CN111484874A - Method for extracting, reducing and desulfurizing fuel oil in eutectic solvent - Google Patents
Method for extracting, reducing and desulfurizing fuel oil in eutectic solvent Download PDFInfo
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- CN111484874A CN111484874A CN202010188277.7A CN202010188277A CN111484874A CN 111484874 A CN111484874 A CN 111484874A CN 202010188277 A CN202010188277 A CN 202010188277A CN 111484874 A CN111484874 A CN 111484874A
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen
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Abstract
The invention provides a method for extracting, reducing and desulfurizing fuel oil in a eutectic solvent, which comprises the steps of mixing the fuel oil, the eutectic solvent and sodium borohydride in proportion and then adding the mixture into a reactor; then, slowly adding nickel salt into the reactor under stirring to perform desulfurization reaction; and after the reaction is finished, separating the mixture in the reactor to obtain an upper oil phase, namely the low-sulfur fuel oil. The invention takes eutectic solvent as NaBH4The reaction medium in the reduction desulfurization process can avoid the problems of organic solvent, and the nickel boride particles generated by the reaction of sodium borohydride and nickel salt have small particle size and large specific surface area, thereby greatly improving the NaBH4The efficiency of the reduction desulfurization.
Description
Technical Field
The invention relates to the field of fuel oil desulfurization, in particular to a method for extracting, reducing and desulfurizing fuel oil in a eutectic solvent.
Background
Sulfide hazards in fuel oil, e.g. SO from combustion2Causing acid rain problems, causing catalyst poisoning in automotive three-way catalysts, causing corrosion of petroleum processing equipment, and the like. Therefore, more and more stringent fuel oil sulfur content standards have been established in most countries. At present, the fuel oil desulfurization process commonly adopted in industry is Hydrodesulfurization (HDS), although the HDS process can obtain higher desulfurization efficiency, the operation condition is harsh, and the process is suitable for desulfurization of fuel oilThe desulfurization effect of benzothiophene and dibenzothiophene sulfides in fuel oil is poor, and the octane number of oil products can be reduced. Therefore, various non-hydrodesulfurization technologies, such as adsorption desulfurization, extraction desulfurization, oxidation desulfurization, biological desulfurization, etc., are receiving increasing attention from researchers.
Sodium borohydride (NaBH)4) Is a strong reducing agent and is commonly used for the reduction desulfurization of organic sulfides in the presence of nickel salts. The desulfurization mechanism is as follows: first, NaBH4Reacting with nickel salt to generate nickel boride and active hydrogen; and then, the organic sulfide and active hydrogen are adsorbed on the surface of the nickel boride, and under the combined action of the nickel boride and the active hydrogen, the carbon-sulfur bond of the organic sulfide is broken, so that desulfurization is realized. NaBH4The reduction desulfurization method has mild reaction conditions, has good desulfurization effect on thiophene sulfides, does not damage the quality of oil products, and has a very good application prospect. From NaBH4The mechanism of reductive desulfurization is known as NaBH4The particle size of the nickel boride produced by the reaction with the nickel salt has a great influence on the desulfurization efficiency. The smaller the particle size of the nickel boride, the larger the specific surface area of the nickel boride, the more the adsorbed organic sulfide and active hydrogen are, and the higher the desulfurization efficiency is. Conversely, the lower the desulfurization efficiency. In early studies, organic solvents such as methanol, ethanol or methanol/tetrahydrofuran were often used as NaBH4Reducing the desulfurized reaction medium. However, in these reaction media, NaBH4The nickel boride particles generated by the reaction with nickel salt have large particle size and small specific surface area, which results in low desulfurization efficiency. Moreover, the organic solvent is easy to volatilize and has high toxicity, and the problems of safety and environmental protection exist in practical application.
Disclosure of Invention
To increase NaBH4The invention introduces eutectic solvent into NaBH to solve the problem of organic solvent4And (4) reduction desulfurization.
Eutectic solvents, also known as ionic liquid analogs, are mixtures of hydrogen bond acceptors and hydrogen bond donors that are liquid at room temperature. The eutectic solvent not only has the characteristics of low vapor pressure and stable chemical property of the traditional ionic liquid, but also has the advantages of cheap and easily obtained raw materials, simple preparation process and low toxicity.
Introduction of eutectic solvents into NaBH4The reduction desulfurization process can avoid the problems of organic solvents. Moreover, more importantly, the eutectic solvent has two other functions in the desulfurization process: on one hand, the organic sulfur compound can be used as an extractant of organic sulfur compounds in fuel oil; on the other hand, the nickel boride stabilizer can be used as a stabilizer to prevent nickel boride particles from aggregating with each other, so that the nickel boride with small particle size and large specific surface area is obtained.
The purpose of the invention is realized by the following technical scheme:
a method for extracting, reducing and desulfurizing fuel oil in a eutectic solvent comprises the following steps:
mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion and adding the mixture into a reactor; then, slowly adding nickel salt into the reactor under stirring to perform desulfurization reaction; and after the reaction is finished, separating the mixture in the reactor to obtain an upper oil phase, namely the low-sulfur fuel oil.
The hydrogen bond acceptor of the synthetic eutectic solvent is tetrabutylammonium chloride, the hydrogen bond donor is polyhydric alcohols such as ethylene glycol, glycerol and polyethylene glycol, the molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is 1: 1-3, tetrabutylammonium chloride and polyethylene glycol are preferred, and the molar ratio of the tetrabutylammonium chloride to the polyethylene glycol is 1: 2.
The volume ratio of the eutectic solvent to the fuel oil is more than or equal to 0.5, and preferably (1-2) to 1.
The molar ratio of the sodium borohydride to the sulfur in the fuel oil is more than or equal to 3, and preferably (10-15) to 1.
The nickel salt is NiCl2·6H2O or Ni (AcO)2·4H2O。
The molar ratio of the nickel salt to sulfur in the fuel oil is more than or equal to 1, and preferably (2-4) to 1.
The working principle of the invention is as follows: the fuel oil is desulfurized by taking the eutectic solvent as a reaction medium and sodium borohydride as a reducing agent through an extraction-reduction combined process. As shown in fig. 1, the present invention mainly comprises the following steps:
(1) organic sulfur compounds in the fuel oil are extracted into the eutectic solvent;
(2) reacting sodium borohydride with nickel salt to generate nickel boride and active hydrogen, wherein the eutectic solvent has a stabilizing effect on the generated nickel boride;
(3) under the combined action of nickel boride and active hydrogen, organic sulfide extracted into the eutectic solvent is reduced and desulfurized to obtain corresponding hydrocarbon;
(4) the hydrocarbon obtained after desulfurization is returned to the fuel oil again.
Compared with the prior art, the invention has the following beneficial effects:
eutectic solvent as NaBH4The reaction medium in the reduction desulfurization process can avoid the problems of organic solvent, and the nickel boride particles generated by the reaction of sodium borohydride and nickel salt have small particle size and large specific surface area, thereby greatly improving the NaBH4The efficiency of the reduction desulfurization.
Drawings
Other features, objects and advantages of the invention will become more apparent upon reading of the detailed description of non-limiting embodiments with reference to the following drawings:
FIG. 1 is a schematic diagram of the desulfurization method of the present invention.
FIG. 2 shows the particle size distribution of nickel boride prepared in (a) tetrabutylammonium chloride/polyethylene glycol and (b) methanol/tetrahydrofuran medium, respectively. The particle size distribution of nickel boride prepared in tetrabutylammonium chloride/polyethylene glycol medium is between 3 and 6nm, while the particle size distribution of nickel boride prepared in methanol/tetrahydrofuran medium is between 35 and 50 nm.
FIG. 3 shows the electron micrographs of nickel boride prepared from (a) methanol/tetrahydrofuran and (b) tetrabutylammonium chloride/polyethylene glycol, respectively.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
The simulated fuel oil used in the following examples was prepared by dissolving benzothiophene in n-octane, and had a sulfur content of 500 ppm. And measuring the sulfur content in the desulfurized simulated fuel oil by using a gas chromatograph (GC-FID).
Example 1
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, polyethylene glycol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 2. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1.5: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 97.3 percent.
Example 2
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, ethylene glycol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 2. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1.5: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 95.2%.
Example 3
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, glycerol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 2. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1.5: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 90.2%.
Example 4
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, polyethylene glycol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 2. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 94.7 percent.
Example 5
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, polyethylene glycol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 2. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1.5: 1, and NaBH4The molar ratio of the sulfur to the sulfur in the fuel oil is 6: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 88.3 percent.
Example 6
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, polyethylene glycol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 2. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1.5: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; then, slowly stirring the mixtureNiCl2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 1: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 81.9 percent.
Example 7
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, polyethylene glycol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 2. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1.5: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, slowly adding Ni (AcO) under stirring2·4H2O is added into the reactor for desulfurization, and Ni (AcO) is added2·4H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 97.1 percent.
Example 8
Tetrabutylammonium chloride is used as a hydrogen bond acceptor, polyethylene glycol is used as a hydrogen bond donor, and the eutectic solvent is synthesized according to the molar ratio of 1: 1. Mixing fuel oil, eutectic solvent and NaBH4Mixing the raw materials according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of the eutectic solvent to the fuel oil is 1.5: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 85.6 percent.
Comparative example 1
Mixing fuel oil, methanol/tetrahydrofuran (3/1), and NaBH4Mixing the components in a ratio and adding the mixture into a reactor, wherein the volume ratio of methanol/tetrahydrofuran to fuel oil is 1.5: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurizationReacting, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 82.3 percent.
Comparative example 2
Mixing fuel oil, methanol/tetrahydrofuran (3/1), and NaBH4Mixing the mixture according to a certain proportion, adding the mixture into a reactor, wherein the volume ratio of methanol/tetrahydrofuran to fuel oil is 1: 1, and NaBH4The mol ratio of the sulfur to the sulfur in the fuel oil is 12: 1; subsequently, the NiCl was slowly added under stirring2·6H2Adding O into the reactor for desulfurization, adding NiCl2·6H2The molar ratio of O to sulfur in the fuel oil is 3: 1; after reacting for 60 minutes, separating the mixture in the reactor, taking the upper oil phase to measure the sulfur content, and calculating the desulfurization rate of the fuel oil to be 76.3 percent.
It can be seen that the desulfurization rates of the fuels of examples 1 to 8 are better than those of comparative example 1 to comparative example 2, wherein the desulfurization rate of the fuel of example 1 is better than that of examples 2 to 8, and example 1 is the optimal mixture ratio.
The foregoing description of specific embodiments of the present invention has been presented. It is to be understood that the present invention is not limited to the specific embodiments described above, and that various changes and modifications may be made by one skilled in the art within the scope of the appended claims without departing from the spirit of the invention.
Claims (6)
1. A method for extracting, reducing and desulfurizing fuel oil in a eutectic solvent is characterized by comprising the following steps:
mixing fuel oil, a eutectic solvent and sodium borohydride in proportion and adding the mixture into a reactor; then, slowly adding nickel salt into the reactor under stirring to perform desulfurization reaction; and after the reaction is finished, separating the mixture in the reactor to obtain an upper oil phase, namely the low-sulfur fuel oil.
2. The method according to claim 1, wherein the eutectic solvent is synthesized from a hydrogen bond acceptor and a hydrogen bond donor, the hydrogen bond acceptor is tetrabutylammonium chloride, the hydrogen bond donor is glycol, glycerol, polyethylene glycol and other polyols, and the molar ratio of the hydrogen bond acceptor to the hydrogen bond donor is 1: 1-3.
3. The method according to claim 1, wherein the volume ratio of the eutectic solvent to the fuel oil is not less than 0.5.
4. The method of claim 1, wherein the molar ratio of sodium borohydride to sulfur in the fuel oil is 3 or more.
5. The method of claim 1, wherein the nickel salt is NiCl2·6H2O or Ni (AcO)2·4H2O。
6. The method of claim 1, wherein the molar ratio of the nickel salt to sulfur in the fuel oil is greater than or equal to 1.
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Application publication date: 20200804 |