Analysis of Distribution and Structures of Heteroatom Compounds in Asphaltene of Medium/Low Temperature Coal Tar by Negative Anion Mode ESI FT-ICR MS
Abstract
:1. Introduction
2. Experimental Section
2.1. Precipitation of Asphaltenes
2.2. Analytical Methods
2.2.1. Elemental Analysis
2.2.2. Relative Molecular Mass Analysis
2.2.3. ESI FT-ICR MS
2.3. Data Analysis Procedure
3. Results and Discussions
3.1. Negative Ion ESI FT-ICR Mass Spectra
3.2. Heteroatom-Containing Compounds Distribution
3.3. The Molecular Structure of Heteroato-Containing Compounds
3.3.1. OX(x = 2–4) Class Species in M/LTCT Asphaltenes
O2 Class Species
O3 Class Species
O4 Class Species
3.3.2. Distribution of NX Class Species
3.3.3. Distribution of Muti-Heteroatom Class Species
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Properties | M/LTCT | M/LTCT Asphaltenes | |
---|---|---|---|
Elemental analysis/% | C | 81.46 | 81.72 |
H | 8.61 | 5.68 | |
N | 1.26 | 2.33 | |
S | 0.34 | 1.86 | |
O | 8.03 | 8.92 | |
H/C atomic ratio | 1.268 | 0.818 | |
Density (20 °C)/g·cm−3 | 1.041 | - | |
Mw | 420 | 663 |
NO | Formula [M + H]− | Theoretical Mass (Da) | Measured Mass (Da) | Error (m/z) | Resolving Power |
---|---|---|---|---|---|
332.1465 | 332.1363 | 0.0102 | 132,193 | ||
332.3495 | 332.2229 | 0.1266 | 126,027 | ||
332.4932 | 332.4841 | 0.0091 | 121,912 | ||
332.6737 | 332.6715 | 0.0022 | 134,457 |
Feed | Most Abundant Oxygen Species | DBE Center | Carbon Numbers Center | Possible Core Structure | |
---|---|---|---|---|---|
The present work | M/LTCT asphaltenes | O4 | 4–15 | 12–27 | Quaternary phenolic hydroxyl |
Wang et al. [33] | Oil sands bitumen asphaltenes | O2 | 3–5 | 28–35 | Naphthenic acid |
Xu et al. [31] | Sudan sand oil asphaltenes | O2 | 0–8 | 25–35 | Naphthenic acid |
Shi et al. [32] | Crude Oil asphaltenes | O1 | 4–6 | 27–40 | Phenolic hydroxyl |
Feed | Most Abundant Nitrogen Species | DBE Center | C Center | Possible Core Structure | |
---|---|---|---|---|---|
The present work | M/LTCT asphaltenes | N4 | 16–25 | 12–23 | A piperazine ring with a pyrazole ring |
Wang et al. [33] | Oil sands bitumen asphaltenes | N1 | 14–24 | 22–37 | Pyrrole ring |
Xu et al. [31] | Sudan asphaltenes | N1 | 10–16 | 22–35 | Carbazole ring |
Shi et al. [32] | Crude Oil asphaltenes | N1 | 9–19 | 21–37 | Carbazole ring |
Wang et al. [21] | Petroleum asphaltenes | N1 | 9–20 | 20–46 | Carbazole ring |
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Fan, X.; Li, D.; Cui, L.; Shao, R.; Chang, C.; Yan, L.; Yang, B. Analysis of Distribution and Structures of Heteroatom Compounds in Asphaltene of Medium/Low Temperature Coal Tar by Negative Anion Mode ESI FT-ICR MS. Sustainability 2022, 14, 15497. https://doi.org/10.3390/su142315497
Fan X, Li D, Cui L, Shao R, Chang C, Yan L, Yang B. Analysis of Distribution and Structures of Heteroatom Compounds in Asphaltene of Medium/Low Temperature Coal Tar by Negative Anion Mode ESI FT-ICR MS. Sustainability. 2022; 14(23):15497. https://doi.org/10.3390/su142315497
Chicago/Turabian StyleFan, Xiaoyong, Dong Li, Louwei Cui, Ruitian Shao, Chunran Chang, Long Yan, and Bo Yang. 2022. "Analysis of Distribution and Structures of Heteroatom Compounds in Asphaltene of Medium/Low Temperature Coal Tar by Negative Anion Mode ESI FT-ICR MS" Sustainability 14, no. 23: 15497. https://doi.org/10.3390/su142315497