CN117229191A - Application of quaternary ammonium salt acid eutectic solvent in indole extraction - Google Patents
Application of quaternary ammonium salt acid eutectic solvent in indole extraction Download PDFInfo
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- CN117229191A CN117229191A CN202311190636.2A CN202311190636A CN117229191A CN 117229191 A CN117229191 A CN 117229191A CN 202311190636 A CN202311190636 A CN 202311190636A CN 117229191 A CN117229191 A CN 117229191A
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- Prior art keywords
- eutectic solvent
- indole
- quaternary ammonium
- ammonium salt
- salt acid
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 239000002904 solvent Substances 0.000 title claims abstract description 69
- 230000005496 eutectics Effects 0.000 title claims abstract description 64
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims abstract description 59
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 38
- 239000002253 acid Substances 0.000 title claims abstract description 35
- 238000000605 extraction Methods 0.000 title claims abstract description 20
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims abstract description 30
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229940040102 levulinic acid Drugs 0.000 claims abstract description 15
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims abstract description 15
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 4
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 3
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000005191 phase separation Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- -1 nitrogen-containing heterocyclic compounds Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000000295 fuel oil Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 238000003916 acid precipitation Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Indole Compounds (AREA)
Abstract
The invention relates to the field of eutectic solvents, in particular to application of a quaternary ammonium salt acidic eutectic solvent in indole extraction. The method comprises the following steps of placing a quaternary ammonium salt acid eutectic solvent into an n-octane solution containing indole, and extracting the indole under the conditions of constant temperature and stirring; the structural formulas of tetrabutyl ammonium bromide and levulinic acid used for synthesizing the quaternary ammonium salt acid eutectic solvent are respectively shown as the following formulas (I) and (II). The quaternary ammonium salt acid eutectic solvent prepared by the invention has stronger trapping capacity for indole; meanwhile, the eutectic solvent has better phase forming capability and can achieve phase separation under a smaller dosage. The mass ratio of the quaternary ammonium salt acid eutectic solvent to the model oil is 1: in the case of 5, the recovery efficiency of indole is as high as 97.73%. The quaternary ammonium salt acid eutectic solvent extractant has high separation efficiency, is environment-friendly and has low price.
Description
Technical Field
The invention relates to the field of eutectic solvents, in particular to application of a quaternary ammonium salt acidic eutectic solvent in indole extraction.
Background
In oil applications, the presence of nitrides reduces the stability of the oil, which is detrimental to the storage and use of the oil. And nitrogen oxides released in the process of fuel combustion have important influence on the formation of haze and acid rain, so that the removal of nitrogen-containing heterocyclic compounds from fuel oil products such as gasoline, diesel oil and lubricating oil is important for improving the quality of petroleum and protecting the environment. Indole is a nitrogen-containing compound contained in fuel oil, so that extraction of indole from fuel oil is important.
The eutectic solvent is a novel green solvent and is formed by directly mixing hydrogen bond acceptors such as quaternary ammonium salt and hydrogen bond donors such as polyalcohol, amide and carboxylic acid. The eutectic solvent not only has similar physical and chemical properties as ionic liquid, such as low vapor pressure, difficult volatilization, designable structural performance and the like, but also has low raw material cost, simple preparation and good biocompatibility, thereby providing a new platform for the development of separation technology.
The eutectic solvent has functional groups which interact with indole, and has stronger trapping capacity for indole; meanwhile, the eutectic solvent has better phase forming capability and can achieve phase separation under a smaller dosage. The quaternary ammonium salt acid eutectic solvent can form hydrogen bonds with indole, and has stronger trapping capacity for nitrogen-containing compound substances. Provides an effective way for extracting indole from organic solvent.
Disclosure of Invention
The method can effectively extract the indole in the organic solvent, and has the advantages of simple operation, low cost, high purity and strong stability.
In order to achieve the above purpose, the invention adopts the following technical scheme: the application of quaternary ammonium salt acid eutectic solvent in extracting indole includes setting quaternary ammonium salt acid eutectic solvent in n-octane solution containing indole, and extracting indole under constant temperature and stirring; structural formulas of tetrabutyl ammonium bromide and levulinic acid used for synthesizing the quaternary ammonium salt acid eutectic solvent are respectively shown as the following formulas (I) and (II):
the application of the quaternary ammonium salt acid eutectic solvent in extracting indole comprises the following steps of: indole-containing n-octane solution = 1:5, indole concentration in the n-octane solution containing indole was 200ppm.
The application of the quaternary ammonium salt acid eutectic solvent in extracting indole is that the constant temperature is 30 ℃.
The application of the quaternary ammonium salt acid eutectic solvent in extracting indole is characterized in that the preparation method of the quaternary ammonium salt acid eutectic solvent is as follows:
1) Drying of tetrabutylammonium bromide: vacuum drying tetrabutylammonium bromide;
2) Purification and drying of levulinic acid: performing vacuum rotary evaporation on levulinic acid;
3) Synthesis of eutectic solvent: and mixing tetrabutylammonium bromide and levulinic acid, stirring for reaction until a uniform transparent liquid is formed, and vacuum drying to obtain the target eutectic solvent.
The application of the green and economic eutectic solvent in the indole extraction, wherein in the step 1), the condition of vacuum drying is that the vacuum is carried out for 48 hours at 55 ℃ under the vacuum degree of 0.09 MPa;
the application of the green and economic eutectic solvent in the indole extraction, in the step 2), the condition of rotary evaporation is as follows: vacuum rotary heating is carried out for 12h under the condition of the vacuum degree of 0.09MPa and the temperature of 65 ℃.
The application of the green and economic eutectic solvent in extracting indole, wherein in the step 3), tetrabutylammonium bromide is prepared according to the molar ratio: levulinic acid was 1:2.
The use of a green and economical eutectic solvent as described above for the extraction of indole, step 3), the temperature of the stirring reaction being 60 ℃.
The application of the green and economic eutectic solvent in the indole extraction, wherein in the step 3), the reaction time is 2 hours.
Compared with the prior art, the invention has the following remarkable advantages:
1. the quaternary ammonium salt acid eutectic solvent prepared by the invention has wider liquid category, is non-volatile, is an excellent green solvent, and reduces energy consumption and environmental pollution.
2. The quaternary ammonium salt acid eutectic solvent prepared by the invention has stronger trapping capacity for indole; meanwhile, the eutectic solvent has better phase forming capability and can achieve phase separation under a smaller dosage.
3. The quaternary ammonium salt acid eutectic solvent prepared by the invention can form hydrogen bonds with indole, so that the aim of efficiently extracting and separating indole can be fulfilled.
4. The quaternary ammonium salt acid eutectic solvent prepared by the invention has low price, good chemical stability, wide liquid range and high extraction efficiency.
Drawings
FIG. 1 is a hydrogen spectrum of the quaternary ammonium salt acid eutectic solvent prepared in example 1.
FIG. 2 is an infrared spectrum of the quaternary ammonium salt acid eutectic solvent prepared in example 1.
Detailed Description
The invention is further illustrated by the following specific examples. The present invention is not limited to example 1, and may be modified slightly without departing from the scope described above.
Example 1A quaternary ammonium acid eutectic solvent for extraction of indole
The preparation method comprises the following steps:
1) Tetrabutylammonium bromide is placed in a vacuum drying oven and vacuum is carried out for 48 hours under the conditions of 0.09MPa vacuum degree and 55 DEG C
2) Adding levulinic acid into a round bottom flask, and performing vacuum rotary heating for 12h at the temperature of 65 ℃ under the vacuum degree of 0.09MPa by using a rotary evaporator;
3) Tetrabutylammonium bromide and levulinic acid are mixed according to a molar ratio of 1:2 weighing the corresponding mass and placing the sample in a sample bottle. Stirring and reacting for 2h at 60 ℃ to form uniform transparent liquid. Vacuum drying is carried out for 48 hours at the temperature of 60 ℃ under the vacuum degree of 0.09MPa, and water is removed, so that the final product tetrabutylammonium bromide-levulinic acid (molar ratio 1:2) eutectic solvent is obtained.
Characterization of quaternary ammonium salt acid eutectic solvent:
(1) Hydrogen spectrum: tetrabutylammonium bromide-levulinic acid (molar ratio 1:2) eutectic solvent nuclear magnetic resonance hydrogen spectrum 1 H NMR tableSign (300 MHz, solvent DMSO-d) 6 ) See fig. 1. The nuclear magnetic hydrogen spectrum is analyzed, 1 the chemical shift and the number of formants of H NMR are consistent with those of the target eutectic solvent, and no impurity peaks are found.
(2) Infrared spectrogram: the infrared characterization of the tetrabutylammonium bromide-levulinic acid (molar ratio 1:2) eutectic solvent is shown in figure 2. And (3) analyzing an infrared spectrogram, wherein the infrared spectrogram of the eutectic solvent contains characteristic peaks of a hydrogen bond acceptor (tetrabutylammonium bromide) and a hydrogen bond donor (levulinic acid), does not generate a new characteristic peak, and indicates that no chemical reaction between the tetrabutylammonium bromide and the levulinic acid generates a new substance, and is combined only through hydrogen bond interaction.
EXAMPLE 2 application of quaternary ammonium salt acid eutectic solvent to extraction of indole
Extraction separation experiment
Dissolving a certain amount of indole in n-octane to prepare an indole solution (model oil) with the indole concentration of 200ppm for later use, weighing 1g of quaternary ammonium salt acidic low-cosolvent solvent in a 10mL graduated test tube, and adding 5g of model oil, wherein the mass ratio of the quaternary ammonium salt acidic low-eutectic solvent to the indole is 1:5. the indole extraction and separation experiment was performed with magnetic stirring at 30 ℃.
Extracting for 60min, and standing for 30 min. The concentration of indole in the n-octane phase at 254nm was measured using uv-vis spectrophotometry. At least 3 samples are taken from the n-octane phase for quantitative determination, and the relative error in balancing is controlled within 3 percent so as to ensure the accuracy of data. The extraction efficiency (E%) of indole was calculated according to the following formulas (1-1):
wherein C is 0 Represents the initial concentration of indole in the model oil, C f The concentration of indole remaining for the n-octane phase.
Extraction rate of indole by quaternary ammonium salt acid eutectic solvent
After the quaternary ammonium salt acid eutectic solvent is extracted, the extraction rate of the quaternary ammonium salt acid eutectic solvent to indole is calculated to be 97.73%.
Claims (9)
1. The application of the quaternary ammonium salt acid eutectic solvent in the extraction of indole is characterized in that the method comprises the following steps of placing the quaternary ammonium salt acid eutectic solvent in an n-octane solution containing indole, and extracting the indole under the conditions of constant temperature and stirring; the structural formulas of tetrabutyl ammonium bromide and levulinic acid used for synthesizing the quaternary ammonium salt acid eutectic solvent are respectively shown as formulas (I) and (II):
2. the use of a quaternary ammonium salt acid eutectic solvent in extracting indole according to claim 1, wherein the quaternary ammonium salt acid eutectic solvent comprises the following components in mass ratio: indole-containing n-octane solution = 1:5, indole concentration in the n-octane solution containing indole was 200ppm.
3. Use of a quaternary ammonium acid eutectic solvent in the extraction of indole according to claim 1, wherein the constant temperature is 30 ℃.
4. The application of the quaternary ammonium salt acid eutectic solvent in extracting indole according to claim 1, wherein the preparation method of the quaternary ammonium salt acid eutectic solvent is as follows:
1) Drying of tetrabutylammonium bromide: vacuum drying tetrabutylammonium bromide;
2) Purification and drying of levulinic acid: performing vacuum rotary evaporation on levulinic acid;
3) Synthesis of eutectic solvent: and mixing tetrabutylammonium bromide and levulinic acid, stirring for reaction until a uniform transparent liquid is formed, and vacuum drying to obtain the target eutectic solvent.
5. The use of a green economical eutectic solvent for extracting indole according to claim 4, wherein in step 1), the vacuum drying is performed under a vacuum of 0.09MPa at 55 ℃ for 48h.
6. The use of a green economical eutectic solvent for extracting indole according to claim 4, wherein in step 2), the conditions of rotary evaporation are: vacuum rotary heating is carried out for 12h under the condition of the vacuum degree of 0.09MPa and the temperature of 65 ℃.
7. Use of a green economical eutectic solvent for the extraction of indole according to claim 4, wherein in step 3), tetrabutylammonium bromide is used in a molar ratio: levulinic acid was 1:2.
8. The use of a green economical eutectic solvent for extracting indole according to claim 4, wherein in step 3) the temperature of the stirring reaction is 60 ℃.
9. The use of a green economical eutectic solvent for extracting indole according to claim 4, wherein in step 3), the reaction time is 2h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202311190636.2A CN117229191A (en) | 2023-09-15 | 2023-09-15 | Application of quaternary ammonium salt acid eutectic solvent in indole extraction |
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| CN202311190636.2A CN117229191A (en) | 2023-09-15 | 2023-09-15 | Application of quaternary ammonium salt acid eutectic solvent in indole extraction |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117402339A (en) * | 2023-12-14 | 2024-01-16 | 山东理工大学 | Preparation method of oligomeric lactic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117402339A (en) * | 2023-12-14 | 2024-01-16 | 山东理工大学 | Preparation method of oligomeric lactic acid |
| CN117402339B (en) * | 2023-12-14 | 2024-02-13 | 山东理工大学 | Preparation method of oligomeric lactic acid |
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