Inorganic Chemicals Industry >
Research status and prospects of olefin removal catalyst from aromatic reforming oil
Received date: 2024-04-26
Online published: 2024-06-13
Benzene，toluene，xylene（BTX） is wildly used to synthetize high value products such as rubber，textile fibers，pharmaceuticals，and spices as an important raw materials of organic chemical.Recently，with the rapidly development of domestic petrochemical industry，the demand for BTX was increased by 2%~6% annually.In addition，the increasingly stringent environmental requirements for aromatics reforming technology promoted the continuous development of olefin removal catalyst for aromatic reforming oil.Based on these points，the research status and existed problems of two traditional olefin removal agents including the granular activated clay and selective hydrogenation refining catalysts were summarized firstly.Then，the catalysis，deactivation mechanism and industrial application status of emerging zeolite catalysts were emphatically introduced.Finally，the modification methods of zeolite were reviewed from three aspects：morphology and grain size regulation，pore structure controlment，and acidity adjustment.The design and development directions of molecular sieve catalysts for future industrial aromatics continuous reforming units were pointed out.
Key words： aromatics; trace olefins; deolefin agent; catalytic alkylation; zeolite
FAN Jingxin , LI Bin , HONG Luwei , HONG Meihua , GONG Xin . Research status and prospects of olefin removal catalyst from aromatic reforming oil[J]. Inorganic Chemicals Industry, 2025 , 57(2) : 14 -25 . DOI: 10.19964/j.issn.1006-4990.2024-0233
| 1 | YAO Xiaoyu， MENG Xuan， LIU Naiwang，et al.Polyethylene glycol-based halogen-free acidic deep eutectic solvents for removal of olefins from aromatics［J］.Fuel，2024，357：130070. |
| 2 | 嵇大勇，潘龙.连续重整装置生成油脱烯烃技术方案比较和选择［J］.炼油技术与工程，2022，52（1）：33-35. |
| JI Dayong， PAN Long.Comparison and selection of technical schemes for olefin removal from produced oil in continuous reforming unit［J］.Petroleum Refinery Engineering，2022，52（1）：33-35. | |
| 3 | 黄志遥，肖雪洋，薛金召，等.催化重整生成油脱烯烃技术的现状及研究［J］.化工设计通讯，2020，46（10）：82-83. |
| HUANG Zhiyao， XIAO Xueyang， XUE Jinzhao，et al.Current status and research on deolefin technology of catalytic reforming oil［J］.Chemical Engineering Design Communications，2020，46（10）：82-83. | |
| 4 | WANG Sitan， MENG Xuan， LIU Naiwang，et al.Effective catalyst for removing trace olefins from reforming aromatics：Sulfated zirconia with high sulfur content synthesized by sulfonation with chlorosulfonic acid［J］.Industrial & Engineering Chemistry Research，2022，61（15）：5103-5116. |
| 5 | 王涛.重整生成油烯烃产生机理及其脱除技术研究进展［J］.炼油技术与工程，2023，53（7）：5-9. |
| WANG Tao.Production mechanism of olefins in reformate and research progress of its removal technology［J］.Petroleum Refinery Engineering，2023，53（7）：5-9. | |
| 6 | ROUHANI H， FARHADI F.Detecting and evaluating detrimental factors of clay′s longevity，selecting，and optimizing an appropriate adsorbent for operating time elevation in the separation process of trace olefins from aromatics［J］.Industrial & Engineering Chemistry Research，2020，59（7）：2796-2804. |
| 7 | REN Kaiqing， LIU Jianfei， WANG Xin，et al.Iron modified SO4 2–/ZrO2 in application of removing trace olefins from aromatics［J］.Petroleum Science and Technology，2019，37（1）：8-14. |
| 8 | 王品，王海娟，牛国庆，等.不同钠盐改性蒙脱土的制备及表征［J］.当代化工，2020，49（5）：773-776. |
| WANG Pin， WANG Haijuan， NIU Guoqing，et al.Preparation and characterization of different sodium salt modified montmorillonite［J］.Contemporary Chemical Industry，2020，49（5）：773-776. | |
| 9 | NOURI N， TASVIRI M， GHASEMZADEH H.Developing an efficient catalyst based on thermal and acid-treated clay for the removal of trace olefins from aromatic compounds［J］.Clays and Clay Minerals，2021，69（1）：105-116. |
| 10 | ROUHANI H， FARHADI F， AKBARI KENARI M，et al.Optimizing temperature and introducing new process arrangements for elevating clay′s longevity based on the known poisons in the separation process of trace olefins from aromatics［J］.Journal of Chemical Technology & Biotechnology，2022，97（4）：973-983. |
| 11 | 吴文娟，陈昌伟，江正洪，等.活性膨润土的改性及其在芳烃脱烯烃中的应用［J］.金属矿山，2009（5）：146-148. |
| WU Wenjuan， CHEN Changwei， JIANG Zhenghong，et al.Modification of active bentonite and its application in olefins removal from aromatics［J］.Metal Mine，2009（5）：146-148. | |
| 12 | 江正洪，曾海平，翁惠新，等.活性白土负载AlCl3催化剂对脱除芳烃中微量烯烃反应的性能研究［J］.矿物岩石，2010，30（4）：17-20. |
| JIANG Zhenghong， ZENG Haiping， WENG Huixin，et al.The activity in removing trace olefins of aromatic hydrocarbons by using activated clay supported AlCl3 ［J］.Journal of Mineralogy and Petrology，2010，30（4）：17-20. | |
| 13 | GUO Haijun， ZHANG Hairong， LI Qinglin，et al.Removal of olefins from reforming aromatic hydrocarbons over metal-halide-modified acid-activated palygorskite［J］.Energy & Fuels，2020，34（8）：9463-9472. |
| 14 | LI Guoliang， LUAN Jinning， ZENG Xiansong，et al.Removal of trace olefins from aromatics over metal-halides-modified clay and its industrial test［J］.Industrial & Engineering Chemistry Research，2011，50（11）：6646-6649. |
| 15 | YAO Xiaoyu， LUO Tianyi， YIN Tao，et al.Gas-assisted exfoliation montmorillonite into mono-layered nanosheets for the removal of olefins from aromatics［J］.Fuel，2021，306：121720. |
| 16 | WANG Sitan， MENG Xuan， LIU Naiwang，et al.Alkylation for removing trace olefins from reforming aromatics over novel Al2O3@SO4 2-/ZrO2 catalysts derived from the ZrO2-coated γ-Al2O3 strategy［J］.Separation and Purification Technology，2023，308：122731. |
| 17 | OH Y， SHIN J，NOH H，et al.Selective hydrotreating and hydrocracking of FCC light cycle oil into high-value light aromatic hydrocarbons［J］.Applied Catalysis A：General，2019，577：86-98. |
| 18 | YAO Xiaoyu， MENG Xuan， YIN Jie，et al.Efficient removal of trace olefins in aromatics by novel acetamide-based acidic deep eutectic solvents［J］.Fuel，2022，316：123103. |
| 19 | 张孔远，周然然，燕京，等.LH-02催化剂在重整石脑油后加氢中的应用［J］.石化技术与应用，2004，22（3）：188-189，196. |
| ZHANG Kongyuan， ZHOU Ranran， YAN Jing，et al.Application evaluation of LH-02 hydrofining catalyst for naphtha reforming［J］.Petrochemical Technology & Application，2004，22（3）：188-189，196. | |
| 20 | 黄志遥.液相选择性加氢脱除重整生成油中微量烯烃的研究［D］.长沙：中南大学，2021. |
| HUANG Zhiyao.Study on removal of trace olefins from reformed oil by liquid phase selective hydrogenation［D］.Changsha：Central South University，2021. | |
| 21 | MA Haowen， WANG Jiayi， ZHAN Xuecheng，et al.Identification of PdPt alloys for preferential C6 olefin hydrogenation over aromatic hydrocarbons through density functional theory and microkinetic modeling［J］.Chemical Communications，2023，59（43）：6529-6532. |
| 22 | 郭宇栋.重整生成油选择加氢脱除微量烯烃Ni基催化剂的研究［D］.东营：中国石油大学（华东），2021. |
| GUO Yudong.Study on Ni-based catalyst for selective hydrogenation of reformate to remove trace olefins［D］.Dongying：China University of Petroleum（Huadong），2021. | |
| 23 | 孟祥堃，张晓昕，宗保宁，等.磁稳定床反应器重整生成油后加氢过程研究［J］.石油炼制与化工，2002，33（4）：1-4. |
| MENG Xiangkun， ZHANG Xiaoxin， ZONG Baoning，et al.Study on process of selective hydrogenation of olefins in reformate using magnetically stabilized bed reactor［J］.Petroleum Processing and Petrochemicals，2002，33（4）：1-4. | |
| 24 | ZHANG Xiaoxin， MA Aizeng， MU Xuhong，et al.Selective hydrogenation of reformate oils over amorphous NiB/SiO2 catalyst［J］.Catalysis Today，2002，74（1/2）：77-84. |
| 25 | CHU Weifeng， LIU Shenglin， XIN Wenjie，et al.Effect of binder type on MWW-based catalysts for the liquid-phase alkylation reaction of benzene with ethylene［J］.Industrial & Engineering Chemistry Research，2022，61（7）：2693-2700. |
| 26 | KONG Xiangyou， ZHAO Jinyang， HUO Kai，et al.Mechanistic insights into the effects of alkali metal ion on ZSM-11 zeolite synthesis and its catalytic alkylation performance［J］.Microporous and Mesoporous Materials，2023，347：112352. |
| 27 | 张孔远，马亮，张唯稚，等.工业C8 +芳烃馏分脱烯烃催化剂失活原因分析［J］.石油炼制与化工，2023，54（5）：42-47. |
| ZHANG Kongyuan， MA Liang， ZHANG Weizhi，et al.Cause analysis of deactivation of industrial deolefinization catalyst for C8 + aromatics fraction［J］.Petroleum Processing and Petrochemicals，2023，54（5）：42-47. | |
| 28 | DíAZ M， EPELDE E， VALECILLOS J，et al.Coke deactivation and regeneration of HZSM-5 zeolite catalysts in the oligomerization of 1-butene［J］.Applied Catalysis B：Environmental，2021，291：120076. |
| 29 | CHEN Changwei， WU Wenjuan， ZENG Xiansong，et al.Study on several mesoporous materials catalysts applied to the removal of trace olefins from aromatics and commercial sidestream tests［J］.Industrial & Engineering Chemistry Research，2009，48（23）：10359-10363. |
| 30 | 江正洪.催化法脱除芳烃中微量烯烃的研究［D］.上海：华东理工大学，2012. |
| JIANG Zhenghong.Study on catalytic removal of trace olefins from aromatic hydrocarbons［D］.Shanghai：East China University of Science and Technology，2012. | |
| 31 | 濮鑫.重整油中微量烯烃精制催化剂的制备、表征及其性能研究［D］.上海：华东理工大学，2015. |
| PU Xin.Preparation，characterization and performance of catalyst for refining trace olefins in reforming oil［D］.Shanghai：East China University of Science and Technology，2015. | |
| 32 | REDDY J K， LAD S， MANTRI K，et al.Zeolite-based catalysts for the removal of trace olefins from aromatic streams［J］.Applied Petrochemical Research，2020，10（3）：107-114. |
| 33 | SAXENA S K， VISWANADHAM N， AL-MUHTASEB A H.Effect of zeolite pore morphology on solvent-less alkylation of benzene with 1-hexene［J］.Materials Today Chemistry，2017，4：45-52. |
| 34 | LAREDO G C， CASTILLO J J， NAVARRETE-BOLA?OS J，et al.Benzene reduction in gasoline by alkylation with olefins：Comparison of beta and MCM-22 catalysts［J］.Applied Catalysis A：General，2012，413：140-148. |
| 35 | ZHAO Zhongkui， LI Zongshi， QIAO Weihong，et al.Alkylation of α-methylnaphthalene with long-chain olefins over large-pore zeolites［J］.Catalysis Letters，2004，98（2）：145-151. |
| 36 | GUO Shuai， WU Yushan， JIN Tao，et al.Controllable alkylation of benzene with mixed olefins for producing C8-C15 aromatics in jet fuel［J］.Fuel，2020，275：117890. |
| 37 | 王凌涛，刘冠锋，于海斌，等.一种小晶粒NaY分子筛的制备方法：中国，105314651A［P］.2016-02-10. |
| 38 | SCHULMAN E， WU Wei， LIU Dongxia.Two-dimensional zeolite materials：Structural and acidity properties［J］.Materials，2020，13（8）：1822. |
| 39 | LIANG Ben， LIU Mengnan， AN Ning，et al.Achieving long-lived MWW zeolite catalyst for alkylation of benzene with 1-dodecene：Insights into confinement effect of surface cavities and underlying mechanism［J］.Chemical Engineering Journal，2024，489：151109. |
| 40 | 潘盛山.ROC-Z1重整油脱烯烃催化剂的首次工业应用［J］.石油炼制与化工，2014，45（2）：46-49. |
| PAN Shengshan.First commercial application of olefin removal catalyst of ROC-Z1［J］.Petroleum Processing and Petrochemicals，2014，45（2）：46-49. | |
| 41 | 霍道勤，龚燕芳，王月梅，等.DOT-100重整油脱烯烃催化剂的工业化应用［J］.石油化工技术与经济，2013，29（1）：42-44. |
| HUO Daoqin， GONG Yanfang， WANG Yuemei，et al.Commercial application of DOT-100 reformate de-olefin catalyst［J］.Technology & Economics in Petrochemicals，2013，29（1）：42- 44. | |
| 42 | 陈颖超.TCDTO-1重整油脱烯烃催化剂的工业应用［J］.化工管理，2014（21）：65. |
| CHEN Yingchao.Industrial application of TCDTO-1 reforming oil olefin removal catalyst［J］.Chemical Enterprise Management，2014（21）：65. | |
| 43 | 臧甲忠，于海斌，刘冠锋，等.TCDTO-1重整生成油精制催化剂工业侧线试验［J］.无机盐工业，2012，44（6）：54-56. |
| ZANG Jiazhong， YU Haibin， LIU Guanfeng，et al.Bypass experiment of TCDTO-1 catalyst for refining process of reforming generation oil［J］.Inorganic Chemicals Industry，2012，44（6）：54- 56. | |
| 44 | 张婷.分子筛改性及其在烷基化脱除芳烃中的烯烃的研究［D］.上海：华东理工大学，2021. |
| ZHANG Ting.Study on modification of molecular sieve and its application in alkylation to remove olefins from aromatic hydrocarbons［D］.Shanghai：East China University of Science and Technology，2021. | |
| 45 | 黄朝晖，刘乃旺，姚佳佳，等.USY分子筛表面酸性的调变及其在催化脱除芳烃中烯烃的应用［J］.化工进展，2016，35（1）：138-144. |
| HUANG Zhaohui， LIU Naiwang， YAO Jiajia，et al.Surface acid modification of zeolite and its application in removal of olefins in aromatics［J］.Chemical Industry and Engineering Progress，2016，35（1）：138-144. | |
| 46 | 王月梅，李为，童伟益，等.USY分子筛酸处理对催化脱烯烃性能的影响［J］.化学反应工程与工艺，2023，39（4）：319-326. |
| WANG Yuemei， LI Wei， TONG Weiyi，et al.Acid treatment of USY zeolite and its effect on catalytic performance in deolefinization［J］.Chemical Reaction Engineering and Technology，2023，39（4）：319-326. | |
| 47 | YU Haibin， ZANG Jiazhong， LIU Guanfeng，et al.Acid-modified hierarchical porous rare-earth-containing Y zeolite as a highly active and stable catalyst for olefin removal［J］.ACS Omega，2020，5（29）：18028-18034. |
| 48 | 洪美花，臧甲忠，王凌涛，等.硼掺杂Y分子筛的合成、改性及烯烃脱除性能研究［J］.无机盐工业，2022，54（12）：139-147. |
| HONG Meihua， ZANG Jiazhong， WANG Lingtao，et al.Study on synthesis，modification and olefin removal performance of boron-doped Y zeolite［J］.Inorganic Chemicals Industry，2022，54（12）：139-147. | |
| 49 | 张婷，孟璇，施力，等.氟盐溶液处理对Beta分子筛结构、酸性及催化烷基化反应活性的影响［J］.石油炼制与化工，2021，52（12）：54-59. |
| ZHANG Ting， MENG Xuan， SHI Li，et al.Effect of fluorine treatment on the structure，acidity and catalytic activity of beta zeolite［J］.Petroleum Processing and Petrochemicals，2021，52（12）：54-59. | |
| 50 | RAMAN G，DAS J， MANTRI K，et al.Highly efficient mesoporous ZSM-5 for trace olefin removal from aromatic stream［J］.Inorganica Chimica Acta，2023，544：121201. |
| 51 | REDDY J K， MANTRI K， LAD S，et al.Synthesis of Ce-MCM-22 and its enhanced catalytic performance for the removal of olefins from aromatic stream［J］.Journal of Porous Materials，2020，27（6）：1649-1658. |
| 52 | 龙有，匡良斌，周亚新，等.DOT-300重整油脱烯烃催化剂工业试验［J］.化学反应工程与工艺，2022，38（3）：283-288. |
| LONG You， KUANG Liangbin， ZHOU Yaxin，et al.Industrial application of a catalyst for olefin removal from DOT-300 reformate［J］.Chemical Reaction Engineering and Technology，2022，38（3）：283-288. | |
| 53 | 吴青，侯章贵，兰晓光，等.C8 +重整混合芳烃精制催化剂TCDTO-1的研制［J］.现代化工，2014，34（10）：99-102，104. |
| WU Qing， HOU Zhanggui， LAN Xiaoguang，et al.TCDTO-1 catalyst for refining process of mixed C8 + aromatics［J］.Modern Chemical Industry，2014，34（10）：99-102，104. | |
| 54 | 王一男，于鲁杰，王昕，等.分子筛催化芳烃烷基化脱烯烃的研究［J］.精细石油化工，2007，24（1）：1-4. |
| WANG Yinan， YU Lujie， WANG Xin，et al.Molecular sieve catalysts for removing olefins from aromatic hydrocarbons by alkylation reaction［J］.Speciality Petrochemicals，2007，24（1）：1-4. | |
| 55 | 任杰，许响生，李小青，等.一种重整芳烃精制方法：中国，114891534A［P］.2022-08-12. |
| 56 | 江正洪，陈昌伟，翁惠新，等.用于芳烃中微量烯烃脱除的MCM-22催化剂的研究［J］.现代化工，2009，29（12）：40-42. |
| JIANG Zhenghong， CHEN Changwei， WENG Huixin，et al.Study on MCM-22 catalysts of removing trace olefins from aromatic hydrocarbons［J］.Modern Chemical Industry，2009，29（12）：40-42. | |
| 57 | 曾拥军，王一男，王昕，等.氢氧化铌改性沸石分子筛的表面酸性及其催化活性［J］.化学世界，2007，48（11）：641-645. |
| ZENG Yongjun， WANG Yinan， WANG Xin，et al.Surface acidity and catalytic activity of Nb（OH）5-modified zeolite［J］.Chemical World，2007，48（11）：641-645. | |
| 58 | 李季伟，姚志龙，李梦晨，等.改性Y型分子筛非临氢催化脱除重整芳烃中的烯烃［J］.工业催化，2014，22（8）：609-613. |
| LI Jiwei， YAO Zhilong， LI Mengchen，et al.Research on modified Y zeolite for non-hydrogen catalytic removal of olefin in aromatics［J］.Industrial Catalysis，2014，22（8）：609-613. |
/
| 〈 |
|
〉 |