离子液体催化合成长链烷基萘基础油及其摩擦学性能

doi:10.16085/j.issn.1000-6613.2024-1078

化工进展 ›› 2025, Vol. 44 ›› Issue (9): 5277-5284.DOI: 10.16085/j.issn.1000-6613.2024-1078

• 精细化工 • 上一篇

离子液体催化合成长链烷基萘基础油及其摩擦学性能

刘通¹(), 乔韦军¹, 赵思萌¹, 赵志萍², 汤琼², 刘雷²(), 董晋湘²

^1.中国石油天然气股份有限公司大庆化工研究中心，黑龙江大庆 163714
^2.太原理工大学化学与化工学院，化学产品工程山西省重点实验室，山西太原 030024

收稿日期:2024-07-05 修回日期:2024-08-13 出版日期:2025-09-25 发布日期:2025-09-30
通讯作者: 刘雷
作者简介:刘通（1988—），男，高级工程师，博士研究生，研究方向为合成润滑油。E-mail：liutong459@petrochina.com.cn。
基金资助:
中国石油天然气股份有限公司科学研究与技术开发项目(2022DJ5910);山西省重点研发计划(202102090301005);山西省青年基金(202103021223064)

Synthesis of long-chain alkyl naphthalene base oil catalyzed by ionic liquids and its lubricating properties

LIU Tong¹(), QIAO Weijun¹, ZHAO Simeng¹, ZHAO Zhiping², TANG Qiong², LIU Lei²(), DONG Jinxiang²

^1.Daqing Petrochemical Research Center, PetroChina Company Limited, Daqing 163714, Heilongjiang, China
^2.Shanxi Key Laboratory of Chemical Product Engineering, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, Shanxi, China

Received:2024-07-05 Revised:2024-08-13 Online:2025-09-25 Published:2025-09-30
Contact: LIU Lei

摘要/Abstract

摘要：

烷基萘是一类重要的芳香基润滑基础油，具有优良的氧化安定性和配伍性质。萘和烯烃烷基化反应通常采用无机酸或固体酸作为催化剂，存在对反应装置腐蚀和反应温度高的缺点。本文采用酸性离子液体为催化剂，探索了萘和长链烯烃烷基化反应并合成润滑基础油，系统考察了离子液体组成、烯萘比、反应温度、烯烃滴加速度和催化剂用量对催化反应结果的影响，其中三乙胺盐酸盐和氯化铝形成的离子液体有利于多烷基产物的生成。通过调控十四烯和萘进料比例（1~3），合成了3种具有不同侧链烷基数目的烷基萘基础油，分别测试和评价了合成基础油的理化性质和摩擦学性能。实验结果表明，烷基萘侧链烷基的数目越多黏度越高，烯萘比为2的基础油具有最佳的黏度指数和适宜的黏度，作为润滑基础油在减摩和抗磨方面具有优势。

关键词: 离子液体, 催化, 合成, 长链烷基萘, 基础油, 摩擦学性能

Abstract:

Alkyl naphthalene, an important aromatic lubricating base oil, offers excellent oxidation stability and compatibility properties. Traditionally, the alkylation reaction of naphthalene and olefins utilizes inorganic acids and solid acids as catalysts, but these methods are plagued by equipment corrosion and high reaction temperatures. The paper explores the alkylation of naphthalene with tetradecene to synthesize lubricating base oil, with acidic ionic liquids as catalysts. This study investigates the effects of ionic liquid composition, olefin to naphthalene ratio, reaction temperature, olefin droplet rate, and catalyst dosage on the reaction results. The ionic liquid composed of triethylamine hydrochloride and aluminum chloride proves beneficial for generating polyalkylation products. By adjusting the feed ratio of tetradecane and naphthalene, three samples with different side chain alkyl groups were successfully synthesized. Subsequently, the physicochemical and tribological properties of the synthesized base oils were tested and evaluated. According to the experimental results, alkyl naphthalenes with more alkyl groups on the side chain exhibit higher viscosity. Among the synthesized base oils, the sample with the feed ratio of 2 demonstrates superior viscosity index and suitable viscosity, offering advantages in reducing wear and enhancing anti-wear properties as a lubricating base oil.

Key words: ionic liquids, catalysis, synthesis, long-chain alkyl naphthalene, base oil, tribological properties

中图分类号:

TQ241.5

刘通, 乔韦军, 赵思萌, 赵志萍, 汤琼, 刘雷, 董晋湘. 离子液体催化合成长链烷基萘基础油及其摩擦学性能[J]. 化工进展, 2025, 44(9): 5277-5284.

LIU Tong, QIAO Weijun, ZHAO Simeng, ZHAO Zhiping, TANG Qiong, LIU Lei, DONG Jinxiang. Synthesis of long-chain alkyl naphthalene base oil catalyzed by ionic liquids and its lubricating properties[J]. Chemical Industry and Engineering Progress, 2025, 44(9): 5277-5284.

图/表 12

参考文献 25

[1]	CHEN Shuoshuo, FAN Shuguang, SONG Ningning, et al. Load-carrying capacity and tribomechanism of DDA/MADE modified MoO₃ nanoparticle as an additive for alkylated naphthalene base oil[J]. Tribology International, 2024, 195(7): 109610.
[2]	YANG Tian, WANG Fajun, HUANG Jinpei, et al. Efficient continuous-flow synthesis of long-chain alkylated naphthalene catalyzed by ionic liquids in a microreaction system[J]. Reaction Chemistry & Engineering, 2021, 6(10): 1950-1960.
[3]	PEREGO Carlo, INGALLINA Patrizia. Recent advances in the industrial alkylation of aromatics: new catalysts and new processes[J]. Catalysis Today, 2002, 73(1/2): 3-22.
[4]	刘键, 刘恒源, 谭斌, 等. 芳烃长链烷基化催化工艺研究进展[J]. 化工进展, 2020, 39(5): 1744-1755.
	LIU Jian, LIU Hengyuan, TAN Bin, et al. Research progress in long chain catalytic alkylation of aromatic hydrocarbons[J]. Chemical Industry and Engineering Progress, 2020, 39(5): 1744-1755.
[5]	ZHANG Jie, HUANG Chongpin, CHEN Biaohua, et al. Isobutane/2-butene alkylation catalyzed by chloroaluminate ionic liquids in the presence of aromatic additives[J]. Journal of Catalysis, 2007, 249(2): 261-268.
[6]	WANG Mengke, KUAI Leiting, SHI Li, et al. Catalytic performance and industrial test of HY zeolite for alkylation of naphthalene and α-tetradecene[J]. New Journal of Chemistry, 2022, 46(5): 2290-2299.
[7]	KUAI Leiting, WANG Mengke, MENG Xuan, et al. W modified HY zeolite as catalyst for alkylation of aromatic[J]. Catalysis Letters, 2022, 152(8): 2480-2490.
[8]	ZHAO Zhongkui, QIAO Weihong, WANG Xiuna, et al. Effects of kinds of ionic liquid catalysts on alkylations of 1- and 2-methylnaphthalene with alkenes[J]. Applied Catalysis A: General, 2005, 290(1/2): 133-137.
[9]	LI Lei, ZHAO Xinrui, CHEN Chen, et al. Highly selective synthesis of polyalkylated naphthalenes catalyzed by ionic liquids and their tribological properties as lubricant base oil[J]. ChemistrySelect, 2019, 4(18): 5284-5290.
[10]	李媛媛, 汤琼, 陈晨, 等. 离子液体催化多乙基萘基础油的合成及润滑性能研究[J]. 燃料化学学报(中英文), 2023, 51(5): 635-643.
	LI Yuanyuan, TANG Qiong, CHEN Chen, et al. Synthesis of polyethylnaphthalenes base oil catalyzed by ionic liquid and its lubricating properties[J]. Journal of Fuel Chemistry and Technology, 2023, 51(5): 635-643.
[11]	TANG Qiong, ZHAO Zhiping, HAN Jun, et al. Insight into the catalytic behavior of ionic liquids and deactivation suppression technique in naphthalene alkylation[J]. Chemical Engineering Science, 2024, 292: 119993.
[12]	QI Guopeng, JIANG Feng, SUN Xuewen, et al. Alkylation mechanism of benzene with 1-dodecene catalyzed by Et₃NHCl-AlCl₃ [J]. Science China Chemistry, 2010, 53(5): 1102-1107.
[13]	QIAO Kun, DENG Youquan. Alkylations of benzene in room temperature ionic liquids modified with HCl[J]. Journal of Molecular Catalysis A: Chemical, 2001, 171(1-2): 81-84.
[14]	宋上飞, 刘青才, 吕升阳. 三氟甲磺酸催化萘烷基化研究[J]. 石油炼制与化工, 2018, 49(5): 71-74.
	SONG Shangfei, LIU Qingcai, Shengyang LYU. Alkylation of naphthalene catalyzed by trifluoromethanesulfonic acid[J]. Petroleum Processing and Petrochemicals, 2018, 49(5): 71-74.
[15]	NURMAKANOVA Asem, SALISCHEVA Anastasiya, CHUDINOVA Alyona, et al. Comparison between alkylation and transalkylation reactions using ab initio approach[J]. Procedia Chemistry, 2014, 10: 430-436.
[16]	LIU Yonghui, ZHOU Yuming, SHENG Xiaoli, et al. The catalytic performance study of chloroaluminate ionic liquids on long-chain alkenes alkylation[J]. Energy & Fuels, 2018, 32(9): 9763-9771.
[17]	HE Yibo, WAN Chao, ZHANG Qinghua, et al. Durability enhanced ionic liquid catalyst for Friedel-Crafts reaction between benzene and 1-dodecene: Insight into catalyst deactivation[J]. RSC Advances, 2015, 5(76): 62241-62247.
[18]	CAI Guangqing, LIU Zhefu, ZHANG Linzhou, et al. Quantitative structure-property relationship model for hydrocarbon liquid viscosity prediction[J]. Energy & Fuels, 2018, 32(3): 2190-3298.
[19]	ZHANG Wei, WU Jinquan, YU Senshen, et al. Modification and synthesis of low pour point plant-based lubricants with ionic liquid catalysis[J]. Renewable Energy, 2020, 153: 1320-1329.
[20]	BOWDEN Frank Philip, TABOR David. Mechanism of metallic friction[J]. Nature, 1942, 150: 197-199.
[21]	VELKAVRH Igor, KALIN Mitjan. Comparison of the effects of the lubricant-molecule chain length and the viscosity on the friction and wear of diamond-like-carbon coatings and steel[J]. Tribology International, 2012, 50: 57-65.
[22]	LI Haolin, MA Lin, WEN Ping, et al. Molecular structure insight into the tribological behavior of sulfonate ionic liquids as lubricants for titanium alloys[J]. Journal of Molecular Liquids, 2022, 357: 119082.
[23]	WANG Yanshuang, QIU Qingguo, ZHANG Pu, et al. Correlation between lubricating oil characteristic parameters and friction characteristics[J]. Coatings, 2023, 13(5): 881.
[24]	LU Renguo, MORIMOTO Masaya, TANI Hiroshi, et al. Tribological properties of alkyldiphenylethers in boundary lubrication[J]. Lubricants, 2019, 7(12): 112.
[25]	POLAJNAR Marko, Lucija ČOGA, KALIN Mitjan. Base lubricants for green stamping: The effects of their structure and viscosity on tribological performance[J]. Friction, 2023, 11(9): 1741-1754.

有机阳离子	萘转化率/%	烷基萘选择性/%			平均烷基化个数
有机阳离子	萘转化率/%	单烷基化	二烷基化	三烷基化	平均烷基化个数
MeNH₃Cl-AlCl₃	96.27	25.37	66.22	8.42	1.83
Me₂NH₂Cl-AlCl₃	89.81	44.08	40.76	15.16	1.71
Me₃NHCl-AlCl₃	90.98	38.13	39.04	22.83	1.85
EtNH₃Cl-AlCl₃	92.21	24.72	32.38	42.90	2.18
Et₂NH₂Cl-AlCl₃	93.20	24.69	35.93	39.38	2.15
Et₃NHCl-AlCl₃	94.03	27.41	40.19	32.40	2.05

有机阳离子	萘转化率/%	烷基萘选择性/%			平均烷基化个数
有机阳离子	萘转化率/%	单烷基化	二烷基化	三烷基化	平均烷基化个数
MeNH₃Cl-AlCl₃	96.27	25.37	66.22	8.42	1.83
Me₂NH₂Cl-AlCl₃	89.81	44.08	40.76	15.16	1.71
Me₃NHCl-AlCl₃	90.98	38.13	39.04	22.83	1.85
EtNH₃Cl-AlCl₃	92.21	24.72	32.38	42.90	2.18
Et₂NH₂Cl-AlCl₃	93.20	24.69	35.93	39.38	2.15
Et₃NHCl-AlCl₃	94.03	27.41	40.19	32.40	2.05

油品	KV40/mm²·s^-1	KV100/mm²·s^-1	VI	密度/g·cm^-3	倾点/℃	闪点/℃	苯胺点/℃	酸值/mg·g^-1
1	57.35	7.57	93	0.898	-41	230	66.0	0.0061
2	108.22	12.01	100	0.888	-34	260	87.6	0.0061
3	161.11	15.55	98	0.880	-28	275	116.0	0.0139
Synesstic 12	109.00	12.40	105	0.887	-36	258	90.0	＜0.05

油品	KV40/mm²·s^-1	KV100/mm²·s^-1	VI	密度/g·cm^-3	倾点/℃	闪点/℃	苯胺点/℃	酸值/mg·g^-1
1	57.35	7.57	93	0.898	-41	230	66.0	0.0061
2	108.22	12.01	100	0.888	-34	260	87.6	0.0061
3	161.11	15.55	98	0.880	-28	275	116.0	0.0139
Synesstic 12	109.00	12.40	105	0.887	-36	258	90.0	＜0.05

离子液体催化合成长链烷基萘基础油及其摩擦学性能

Synthesis of long-chain alkyl naphthalene base oil catalyzed by ionic liquids and its lubricating properties

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