CN105879772B - One class has the trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation - Google Patents
One class has the trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation Download PDFInfo
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Abstract
There is the trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation, wherein trimerization anion surface active agent C TrisPhC the present invention relates to a classnNa (n=10,12,14) molecular structure is as follows：R=CnH2n+1(n=10,12,14) such trimerization anion surface active agent can form viscoelastic solution in the case of not against any additive.C‑TrisPhCnNa hydrophobic chain length is longer, and the viscoplasticity for forming solution is better.It is only 65mmolL in surfactant concentration‑1When, C TrisPhC14The zero-shear viscosity of Na solution is up to 1380Pas.It is used as an analog anion surfactants, C TrisPhCnNa has good biocompatibility, and the viscoelastic solution formed can be applied in oil field fracturing fluid, towing drag reducer and daily cleaning agent prescription.
Description
Technical field
The present invention relates to a class trimerization anion surface active agent and its viscoelastic solution of formation, more particularly to one kind contains
The trimerization anion surface active agent of long rigid attachment base and its viscoelastic solution of formation, belong to surfactant scientific domain.
Background technology
Surfactant viscoelastic solution has a wide range of applications in daily life and industrial production, as oil field is adopted
The fracturing fluid used in oil, pulls drag reducer and daily cleaning agent prescription etc..Common surfactant viscoelastic solution system can
It is divided into surfactant/salt system or mixed surfactant system.However, this kind of system usually requires higher surface-active
Agent concentration, this make it that the application cost of surfactant viscoelastic solution is higher.Simultaneously as this kind of viscoelastic solution is by various ingredients
Compounding is formed, and (such as rock stratum or soil) makes in use, chromatographic fractionation effect can be produced in some systems with complicated interface
Obtain mixed solution and lose viscoplasticity, reduce its application performance.On the other hand, unnecessary pollution can be also caused to system, is increased
The difficulty of post processing is added.
The viscoplasticity of surfactant solution and the molecular structure of surfactant are closely related.Oligo surfactant contains
There is different kinds of molecules structural element, asymmetric aggregated structure such as rod-shaped micelle or worm glue can be self-assembly of under low concentration
Beam etc., makes solutions display go out very strong viscoplasticity, and the broad interest of people is caused in recent years.Spacer group is lived to oligomeric surface
The self-organizing behavioral implications of property agent is notable.If suitable spacer group can be selected, the molecule of oligo surfactant is rationally designed
Structure, then be expected to the effect not against any additive, and obtaining has high viscoelastic surfactant solution system.
The content of the invention
In order to overcome the defect that current surfactant viscoelastic solution exists in application aspect, the present invention utilizes 1,1,1- tri-
The molecular characterization of (4- hydroxyphenyls) ethane, as the long rigid attachment group of terpolymer surfactant, has synthesized one
Class can form the trimerization anion surface active agent of viscoelastic solution without any additive.
The technical scheme is that：With 1,1,1- tri- (4- hydroxyphenyls) ethane for spacer group, one class trimerization of synthesis is cloudy
Ionic surface active agent C-TrisPhCnNa (n is the carbon number contained by surfactant hydrophobic alkane chain).Again by the surface
Activating agent is dissolved in water, forms viscoelastic solution.Wherein trimerization anion surface active agent C-TrisPhCnNa structural formula is as follows：
Trimerization anion surface active agent C-TrisPhCnNa (n=10,12,14) synthetic route is as follows：
By a certain amount of trimerization anion surface active agent C-TrisPhCnNa (n=10,12,14) is dissolved in water, you can obtain
Obtain corresponding surfactant viscoelastic solution.
Beneficial effect
Trimerization anion surface active agent containing long rigid attachment base, in the case of not against any additive
Being formed has good viscoelastic solution.It can reduce use cost, eliminate the defects such as chromatographic fractionation effect in use.It can apply
In oil field fracturing fluid, in the formula of towing drag reducer or daily cleaning agent.
Brief description of the drawings
Fig. 1 C-TrisPhC10Na nuclear magnetic spectrogram (being measured in MeOD).
Fig. 2 C-TrisPhC12Na nuclear magnetic spectrogram (being measured in MeOD).
Fig. 3 C-TrisPhC14Na nuclear magnetic spectrogram (being measured in MeOD).
C-TrisPhC under Fig. 4 various concentrations10The viscosity of Na solution with shear rate change curve.
C-TrisPhC under Fig. 5 various concentrations12The viscosity of Na solution with shear rate change curve.
C-TrisPhC under Fig. 6 various concentrations14The viscosity of Na solution with shear rate change curve.
Fig. 7 trimerization anion surface active agents (C-TrisPhCnNa, n=10,12,14) solution zero-shear viscosity with dense
The change curve of degree.
Embodiment
Embodiment 1:The synthesis of alpha-brominated methyl dodecanoate.Lauric acid/dodecanoic acid (68.8g, 0.4mol) is added into 500mL there-necked flasks
In, melted at 65 DEG C, thionyl chloride (67.6g, 0.56mol) be slowly added dropwise under stirring, drips and temperature is increased to 90 DEG C,
A little elemental iodine is added as initiator, is slowly added dropwise through the dried bromine of the concentrated sulfuric acid (73.6g, 0.46mol), is stirred at reflux
12 hours, 65 DEG C are cooled the temperature to, stirring is lower to be added dropwise absolute methanol 60mL, is flowed back 2-4 hours after adding.3- is washed with water after cooling
4 times, then organic layer is washed to neutrality with saturated sodium bisulfite solution 50mL, finally it is washed with water 3-4 times.Organic layer adds anhydrous
Magnesium sulfate is dried overnight.After filtering, crude product vacuum distillation is obtained into alpha-brominated methyl dodecanoate.154~158 DEG C/5mmHg.
Embodiment 2:The synthesis of alpha-brominated methyl myristate.Tetradecylic acid (150g, 0.6568mol) is added into tri- mouthfuls of 500mL
In bottle, melt at 65 DEG C, thionyl chloride (106.6g, 0.821mol) is slowly added dropwise under stirring, drips and is increased to temperature
90 DEG C, a little elemental iodine is added as initiator, is slowly added dropwise through the dried bromine of the concentrated sulfuric acid (131.2g, 0.821mol),
It is stirred at reflux 12 hours, cools the temperature to 65 DEG C, stirring is lower is added dropwise absolute methanol 120mL, is flowed back 2-4 hours after adding.Cooling
After be washed with water 3-4 times, then wash organic layer to neutrality with saturated sodium bisulfite solution 50mL, be finally washed with water 3-4 times.It is organic
Layer adds anhydrous magnesium sulfate and is dried overnight.After filtering, crude product vacuum distillation is obtained into alpha-brominated methyl myristate.175~180 DEG C/
5mmHg。
Embodiment 3:The synthesis of alpha-brominated methyl palmitate.Hexadecylic acid (150g, 0.58mol) is added into 500mL there-necked flasks
In, melt at 65 DEG C, thionyl chloride (95.1g, 0.73mol) be slowly added dropwise under stirring, drips and temperature is increased to 90 DEG C,
A little elemental iodine is added as initiator, is slowly added dropwise through the dried bromine of the concentrated sulfuric acid (116.6g, 0.73mol), stirs back
Stream 12 hours, cools the temperature to 65 DEG C, and stirring is lower to be added dropwise absolute methanol 80mL, is flowed back 2-4 hours after adding.It is washed with water after cooling
3-4 times, then organic layer is washed to neutrality with saturated sodium bisulfite solution 50mL, finally it is washed with water 3-4 times.Organic layer adds nothing
Water magnesium sulfate is dried overnight.After filtering, crude product vacuum distillation is obtained into alpha-brominated methyl palmitate.192~196 DEG C/5mmHg.
Embodiment 4:C-TrisPhC10Na synthesis.By 1,1,1- tri- (4- hydroxyphenyls) ethane (8.1g, 0.026mol), warp
The DMF (100mL) that molecular sieve after activation is treated is added in 500mL three-necked bottle, and nitrogen atmosphere is prevented
Phenolic hydroxyl group is aoxidized.Anhydrous potassium carbonate (28g, 0.207mol) is added, 60 DEG C is warming up to, disposably adds alpha-brominated methyl dodecanoate
(31.2g, 0.104mol) (is dissolved in 40mL DMF), and 85 DEG C are warming up to after 2h, is reacted 24 hours.It is cold
But suction filtration obtains yellow filtrate after, by the DMF removed under reduced pressure in filtrate.Filtrate is transferred in separatory funnel,
First plus 60mL petroleum ethers, 80mL frozen water washing organic layer is added 3-4 times.Organic layer is separated, anhydrous magnesium sulfate is added and dries,
Removed under reduced pressure petroleum ether after filtering.Residue is used column chromatography, and eluant, eluent starts to use petroleum ether, and petroleum ether and acetic acid are used later
(volume ratio is 10 to the mixed liquor of ethyl ester:1).Obtain light yellow viscous liquid.Yield is 70.8%.By this liquid (13g,
0.014mol), sodium hydroxide (1.9g, 0.046mol) and 100mL absolute ethyl alcohols add the single-necked flask equipped with reflux condensing tube
In.Temperature is raised into 85 DEG C of backflows to stay overnight.Reactant mixture is centrifuged into obtain white precipitate.Precipitation is washed four times with absolute ethyl alcohol,
Dry the final product C-TrisPhC in vacuum drying chamber10Na.Yield is 75.6%.
Embodiment 5:C-TrisPhC12Na synthesis.By 1,1,1- tri- (4- hydroxyphenyls) ethane (8.5g, 0.028mol), warp
The DMF (100mL) that molecular sieve after activation is treated is added in 500mL three-necked bottle, and nitrogen atmosphere is prevented
Phenolic hydroxyl group is aoxidized.Anhydrous potassium carbonate (28g, 0.207mol) is added, 60 DEG C is warming up to, disposably adds alpha-brominated methyl myristate
(17.8g, 0.056mol) (is dissolved in 45mL DMF), and 85 DEG C are warming up to after 2h, is reacted 24 hours.It is cold
But suction filtration obtains yellow filtrate after, by the DMF removed under reduced pressure in filtrate.Filtrate is transferred in separatory funnel,
First plus 60mL petroleum ethers, 80mL frozen water washing organic layer is added 3-4 times.Organic layer is separated, anhydrous magnesium sulfate is added and dries,
Removed under reduced pressure petroleum ether after filtering.Residue is used column chromatography, and eluant, eluent starts to use petroleum ether, and petroleum ether and acetic acid are used later
(volume ratio is 10 to the mixed liquor of ethyl ester:1).Obtain light yellow viscous liquid.Yield is 75.4%.By this liquid (23g,
0.022mol), sodium hydroxide (2.95g, 0.074mol) and 100mL absolute ethyl alcohols add the single-necked flask equipped with reflux condensing tube
In.Temperature is raised into 85 DEG C of backflows to stay overnight.Reactant mixture is centrifuged into obtain white precipitate.Precipitation is washed four times with absolute ethyl alcohol,
Dry the final product C-TrisPhC in vacuum drying chamber12Na.Yield is 77.9%.
Embodiment 6:C-TrisPhC14Na synthesis.By 1,1,1- tri- (4- hydroxyphenyls) ethane (8.4g, 0.027mol), warp
The DMF (100mL) that molecular sieve after activation is treated is added in 500mL three-necked bottle, and nitrogen atmosphere is prevented
Phenol is aoxidized.Anhydrous potassium carbonate (28g, 0.207mol) is added, 60 DEG C is warming up to, disposably adds alpha-brominated methyl palmitate
(38.3g, 0.100mol) (is dissolved in 60mL DMF), and 85 DEG C are warming up to after 2h, is reacted 24 hours.It is cold
But suction filtration obtains yellow filtrate after, by the DMF removed under reduced pressure in filtrate.Filtrate is transferred in separatory funnel,
First plus 60mL petroleum ethers, 80mL frozen water washing organic layer is added 3-4 times.Organic layer is separated, anhydrous magnesium sulfate is added and dries,
Removed under reduced pressure petroleum ether after filtering.Residue is used column chromatography, and eluant, eluent starts to use petroleum ether, and petroleum ether and acetic acid are used later
(volume ratio is 10 to the mixed liquor of ethyl ester:1).Obtain light yellow viscous liquid.Yield is 71.7%.By this liquid (25.9g,
0.023mol), sodium hydroxide (3.075g, 0.077mol) and 100mL absolute ethyl alcohols add the single port equipped with reflux condensing tube and burnt
In bottle.Temperature is raised into 85 DEG C of backflows to stay overnight.Reactant mixture is centrifuged into obtain white precipitate.Precipitation washs four with absolute ethyl alcohol
It is secondary, obtain final product C-TrisPhC after being dried in vacuum drying chamber14Na.Yield is 80.6%.
Embodiment 7:The preparation of surfactant solution.A certain amount of C-TrisPhC is weighed respectively10Na、C-
TrisPhC12Na and C-TrisPhC14Na solids, are dissolved in the water of certain volume, that is, obtain series of surfactants solution.
Embodiment 8:Trimerization anion surface active agent C-TrisPhCnThe viscoplasticity of Na (n=10,12,14) solution is surveyed
Amount.Series of surfactants solution is stood into 48h at 25 DEG C, and carries out at 25 DEG C the test of stable state rheological property.As a result
As shown in Figure 4, Figure 5 and Figure 6.After finite concentration, surfactant solution shows shear thinning phenomenon, illustrates with bright
Aobvious viscoplasticity.Fig. 7 is the zero-shear viscosity (η of three systems0) with the change of concentration.Hydrophobic tail chain is longer, zero-shear viscosity
It is rapider with the increase of concentration.C-TrisPhC12Na and C-TrisPhC14There is maximum on curve in Na solution, and this is due to
In solution caused by the change of micro-structural.
Claims (4)
1. a class has the trimerization anion surface active agent of long rigid attachment base, its molecular structure is as follows：
2. the trimerization anion surface active agent with long rigid attachment base described in a class claim 1, it is characterised in that be
Reaction is obtained as the following formula：
3. a class surfactant viscoelastic solution, is trimerization the moon that the class described in claim 1 is had into long rigid attachment base
Ionic surface active agent is dissolved in water and obtained, it is characterised in that as surfactant hydrophobic tail chain institute carbon atom quantity n=10,
The concentration range for forming viscoelastic solution is 100-250mmolL-1；As surfactant hydrophobic tail chain institute carbon atom quantity n=12
When, the concentration range for forming viscoelastic solution is 60-200mmolL-1；As surfactant hydrophobic tail chain institute carbon atom quantity n=
When 14, the concentration range for forming viscoelastic solution is 40-100mmolL-1。
4. the surfactant viscoelastic solution described in a class claim 3, it is characterised in that such surfactant formation viscoelastic
Any additive is not needed during solution.
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