CN107586554B - Refining agent for removing organic nitride and thiophene sulfide in fuel oil - Google Patents
Refining agent for removing organic nitride and thiophene sulfide in fuel oil Download PDFInfo
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Abstract
The invention discloses a refining agent for removing organic nitrides and thiophene sulfides in fuel oil products, wherein the refining agent consists of active components of full-hydroxy-substituted column aromatic hydrocarbon, a stabilizer triethanolamine or propylene glycol dimethyl ether, a dispersant sodium dodecyl benzene sulfonate or hexadecyl trimethyl benzyl ammonium chloride and water. The refining agent mainly utilizes the clathration effect of the total hydroxyl substituted column aromatic hydrocarbon on organic nitride and thiophene sulfide in the fuel oil to realize deep removal, has the characteristics of easy recovery, greenness, easy operation and implementation and the like, and provides a novel green, environment-friendly and low-cost method for deep denitrification and desulfurization of the fuel oil.
Description
Technical Field
The invention belongs to the field of petroleum processing, and particularly relates to a refining agent for removing organic nitrides and thiophene sulfides in fuel oil products.
Background
At present, the requirement of people on the cleanliness of oil products is higher and higher, and one of the reasons for the quality of the oil products to be deteriorated is the existence of nitrides and sulfides in the petroleum products. The nitrides and sulfides in the oil product are mainly heterocyclic nitrides and thiophene sulfides, which are difficult to remove and have great influence on the stability, oxidation resistance and the like of the oil product; with simultaneous combustion producing Nitrogen Oxides (NO)X) And Sulfur Oxides (SO)X) Air pollution is caused. Therefore, the method has great significance in realizing deep denitrification and desulfurization of the oil product.
At present, the processes of denitrification and desulfurization of oil products include hydrogenation processes and non-hydrogenation processes. Among them, the hydrogenation process is mature and widely used, but causes loss of octane number, lubricating property and stability of oil products. While the existing non-hydrogenation processes (extraction method, adsorption method, oxidation method and the like) hardly cause loss of octane number, lubricating property, stability and the like of oil products, the removal efficiency is not high, and the development of a non-hydrodenitrification and desulfurization technology for novel fuel oil products is urgently needed. The pillar arene is used as a supermolecular main body, has a highly symmetrical and rigid structure and excellent molecular recognition capability, is commonly used for water treatment (CN 201610079351.5; CN 201610176308.0; CN 201410631270.2; CN201610266521.0), fluorescence recognition (CN 201610199037.0; CN 201510558495.4; CN 201610199027.7; CN201610909838.1) and the like, but has no report on removal of organic nitrides and thiophene sulfides in fuel oil products. The organic nitride in the fuel oil product mainly comprises pyridine, aniline, pyrrole, indole and quinoline, and the thiophene sulfide mainly comprises thiophene, benzothiophene and dibenzothiophene, and has good matching property with the pillar arene. The full hydroxyl substituted column [5] arene and the full hydroxyl substituted column [6] arene are soluble in water and insoluble in fuel oil, meanwhile, stabilizers such as triethanolamine, propylene glycol dimethyl ether and the like can effectively improve the stability of the column arene in the water, and dispersing agents such as sodium dodecyl benzene sulfonate, hexadecyl trimethyl benzyl ammonium chloride and the like can promote the two phases of a water phase and an oil liquid to be contacted more fully, so that the phase transfer efficiency and the separation efficiency are improved. Based on the above assumption, the active component of the column [5] arene or the column [6] arene substituted by full hydroxyl, the stabilizer of triethanolamine or propylene glycol dimethyl ether, the dispersant of sodium dodecyl benzene sulfonate or cetyl trimethyl benzyl ammonium chloride and water form a refining agent, the refining agent is used for removing organic nitrides and thiophene sulfides in fuel oil products, has the characteristics of easy recovery, green and easy operation and implementation, and provides a novel green, environment-friendly and low-cost method for deep denitrification and denitrogenation of the fuel oil products.
Disclosure of Invention
The invention aims to provide a refining agent for removing organic nitrides and thiophene sulfides in fuel oil products. A refining agent for removing organic nitrides and thiophene sulfides in fuel oil products is based on good matching of total hydroxyl substituted column [5] arene and total hydroxyl substituted column [6] arene with main organic nitrides (pyridine, aniline, pyrrole, indole and quinoline) and thiophene sulfides (thiophene, benzothiophene and dibenzothiophene) in the fuel oil products, the two are easy to generate supermolecule inclusion effect, meanwhile, the total hydroxyl substituted column [5] arene and the total hydroxyl substituted column [6] arene are soluble in water and insoluble in the fuel oil products, the removal process can be realized in an oil-water two-phase contact mode, nitrides and sulfides in the oil products are transferred into a cavity in the column arene (water phase), meanwhile, stabilizers such as triethanolamine and propylene glycol dimethyl ether are utilized to improve the stability of the column arene in the water, and dispersants such as sodium dodecyl benzene sulfonate and hexadecyl trimethyl benzyl ammonium chloride can promote the two-phase contact of the water phase and the liquid-liquid phase of the oil products to be more sufficient, the phase transfer efficiency and the separation efficiency are improved.
The invention adopts the following technical scheme:
the invention provides a refining agent for removing organic nitrides and thiophene sulfides in fuel oil products, which consists of active components of full hydroxyl substituted column [5] arene or full hydroxyl substituted column [6] arene, stabilizer triethanolamine or propylene glycol dimethyl ether, dispersant sodium dodecyl benzene sulfonate or hexadecyl trimethyl benzyl ammonium chloride and water.
The refining agent for removing organic nitrides and thiophene sulfides in fuel oil has the active components with the mass concentration of 0.1-5% in water, the stabilizer accounting for 0.01-0.5% of the water, and the dispersant accounting for 0.1-0.5% of the water.
The refining agent for removing the organic nitride and the thiophene sulfide in the fuel oil product, disclosed by the invention, has the advantages that the organic nitride removed from the fuel oil product comprises pyridine, aniline, pyrrole, indole and quinoline, and the thiophene sulfide removed from the fuel oil product comprises thiophene, benzothiophene and dibenzothiophene.
The preparation of the refining agent for removing the organic nitride and the thiophene sulfide in the fuel oil product comprises the following steps: dissolving the total hydroxyl substituted column [5] arene or the total hydroxyl substituted column [6] arene (active component) by using water as a solvent, adding a proper amount of a stabilizer and a dispersant, and shaking up to ensure that the mass concentration of the active component in water is 0.1-5%, the mass fraction of the stabilizer in water is 0.01-0.5%, and the mass fraction of the dispersant in water is 0.1-0.5%.
The evaluation method of the refining agent for removing organic nitrides and thiophene sulfides in fuel oil comprises the following steps: mixing an oil product containing organic nitride or/and sulfide with a certain concentration with a refining agent according to a certain agent-oil volume ratio, stirring at a certain removal temperature (the stirring speed is 500rpm) for a certain time at normal pressure, standing for a certain time, and analyzing the nitrogen/sulfur content in the oil layer. The denitrification or sulfur ratio is calculated according to the formula (1):
E％＝(C0-C1)×100/C0formula (1)
In the formula (1), the reaction mixture is,
e% -removal rate of organic nitrides or thiophenic sulfides;
C0concentration of nitrogen or sulfur before stripping,. mu.g.g-1；
C1Concentration of nitrogen or sulfur after removal,. mu.g.g-1。
In the evaluation method for removing organic nitride and thiophene sulfide in fuel oil by using the refining agent, the concentration of organic nitrogen or sulfur is 50-200 mu g.g-1The volume ratio of the solvent to the oil is 1: 5-5: 1, the removal temperature is 20-50 ℃, the stirring time is 10-120 min, and the standing time is 2-10 min.
The refining agent for removing the organic nitride and the thiophene sulfide in the fuel oil has the following advantages:
the active component of the full-hydroxyl substituted column [5] arene or the full-hydroxyl substituted column [6] arene in the refining agent is green and low in cost, the preparation method is simple and easy to operate, and the refining agent is easy to recycle, so that a novel green, environment-friendly and low-cost method is provided for deep denitrification and desulfurization of fuel oil.
Drawings
FIG. 1 shows the comparison of the removal rates of aniline nitrogen and benzothiophene sulfur in the refining agent of the present invention and water (1, refining agent E of the present invention; 2, water)
Detailed Description
Example 1
50mL of water was used as a solvent, and 0.05g of a perhydroxyl-substituted column [5]]Aromatic hydrocarbon, then 0.005g triethanolamine and 0.05g hexadecyl trimethyl benzyl ammonium chloride are added, shaken up to be completely dissolved, so that the column [5] substituted by full hydroxyl is obtained]The mass concentrations of the aromatic hydrocarbon, the triethanolamine and the hexadecyl trimethyl benzyl ammonium chloride in water are 0.1 percent, 0.01 percent and 0.1 percent in sequence, and the refining agent A is formed. Will contain 50. mu.g.g-1Mixing the oil product of pyrrole nitrogen with the refining agent A according to the volume ratio of the oil product of pyrrole nitrogen to the oil product of refining agent A of 1:5, stirring for 30min (the stirring speed is 500rpm) at the normal pressure and 20 ℃, and standing for 2min, wherein the removal rate of pyrrole nitrogen is 20.4%.
Example 2
Using 50mL of water as a solvent, 0.25g of a fully hydroxy-substituted column [ column ], [ solution ]5]Arene, then 0.015g triethanolamine and 0.15g sodium dodecyl benzene sulfonate are added, shaken up to be completely dissolved, so that the column [5] substituted by full hydroxyl is obtained]The mass concentrations of the aromatic hydrocarbon, the triethanolamine and the sodium dodecyl benzene sulfonate in the water are 0.5 percent, 0.03 percent and 0.3 percent in sequence, and the refining agent B is formed. Will contain 100. mu.g.g-1Mixing the oil product of pyrrole nitrogen with the refining agent B according to the volume ratio of the oil product to the oil product of 1:3, stirring for 120min (the stirring speed is 500rpm) at the normal pressure and at the temperature of 30 ℃, and standing for 10min, wherein the removal rate of pyrrole nitrogen is 41.5%.
Example 3
50mL of water was used as a solvent, and 0.5g of a total hydroxy-substituted column [5] was added]Adding 0.25g of propylene glycol dimethyl ether and 0.075g of hexadecyl trimethyl benzyl ammonium chloride into the aromatic hydrocarbon, and shaking the mixture until the mixture is completely dissolved so as to obtain a full hydroxyl substituted column [5]]The mass concentrations of the aromatic hydrocarbon, the propylene glycol dimethyl ether and the hexadecyl trimethyl benzyl ammonium chloride in the water are 1 percent, 0.5 percent and 0.15 percent in sequence, and the refining agent C is formed. Will contain 75. mu.g.g-1Mixing the pyridine nitrogen oil product and the refining agent C according to the volume ratio of the oil product to the oil product of 1:2, stirring for 10min (the stirring speed is 500rpm) at the normal pressure and at the temperature of 25 ℃, and standing for 2min, wherein the removal rate of the pyridine nitrogen is 32.6%.
Example 4
50mL of water was used as a solvent, and 1.25g of a perhydroxy-substituted column [5] was added]Adding 0.05g triethanolamine and 0.1g sodium dodecylbenzenesulfonate into aromatic hydrocarbon, shaking to dissolve completely, and making into total hydroxy substituted column [ 5%]The mass concentrations of the aromatic hydrocarbon, the triethanolamine and the sodium dodecyl benzene sulfonate in the water are 2.5 percent, 0.1 percent and 0.2 percent in sequence, and the refining agent D is formed. Will contain 200. mu.g.g-1Pyridine nitrogen and a nitrogen content of 100. mu.g.g-1Mixing the oil product of the thiophenic sulfur with the refining agent D according to the volume ratio of the oil product of the thiophenic sulfur to the oil product of the refining agent D of 5:1, stirring for 50min (the stirring speed is 500rpm) at normal pressure and 40 ℃, standing for 3min, and then sequentially removing the pyridine nitrogen and the thiophenic sulfur by 62.6 percent and 41.8 percent.
Example 5
50mL of water was used as a solvent, and 1.5g of a column [5] substituted with a total hydroxyl group was added]Aromatic hydrocarbon, then 0.035g propylene glycol dimethyl ether and 0.25g hexadecyl trimethyl benzyl ammonium chloride are added, shaken up until complete dissolution, so that the column [5] substituted by full hydroxyl is obtained]Aromatic hydrocarbon, propylene glycolThe mass concentrations of the dimethyl ether and the hexadecyl trimethyl benzyl ammonium chloride in the water are 3 percent, 0.07 percent and 0.5 percent in sequence, and a refining agent E is formed. Will contain 100. mu.g.g-1Mixing the aniline nitrogen oil product and the refining agent E according to the volume ratio of the oil product to the oil product of 1:1, stirring for 40min (the stirring speed is 500rpm) at the normal pressure and at the temperature of 50 ℃, and standing for 4min to ensure that the removal rate of aniline nitrogen is 47.4 percent.
Example 6
50mL of water was used as a solvent, and 2g of a column [5] substituted with a total hydroxyl group was added]Aromatic hydrocarbon, then 0.1g triethanolamine and 0.15g hexadecyl trimethyl benzyl ammonium chloride are added, shaken up to be completely dissolved, so that the column [5] substituted by full hydroxyl is obtained]The mass concentrations of the aromatic hydrocarbon, the triethanolamine and the nonacetyl trimethyl benzyl ammonium chloride in the water are 4 percent, 0.2 percent and 0.3 percent in sequence, and the refining agent F is formed. Will contain 150. mu.g.g-1Aniline nitrogen and its content of 50 mug g-1Mixing the oil product of the benzothiophene sulfur with the refining agent F according to the volume ratio of the oil product to the oil product of 3:1, stirring for 60min (the stirring speed is 500rpm) at the normal pressure and at the temperature of 40 ℃, and standing for 5min to ensure that the removal rates of aniline nitrogen and benzothiophene sulfur are 57.4 percent and 52.9 percent in sequence.
Example 7
50mL of water was used as a solvent, and 2.5g of a column [6] substituted with a total hydroxyl group was added]Aromatic hydrocarbon, then 0.2g propylene glycol dimethyl ether and 0.2g hexadecyl trimethyl benzyl ammonium chloride are added, and the mixture is shaken up to be completely dissolved, so that the column [6] substituted by full hydroxyl is obtained]The mass concentrations of the aromatic hydrocarbon, the propylene glycol dimethyl ether and the hexadecyl trimethyl benzyl ammonium chloride in the water are 5 percent, 0.4 percent and 0.4 percent in sequence, and the refining agent G is formed. Will contain 150. mu.g.g-1Mixing the oil product of indole nitrogen with the refining agent G according to the volume ratio of the oil product of indole nitrogen being 2:1, stirring for 90min (the stirring speed is 500rpm) at the normal pressure and 50 ℃, and standing for 5min, wherein the removal rate of indole nitrogen is 41.5%.
Example 8
50mL of water was used as a solvent, and 1g of a column [6] substituted with a total hydroxyl group was added]Aromatic hydrocarbon, then 0.15g triethanolamine and 0.125g hexadecyl trimethyl benzyl ammonium chloride are added, shaken up to be completely dissolved, so that the column [6] substituted by full hydroxyl is obtained]The mass concentration of the aromatic hydrocarbon, the triethanolamine and the hexadecyl trimethyl benzyl ammonium chloride in the water is 2 percent, 0.3 percent and 0.25 percent in sequenceRefining agent H. Will contain 200. mu.g.g-1Oil product containing indole nitrogen and oil product containing indole nitrogen 100 microgram g-1Indole nitrogen, 100 mug. g-1Mixing the oil product of the benzothiophene sulfur with the refining agent H according to the volume ratio of the oil product to the oil product of 1:2, stirring for 100min (the stirring speed is 500rpm) at the normal pressure and at the temperature of 20 ℃, standing for 6min, and then sequentially obtaining the removal rate of 40.7% and 36.7%.
Example 9
50mL of water was used as a solvent, and 0.35g of a total hydroxy-substituted column [6] was added]Adding 0.25g of propylene glycol dimethyl ether and 0.175g of sodium dodecyl benzene sulfonate into the aromatic hydrocarbon, shaking up until the mixture is completely dissolved, and enabling the column [6] substituted by full hydroxyl]The mass concentrations of the aromatic hydrocarbon, the propylene glycol dimethyl ether and the sodium dodecyl benzene sulfonate in the water are 0.7 percent, 0.5 percent and 0.35 percent in sequence, and the refining agent I is formed. Will contain 50. mu.g.g-1Mixing the quinoline nitrogen oil product and the refining agent I according to the volume ratio of the agent to the oil being 1:4, stirring for 120min (the stirring speed is 500rpm) at the normal pressure and at the temperature of 30 ℃, and standing for 7min to ensure that the removal rate of the quinoline nitrogen is 30.4 percent.
Example 10
50mL of water was used as a solvent, and 0.15g of a perhydroxyl-substituted column [6] was added]Aromatic hydrocarbon, then 0.1g propylene glycol dimethyl ether and 0.225g hexadecyl trimethyl benzyl ammonium chloride are added, and the mixture is shaken up to be completely dissolved, so that the column [6] substituted by full hydroxyl is obtained]The mass concentrations of the aromatic hydrocarbon, the propylene glycol dimethyl ether and the hexadecyl trimethyl benzyl ammonium chloride in water are 0.3 percent, 0.2 percent and 0.45 percent in sequence, and a refining agent J is formed. Will contain 150. mu.g.g-1Mixing the quinoline nitrogen oil product and the refining agent J according to the volume ratio of the agent to the oil being 4:1, stirring for 45min (the stirring speed is 500rpm) at the temperature of 40 ℃ under normal pressure, and standing for 5min to ensure that the removal rate of the quinoline nitrogen is 42.9 percent.
Example 11
50mL of water was used as a solvent, and 2g of a column [6] substituted with a total hydroxyl group was added]Aromatic hydrocarbon, then 0.1g triethanolamine and 0.15g hexadecyl trimethyl benzyl ammonium chloride are added, shaken up to be completely dissolved, so that the column [6] substituted by full hydroxyl is obtained]The mass concentrations of the aromatic hydrocarbon, the triethanolamine and the hexadecyl trimethyl benzyl ammonium chloride in the water are 4 percent, 0.2 percent and 0.3 percent in sequence, and the refining agent K is formed. Will contain 125 mug g-1Quinoline Nitrogen or 100. mu.g.g-1Process for preparing dibenzothiophene sulfidesMixing the oil product and the refining agent K according to the volume ratio of the oil product to the oil product of 1:1, stirring for 120min (the stirring speed is 500rpm) at the normal pressure and at the temperature of 25 ℃, and standing for 10min to ensure that the removal rates of quinoline nitrogen and dibenzothiophene sulfur are 50.7% and 47.8% in sequence.
Comparative example 1 was carried out
Will contain 100. mu.g.g-1Aniline nitrogen or 100 mug g-1The oil product of benzothiophene sulfur was mixed with the refining agent E or water at a solvent-to-oil volume ratio of 5:1, stirred at 20 ℃ for 90min at normal pressure (stirring speed 500rpm), and then allowed to stand for 10min, and then the removal rates of aniline nitrogen and benzothiophene sulfur were analyzed, and the results are shown in FIG. 1.
As can be seen from figure 1, the refining agent of the invention has excellent removal effect, the refining agent has the total hydroxyl substituted column [5] arene which has main denitrification and desulfurization effects, water also has certain removal effect (aniline is slightly soluble in water, and benzothiophene is excluded), and the stabilizer and the dispersant enhance the performance of the total hydroxyl substituted column [5] arene inclusion for removing aniline and benzothiophene; therefore, the refining agent is not a simple combination of several substances, but the screened removal components are carefully considered to synergistically play roles in denitrification and desulfurization.
Comparative example 2 was carried out
Oil products containing aniline nitrogen, pyridine nitrogen and pyrrole nitrogen (the total nitrogen content is 60 mu g)-1The ratio of the three nitrogen contents is 1:1:1) or oil products containing indole nitrogen and quinoline nitrogen (the total nitrogen content is 60 mu g.g)-1The ratio of the two nitrogen contents is 1:1) or oil products containing thiophenic sulfur, benzothiophenic sulfur and dibenzothiophenic sulfur (the total sulfur content is 60 mu g-1The ratio of the three sulfur contents is 1:1) the mixture was mixed with a refining agent F or a refining agent K at a volume ratio of 3:1, stirred at 20 ℃ for 120min (stirring speed of 500rpm) at normal pressure, and then allowed to stand for 10min, to compare the removal effects of the refining agent of the present invention on mixed nitride and sulfide oils, and the results are shown in Table 1.
TABLE 1 removal effect of mixed nitride and sulfide oil products of refining agents of the present invention
As can be seen from Table 1, the refining agent of the invention can effectively remove mixed nitrides and sulfides in oil products, and simultaneously, the active component, namely the full-hydroxy-substituted column aromatic hydrocarbon, is found to have removal selectivity, the full-hydroxy-substituted column [5] aromatic hydrocarbon has good removal effect on nitrides and sulfides containing monocyclic structures, and the full-hydroxy-substituted column [6] aromatic hydrocarbon has good removal effect on nitrides and sulfides containing polycyclic (bicyclic or tricyclic) structures.
Comparative example 3 was carried out
Oil products containing aniline nitrogen, pyridine nitrogen, pyrrole nitrogen and thiophene sulfur (the total nitrogen and sulfur content is 80 mug. g)-1Each content ratio is 1:1:1:1) or oil product containing indole nitrogen, quinoline nitrogen, benzothiophene sulfur and dibenzothiophene sulfur (total nitrogen and sulfur content is 80 mug g)-1The volume ratio of each of the components is 1:1:1:1) and the volume ratio of the refining agent F or the refining agent K is 5:1, the mixture is stirred for 90min at the normal pressure and the temperature of 20 ℃, and after standing for 10min, the total removal effect of the refining agent on mixed nitride and sulfide oil products is compared, and the results are shown in Table 2.
TABLE 2 effect of refining agent of the present invention on removal of mixed nitrogen and sulfide oil
As can be seen from Table 2, the refining agent of the present invention still has a good effect of removing oil products containing both sulfide and nitride. In practical application, the proportion of active components, stabilizing agents and dispersing agents in the refining agent is reasonably optimized according to the type and content of sulfides and nitrides in the oil product, so that the sulfides and the nitrides in the oil product are effectively removed, and the aim of refining the oil product is fulfilled.
It is to be understood that the above examples are illustrative for clarity and are not intended to limit the embodiments of the refining agent of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. All embodiments need not be, and cannot be, enumerated here. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (2)
1. A refining agent for removing organic nitride and thiophene sulfide in fuel oil is characterized by comprising active components of full hydroxyl substituted column [5] arene or full hydroxyl substituted column [6] arene, stabilizer triethanolamine or propylene glycol dimethyl ether, dispersant sodium dodecyl benzene sulfonate or hexadecyl trimethyl benzyl ammonium chloride and water; the mass concentration of the active components in the refining agent in water is 0.1-5%, the mass fraction of the stabilizer in water is 0.01-0.5%, and the mass fraction of the dispersant in water is 0.1-0.5%.
2. The refining agent for removing organic nitrides and thiophenic sulfides in fuel oil according to claim 1, wherein the organic nitrides removed from the fuel oil comprise pyridine, aniline, pyrrole, indole and quinoline, and the thiophenic sulfides removed from the fuel oil comprise thiophene, benzothiophene and dibenzothiophene.
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| CN101544907A (en) * | 2008-03-26 | 2009-09-30 | 通用电气公司 | Oxidative desulfurization of fuel oil |
| CN105087050A (en) * | 2015-09-11 | 2015-11-25 | 中国石油大学(华东) | Fuel oil product denitrifier using supramolecular inclusion effect and application method thereof |
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| CN101544907A (en) * | 2008-03-26 | 2009-09-30 | 通用电气公司 | Oxidative desulfurization of fuel oil |
| CN105087050A (en) * | 2015-09-11 | 2015-11-25 | 中国石油大学(华东) | Fuel oil product denitrifier using supramolecular inclusion effect and application method thereof |
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