CN106986775B - 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.Method includes the following steps: ethylenediamine is dissolved in dehydrated alcohol by (1), heating adds the ethanol solution dissolved with bromododecane, stirs, obtains reaction solution I；(2) cooling reaction solution I, is filtered, and drying obtains solid powder；(3) solid powder is dissolved in dehydrated alcohol, is heated, then be added dropwise thereto respectively dissolved with N, N- dimethyl -3- chlorine propylamine and the ethanol solution dissolved with potassium iodide, stirring obtains reaction solution II；(4) cooling reaction solution II, washing and drying obtain target product, are added into closed pressure vessel, add water, be passed through CO2Surfactant is obtained, N is passed through2Make surfactant transitions non-surface-active agent.The method of the present invention is simple, can easily realize the phase co-conversion between surfactant and non-surface-active agent, keep surfactant reusable, have 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/N2The surface switching mode Gemini is living
Property agent and its synthetic method.
Background technique
In recent years, Green Chemistry is also got more and more attention, and traditional surfactant during use, cannot participate in
Reaction, but the separation after its use is also extremely difficult；Therefore, this has resulted in the waste of resource and a degree of ring
Border is destroyed.
CO2/N2Surfactant is being used as a kind of novel, reusable green surfactant
During by control CO2Addition with separate, can easily realize between non-surface-active agent and surfactant
Phase co-conversion, in this way, the separation of surfactant after usage just becomes relatively easily, 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 common amidino groups class surfactant is higher, therefore limits its commercial synthesis, and the carbon of guanidine radicals class surfactant
Sour hydrogen salt, which decomposes, needs higher temperature, and reversible process is difficult to carry out, and limits its use.
Therefore, start within 2010, the research direction of domestic and foreign scholars gradually from surfactant turned to it is more mild, can
The higher amine substance of reverse efficiency.
Summary of the invention
For above-mentioned deficiency in the prior art, the present invention provides a kind of tertiary amines CO2/N2The surface switching mode Gemini is living
Property agent and its synthetic method, tertiary amine structure are milder, reversible more efficient.
A kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, comprising the following steps:
(1) ethylenediamine is dissolved in dehydrated alcohol, heating water bath adds the bromine dissolved with 0.1~0.5mol to 65~70 DEG C
For the ethanol solution of dodecane, stirring 20~for 24 hours, obtain reaction solution I；Wherein, the w/v of ethylenediamine and dehydrated alcohol is 2
~4:20~22；The molar ratio of bromododecane and ethylenediamine is 18~20:5~9；
(2) reaction solution I is cooled down at room temperature, and filtering is washed filter cake 3~5 times with dehydrated alcohol, is dried then at 50~62 DEG C
It is dry, obtain N, the bis- dodecyl ethylenediamines of N '-；Its synthetic reaction formula are as follows:
(3) step (2) gains are dissolved in dehydrated 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 potassium iodide, stirring 20~for 24 hours, obtain reaction solution II；Wherein, N, N- dimethyl-
The molar ratio of 3- chlorine propylamine and potassium iodide is 1:1；
(4) reaction solution II is cooled down at room temperature, is washed 3~5 times with dehydrated alcohol, is dried then at 50~62 DEG C, is obtained target
The bis- dodecyl ethylenediamines of product N, N '-two (N, N- dimethyl propylamine)-N, N '-, synthetic reaction formula are as follows:
It is added into closed pressure vessel, adds water, be passed through CO2, obtain tertiary amines CO2/N2The surface switching mode Gemini
Activating agent.
Further, bath temperature is 70 DEG C in step (1), and the molar 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 dehydrated alcohol is 2.7:20 in step (1).
Further, oil bath temperature is that 80 DEG C, N, N- dimethyl -3- chlorine propylamine, potassium iodide and N, N '-are bis- in step (3)
The molar 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 potassium iodide
When, time for adding is controlled in 3~4h.
The invention has the benefit that
1, tertiary amines CO2/N2Switching mode Gemini surface active is a kind of novel, reusable green surface
Activating agent, during use by being successively passed through CO2And N2, can easily realize surfactant and on-surface-active
Phase co-conversion between agent, in this way, the separation of surfactant after usage just becomes relatively easily, to make surfactant can
Recycling.
2, the tertiary amines CO being prepared using the method for the present invention2/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, the bis- dodecyl second of N '-two (N, N- dimethyl propylamine)-N, N '-
Diamines is being passed through CO2There is preferable surface-active later.
3, the bis- dodecyl ethylenediamines of N, N '-two (N, N- dimethyl propylamine)-N, N '-and CO2Reaction generates N, N '-two
The bicarbonate cationic complex of the bis- dodecyl ethylenediamines of (N, N- dimethyl propylamine)-N, N '-, conductivity are 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 the N that the present invention is prepared, N '-two (N, N- dimethyl propylamine)-N,
The CO of the bis- dodecyl ethylenediamines of N '-2Responsiveness, i.e. CO2Switch property.
4, in closed pressure vessel, with the increase of carbon dioxide intake, container inner pressure is also increased with it, dioxy
Change the meltage of carbon in water also to increase, increases 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.
Detailed description of the invention
Fig. 1 is to be passed through excessive CO2Afterwards, the relation curve of surface tension and target product concentration；
Fig. 2 is under 0.2% target product concentration conditions, and surface tension is with injection CO2The change curve of volume；
Fig. 3 be under 0.2% target product concentration conditions, conductivity with duration of ventilation variation rule curve；
Fig. 4 is alternately to lead to CO three times respectively in same solution2And N2Reversible transition is carried out, when forming surfactant,
Each foam volume is measured with the change curve of target product surface surfactant concentration.
Specific embodiment
A specific embodiment of the invention is described below, in order to facilitate understanding by those skilled in the art this hair
It is bright, it should be apparent that the present invention is not limited to the ranges of specific embodiment, for those skilled in the art,
As long as various change is in the spirit and scope of the present invention that the attached claims limit and determine, these variations are aobvious and easy
See, all are using the innovation and creation of present inventive concept in the column of protection.
Embodiment 1
A kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, comprising the following steps:
(1) 0.045mol ethylenediamine is dissolved in 20mL dehydrated alcohol, heating water bath to 70 DEG C, then be added dropwise thereto dissolved with
The ethanol solution of the bromododecane of 0.1mol, control are 1.5h dissolved with the time for adding of the ethanol solution of bromododecane, are stirred
It mixes for 24 hours, obtains reaction solution I；
(2) it pours out reaction solution I while hot after reaction, cools down at room temperature, filter, washed filter cake 3 times with dehydrated alcohol,
It is dried under conditions of 50 DEG C, obtains white solid powder N, the bis- dodecyl ethylenediamines of N '-；
(3) step (2) obtained solid powder is dissolved in dehydrated alcohol, oil bath heating is to 80 DEG C, then is added dropwise thereto
Respectively dissolved with the N of 0.022mol, the ethanol solution of the potassium iodide of N- dimethyl -3- chlorine propylamine and 0.022mol, control is molten respectively
There is a N, the time for adding of the ethanol solution of N- dimethyl -3- chlorine propylamine and potassium iodide is 4h, after stirring for 24 hours, obtains reaction solution II；
(4) it pours out reaction solution II while hot after reaction, cools down at room temperature, washed 3 times with dehydrated alcohol, then at 50 DEG C
Under conditions of dry, obtain target product N, bis- dodecyl ethylenediamines of N '-two (N, N- dimethyl propylamine)-N, N '-, 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 realize surface-active at non-surface-active agent
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, comprising the following steps:
(1) ethylenediamine is dissolved in dehydrated alcohol, heating water bath is to 65 DEG C, then the bromo dissolved with 0.5mol is added thereto
The ethanol solution of dodecane, control are 1h dissolved with the time for adding of the ethanol solution of bromododecane, stir 20h, obtain reaction solution
Ⅰ；Wherein, the w/v of ethylenediamine and dehydrated alcohol is 4:22；The molar ratio of ethylenediamine and bromododecane is 5:18；
(2) it pours out reaction solution I while hot after reaction, cools down at room temperature, filter, washed filter cake 4 times with dehydrated alcohol,
It is dried under conditions of 60 DEG C, obtains white solid powder N, the bis- dodecyl ethylenediamines of N '-；
(3) step (2) obtained solid powder is dissolved in dehydrated alcohol, oil bath heating is to 75 DEG C, then is added dropwise thereto
Respectively dissolved with the N of 0.05mol, the ethanol solution of the potassium iodide of N- dimethyl -3- chlorine propylamine and 0.05mol, control respectively dissolved with
The time for adding of N, N- dimethyl -3- chlorine propylamine and the ethanol solution of potassium iodide is 4h, after stirring 20h, obtains reaction solution II；
(4) it pours out reaction solution II while hot after reaction, cools down at room temperature, washed 3 times with dehydrated alcohol, then at 62 DEG C
Under conditions of dry, obtain N, bis- dodecyl ethylenediamines of N '-two (N, N- dimethyl propylamine)-N, N '-, then the target of 0.5g is produced
Object 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 at 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, comprising the following steps:
(1) ethylenediamine is dissolved in dehydrated alcohol, heating water bath is to 60 DEG C, then the bromo dissolved with 0.25mol is added thereto
The ethanol solution of dodecane, control are 2h dissolved with the time for adding of the ethanol solution of bromododecane, and stirring for 24 hours, obtains reaction solution
Ⅰ；Wherein, the w/v of ethylenediamine and dehydrated alcohol is 2:20；The molar ratio of ethylenediamine and bromododecane is 7:19；
(2) it pours out reaction solution I while hot after reaction, cools down at room temperature, filter, washed filter cake 3 times with dehydrated alcohol,
It is dried under conditions of 62 DEG C, obtains white solid powder N, the bis- dodecyl ethylenediamines of N '-；
(3) step (2) obtained solid powder is dissolved in dehydrated alcohol, oil bath heating is to 76 DEG C, then is added dropwise thereto
Respectively dissolved with the N of 0.042mol, the ethanol solution of the potassium iodide of N- dimethyl -3- chlorine propylamine and 0.042mol, control is molten respectively
There is a N, the time for adding of the ethanol solution of N- dimethyl -3- chlorine propylamine and potassium iodide is 3h, after stirring for 24 hours, obtains reaction solution II；
(4) it pours out reaction solution II while hot after reaction, cools down at room temperature, washed 3 times with dehydrated alcohol, then at 60 DEG C
Under conditions of dry, obtain N, bis- dodecyl ethylenediamines of N '-two (N, N- dimethyl propylamine)-N, N '-, then the target of 0.1g is produced
Object is added in closed pressure vessel, adds 100ml water, is passed through 200ml CO2Obtain tertiary amines CO2/N2Switching mode Gemini table
Face activating agent, then it is passed through 200ml N2So that surfactant transitions realize surfactant and non-table at non-surface-active agent
Phase co-conversion between the activating agent of face.
Experimental example
To 1 gained tertiary amines CO of embodiment2/N2Switching mode Gemini surface active carries out mapping surface properties, surface
Power detection, foaming properties invertibity and the detection of conductivity invertibity.
Surface tension detection: the measuring method of surface tension mainly has capillary rise method, hanging ring method, sessile drop method and bubble
Maximum pressure method etc., experiment use JK99B Full-automatic tension instrument, measure product surface by hanging ring method；Configure series of concentrations
Solution (aqueous surfactant solution of 0.1wt%, 0.2wt%, 0.3wt%, 0.4wt% and 0.5wt%), 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 graph, it is computed and Linear Quasi
It closes, other important properties parameters of surfactant, pC can be acquired20、ΓmaxAnd Amin。
ΓmaxIndicate that surfactant molecule in the saturated extent of adsorption of liquid-vapor interface, is inhaled according to formula (1) Gibbs isothermal
Attached equation calculation.Wherein d γ/dlogC is the slope of γ-logC straight line portion；Wherein T (K) is test temperature, and R is that gas is normal
Number (8.314J/molK), n takes 2.
AminWhen indicating 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.It can be according to ΓmaxIt is calculated by formula (2), wherein NAFor Avgadro constant
(6.02×1023mol-1)。
pC20Indicate the efficiency of surfactant, C20For the surface tension of pure water is reduced 20mNm-1Required surface
Surfactant concentration, C20Negative logarithm, that is, pC20(pC20=-logC20), for measuring surfactant molecule in the poly- of gas-liquid interface
Collect efficiency, pC20Value is bigger, and surfactant molecule more tends to more tend to form micella in adsorption at gas-liquid surface, reduces surface
The efficiency of power is higher, pC20It can be acquired 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。
Resulting surface tension (γ)-log concentration (logC) curve such as Fig. 1, in closed pressure vessel, surface tension
With being passed through CO2The curve of volume change such as Fig. 2, the critical micell that can release surfactant by the catastrophe point of Fig. 1 curve are dense
It spends (CMC), corresponding surface tension is γcmc, the result is shown in tables 1.
1 critical micelle concentration of table (CMC) and γcmc
Surface performance is detected using conventional method, testing result is shown in Table 2.
2 surface performance parameter of table
The detection of conductivity invertibity: 0.01mol/L N, the bis- dodecanes of N '-two (N, N- dimethyl propylamine)-N, N '-are prepared
The solution of base ethylenediamine tests its initial conductivity value, and in 25 DEG C of closed pressure vessel with the rate of 10mL/min
CO is passed through into solution2Gas surveys a conductivity every 5min, and when the reaction in system reaches balance, conductivity value tends to
Gently；N is passed through into system with the rate of 10mL/min again2, recording solution conductivity value, when the conductivity of system tends to again
Gently, it is reduced to a minimum value, stops ventilation；Repetition is real three times, the conductivity versus time curve of surfactant
As shown in Figure 3.
Foaming properties invertibity detection: by product be made into various concentration surfactant solution (0.1wt%,
0.2wt%, 0.3wt%, 0.4wt%, 0.5wt%, 0.6wt%), after the solution foaming of configured surfactant, base
This non-foam generates, and is then passed through CO thereto2, then the graduated cylinder that 1000mL is immediately transferred into after rotation 60s is poured into blistering instrument
In, there are a large amount of foams to generate at this time, after foam completely disappears, N is passed through into solution2, then pour into blistering instrument after rotation 60s
It is immediately transferred into the graduated cylinder of 1000mL, it can be found that basic non-foam generates in graduated cylinder, experiment is repeated three times, as a result such as Fig. 4
It is shown.
Conclusion
1, 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.
2, figure it is seen that not being passed through CO2When, surface tension is basic and water is consistent, with
CO2Intake increase, surface tension is reduced rapidly, be passed through 200mL rear surface tension and reduce amplitude and slow down, until
400mL is later substantially unchanged, illustrates that transformation of the non-surface-active agent to surfactant at this time has been basically completed.
3, 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/N2The surface of switching mode Gemini surface active is living
Property parameter is more preferable.
4, from figure 3, it can be seen that the conductivity value of solution original state is slightly above zero, with CO2It is constantly passed through, N,
The bis- dodecyl ethylenediamines of N '-two (N, N- dimethyl propylamine)-N, N '-and CO2Reaction generates N, (N, the N- dimethyl propylene of N '-two
Amine)-N, the bicarbonate complex compound (quaternary surfactant completely dissociates into) of the bis- dodecyl ethylenediamines of N '-, conductivity is fast
Speed rises, and reaches maximum value in 80min or so conductivity and keeps balancing, and shows that surfactant transitions efficiency is maximum at this time,
It is subsequently passed N2, bicarbonate complex compound is decomposed into original state again, becomes neutral non-ionic compound, at this time in solution
Conductivity declines rapidly, is gradually recovered into initial value, repeats the CO that experiment confirms the surfactant of synthesis by conductivity2
Responsiveness, i.e. CO2Switch property.
5, as can be seen from Figure 4 with the increase of surfactant concentration, system foam volume increases, when concentration reaches one
Surfactant concentration is continued growing after definite value, foam volume variation is smaller, gradually tends to be steady, and maximum foam volume is
650mL。
6, the N that the present invention is prepared, the bis- dodecyl ethylenediamines of N '-two (N, N- dimethyl propylamine)-N, N '-can be with two
Carbonoxide forms ionic complex, can be used as CO2/N2Surfactant, while there is CO2Switch invertibity.
Claims (6)
1. a kind of tertiary amines CO2/N2The synthetic method of switching mode Gemini surface active, which is characterized in that including following step
It is rapid:
(1) ethylenediamine is dissolved in dehydrated alcohol, heating water bath adds the bromo ten dissolved with 0.1~0.5mol to 65~70 DEG C
The ethanol solution of dioxane, stirring 20~for 24 hours, obtain reaction solution I；Wherein, the w/v of ethylenediamine and dehydrated alcohol is 2~4:
20~22；The molar ratio of bromododecane and ethylenediamine is 18~20:5~9；
(2) reaction solution I is cooled down at room temperature, and filtering is washed filter cake 3~5 times with dehydrated alcohol, is dried, is obtained then at 50~62 DEG C
N, N '-bis- dodecyl ethylenediamines；
(3) step (2) gains are dissolved in dehydrated 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 potassium iodide, stirring 20~for 24 hours, obtain reaction solution II；Wherein, N, N- dimethyl -3- chlorine
The molar ratio of propylamine and potassium iodide is 1:1；
(4) reaction solution II is cooled down at room temperature, is washed 3~5 times with dehydrated alcohol, is dried then at 50~62 DEG C, is obtained target product
The bis- dodecyl ethylenediamines of N, N '-two (N, N- dimethyl propylamine)-N, N '-, are added into closed pressure vessel, add 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, feature exist
In bath temperature described in step (1) is 70 DEG C, and the molar 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, feature exist
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, feature exist
In the w/v of ethylenediamine described in step (1) and dehydrated alcohol is 2.7:20.
5. tertiary amines CO according to claim 12/N2The synthetic method of switching mode Gemini surface active, feature exist
In oil bath temperature described in step (3) is 80 DEG C, N, N- dimethyl -3- chlorine propylamine, potassium iodide and the bis- dodecyl second of N, N ' -
The molar 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, feature exist
In being added dropwise respectively in step (3) dissolved with N, when the ethanol solution of N- dimethyl -3- chlorine propylamine and potassium iodide, time for adding is controlled
System is in 3~4h.
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