CN106986775A - Tertiary amines CO2/N2Switching mode Gemini surface active and its synthetic method - Google Patents
Tertiary amines CO2/N2Switching mode Gemini surface active and its synthetic method Download PDFInfo
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Abstract
The invention discloses a kind of tertiary amines CO2/N2Switching mode Gemini surface active and its synthetic method.This method comprises the following steps：(1) ethylenediamine is dissolved in absolute ethyl alcohol, heats, add the ethanol solution dissolved with bromododecane, stirred, obtain reaction solution I；(2) reaction solution I is cooled down, is filtered, drying obtains solid powder；(3) solid powder is dissolved in absolute ethyl alcohol, heated, then be added dropwise thereto respectively dissolved with N, the chlorine propylamine of N dimethyl 3 and the ethanol solution dissolved with KI, stirring obtains reaction solution II；(4) reaction solution II is cooled down, washing and drying obtains target product, is added into closed pressure vessel, adds water, and is passed through CO2Surfactant is obtained, N is passed through2It is non-surface-active agent to make surfactant transitions.The inventive method is simple, can easily realize the phase co-conversion between surfactant and non-surface-active agent, makes the repeatable utilization of surfactant, has broad application prospects.
Description
Technical field
The invention belongs to technical field of chemical synthesis, and in particular to a kind of tertiary amines CO2/N2Live on switching mode Gemini surfaces
Property agent and its synthetic method.
Background technology
In recent years, Green Chemistry is also increasingly paid attention to, and traditional surfactant cannot participate in during use
Reaction, but the separation after its use is also extremely difficult；Therefore, this waste for having resulted in resource and a certain degree of ring
Border is destroyed.
CO2/N2Surfactant is being used as a kind of new, reusable green surfactant
During by controlling CO2Addition with separating, easily can realize between non-surface-active agent and surfactant
Phase co-conversion, so, the separation of surfactant after usage just become relatively easy, and CO2It is that one kind is cheap, is easy to get
Raw material, this just makes CO2The research of surfactant is also more and more popular.
CO2/N2Surfactant common are amidino groups class surfactant and guanidine radicals class surfactant, wherein
The synthesis cost of conventional amidino groups class surfactant is higher, therefore limits its commercial synthesis, and the carbon of guanidine radicals class surfactant
Sour hydrogen salt, which is decomposed, needs higher temperature, and its reversible process is difficult to, limits it and use.
Therefore, start within 2010, the research directions of domestic and foreign scholars gradually from surfactant turned to it is more gentle, can
The higher amine substance of reverse efficiency.
The content of the invention
For above-mentioned deficiency of the prior art, the present invention provides a kind of tertiary amines CO2/N2Live on switching mode Gemini surfaces
Property agent and its synthetic method, tertiary amine structure are gentleer, reversible more efficient.
A kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, comprises the following steps：
(1) ethylenediamine is dissolved in absolute ethyl alcohol, heating water bath adds the bromine dissolved with 0.1~0.5mol to 65~70 DEG C
For the ethanol solution of dodecane, 20~24h is stirred, reaction solution I is obtained；Wherein, the w/v of ethylenediamine and absolute ethyl alcohol is 2
~4:20~22；The mol ratio of bromododecane and ethylenediamine is 18~20:5~9；
(2) reaction solution I is cooled down at room temperature, and filtering washs filter cake with absolute ethyl alcohol 3~5 times, then at 50~62 DEG C of bakings
It is dry, obtain N, N '-bis- dodecyls ethylenediamine；Its synthetic reaction formula is：
(3) step (2) gains are dissolved in absolute ethyl alcohol, oil bath heating to 75~80 DEG C, then be added dropwise respectively dissolved with
The ethanol solution of N, N- dimethyl -3- chlorine propylamine and KI, stirs 20~24h, obtains reaction solution II；Wherein, N, N- dimethyl-
The mol ratio of 3- chlorine propylamine and KI is 1:1；
(4) reaction solution II is cooled down at room temperature, is washed with absolute ethyl alcohol 3~5 times, then at 50~62 DEG C of drying, obtains target
Product N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine, its synthetic reaction formula is：
It is added into closed pressure vessel, adds water, is passed through CO2, obtain tertiary amines CO2/N2Live on switching mode Gemini surfaces
Property agent.
Further, bath temperature is 70 DEG C in step (1), and the mol ratio of bromododecane and ethylenediamine is 20:9.
Further, when the ethanol solution dissolved with bromododecane being added dropwise in step (1), time for adding is controlled in 1~2h.
Further, the w/v of ethylenediamine and absolute ethyl alcohol is 2.7 in step (1):20.
Further, oil bath temperature is 80 DEG C, N, N- dimethyl -3- chlorine propylamine, KI and N, N in step (3) '-bis-
The mol ratio of dodecyl ethylenediamine is 2.2:2.2:1.
Further, it is added dropwise respectively in step (3) dissolved with N, the ethanol solution of N- dimethyl -3- chlorine propylamine and KI
When, time for adding is controlled in 3~4h.
Beneficial effects of the present invention are：
1st, tertiary amines CO2/N2Switching mode Gemini surface active is a kind of new, reusable green surface
Activating agent, CO is passed through during use by priority2And N2, can easily realize surfactant and on-surface-active
Phase co-conversion between agent, so, the separation of surfactant after usage just become relatively easy, make surfactant can
Recycling.
2nd, the tertiary amines CO prepared using the inventive method2/N2Switching mode Gemini surface active, compared to biography
The single-stranded surfactant of system, the pC of the Gemini surface active of synthesis20It is increased slightly, each surfactant molecule is on boundary
The area A in faceminIt is smaller, adsorbance ΓmaxIt is larger, show N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls second
Diamines is being passed through CO2There is preferable surface-active afterwards.
3rd, N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine and CO2Reaction generation N, N '-two
The bicarbonate cationic complex of (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine, its electrical conductivity is also fast therewith
Speed rises, then is passed through N2Afterwards, bicarbonate complex compound is decomposed into original state, becomes neutral non-ionic compound, solution electricity
Conductance also declines therewith, reverts to initial value, it was confirmed that N, N '-two (N, N- dimethyl propylamine)-N that the present invention is prepared,
The CO of N '-bis- dodecyls ethylenediamine2Response, i.e. CO2Switch property.
4th, in closed pressure vessel, with the increase of carbon dioxide intake, container inner pressure also increases therewith, dioxy
Change meltage of the carbon in water also to increase, increase carbon dioxide and N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- 12
The haptoreaction area of alkylethylene diamines, improves the transformation efficiency and speed of surfactant.
Brief description of the drawings
Fig. 1 is to be passed through excessive CO2Afterwards, the relation curve of surface tension and target product concentration；
Fig. 2 is that under 0.2% target product concentration conditions, surface tension is with injection CO2The change curve of volume；
Fig. 3 be under 0.2% target product concentration conditions, electrical conductivity with duration of ventilation variation rule curve；
Fig. 4 is to distinguish three alternatings in same solution to lead to CO2And N2Reversible transition is carried out, when forming surfactant,
Determine change curve of each foam volume with target product surface surfactant concentration.
Embodiment
The embodiment to the present invention is described below, in order to which those skilled in the art understand this hair
It is bright, it should be apparent that the invention is not restricted to the scope of embodiment, for those skilled in the art,
As long as various change is in the spirit and scope of the present invention that appended claim is limited and is determined, these changes are aobvious and easy
See, all are using the innovation and creation of present inventive concept in the row of protection.
Embodiment 1
A kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, comprises the following steps：
(1) 0.045mol ethylenediamines are dissolved in 20mL absolute ethyl alcohols, heating water bath to 70 DEG C, then be added dropwise thereto dissolved with
The ethanol solution of 0.1mol bromododecane, control dissolved with the ethanol solution of bromododecane time for adding be 1.5h, stir
24h is mixed, reaction solution I is obtained；
(2) reaction pours out reaction solution I while hot after terminating, and cools down at room temperature, filters, filter cake is washed with absolute ethyl alcohol 3 times,
Dried under conditions of 50 DEG C, obtain white solid powder N, N '-bis- dodecyls ethylenediamine；
(3) solid powder obtained by step (2) is dissolved in absolute ethyl alcohol, oil bath heating is added dropwise to 80 DEG C, then thereto
Respectively dissolved with 0.022mol N, the ethanol solution of N- dimethyl -3- chlorine propylamine and 0.022mol KI, control is molten respectively
There is a N, the time for adding of the ethanol solution of N- dimethyl -3- chlorine propylamine and KI is 4h, after stirring 24h, obtain reaction solution II；
(4) reaction pours out reaction solution II while hot after terminating, and cools down, is washed with absolute ethyl alcohol 3 times, then at 50 DEG C at room temperature
Under conditions of dry, obtain target product N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine, then by 0.2g
Target product be added in closed pressure vessel, add 100ml water, be passed through 400ml CO2Obtain tertiary amines CO2/N2Switching mode
Gemini surface active, then it is passed through 400ml N2So that surfactant transitions are into non-surface-active agent, surface-active is realized
Phase co-conversion between agent and non-surface-active agent.
Embodiment 2
A kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, comprises the following steps：
(1) ethylenediamine is dissolved in absolute ethyl alcohol, heating water bath is to 65 DEG C, then adds the bromo ten dissolved with 0.5mol thereto
The ethanol solution of dioxane, it is 1h to control dissolved with the time for adding of the ethanol solution of bromododecane, stirs 20h, obtains reaction solution I；
Wherein, the w/v of ethylenediamine and absolute ethyl alcohol is 4:22；The mol ratio of ethylenediamine and bromododecane is 5:18；
(2) reaction pours out reaction solution I while hot after terminating, and cools down at room temperature, filters, filter cake is washed with absolute ethyl alcohol 4 times,
Dried under conditions of 60 DEG C, obtain white solid powder N, N '-bis- dodecyls ethylenediamine；
(3) solid powder obtained by step (2) is dissolved in absolute ethyl alcohol, oil bath heating is added dropwise to 75 DEG C, then thereto
Respectively dissolved with 0.05mol N, the ethanol solution of N- dimethyl -3- chlorine propylamine and 0.05mol KI, control respectively dissolved with
The time for adding of the ethanol solution of N, N- dimethyl -3- chlorine propylamine and KI is 4h, after stirring 20h, obtains reaction solution II；
(4) reaction pours out reaction solution II while hot after terminating, and cools down, is washed with absolute ethyl alcohol 3 times, then at 62 DEG C at room temperature
Under conditions of dry, obtain N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine, then 0.5g target is produced
Thing is added in closed pressure vessel, adds 100ml water, is passed through 1000ml CO2Obtain tertiary amines CO2/N2Switching mode Gemini
Surfactant, then it is passed through 1000ml N2So that surfactant transitions are into non-surface-active agent, realize surfactant with it is non-
Phase co-conversion between surfactant.
Embodiment 3
A kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, comprises the following steps：
(1) ethylenediamine is dissolved in absolute ethyl alcohol, heating water bath is to 60 DEG C, then adds the bromo dissolved with 0.25mol thereto
The ethanol solution of dodecane, it is 2h to control dissolved with the time for adding of the ethanol solution of bromododecane, stirs 24h, obtains reaction solution
Ⅰ；Wherein, the w/v of ethylenediamine and absolute ethyl alcohol is 2:20；The mol ratio of ethylenediamine and bromododecane is 7:19；
(2) reaction pours out reaction solution I while hot after terminating, and cools down at room temperature, filters, filter cake is washed with absolute ethyl alcohol 3 times,
Dried under conditions of 62 DEG C, obtain white solid powder N, N '-bis- dodecyls ethylenediamine；
(3) solid powder obtained by step (2) is dissolved in absolute ethyl alcohol, oil bath heating is added dropwise to 76 DEG C, then thereto
Respectively dissolved with 0.042mol N, the ethanol solution of N- dimethyl -3- chlorine propylamine and 0.042mol KI, control is molten respectively
There is a N, the time for adding of the ethanol solution of N- dimethyl -3- chlorine propylamine and KI is 3h, after stirring 24h, obtain reaction solution II；
(4) reaction pours out reaction solution II while hot after terminating, and cools down, is washed with absolute ethyl alcohol 3 times, then at 60 DEG C at room temperature
Under conditions of dry, obtain N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine, then 0.1g target is produced
Thing is added in closed pressure vessel, adds 100ml water, is passed through 200ml CO2Obtain tertiary amines CO2/N2Switching mode Gemini tables
Face activating agent, then it is passed through 200ml N2So that surfactant transitions are into non-surface-active agent, surfactant and non-table are realized
Phase co-conversion between the activating agent of face.
Experimental example
To the gained tertiary amines CO of embodiment 12/N2Switching mode Gemini surface active carries out mapping surface properties, surface
Power detection, foaming properties invertibity and the detection of electrical conductivity invertibity.
Surface tension is detected：The assay method of surface tension mainly has capillary rise method, suspension ring method, sessile drop method and bubble
Maximum pressure method etc., experiment uses JK99B Full-automatic tension instrument, and product surface is determined by suspension ring method；Configure series concentration
Solution (0.1wt%, 0.2wt%, 0.3wt%, 0.4wt% and 0.5wt% aqueous surfactant solution), according to concentration by
It is high to Low, it is passed through CO2The surface tension of sequentially determining solution after gas.
According to critical micelle concentration CMC, γ of surfactantcmcWith γ-logC curve maps, it is computed and Linear Quasi
Close, surfactant other important properties parameters, pC can be tried to achieve20、ΓmaxAnd Amin。
ΓmaxSaturated extent of adsorption of the surfactant molecule in liquid-vapor interface is represented, is inhaled according to formula (1) Gibbs isothermals
Subsidiary formula journey is calculated.Wherein d γ/dlogC is the slope of γ-logC straight line portions；Wherein T (K) is test temperature, and R is that gas is normal
Number (8.314J/molK), n takes 2.
AminWhen representing that liquid-vapor interface reaches saturation, the average area of interfacial molecular is binding molecule limit area, i.e.,
Minimum area shared by binding molecule.Can be according to ΓmaxCalculated and obtained by formula (2), wherein NAFor Avgadro constant
(6.02×1023mol-1)。
pC20Represent the efficiency of surfactant, C20For the surface tension of pure water is reduced into 20mNm-1Required surface
Surfactant concentration, C20Negative logarithm be pC20(pC20=-logC20), for weighing surfactant molecule in the poly- of gas-liquid interface
Collect efficiency, pC20Value is bigger, and surfactant molecule is more they tended in adsorption at gas-liquid surface, more they tends to form micella, reduction surface
The efficiency of power is higher, pC20It can be tried to achieve according to formula (3).Wherein, γ 0 is the surface tension that temperature is pure water under 298.15k,
Its value is 71.27mNm-1。
The surface tension (γ) of gained-log concentration (logC) curve such as Fig. 1, in closed pressure vessel, surface tension
With being passed through CO2The curve of Volume Changes such as Fig. 2, the critical micell that can release surfactant by the catastrophe point of Fig. 1 curves is dense
Spend (CMC), corresponding surface tension is γcmc, it the results are shown in Table 1.
The critical micelle concentration of table 1 (CMC) and γcmc
Its surface performance is detected using conventional method, its testing result is shown in Table 2.
Its surface performance parameter of table 2
Electrical conductivity invertibity is detected：Prepare 0.01mol/L N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecanes
The solution of base ethylenediamine, in 25 DEG C of closed pressure vessel, tests its initial conductivity value, and with 10mL/min speed to
CO is passed through in solution2Gas, surveys an electrical conductivity, when the reaction in system reaches balance, conductivity value tends to be flat every 5min
It is slow；N is passed through into system with 10mL/min speed again2, recording solution conductivity value, when the electrical conductivity of system tends to be flat again
It is slow, a minimum value is reduced to, stops ventilation；Repeat real three times, the electrical conductivity versus time curve of surfactant is such as
Shown in Fig. 3.
Foaming properties invertibity is detected：By product be made into various concentrations surfactant solution (0.1wt%,
0.2wt%, 0.3wt%, 0.4wt%, 0.5wt%, 0.6wt%), after the solution foaming of the surfactant configured, base
This non-foam is produced, and CO is then passed through thereto2, then the graduated cylinder that 1000mL is immediately transferred into after rotation 60s is poured into foaming instrument
In, now there are a large amount of foams to produce, after foam is wholly absent, N is passed through into solution2, then pour into foaming instrument after rotation 60s
It is immediately transferred into 1000mL graduated cylinder, it can be found that basic non-foam is produced in graduated cylinder, experiment three times is repeated, as a result such as Fig. 4
It is shown.
Conclusion
1st, from table 1 it follows that the tertiary amines CO of synthesis2/N2Switching mode Gemini surface active with it is traditional single-stranded
Surfactant, which is compared, has lower γcmcValue.
2nd, figure it is seen that not being passed through CO2When, its surface tension force is basic and water is consistent, with
CO2Intake increase, its surface tension reduces rapidly, is passed through surface tension after 200mL and reduces amplitude and slows down, until
It is substantially unchanged after 400mL, illustrate that now non-surface-active agent has been basically completed to the transformation of surfactant.
3rd, from Table 2, it can be seen that compared to traditional single-stranded surfactant of same carbon atoms number purpose, the uncle of synthesis
Amine CO2/N2The pC of switching mode Gemini surface active20It is increased slightly, area of each surfactant molecule at interface
AminIt is smaller, adsorbance ΓmaxLarger, this shows the tertiary amines CO of synthesis2/N2Live on the surface of switching mode Gemini surface active
Property parameter is more preferable.
4th, from figure 3, it can be seen that the conductivity value of solution original state is slightly above zero, with CO2Constantly it is passed through, N,
N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine and CO2Reaction generation N, (N, the N- dimethyl propylenes of N '-two
Amine)-N, the bicarbonate complex compound (quaternary surfactant is completely dissociated into) of N '-bis- dodecyls ethylenediamine, electrical conductivity is fast
Speed rises, and reaches maximum in 80min or so electrical conductivity and keeps balance, shows that now surfactant transitions efficiency is maximum,
It is subsequently passed N2, bicarbonate complex compound is decomposed into original state again, becomes neutral non-ionic compound, now in solution
Electrical conductivity declines rapidly, gradually reverts to initial value, and the CO that experiment confirms the surfactant of synthesis is repeated by electrical conductivity2
Response, i.e. CO2Switch property.
5th, as can be seen from Figure 4 with the increase of surfactant concentration, system foam volume increase, when concentration reaches one
Continue to increase surfactant concentration after definite value, foam volume change is smaller, gradually tends to be steady, and maximum foam volume is
650mL。
6th, the N that the present invention is prepared, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine can be with two
Carbonoxide formation ionic complex, can be used as CO2/N2Surfactant, while having CO2Switch invertibity.
Claims (6)
1. a kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, it is characterised in that including following step
Suddenly：
(1) ethylenediamine is dissolved in absolute ethyl alcohol, heating water bath adds the bromo ten dissolved with 0.1~0.5mol to 65~70 DEG C
The ethanol solution of dioxane, stirs 20~24h, obtains reaction solution I；Wherein, the w/v of ethylenediamine and absolute ethyl alcohol is 2~4:
20~22；The mol ratio of bromododecane and ethylenediamine is 18~20:5~9；
(2) reaction solution I is cooled down at room temperature, and filtering washs filter cake with absolute ethyl alcohol 3~5 times, then at 50~62 DEG C of drying, obtains
N, N '-bis- dodecyl ethylenediamines；
(3) step (2) gains are dissolved in absolute ethyl alcohol, oil bath heating is to 75~80 DEG C, then is added dropwise respectively dissolved with N, N-
The ethanol solution of dimethyl -3- chlorine propylamine and KI, stirs 20~24h, obtains reaction solution II；Wherein, N, N- dimethyl -3- chlorine
The mol ratio of propylamine and KI is 1:1；
(4) reaction solution II is cooled down at room temperature, is washed with absolute ethyl alcohol 3~5 times, then at 50~62 DEG C of drying, obtains target product
N, N '-two (N, N- dimethyl propylamine)-N, N '-bis- dodecyls ethylenediamine, is added into closed pressure vessel, adds water,
It is passed through CO2, obtain tertiary amines CO2/N2Switching mode Gemini surface active.
2. tertiary amines CO according to claim 12/N2The synthetic method of switching mode Gemini surface active, its feature exists
In bath temperature described in step (1) is 70 DEG C, and the mol ratio of bromododecane and ethylenediamine is 20:9.
3. tertiary amines CO according to claim 12/N2The synthetic method of switching mode Gemini surface active, its feature exists
In when the ethanol solution dissolved with bromododecane being added dropwise in step (1), time for adding is controlled in 1~2h.
4. tertiary amines CO according to claim 12/N2The synthetic method of switching mode Gemini surface active, its feature exists
In the w/v of ethylenediamine and absolute ethyl alcohol described in step (1) is 2.7:20.
5. tertiary amines CO according to claim 12/N2The synthetic method of switching mode Gemini surface active, its feature exists
In, oil bath temperature described in step (3) be 80 DEG C, N, N- dimethyl -3- chlorine propylamine, KI and N, N '-bis- dodecyl second
The mol ratio of diamines is 2.2:2.2:1.
6. tertiary amines CO according to claim 12/N2The synthetic method of switching mode Gemini surface active, its feature exists
In being added dropwise respectively in step (3) dissolved with N, during the ethanol solution of N- dimethyl -3- chlorine propylamine and KI, time for adding is controlled
System is in 3~4h.
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| CN113621357A (en) * | 2020-05-08 | 2021-11-09 | 中国石油天然气股份有限公司 | Carbon dioxide response self-thickening intelligent fluid based on supermolecule self-assembly |
| WO2021223609A1 (en) * | 2020-05-08 | 2021-11-11 | 中国石油天然气股份有限公司 | Carbon-dioxide-responsive self-thickening intelligent fluid based on supramolecular self-assembly |
| CN113621357B (en) * | 2020-05-08 | 2022-07-05 | 中国石油天然气股份有限公司 | Carbon dioxide response self-thickening intelligent fluid based on supermolecule self-assembly |
| RU2791544C1 (en) * | 2020-05-08 | 2023-03-09 | Петрочайна Компани Лимитед | Self-thickening carbon dioxide-responsive smart fluid based on supramolecular self-assembly |
| US11952536B2 (en) | 2020-05-08 | 2024-04-09 | Petrochina Company Limited | Carbon-dioxide-responsive self-thickening intelligent fluid based on supramolecular self-assembly |
| CN111545086A (en) * | 2020-05-27 | 2020-08-18 | 新疆大学 | Reversible switch type foam system and preparation method thereof |
| CN114716392A (en) * | 2022-05-06 | 2022-07-08 | 四川纵深能源科技有限公司 | Piperazine CO2/N2Response double-tail surfactant, preparation method and application |
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