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Analysis and identification of oxygen compounds in Longkou Shale Oil and Shenmu coal tar.

1. Introduction

In the time of high crude oil prices, oil shale mining and retorting for producing shale oil have become profitable in some countries. Especially in China, but also elsewhere in the world, the production of domestic crude oil is unable to meet the ever-growing demand for this resource, and a substantial amount of crude oil is imported [1-3].

Shale oil (SO) is produced from the organic matter contained in oil shale by pyrolysis [1], while low-temperature coal tar (LTCT) is a by-product of the low-temperature carbonization of coal. SO and LTCT contain compounds, such as [alpha]-and [beta]-methylnaphthalenes, biphenyl, phenol, indole, fluorine, etc., which are valuable chemical raw materials for various applications. It is unreasonable to take SO and LTCT just for fuels. The oxygen compounds of shale oil and coal tar can be used to produce plastics, fibers, dyes, rubbers, pesticides, pharmaceuticals, high temperature resistant materials, etc. Therefore, analysis of the oxygen compounds contained in SO and LTCT is useful from the viewpoint of a comprehensive utilization of these products [4].

Shale oil and low-temperature coal tar are complex compounds, both being rich in alkanes, cyclanes, arenes, as well as nitrogen-, sulfur-, and oxygen-containing non-hydrocarbons, Hence, it is hard to analyze oxygen compounds in question without pretreatment of oils. Earlier traditional methods such as column chromatography and also distillation were used for the component analysis of oils [5, 6]. With the development of chromatographic separation methods, the molecular constitutions of shale oil and coal tar were gradually established. Zhu et al. [7] separated two kinds of shale oils from mountainous area (land) and coastal shelf rock (sea), both China, into four fractions using silica gel column chromatography. The components of each fraction were identified by GC-MS. The results show that shale oil from land contains 269 compounds, with abundant hydrocarbon compounds (79%), and some sulfur, oxygen and nitrogen compounds. Shale oil from sea rocks contains 284 compounds with a high amount of hydrocarbon and oxygen compounds (60 and 29%, respectively), and some sulfur and nitrogen compounds. Guo et al. [8] analyzed by GC-MS shale oils from Fushun oil shale of Liaoning province and Maoming oil shale of Guangdong province, both China. The main oxygen-containing compounds identified are phenols, diphenols, 2-, 3- and 4-alkanones, furans and benzofurans. Among the oxygen compounds, phenols constitute 7-8 wt% of oil (<350 [degrees]C), the next most abundant being ketones. Zhou et al. [9] analyzed phenolic compounds in LTCT, using the reversed-phase high-performance liquid chromatography (HPLC). Of phenolic compounds, eight were determined, including phenols, cresols, xylenols, trimethylphenols and naphthols. The low-temperature tar obtained at 550 [degrees]C by means of the GrayKing test was examined by Maria et al. [10] using GC-MS. The tar is made up mainly of mono- and di-aromatic compounds with a preponderance of phenolics. William et al. [11] identified [C.sub.0]-[C.sub.6] methyl phenols and [C.sub.0]-[C.sub.3] indanol phenols in the coal-derived liquids by GC-MS.

Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) has become a promising tool for analyzing the composition of complex mixtures. This technique offers the highest available broadband mass resolution,mass resolving power and mass accuracy, which allows the assignment of a unique elemental composition to each peak in a mass spectrum. The high selectivity of electrospray ionization (ESI) improves identification of trace polar compounds found in petroleum systems [12]. By ESI coupled to high-field (9.4 T) FT-ICR MS tens of thousands of compounds observed as positive or negative molecular ions from basic or acidic species, respectively, have been resolved and their elemental compositions (CcHhNnOoSs) as well as the degree of saturation (number of rings plus double bonds) in crude oil, shale oil and coal tar and their distillates determined [12-14]. Bae et al. [15] compared the molecular compositions of two shale oils of oil shales from U. S. Western and Russian mines, using 15T FT-ICR MS coupled with ESI, and atmospheric pressure photoionization (APPI). The class and double-bond equivalence (DBE) distributions of shale oils were compared with those of conventional oil. Wu et al. [14, 16, 17] resolved and identified several thousand polar compounds in coal extracts of two geochemical origins, and examined their class, type and alkylation distributions by negative-ion ESI FT-ICR MS.

In this paper, a comprehensive compositional analysis of the oxygencontaining compounds present in LSO and SLTCT was performed using FT-ICR MS and GC-MS. This effort lays the groundwork for a better understanding of the heteroatom-containing species present in shale oil and coal tar.

2. Experimental

2.1. Materials

Shale oil was obtained from Longkou oil shale (Shandong province, China) by pyrolysis at 600 [degrees]C. Low-temperature coal tar was obtained from the Sanjiang Coal Chemical Company, Shenmu, Shanxi province, China. The properties of LSO and SLTCT are presented in Table 1.

2.2. Separation methods for GC-MS analysis

Methods of acid-base separation [18] and extrography [19] were used to decompose LSO and SLTCT into acid, base and five neutral fractions. Neutral fractions 1, 2 and 3 (Table 3) in the oils were mainly saturates, aromatics and nitrogen-containing compounds, respectively. The oxygen-containing compounds analyzed in this article are acid fractions and neutral fractions 4 and 5.

As seen from Table 2, the acid fraction content in LSO is much higher than in SLTCT, which is consistent with the oxygen content of the oils (Table 1).

It is clear from Table 3 that the content of neutral component 5 in LSO is lower than in SLTCT, while the contents of neutral component 4 in the oils are almost similar.

2.3. GC-MS analysis

A Thermo-Finnigan Trace DSQ GC-MS coupled with an HP-5MS (30 m x 0.25 mm x 0.25 um) fused silica capillary column was used to analyze the composition of shale oil and coal tar samples. The mass spectrometer was operated with an electron impact (EI) source at a 70 eV ionization energy. The mass range was set to 35-500 Da at 1-s scanning intervals. The oven temperature was maintained at 50 [degrees]C for 1 min, then increased to 300 [degrees]C at 4 [degrees]C/min and held constant at 300 [degrees]C for 30 min. The sample was injected at 300 [degrees]C. The amount of the injected sample was 1 [micro]L at a Concentration of 8 mg/mL. Helium was used as a carrier gas at a flow rate of 1 mL/min.

2.4. FT-ICR MS analysis

The samples of shale oil and coal tar to be analyzed by ESI FT-ICR MS were dissolved with a 3:1 solvent mixture of toluene and dichloromethane to 10 mg/mL. A total of 20 mL of the sample solution was further diluted with 1 mL of a 1:1 toluene/methanol solution. The resulting sample solutions were subjected to ESI FT-ICR MS analysis without further treatment. All the solvents used were analytical reagent grade and were distilled twice. Glassware was used for solvent handling and transfer, except for the steel pistons of 10 [micro]L Hamilton syringes. The samples were analyzed using a Bruker Apex ultra FT-ICR MS equipped with a 9.4 T superconducting magnet. The sample solutions were infused at a flow rate of 180 [micro]L/h. Typical conditions for negative ion formation were the following: emitter voltage 4.0 kV, the voltage introduced to the capillary column 4.5 kV, capillary column end voltage -320 V. The ions were accumulated for 0.1 s in an argon-filled collision cell and transferred to the ICR cell with a 1.2 ms time-of-flight window. The ions were trapped with a sidekick voltage of 6 V. At least 200 scans were accumulated and averaged to improve the signal-to-noise ratio of the obtained spectra. The mass range was set at 100-800 m/z. The size of the data set was adjusted to 2 M words.

3. Results and discussion

3.1. ESI FT-ICR MS analysis of shale oil and coal tar

Figure 1 illustrates negative-ion ESI FT-ICR MS spectrums of LSO and SLTCT. It is clearly seen that the molecular weight range of LSO is wider than that of SLTCT. The peaks with masses of LSO are within the molecular weight range of 150-600 Da, while the m/z values of SLTCT are from 100 to 350. Being lower than 600, these m/z values indicate that LSO and SLTCT are composed mainly of low molecular compounds, and the latter are polymerized by the van der Waals force and hydrogen bonding. So, the properties of shale oil and coal tar, such as fluidity and viscosity, are similar to those of macromolecular compounds.

Figure 2 depicts the heteroatom class and type distribution of LSO and SLTCT derived from a negative-ion ESI FT-ICR MS spectrum. The relative abundance of the peaks of [O.sub.1], [O.sub.2], [O.sub.3], [N.sub.1] [O.sub.1], [N.sub.1] [O.sub.2], [N.sub.1] and [N.sub.2] compounds in shale oil is 36.25, 35.35, 3.05, 4.38, 7.47, 6.37 and 7.12, respectively. The oxygen compounds O1 and O2 are prevailing in LSO, while in SLTCT, [O.sub.2] and [O.sub.3] compounds are dominant species with the respective abundances of 58.98 and 24.05%. In SLTCT, the other oxygen compounds are less abundant: [O.sub.1] 1.79%, [O.sub.4] 8.24%, [O.sub.5] 5.58% and [O.sub.6] 1.35%. [N.sub.1] [O.sub.1] and [N.sub.1] [O.sub.2] compounds were determined in shale oil only, while [O.sub.4], [O.sub.5] and [O.sub.6] compounds were detected only in coal tar.

[FIGURE 1 OMITTED]

[FIGURE 2 OMITTED]

The number of rings plus double bonds is usually expressed by a double bond equivalent value (DBE) [20]. DBE indicates hydrogen deficiency of a given molecular formula and is commonly used to investigate the highresolution mass spectra of crude oil [15]. The DBE values of the compounds identified in LSO are chiefly 1 and 4. The DBE values of [O.sub.1] compounds are mostly 4 and 5, indicating that of these compounds, phenols and indanols are present in LSO. DBE of [O.sub.2] compounds is mainly 1, suggesting that of the latter compounds, acids or lipids occur in LSO. Abundant [O.sub.3] compounds have DBE of 1 or 14, while those values of [N.sub.1] [O.sub.1], [N.sub.1] [O.sub.2], [N.sub.1] and [N.sub.2] compounds are similar. The DBE values of the compounds identified in SLTCT are mainly 4 and 9, being a little different from those of LSO's. DBE of [O.sub.1] compounds is mostly 7. Of oxygen compounds, chiefly phenols occur in coal tar, implying that naphthols may exist as O1 compounds. The occurrence of [O.sub.2] compounds with DBE of 4 and 9 suggests that mostly diphenols are present in SLTCT. [O.sub.3] compounds with DBE of 9 are abundant in shale oil, while [O.sub.4], [O.sub.5] and [O.sub.6] compounds with DBE of 10 predominate in SLTCT.

Figure 3 compares plots of DBE versus the carbon number of heteroatom compounds in LSO and SLTCT. In LSO, [O.sub.1] compounds have DBE of 4-16 and carbon number of 12-41, the most abundant being those with DBE of 4 and carbon number of 28. When DBE is 4, 7 or 9, among these compounds, probably phenols, naphthols and fluorenols, respectively, predominate. The [O.sub.1] compounds contained in SLTCT have DBE of 4-9 and carbon number of 10-22. DBE of the most abundant [O.sub.1] compounds in SLTCT is 7 and carbon number 11. So, the range of DBE values and carbon numbers for [O.sub.1] compounds in LSO is wider than that in SLTCT. The [O.sub.2] compounds present in LSO have DBE of 1-16 and carbon number of 14-33, while the respective values in SLTCT are 4-12 and 8-21. Thus, the range of DBE values and carbon numbers for [O.sub.2] compounds in LSO is also wider than that in SLTCT. The most abundant [O.sub.2] compounds in LSO are those whose DBE is 1 and carbon number 28. In SLTCT, [O.sub.2] compounds with DBE of 4 and 9 and carbon number of 14 and 15 are prevailing. In LSO, [O.sub.2] compounds with DBE of 1 may be acids or lipids, whereas no [O.sub.2] compounds with this DBE value have been found in Shenmu low-temperature coal tar. When DBE is 4, 5 or 7, the compounds are dihydroxybenzenes, bisphenol indanes and naphthalenediols, respectively. [O.sub.3] compounds with DBE of 1 and 14 are abundant in LSO, in contrast to SLTCT, in which [O.sub.3] compounds with DBE of 9 are predominant. Overall, the ranges of both DBE values and carbon numbers of oxygen compounds in LSO are wider than those in SLTCT, indicating that oxygen compounds in LSO may have longer side chains on the core of the molecules than those in SLTCT [21]. The presence of [O.sub.1], [O.sub.2] and [O.sub.3] compounds, whose DBE is mostly 1 or 4, suggests that LSO is less biodegraded [15, 22, 23].

[FIGURE 3 OMITTED]

3.2. GC-MS analysis of the acid fractions of shale oil and coal tar

Figure 4 shows the TIC of the acid fraction from LSO and SLTCT. It is obvious that both are complex mixtures, with a wide range of components present.

Based on the results of GC-MS analysis, monohydric phenols, such as phenols, indanols, naphthols, phenylphenols, fluorenols and phenanthrenols, were identified in the two oils. From Figures 2 and 3 it is seen that [O.sub.1] compounds with DBE of 4, 5, 7, 9 or 11 were phenols, indanols, naphthols, fluorenols and phenanthrenols, respectively. I n LSO, carboxylic acids ranged from [C.sub.5] to [C.sub.16], whereas no these acids were found in SLTCT. [O.sub.2] compounds are usually considered as carboxylic acids in petroleum and coal liquefaction products [14, 16, 17]. However, dihydroxybenzenes have also been identified among the acid components of SLTCT. Shi et al. stated that dihydroxy aromatics were dominant [O.sub.2] compounds in the coal tar distillate fraction [24].

[FIGURE 4 OMITTED]

[FIGURE 5 OMITTED]

In LSO, the content of the acid components detected accounts for 83.51%. Among them, phenol and phenol derivatives constitute 66.63%, indanol and its derivatives 7.53%, naphthol and its derivatives 8.42%, while carboxylic acids account for only 0.2%. The relative content of the acid components detected in SLTCT makes 51.20%. Of them, phenol and phenol derivatives account for 33.43%, indanol and its derivatives 5.71%, naphthol and its derivatives 8.13%, while phenanthrenol and its derivatives constitute about 1.14%. The relative content of phenol and phenol derivatives is high, which is consistent with the fact that DBE of the compounds identified in LSO and SLTCT is mainly 4.

3.3. GC-MS analysis of neutral fractions 4 and 5 of shale oil and coal tar

Neutral fraction 4 of LSO involves aliphatic ketones ranging from [C.sub.9] to [C.sub.32], their relative content being 22.17%, while neutral fraction 4 of SLTCT is mostly represented by aliphatic ketones ranging from [C.sub.10] to [C.sub.28,] with a relative content of 4.88%. Compared with SLTCT, the range of carbon numbers of the aliphatic ketones present in LSO is wider.

Neutral fraction 5 of LSO includes chiefly esters with a relative content of 5.35%. SLTCT involves aliphatic ketones ranging from [C.sub.10] to [C.sub.29], and minor aromatic ketones, the relative content of neutral fraction 5 being 16.64%.

4. Conclusions

In this paper, a comprehensive compositional analysis and comparison of the oxygen compounds present in Longkou shale oil (LSO) and Shenmu lowtemperature coal tar (SLTCT) were performed using FT-ICR MS and GCMS. The following conclusions were drawn:

1. The weight-average molecular weights of LSO and SLTCT are low. It is obviously because LSO and SLTCT are composed mainly of low molecular compounds and the latter are polymerized by the van der Waals force and hydrogen bonding. So, the properties of shale oil and coal tar, such as fluidity and viscosity, are similar to those of macromolecular compounds.

2. In LSO, [O.sub.1], [O.sub.2], [O.sub.3], [N.sub.1][O.sub.1], [N.sub.1][O.sub.2], [N.sub.1] And [N.sub.2] compounds are present with [O.sub.1] and [O.sub.2] compounds as the most abundant. SLTCT includes [O.sub.1], [O.sub.2,] [O.sub.3], [O.sub.4], [O.sub.5] and [O.sub.6] compounds, while [O.sub.2] and [O.sub.3] compounds are dominating.

3. The ranges of both the DBE values and carbon numbers of oxygen compounds of LSO are wider than those of SLTCT, indicating that oxygen compounds in LSO have longer side chains on the core of the molecules than those in SLTCT.

4. LSO contains [O.sub.1], [O.sub.2] and [O.sub.3] compounds whose DBE is mainly 1 and 4, implying that this oil is less biodegraded.

5. The oxygen compounds in the acid fractions of LSO and SLTCT are represented by phenols, indanols, naphthols, phenylphenols, fluorenols and phenanthrenols, and their derivatives. The relative content of phenol and phenol derivatives is high, which is consistent with the fact that DBE of the compounds identified in LSO and SLTCT is chiefly 4.

6. Neutral fraction 4 of LSO involves aliphatic ketones ranging from [C.sub.9] to [C.sub.32,] their relative content being 22.17%, while that of SLTCT includes mainly aliphatic ketones ranging from [C.sub.10] to [C.sub.28,] with a relative content of 4.88%. Compared with SLTCT, the carbon number range of aliphatic ketones in LSO is wider.

7. Neutral fraction 5 of LSO contains mainly esters, with a relative content of 5.35%. Neutral fraction 5 of SLTCT involves aliphatic ketones ranging from [C.sub.10] to [C.sub.29,] and minor aromatic ketones, whose relative content is 16.64%.

doi: 10.3176/oil.2012.4.03

Acknowledgements

This work was supported by the Taishan Scholar Constructive Engineering Foundation of Shandong province, China (No.ts20120518), and the Science Foundation of China University of Petroleum, Beijing, China (No. KYJJ2012-06-32).

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Received May 25, 2012

CENGCENG GENG (a), SHUYUAN LI (a) * YUE MA (a), CHANGTAO YUE (a), JILAI HE (b), WENZHI SHANG (c)

(a) State Key Laboratory of Heavy Oil Processing, China University of Petroleum, Beijing 102249, China

(b) Shandong Energy Longkou Mining Group Co., Ltd, Longkou 265700, China

(c) Shenmu Sanjiang Coal Chemical Liability Co., Ltd, Yulin 719300, China

* Corresponding author: email syli@cup.edu.cn; 753099003@qq.com
Table 1. Properties of LSO and SLTCT

Sample Oxygen, Viscosity Ash, Carbon
 m% (50 % residue,
 [DEGREES]C) %
 [mm.sup.2]
 /[s.sup.-1]

LSO 3.68 19.01 0.58 3.42
SLTCT 6.07 16.83 0.085 6.89

Sample Freezing Moisture, Density Flash
 point, % (20, point,
 [degrees]C [degrees] [degrees]C
 g/[mL.
 sup-1]

LSO 32 1.26 0.9047 132
SLTCT 27 2.89 1.02 125

Table 2. Acid-base extraction of LSO and SLTCT

Sample Acid Basic Neutral Recovery,
 component, component, component, m%
 m% m% m%

LSO 8.02 3.58 83.54 95.14
SLTCT 37.60 3.04 53.72 94.36

Table 3. Chromatographic separation of neutral fractions

Sample Neutral Neutral Neutral
 component 1, component 2, component 3,
 m% m% m%

LSO 44.72 24.35 1.15
SLTCT 22.12 35.15 2.54

Sample Neutral Neutral Recovery,
 component 4, component 5 m%
 m% m%

LSO 18.60 0.20 89.02
SLTCT 18.00 10.84 88.65
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Author:Geng, Cengceng; Li, Shuyuan; Ma, Yue; Yue, Changtao; He, Jilai; Shang, Wenzhi
Publication:Oil Shale
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Date:Dec 1, 2012
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