of calcium is 6.6 grams; Get N, the two palmitoyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=5) of N-497.4 grams, molar yield 85.3%.
(c) N, two palmitoyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=5) disulfonates of N-synthetic
With step (b) the synthetic N of institute; The two palmitoyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=5) of N-497.4 grams (0.433 mole) and 103.6 gram (2.60 moles) sodium hydroxide, 339.9 gram (1.73 moles) 3-chloro-2-hydroxypropionate sodiums, 17.3 gram Tetrabutyl amonium bromides, 1500 milliliters of toluene are mixed in to be furnished with mechanical stirring, in 5000 milliliters the reaction kettle of TM and reflux condensing tube, to be heated to 100 ℃ of reactions 8 hours.Cooling, neutralization divides and to remove inorganic salt, alkalize N, two palmitoyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=5) disulfonates of N-, molar yield 72.9%.
To [embodiment 4] synthetic N; Two palmitoyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=5) disulfonate and each midbody of N-; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), have all charateristic avsorption bands in Fig. 1～3.
[embodiment 5]
(a) N, the two palmitoyl tetramethylenediamine neopentanoic acids of N-synthetic
With [embodiment 4] (a), difference substitutes 45.0 gram (0.75 mole) anhydrous ethylenediamines with the anhydrous tetramethylenediamine of 66.0 grams (0.75 mole), and all the other are identical, get N, two palmitoyl tetramethylenediamine neopentanoic acid 362.7 grams of N-, molar yield 65.7%.
(b) N, the two palmitoyl tetramethylenediamine neopentanoic acid two polyoxy Vinyl Ethers (n=4) of N-synthetic
With [embodiment 1] (b); Difference is with the N of 362.7 grams (0.493 mole), and the two palmitoyl tetramethylenediamine neopentanoic acids of N-substitute 306.2 gram (0.514 mole) N, and the usage quantity of the two lauroyl quadrol neopentanoic acids of N-, oxyethane is 173.5g (3.944 moles); The usage quantity of the basic cpd of calcium is 7.4 grams; Get N, the two palmitoyl tetramethylenediamine neopentanoic acid two polyoxy Vinyl Ethers (n=4) of N-456.5 grams, molar yield 85.1%.
(c) N, two palmitoyl tetramethylenediamine neopentanoic acid two polyoxy Vinyl Ether (n=4) disulfonates of N-synthetic
With step (b) the synthetic N of institute; The two palmitoyl tetramethylenediamine neopentanoic acid two polyoxy Vinyl Ethers (n=4) of N-456.5 grams (0.420 mole) and 102.9 gram (2.57 moles) sodium hydroxide, 290.5 gram (1.48 moles) 3-chloro-2-hydroxypropionate sodiums, 19.9 gram Tetrabutyl amonium bromides, 1600 milliliters of toluene are mixed in to be furnished with mechanical stirring, in 5000 milliliters the reaction kettle of TM and reflux condensing tube, to be heated to 100 ℃ of reactions 10 hours.Cooling, neutralization divides and to remove inorganic salt, alkalize N, two palmitoyl tetramethylenediamine neopentanoic acid two polyoxy Vinyl Ether (n=4) disulfonates of N-, molar yield 71.1%.
To [embodiment 5] synthetic N; Two palmitoyl tetramethylenediamine neopentanoic acid two polyoxy Vinyl Ether (n=4) disulfonate and each midbody of N-; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), have all charateristic avsorption bands in Fig. 1～3.
[embodiment 6]
(a) N, the two stearoyl quadrol neopentanoic acids of N-synthetic
With Triple Pressed Stearic Acid 497 grams (1.75 moles), sulfur oxychloride 374.9 grams (3.15 moles) and 7.5 gram DMF; Add and be furnished with in 1000 milliliters of four-hole boiling flasks of sealing machine stirring, TM, prolong etc.; After 3 hours, decompression steams excessive thionyl chloride, obtains stearyl chloride in 95 ℃ of reactions.Another is furnished with and adds anhydrous ethylenediamine 45.0 grams (0.75 mole), 225 grams 1 in 2000 milliliters of four-hole boiling flasks of sealing machine stirring, TM, prolong; The 4-dioxane is warming up to 60 ℃, slowly drips TEB 3K 225.0 grams (2.25 moles); Drip off and continue reaction 4 hours; Unreacted TEB 3K and solvent 1 are removed in decompression, and 4-dioxane, residuum are the quadrol dimethylated methyl propionate.With 50wt% sodium hydroxide conditioned reaction liquid pH=8～10, slowly drip lauroyl chloride under the vigorous stirring, constantly add simultaneously 50wt% sodium hydroxide with the pH that keeps reaction 8～10, drip off the back and continue reaction 3 hours in 70 ℃; Get N, the two stearoyl quadrol dimethylated methyl propionates of N-continue in reaction flask, to add 315 gram ethanol, again with 50wt% sodium hydroxide accent pH=11～12; Refluxed 4 hours, cooling, filtration is desalted; Pressure reducing and steaming ethanol, residuum is neutralized to strongly-acid with hydrochloric acid, branch vibration layer; Get N, two stearoyl quadrol neopentanoic acids 384.5 grams of N-, molar yield 67.1%.
(b) N, the two stearoyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=6) of N-synthetic
With [embodiment 1] (b); Difference is with the N of 384.5 grams (0.503 mole), and the two stearoyl quadrol neopentanoic acids of N-substitute 306.2 gram (0.514 mole) N, and the usage quantity of the two lauroyl quadrol neopentanoic acids of N-, oxyethane is 265.6g (6.036 moles); The usage quantity of the basic cpd of calcium is 5.6 grams; Get N, the two stearoyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=6) of N-547.2 grams, molar yield 84.2%.
(c) N, two stearoyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=6) disulfonates of N-synthetic
With step (b) the synthetic N of institute; The two stearoyl quadrol neopentanoic acid two polyoxy Vinyl Ethers (n=6) of N-547.2 grams (0.424 mole) and 101.6 gram (2.54 moles) sodium hydroxide, 416.7 gram (2.12 moles) 3-chloro-2-hydroxypropionate sodiums, 26.9 gram Tetrabutyl amonium bromides, 1800 milliliters of toluene are mixed in to be furnished with mechanical stirring, in 5000 milliliters the reaction kettle of TM and reflux condensing tube, to be heated to 110 ℃ of reactions 12 hours.Cooling, neutralization divides and to remove inorganic salt, alkalize N, two stearoyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=6) disulfonates of N-, molar yield 72.3%.
To [embodiment 6] synthetic N; Two stearoyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=6) disulfonate and each midbody of N-; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), have all charateristic avsorption bands in Fig. 1～3.
[embodiment 7]
(a) N, the two stearoyl hexanediamine neopentanoic acids of N-synthetic
With [embodiment 6] (a), difference substitutes anhydrous ethylenediamine 45.0 grams (0.75 mole) with the anhydrous hexanediamine of 87.0 grams (0.75 mole), and all the other are identical, get N, two stearoyl hexanediamine neopentanoic acid 398.5 grams of N-, molar yield 64.8%.
(b) N, the two stearoyl hexanediamine neopentanoic acid two polyoxy Vinyl Ethers (n=5) of N-synthetic
With [embodiment 1] (b); Difference is with the N of 398.5 grams (0.486 mole), and the two stearoyl hexanediamine neopentanoic acids of N-substitute 306.2 gram (0.514 mole) N, and the usage quantity of the two lauroyl quadrol neopentanoic acids of N-, oxyethane is 213.8g (4.86 moles); The usage quantity of the basic cpd of calcium is 6.0 grams; Get N, the two stearoyl hexanediamine neopentanoic acid two polyoxy Vinyl Ethers (n=5) of N-507.6 grams, molar yield 82.9%.
(c) N, two stearoyl hexanediamine neopentanoic acid two polyoxy Vinyl Ether (n=5) disulfonates of N-synthetic
With step (b) the synthetic N of institute; The two stearoyl hexanediamine neopentanoic acid two polyoxy Vinyl Ethers (n=5) of N-507.6 grams (0.403 mole) and 159.6 gram (2.80 moles) Pottasium Hydroxide, 392.5 gram (2.00 moles) 3-chloro-2-hydroxypropionate sodiums, 26.1 gram Tetrabutyl amonium bromides, 1800 milliliters of toluene are mixed in to be furnished with mechanical stirring, in 5000 milliliters the reaction kettle of TM and reflux condensing tube, to be heated to 110 ℃ of reactions 12 hours.Cooling, neutralization divides and to remove inorganic salt, alkalize N, two stearoyl hexanediamine neopentanoic acid two polyoxy Vinyl Ether (n=5) disulfonates of N-, molar yield 70.6%.
To [embodiment 7] synthetic N; Two stearoyl hexanediamine neopentanoic acid two polyoxy Vinyl Ether (n=5) disulfonate and each midbody of N-; Use U.S. Nicolet-380FT-IR spectrograph, adopt liquid-film method or pellet technique to carry out IR spectroscopy (sweep limit 4000～400cm
-1), have all charateristic avsorption bands in Fig. 1～3.
[embodiment 8～14]
With [embodiment 1～7] synthetic N; The two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-; With consumption is that the temperature resistant antisalt polymkeric substance of 0.1～0.3wt% and 0.1～0.2wt% (forms with acrylic amide, 2-acrylamido-2-methyl propane sulfonic acid, 2-acrylamido dodecyl sodium sulfonate and four kinds of monomer copolymerizations of allyl group oleyl ether; Its molar percentage is 76: 18: 5: 1) form displacement of reservoir oil compsn, at FT greater than 85 ℃, salinity 16000～32000 mg/litre, Ca
2+, Mg
2+The Shengli Oil Field that is 450～890 mg/litre wins Tuo Er district's local water and crude oil, has measured this oil-displacing agent aqueous solution and Shengli Oil Field and has won the dynamic interface tension value between the Tuo Er district crude oil, can reach 10
-3～10
-4The ultra low interfacial tension of mN/m; In length is 30 centimetres; Diameter is 2.5 centimetres; Rate of permeation is to carry out the physical simulation displacement test on 1.5 micron 2 the rock core; Indoor evaluation can reach 14.3～16.5% by (water drive can improve oil recovery factor 39.8～40.9%) raising oil recovery factor at this oil-displacing agent on high temperature, the high salinity reservoir on the water drive basis, the result sees shown in the table 1.IT is dripped interfacial tensimeter mensuration by the TX500 type rotation that Texas ,Usa university produces.
[comparative example 1]
With [embodiment 8]; Difference substitutes 0.15wt%N with the petroleum sodium sulfonate (Wuxi refinery) of 0.15wt%; Two lauroyl quadrol neopentanoic acid two polyoxy Vinyl Ether (n=4) disulfonates of N-, all the other are identical, and the dynamic interface tension value of having measured between this oil-displacing agent aqueous solution and the Shengli Oil Field victory Tuo Er district crude oil reaches 0.0712mN/m; Through the indoor evaluation of physical simulation displacement test; Record water drive and can improve oil recovery factor 40.2%, this displacement of reservoir oil compsn can improve oil recovery factor 10.3% again on the water drive basis, and the result sees shown in the table 1.IT is dripped interfacial tensimeter mensuration by the TX500 type rotation that Texas ,Usa university produces.
[comparative example 2]
With [embodiment 8]; Difference substitutes the above-mentioned temperature resistant antisalt polymkeric substance of 0.15wt% with the super high molecular weight polyacrylamide (viscosity-average molecular weight is 2,500 ten thousand) of 0.15wt%; All the other are identical; The dynamic interface tension value of having measured between this oil-displacing agent aqueous solution and the Shengli Oil Field victory Tuo Er district crude oil reaches 0.0459mN/m, through the indoor evaluation of physical simulation displacement test, records water drive and can improve oil recovery factor 40.3%; This displacement of reservoir oil compsn can improve oil recovery factor 9.1% again on the water drive basis, the result sees shown in the table 1.IT is dripped interfacial tensimeter mensuration by the TX500 type rotation that Texas ,Usa university produces.
Claims (5)
1. N, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-, its general molecular formula is:
Wherein: R
1Be C
9～C
17Alkyl, R
2Be C
2～C
6Alkyl, n is the adduction number of ethoxy group EO, its span is any integer in 2～7; M is any one metals ion that is selected from potassium, sodium or the lithium.
2. according to the said N of claim 1, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-is characterized in that described R
1Carbonatoms be nine, 11,13,15 or 17.
3. according to the said N of claim 1, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-is characterized in that described R
2Carbonatoms be two, four or six.
4. N according to claim 1, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-is characterized in that described R
1Carbon number adds 1 sum, and the ratio that EO counts n is between 2～4.
5. the described N of claim 1, the preparation method of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-may further comprise the steps:
(a) N, the preparation of the two fatty acyl group diamines neopentanoic acids of N-:
With the carbochain number of required proportioning is 10～18 lipid acid, thionyl chloride and N, and dinethylformamide (DMF) was 70～100 ℃ of reactions 2～5 hours, and excessive thionyl chloride is extracted in decompression out, and it is 10～18 fat acyl chloride that the transparent liquid that obtains is the carbochain number
1In addition be 2～6 diamines, TEB 3K and solvent 1 with the carbon number of required proportioning, after the 4-dioxane mixed, 40～70 ℃ of reactions 2～5 hours, unreacted raw material was removed in decompression and solvent gets the diamines dimethylated methyl propionate
2, regulate pH=9～10 with alkaline solution, drip under the vigorous stirring
1, in 40～70 ℃ of reactions 2～6 hours, getting N again, the two carbochain numbers of N-are 10～18 fatty acyl group diamines dimethylated methyl propionates
3, the ethanol of adding aequum is regulated pH=11～12 with alkaline solution, and back flow reaction 2～6 hours gets N after the acidifying, and the two carbochain numbers of N-are 10～18 fatty acyl group diamines neopentanoic acids; Wherein, preparation
1The time, the carbochain number is 10～18 lipid acid, thionyl chloride and N, the mol ratio of dinethylformamide is 1: 1.0～2.0: 0.03～0.1; Preparation
2The time, solvent is 1, and 4-dioxane, consumption are 3～6 times of 2～6 diamines quality for the carbochain number, and the carbochain number is that 2～6 the diamines and the mol ratio of TEB 3K are 1: 1.0～4.0; Preparation
3The time, the carbochain number is that the mol ratio that 10～18 fat acyl chloride and carbochain number are 2～6 diamines dimethylated methyl propionates is 1.9～2.5: 1; Preparation N, when the two carbochain numbers of N-were 10～18 fatty acyl group diamines neopentanoic acids, amount of ethanol was 5～10 times of 2～6 diamines quality for the carbochain number;
(b) N, the preparation of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ethers of N-:
Step (a) the synthetic N of institute; The two carbochain numbers of N-are that 10～18 fatty acyl group diamines neopentanoic acids and oxyethane are 85～160 ℃ by required proportioning in temperature of reaction; Pressure is less than under the 0.80MPa gauge pressure condition; The basic cpd of calcium is a catalyzer, react N, the two carbochain numbers of N-are 10～18 fatty acyl group diamines neopentanoic acids, two polyoxy Vinyl Ethers; Wherein, N, the two carbochain numbers of N-are that 10～18 fatty acyl group diamines neopentanoic acids and oxyethane mol ratio are 1: 4～14, and catalyst levels is N, and the two carbochain numbers of N-are 0.5～5.0% of 10～18 fatty acyl group diamines neopentanoic acid quality;
(c) N, the preparation of the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-:
With step (b) the synthetic N of institute; The two carbochain numbers of N-are that 10～18 fatty acyl group diamines neopentanoic acids, two polyoxy Vinyl Ethers are by required proportioning and 3-chloro-2-hydroxypropionate sodium, Pottasium Hydroxide or sodium hydroxide and Tetrabutyl amonium bromide catalyst mix; With toluene is solvent, 50～130 ℃ of temperature of reaction, reacts 3～15 hours; Reaction finishes after aftertreatment gets N, the two fatty acyl group diamines neopentanoic acid two polyoxy Vinyl Ether disulfonates of N-; Wherein, N, the two carbochain numbers of N-are mol ratio=1: 2～6: 2～8: 0.05～0.3 of 10～18 fatty acyl group diamines neopentanoic acids, two polyoxy Vinyl Ethers, 3-chloro-2-hydroxypropionate sodium, Pottasium Hydroxide or sodium hydroxide and Tetrabutyl amonium bromide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010147142A CN102219897B (en) | 2010-04-15 | 2010-04-15 | Disulfonate gemini surfactant with high temperature and salt resistance and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010147142A CN102219897B (en) | 2010-04-15 | 2010-04-15 | Disulfonate gemini surfactant with high temperature and salt resistance and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102219897A CN102219897A (en) | 2011-10-19 |
| CN102219897B true CN102219897B (en) | 2012-10-10 |
Family
ID=44776619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201010147142A Active CN102219897B (en) | 2010-04-15 | 2010-04-15 | Disulfonate gemini surfactant with high temperature and salt resistance and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102219897B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102277146B (en) * | 2010-06-11 | 2013-12-25 | 中国石油化工股份有限公司 | Composition for improving recovery ratio substantially and preparation method thereof |
| CN102698648A (en) * | 2012-06-27 | 2012-10-03 | 东北石油大学 | Dendritic sulfonate-type tetramer surfactant and preparation method thereof |
| CN111763153B (en) * | 2019-04-02 | 2022-08-30 | 中国石油天然气股份有限公司 | Dodecyl polyoxyethylene ether sodium sulfate-diglucoside peptide compound and composite oil displacement agent |
| CN115702228B (en) * | 2020-04-24 | 2024-06-07 | 雪佛龙美国公司 | Polyanionic surfactants and methods of making and using the same |
| MX2022013113A (en) * | 2020-04-24 | 2023-01-16 | Chevron Usa Inc | Polyanionic surfactants and methods of making and using thereof. |
| MX2022013179A (en) * | 2020-04-24 | 2023-01-11 | Chevron Usa Inc | Polyanionic surfactants and methods of making and using thereof. |
| CN115916924A (en) * | 2020-04-24 | 2023-04-04 | 雪佛龙美国公司 | Polyanionic surfactants and methods of making and using the same |
| CN111559970B (en) * | 2020-05-28 | 2021-10-01 | 陕西科技大学 | Surface wetting agent with polysulfonic acid structure and preparation method thereof |
| CN113083152B (en) * | 2021-04-20 | 2022-02-08 | 山东大学 | Carboxylic acid sulfonic acid type surfactant, and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101029224A (en) * | 2007-04-06 | 2007-09-05 | 山东大学 | Use of bi-alkyl carboxylate surface activator in triple oil recovery |
| CN101279934A (en) * | 2007-04-04 | 2008-10-08 | 中国石油化工股份有限公司 | Aliphatic acid polyethenoxy ether sulphonate and preparation thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO170411C (en) * | 1990-04-02 | 1992-10-14 | Berol Nobel Ab | SURFACTIVE AGENTS AND THEIR USE IN OIL EXTRACTION |
-
2010
- 2010-04-15 CN CN201010147142A patent/CN102219897B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101279934A (en) * | 2007-04-04 | 2008-10-08 | 中国石油化工股份有限公司 | Aliphatic acid polyethenoxy ether sulphonate and preparation thereof |
| CN101029224A (en) * | 2007-04-06 | 2007-09-05 | 山东大学 | Use of bi-alkyl carboxylate surface activator in triple oil recovery |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102219897A (en) | 2011-10-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102219897B (en) | Disulfonate gemini surfactant with high temperature and salt resistance and preparation method thereof | |
| CN102219714B (en) | N,N-dual fat acyl diamine diacetate dipolyoxyethylene ether bisulphonate and preparation method thereof | |
| CN102220118B (en) | Oil displacement composition and preparation method thereof | |
| CN102218282B (en) | Dual-carboxylate gemini surfactant resistant to high temperature and high salt and preparation method thereof | |
| CN102277146B (en) | Composition for improving recovery ratio substantially and preparation method thereof | |
| CN102220119B (en) | Oil displacing method for reservoirs with high temperature and salinity | |
| CN102464598B (en) | Fatty acid amide polyoxylethylene ether benzene sulfonate and preparation method thereof | |
| CN102220121B (en) | Composition capable of improving recovery ratio considerably and preparation method thereof | |
| CN102220859B (en) | Oil flooding method for greatly improving recovery rate of crude oil | |
| CN102220123B (en) | Oil displacement method for tertiary oil recovery | |
| CN102220860B (en) | Polymer-surfactant binary compound oil displacement method | |
| CN103032055A (en) | Displacement method utilizing compound containing sulfonate negative non-surface active agent | |
| CN102220120B (en) | Binary compound flooding compound and preparation method thereof | |
| CN102219896B (en) | N,N-difattyacyl diamino diacetoxyl dipolyoxyethylene ether dicarboxylate and preparation method thereof | |
| CN102277148B (en) | Composition for improving recovery ratio of crude oil and preparation method thereof | |
| CN103031119B (en) | Sulfonate-containing anionic/nonionic surfactant composition and preparation method | |
| CN102373046B (en) | High efficiency anti-magnesium ions oil displacement agent and its preparation method | |
| CN102277147A (en) | Oil displacement method for high-temperature high-salt oil reservoir | |
| CN102220124B (en) | Oil displacement compound for tertiary oil recovery and preparation method thereof | |
| CN102373913B (en) | High-efficiency anti-magnesium ion oil displacement method | |
| CN102373043B (en) | Displacement agent suitable for MgCl2 injection water and preparation method thereof | |
| CN102373045B (en) | Seawater-based oil displacement agent and preparation method thereof | |
| CN102373040B (en) | Composition suitable for seawater-based oil displacement and its preparation method | |
| CN102373044B (en) | Oil displacement method suitable for MgCl2 water-type oil displacement agent | |
| CN102373041B (en) | Oil displacement method by use of seawater base oil displacement agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |