基于GC×GC-TOF MS的煤液化产物油分子组成结构表征

doi:10.11949/0438-1157.20241047

化工学报 ›› 2025, Vol. 76 ›› Issue (2): 543-553.DOI: 10.11949/0438-1157.20241047

• 热力学 • 上一篇

基于GC×GC-TOF MS的煤液化产物油分子组成结构表征

李奕菲¹(), 苏沿霏¹, 尹甜², 姜浩强³, 许志明¹, 张霖宙¹(), 史权¹(), 徐春明¹

^1.中国石油大学（北京）重质油全国重点实验室石油分子工程中心，北京 102249
^2.中国神华煤制油化工有限公司，北京 100010
^3.中国神华煤制油化工有限公司鄂尔多斯煤制油分公司，内蒙古鄂尔多斯 017209

收稿日期:2024-09-19 修回日期:2024-10-16 出版日期:2025-03-25 发布日期:2025-03-10
通讯作者: 张霖宙,史权
作者简介:李奕菲（1995—），女，博士研究生，Liyifei_CUP@126.com
基金资助:
国家自然科学基金项目(22222815);国家能源集团科技项目(GJNY-23-23)

Molecular composition and structure characterization of coal liquefaction product oil based on GC×GC-TOF MS

Yifei LI¹(), Yanfei SU¹, Tian YIN², Haoqiang JIANG³, Zhiming XU¹, Linzhou ZHANG¹(), Quan SHI¹(), Chunming XU¹

^1.State Key Laboratory of Heavy Oil Processing, Petroleum Molecular Engineering Center (PMEC), China University of Petroleum, Beijing 102249, China
^2.China Shenhua Coal to Liquid and Chemical Co. , Ltd. , Beijing 100010, China
^3.Ordos Coal to Oil Branch, China Shenhua Coal to Liquid and Chemical Co. , Ltd. , Ordos 017209, Inner Mongolia, China

Received:2024-09-19 Revised:2024-10-16 Online:2025-03-25 Published:2025-03-10
Contact: Linzhou ZHANG, Quan SHI

摘要/Abstract

摘要：

煤直接液化产物分子组成复杂，探究产物的详细分子组成对煤制油工艺的优化具有重要意义。建立了煤液化油及其加氢过程产物的全二维气相色谱-飞行时间质谱/氢火焰离子化检测器（GC×GC-TOF MS/FID）分子层次的组成和结构定性定量表征方法，揭示了煤液化加氢反应规律。GC×GC-TOF MS液化油分子组成表征技术通过分子极性在二维上的差异初步解决了一维色谱中多个化合物因保留时间相近共逸出的问题。煤液化油加氢后环烷烃含量增加，芳烃含量减少。在循环溶剂中主要通过三环、四环芳烃分子不同程度的氢化分子起到溶氢供氢的作用。另外，针对煤直接液化石脑油和柴油也建立了GC×GC-TOF MS/FID烃族组成表征，与直馏加氢汽柴油的族组成含量相比，煤直接液化产物中含有较多的环烷烃化合物。

关键词: 煤制油, 加氢, 化学分析, GC×GC-TOF MS, 分子工程, 定性定量

Abstract:

The molecular composition of the direct coal liquefaction products is complex. It is of great significance to explore the detailed molecular composition of the direct coal liquefaction products for the optimization of the coal-to-oil process. Comprehensive two-dimensional gas chromatography coupled with time-of-flight mass spectrometry/hydrogen flame ionization detector (GC×GC-TOF MS/FID) method was established for the qualitative and quantitative characterization of composition and structure of coal liquefaction oil and its hydrogenation process products at the molecular level,which revealed the hydrogenation reaction law of coal liquefaction. The molecular composition characterization technology of GC×GC-TOF MS liquefied oil preliminarily solved the problem that multiple compounds co-escape in one-dimensional chromatography due to the same retention time through the difference of molecular polarity in two dimensions. After hydrogenation of coal liquefaction oil, the content of cycloalkanes increases and the content of aromatics decreases. In the circulating solvent, the hydrogen dissolving and supplying hydrogen is mainly achieved through the hydrogenation of three-ring and four-ring aromatic molecules to varying degrees. In addition, the GC×GC-TOF MS/FID characterization technology of hydrocarbon group composition was also established for direct coal liquefaction naphtha and diesel. Compared with the group composition content of straight-run hydrogenated diesel and gasoline, the direct coal liquefaction products diesel and gasoline contain more monocyclic, bicyclic and tricyclic alkanes.

Key words: coal to oil, hydrogenation, chemical analysis, GC×GC-TOF MS, molecular engineering, qualitative and quantitative

中图分类号:

TE 622

李奕菲, 苏沿霏, 尹甜, 姜浩强, 许志明, 张霖宙, 史权, 徐春明. 基于GC×GC-TOF MS的煤液化产物油分子组成结构表征[J]. 化工学报, 2025, 76(2): 543-553.

Yifei LI, Yanfei SU, Tian YIN, Haoqiang JIANG, Zhiming XU, Linzhou ZHANG, Quan SHI, Chunming XU. Molecular composition and structure characterization of coal liquefaction product oil based on GC×GC-TOF MS[J]. CIESC Journal, 2025, 76(2): 543-553.

图/表 9

表1 GC×GC实验条件

Table 1 GC×GC experimental conditions

项目	GC×GC实验条件
色谱柱1	HP-PONA 50 m×0.2 mm×0.5 µm
色谱柱2	BPX-50 2.5 m×0.1 mm×0.1 µm
柱流量	恒流0.6 ml/min
进样量和分流比	0.05 µl，100∶1
柱箱	40℃（5 min）-1.5℃/min-150/280/310℃（10 min）
进样口温度	250℃/300℃
调制器周期	石脑油6 s，柴油8 s，改质料16 s，液化油和供氢溶剂18 s

图1 煤直接液化工艺物料流程示意图[33]1—煤浆罐;2—加热炉;3,4—悬浮床反应器;5—分离器;6—常压蒸馏塔;7—减压蒸馏塔;8—沸腾床反应器;9—分离塔;10—固定床反应器;11—分离塔

Fig.1 Material flow diagram of coal direct liquefaction process[33]

图2 煤液化油及其四种产品的高温模拟蒸馏谱图

Fig.2 High temperature simulated distillation spectra of coal liquefaction oil and its four products

图3 煤液化油(a) GC-MS和(b) GC×GC-TOF MS总离子流图，(c) GC×GC-TOF MS局部放大图

Fig.3 Coal liquefaction oil (a) GC-MS and (b) GC×GC-TOF MS total ion chromatogram, (c) GC×GC-TOF MS partial enlarged chromatogram

图4 (a)供氢溶剂和(b)改质料GC×GC-TOF MS总离子流图和三维立体图

Fig.4 (a) Hydrogen-donating solvent and (b) GC×GC-TOF MS total ion current diagram and three-dimensional map

图5 (a)煤液化油和(b)供氢溶剂芘同系数及其加氢化合物GC×GC-TOF MS谱图，(c) GC×GC-FID含量柱状图

Fig.5 GC×GC-TOF MS spectra of (a) coal liquefaction oil and (b) hydrogen donor solvent pyrene and its hydrogenated compounds, (c) GC×GC-FID content histogram

图6 (a)煤直接液化柴油和(b)直馏加氢柴油GC×GC-TOF MS谱图，(c) GC×GC-FID含量柱状图

Fig.6 GC×GC-TOF MS spectra of (a) direct coal liquefaction diesel and (b) straight-run hydrogenated diesel, (c) GC × GC-FID content histogram

图7 (a)煤直接液化石脑油和(b)直馏加氢汽油GC×GC-TOF MS谱图，(c) GC×GC-FID含量柱状图

Fig.7 GC×GC-TOF MS spectra of (a) direct coal liquefaction gasoline and (b) straight-run hydrogenated gasoline, (c) GC × GC-FID content histogram

表A1 煤液化油代表性分子信息

Table A1 Representative molecular information of coal liquefaction oil

编号	名称	分子式	分子量	1D (min) / 2D (s)	含量
1	正十五烷	C₁₅H₃₂	212.3	105.2/2.2	27.1
2	甲基环己烷	C₇H₁₄	98.1	26.6/2.2	16.6
3	十氢化萘	C₁₀H₁₈	138.1	64.1/2.8	7.8
4	十二氢非那烯	C₁₃H₂₂	178.2	93.8/3.5	14.0
5	16H-芘	C₁₆H₂₆	218.2	119.9/4.4	112.6
6	乙苯	C₈H₁₀	106.1	41.6/3.5	6.1
7	1-甲基茚满	C₁₀H₁₂	132.1	65.9/4.0	11.3
8	1,2,2a,3,4,5-六氢苊烯	C₁₂H₁₄	158.1	94.1/5.3	20.0
9	萘	C₁₀H₈	128.1	75.5/5.9	20.6
10	3-(1,1-二甲基乙基)-1,2-二氢萘	C₁₄H₁₈	186.1	112.1/5.6	70.7
11	4,4^′-二甲基联苯	C₁₀H₁₈	182.1	120.2/7.3	39.4
12	芴	C₁₃H₁₀	166.1	110.9/7.3	23.4
13	9,10-二氢蒽	C₁₄H₁₂	180.1	119.0/7.9	9.4
14	1,2,3,4-四氢蒽	C₁₄H₁₄	182.1	123.2/7.9	18.7
15	2-甲基蒽	C₁₅H₁₂	192.1	133.1/9.1	24.8
16	芘	C₁₆H₁₀	202.1	147.2/11.7	276.5
17	4,5-二氢芘	C₁₆H₁₂	204.1	143.3/11.0	30.5
18	4,5,9,10-四氢芘	C₁₆H₁₄	206.1	137.3/9.8	5.9
19	1,2,3,6,7,8-六氢芘	C₁₆H₁₆	208.1	141.5/9.9	13.5
20	4-甲基䓛	C₁₉H₁₄	242.1	173.9/14.9	13.1
21	苯酚	C₆H₆O	94.0	52.4/5.6	5.4
22	5-茚醇	C₉H₁₀O	134.1	89.0/6.8	2.6

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基于GC×GC-TOF MS的煤液化产物油分子组成结构表征

Molecular composition and structure characterization of coal liquefaction product oil based on GC×GC-TOF MS

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