CN113109413A - Structure analysis method of petroleum nitrogen-containing compound and application thereof - Google Patents
Structure analysis method of petroleum nitrogen-containing compound and application thereof Download PDFInfo
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Abstract
The invention provides a structure analysis method of a petroleum nitrogen-containing compound and application thereof. The method comprises the following steps: dissolving a petroleum component in a fully deuterated solvent, and then adding an additive to obtain a solution to be analyzed; injecting the solution to be analyzed into an ionization source, and ionizing by using an electrospray ionization source; and characterizing the ionized compound by using a Fourier transform ion cyclotron resonance mass spectrometer to obtain the distribution of various deuterated nitrogen-containing compounds, thereby realizing the structural analysis of petroleum nitrogen-containing compounds. The method for analyzing the structure of the petroleum nitrogen-containing compound can quickly, simply and conveniently characterize the structure of the functional group of the petroleum nitrogen-containing compound to obtain the composition distribution of primary amine, cyclic amine and pyridine compounds in the alkaline nitride, has the characteristics of extremely high nitride reaction efficiency and easy spectrogram analysis, and is suitable for analyzing a petroleum sample which contains the nitride and is not polluted.
Description
Technical Field
The invention relates to a structure analysis method of a petroleum nitrogen-containing compound and application thereof, belonging to the technical field of petroleum analysis.
Background
Although the content of nitrogen-containing compounds in petroleum is small, the nitrogen-containing compounds have adverse effects on the processing of petroleum and the service performance of products, so that the catalyst is poisoned and inactivated, the stability of oil products is reduced, and nitrogen oxides generated by combustion pollute the environment. The hydrogenation of petroleum is an important way for removing nitride, and the analysis of nitrogen-containing compounds has important significance for the hydrogenation removal of nitride. Because the composition of petroleum molecules is quite complex, their characterization is difficult. The ideal characterization process needs to satisfy three requirements: (1) the nitride reaction efficiency is extremely high; (2) does not contaminate or damage the instrument; (3) the spectrogram analysis is easy. At present, the analysis of molecular composition has become mature under the development of high resolution mass spectrometry with high resolution and high accuracy. The molecular structure is an important factor for determining the physicochemical properties of oil products, and therefore, molecular structure analysis is performed on the basis of molecular composition analysis.
The structure of nitrogen-containing compounds in petroleum components is analyzed, and the mass spectrometry dissociation technology, the chemical derivatization method and the hydrogen-deuterium exchange are mainly adopted at present. Although the parent ion structure can be presumed according to the fragment structure, the analysis of the oil structure is limited to simple judgment of the core form and the length of the side chain, and the fragment information is difficult to read, and cannot directly provide the specific structure information of the oil molecule. The chemical derivatization method is to identify the functional groups of the compound by utilizing the difference of the reaction between different functional groups and derivatization reagents. However, no relatively mature derivatization method is applied to the analysis of the structure of the petroleum nitrogen-containing compound at present, and because the composition of a petroleum system is relatively complex, the reaction and separation process of derivatization is relatively complex, and meanwhile, the derivatization method of the petroleum system has low efficiency and is a problem which cannot be ignored. Deuterium exchange refers to the process of replacing a labile hydrogen atom exposed to a deuterated reagent with a deuterium atom, resulting in an increase in molecular mass. However, for the analysis of nitrides in petroleum, atmospheric pressure photoionization sources or atmospheric pressure chemical ionization sources have been frequently used in the past research. However, these two ionization sources will generate a large number of molecular ion peaks, which increases the difficulty of spectrogram analysis, and the exchange efficiency of hydrogen and deuterium is low, which is easy to generate wrong interpretation for the spectrogram. In the process of combining the prior hydrogen deuterium exchange and high-resolution mass spectrometry, the change of the functional group of the basic nitrogen-containing compound in a heavy oil processing system is not researched.
The research on the functional groups of nitrogen-containing compounds in petroleum and the change of the nitrogen-containing compounds before and after processing needs a method which has extremely high nitride reaction efficiency, does not pollute or damage instruments and has accurate and easy spectrogram analysis.
Disclosure of Invention
In order to solve the above-mentioned disadvantages and shortcomings, the present invention aims to provide a method for analyzing the structure of a petroleum nitrogen-containing compound. The method can effectively represent the structure of nitrogen-containing compounds in petroleum and can completely reflect the change rule of various nitrides in the processing process.
In order to achieve the above purpose, the present invention provides a method for analyzing the structure of a petroleum nitrogen-containing compound, which is a method for analyzing basic nitrogen-containing compound functional groups in petroleum components by using deuterium exchange and electrospray ionization source high-resolution mass spectrometry, and comprises the following steps (the specific process is shown in fig. 1):
dissolving a petroleum component in a fully deuterated solvent, adding an additive to obtain a solution to be resolved, and promoting the dissolution by ultrasound;
injecting a solution (namely a sample) to be analyzed into an ionization source, and ionizing by using an electrospray ionization source;
and characterizing the ionized compound by using a Fourier transform ion cyclotron resonance mass spectrometer to obtain the distribution of various deuterated nitrogen-containing compounds, thereby realizing the structural analysis of petroleum nitrogen-containing compounds.
According to the specific embodiment of the invention, the distribution of the deuterated nitrogen-containing compounds comprises the molecular composition of the primary amine, the cyclic amine and the pyridine compounds in the basic nitrogen-containing compounds, namely, the method provided by the invention can realize the characterization of the molecular composition of the primary amine, the cyclic amine and/or the pyridine compounds in the basic nitrogen-containing compounds.
According to a particular embodiment of the invention, the petroleum component to which the above process is applied comprises uncontaminated crude oil or processed products thereof and is used in an amount of 0.1 to 0.2 mg.
According to a particular embodiment of the invention, the total nitrogen content of the above-mentioned petroleum component is greater than 0.07 wt%.
According to a specific embodiment of the present invention, the deuterated solvent is preferably a mixture of deuterated toluene and deuterated methanol in a volume ratio of 1:1 to 2:3, and the total amount of the deuterated solvent used is 0.5 to 1 mL.
According to a specific embodiment of the present invention, the additive is preferably a combination of deuterated formic acid and heavy water, which are used in an amount of 10 to 20 μ L, respectively.
According to a specific embodiment of the present invention, wherein the purity of the deuterated toluene is not less than 99.94 wt.%, the purity of the deuterated methanol is not less than 99.8 wt.%, the purity of the deuterated formic acid is not less than 95 wt.%, and the purity of the heavy water is not less than 99.9 wt.%.
According to the specific embodiment of the invention, the injection speed of the solution to be analyzed into the ionization source is preferably 250-300 μ L/h.
According to a particular embodiment of the present invention, preferably, the electrospray ionization source is to ionize a compound in positive ion mode.
The structure analysis method of the petroleum nitrogen-containing compound provided by the invention combines hydrogen and deuterium exchange with a positive ion electric spray ionization source Fourier transform ion cyclotron resonance mass spectrometer.
The invention also provides the application of the method in the structural analysis of the nitrogen-containing compounds of petroleum or processed products thereof; preferably primary amines, cyclic amines and/or pyridines in the basic nitrogen-containing compounds.
The structure analysis method of the petroleum nitrogen-containing compound provided by the invention can realize the analysis of the structure characteristics of the nitrogen-containing compound in petroleum and processed products thereof, and particularly the representation of the molecular composition of primary amine, cyclic amine and/or pyridine compounds in the basic nitrogen-containing compound.
Drawings
FIG. 1 is a schematic diagram of a method for analyzing a structure of a nitrogen-containing compound according to the present invention;
FIGS. 2 a-2 b are the mass spectrum and relative abundance of compound types in example 1, respectively;
FIGS. 3a to 3c are the DBE and carbon number distribution diagrams and the presumed core structures of the pyrrole, cyclic amine and primary amine compounds in example 1, respectively;
FIGS. 4 a-4 d are mass spectra and relative abundance of compound types in example 2, respectively;
FIG. 5 is a DBE and carbon number distribution diagram and a structure of pyrrole and cyclic amine compounds in example 2;
FIG. 6 is a mass spectrum and relative abundance of compound types in example 3;
FIG. 7 is a diagram showing a carbon number distribution and a structure presumed for DBE in example 3;
FIG. 8 is a mass spectrum of example 4.
Detailed Description
The technical solutions of the present invention will be described in detail below in order to clearly understand the technical features, objects, and advantages of the present invention, but the present invention is not limited to the practical scope of the present invention.
The model of the Fourier transform ion cyclotron resonance mass spectrometer used in the embodiment of the invention is Bruker Apexultra, and the magnetic field intensity is 9.4T.
In the examples of the present invention, the specific instrument parameters are as follows:
injector set speed: 250 mu L/h;
ionization source needle voltage: -4500V;
capillary induced voltage: -5000V;
mass spectrum collision cell accumulation time: 0.5 s;
accumulated collection times of mass spectrum: and 64 times.
Example 1
The embodiment provides a method for analyzing the structure of hydrogenation product oil of coker gas oil, which comprises the following specific steps:
firstly, weighing 0.1mg of coking gas oil hydrogenation product with total nitrogen content of 709ppm, then dissolving the coking gas oil hydrogenation product in 0.5ml of mixed solution of deuterated toluene and deuterated methanol, wherein the volume ratio of the two solvents is 2:3, then adding 10 mu L of deuterated formic acid and 10 mu L of heavy water, and carrying out ultrasonic treatment on the prepared solution to promote dissolution;
injecting a sample into an ionization source through a sample injector, ionizing in an electrospray ionization source positive ion mode, obtaining the molecular composition of the sample through a Fourier transform ion cyclotron resonance mass spectrometer, and analyzing the obtained spectrogram. The mass spectra and relative abundance of compound types are shown in fig. 2a and 2 b.
Mass spectrometer flight times used in this example: 1.0 ms;
after the analysis is finished, the obtained spectrogram is analyzed and processed, the pyridine compound is represented as N1D1, the cyclic amine compound is represented as N1D2, and the primary amine compound is represented as N1D3, so that the distribution of nitrides with different functional groups in the hydrogenation product of the coker gas oil can be obtained, and the DBE and carbon number distribution diagrams of the pyrrole, cyclic amine and primary amine compounds and the presumed core structure are shown in figures 3 a-3 c.
Example 2
The embodiment provides a method for analyzing the structures of vacuum residue and hydrogenation product oil thereof, which comprises the following steps:
firstly, weighing 0.1mg of vacuum residue with total nitrogen content of 3200ppm and hydrogenation products of the vacuum residue, wherein the total nitrogen content is 2700ppm, then dissolving the vacuum residue and the hydrogenation products of the vacuum residue in a mixed solution of deuterated toluene and deuterated methanol, wherein the volume ratio of the two solvents is 2:3, then adding 10 mu L of deuterated formic acid and 10 mu L of heavy water, and carrying out ultrasonic treatment on the prepared solution to promote the dissolution;
injecting a sample into an ionization source through a sample injector, ionizing in an electrospray ionization source positive ion mode, obtaining the molecular composition of the sample through a Fourier transform ion cyclotron resonance mass spectrometer, and analyzing the obtained spectrogram. The mass spectrum and the relative abundance of the compound types of the vacuum residue are shown in fig. 4a and 4 b; the mass spectrum and the relative abundance of the compound types of the vacuum residue hydrogenation product are shown in fig. 4c and 4 d.
Mass spectrometer flight times used in this example: 1.2 ms;
after the analysis is finished, the obtained spectrogram shows that the pyridine compound is represented as N1D1, the cyclic amine compound is represented as N1D2 and the primary amine compound is represented as N1D3 according to the deuteration rule of the nitrogen-containing compound, the structures of the nitrogen-containing compound in the vacuum residue oil and the hydrogenation product of the vacuum residue oil can be analyzed, the change of the composition distribution of the nitrogen-containing compound containing different functional groups before and after hydrogenation can be obtained, and the DBE and carbon number distribution diagrams and the presumed structures of the pyrrole and the cyclic amine compound are shown in figure 5. As can be seen from fig. 5: only pyridine compounds are observed in the raw materials, and a large amount of cyclic amine compounds appear in the products after hydrotreating.
Example 3
The embodiment provides a method for analyzing the structure of vacuum residue and continuous hydrogenation product oil thereof, which comprises the following steps:
firstly, 0.1mg of vacuum residue with total nitrogen content of 5272ppm and four continuous hydrogenation products R1, R2, R3 and R4 of the vacuum residue with total nitrogen content of 5813ppm, 5468ppm, 4159ppm and 2693ppm are respectively weighed, and then dissolved in a mixed solution of deuterium substituted toluene and deuterium substituted methanol, the volume ratio of the two solvents is 2:3, and 10 mu L of deuterium substituted formic acid and 10 mu L of heavy water are added. The prepared solution was subjected to sonication to facilitate dissolution. Injecting a sample into an ionization source through a sample injector, ionizing in an electrospray ionization source positive ion mode, obtaining the molecular composition of the sample through a Fourier transform ion cyclotron resonance mass spectrometer, and analyzing the obtained spectrogram. The mass spectra and the compound type relative abundance maps of the vacuum residue and four continuous hydrogenation products R1, R2, R3 and R4 of the vacuum residue are respectively shown in FIG. 6.
Mass spectrometer flight times used in this example: 1.2 ms;
after the analysis is finished, the obtained spectrogram is analyzed and processed, the pyridine compound is represented as N1D1, the cyclic amine compound is represented as N1D2, and the primary amine compound is represented as N1D3, so that the composition distribution of nitrogen-containing compounds containing different functional groups in the vacuum residue and the hydrogenation product thereof can be analyzed, the change of the cyclic amine nitrogen compound in the continuous hydrogenation process is obtained, and the DBE, the carbon number distribution diagram and the presumed structure of the cyclic amine compound are shown in figure 7. As can be seen from fig. 7: in the continuous hydrogenation process, the cyclic amine compounds show a trend of increasing and decreasing gradually, and the processes of cyclic amine hydrogenation saturation, short side chain compound hydrogenation removal and the like of the cyclic amine compounds can be clearly observed.
Example 4
The embodiment provides a structure analysis method of a nitrogen-containing model compound, which comprises the following specific steps:
the model compound is dissolved in a mixed solvent of deuterated toluene and deuterated methanol, the volume ratio of the two solvents is 2:3, and the model compound is divided into four groups for comparative experiments:
(1) dissolving in a solvent of deuterated toluene methanol, and adding no additive (DT-DM);
(2) adding deuterated formic acid (10 μ L per 0.5mL solvent) (DT-DM + DCOOD) to the solution;
(3) to the solution was added heavy water (10. mu.L per 0.5mL of solvent) (DT-DM + D)2O)；
(4) Simultaneously adding deuterated formic acid and heavy water (DT-DM + DCOOD + D)2O)。
Each model compound concentration was 10-7And (3) performing ultrasonic assisted dissolution on the prepared solution by mol/L.
The sample is injected into the ionization source by a sample injector and ionized in electrospray ionization source positive ion mode.
The molecular composition was obtained by high resolution mass spectrometry, and the obtained spectra were analyzed, and the obtained spectra under each condition are shown in fig. 8.
As can be seen in fig. 8: the addition of the heavy water and the deuterated formic acid reduces the relative abundance of incomplete deuterated peaks in the deuterated products, thereby greatly reducing the difficulty of spectrogram analysis.
After the analysis is finished, analyzing the spectrogram and processing data to obtain model compounds of DT-DM, DT-DM + D2O, DT-DM + DCOOD and DT-DM + DCOOD + D2O systemThe relative abundance of the deuterated compound and the calculated hydrogen-deuterium exchange efficiency using equation (1) are shown in table 1.
Wherein i is the number of exchange of hydrogen and deuterium, hiThe peak intensity corresponding to i, and N is the total number of active hydrogen.
TABLE 1
As can be seen from table 1: the addition of the heavy water and the deuterated formic acid can improve the hydrogen and deuterium exchange efficiency of various nitrogen-containing compounds to more than 90 percent.
Claims (10)
1. A method for analyzing the structure of a nitrogen-containing compound in petroleum comprises the following steps:
dissolving a petroleum component in a fully deuterated solvent, and adding an additive to obtain a solution to be resolved;
injecting the solution to be analyzed into an ionization source, and ionizing by using an electrospray ionization source;
and characterizing the ionized compound by using a Fourier transform ion cyclotron resonance mass spectrometer to obtain the distribution of various deuterated nitrogen-containing compounds, thereby realizing the structural analysis of petroleum nitrogen-containing compounds.
2. The method of claim 1, wherein the deuterated class of nitrogen-containing compound distribution comprises a molecular composition of primary amines, cyclic amines, and/or pyridines in the basic nitrogen-containing compound.
3. The method of claim 1 wherein the petroleum comprises uncontaminated crude oil or processed products thereof in an amount of 0.1 to 0.2 mg.
4. A method according to any one of claims 1 to 3 wherein the total nitrogen content of the petroleum component is greater than 0.07 wt%.
5. The method of claim 1, wherein the deuterated solvent is a mixture of deuterated toluene and deuterated methanol in a volume ratio of 1:1-2:3, and the total amount of the deuterated solvent is 0.5-1 mL.
6. The method of claim 1 or 5, wherein the additive is a combination of deuterated formic acid and deuterium oxide, each in an amount of 10-20 μ L.
7. The method of claim 6, wherein the deuterated toluene has a purity of not less than 99.94 wt.%, the deuterated methanol has a purity of not less than 99.8 wt.%, the deuterated formic acid has a purity of not less than 95 wt.%, and the heavy water has a purity of not less than 99.9 wt.%.
8. The method as claimed in claim 1, wherein the injection speed of the solution to be analyzed into the ionization source is 250-300 μ L/h.
9. The method of claim 1, wherein the electrospray ionization source ionizes a compound in a positive ion mode.
10. Use of the method for structural analysis of a nitrogen-containing compound according to any one of claims 1 to 9 for structural analysis of a nitrogen-containing compound of petroleum or a processed product thereof; preferably primary amines, cyclic amines and/or pyridines in the basic nitrogen-containing compounds.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130161502A1 (en) * | 2010-05-12 | 2013-06-27 | Schlumberger Technology Corporation | Method for analysis of the chemical composition of the heavy fraction of petroleum |
| US20130306853A1 (en) * | 2012-05-17 | 2013-11-21 | Martin Eastwood | Analyzing target analytes in a sample using mass spectroscopy |
| US9366661B1 (en) * | 2015-03-20 | 2016-06-14 | Authentix, Inc. | Fuel markers and methods of producing and using same |
| US20170297971A1 (en) * | 2015-11-20 | 2017-10-19 | Korea Institute Of Petroleum Management | Method for marking oil products and marker composition for oil products |
| US20190128845A1 (en) * | 2017-11-02 | 2019-05-02 | Ohio State Innovation Foundation | Imms method for petroleum feedstock evaluation |
| CN110128232A (en) * | 2019-05-16 | 2019-08-16 | 湖州中科颐格生物科技有限公司 | A method of it is introduced in organic matter deuterated |
-
2019
- 2019-12-25 CN CN201911356089.4A patent/CN113109413B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130161502A1 (en) * | 2010-05-12 | 2013-06-27 | Schlumberger Technology Corporation | Method for analysis of the chemical composition of the heavy fraction of petroleum |
| US20130306853A1 (en) * | 2012-05-17 | 2013-11-21 | Martin Eastwood | Analyzing target analytes in a sample using mass spectroscopy |
| US9366661B1 (en) * | 2015-03-20 | 2016-06-14 | Authentix, Inc. | Fuel markers and methods of producing and using same |
| US20170297971A1 (en) * | 2015-11-20 | 2017-10-19 | Korea Institute Of Petroleum Management | Method for marking oil products and marker composition for oil products |
| US20190128845A1 (en) * | 2017-11-02 | 2019-05-02 | Ohio State Innovation Foundation | Imms method for petroleum feedstock evaluation |
| CN110128232A (en) * | 2019-05-16 | 2019-08-16 | 湖州中科颐格生物科技有限公司 | A method of it is introduced in organic matter deuterated |
Non-Patent Citations (4)
| Title |
|---|
| RYAN P. RODGERS, CHRISTOPHER L. HENDRICKSON,KUANGNAN QIAN: "Reading Chemical Fine Print: Resolution and Identification of 3000 Nitrogen-Containing Aromatic Compounds from a Single Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrum of Heavy Petroleum Crude Oil", 《ENERGY & FUELS》 * |
| YUNJU CHO、ARIF AHMED AND SUNGHWAN KIM: "Application of Atmospheric Pressure Photo Ionization Hydrogen/Deuterium Exchange High-Resolution Mass Spectrometry for the Molecular Level Speciation of Nitrogen Compounds in Heavy Crude oils", 《ANALYTICAL CHEMISTRY》 * |
| YURY KOSTYUKEVICH、ALEXEY KONONIKHIN、IGOR POPOV AND E NIKOLAEV: "In-ESI Source Hydrogen/Deuterium Exchange of Carbohydrate Ions", 《ANALYTICAL CHEMISTRY》 * |
| YURY KOSTYUKEVICH、ALEXEY KONONIKHIN、IGOR POPOV AND E NIKOLAEV: "Simple Atmospheric Hydrogen/Deuterium Exchange Method for Enumeration of Labile Hydrogens by Electrospray Ionization Mass Spectrometry", 《ANALYTICAL CHEMISTRY》 * |
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