Synthesis of New Sulfur-free and Phosphorus-free Ether-ester and Study on Its Properties As Ashless Friction Modifier

doi:10.6023/A23030101

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (5): 461-468.DOI: 10.6023/A23030101 Previous Articles Next Articles

Article

新型无硫无磷醚-酯化合物的合成及其作为无灰摩擦改进剂的性能研究

王俊^a^,^b, 许晓梅^b^,^c, 周姣龙^b, 赵雅男^b, 孙秀丽^b, 唐勇^b, 何素芳^*^,^a(), 杨红梅^b^,^*()

a 昆明理工大学材料科学与工程学院云南昆明 650093
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 上海理工大学材料与化学学院上海 200093

投稿日期:2023-03-30 发布日期:2023-05-08
基金资助:
受云南“万人计划”青年拔尖人才专项(YNWR-QNBJ-2018-067); 受云南“万人计划”青年拔尖人才专项(YNWR-QNBJ-2020-002); 中核集团领创科研项目和中国科学院战略性先导科技专项(A类)“变革性洁净能源关键技术与示范”(XDA21021203)

Synthesis of New Sulfur-free and Phosphorus-free Ether-ester and Study on Its Properties As Ashless Friction Modifier

Jun Wang^a^,^b, Xiaomei Xu^b^,^c, Jiaolong Zhou^b, Yanan Zhao^b, Xiuli Sun^b, Yong Tang^b, Sufang He^a(), Hongmei Yang^b()

a Faculty of Materials Science and Engineering, Kunming University of Science and Technology, Kunming 650093, Yunnan, China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
c School of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, China

Received:2023-03-30 Published:2023-05-08
Contact: *E-mail: shucai1983@163.com; yanghm@sioc.ac.cn
Supported by:
Yunnan Ten Thousand Talents Plan Young & Elite Talents Project(YNWR-QNBJ-2018-067); Yunnan Ten Thousand Talents Plan Young & Elite Talents Project(YNWR-QNBJ-2020-002); LingChuang Research Project of China National Nuclear Corporation and Strategic Pilot Science and Technology Special Project of the Chinese Academy of Sciences (Class A) “Key Technologies and Demonstration of Transformative Clean Energy”(XDA21021203)

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Abstract

With the upgrading of mechanical equipment and the implementation of the “double-carbon” policy, the demand for high-quality lubricants with longer drain period, more clean and environmental friendly is increasing day by day. The study on new additives and base oils, as well as the compatibility law between the two has always run through the development of high-performance lubricants. As an important additive to improve the durability of lubricating protection and fuel economy, the design and development of friction modifier is the forefront of the development of lubrication technologies. Based on these, a new sulfur-free and phosphorus-free ether-ester DOA-mPEG350 was designed and synthesized, and characterized by nuclear magnetic resonance (NMR), high resolution mass spectrometer (HR-MS), Fourier transform infrared (FT-IR) and gel permeation chromatography (GPC). Meanwhile, the thermal stability of DOA-mPEG350 and its compatibility with synthetic hydrocarbon base oil were analyzed by thermogravimetric analysis (TGA) and ultraviolet visible spectroscopy (UV-Vis). The tribological behaviors of DOA-mPEG350 as an ashless friction modifier in synthetic hydrocarbons were studied using a four-ball friction and wear tester. The results show that DOA-mPEG350 has good thermal stability and compatibility with synthetic hydrocarbon base oil, and can effectively shorten the running-in period, and 1.0% (w) addition of DOA-mPEG350 could decrease the ave. coefficient of friction (COF) and wear scar diameter (WSD) of synthetic hydrocarbons such as CTL6 and PAO6 base oils by 20.6%, 20.1% and 28.9%, 34.8%, respectively. The comprehensive friction reduc ing and anti-wear performance of DOA-mPEG350 is better than that of the selected commercial friction modifier and extreme pressure anti-wear additives, which are usually contain sulfur, phosphorus, or metals that can not meet the increasingly stringent environmental requirements, that is, the synthesized DOA-mPEG350 has the potential to replace these additives. Through analyzing the worn friction surface and density functional theory (DFT) calculation, the micro-lubrication mechanism of ether-ester is revealed, namely, it can combine the “line contact” of ether with the “point contact” of ester to form a thick and dense protective film on metal surfaces, thus showing better tribological performance than that only contain ether chain or ester group.

Key words: sulfur-free and phosphorus-free, ether-ester, synthesis, ashless friction modifier, lubricating mechanism

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Jun Wang, Xiaomei Xu, Jiaolong Zhou, Yanan Zhao, Xiuli Sun, Yong Tang, Sufang He, Hongmei Yang. Synthesis of New Sulfur-free and Phosphorus-free Ether-ester and Study on Its Properties As Ashless Friction Modifier[J]. Acta Chimica Sinica, 2023, 81(5): 461-468.

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Fig. & Tab. 11

Figure 1. UV-Vis analysis of DOA-mPEG350 in CTL 6: (a) UV-Vis spectrum of 0.5% (w) addition; (b) absorbance of different additions at 227 nm (Inset is the linear fitting of absorbance of 0.5%~5.0% (w) additions)

Residual mass/%	130 ℃	250 ℃	350 ℃	400 ℃
IPG	1.5	1.4	1.4	1.4
IPG-OTs	97.4	45.9	18.8	17.9
IPG-mPEG350	95.8	76.4	1.3	0.8
DOA-mPEG350	99.1	96.2	84.0	34.5

Table 1. Thermo-stability analysis of DOA-mPEG350

Figure 2. (a) Friction profiles and (b) friction reducing and anti-wear properties with an increasing additions of DOA-mPEG350

Figure 3. The performance comparison of ether-ester with the ether and ester additives: (a) friction profiles; (b) friction reducing and anti-wear properties

Figure 4. (a) Ave. COF and (b) ave. WSD of 1.0% (w) of different additives in the synthetic hydrocarbon base oils

Figure 5. Micro-IR analysis of the oil with 1.0% (w) DOA-mPEG350 after tribological test

Figure 6. EDS analysis of CTL6 base oil and the oil with 1.0% (w) DOA-mPEG350 after tribological test

Figure 7. XPS spectra after peak fitting: (a) C1s; (b) O1s

Figure 8. Theoretical calculation of the electrostatic potential (ESP) of (a) IPG-mPEG350, (b) DOA-mPEG350 and (c) Triolein

Figure 9. Possible arrangement of different structures on metal surfaces

Scheme 1. The synthetic route of 1,2-dioleate-3-mPEG350 glycerides

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新型无硫无磷醚-酯化合物的合成及其作为无灰摩擦改进剂的性能研究

Synthesis of New Sulfur-free and Phosphorus-free Ether-ester and Study on Its Properties As Ashless Friction Modifier

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