C9+重芳烃催化加氢脱烷基技术研究进展

doi:10.16085/j.issn.1000-6613.2023-0410

摘要/Abstract

摘要：

随着我国芳烃联合装置、乙烯裂解装置的扩能或新建，国内C $9 +$ 重芳烃产量也大幅增加；利用催化加氢脱烷基技术将C $9 +$ 重芳烃转化为BTX等轻质芳烃，对炼化企业具有良好的经济效益。本文以C $9 +$ 重芳烃生产BTX为出发点，阐述了催化加氢脱烷基反应体系中的碳正离子机理和自由基机理，概述了国内外催化加氢脱烷基反应工艺和催化剂的研究进展，并分析了各工艺、催化剂的优缺点，最后对反应机理、工艺及催化剂的发展方向进行了展望。增产BTX的同时联产三甲苯、四甲苯等高附加值单体芳烃是未来催化加氢脱烷基工艺的发展方向。新型催化剂的研发方向则应结合具体的生产目标和反应机理，定向制备出高活性、高选择性、高稳定性的催化加氢脱烷基催化剂。

关键词: C $9 +$ 重芳烃, 催化加氢脱烷基, 反应机理, 工艺, 催化剂

Abstract:

The capacity expansion or new construction of aromatic complex and ethylene cracking plant in China led to a drastic increase in the yield of C $9 +$ heavy aromatics. The conversion of C $9 +$ heavy aromatics to BTX by catalytic hydrodealkylation technology would be conducive to improving economic benefits for refinery. Based on the production of BTX from C $9 +$ heavy aromatics, firstly, the mechanism of carbenium-ion and free radical in the reaction system of catalytic hydrodealkylation was emphasized. Secondly, the progress of the research on the hydrodealkylation process and catalysts in the domestic and foreign was summarized. Thirdly, the advantages and disadvantages of those process and catalysts was analyzed. Finally, the development direction of reaction mechanism, process and catalyst were forecasted. The future development direction of catalytic hydrodealkylation was to increase the production of BTX and simultaneously produce high value-added monomers such as tritoluene and tetratoluene. The research and development of novel catalysts should be combined with specific production objectives and reaction mechanisms, and the catalytic hydrodealkylation catalysts with high reaction activity, high selectivity and high stability should be prepared directionally.

Key words: C $9 +$ aromatics, catalytic hydrodealkylation, reaction mechanism, process, catalyst

中图分类号:

TQ241.1

张鹏飞, 严张艳, 任亮, 张奎, 梁家林, 赵广乐, 张璠玢, 胡志海. C $9 +$ 重芳烃催化加氢脱烷基技术研究进展[J]. 化工进展, 2024, 43(3): 1266-1274.

ZHANG Pengfei, YAN Zhangyan, REN Liang, ZHAGN Kui, LIANG Jialin, ZHAO Guangle, ZHANG Fanbin, HU Zhihai. Research progress in the catalytic hydrodealkylation of C $9 +$ heavy aromatics[J]. Chemical Industry and Engineering Progress, 2024, 43(3): 1266-1274.

图/表 8

表1 典型重整C9+重芳烃组成

组分	质量分数 /%	组分	质量分数 /%
异丙苯	0.697	邻甲乙苯	4.273
正丙苯	2.024	均三甲苯	12.839
间甲乙苯	12.704	偏三甲苯	37.802
对甲乙苯	4.534	连三甲苯	8.773
1-乙基-2,3-二甲基苯	1.981	1,2,4,5-四甲基苯	1.884
1-甲基,3-丙基苯	1.073	1,2,3,5-四甲基苯	2.713
1,3-二乙苯	0.733	1-甲基,4-丙基苯	0.820
萘	1.288	2-乙基,1,4-二甲基苯	1.413
茚满	1.719	1-甲基,2-丙基苯	0.427

图1 正丙苯借助碳正离子机理生成异丙苯和苯的反应历程

图2 多甲基苯借助碳正离子机理完成甲基转移的反应历程

图3 正丙苯借助自由基机理的反应历程

图4 Detol工艺流程

图5 HAL工艺流程

表2 文献中关于氧化物型催化剂的研究进展

载体	研究者	活性组分	原料	反应条件	性能指标
Al₂O₃	Daly等^[33]	Cr₂O₃-Na₂O	甲苯	620℃、5.5MPa、1.47h^-1	甲苯转化率>55%，苯选择性>90%
Al₂O₃	UOP^[3]	Cr₂O₃	C $9 +$ 芳烃	600～650℃、3.5～4.5MPa、0.5h^-1	高纯苯
Al₂O₃	王士文等^[34]	Cr₂O₃-RE	C₉~C₁₀	550℃、5MPa、1h^-1	C₉~C₁₀转化率>58.32%，BTX选择性>95.55%
SiO₂	石德先等^[3]	CrO _x	C $10 +$ 芳烃	550℃、5MPa、1h^-1	C $10 +$ 转化率>50%
Al₂O₃	Wu等^[35]	MoO₃-ZnO	C $9 +$ 芳烃	400～650℃、5h^-1、1.5～4.5MPa	C $9 +$ 转化率>50%，BTX收率>35%，BTX选择性≈70%
Al₂O₃	Ozawa等^[36]	MoO₃-NiO	C₉~C₁₀芳烃	550℃、6MPa	苯选择性9.74%，甲苯选择性30.27%，二甲苯选择性32.33%

表2 文献中关于氧化物型催化剂的研究进展

载体	研究者	活性组分	原料	反应条件	性能指标
Al₂O₃	Daly等^[33]	Cr₂O₃-Na₂O	甲苯	620℃、5.5MPa、1.47h^-1	甲苯转化率>55%，苯选择性>90%
Al₂O₃	UOP^[3]	Cr₂O₃	C $9 +$ 芳烃	600～650℃、3.5～4.5MPa、0.5h^-1	高纯苯
Al₂O₃	王士文等^[34]	Cr₂O₃-RE	C₉~C₁₀	550℃、5MPa、1h^-1	C₉~C₁₀转化率>58.32%，BTX选择性>95.55%
SiO₂	石德先等^[3]	CrO _x	C $10 +$ 芳烃	550℃、5MPa、1h^-1	C $10 +$ 转化率>50%
Al₂O₃	Wu等^[35]	MoO₃-ZnO	C $9 +$ 芳烃	400～650℃、5h^-1、1.5～4.5MPa	C $9 +$ 转化率>50%，BTX收率>35%，BTX选择性≈70%
Al₂O₃	Ozawa等^[36]	MoO₃-NiO	C₉~C₁₀芳烃	550℃、6MPa	苯选择性9.74%，甲苯选择性30.27%，二甲苯选择性32.33%

表3 文献中关于分子筛型催化剂的研究进展

载体	研究者	活性组分	原料	反应条件	性能指标
ZSM-5	杨纪等^[42]	Pt/Pd	C $9 +$ 芳烃	480℃、1.4MPa、5h^-1	BTX选择性约70%
	RIPP^[43]	Pt、Sn、Re或Pd	C $9 +$ 芳烃	375~390℃、0.80~0.85MPa、1~4h^-1	BTX收率>70%
	董娇娇等^[44]	Mo	C $9 +$ 芳烃	550℃、3MPa、3.6h^-1	C $9 +$ 转化率>55.9%，BTX选择性>90%
	Arca等^[45]	Pt-Mo	C₈~C₁₃	400~650℃、2~4MPa	液体产物中BTX质量分数达75%
β	申群兵^[12]	NiO/MoO₃	C $9 +$ 芳烃	460℃、3MPa、3.62h^-1	C $9 +$ 转化率>80%，BTX收率>50%，BTX选择性>70%
Y	孙彦民等^[46]	Y₂O₃-Pt	C $10 +$ 芳烃	350~370℃、2~3MPa、1~2h^-1	C₈、C₉总选择性大于40%
MCM-56	何剑洪等^[47]	La₂O₃-NiO	C $9 +$ 芳烃	460℃、3MPa、3.62h^-1	C $9 +$ 转化率75.2%，BTX收率63.4%，BTX选择性84.2%

表3 文献中关于分子筛型催化剂的研究进展

载体	研究者	活性组分	原料	反应条件	性能指标
ZSM-5	杨纪等^[42]	Pt/Pd	C $9 +$ 芳烃	480℃、1.4MPa、5h^-1	BTX选择性约70%
	RIPP^[43]	Pt、Sn、Re或Pd	C $9 +$ 芳烃	375~390℃、0.80~0.85MPa、1~4h^-1	BTX收率>70%
	董娇娇等^[44]	Mo	C $9 +$ 芳烃	550℃、3MPa、3.6h^-1	C $9 +$ 转化率>55.9%，BTX选择性>90%
	Arca等^[45]	Pt-Mo	C₈~C₁₃	400~650℃、2~4MPa	液体产物中BTX质量分数达75%
β	申群兵^[12]	NiO/MoO₃	C $9 +$ 芳烃	460℃、3MPa、3.62h^-1	C $9 +$ 转化率>80%，BTX收率>50%，BTX选择性>70%
Y	孙彦民等^[46]	Y₂O₃-Pt	C $10 +$ 芳烃	350~370℃、2~3MPa、1~2h^-1	C₈、C₉总选择性大于40%
MCM-56	何剑洪等^[47]	La₂O₃-NiO	C $9 +$ 芳烃	460℃、3MPa、3.62h^-1	C $9 +$ 转化率75.2%，BTX收率63.4%，BTX选择性84.2%

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