CN108558691A - A kind of star-like compound and preparation method thereof carrying intensive charge - Google Patents
A kind of star-like compound and preparation method thereof carrying intensive charge Download PDFInfo
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- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
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- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
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- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C09K8/58—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids
- C09K8/584—Compositions for enhanced recovery methods for obtaining hydrocarbons, i.e. for improving the mobility of the oil, e.g. displacing fluids characterised by the use of specific surfactants
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
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- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/72—Eroding chemicals, e.g. acids
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Abstract
The invention discloses a kind of star-like compound and preparation method thereof carrying intensive charge, which is prepared by following steps：Quantitative trimethylolpropane tris (3 aziridinyl propionic ester) reaction solution is added dropwise in the reaction bulb equipped with methylamine (or ethamine) aqueous solution and acidic catalyst and carries out first step aziridine ring-opening reaction；Quantitative 3 chlorine, 2 hydroxypropyl-trimethyl ammonium chloride is added into reaction solution again and carries out second step quaternary ammonium reaction, products therefrom is a kind of star-like compound carrying intensive charge.
Description
Technical field
The present invention relates to multi-quaternary ammonium salt cationic surfactant preparing technical fields, more particularly to a kind of to carry intensive electricity
Star-like compound of lotus and preparation method thereof.
Background technology
There are larger tension for aziridine ring structure in aziridines crosslinking agent, and activity is higher, can with amido, carboxyl and
Hydroxyl reaction forms the compound with hub-and-spoke configuration or reticular structure, how polycation season is introduced into such compound
Ammonium salt groups prepare new compound and apply in oil-gas mining, are the difficult points studied now.
There is the clay minerals such as such as montmorillonite, kaolin, chlorite in oil-gas reservoir, as them and incompatible extraneous current
When body contacts, it may occur that hydration swelling and dispersion migrate and block oil-gas reservoir channel, can be prevented and be subtracted using clay stabilizer
Light clay expands the injury to stratum with dispersion.There are many type of clay stabilizer at present, there is inorganic salts, inorganic base, nothing
Machine polymerize species, non-ionic polymers and cationic polymer etc., special using most and effect most preferably cationic polymer
It is not quaternary ammonium salt cationic polymer, quaternary ammonium salt cationic clay stabilizer easily by clay Preferential adsorption, can promote clay crystal layer
Between be dehydrated, reduce expansive force, effectively inhibit clay aquation, and can be embedded between clay crystal layer, hydrone is prevented to enter, reduce glutinous
The hydration swelling effect of soil has effect steady in a long-term since it is adsorbed securely on clay particle.But existing quaternary ammonium salt
Class clay stabilizer there are dosages it is big, anti-dilative is low and big to formation damage the problems such as,
Invention content
In order to extend the type of polycationic quaternary ammonium salt surfactant and the quantity of polycationic quaternary ammonium salt, the present invention
The star-like surfactant to be formed and carry active secondary amine is reacted with active amido with the aziridine crosslinker of high activity, is re-introduced into and takes
Quaternary ammonium salt reagent reaction with quaternary ammonium salt, obtains a kind of star-like compound carrying intensive charge.An object of the present invention exists
In providing a kind of star-like compound carrying intensive charge, the second object of the present invention is to provide the preparation side of the compound
Method.
In order to achieve the above objectives, the present invention uses following technical scheme：
A kind of star-like compound carrying intensive charge, structural formula are：
Wherein, R1- is-CH3Or-CH2CH3。
A kind of preparation method for the star-like compound carrying intensive charge as described in claim 1, includes the following steps：
To-three (the 3- aziridinyls third of middle addition trimethylolpropane of methylamine (or ethamine) aqueous solution and acidic catalyst
Acid esters) reaction solution progress aziridine ring-opening reaction, 5~7h is being reacted at 40~70 DEG C；
Under weak basic condition, the chloro- 2- hydroxypropyls of 3--trimethyl ammonia chloride aqueous ammonium progress is added into above-mentioned reactant
Quaternary ammonium reaction reacts 4~8h at 50~70 DEG C；Insoluble matter, concentration of reaction solution, with toluene column chromatography are removed after reaction
Method is isolated and purified with product, is dried under vacuum to constant weight and just obtains product.
In aziridine ring-opening reaction, trimethylolpropane-three (3- aziridinyls propionic ester) and methylamine (or ethamine) rub
You are than being 1:3.
In aziridine ring-opening reaction, the acidic catalyst is the phosphate aqueous solution that mass fraction is 85%, is used
Amount is the 1% of raw material gross mass.
In quaternary ammonium reaction, weak basic condition pH=9~10, reaction solution K2CO3It is adjusted to alkalescent.
In quaternary ammonium reaction, the amount of the substance of the chloro- 2- hydroxypropyls-trimethyl ammonium chlorides of 3- is trimethylolpropane-three
6 times of (3- aziridinyls propionic ester).
A kind of star-like compound carrying intensive charge is in oil-gas mining as the application of clay stabilizer.
Addition as clay stabilizer is the 0.2~1% of gross mass.
The present invention compared with the prior art, has the following advantages：
There are larger tension for aziridine ring structure in aziridines crosslinking agent, and activity is higher, can with amido, carboxyl and
Hydroxyl reaction forms the compound with hub-and-spoke configuration or reticular structure, in order to introduce polycation season into such compound
Ammonium salt groups, the present invention react to be formed with independent hub-and-spoke configuration with active amido with the aziridine crosslinker of high activity, then
The quaternary ammonium reagent reaction for carrying quaternary ammonium salt group is introduced, a kind of star-like chemical combination of the intensive charge of carrying of structure novel is obtained
Object.This kind of kind of star-like compound for carrying intensive charge can be widely used in preparing new material, fungicide, inhibit metal rotten
The fields such as erosion, fabric finishing, oil exploitation.
The present invention reacts the star-like surface to be formed and carry active secondary amine with the aziridine crosslinker of high activity with active amido
Activating agent is re-introduced into the quaternary ammonium salt reagent reaction for carrying quaternary ammonium salt, obtains a kind of star-like compound carrying intensive charge, in order to
The preparation for carrying the star-like compound of intensive charge provides a kind of simple preparation method.
This clay stabilizer for carrying intensive charge, can be more simultaneously due to containing 18 quaternary ammonium salt groups in molecule
Point acts on electronegative clay particle, and degree of absorption is high, to realize the purpose of low dosage, high anti-dilative.
Description of the drawings
Fig. 1 is the chemical structural formula of the present invention；
Fig. 2 is present invention reaction synthetic route chart.
Specific implementation mode
As depicted in figs. 1 and 2, reaction equation of the invention is：
Wherein, R1It is-CH3Or-CH2CH3。
According to above-mentioned reaction mechanism, the present invention adopts the following technical scheme that
A kind of star-like compound carrying intensive charge, the structural formula of the compound are：
Wherein, R1It is-CH3Or-CH2CH3。
The star-like compound for preparing a kind of above-mentioned intensive charge of carrying, steps of the method are：
It is dripped in the reaction bulb of methylamine (or ethamine) aqueous solution and acidic catalyst that are 20~70% equipped with mass fraction
Trimethylolpropane-three (3- aziridinyls propionic ester) reaction solution is added to carry out aziridine ring-opening reaction, wherein hydroxymethyl-propane-three
The molar ratio of (3- aziridinyls propionic ester) and methylamine (or ethamine) is 1:3,5~7h is reacted at 40~70 DEG C；It again will be above-mentioned anti-
Answer liquid K2CO3Alkaline (pH=9~10) are adjusted to, it is quaternary ammoniated that the chloro- 2- hydroxypropyls of 3--trimethyl ammonium chloride progress second step is added
Reaction, the amount of the substance of the chloro- 2- hydroxypropyls-trimethyl ammonium chlorides of wherein 3- is (the 3- aziridinyl propionic acid of trimethylolpropane-three
Ester) 6 times, at 50~70 DEG C react 4~8h；Insoluble matter, concentration of reaction solution, with toluene column chromatography are removed after reaction
It is isolated and purified with product, constant weight is dried under vacuum to and just obtains product.
Embodiment 1
In the methylamine water solution (23.25g, wherein 4.65g containing methylamine, 0.15mol) and acid for being 20% equipped with mass fraction
Property catalyst (85%H3PO4, 0.25g), 40 DEG C are warming up to, (the 3- a word used for translations of trimethylolpropane-three that mass fraction is 70% are added dropwise
Third piperidinyl propionic ester) aqueous solution (35.42g, wherein contain trimethylolpropane-three (3- aziridinyls propionic ester) 21.25g,
0.05mol), time for adding 40min.After being added dropwise, it is warming up to 50 DEG C of reaction 7h；By above-mentioned reaction solution K2CO3It is adjusted to weak
Alkaline (pH=9~10), be added dropwise chloro- 2- hydroxypropyls-trimethyl ammonia chloride aqueous ammoniums of 3- that mass fraction is 80% (70.50g,
Wherein contain the chloro- 2- hydroxypropyls of 3--trimethyl ammonium chloride 56.40g, 0.30mol), time for adding 60min reacts 8h at 50 DEG C；
Insoluble matter is removed after reaction, and concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight
Obtain product.
The structural formula of 1 products therefrom of embodiment is：
1H NMR (300MHz, DMSO)：δ 4.77~4.84 (m, 24H), 3.94 (s, 6H), 3.63~3.68 (m, 18H),
3.25~3.51 (m, 48H), 3.30 (s, 117H), 2.70 (t, 6H), 1.69 (m, 2H), 0.84 (t, 3H) ppm.
13C NMR (300MHz, DMSO)：δ 173.2,68.1,65.7,58.4,55.1,50.7,35.7,27.3,22.9,
7.1ppm。
Embodiment 2
In the ethylamine solution (9.54g, wherein 6.75g containing ethamine, 0.15mol) and acidity for being 70% equipped with mass fraction
Catalyst (85%H3PO4, 0.25g), 50 DEG C are warming up to, (the 3- a word used for translations third of trimethylolpropane-three that mass fraction is 70% are added dropwise
Piperidinyl propionic ester) aqueous solution (35.42g, wherein contain trimethylolpropane-three (3- aziridinyls propionic ester) 21.25g,
0.05mol), time for adding 40min.After being added dropwise, it is warming up to 70 DEG C of reaction 5h；By above-mentioned reaction solution K2CO3It is adjusted to weak
Alkaline (pH=9~10), be added dropwise chloro- 2- hydroxypropyls-trimethyl ammonia chloride aqueous ammoniums of 3- that mass fraction is 80% (70.50g,
Wherein contain the chloro- 2- hydroxypropyls of 3--trimethyl ammonium chloride 56.40g, 0.30mol), time for adding 60min reacts 4h at 70 DEG C；
Insoluble matter is removed after reaction, and concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight
Just product is obtained.
The structural formula of 2 products therefrom of embodiment is：
1H NMR (300MHz, DMSO)：δ 4.84 (m, 12H), 4.77 (d, 12H), 3.63~3.68 (m, 18H), 3.25~
3.51 (m, 54H), 3.30 (s, 108H), 2.69 (t, 6H), 1.69 (m, 2H), 1.25 (t, 9H), 0.84 (t, 3H) ppm.
13C NMR (300MHz, DMSO)：δ 173.1,72.5,65.6,58.4,55.6,35.7,27.3,22.9,7.7~
8.3ppm。
The performance characterization of clay stabilizer
(1) anti-dilative of clay stabilizer and the test of water-fastness rate
Reference standard SY/T 5971-2016《Oil-gas field fracturing is acidified and water filling clay stabilizer method of evaluating performance》
With Q/SH 0053-2010《The requirement of clay stabilizer technology》Middle centrifugal process method, it is molten in clay stabilizer by measuring sodium bentonite
Expansion increment in liquid and distilled water evaluates anti-dilative.Determine the clay stabilizer of embodiment 1 and embodiment 2 in water anti-
Swollen rate and water-fastness rate.The results are shown in Table 1.
The anti-dilative of 1 clay stabilizer of table and water-fastness rate
As seen from table, for clay stabilizer of the invention under 0.2% dosage, the anti-dilative in riverfrac treatment liquid is equal
Higher than 85%, water-fastness rate is more than 90%；Clay stabilizer is under 0.5% dosage, the anti-dilative in riverfrac treatment liquid
It is above 90%, water-fastness rate is more than 94%；Inorganic salts clay stabilizer (potassium chloride and ammonium chloride) is compareed, 2.0%
Dosage under, anti-dilative is below 70%.
(2) compatibility is tested
Compatibility observation is carried out to the clay stabilizer and fracturing fluid base fluid and acid solution of embodiment 1 and embodiment 2, as a result
As shown in table 2.
The compatibility of 2 clay stabilizer of table is tested
From table 2 it can be seen that the clay stabilizer of the present invention is mixed with fracturing fluid base fluid and acid solution, no layering, precipitation
It is generated with suspension phenomenon, compatibility is good.
The above content is it is made for the present invention be further described, and it cannot be said that the present invention specific implementation mode only
It is limited to this, for those of ordinary skill in the art to which the present invention belongs, without departing from the inventive concept of the premise, also
Several simple deduction or replace can be made, the present invention is all shall be regarded as belonging to and determines protection by the claims submitted
Range.
Claims (8)
1. a kind of star-like compound carrying intensive charge, which is characterized in that its structural formula is：
Wherein, R1- is-CH3Or-CH2CH3。
2. a kind of preparation method for the star-like compound carrying intensive charge as described in claim 1, which is characterized in that including
Following steps：
It is anti-to the middle addition trimethylolpropane-three (3- aziridinyls propionic ester) of methylamine or ethylamine solution and acidic catalyst
It answers liquid to carry out aziridine ring-opening reaction, 5~7h is being reacted at 40~70 DEG C；
Under weak basic condition, the chloro- 2- hydroxypropyls of 3--trimethyl ammonia chloride aqueous ammonium progress quaternary amine is added into above-mentioned reactant
Change reaction, 4~8h is reacted at 50~70 DEG C；Insoluble matter is removed after reaction, and concentration of reaction solution is pure with toluene column chromatography
Product is isolated in change, is dried under vacuum to constant weight and is just obtained product.
3. a kind of preparation method of star-like compound carrying intensive charge according to claim 2, which is characterized in that
In aziridine ring-opening reaction, trimethylolpropane-three (3- aziridinyls propionic ester) and methylamine or ethamine molar ratio are 1:3.
4. a kind of preparation method of star-like compound carrying intensive charge according to claim 2, it is characterised in that：
In aziridine ring-opening reaction, the acidic catalyst is the phosphate aqueous solution that mass fraction is 85%, and dosage is that raw material is total
The 1% of quality.
5. a kind of preparation method of star-like compound carrying intensive charge according to claim 2, which is characterized in that
In quaternary ammonium reaction, weak basic condition pH=9~10, reaction solution K2CO3It is adjusted to alkalescent.
6. a kind of preparation method of star-like compound carrying intensive charge according to claim 2, which is characterized in that
In quaternary ammonium reaction, the amount of the substance of the chloro- 2- hydroxypropyls-trimethyl ammonium chlorides of 3- is (the 3- aziridinyls of trimethylolpropane-three
Propionic ester) 6 times.
7. a kind of star-like compound described in claim 1 carrying intensive charge is in oil-gas mining as clay stabilizer
Using.
8. a kind of application of the star-like compound carrying intensive charge according to claim 7 as clay stabilizer,
It is characterized in that, the addition mass percent as clay stabilizer is 0.2~1%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111944509A (en) * | 2020-08-26 | 2020-11-17 | 肯特催化材料股份有限公司 | Anti-swelling agent for shale gas fracturing |
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| CN102942493A (en) * | 2012-11-09 | 2013-02-27 | 西南石油大学 | Terquaternary cation surface active agent and preparation method |
| WO2016172436A1 (en) * | 2015-04-23 | 2016-10-27 | Temple University-Of The Commonwealth System Of Higher Education | Polycationic amphiphiles and polymers thereof as antimicrobial agents and methods using same |
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2018
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| CN102942493A (en) * | 2012-11-09 | 2013-02-27 | 西南石油大学 | Terquaternary cation surface active agent and preparation method |
| WO2016172436A1 (en) * | 2015-04-23 | 2016-10-27 | Temple University-Of The Commonwealth System Of Higher Education | Polycationic amphiphiles and polymers thereof as antimicrobial agents and methods using same |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111944509A (en) * | 2020-08-26 | 2020-11-17 | 肯特催化材料股份有限公司 | Anti-swelling agent for shale gas fracturing |
| CN111944509B (en) * | 2020-08-26 | 2022-05-03 | 肯特催化材料股份有限公司 | Anti-swelling agent for shale gas fracturing |
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