Synthesis of high viscosity alkylated acenaphthene and investigation of their lubrication property

doi:10.11949/0438-1157.20220523

Abstract

Abstract:

At present, lubricating base oil mainly comes from petroleum resources. Based on the current situation of rich coal and lean oil in China, it is of great significance to develop a process route for synthesizing lubricating base oil from coal-based raw materials. Acenaphthene and α-olefins are the products of coal coking and coal-to-oils, respectively. Herein, the ionic liquid ([Et₃NH][Al₂Cl₇]) was used as catalyst for the acenaphthene alkylation with α-olefins (C₆ and C₈) to produce high-viscosity lubricating base oil. Four alkylated acenaphthene products with various alkyl lengths were obtained by adjusting the feeding ratio, and their structures were analyzed by GC and GC-MS. Moreover, the physicochemical properties of synthetic oils were investigated to reveal their structure-properties relationship, the synthetic alkylated products showed high viscosity (10.1—19.5 mm²·s^-1, 100℃), the aniline points (<63℃), and the oxidative onset temperatures (>190℃). The alkylated acenaphthenes as base oils displayed excellent tribological performance, the increase of side-chains on acenaphthene was beneficial to enhance their load-carrying capacity and tribological property.

Key words: ionic liquid, lubricating base oil, acenaphthene, olefin, alkylation

摘要：

目前润滑基础油主要来源于石油资源，基于我国富煤贫油的现状，开发煤基原料合成润滑基础油的工艺路线具有重要意义。以煤化工过程产生的多环芳烃（苊）和烯烃为原料，以离子液体（[Et₃NH][Al₂Cl₇]）为催化剂通过烷基化反应探索了高黏度润滑基础油的合成。通过调控烯烃（己烯或辛烯）和苊的反应比例，合成了四种不同组成和结构的多烷基苊基础油，通过GC和GC-MS对其成分进行了分析。对不同油品的物化性能指标进行表征，揭示了产物组成结构和性质的关系，烷基苊基础油具有高的黏度（10.1~19.5 mm²·s^-1，100℃）、苯胺点（<63℃）和起始氧化温度（>190℃）；同时，烷基苊作为润滑基础油表现出优良的摩擦学性能，且随着苊环侧链烷基化程度的增加，其抗载荷能力会增强。

关键词: 离子液体, 润滑基础油, 苊, 烯烃, 烷基化

CLC Number:

TQ 241.5

Jingze CUI, Qiong TANG, Chen CHEN, Yujie LIU, Hong XU, Lei LIU, Jinxiang DONG. Synthesis of high viscosity alkylated acenaphthene and investigation of their lubrication property[J]. CIESC Journal, 2022, 73(8): 3659-3668.

崔敬泽, 汤琼, 陈晨, 刘宇婕, 徐红, 刘雷, 董晋湘. 高黏度烷基苊基础油的合成及润滑性能研究[J]. 化工学报, 2022, 73(8): 3659-3668.

Figures/Tables 13

Fig.1 Synthesis of lubricating base oils by acenaphthene alkylation with 1-hexene / 1-octene catalyzed by ionic liquid

Fig.2 Gas chromatogram of the hexylacenaphthene (a) and octylacenaphthene (b)

Fig.3 Effect of different ratio of olefins to acenaphthene on product distribution

Table 1 Product distribution of hexylacenaphthene and octylacenaphthene

样品名称	烯烃/苊（摩尔比）	产物分布/%
样品名称	烯烃/苊（摩尔比）	单烷基苊	二烷基苊	三烷基苊	四烷基苊
己基苊-2	2/1	22.60	54.50	22.39	0.51
己基苊-3	3/1	3.55	31.48	58.37	6.59
辛基苊-2	2/1	25.08	46.27	28.00	0.64
辛基苊-3	3/1	7.17	38.10	50.51	4.22

Fig.4 FT-IR absorption spectra with acetonitrile probe of ionic liquid before and after reaction

Table 2 Physicochemical properties of alkylated acenaphthenes

产品名称	密度/ (g·cm^-3)	运动黏度/(mm²·s^-1)		黏度指数	苯胺点/℃	倾点/℃	闪点/℃	起始氧化温度/℃
产品名称	密度/ (g·cm^-3)	40℃	100℃	黏度指数	苯胺点/℃	倾点/℃	闪点/℃	起始氧化温度/℃
己基苊-2	0.9534	171.9	10.1	—	15.2	-18	201	192
己基苊-3	0.9343	349.6	15.4	—	34.5	-16	208	198
辛基苊-2	0.9372	190.5	12.5	24	38.5	-23	219	201
辛基苊-3	0.9186	331.6	19.5	52	62.4	-19	236	205

Fig.5 Contact angle of hexylacenaphthene-2 (a), hexylacenaphthene-3 (b), octylacenaphthene-2 (c) and octylacenaphthene-3 (d) on steel disc

Fig.6 Shear viscosity versus shear rate

Fig.7 Friction curves under the load of 100 N (a), 200 N (b) and 300 N (c) and average friction coefficient (d)

Fig.8 Wear volume of steel disc

Fig.9 3D images and profiles of wear scar of steel discs lubricated by N4010

Fig.10 3D images and profiles of wear scar of steel discs lubricated by hexylacenaphthene-2

Fig.11 3D images and profiles of wear scar of steel discs lubricated by hexylacenaphthene-3

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