中低温煤焦油重油正庚烷萃余物的反应(甲醛)分离与分析

冯新娟; 闵小建; 郑化安; 樊英杰; 李亚波; 孔祥玺; 万冲; 孙鸣; 马晓迅

中低温煤焦油重油正庚烷萃余物的反应(甲醛)分离与分析

1.
西北大学化工学院碳氢资源清洁利用国家国际科技合作基地, 陕北能源先进化工利用技术教育部工程研究中心, 陕西省洁净煤转化工程技术中心, 陕北能源化工产业发展协同创新中心, 陕西西安 710069
2.
陕西煤业化工技术研究院有限责任公司, 陕西西安 710070

基金项目:

国家自然科学基金 21536009

国家自然科学基金 21406178

陕西省重点研发计划项目 2017ZDCXL-GY-10-03

陕西省青年科技新星支持计划 2017KJXX-62

陕西省自然科学基础研究计划项目 2017JQ2040

西北大学"优秀青年学术骨干支持计划" 2015

详细信息

中图分类号: TQ523
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出版历程
- 收稿日期: 2017-08-22
- 修回日期: 2017-11-01
- 网络出版日期: 2021-01-23
- 刊出日期: 2018-01-10

Reaction (formaldehyde) separation and analysis of n-heptane extraction residue from heavy oil of medium and low temperature coal tar

1.
School of Chemical Engineering, Northwest University, International Scientific and Technological Cooperation Base for Clean Utilization of Hydrocarbon Resources, Chemical Engineering Research Center of the Ministry of Education for Advance Use Technology Energy of Northern Shaanxi, Shaanxi Research Center of Engineering Technology for Clean Coal Conversion, Collaborative Innovation Center for Development of Energy and Chemical Industry in Northern Shaanxi, Xi'an 710069, China
2.
Shaanxi Coal Chemical Industry Technology Research Institute Co., Ltd., Xi'an 710070, China

Funds:

the National Natural Science Foundation of China 21536009

the National Natural Science Foundation of China 21406178

Science and Technology Plan Projects of Shanxi Province 2017ZDCXL-GY-10-03

the Young Science and Technology Star Project of Shaanxi Province 2017KJXX-62

Project Academic Supported by Natural Science Basic Research Plan in Shaanxi Province of China 2017JQ2040

Foundation of Outstanding Young Backbone Supporting Program of Northwest University 2015

More Information

Corresponding author: SUN Ming, E-mail: sunming@nwu.edu.cn; MA Xiao-xun, E-mail: maxym@nwu.edu.cn

摘要

摘要: 以陕北中低温煤焦油重油为原料，采用正庚烷溶剂萃取得到煤焦油正庚烷萃余物（H-CT）并与甲醛反应，通过溶剂萃取法将反应后产物（P）分为：正庚烷可溶物（HS-P）、正庚烷不溶甲苯可溶物（HI-TS-P）、甲苯不溶喹啉可溶物（TI-QS-P）和喹啉不溶物（QI-P）。借助GC-MS、FT-IR、TG-FTIR等分析手段，对P的结构组成进行了表征。结果表明，与H-CT相比，P中TI-QS-P组分和氧原子的含量较多，C/H原子比较高；HS-P、HI-TS-P、TI-QS-P和QI-P的含量分别为11.63%、26.42%、57.08%和4.88%；HS-P和HI-TS-P均以中性组分（以芳烃为主）为主，酸性组分（以酚类为主）含量较少，其余为含O、N、S等杂原子化合物；TI-QS-P富集了羰基、亚甲基桥键及稠环芳香化合物，且含酚羟基及芳环取代物，具有较高的热稳定性。
- 中低温煤焦油 /
- 酚醛反应 /
- 聚合 /
- 萃取 /
- 分离与分析
Abstract: The n-heptane extraction residue (H-CT) from heavy medium and low temperature coal tar made in northern Shaanxi by n-heptane was reacted with formaldehyde. The product (P) was divided into n-heptane soluble (HS-P), n-heptane insoluble but toluene soluble (HI-TS-P), toluene insoluble but quinoline soluble (TI-QS-P) and quinoline insoluble (QI-P). The structure and composition of P were analyzed by means of GC-MS, TG-FTIR and FT-IR. The results show that P has more contents of TI-QS-P, oxygen atoms and a higher C/H atom ratio comparing with H-CT. The contents of HS-P, HI-TS-P, TI-QS-P and QI-P are 11.63%, 26.42%, 57.08% and 4.88%, respectively. HS-P and HI-TS-P contain mainly neutral components (mainly aromatics), few acidic components (mainly phenols), and some heteroatom compounds including O, N, S. TI-QS-P, with highly thermal stability, is rich in carbonyl groups, methylene bridge bonds and fused ring aromatic compounds. Besides, it also contains phenolic hydroxyl groups and aromatic ring substitutes.
- medium and low temperature coal tar /
- phenol-formaldehyde reaction /
- polymerization /
- extraction /
- separation and analysis

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图 1 H-CT反应分离与分析路线示意图

Figure 1 Reaction separation and analysis routes of H-CT

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图 2 样品的总离子流色谱图

Figure 2 GC-MS total ion chromatogram of samples

(a): TS-H-CT; (b): HS-P; (c): HI-TS-P

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图 3 TS-H-CT、HI-TS-P及HS-P中各类化合物的含量

Figure 3 Content of various components in TS-H-CT, HI-TS-P and HS-P

1: neutral components; 2: acid components; 3: xygenous compounds; 4: nitrogenous compounds; 5: sulfur compounds

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图 4 H-CT、P及TI-QS组分的TG和DTG曲线

Figure 4 TG and DTG curves of H-CT(a), P(b), TI-QS-H-CT (c) and TI-QS-P(d)

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图 5 TI-QS-P热解挥发分的红外光谱3D

Figure 5 3D FT-IR spectra of the pyrolysis volatile of TI-QS-P

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图 6 样品的热解过程中挥发分的FT-IR谱图

Figure 6 FT-IR spectra of volatiles during pyrolysis of samples

(a): H-CT; (b): P; (c): TI-QS-H-CT; (d): TI-QS-P

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图 7 H-CT、P及各组分的FT-IR谱图

Figure 7 FT-IR spectra of H-CT, P and each components

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表 1 中低温煤焦油重油的基本性质

Table 1 Basic properties of heavy coal tar

Sample	Phenol w/%	Density(20 ℃) /(mg·cm^-3)	Moisture w/%	Carbon residue w/%	TI w/%	Ultimate analysis w_ad/%
Sample	Phenol w/%	Density(20 ℃) /(mg·cm^-3)	Moisture w/%	Carbon residue w/%	TI w/%	C	H	O^*	N	S
H-tar	30	1.066	3.76	3.14	0.84	79.17	7.88	11.93	0.85	0.17
^*: by difference

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表 2 H-CT和P的组成分析

Table 2 Composition analysis of H-CT and P

Sample	Group composition w/%			Ultimate analysis w_ad/%					C/H (atomic ratio)
Sample	TS	TI-QS	QI	C	H	O^*	N	S	C/H (atomic ratio)
H-CT	78.19	21.19	0.62	80.07	5.97	11.81	1.61	0.54	13.41
P	26.42	57.08	4.88	75.15	5.46	17.89	1.50	0.29	13.76
^*: by difference

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表 3 TS-H-CT、HS-P和HI-TS-P组分中部分组分分析

Table 3 Part of components detected by GC-MS in TS-H-CT, HS-P and HI-TS-P

No.	TS-H-CT		RT/ min	HS-P		RT/ min	HI-TS-P		RT/ min
No.	name of compound	relative area/%	RT/ min	name of compound	relative area/%	RT/ min	name of compound	relative area/%	RT/ min
1	p-xylene	1.36	4.56	isoquinoline	1.82	15.30	benzene, 1, 3-dimethyl-	9.57	4.55
2	phenol	1.59	7.53	quinoline, 2, 6-dimethyl-	0.65	22.73	o-xylene	2.47	5.08
3	phenol, 2-methyl-	1.05	10.16	hydroxytoluic acid	1.13	23.36	quinoline	0.92	18.19
4	acetophenone	0.57	10.60	quinoline, 2, 4-dimethyl-	0.75	23.63	bicyclo[3.2.1]oct -2-ene, 3-methyl-4-methylene-	0.82	27.03
5	phenol, 3-methyl-	4.30	11.02	1-naphthalenol, 2-methyl-	0.60	30.40	quinoline, 2, 4-dimethyl-	0.54	27.26
6	benzenemethanol, .alpha. , .alpha.-dimethyl-	0.80	11.41	dibenzofuran, 4-methyl-	0.56	30.93	naphthalene, 1-ethoxy-	0.65	30.47
7	phenol, 2, 4-dimethyl-	1.20	14.23	phenanthrene	1.77	36.19	1-naphthalenol, 2-methyl-	0.63	34.27
8	phenol, 4-ethyl-	1.71	15.12	dibenzo[b, e]7, 8- diazaBicYclo[2.2.2] octa-2, 5-diene	1.35	36.55	1-naphthalenol, 2-methyl-	0.58	34.54
9	phenol, 3, 4- dimethyl-	2.57	15.26	9H-fluorene, 9, 9-dimethyl-	0.65	37.90	1-naphthalenol, 2-methyl-	0.65	35.27
10	naphthalene	0.92	15.74	phenanthrene, 2-methyl-	0.84	40.61	1-naphthol, 5, 7-dimethyl-	0.68	38.10
11	phenol, 3, 4- dimethyl-	1.08	16.34	anthracene, 2-methyl-	1.44	40.92	1-naphthol, 6, 7-dimethyl-	0.55	38.20
12	catechol	0.58	16.78	anthracene, 9-methyl-	1.24	41.35	anthracene	0.82	40.11
13	phenol, 3-(1-methylethyl)-	0.57	17.94	anthracene, 2-methyl-	0.97	41.46	anthracene	0.68	40.48
14	benzene, 1-ethyl- 4-methoxy-	0.87	18.41	4-hydroxy-9- fluorenone	0.54	42.44	2H-isoindole, 4, 5, 6, 7-tetramethyl-	0.87	44.30
15	phenol, 2-ethyl- 4-methyl-	1.36	19.45	phenanthrene, 1, 7-dimethyl-	0.68	44.96	anthracene, 9-methyl-	0.71	45.29
16	1, 2-benzenediol, 3-methyl-	0.58	19.60	phenanthrene, 2, 5-dimethyl-	0.80	45.37	phenanthrene, 1-methyl-	0.54	45.40
17	1, 2-benzenediol, 4-methyl-	1.17	21.02	phenanthrene, 2, 5-dimethyl-	0.93	45.56	dibutyl phthalate	1.63	47.04
18	1H-inden-5-ol, 2, 3-dihydro-	1.29	23.01	fluoranthene	2.06	45.95	fluoranthene	1.29	49.90
19	1, 4-benzenediol, 2, 5-dimethyl-	0.62	23.70	dibenz[b, e]oxepin- 11(6H)-one	0.69	46.61	3, 4-dihydro-1- methyl-3-oxo-4- oxaphenanthrene	0.61	50.53
20	6-methyl- 4-indanol	0.76	27.64	pyrene	2.13	47.57	pyrene	1.52	51.52
21	1-naphthalenol	2.79	30.57	benzo[b]naphtho [2, 3-d]furan	0.74	47.90	3-phenanthrol	0.93	52.54
22	1-naphthalenol, 2-methyl-	1.14	34.21	benzo[b]naphtho [2, 3-d]furan	0.67	48.42	9-ahthraldehyde semicarbazone	1.35	52.90
23	1-naphthalenol, 2-methyl-	1.56	34.56	pyrene, 1-methyl-	0.81	49.79	pyrene, 1-methyl-	0.58	53.74
24	1-naphthalenol, 2-methyl-	1.47	34.65	11H-benzo[b] fluorene	2.05	50.67	11H-benzo[b] fluorene	1.31	54.62
25	1-naphthalenol, 2-methyl-	0.69	35.25	retene	4.22	50.94	retene	2.79	54.88
26	1-naphthalenol, 2-methyl-	1.50	35.42	11H-benzo[b] fluorene	1.08	51.20	pyrene, 1-methyl-	0.63	55.29
27	naphthalene, 1, 2-dihydro -2, 5, 8-trimethyl-	0.57	38.15	pyrene, 1-methyl-	0.73	51.36	pyrene, 1-methyl-	0.95	55.98
28	1-naphthol, 6, 7-dimethyl-	0.79	39.17	pyrene, 1-methyl-	0.79	52.24	pyrene, 1-methyl-	0.59	56.19
29	1-naphthol, 6, 7-dimethyl-	0.71	39.78	3-indolizineacetamide, N-(2hydroxyethyl)-. alpha.-oxo-2-phenyl-	2.25	52.90	1-phenyl-1H- inden-4-ol	0.99	56.68
30	2-dibenzofuranol	0.56	43.73	pyrene, 1, 3-dimethyl-	0.58	54.28	3-indolizineacetamide, N-(2-hydroxyethyl)-. alpha.-oxo-2-phenyl-	3.72	56.82
31	fluoranthene	0.51	49.97	pyrene, 1, 3-dimethyl-	0.66	54.83	pyridine, 3, 4-diphenyl-	0.52	58.54
32	pyrene	0.56	51.60	8-isopropyl-1, 3-dimethylphenanthrene	0.51	55.59	2-(2, 4, 6- cycloheptatrienylidene)1, 3-indandione	0.91	59.33
33	3-phenanthrol	1.53	52.69	2-(2, 4, 6- cycloheptatrienylidene) -1, 3-indandione	0.87	56.44	ethanone, 1-[4- (2-phenylethenyl)phenyl]-	0.99	59.78
34	retene	0.97	54.95	2-(2, 4, 6- cycloheptatrienylidene) -1, 3-indandione	0.94	57.21	indeno[2, 1-a] indene-5, 10-dione, 4b, 9b-dihydro-	1.39	60.37
35	1-phenyl-1 H-inden-4-ol	0.76	56.18	benz[a]anthracene	2.03	57.36	phenol, 2, 2'- methylenebis[6-(1, 1- dimethylethyl)-4-methyl-	0.52	60.80
36	pyrene, 1, 2, 3, 6, 7, 8-hexahydro-	0.96	56.82	triphenylene	1.56	57.64	2-(2, 4, 6- cycloheptatrienylidene) -1, 3-indandione	2.28	61.13
37	1-phenyl-1H- inden-4-ol	0.94	57.01	benz[a]anthracene, 7-methyl-	1.23	60.74	benz[a] anthracene	1.28	61.31
38	1H-Indole-3- carboxaldehyde, 2-phenyl-	1.04	57.12	8, 9-dihydro-7H- cyclopenta[a]pyrene	0.69	61.00	triphenylene	1.11	61.59
39	3, 7-diamino-5H-dibenzo a, d]cycloheptene	0.82	59.91	1-heptacosanol	0.73	61.41	indeno[2, 1-a] indene-5, 10-dione, 4b, 9b-dihydro-	0.57	61.69
40	indeno[2, 1-a] indene-5, 10-dione, 4b, 9b-dihydro-	0.79	60.65	benz[e] acephenanthrylene	1.66	65.34	quinoline, 4-styryl-	1.85	62.29
41	1, 2, 3, 4, 5, 6- hexahydrochrysene	0.65	61.49	1-heptacosanol	0.54	66.25	5(4H)- thebenidinone	1.07	64.21
42	2-methylbenzo[b]naphtha [2, 1-d]thiophene	0.59	63.90	dinaphtho [1, 2-b:1', 2'-d]furan	0.93	66.88	chrysene, 5-methyl-	0.93	64.70
43	1-pyrenemethanol	0.86	64.77	perylene	1.06	67.07	benz[a]anthracene, 12-methyl-	0.51	64.97
44	benz[e] acephenanthrylene	0.75	69.46	benz[e] acephenanthrylene	1.58	67.39	11H-indeno[1, 2-b] quinoline, 2-hydroxy-	0.56	67.38
45	benzo[a]pyren-7(8H) -one, 9, 10-dihydro-	0.67	75.55	8H-indeno[2, 1-b] phenanthrene	1.17	69.24	benz[e] acephenanthrylene	1.75	69.29
46	indeno[1, 2, 3-cd] pyrene	0.51	79.83	benz[j]aceanthrylene, 3-methyl-	0.52	70.32	dinaphtho [1, 2-b:1', 2'-d]furan	0.72	70.84
47				indeno [1, 2, 3-cd]pyrene	0.61	74.30	perylene	1.48	71.04
48				indeno[1, 2, 3-cd] pyrene	0.78	75.64	benz[e] acephenanthrylene	1.52	71.33
49							13H-dibenzo[a, h] fluorene	1.03	73.18
50							Benz[j]aceanthrylene, 3-methyl-	0.58	74.27
51							9, 10-anthracenedione, 1, 3, 8-trihydroxy-6-methyl-	1.56	75.11
52							indeno[1, 2, 3-cd] pyrene	0.84	78.26
53							benzo[ghi] perylene	1.76	79.61
54							benzo[ghi] perylene, 4-methyl-	0.58	83.01
55							perylo[1, 12-b, c, d] pyranone	0.82	83.24
56							perylo[1, 12-b, c, d] pyranone	0.58	83.78

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表 4 TS-H-CT与HI-TS-P中不同苯环数酚类和芳烃类物质的含量

Table 4 Content of various phenols and aromatics in TS-H-CT and HI-TS-P

		1 ring	2 rings	3 rings	4 rings	5 rings	6 rings
TS-H-CT	phenols /%	25.55	20.73	1.88	0.90	0.24	-
	aromatic hydrocarbons /%	4.86	4.25	3.83	5.45	2.81	1.17
HI-TS-P	phenols /%	1.08	6.09	1.49	-	-	-
	aromatic hydrocarbons /%	12.48	1.37	11.52	14.98	4.29	3.27

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表 5 H-CT、P及TI-QS组分的TG与DTG分析

Table 5 Analysis TG and DTG curves of H-CT, P and TI-QS

Sample		H-CT		P			TI-QS-H-CT		TI-QS-P
Stages	Ⅰ	Ⅱ	Ⅲ	Ⅰ	Ⅱ	Ⅰ	Ⅱ	Ⅲ	Ⅰ	Ⅱ
Initial weight loss Temperature t/℃	55	95	161	89	202	91	195	262	112	273
Final weight loss Temperature t/℃	95	161	521	202	731	195	262	656	273	755
Peak temperature t/℃	76	135	298	167	337	154	233	285	199	406
Stage weight loss w/%	1.20	5.12	79.16	4.01	57.61	11.83	10.22	32.70	10.09	37.70
Carbonization yield w/%		12.71		37.71			42.65		51.50

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中低温煤焦油重油正庚烷萃余物的反应(甲醛)分离与分析

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Reaction (formaldehyde) separation and analysis of n-heptane extraction residue from heavy oil of medium and low temperature coal tar

Corresponding author: SUN Ming, E-mail: sunming@nwu.edu.cn; MA Xiao-xun, E-mail: maxym@nwu.edu.cn

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2023年《燃料化学学报（中英文）》评优结果公布！

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中低温煤焦油重油正庚烷萃余物的反应(甲醛)分离与分析

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Reaction (formaldehyde) separation and analysis of n-heptane extraction residue from heavy oil of medium and low temperature coal tar

Corresponding author: SUN Ming, E-mail: sunming@nwu.edu.cn; MA Xiao-xun, E-mail: maxym@nwu.edu.cn

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2023年《燃料化学学报（中英文）》评优结果公布！