CN114106870A - Method for extracting and denitrifying fuel oil by using triethylene glycol-metal nitrate composite solvent - Google Patents
Method for extracting and denitrifying fuel oil by using triethylene glycol-metal nitrate composite solvent Download PDFInfo
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- CN114106870A CN114106870A CN202111190296.4A CN202111190296A CN114106870A CN 114106870 A CN114106870 A CN 114106870A CN 202111190296 A CN202111190296 A CN 202111190296A CN 114106870 A CN114106870 A CN 114106870A
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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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
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Abstract
The invention relates to a method for extracting and denitrifying fuel oil by using a triethylene glycol-metal nitrate composite solvent. The method comprises the steps of uniformly mixing metal nitrate and triethylene glycol according to a specific proportion to obtain a composite extracting agent, mixing the composite extracting agent with fuel oil under the stirring condition of 20-50 ℃ for extraction, and obtaining denitrified fuel oil after standing, layering and liquid-liquid separation operations, wherein a large number of test results show that the denitrification rate of the method is up to 99%. The invention utilizes the strong Lewis acidity of the metal nitrate to ensure that the composite extractant and organic nitrogen in the fuel oil have stronger Lewis acid-base complex reaction, thereby obviously improving the denitrification performance. The novel composite extracting agent has the advantages of high selectivity, thorough and rapid denitrification, low cost and the like, and has wide industrial application prospect.
Description
Technical Field
The invention relates to the technical field of petrochemical industry and environmental protection, in particular to a method for extracting and denitrifying fuel oil by using a triethylene glycol-metal nitrate composite solvent.
Background
With the rapid development of economy in China, the demand of fuel oil such as gasoline and diesel oil is greatly increased. Organic nitrogen in fuel oil not only affects the chromaticity and the oxidation stability of products, but also releases a large amount of nitrogen oxides in the combustion process, and once the polluting gases are discharged into the atmosphere, haze (PM2.5) is easily formed to cause serious environmental problems, so that the nitrogen in the fuel oil needs to be removed as far as possible. The analysis result shows that the organic nitrogen compounds in the fuel oil mainly comprise pyridine, quinoline, pyrrole, indole and the like. Hydrogenation technology is generally used for removing nitrogen in fuel oil in industry, but hydrogenation reaction conditions are harsh (high temperature and high pressure), requirements on catalysts are high, equipment investment and operation cost are too high, and the defects and the disadvantages cause many limitations in industrial production.
In order to make the denitrification process conditions of the fuel oil milder, some alternative non-hydrodenitrification technologies such as extraction, adsorption, oxidation, photocatalysis and the like are generated. The extraction process can denitrify the fuel under mild conditions, and is simple to operate, so that the extraction process is widely concerned. Therefore, the inventor group has already proposed a method for extracting and denitrifying from fuel oil by using polyethylene glycol and modified compounds thereof in 2017 (see chinese patent CN107937013B), wherein ether bonds and hydroxyl groups in the polyethylene glycol and the modified compounds thereof can react with N in the fuel oil, but the strength of the reaction is not sufficient, so that the denitrification performance and selectivity still need to be improved, and meanwhile, the polyethylene glycol dicarboxylic acid shows excellent denitrification performance due to strong carboxylic acid. Although polyethylene glycol is cheaper, the denitrification performance is relatively poor, and although the denitrification performance of polyethylene glycol dicarboxylic acid is good, the cost of raw materials is high, and the adverse factors limit the industrial application prospect of polyethylene glycol and modified compounds thereof in the aspect of fuel oil denitrification. The inventor group has developed a series of different fuel oil denitrification extractants, including polyetheramine-formic acid (CN109355091B), polyethylene glycol dicarboxylic acid-quaternary ammonium salt (CN109181747B), polyethylene imine (CN108059972B) and the like.
On the basis, the inventor continues to develop continuous efforts and successfully develops a fuel oil extraction denitrification method based on a triethylene glycol-metal nitrate composite solvent. According to the method, the metal nitrate is uniformly dispersed in the triethylene glycol, and the defect of insufficient acidity of pure triethylene glycol is well overcome by utilizing the characteristics of strong Lewis acidity and large polarity of the metal nitrate, so that the obtained triethylene glycol-metal nitrate composite solvent and basic nitrogen in fuel oil can have strong Lewis acid-base complex reaction, and further the removal of nitride (especially basic nitrogen) in the fuel oil is promoted and higher denitrification rate is realized.
Disclosure of Invention
The invention aims to provide a fuel denitrification composite extracting agent, which comprises triethylene glycol and metal nitrate.
Further, the metal nitrate is at least one of silver nitrate, iron nitrate, cobalt nitrate, nickel nitrate, copper nitrate, zinc nitrate, palladium nitrate, chromium nitrate and manganese nitrate. The selected metal salt not only needs to have stronger Lewis acidity, but also needs to have better intersolubility with triethylene glycol, thereby excluding sulfate and other metal salts.
Furthermore, the metal nitrate is free of crystalline water and free water, and the material is dried thoroughly before use.
Furthermore, the mass fraction of the metal nitrate in the composite extracting agent is 0.5-3%.
Furthermore, the composite extracting agent is formed by mixing triethylene glycol and metal nitrate, namely a double-component.
Another object of the present invention is to provide a method for removing nitrogen from fuel oil by using the above composite extractant, which comprises the following steps: and mixing the composite extracting agent with fuel oil, extracting, and standing for liquid separation.
Furthermore, the mass ratio of the composite extracting agent to the fuel oil is 0.02-2.
Furthermore, the mol ratio of the metal nitrate in the composite extracting agent to the N in the fuel oil is 0.5-4.
Further, the extraction temperature is 20-50 ℃, the extraction time is 5-30min, and stirring is kept during the extraction process.
Furthermore, the boiling range of the fuel oil is 70-350 ℃, and the nitrogen content is 50-600 mu g/g.
The invention adopts the composite solvent of triethylene glycol and metal nitrate as the extracting agent, and the strong Lewis acidity of the metal nitrate is utilized to ensure that the composite solvent can rapidly generate strong Lewis acid-base complex reaction with organic nitrogen, thereby realizing the high-efficiency removal of the organic nitrogen in the fuel oil. Compared with the prior art, the beneficial effects of the invention are mainly embodied in the following aspects: (1) a proper amount of metal nitrate is highly dispersed in triethylene glycol, can quickly and efficiently generate stronger complexation with organic nitrogen in fuel oil, has the denitrogenation rate up to 99 percent, and shows high selectivity; (2) the whole extraction denitrification operation condition is mild, high temperature and high pressure are not needed, the time for achieving a better denitrification effect is short, and the denitrification efficiency is high; (3) the triethylene glycol serving as the raw material is low in cost, the addition amount of the metal nitrate is low, the production and use cost of the whole composite extracting agent is moderate comprehensively, and the application prospect is good.
Detailed Description
In order to make those skilled in the art fully understand the technical solutions and advantages of the present invention, the following embodiments are further described.
Example 1
A composite extracting agent: the silver nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the silver nitrate is 2.4%. If the metal nitrate raw material contains bound water or absorbs moisture in the air, it is necessary to perform a water removal treatment before use.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing pyrrole and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 2. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 3.25 mu g/g, the calculated denitrification rate is 99.35 percent, and the mass distribution coefficient is 75.22.
Example 2
A composite extracting agent: the silver nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the silver nitrate is 2.4%.
Fuel oil: indole and n-octane were mixed to form a simulated gasoline with an initial nitrogen content of 500 μ g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 2. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 1.93 mu g/g, the calculated denitrification rate is 99.61 percent, and the mass distribution coefficient is 126.98.
Example 3
A composite extracting agent: the silver nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the silver nitrate is 2.4%.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing pyridine and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 2. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 4.11 mu g/g, the calculated denitrification rate is 99.18%, and the mass distribution coefficient is 59.48.
Example 4
A composite extracting agent: the catalyst comprises a uniform mixture of cobalt nitrate and triethylene glycol, wherein the mass fraction of the cobalt nitrate is 2.6%.
Fuel oil: indole and n-octane were mixed to form a simulated gasoline with an initial nitrogen content of 500 μ g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 2.69 mu g/g, the calculated denitrification rate is 99.46%, and the mass distribution coefficient is 180.12.
Example 5
A composite extracting agent: the catalyst comprises a uniform mixture of cobalt nitrate and triethylene glycol, wherein the mass fraction of the cobalt nitrate is 2.6%.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing pyridine and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 12.9 mu g/g, the calculated denitrification rate is 97.42 percent, and the mass distribution coefficient is 36.76.
Example 6
A composite extracting agent: the nickel nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the nickel nitrate is 2.6%.
Fuel oil: indole and n-octane were mixed to form a simulated gasoline with an initial nitrogen content of 500 μ g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 3.33 mug/g, the calculated denitrification rate is 99.33%, and the mass distribution coefficient is 145.99.
Example 7
A composite extracting agent: the nickel nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the nickel nitrate is 2.6%.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing pyrrole and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 6.56 mu g/g, the calculated denitrification rate is 98.69 percent, and the mass distribution coefficient is 73.89.
Example 8
A composite extracting agent: the zinc nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the zinc nitrate is 2.7%.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing pyridine and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 2. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 6.14 mu g/g, the calculated denitrification rate is 98.77 percent, and the mass distribution coefficient is 39.47.
Example 9
A composite extracting agent: the zinc nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the zinc nitrate is 1.4%.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing pyrrole and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 7.85 mu g/g, the calculated denitrification rate is 98.43 percent, and the mass distribution coefficient is 61.03.
Example 10
A composite extracting agent: the zinc nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the zinc nitrate is 2.7%.
Fuel oil: the initial nitrogen content of the catalytic cracking diesel oil produced by a certain refinery is controlled to be 282 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 80.36 mu g/g, the calculated denitrification rate is 71.96 percent, and the mass distribution coefficient is 2.49.
Example 11
A composite extracting agent: the nickel nitrate and the triethylene glycol are uniformly mixed, wherein the mass fraction of the nickel nitrate is 2.7%.
Fuel oil: the initial nitrogen content of the catalytic cracking diesel oil produced by a certain refinery is controlled to be 282 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 79.85 mu g/g, the calculated denitrification rate is 72.14 percent, and the mass distribution coefficient is 2.51.
Experiments show that in addition to the metal nitrates such as silver nitrate, cobalt nitrate, nickel nitrate, zinc nitrate and the like, organic nitrogen in simulated oil and actual fuel oil can be efficiently and quickly removed after the iron nitrate, the copper nitrate, the palladium nitrate, the chromium nitrate, the manganese nitrate and the triethylene glycol are mixed according to a specific proportion.
In addition, in order to further illustrate the denitrification effect of the compound extractant, a comparative experiment is also carried out by taking pure triethylene glycol as the extractant.
Comparative example 1
Extracting agent: pure triethylene glycol.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing pyridine and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 77.49 mu g/g, the calculated denitrification rate is 84.5 percent, and the mass distribution coefficient is 5.33.
Comparative example 2
Extracting agent: pure triethylene glycol.
Fuel oil: the initial nitrogen content of the simulated gasoline formed by mixing quinoline and normal octane is controlled to be 500 mu g/g.
The process conditions are as follows: the extraction temperature is 30 ℃, the extraction time is 30min, and the mixing mass ratio of the extracting agent to the fuel oil is 1. Stirring is carried out continuously in the extraction process, standing and layering are carried out after extraction is finished, and liquid-liquid separation is carried out to obtain a denitrified oil phase and a nitrogen-enriched extract phase.
After the extraction operation, the nitrogen content in the fuel oil is reduced to 71.18 mu g/g, the calculated denitrification rate is 85.76 percent, and the mass distribution coefficient is 5.92.
Claims (10)
1. The fuel denitrification composite extractant is characterized in that: the composite extractant comprises triethylene glycol and metal nitrate.
2. The fuel denitrification composite extractant of claim 1, which is characterized in that: the metal nitrate is at least one of silver nitrate, ferric nitrate, cobalt nitrate, nickel nitrate, copper nitrate, zinc nitrate, palladium nitrate, chromium nitrate and manganese nitrate.
3. The fuel denitrification composite extractant of claim 1, which is characterized in that: the metal nitrate is free of crystalline water and free water.
4. The fuel denitrification composite extractant of claim 1, which is characterized in that: the mass fraction of the metal nitrate in the composite extracting agent is 0.5-3%.
5. The fuel denitrification composite extractant of claim 1, which is characterized in that: the composite extractant is formed by mixing triethylene glycol and metal nitrate.
6. A method for removing nitrogen from fuel oil by using the composite extractant of any one of claims 1 to 5, characterized in that the method comprises the following steps: and mixing the composite extracting agent with fuel oil, extracting, and standing for liquid separation.
7. The method of claim 6, wherein: the mass ratio of the composite extractant to the fuel oil is 0.02-2.
8. The method of claim 6, wherein: the mol ratio of the metal nitrate in the composite extractant to the N in the fuel oil is 0.5-4.
9. The method of claim 6, wherein: the extraction temperature is 20-50 deg.C, the extraction time is 5-30min, and stirring is kept during the extraction process.
10. The method of claim 6, wherein: the boiling range of the fuel oil is 70-350 ℃, and the nitrogen content is 50-600 mu g/g.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1583968A (en) * | 2004-06-02 | 2005-02-23 | 石油大学(华东) | Gasoline and diesel denitrifying method |
| CN103000381A (en) * | 2011-09-16 | 2013-03-27 | 天津城市建设学院 | Method for manufacturing ZnO/CuInS<2> nanorod film with core-shell structure |
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- 2021-10-13 CN CN202111190296.4A patent/CN114106870B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1583968A (en) * | 2004-06-02 | 2005-02-23 | 石油大学(华东) | Gasoline and diesel denitrifying method |
| CN103000381A (en) * | 2011-09-16 | 2013-03-27 | 天津城市建设学院 | Method for manufacturing ZnO/CuInS<2> nanorod film with core-shell structure |
Non-Patent Citations (2)
| Title |
|---|
| 刘淑芝等: "络合萃取脱除FCC柴油中的碱性氮化物", 《化工进展》 * |
| 齐江等: "石油产品溶剂脱氮研究进展", 《现代化工》 * |
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