CN112079762B - Surfactant with self-demulsification capability and preparation method and application thereof - Google Patents
Surfactant with self-demulsification capability and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a surfactant with self-demulsification capability, a preparation method and an application thereof, wherein the method comprises the following steps: 1) sequentially adding dodecylamine and cyclobut-3-ene dicarboxylic anhydride into a three-neck flask, introducing nitrogen, reacting for 2-5 h at 150-200 ℃, and performing nucleophilic addition-elimination reaction to generate imide; 2) diluting the reaction solution, slowly adding potassium permanganate at 0 ℃, heating to perform oxidation reaction to generate carboxyl, and reacting at 90-100 ℃ for 10-12 hours; and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate, filtering by adopting diatomite and extracting impurities by adopting ethyl acetate, collecting a water phase, adjusting the pH value to be 2-4 to separate out a product, and filtering and drying to constant weight to obtain a final product. The surfactant with self-demulsification capability is applied to thick oil emulsification to reduce the viscosity of the thick oil, the pH value of the emulsified thick oil is high before the emulsified thick oil enters oil refining, and the demulsification of the emulsified thick oil can be realized due to the hydrolytic inactivation of the surfactant.
Description
Technical Field
The invention belongs to the field of functional surfactants, and particularly relates to a surfactant with self-demulsification capability, and a preparation method and application thereof.
Background
The heavy oil is an important component of oil and gas resources, and the high-viscosity heavy oil resources are widely distributed. The higher viscosity of the coal restricts the flowability of the coal in the conveying process to a certain extent, and great difficulty is brought to the mining process. In order to reduce the viscosity of the thick oil in the shaft and the gathering and transportation pipeline and solve the problem of thick oil layer and shaft thick oil blockage, a technology of emulsifying the thick oil by a surfactant to reduce the viscosity of the thick oil is often adopted in development and production to increase the fluidity of the crude oil, so as to improve the thick oil recovery efficiency and ensure the smooth thick oil recovery. Before the crude oil is refined, the emulsified thick oil needs to be demulsified to remove water in the thick oil. At present, various demulsifiers are added to realize oil-water separation of emulsified thick oil, but the effect is not obvious, and a flexible and efficient method for realizing the synergistic operation of thick oil emulsification and demulsification needs to be found.
Disclosure of Invention
The invention provides a surfactant with self-demulsification capability and a preparation method and application thereof in order to realize emulsification and high-efficiency demulsification of thickened oil.
In order to achieve the purpose, the invention adopts the following technical scheme:
a surfactant with self-demulsification capability is disclosed, wherein the structural formula of the compound is as follows:
a preparation method of a surfactant with self-demulsification capability comprises the following steps:
1) mixing dodecylamine and cyclobut-3-ene dicarboxylic anhydride, and performing nucleophilic addition-elimination reaction at 150-200 ℃ in a nitrogen atmosphere to generate imide;
2) adding an oxidant into the imide, and heating to 90-100 ℃ to perform an oxidation reaction to generate carboxyl; and after the reaction is finished, carrying out post-treatment to obtain a final product.
As a further improvement of the present invention, the nucleophilic addition-elimination reaction is carried out in a molar ratio of dodecylamine to cyclobut-3-enedicarboxylic anhydride of 1: 2.
As a further improvement of the invention, the oxidizing agent is potassium permanganate; the amount of potassium permanganate is 1-2 times of the amount of dodecylamine.
As a further improvement of the invention, in the oxidation reaction, after the imide is diluted, potassium permanganate is slowly added at 0 ℃, and then the temperature is raised for reaction.
As a further improvement of the invention, the post-treatment comprises:
and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate, filtering by adopting diatomite and extracting impurities by adopting ethyl acetate, collecting a water phase, adjusting the pH value to be 2-4 to separate out a product, and filtering and drying to constant weight to obtain a final product.
The surfactant with self-demulsification capability is applied as an emulsifier in a thick oil emulsification system.
When in use, the concentration of the emulsifier is 20 mg/L-2000 mg/L.
The surfactant with self-demulsification capability can be hydrolyzed into dodecylamine and 1,2,3, 4-butanetetracid under the condition that the external environment is alkaline.
The invention has the following advantages:
according to the preparation method, the surfactant has strong emulsifying capacity, the viscosity of the thick oil can be greatly reduced, and the dehydration rate of the emulsion is about 95%. The surfactant has an imide structure, and can be hydrolyzed in an alkaline environment, so that the surfactant is decomposed and inactivated. Therefore, in the process of demulsifying the emulsified thick oil, the pH value of the environment can be changed to inactivate the surfactant with the emulsifying function so as to realize high-efficiency demulsification. The surfactant has the characteristics of wide raw material source, excellent emulsifying effect and partial demulsification in later period.
The surfactant with self-demulsification capability can be used as an emulsifier to be applied to thick oil emulsification, can be applied to the thick oil emulsification to reduce the viscosity of the thick oil, has high pH value of the emulsified thick oil before oil refining, and realizes the demulsification of the emulsified thick oil due to the hydrolytic inactivation of the surfactant. The surfactant with self-demulsification capability can be hydrolyzed into dodecylamine and 1,2,3, 4-butanetetracid under the condition that the external environment is alkaline, and the surfactant loses the surface activity.
Drawings
FIG. 1 is a synthetic scheme of the surfactant having self-demulsification ability obtained in example 4.
FIG. 2 is a graph showing the surface tension test of the surfactant having self-demulsification ability obtained in example 4.
Detailed Description
The invention relates to a surfactant with self-demulsification capability, which has the reaction equation in the preparation process as follows:
according to the reaction mechanism, the invention adopts the following technical scheme:
a surfactant with self-demulsification capability has a structural formula as follows:
the method for preparing the surfactant with self-demulsification capability comprises the following steps:
dripping dodecylamine and cyclobut-3-ene dicarboxylic anhydride into a three-neck flask provided with a reflux condenser tube in sequence, introducing nitrogen, reacting for 2-5 h at 150-200 ℃, and performing a first nucleophilic addition-elimination reaction to generate imide, wherein the molar ratio of the dodecylamine to the cyclobut-3-ene dicarboxylic anhydride is 1: 2; diluting the product, slowly adding potassium permanganate at 0 ℃, and heating to react for 10-12 hours, wherein the amount of potassium permanganate is 1-2 times that of dodecylamine; and reducing excessive potassium permanganate by using sodium sulfite, dropwise adding dilute hydrochloric acid until the pH of the reaction solution is 2-4, separating out the product, and filtering and drying to constant weight to obtain the final product.
The surfactant with self demulsifying capacity is used as emulsifier in thick oil emulsifying system in the concentration of 20-2000 mg/L. The surfactant with self-demulsification capability is applied to thick oil emulsification to reduce the viscosity of the thick oil, the pH value of the emulsified thick oil is high before the emulsified thick oil enters oil refining, and the demulsification of the emulsified thick oil can be realized due to the hydrolytic inactivation of the surfactant.
The application principle is realized by the following reaction:
the surfactant with self-demulsification capability can be hydrolyzed into dodecylamine and 1,2,3, 4-tetracetic acid under the condition that the external environment is alkaline, and the surfactant loses the surface activity;
the technical solution in the embodiments of the present invention will be clearly and completely described below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
(1) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 180 ℃ for 3 hours, and TLC (Thin Layer Chromatography) was used to monitor completion of the reaction. After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) Adding imide and 40mL of distilled water into a 250mL three-neck flask, placing the flask in an ice salt bath, cooling the flask to 0 ℃, and slowly adding potassium permanganate KMnO4(20g, the adding time is 40min), and after the adding is finished, slowly raising the temperature to 90 ℃ for reaction for 12 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 2 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure final product.
The yield of the product obtained in example 1 was 62%.
Example 2
(1) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 150 ℃ for 2 hours, and completion of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) Adding imide and 40mL of distilled water into a 250mL three-neck flask, placing the flask in an ice salt bath, cooling the flask to 0 ℃, and slowly adding potassium permanganate KMnO4(15.8g, the adding time is 40min), after the adding is finished, the temperature is slowly raised to 100 ℃ for reaction for 10 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 3 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure final product.
The yield of the product obtained in example 2 was 54%.
Example 3
(1) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 200 ℃ for 5 hours, and completion of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) Adding imide and 40mL of distilled water into a 250mL three-neck flask, placing the flask in an ice salt bath, cooling the flask to 0 ℃, and slowly adding potassium permanganate KMnO4(25g, the addition time is 40min), and after the addition is finished, the temperature is slowly raised to 90 ℃ for reaction for 12 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate;then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 4 by using dilute hydrochloric acid to precipitate solids, and filtering and drying to obtain a pure final product.
The product obtained in example 3 is obtained in 61% yield.
Example 4
(1) In a 250mL three-necked flask equipped with a reflux condenser, dodecylamine (18.5g, 0.1mol) and cyclobutane-3-enedicarboxylic anhydride (24.8g, 0.2mol) were added dropwise in this order, and nitrogen was introduced 3 times, followed by heating to 190 ℃ for 5 hours, and completion of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction is finished, cooling to room temperature, adding 50mL of distilled water, extracting for 3 times by adopting 80mL of ethyl acetate, drying by anhydrous magnesium sulfate, filtering, concentrating under reduced pressure to obtain a crude product, and finally separating by a column to obtain colorless oily imide.
(2) Adding imide and 40mL of distilled water into a 250mL three-neck flask, placing the flask in an ice salt bath, cooling the flask to 0 ℃, and slowly adding potassium permanganate KMnO4(31.6g, the adding time is 40min), after the adding is finished, the temperature is slowly raised to 100 ℃ for reaction for 12 h. Excess KMnO was quenched by adding 80mL of saturated aqueous sodium sulfite solution to a three-necked flask4(ii) a After the purple color is faded, slowly cooling and filtering MnO generated in the reaction by diatomite while the MnO is hot2Obtaining clear filtrate; then extracting the filtrate for 3 times by using ethyl acetate to remove impurities, collecting a water phase, adjusting the pH value of the water phase to 2 by using dilute hydrochloric acid to precipitate a solid, and filtering and drying to obtain a pure final product.
The product obtained in example 4 was obtained in 68% yield.
In order to characterize the structural characteristics of the surfactant with self-demulsification capability, the surfactant with self-demulsification capability synthesized in example 4 was subjected to nuclear magnetic hydrogen spectrum test, and the results are as follows:
1H NMR(300MHz,DMSO):δ13.72(s,2H),3.92(s,2H),3.18(t,J＝7.1Hz,2H),1.51-1.27(m,20H),0.88(t,J＝7.3Hz,3H)ppm。
in order to characterize the emulsifying property of the surfactant with self-demulsification capability, 70 parts of thick oil, 30 parts of water and 0.5 part of surfactant are vigorously stirred for 60min at the temperature of 60 ℃,viscosity reduction rate measurement experiment is carried out by adopting a Brookfield rotary viscometer, and the shear rate is 50s-1And calculating the viscosity reduction rate.
The viscosity reduction rate is [ (viscous oil viscosity before emulsification-viscous oil viscosity)/viscous oil viscosity before emulsification ] × 100%
And (3) demulsification performance evaluation:
the water content of the prepared emulsified thick oil is 30 percent by using a bottle test method in the demulsification dehydration experiment. Adding the emulsified thick oil into a 200mL measuring cylinder with a plug, placing the cylinder in a thermostatic water bath with the temperature of 50 ℃ for preheating for 5min, then adopting NaOH to adjust the pH value of the emulsified thick oil to 11, recording the free water amount in 30min, and calculating the dehydration rate.
The dehydration rate was [ (30-volume of free water after dehydration)/30 ]. times.100%
TABLE 1 results of evaluation of emulsification and demulsification performances of samples of examples 1 to 4
The foregoing is a more detailed description of the invention and it is not intended that the invention be limited to the specific embodiments described herein, but that various modifications, alterations, and substitutions may be made by those skilled in the art without departing from the spirit of the invention, which should be construed to fall within the scope of the invention as defined by the appended claims.
Claims (9)
1. A surfactant with self-demulsification capability is characterized in that the structural formula of the compound is as follows:
2. a preparation method of a surfactant with self-demulsification capability is characterized by comprising the following steps:
1) mixing dodecylamine and cyclobut-3-ene dicarboxylic anhydride, and performing nucleophilic addition-elimination reaction at 150-200 ℃ in a nitrogen atmosphere to generate imide;
2) adding an oxidant potassium permanganate into the imide, and heating to 90-100 ℃ to perform an oxidation reaction to generate carboxyl; and after the reaction is finished, carrying out post-treatment to obtain a final product.
3. The method according to claim 2, wherein the nucleophilic addition-elimination reaction is performed in a molar ratio of dodecylamine to cyclobut-3-enedicarboxylic anhydride of 1: 2.
4. The method according to claim 2, wherein the amount of the potassium permanganate is 1 to 2 times the amount of the dodecylamine.
5. The method according to claim 2, wherein in the oxidation reaction, after the imide is diluted, potassium permanganate is slowly added at 0 ℃, and then the reaction is heated.
6. The method of manufacturing according to claim 2, wherein the post-treatment comprises:
and after the reaction is finished, adding sodium sulfite to remove excessive potassium permanganate, filtering by adopting diatomite and extracting impurities by adopting ethyl acetate, collecting a water phase, adjusting the pH value to be 2-4 to separate out a product, and filtering and drying to constant weight to obtain a final product.
7. Use of the surfactant having self-demulsifying ability according to claim 1 as an emulsifier in a thick oil emulsification system.
8. Use according to claim 7, wherein the emulsifier is used at a concentration of 20mg/L to 2000 mg/L.
9. The use according to claim 7, characterized in that the surfactant with self-breaking capacity is hydrolysable to dodecylamine and 1,2,3, 4-butanetetracid under alkaline conditions in the external environment.
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Citations (4)
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|---|---|---|---|---|
| US4069244A (en) * | 1975-01-03 | 1978-01-17 | Ciba-Geigy Corporation | Fluorinated amphoteric and cationic surfactants |
| JPH1150098A (en) * | 1997-08-06 | 1999-02-23 | Lion Corp | Solid soap composition |
| CN1379068A (en) * | 2001-03-29 | 2002-11-13 | 气体产品与化学公司 | Low foaming N-alkyl-tartraimine and N-alkyl melicimine wetting agent |
| CN101538311A (en) * | 2009-04-16 | 2009-09-23 | 山东大学 | Alpha-amido acyl-ring imide peptoid metalloprotease inhibitor and application thereof |
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| US20030229164A1 (en) * | 2002-06-10 | 2003-12-11 | Meier Ingrid Kristine | Low foam N-alkyltartarimide and N-alkylmalimide wetting agents |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069244A (en) * | 1975-01-03 | 1978-01-17 | Ciba-Geigy Corporation | Fluorinated amphoteric and cationic surfactants |
| JPH1150098A (en) * | 1997-08-06 | 1999-02-23 | Lion Corp | Solid soap composition |
| CN1379068A (en) * | 2001-03-29 | 2002-11-13 | 气体产品与化学公司 | Low foaming N-alkyl-tartraimine and N-alkyl melicimine wetting agent |
| CN101538311A (en) * | 2009-04-16 | 2009-09-23 | 山东大学 | Alpha-amido acyl-ring imide peptoid metalloprotease inhibitor and application thereof |
Non-Patent Citations (1)
| Title |
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| 《Surfactants from itaconic acid: Toxicity to HaCaT keratinocytes in vitro, micellar solubilization, and skin permeation enhancement of hydrocortisone》;Abruzzo等;《International Journal of Pharmaceutics》;20170327;第524卷;全文 * |
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Effective date of registration: 20211213 Address after: 751599 Yanchi County Industrial Park, Wuzhong City, Ningxia Hui Autonomous Region Patentee after: Ningxia Yuhang Oilfield Engineering Co.,Ltd. Address before: 710021 Shaanxi province Xi'an Weiyang University Park Patentee before: SHAANXI University OF SCIENCE & TECHNOLOGY |
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Granted publication date: 20211105 |