CN109694723B - Eutectic solvent and method for extracting non-alkaline nitrogen from simulated gasoline - Google Patents
Eutectic solvent and method for extracting non-alkaline nitrogen from simulated gasoline Download PDFInfo
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- 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
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Abstract
The invention relates to the technical field of extracting non-basic nitrogen from simulated gasoline, and discloses a eutectic solvent and a method for extracting non-basic nitrogen from simulated gasoline. The eutectic solvent is prepared by heating and stirring hydrogen bond acceptor quaternary ammonium salt and hydrogen bond donor 2-furanmethanol in a molar ratio of 1:2 for reaction to prepare the eutectic solvent for extracting non-alkaline nitrogen in simulated gasoline; the quaternary ammonium salt is selected from tetrabutylammonium chloride, tetrabutylammonium bromide, tetrapropylammonium chloride or tetrapropylammonium bromide. The extraction efficiency of the eutectic solvent for extracting the non-alkaline nitrogen in the simulated gasoline is high, the using amount of the extractant is low, and the extraction of the non-alkaline nitrogen in the gasoline by the eutectic solvent becomes possible to realize industrialization.
Description
Technical Field
The invention relates to a eutectic solvent and a method for extracting non-alkaline nitrogen from simulated gasoline.
Background
The fuel oil resource is one of the currently important engine fuels in China, but the existence of the nitrogen-containing compound causes serious harm to production and environment, so that the oxidation stability of the oil product is reduced, and the storage and the use performance of the oil product are influenced. Combustion of fuel containing nitrogen compounds to produce NOXAcid rain is one of the main pollution sources causing environmental pollution. In order to solve the problems of serious environmental pollution and difficult treatment, an efficient fuel oil cleaning method is urgently needed. The traditional fuel denitrification technology at present comprises the following steps: hydrodenitrogenation, adsorption denitrification, acid pickling denitrification and extraction denitrification. The hydrodenitrogenation technology has high efficiency, but the required reaction conditions are harsh, the equipment investment is large, and the operating cost is high; the adsorbent required by the adsorption denitrification technology is large in dosage, heavy in operation, difficult to reuse and the like; the acid pickling denitrification technology is not ideal for removing non-alkaline nitrides in the fuel oil; the extraction denitrification technology has simple operation, low energy consumption and good separation efficiency, so the innovation of the novel fuel oil extraction denitrification technology has important significance.
The currently and generally used extractant is an organic solvent, but the organic solvent is easy to volatilize, has high intersolubility with oil products, and pollutes the oil products, so the extractant is a non-environment-friendly extractant. The Deep Eutectic Solvent (DES) is used as an ionic liquid analogue, has the advantages of low price, easy obtaining, strong designability, wide viscosity range, small environmental pollution and the like, has been applied to the aspect of fuel oil extraction denitrification, for example, in 2015, MC Ali and the like use oxalic acid, phenylacetic acid and the like as hydrogen bond donors, choline chloride and the like as hydrogen bond acceptors to synthesize eight DES, and the DES-based fuel oil denitrification method is firstly reported, and alkaline and non-alkaline nitrogen compounds can be removed through the Deep eutectic solvent.
However, in the process of extracting fuel oil by using the eutectic solvent in the prior art, the ratio of an extracting agent to the fuel oil is mostly in the range of 2:1-1:2, the using amount of the extracting agent is large, the economic benefit is low, the extraction rate is not high, and the large-scale research and industrial production are not facilitated; meanwhile, the raw materials for synthesizing the eutectic solvent are numerous, and the types of the eutectic solvent are very many, so that the directional classification research of the eutectic solvent has limitation. The inventor initially tries a plurality of raw materials of eutectic solvents, and when the obtained extraction solvent is used for extracting non-alkaline nitrogen from simulated gasoline, the extraction efficiency of some solvents is extremely low, and some extraction solvents can only selectively extract alkaline nitrogen, so that the extraction effect on the non-alkaline nitrogen is poor; in addition, almost all extraction solvents have large solvent-oil ratio during extraction, large using amount of the extraction agent and low economic benefit, are not beneficial to large-scale research and industrial production, and the inventor almost abandons the search for the eutectic solvent for extracting the non-alkaline nitrogen from the simulated gasoline. With the progress of the test, the inventor surprisingly discovers that the eutectic solvent for extracting the non-basic nitrogen, which has the advantages of small using amount of the extracting agent and excellent extracting effect, can be obtained by adopting the hydrogen bond acceptor and the hydrogen bond donor with specific types and proportion and strictly controlling reaction parameters.
Disclosure of Invention
The invention provides a eutectic solvent and a method for extracting non-basic nitrogen from simulated gasoline, aiming at solving the problems that the extraction efficiency of extracting the non-basic nitrogen from the simulated gasoline by the eutectic solvent in the prior art is low, and the extraction cannot realize large-scale research and industrial production due to high use amount of an extracting agent.
In order to solve the technical problems, the invention adopts the following technical scheme:
a hydrogen bond acceptor quaternary ammonium salt and a hydrogen bond donor 2-furancarbinol with a molar ratio of 1:2 are heated and stirred to react to prepare the eutectic solvent for extracting the non-alkaline nitrogen in the simulated gasoline; the quaternary ammonium salt is selected from tetrabutylammonium chloride, tetrabutylammonium bromide, tetrapropylammonium chloride or tetrapropylammonium bromide.
The reaction temperature of the eutectic solvent for extracting the non-alkaline nitrogen from the simulated gasoline is 90 ℃, the reaction time is 1h, the reaction formula is shown as follows, and tetrabutylammonium chloride [ TBAC ] and 2-furancarbinol [ FAL ] are connected together through hydrogen bonds.
The invention also provides a method for extracting non-alkaline nitrogen in simulated gasoline by adopting the eutectic solvent, wherein the mass ratio of the eutectic solvent to the simulated gasoline is 1:10, and the eutectic solvent and the simulated gasoline are stirred and then used for extracting the non-alkaline nitrogen in the simulated gasoline; preferably, the stirring speed is 400-800r/min, the extraction temperature is 20-35 ℃, and the extraction time is 15-20 min.
The eutectic solvent of the present invention can be regenerated by a simple extraction method to obtain a regenerated eutectic solvent. Preferably, the preparation method of the regenerated eutectic solvent comprises the steps of adding an equal volume of water/ethanol mixture into the eutectic solvent for extracting non-alkaline nitrogen in the simulated gasoline for multiple times, adding acetonitrile for back extraction, extracting for multiple times, and performing vacuum rotary evaporation at 50 ℃ to obtain the regenerated eutectic solvent.
Compared with the extractant for extracting the non-alkaline nitrogen in the gasoline in the prior art, the eutectic solvent for extracting the non-alkaline nitrogen in the simulated gasoline provided by the invention has the greatest advantages that the non-alkaline nitrogen in the simulated gasoline can be extracted by adopting a small amount of the extractant (the solvent-oil ratio is 1:10), the extraction rate of the non-alkaline nitrogen is close to 100%, the usage amount of the extractant is small, the economic benefit is high, the extraction rate is high, large-scale research and industrial production are facilitated, and it needs to be noted that the eutectic solvent for extracting the non-alkaline nitrogen in the simulated gasoline provided by the invention has poor extraction effect on the alkaline nitrogen and can only selectively extract the non-alkaline nitrogen in the simulated gasoline; the eutectic solvent for extracting the non-alkaline nitrogen provided by the invention has strong extraction capability, and the extraction efficiency of the extractant can still be kept above 82% after 10 times of continuous extraction; the eutectic solvent for extracting the non-alkaline nitrogen provided by the invention has strong extraction capability, and after several stages of extraction, the nitrogen content can be lower than 0.1 ppm; the eutectic solvent for extracting the non-alkaline nitrogen provided by the invention can be recycled for multiple times, the regenerated extractant is subjected to extraction denitrification again, the same steps are carried out, the eutectic solvent can be recycled for 6 times, and the denitrification rate is basically unchanged.
Drawings
FIG. 1 shows [ TBAC ] in example 1][FAL]2An infrared spectrum of (1);
FIG. 2 is [ TBAC ] of example 1][FAL]2Is/are as follows1H NMR(CDCl3) A spectrogram;
FIG. 3 is [ TBAC ] of example 1][FAL]2TG-DTG spectrum of (1).
Detailed Description
The invention discloses a eutectic solvent and a method for extracting non-alkaline nitrogen from simulated gasoline, and a person skilled in the art can appropriately improve process parameters by referring to the content. It is expressly intended that all such similar substitutes and modifications which would be obvious to those skilled in the art are deemed to be included in the invention. While the methods and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications in the methods and applications described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of this invention without departing from the spirit and scope of the invention.
Example 1 preparation of a eutectic solvent simulating extraction of non-basic nitrogen in gasoline
In a 100mL three-necked flask equipped with a mechanical stirring rod and a thermometer, the molar ratio of n (hydrogen bond acceptor) n (hydrogen bond donor) to n (hydrogen bond donor) 1:2, adding 0.1mol of tetrabutylammonium chloride and 0.2mol of 2-furanmethanol, installing the system in an oil bath pan, heating to 90 ℃, and reacting for 1h under the condition of 800r/min to obtain light yellow uniform liquid, namely the extractant [ TBAC][FAL]2The extraction agent is subjected to infrared spectroscopy, nuclear magnetic resonance and thermogravimetric analysis and detection, and detection results are respectively shown in the figure 1, the figure 2 and the figure 3.
FIG. 1 shows that the stretching vibration peak of O-H is derived from the raw material [ FAL ]](b) 3354cm of curve-1Move to product [ TBAC][FAL]2(a) 3251cm of the curve-1Here, the peak pattern is clearly shifted to the low wave number region and clearly broadened, indicating that the product [ TBAC ]][FAL]2(a) Hydrogen bonds are generated in the process; at the same time, [ TBAC][FAL]2(a) Maintain its hydrogen bond donor [ FAL](b) All characteristic peaks of (a); FIG. 2 shows, [ TBAC][FAL]2(c) And [ TBAC ]](a) Neutral with N+linked-CH2Chemical shift changed from 3.37 to 3.30 due to TBAC](a) Cl in (1)-And [ FAL](b) O-H of (A) forms a hydrogen bond, N+And Cl-are weakened; at the same time, [ FAL](b) The resonance signal of O-H of (2) is changed from 2.64 to 2.59, the chemical shift is shifted to a high field, and the chemical shift is small. Shows [ TBAC][FAL]2(c) Middle [ FAL ]](b) And [ TBAC ]](a) Hydrogen bonds are formed between them. Thermogravimetric analysis was performed on the above extractant, and the analysis results are shown in fig. 3. FIG. 3 shows, [ TBAC ]][FAL]2The weight loss begins at 110 ℃ and the decomposition is completed at 239 ℃, which indicates that [ TBAC][FAL]2It is not suitable for extracting non-basic nitrogen from simulated gasoline at the temperature of more than 110 ℃.
Example 2 preparation of a eutectic solvent simulating extraction of non-basic nitrogen in gasoline
Adding 0.2mol of tetrabutylammonium bromide and 0.4mol of 2-furanmethanol into a 100mL three-neck flask provided with a mechanical stirring rod and a thermometer according to the mass ratio of n (hydrogen bond acceptor) to n (hydrogen bond donor) of 1:2, installing the system in an oil bath pot, heating to 90 ℃, and reacting for 1h under the condition of 800r/min to obtain light yellow uniform liquid, namely an extracting agent [ TBAB ]][FAL]2。
Example 3 preparation of a eutectic solvent simulating extraction of non-basic nitrogen in gasoline
In is provided withAdding 0.1mol of tetrapropylammonium chloride and 0.2mol of 2-furanmethanol into a 100mL three-neck flask with a mechanical stirring rod and a thermometer according to the mass ratio of n (hydrogen bond acceptor) to n (hydrogen bond donor) to be 1:2, installing the system in an oil bath pot, heating to 90 ℃, and reacting for 1h under the condition of 800r/min to obtain light yellow uniform liquid, namely the extractant [ TPAC ]][FAL]2。
Example 4 preparation of a eutectic solvent simulating extraction of non-basic nitrogen in gasoline
Adding 0.1mol of tetrapropylammonium bromide and 0.2mol of 2-furanmethanol into a 100mL three-neck flask provided with a mechanical stirring rod and a thermometer according to the mass ratio of n (hydrogen bond acceptor) to n (hydrogen bond donor) of 1:2, installing the system in an oil bath pot, heating to 90 ℃, and reacting for 1h under the condition of 800r/min to obtain light yellow uniform liquid, namely an extractant [ TPAB ]][FAL]2。
Example 5 method for extracting non-basic nitrogen in simulated gasoline by eutectic solvent
The eutectic solvent extractant [ TBAC ] prepared in example 1 with a mass ratio m (extractant): m (simulated oil): 1:10 was accurately weighed in a 50mL single-neck flask][FAL]2And 150ppm indole simulation oil, adding magnetons, installing the system in a water bath, magnetically stirring at the rotating speed of 800r/min for 15min at the temperature of 30 ℃, standing for 60min after the reaction is finished, taking out a proper amount of upper oil, measuring the content of residual nitrogen in the oil by using a nitrogen detector, and calculating the denitrification rate to be 99.90%.
It should be noted that the simulated gasoline has a nitride concentration of 500ppm, 300ppm or 150ppm, and the lower the nitride concentration, the greater the difficulty of extracting the non-basic nitrogen.
Example 6 method for extracting non-basic nitrogen in simulated gasoline by eutectic solvent
The eutectic solvent extractant [ TBAB ] prepared in example 2 with a mass ratio m (extractant): m (simulated oil): 1:10 was accurately weighed in a 50mL single-neck flask][FAL]2Adding 150ppm indole simulation oil, adding magneton, placing the system in water bath, magnetically stirring at 20 deg.C at 400r/min for 15min, standing for 60min after reaction, and taking out appropriate amount of upper layerAnd (3) measuring the residual nitrogen content in the oil product by using a nitrogen measuring instrument, and calculating the denitrification rate to be 99.36%.
Example 7 method for extracting non-basic nitrogen in simulated gasoline by eutectic solvent
The eutectic solvent extractant [ TPAC ] prepared in example 3 with a mass ratio m (extractant): m (simulated oil): 1:10 was accurately weighed in a 50mL single-neck flask][FAL]2And 150ppm indole simulation oil, adding magnetons, installing the system in a water bath, magnetically stirring at the rotating speed of 800r/min for 20min at the temperature of 35 ℃, standing for 60min after the reaction is finished, taking out a proper amount of upper oil, measuring the content of residual nitrogen in the oil by using a nitrogen detector, and calculating the denitrification rate to be 99.02%.
Example 8 method for extracting non-basic nitrogen in simulated gasoline by eutectic solvent
The eutectic solvent extractant [ TPAB ] prepared in example 4 with a mass ratio m (extractant): m (simulated oil): 1:10 was accurately weighed in a 50mL single-neck flask][FAL]2And 150ppm indole simulation oil, adding magnetons, installing the system in a water bath, magnetically stirring at the rotating speed of 600r/min for 18min at the temperature of 28 ℃, standing for 60min after the reaction is finished, taking out a proper amount of upper oil, measuring the content of residual nitrogen in the oil by using a nitrogen detector, and calculating the denitrification rate to be 98.46%.
Example 9 method for extracting non-basic nitrogen in simulated gasoline by eutectic solvent
The eutectic solvent extractant [ TBAC ] prepared in example 1 with a mass ratio m (extractant): m (simulated oil): 1:10 was accurately weighed in a 50mL single-neck flask][FAL]2And 500ppm indole simulation oil, adding magnetons, installing the system in a water bath, magnetically stirring at the rotation speed of 800r/min for 15min at the temperature of 20 ℃, standing for 60min after the reaction is finished, taking out a proper amount of upper oil for detection, and calculating the denitrification rate to be 99.61%.
Example 10 saturated extraction Capacity testing of eutectic solvent extractants
After the extraction denitrification of the embodiment 5 is finished once, after the upper layer oil product is separated, the simulated gasoline with the same quality as the embodiment 5 is continuously added, and the next extraction is carried out under the same conditions as the embodiment 5, wherein the quality is the same as that of the simulated gasolineStep (2) extracting agent [ TBAC ] after 10 times of continuous extraction][FAL]2The extraction efficiency can still be kept above 82%.
Example 11 testing of the Multi-stage extractability of eutectic solvent extractants
After the extractive denitrification of the gasoline in example 5 is finished, the denitrified gasoline in the upper layer is taken out and added into the fresh eutectic solvent extractant [ TBAC ] with the same mass as that of the extractant in example 5][FAL]2In the same step, the nitrogen content after 2-stage extraction can be less than 0.1 ppm.
Example 12 testing of eutectic solvent Recycling Performance
In example 5, after the oil product in the upper layer was separated at the end of extraction, the eutectic solvent [ TBAC ] was transferred to the lower layer][FAL]2Adding an equal volume of water/ethanol mixture, adding 10mL of acetonitrile for back extraction, performing back extraction for 5 times, performing vacuum suspension evaporation at 50 ℃ to finally obtain a fresh eutectic solvent, performing extraction denitrification again by using a regenerated eutectic solvent under the same condition as that of the example 5, and performing the same step, wherein the eutectic solvent is recycled for 6 times, and the denitrification rate is basically not changed.
Example 13 selection of Hydrogen bond acceptor and Hydrogen bond Donor ratios
In a 100mL three-neck flask provided with a mechanical stirring rod and a thermometer, 0.1mol of tetrabutylammonium chloride is firstly added, then 0.1mol of 2-furancarbinol and 0.3mol of 2-furancarbinol are respectively added, the two systems are arranged in an oil bath kettle, other reaction conditions are as in example 1, two kinds of uniform liquid are obtained, namely the extracting agents, and the performance detection is carried out on the two kinds of extracting agents.
When n (hydrogen bond acceptor) is 1:1, the synthesized low-temperature eutectic agent is in a solidification state at low temperature (10 ℃), the prepared extractant is used for extraction denitrification, other reaction conditions are unchanged, the quality of the extractant is reduced after the extractant is repeatedly used twice, and the extraction efficiency is obviously reduced. The possible reason is that the ratio of hydrogen bond donors in the synthesized low-temperature co-solvent is too small, the formed hydrogen bond is unstable, and part of the hydrogen bond is broken in the regeneration and recycling process of the extracting agent and cannot be recovered to the original low-temperature co-solvent after being dissolved in the ethanol solution again.
When n (hydrogen bond acceptor) is 1:3, the intersolubility of the extractant and the oil product is determined to be 6.21%, and the oil product is polluted and the quality of the oil product is influenced in the extraction process.
Comparative examples 1 to 3
In a 100mL three-neck flask equipped with a mechanical stirring rod and a thermometer, according to a hydrogen bond acceptor and a hydrogen bond donor listed in Table 1, preparing a eutectic solvent, wherein the proportion and the method are the same as those of example 1, extracting the prepared corresponding eutectic solvent and simulated gasoline according to the mass ratio m (extractant) m (simulated oil) 1:10, wherein the simulated oil is 150ppm indole simulated oil, adding magnetons, installing the system in a water bath, magnetically stirring at the rotating speed of 800r/min for 15min at the condition of 20 ℃, standing for 60min after the reaction is finished, taking out a proper amount of upper oil for detection, and calculating the corresponding denitrification rate.
TABLE 1 comparison of the denitrogenation rates of different eutectic solvents
| Comparative example | Extracting agent (hydrogen bond acceptor/hydrogen bond donor) | Denitrification rate/%) |
| Comparative example 1 | Choline chloride/urea | 30.41％ |
| Comparative example 2 | Tetrabutylammonium chloride/imidazole | 90.18％ |
| Comparative example 3 | Pyrrolidone/2-hydroxymethyl furancarbinols | 49.63％ |
The data in table 1 show that the denitrification effect of the most commonly used eutectic solvent in the prior art is not ideal, and the denitrification effect of the eutectic solvent prepared from tetrabutylammonium chloride and imidazole reaches 90%, but the extraction effect is still not ideal compared with the eutectic solvent provided by the invention.
Comparative examples 4 to 8
In a 100mL three-neck flask equipped with a mechanical stirring rod and a thermometer, according to a hydrogen bond acceptor and a hydrogen bond donor listed in table 2, an aromatic alcohol eutectic solvent is prepared according to the preparation method described in example 1, the prepared corresponding aromatic alcohol eutectic solvent and simulated gasoline are extracted according to the mass ratio m (extracting agent) m (simulated oil) 1:10, the simulated oil is 150ppm indole simulated oil, magnetons are added, the system is arranged in a water bath, the system is magnetically stirred for 15min at the rotating speed of 800r/min under the condition of 20 ℃, the system is kept still for 60min after the reaction is finished, an appropriate amount of upper layer oil is taken out for detection, the corresponding denitrification rate is calculated, the state of the eutectic solvent is detected, and the detection result is shown in table 2.
TABLE 2 aromatic alcohol eutectic extractant extraction simulated gasoline denitrification results
The data in table 2 show that the denitrification rate of the individual aromatic alcohol eutectic extractant exceeds 90%, but the synthesized extractant has high viscosity and large resistance in the mass transfer process compared with the furfuryl alcohol extractant, and is not suitable for serving as a good extractant.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. The eutectic solvent for extracting non-alkaline nitrogen from simulated gasoline is characterized in that: heating and stirring hydrogen bond acceptor quaternary ammonium salt and hydrogen bond donor 2-furancarbinol in a molar ratio of 1:2 for reaction to prepare a eutectic solvent for extracting non-alkaline nitrogen in the simulated gasoline; the quaternary ammonium salt is selected from tetrabutylammonium chloride, tetrabutylammonium bromide, tetrapropylammonium chloride or tetrapropylammonium bromide.
2. The eutectic solvent according to claim 1, wherein: the reaction temperature of the reaction is 90 ℃, and the reaction time is 1 h.
3. The method for extracting non-basic nitrogen in simulated gasoline by using the eutectic solvent as claimed in claim 1 or 2, characterized in that: the mass ratio of the eutectic solvent to the simulated gasoline is 1:10, and the eutectic solvent and the simulated gasoline are stirred and used for extracting non-alkaline nitrogen in the simulated gasoline.
4. The method of claim 3, wherein: the stirring speed is 400-800r/min, the extraction temperature is 20-35 ℃, and the extraction time is 15-20 min.
5. The method of claim 3, wherein: and regenerating the eutectic solvent by an extraction method to obtain the regenerated eutectic solvent.
6. The method of claim 3, wherein: the preparation method of the regenerated eutectic solvent comprises the steps of adding an equal volume of water/ethanol mixture into the eutectic solvent for extracting non-alkaline nitrogen in the simulated gasoline for multiple times, adding acetonitrile for back extraction, extracting for multiple times, and performing vacuum rotary evaporation at 50 ℃ to obtain the regenerated eutectic solvent.
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| CN104762100A (en) * | 2015-03-30 | 2015-07-08 | 浙江大学 | Method for removing nitrogen-containing compounds in oil products by virtue of eutectic solvent extraction |
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