Citation: Chen Zhang, Xin Wen Guo, Ya Nan Wang, Xiang Sheng Wang, Chun Shan Song. Methylation of 2-methylnaphthalene with methanol to 2,6-dimethylnaphthalene over HZSM-5 modified by NH₄F and SrO[J]. Chinese Chemical Letters, ;2007, 18(10): 1281-1284. doi: 10.1016/j.cclet.2007.07.025 shu

Methylation of 2-methylnaphthalene with methanol to 2,6-dimethylnaphthalene over HZSM-5 modified by NH₄F and SrO

a State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, China;
b Clean Fuels and Catalysis Program, The Energy Institute and Department of Energy & Geo-Environmental Engineering, The Pennsylvania State University, 209 Academic Projects Building, University Park, PA 16802, USA

Received Date: 6 March 2007

Fund Project: The project was supported by Program for New Century Excellent Talents in University (no.NCET-04-0268) and by the 111 Project.

The methylation of 2-methylnaphthalene (2-MN) into 2, 6-dimethylnaphthalene (2, 6-DMN) was investigated over the solid acid catalysts. The results show that HZSM-5 modified by NH₄F has better catalytic performance than parent HZSM-5 due to the decrease in the acidity. When NH₄F/HZSM-5 is further modified by SrO, its catalytic activity decreases due to the decrease in the total acid amount and acidic strength. As a result, the comprehensive modification of NH₄F and SrO leads to the increase in the 2, 6-DMN selectivity (2, 6-DMN to DMN), up to 64.8% when 2-MN conversion is 10%. We calculated the ESP charge by density functional theory and the results show that the 6-position in 2-MN has higher ESP charge value than 7-position. The formation of 2, 6-DMN is favored energetically as compared to that for 2, 7-DMN. This suggests during the alkylation of 2-MN inside the ZSM-5 channel, the formation of 2, 6-DMN is favored electronically than that of 2, 7-DMN. Hence, lowering the acidity of catalyst is a key factor to obtain high selectivity of 2, 6-DMN.
- 2,6-DMN,
- Modification,
- Selectivity,
- ESP charge
1. [1]
  Yan Zhao , Zhenming Tian , Qisen Jia , Ting Yao , Jiashu Li , Yanan Wang , Xuejing Cui , Jing Liu , Xin Chen , Luhua Jiang . Crystal orientation dependent charge transfer dynamics and interfacial water configuration boosting photoelectrocatalytic water oxidation to H2O2. Chinese Journal of Structural Chemistry, 2025, 44(7): 100619-100619. doi: 10.1016/j.cjsc.2025.100619
2. [2]
  Yajun Gao , Xinyu Yang , Jian Su , Zhizhong Li . A stable scandium(III) metal-organic framework with introduced nitrate ions for enhancing C₂H₆/C₂H₄ selectivity in the separation of MTO products. Chinese Journal of Structural Chemistry, 2025, 44(6): 100576-100576. doi: 10.1016/j.cjsc.2025.100576
3. [3]
  Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
4. [4]
  Yongli Zhao , Dingsheng Cao , Jie-Ping Wan , Yunyun Liu . Synthesis of 3-phosphinyl chromones via in situ iodination mediated C-H phosphination and the tunable synthesis of 2-phosphoryl chromanones. Chinese Chemical Letters, 2026, 37(1): 111740-. doi: 10.1016/j.cclet.2025.111740
5. [5]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
6. [6]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
7. [7]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
8. [8]
  Qiao Wang , Ziling Jiang , Chuang Yu , Liping Li , Guangshe Li . Research progress of inorganic sodium ion conductors for solid-state batteries. Chinese Chemical Letters, 2025, 36(6): 110006-. doi: 10.1016/j.cclet.2024.110006
9. [9]
  Zimo Yang , Yan Tong , Yongbo Liu , Qianlong Liu , Zhihao Ni , Yuna He , Yu Rao . Developing selective PI3K degraders to modulate both kinase and non-kinase functions. Chinese Chemical Letters, 2024, 35(11): 109577-. doi: 10.1016/j.cclet.2024.109577
10. [10]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
11. [11]
  Junyi Yu , Yin Cheng , Anhong Cai , Xianfeng Huang , Qingrui Zhang . Synthetic Cu(Ⅲ) from copper plating wastewater for onsite decomplexation of Cu(Ⅱ)- and Ni(Ⅱ)-organic complexes. Chinese Chemical Letters, 2025, 36(2): 110549-. doi: 10.1016/j.cclet.2024.110549
12. [12]
  Weidan Meng , Yanbo Zhou , Yi Zhou . Green innovation unleashed: Harnessing tungsten-based nanomaterials for catalyzing solar-driven carbon dioxide conversion. Chinese Chemical Letters, 2025, 36(2): 109961-. doi: 10.1016/j.cclet.2024.109961
13. [13]
  Ying Wang , Hong Yang , Caixia Zhu , Qing Hong , Xuwen Cao , Kaiyuan Wang , Yuan Xu , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Cascading oxidoreductases-like nanozymes for high selective and sensitive fluorescent detection of ascorbic acid. Chinese Chemical Letters, 2025, 36(4): 110153-. doi: 10.1016/j.cclet.2024.110153
14. [14]
  Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
15. [15]
  Bo Li , Yuanzhe Cheng , Xuyang Ma , Dongxu Zhao , Yang Zhang , Yongxing Sun , Jia Chen , Li Wu , Liang Zhao , Hongdeng Qiu , Yujian He . Facile and scale-up synthesis of cyano-functionalized covalent organic frameworks for selective gold recovery. Chinese Chemical Letters, 2026, 37(1): 111134-. doi: 10.1016/j.cclet.2025.111134
16. [16]
  Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO₂ Reduction by Modified g-C₃N₄. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-0. doi: 10.3866/PKU.WHXB202408005
17. [17]
  Shaoming Dong , Yiming Niu , Yinghui Pu , Yongzhao Wang , Bingsen Zhang . Subsurface carbon modification of Ni-Ga for improved selectivity in acetylene hydrogenation reaction. Chinese Chemical Letters, 2024, 35(12): 109525-. doi: 10.1016/j.cclet.2024.109525
18. [18]
  Yu Liu , Pengfei Li , Yize Liu , Zaicheng Sun . Recent advances in carbon dots as a single photocatalyst. Acta Physico-Chimica Sinica, 2026, 42(2): 100167-0. doi: 10.1016/j.actphy.2025.100167
19. [19]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
20. [20]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611