CN111468032B - A kind of easily soluble/cleavable/self-thickening surfactant and preparation method - Google Patents
A kind of easily soluble/cleavable/self-thickening surfactant and preparation method Download PDFInfo
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Abstract
The invention discloses a soluble/cleavable/self-thickening surfactant and a preparation method thereof, wherein the soluble/cleavable/self-thickening surfactant is obtained by mixing alkyl alcohol phthalate monoester and alkali at room temperature in an equimolar manner, stirring and reacting for 0.5-4 h, and removing a solvent. The easily soluble/cleavable/self-thickening surfactant can be quickly dissolved at a reduced temperature, has strong self-assembly capability, can realize the thickening of an aqueous solution at a lower concentration, and shows stronger salt resistance than the traditional carboxylate surfactant.
Description
Technical Field
The invention belongs to the technical field of surfactants and viscoelastic fluids, and particularly relates to a soluble/cleavable/self-thickening surfactant and a preparation method thereof.
Background
The surfactant is an amphiphilic molecule consisting of a hydrophilic head group and a hydrophobic tail chain, can be self-assembled in an aqueous solution to form various aggregate structures, shows unique physical and chemical properties, and is widely applied to various fields of washing, food, medicines, coatings, textiles, buildings, oil extraction and the like.
The surfactant with a specific structure can thicken an aqueous solution to form a viscoelastic fluid similar to a polymer solution under a certain condition, and can be used as a clean fracturing fluid for increasing the yield of an oil-gas field, a transportation carrier of a functional component or tackifying a product. Most of the viscoelastic fluids at present are cationic surfactants (CN10395199A, CN102643637A, CN103897684A, CN101298555A, CN101481608A) or zwitterionic surfactants (CN101812290A, CN103951593A, CN104073235A, CN 102851017). Also, to achieve viscosification of the aqueous solution, it is often necessary to introduce components other than surfactants to aid in the dissolution of the surfactants or to promote the formation of viscoelastic fluids. This adds virtually to the complexity of the system. In addition, cationic surfactants have higher toxicity and irritation, and are more difficult to biodegrade than anionic surfactants. The process of making zwitterionic surfactants is often more complicated than anionic surfactants, especially relative to fatty acid salt anionic surfactants, resulting in increased costs for viscoelastic fluids.
Therefore, there is a need in the art for an anionic surfactant that combines the properties of being readily soluble, cleavable, and self-thickening.
Disclosure of Invention
This section is for the purpose of summarizing some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. In this section, as well as in the abstract and the title of the invention of this application, simplifications or omissions may be made to avoid obscuring the purpose of the section, the abstract and the title, and such simplifications or omissions are not intended to limit the scope of the invention.
The present invention has been made keeping in mind the above and/or other problems occurring in the prior art.
It is therefore an object of the present invention to overcome the deficiencies of the prior art and to provide a readily soluble/cleavable/self-thickening surfactant.
In order to solve the technical problems, the invention provides the following technical scheme: a lyotropic/cleavable/self-thickening surfactant, said surfactant having the formula (1):
r is any one of saturated or unsaturated alkyl with 18-24 carbon atoms;
m is an organic cation including hydroxyethyl trimethyl quaternary ammonium cation, tetramethyl quaternary ammonium cation or benzyl trimethyl quaternary ammonium cation.
As a preferable embodiment of the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the lyotropic/cleavable/self-thickening surfactant has a krafft temperature of less than 35 ℃.
As a preferable embodiment of the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the easily soluble/cleavable/self-thickening surfactant can remarkably increase the viscoelasticity of an aqueous solution after being dissolved in water to form a viscoelastic fluid without any additive.
As a preferable embodiment of the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the concentration of the lyotropic/cleavable/self-thickening surfactant in the viscoelastic fluid should be greater than 10 times the critical micelle concentration of the surfactant.
As a preferable embodiment of the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the lyotropic/cleavable/self-thickening surfactant, rapidly cleaves at a pH greater than 12.
It is a further object of the present invention to overcome the deficiencies of the prior art and to provide a process for the preparation of a readily soluble/cleavable/self-thickening surfactant.
In order to solve the technical problems, the invention provides the following technical scheme: a method for preparing a surfactant comprises,
preparation of alkyl alcohol phthalic acid monoester: according to a molar ratio of 0.8-1.2: 1, reacting for 0.5-5 h at 90-150 ℃ under the solvent-free condition to obtain the alkyl alcohol phthalic monoester, wherein the structural formula of the alkyl alcohol phthalic monoester is shown as a formula (2):
wherein R is any one of saturated or unsaturated alkyl with 18-24 carbon atoms;
preparation of alkyl alcohol phthalate monoester salt: and (3) mixing the alkyl alcohol phthalic acid monoester and alkali at the room temperature in an equimolar manner, stirring for reacting for 0.5-4 h, and removing the solvent to obtain the easily-soluble/cleavable/self-thickening surfactant.
As a preferable embodiment of the method for preparing the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the alkyl alcohol comprises one of stearyl alcohol, oleyl alcohol, arachidyl enol, behenyl alcohol, erucyl alcohol and sterol.
As a preferable embodiment of the method for preparing the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the alkali comprises one of sodium hydroxide, potassium hydroxide, choline hydroxide, tetramethylammonium hydroxide and benzyltrimethylammonium hydroxide.
As a preferable embodiment of the method for preparing the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the preparation method is used for preparing the alkyl alcohol phthalic acid monoester, wherein the molar ratio of alkyl alcohol to phthalic anhydride is 1:1, the reaction temperature is 95-140 ℃, and the reaction time is 1-4 h.
As a preferable embodiment of the method for preparing the easily soluble/cleavable/self-thickening surfactant of the present invention, wherein: the alkyl alcohol phthalic monoester salt is prepared, wherein the stirring reaction time is 0.5-3 h.
The invention has the beneficial effects that:
(1) the easily soluble/cleavable/self-thickening surfactant can be quickly dissolved at a lower temperature, does not need any cosolvent, is convenient to prepare on site, and is simple to operate. The easily-soluble/cleavable/self-thickening surfactant can be quickly dissolved at a reduced temperature, has strong self-assembly capability, can realize the thickening of an aqueous solution at a lower concentration, shows stronger salt resistance than the traditional carboxylate surfactant, has strong self-assembly capability, and has the critical micelle concentration which is 1-2 orders of magnitude lower than that of the surfactant with the same hydrophobic tail chain but without a benzene ring structure.
(2) Compared with the traditional anionic surfactant, the easily-soluble/cleavable/self-thickening surfactant prepared by the invention has stronger self-assembly capability, and can realize the thickening of aqueous solution without any additive; and can rapidly crack at a pH greater than 12, reducing the viscosity of the viscoelastic fluid formed.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, specific embodiments thereof are described in detail below with reference to examples of the specification.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
Furthermore, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
The chemical reaction equation of the easy-soluble/cleavable/self-thickening surfactant is as follows:
r is any one of saturated or unsaturated alkyl with 18-24 carbon atoms;
m is an organic cation including hydroxyethyl trimethyl quaternary ammonium cation, tetramethyl quaternary ammonium cation or benzyl trimethyl quaternary ammonium cation.
Example 1
10 mmol of mustard alcohol and 10 mmol of phthalic anhydride were added to the flask, heated to 100 ℃ and stirred for 1 hour under reflux. The product was transferred to petroleum ether and stirred, washed, filtered and dried under vacuum to give a white powder, the erucyl alcohol phthalate monoester, in a yield of 90% by high performance liquid chromatography.
3 millimoles of the erucamol phthalic acid monoester and 3 millimoles of the choline hydroxide are weighed and dissolved in water, stirred for 0.5 hour at room temperature, and the solvent is dried by spinning to obtain the erucamol phthalic acid monoester choline salt.
Example 2
10 mmol of behenyl alcohol and 10 mmol of phthalic anhydride were added to the flask, heated to 140 ℃, stirred, and reacted under reflux for 4 hours. Transferring the product into petroleum ether, stirring, washing, filtering, and vacuum drying to obtain white powder, i.e. behenyl alcohol phthalate monoester, with a yield of 92% by high performance liquid chromatography.
Weighing 3 millimoles of behenyl alcohol phthalic acid monoester and 3 millimoles of benzyl trimethyl ammonium hydroxide, dissolving in methanol, stirring for 1 hour at room temperature, and spin-drying the solvent to obtain the behenyl alcohol phthalic acid monoester benzyl trimethyl quaternary ammonium salt.
Example 3
10 mmol of arachidyl alcohol and 10 mmol of phthalic anhydride were added to a flask, heated to 120 ℃ and stirred to reflux for 2 hours. Transferring the product into petroleum ether, stirring, washing, filtering, and vacuum drying to obtain white powder, i.e. peanut enol phthalic monoester, with a yield of 96% by high performance liquid chromatography.
Weighing 3 mmol of peanut enol phthalic acid monoester and 3 mmol of tetramethylammonium hydroxide, dissolving in ethanol, stirring at room temperature for 1.5 hours, and spin-drying the solvent to obtain the peanut enol phthalic acid monoester tetramethylammonium salt.
Example 4
10 mmol of arachidyl alcohol and 10 mmol of phthalic anhydride were added to a flask, which was heated to 125 ℃ and then stirred and refluxed for 5 hours. Transferring the product into petroleum ether, stirring, washing, filtering, and vacuum drying to obtain white powder, i.e. peanut enol phthalic monoester, with yield of 95% by high performance liquid chromatography.
Weighing 3 mmol of peanut alcohol phthalic monoester and 3 mmol of tetramethylammonium hydroxide, dissolving in ethanol, stirring at room temperature for 2.5 hours, and spin-drying the solvent to obtain the peanut alcohol phthalic monoester tetramethylquaternary ammonium salt.
Example 5
10 mmol of sterol and 10 mmol of phthalic anhydride were charged into a flask, heated to 115 ℃ and stirred to reflux for 3 hours. Transferring the product into petroleum ether, stirring, washing, filtering, and vacuum drying to obtain white powder, i.e. sterol phthalic monoester, with yield of 95% by high performance liquid chromatography.
Weighing 3 mmol of sterol phthalic acid monoester and 3 mmol of benzyl trimethyl ammonium hydroxide, dissolving in methanol, stirring at room temperature for 2.5 hours, and spin-drying the solvent to obtain the sterol phthalic acid monoester benzyl trimethyl quaternary ammonium salt.
Example 6
10 mmol of stearyl alcohol and 10 mmol of phthalic anhydride were put into a flask, heated to 135 ℃ and stirred to reflux for 4 hours. The product was transferred to petroleum ether and stirred, washed, filtered and dried under vacuum to give a white powder, stearyl alcohol phthalate monoester, in a yield of 97% by high performance liquid chromatography.
3 millimole of stearyl alcohol phthalic monoester and 3 millimole of choline hydroxide are weighed and dissolved in methanol, stirred for 2.5 hours at room temperature, and the solvent is dried by spinning to obtain the stearyl alcohol phthalic monoester choline salt.
Example 7
10 mmol of oleyl alcohol and 10 mmol of phthalic anhydride were charged into a flask, heated to 95 ℃ and reacted under stirring and reflux for 4 hours. Transferring the product to petroleum ether, stirring, washing, filtering, and vacuum drying to obtain oleyl alcohol phthalate monoester with yield of 95% by high performance liquid chromatography.
Weighing 3 millimoles of oleyl phthalate monoester and 3 millimoles of benzyl trimethyl ammonium hydroxide, dissolving in ethanol, stirring for 3 hours at room temperature, and spin-drying the solvent to obtain the oleyl phthalate monoester benzyl trimethyl quaternary ammonium salt.
Example 8
(1) Surface properties of the lyotropic/cleavable/self-thickening surfactants:
the critical micelle concentration of the surfactant aqueous solution prepared in examples 1 to 7 at 35 ℃ was measured by a hanging piece method, and erucic acid choline salt, arachidonic acid tetramethyl quaternary ammonium salt, and oleic acid benzyl trimethyl quaternary ammonium salt were used as control samples. The results are shown in Table 1.
(2) Measurement of Krafft temperature
The respective Krafft temperatures of the surfactant aqueous solutions prepared in examples 1 to 7, which had a mass fraction of 1%, were measured by visual observation. And (3) heating the sample solution in a water bath until the solution is clear and transparent, then cooling until crystals are separated out from the solution, slowly heating until all the crystals in the solution are completely dissolved, wherein the corresponding temperature is the Krafft temperature, and repeatedly measuring for 3 times to obtain an average value. Sodium erucate, behenyl alcohol phthalic acid monoester sodium salt, arachidic acid tetramethyl quaternary ammonium salt, sodium stearate, stearic acid choline salt and stearyl alcohol phthalic acid monoester sodium salt are used as comparison samples. The results are shown in Table 1.
(3) Rheological properties of the lyotropic/cleavable/self-thickening surfactant viscoelastic fluid:
the surfactant prepared in examples 1 to 7 was formulated into an aqueous solution with a concentration of 50 mmol/l, allowed to stand at 35 ℃ for 48 hours, and then the shear rate of the solution was measured by a rotational rheometer to be 10s-1Apparent viscosity of the resulting mixture. Erucic acid choline salt, arachidonic acid tetramethyl quaternary ammonium salt and oleic acid benzyl trimethyl quaternary ammonium salt are used as comparison samples. The results are shown in Table 1.
(4) Salt tolerance of lyotropic/cleavable/self-thickening surfactant viscoelastic fluids:
the surfactant prepared in the examples 1 to 7 is prepared into an aqueous solution with the concentration of 50 millimoles per liter, the aqueous solution is kept stand at 35 ℃ for 48 hours, then sodium chloride is added into the sample respectively until the sample is clear and turbid, and the salt content in the sample is recorded. Erucic acid choline salt, arachidonic acid tetramethyl quaternary ammonium salt and oleic acid benzyl trimethyl quaternary ammonium salt are used as comparison samples. The results are shown in Table 1.
TABLE 1
As can be seen from Table 1, the surfactants prepared in examples 1-7 all have a low Krafft temperature, are very soluble, and are advantageous for on-site formulation. The introduction of the benzene ring structure does not result in the enhancement of the hydrophobicity of the surfactant, but instead, the enhancement of the hydrophilicity, which results in the significant decrease of the krafft temperature of the surfactant compared to the control.
The surfactants prepared in examples 1-7 all had very low critical micelle concentrations, indicating strong self-assembly capability. Compared with the surfactant with the same hydrophobic tail chain but without a benzene ring structure, the critical micelle concentration of the prepared surfactant is 1 to 2 orders of magnitude lower. It is demonstrated that the introduction of the benzene ring structure is more advantageous for the self-assembly of the surfactants prepared in examples 1-7.
The surfactants prepared in examples 1-7 have strong self-thickening ability. 50 mmol/l aqueous surfactant solution at a shear rate of 10s-1The apparent viscosity can reach more than 1000 mPas, especially the most prominent example 1-2, and the apparent viscosity exceeds 10000 mPas. In contrast, the apparent viscosity of the control sample was less than 100 mPas.
Meanwhile, the viscoelastic fluid prepared by the surfactants prepared in the embodiments 1 to 7 of the invention has better salt resistance.
The easily soluble/cleavable/self-thickening surfactant can be quickly dissolved at a lower temperature, does not need any cosolvent, is convenient to prepare on site, and is simple to operate.
Compared with the traditional anionic surfactant, the easily-soluble/cleavable/self-thickening surfactant prepared by the invention has stronger self-assembly capability, and can realize the thickening of an aqueous solution under the condition without any additive; and can rapidly crack at a pH greater than 12, reducing the viscosity of the viscoelastic fluid formed.
The easily soluble/cleavable/self-thickening surfactant can be quickly dissolved at a reduced temperature, has strong self-assembly capability, can realize the thickening of an aqueous solution at a lower concentration, and shows stronger salt resistance than the traditional carboxylate surfactant.
The invention provides an easily-soluble/cleavable/self-thickening surfactant, which is discovered by the inventor accidentally to have very good thickening capability, a traditional anionic surfactant thickening aqueous solution usually needs to be added with other auxiliary agents to reduce the dissolution temperature or promote the growth of micelles, the structure of the surfactant can realize low-temperature dissolution without any additive, and the thickening capability is remarkable.
It should be noted that the above-mentioned embodiments are only for illustrating the technical solutions of the present invention and not for limiting, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, which should be covered by the claims of the present invention.
Claims (10)
1. A readily soluble/cleavable/self-thickening surfactant characterized by: the structural formula of the surfactant is shown as a formula (1):
（1）
r is any one of saturated or unsaturated alkyl with 18-24 carbon atoms;
m is an organic cation including hydroxyethyl trimethyl quaternary ammonium cation, tetramethyl quaternary ammonium cation or benzyl trimethyl quaternary ammonium cation.
2. The lyotropic/cleavable/self-thickening surfactant of claim 1, wherein: the lyotropic/cleavable/self-thickening surfactant has a krafft temperature of less than 35 ℃.
3. The lyotropic/cleavable/self-thickening surfactant of claim 1, wherein: the easily soluble/cleavable/self-thickening surfactant can remarkably increase the viscoelasticity of an aqueous solution after being dissolved in water to form a viscoelastic fluid without any additive.
4. The lyotropic/cleavable/self-thickening surfactant of claim 3, wherein: the concentration of the lyotropic/cleavable/self-thickening surfactant in the viscoelastic fluid should be greater than 10 times the critical micelle concentration of the surfactant.
5. The lyotropic/cleavable/self-thickening surfactant of claim 1, wherein: the lyotropic/cleavable/self-thickening surfactant, rapidly cleaves at a pH greater than 12.
6. A process for preparing the lyotropic/cleavable/self-thickening surfactant according to any of claims 1 to 5, characterized in that: the preparation method of the surfactant comprises the following steps,
preparation of alkyl alcohol phthalic acid monoester: according to a molar ratio of 0.8-1.2: 1, reacting for 0.5-5 h at 90-150 ℃ under the solvent-free condition to obtain the alkyl alcohol phthalic monoester, wherein the structural formula of the alkyl alcohol phthalic monoester is shown as a formula (2):
（2）
wherein R is any one of saturated or unsaturated alkyl with 18-24 carbon atoms;
preparation of alkyl alcohol phthalate monoester salt: and (3) mixing the alkyl alcohol phthalic acid monoester and alkali at the room temperature in an equimolar manner, stirring for reacting for 0.5-4 h, and removing the solvent to obtain the easily-soluble/cleavable/self-thickening surfactant.
7. The process for preparing lyotropic/cleavable/self-thickening surfactants according to claim 6, characterized in that: the alkyl alcohol comprises one of stearyl alcohol, oleyl alcohol, arachidyl alcohol, behenyl alcohol and erucyl alcohol.
8. The process for preparing lyotropic/cleavable/self-thickening surfactants according to claim 6, characterized in that: the base comprises one of choline hydroxide, tetramethylammonium hydroxide and benzyltrimethylammonium hydroxide.
9. The process for preparing lyotropic/cleavable/self-thickening surfactants according to claim 6, characterized in that: the preparation method is used for preparing the alkyl alcohol phthalic acid monoester, wherein the molar ratio of alkyl alcohol to phthalic anhydride is 1:1, the reaction temperature is 95-140 ℃, and the reaction time is 1-4 h.
10. The process for preparing lyotropic/cleavable/self-thickening surfactants according to claim 6, characterized in that: the alkyl alcohol phthalic monoester salt is prepared, wherein the stirring reaction time is 0.5-3 h.
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| CN103272524A (en) * | 2013-06-21 | 2013-09-04 | 山东大学 | Preparation method for fluid of increasing viscoelasticity of anionic/cationic surfactant through polymer |
| CN109456194A (en) * | 2018-12-07 | 2019-03-12 | 浙江皇马新材料科技有限公司 | A kind of preparation method of fatty alcohol polyol acid esters |
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| CN109456194A (en) * | 2018-12-07 | 2019-03-12 | 浙江皇马新材料科技有限公司 | A kind of preparation method of fatty alcohol polyol acid esters |
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