1,3,4-噻二唑席夫碱衍生物的合成及其摩擦性能
|
摘要
合成3种新型的1,3,4-噻二唑席夫碱衍生物,运用红外光谱与核磁共振波谱对合成的化合物进行结构表征。采用热重分析仪考察化合物的热稳定性,铜片腐蚀测定仪测试化合物在基础油液体石蜡中的抗腐蚀性能,用SRV微动摩擦磨损试验机评价其作为液体石蜡基础油添加剂的减摩抗磨性能,采用X射线光电子能谱仪(XPS)分析摩擦表面典型元素的化学状态,进而探讨其摩擦机理。结果表明,所合成的化合物具有良好的热稳定性能和抗腐蚀性能,能够有效提高润滑油的减摩抗磨性能,当添加质量分数为0.5%时,减摩抗磨效果最佳。在摩擦过程中,含添加剂的液体石蜡发生摩擦化学反应并生成由Fe_2O_3、Fe_3O_4、铁的硫化物和有机氮化物组成的混合边界润滑膜,从而产生润滑作用。
Three novel of 1,3,4-thiadiazole Schiff base derivatives were synthesized and characterized by IR and 1 H NMR.The thermal stability of these derivatives were tested by means of the thermo-gravimetric analysis(TGA),and their anti-corrosion properties in liquid paraffin base oil were investigated by copper strip corrosion tester.It was found that these thiadiazole Schiff base derivatives possessed satisfactory thermal stabilities and anti-corrosion properties.As the additive in liquid paraffin oil,the friction-reducing and anti-wear performances were evaluated on an SRV-IV oscillating reciprocating friction and wear tester.The result indicated that these synthetic additives were capable of drastically improving the friction-reducing and anti-wear properties,and the best performance was achieved when additive content increased to 0.5%.The element analysis of the worn surface were investigated by X-ray photoelectron spectroscopy(XPS),and the tribological mechanism was then discussed:the good tribological performance of liquid paraffin with additives was probably due to the formation of boundary lubrication films composed of Fe_2O_3,Fe_3O_4,iron sulfides,and certain organic nitrogen compounds by tribochemical reactions during the friction process.
Three novel of 1,3,4-thiadiazole Schiff base derivatives were synthesized and characterized by IR and 1 H NMR.The thermal stability of these derivatives were tested by means of the thermo-gravimetric analysis(TGA),and their anti-corrosion properties in liquid paraffin base oil were investigated by copper strip corrosion tester.It was found that these thiadiazole Schiff base derivatives possessed satisfactory thermal stabilities and anti-corrosion properties.As the additive in liquid paraffin oil,the friction-reducing and anti-wear performances were evaluated on an SRV-IV oscillating reciprocating friction and wear tester.The result indicated that these synthetic additives were capable of drastically improving the friction-reducing and anti-wear properties,and the best performance was achieved when additive content increased to 0.5%.The element analysis of the worn surface were investigated by X-ray photoelectron spectroscopy(XPS),and the tribological mechanism was then discussed:the good tribological performance of liquid paraffin with additives was probably due to the formation of boundary lubrication films composed of Fe_2O_3,Fe_3O_4,iron sulfides,and certain organic nitrogen compounds by tribochemical reactions during the friction process.
引文
[1]ZHU F,FAN W,WANG A,et al.Tribological study of novel S—N style 1,3,4-thiadiazole-2-thione derivatives in rapeseed oil[J].Wear,2009,266(1-2):233-238.
[2]XU X,WAN Y,CAO L.Tribological performance and action mechanism of S-alkyl and S-benzimidazole substituted dialkyldithiocarbamates[J].Wear,2000,241(1):41-46.
[3]王清华,胡泽祥,娄方,等.苯并咪唑的衍生物用作润滑油多功能添加剂的研究[J].石油炼制与化工,2001,32(11):37-39.(WANG Qinghua,HU Zexiang,LOU Fang,et al.Study on using benzimidazole derivatives as multifunctional additive for lubricant oils[J].Petroleum Processing and Petrochemicals,2001,32(11):37-39.)
[4]钱建华,张月,郑艳秋,等.新型双苯并咪唑润滑油添加剂的合成及其多效性能研究[J].石油化工,2011,40(12):1321-1324.(QIAN Jianhua,ZHANG Yue,ZHENG Yanqiu,et al.Synthesis and multiple-effect of bis-benzimidazole as lubricant additive[J].Petrochemical Technology,2011,40(12):1321-1324.)
[5]ZHAO G,ZHAO Q,WANG X,et al.A novel benztriazole derivative for enhancing the anti-oxidation properties of synthetic ester-based oils[J].Industrial Lubrication and Tribology,2014,66(3):353-359.
[6]XIONG L,QIAN L,QIU J,et al.Synthesis,tribological and hydrolysis stability study of novel benzotriazole borate derivative[J].Plos One,2014,9(1):83501-83509.
[7]CAI M,ZHOU F,LIU W,et al.Tribological properties of novel imidazolium ionic liquids bearing benzotriazole group as the antiwear/anticorrosion additive in poly(ethylene glycol)and polyurea grease for steel/steel contacts[J].ACS Applied Materials&Interfaces,2011,3(12):4580-4592.
[8]WU H,LI J,MA H,et al.Antiwear properties and tribochemical action mechanisms of three S-containing triazine derivatives as additives in rapeseed oil[J].Tribology Transactions,2009,52(3):277-283.
[9]ZENG X,LI J,WU X,et al.The tribological behaviors of hydroxyl-containing dithiocarbamate-triazine derivatives as additives in rapeseed oil[J].Tribology International,2007,40(3):560-566.
[10]HUANG W,HOU B,ZHANG P,et al.Tribological performance and action mechanism of S-[2-(acetamido)thiazol-1-yl]dialkyl dithiocarbamate as additive in rapeseed oil[J].Wear,2004,256(11-12):1106-1113.
[11]薛卫国,姚文钊,仇建伟,等.噻唑型杂环化合物作为润滑油添加剂的性能研究[J].石油商技,2008,26(1):156-158.(XUE Weiguo,YAO Wenzhao,QIU Jianwei,et al.A study on performance of thiazole heterocyclic derivatives as lubricant additives[J].Petroleum Products Application Research,2008,26(1):156-158.)
[12]KIM Y J,HOANG Q V,KIM S K,et al.Synthesis of poly(glycerol-succinic acid)dithiocarbam-ate and poly(glycerol-succinic acid)-1,3,4-thiadiazole dendrimers and their use as anti-wear oil additives[J].Bulletin of the Korean Chemical Society,2013,34(7):2044-2050.
[13]HIPLER F,FISCHER R A,MVLLER J.Matrix-isolation pyrolysis investigation ofmercapto-functionalized 1,3,4-thiadiazoles:thermal stability of thiadiazole lubricant additives[J].Physical Chemistry Chemical Physics,2005,7(5):731-737.
[14]LI Z,LI X,ZHANG Y,et al.Tribological study of a highly hydrolytically stable phenylboronic acid ester containing benzothiazolyl in mineral oil[J].Applied Surface Science,2014,308(30):91-99.
[15]LI J,LI Z,REN T,et al.Hydrolytic stability and tribological properties of N-containing heterocyclic borate esters as lubricant additives in rapeseed oil[J].Tribology International,2014,73(1):101-107.
[16]ZHAO X,YANG J,TAO D,et al.Tribological study of nitrogen plasma polymerized soybean oil with nitrogen heterocyclic structures[J].Industrial Crops and Products,2013,51(1):236-243.
[17]欧阳平,陈国需,李华峰,等.新型无硫磷含氮杂环化合物的制备及其摩擦学特性[J].摩擦学学报,2009,29(3):221-226.(OUYANG Ping,CHEN Guoxu,LI Huafeng,et al.New without sulfur phosphorus nitrogen heterocyclic compound preparation and its tribological properties[J].Tribology,2009,29(3):221-226.)
[18]CLERICI F,POCAR D,GUIDO M,et al.Synthesis of2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity[J].Journal of Medicinal Chemistry,2001,44(6):931-936.
[19]HOVSEPIAN T R,DILANIAN E R,ENGOYAN A P,et al.Synthesis of substituted 1,2,4-thiazoles and 1,3,4-thiadiazoles[J].Chemistry of Heterocyclic Compounds,2004,40(9):1194-1198.
[20]WANG J,WANG J,LIC,et al.A study of 2,5-dimercapto-1,3,4-thiadiazole derivatives as multifunctional additives in water-based hydraulic fluid[J].Industrial Lubrication and Tribology,2014,66(3):402-410.
[21]HU F,WEI X,ZONG Z,Study on tribological and corrosion inhibiting properties of thiadiazole derivative as lubricant grease additive[J].Industrial Lubrication and Tribology,2006,58(6):320-323.
[22]GAO Y,WU Z,ZHANG Z,et al.Study on tribological properties of 2,5-dialkoxymethylthio-1,3,4-thiadi-azoles[J].Wear,1998,222(2):129-134.
[23]CAI M,LIANG Y,ZHOU F,et al.A novel imidazolium salt with antioxidation and anticorrosion dual functionalities as the additive in poly(ethylene glycol)for steel/steel contacts[J].Wear,2013,306(1-2):197-208.
[24]任天辉,薛群基.含氮杂环化合物及其衍生物用作多功能滑油添加剂的研究发展现状[J].摩擦学学报,1994,14(4):370-381.(REN Tianhui,XUE Qunji.A survey on multifunctional oil additives of N-containing heterocyclic compounds and their derivatives[J].Tribology,1994,14(4):370-381.)
[25]路培中,张付特,曲黎,等.1,3,4-噻二唑-2-硫酮衍生物在菜籽油中的摩擦学性能研究[J].化学研究,2007,18(3):65-67.(LU Peizhong,ZHANG Fute,QU Li,et al.Tribological behavior of a 1,3,4-thiadiazole-2-thione derivative as an additive in rapeseed oil[J].Chemical Research,2007,18(3):65-67.)
[26]ZHANG J,LIU W,XUE Q,et al.A study of N and S heterocyclic compound as a potential lubricating oil additive[J].Wear,1999,224(1):160-164.
[27]CHEN H,YAN J,REN T,et al.Tribological behavior of some long-chain dimercaptothiadiazole derivatives as multifunctional lubricant additives in vegetable oil and investigation of their tribochemistry using XANES[J].Tribology Letters,2012,45(3):465-476.
[28]CHEN H,JIANG J,REN T,et al.Tribological behaviors of some novel dimercaptothiadiazole derivatives containing hydroxyl as multifunctional lubricant additives in biodegradable lithium grease[J].Industrial Lubrication and Tribology,2014,66(1):51-61.
[29]陈严华,欧阳平,张贤明,等.五元含氮杂环润滑添加剂的摩擦学研究进展[J].润滑与密封,2015,40(9):137-141.(CHEN Yanhua,OUYANG Ping,ZHANG Xianming,et al.Research and development in tribology of five-membered nitrogen-containing heterocyclic lubricating additives[J].Lubrication Engineering,2015,40(9):137-141.)
[30]吴华,任天辉,刘学傧,等.两种无灰无磷抗磨添加剂摩擦学性能及与ZDDP配伍性能研究[J].润滑油,2009,24(1):54-59.(WU Hua,REN Tianhui,LIU Xuebin,et al.Study on tribological behaviors of two ash-less and phosphorous-free anti-wear additives and their synergetic effects with ZDDP in 5 cSt[J].Lubricating Oil,2009,24(1):54-59.)
[31]GAO X,LI J,GAO W,et al.Tribological properties of steel and steel lubricated with a poly-α-olefin containing Schiff base copper complex[J].Journal of Tribology,2012,134(3):1-8.
[32]刘琼,龙军,武志强,等.摩擦改进剂烷基链特性对减摩性能的影响[J].石油学报(石油加工),2014,30(2):189-193.(LIU Qiong,LONG Jun,WU Zhiqiang,et al.Effect of alkyl chain characteristic of friction modifier on friction-reducing[J].Acta Petrolei Sinica(Petroleum Processing Section),2014,30(2):189-193.)
[2]XU X,WAN Y,CAO L.Tribological performance and action mechanism of S-alkyl and S-benzimidazole substituted dialkyldithiocarbamates[J].Wear,2000,241(1):41-46.
[3]王清华,胡泽祥,娄方,等.苯并咪唑的衍生物用作润滑油多功能添加剂的研究[J].石油炼制与化工,2001,32(11):37-39.(WANG Qinghua,HU Zexiang,LOU Fang,et al.Study on using benzimidazole derivatives as multifunctional additive for lubricant oils[J].Petroleum Processing and Petrochemicals,2001,32(11):37-39.)
[4]钱建华,张月,郑艳秋,等.新型双苯并咪唑润滑油添加剂的合成及其多效性能研究[J].石油化工,2011,40(12):1321-1324.(QIAN Jianhua,ZHANG Yue,ZHENG Yanqiu,et al.Synthesis and multiple-effect of bis-benzimidazole as lubricant additive[J].Petrochemical Technology,2011,40(12):1321-1324.)
[5]ZHAO G,ZHAO Q,WANG X,et al.A novel benztriazole derivative for enhancing the anti-oxidation properties of synthetic ester-based oils[J].Industrial Lubrication and Tribology,2014,66(3):353-359.
[6]XIONG L,QIAN L,QIU J,et al.Synthesis,tribological and hydrolysis stability study of novel benzotriazole borate derivative[J].Plos One,2014,9(1):83501-83509.
[7]CAI M,ZHOU F,LIU W,et al.Tribological properties of novel imidazolium ionic liquids bearing benzotriazole group as the antiwear/anticorrosion additive in poly(ethylene glycol)and polyurea grease for steel/steel contacts[J].ACS Applied Materials&Interfaces,2011,3(12):4580-4592.
[8]WU H,LI J,MA H,et al.Antiwear properties and tribochemical action mechanisms of three S-containing triazine derivatives as additives in rapeseed oil[J].Tribology Transactions,2009,52(3):277-283.
[9]ZENG X,LI J,WU X,et al.The tribological behaviors of hydroxyl-containing dithiocarbamate-triazine derivatives as additives in rapeseed oil[J].Tribology International,2007,40(3):560-566.
[10]HUANG W,HOU B,ZHANG P,et al.Tribological performance and action mechanism of S-[2-(acetamido)thiazol-1-yl]dialkyl dithiocarbamate as additive in rapeseed oil[J].Wear,2004,256(11-12):1106-1113.
[11]薛卫国,姚文钊,仇建伟,等.噻唑型杂环化合物作为润滑油添加剂的性能研究[J].石油商技,2008,26(1):156-158.(XUE Weiguo,YAO Wenzhao,QIU Jianwei,et al.A study on performance of thiazole heterocyclic derivatives as lubricant additives[J].Petroleum Products Application Research,2008,26(1):156-158.)
[12]KIM Y J,HOANG Q V,KIM S K,et al.Synthesis of poly(glycerol-succinic acid)dithiocarbam-ate and poly(glycerol-succinic acid)-1,3,4-thiadiazole dendrimers and their use as anti-wear oil additives[J].Bulletin of the Korean Chemical Society,2013,34(7):2044-2050.
[13]HIPLER F,FISCHER R A,MVLLER J.Matrix-isolation pyrolysis investigation ofmercapto-functionalized 1,3,4-thiadiazoles:thermal stability of thiadiazole lubricant additives[J].Physical Chemistry Chemical Physics,2005,7(5):731-737.
[14]LI Z,LI X,ZHANG Y,et al.Tribological study of a highly hydrolytically stable phenylboronic acid ester containing benzothiazolyl in mineral oil[J].Applied Surface Science,2014,308(30):91-99.
[15]LI J,LI Z,REN T,et al.Hydrolytic stability and tribological properties of N-containing heterocyclic borate esters as lubricant additives in rapeseed oil[J].Tribology International,2014,73(1):101-107.
[16]ZHAO X,YANG J,TAO D,et al.Tribological study of nitrogen plasma polymerized soybean oil with nitrogen heterocyclic structures[J].Industrial Crops and Products,2013,51(1):236-243.
[17]欧阳平,陈国需,李华峰,等.新型无硫磷含氮杂环化合物的制备及其摩擦学特性[J].摩擦学学报,2009,29(3):221-226.(OUYANG Ping,CHEN Guoxu,LI Huafeng,et al.New without sulfur phosphorus nitrogen heterocyclic compound preparation and its tribological properties[J].Tribology,2009,29(3):221-226.)
[18]CLERICI F,POCAR D,GUIDO M,et al.Synthesis of2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity[J].Journal of Medicinal Chemistry,2001,44(6):931-936.
[19]HOVSEPIAN T R,DILANIAN E R,ENGOYAN A P,et al.Synthesis of substituted 1,2,4-thiazoles and 1,3,4-thiadiazoles[J].Chemistry of Heterocyclic Compounds,2004,40(9):1194-1198.
[20]WANG J,WANG J,LIC,et al.A study of 2,5-dimercapto-1,3,4-thiadiazole derivatives as multifunctional additives in water-based hydraulic fluid[J].Industrial Lubrication and Tribology,2014,66(3):402-410.
[21]HU F,WEI X,ZONG Z,Study on tribological and corrosion inhibiting properties of thiadiazole derivative as lubricant grease additive[J].Industrial Lubrication and Tribology,2006,58(6):320-323.
[22]GAO Y,WU Z,ZHANG Z,et al.Study on tribological properties of 2,5-dialkoxymethylthio-1,3,4-thiadi-azoles[J].Wear,1998,222(2):129-134.
[23]CAI M,LIANG Y,ZHOU F,et al.A novel imidazolium salt with antioxidation and anticorrosion dual functionalities as the additive in poly(ethylene glycol)for steel/steel contacts[J].Wear,2013,306(1-2):197-208.
[24]任天辉,薛群基.含氮杂环化合物及其衍生物用作多功能滑油添加剂的研究发展现状[J].摩擦学学报,1994,14(4):370-381.(REN Tianhui,XUE Qunji.A survey on multifunctional oil additives of N-containing heterocyclic compounds and their derivatives[J].Tribology,1994,14(4):370-381.)
[25]路培中,张付特,曲黎,等.1,3,4-噻二唑-2-硫酮衍生物在菜籽油中的摩擦学性能研究[J].化学研究,2007,18(3):65-67.(LU Peizhong,ZHANG Fute,QU Li,et al.Tribological behavior of a 1,3,4-thiadiazole-2-thione derivative as an additive in rapeseed oil[J].Chemical Research,2007,18(3):65-67.)
[26]ZHANG J,LIU W,XUE Q,et al.A study of N and S heterocyclic compound as a potential lubricating oil additive[J].Wear,1999,224(1):160-164.
[27]CHEN H,YAN J,REN T,et al.Tribological behavior of some long-chain dimercaptothiadiazole derivatives as multifunctional lubricant additives in vegetable oil and investigation of their tribochemistry using XANES[J].Tribology Letters,2012,45(3):465-476.
[28]CHEN H,JIANG J,REN T,et al.Tribological behaviors of some novel dimercaptothiadiazole derivatives containing hydroxyl as multifunctional lubricant additives in biodegradable lithium grease[J].Industrial Lubrication and Tribology,2014,66(1):51-61.
[29]陈严华,欧阳平,张贤明,等.五元含氮杂环润滑添加剂的摩擦学研究进展[J].润滑与密封,2015,40(9):137-141.(CHEN Yanhua,OUYANG Ping,ZHANG Xianming,et al.Research and development in tribology of five-membered nitrogen-containing heterocyclic lubricating additives[J].Lubrication Engineering,2015,40(9):137-141.)
[30]吴华,任天辉,刘学傧,等.两种无灰无磷抗磨添加剂摩擦学性能及与ZDDP配伍性能研究[J].润滑油,2009,24(1):54-59.(WU Hua,REN Tianhui,LIU Xuebin,et al.Study on tribological behaviors of two ash-less and phosphorous-free anti-wear additives and their synergetic effects with ZDDP in 5 cSt[J].Lubricating Oil,2009,24(1):54-59.)
[31]GAO X,LI J,GAO W,et al.Tribological properties of steel and steel lubricated with a poly-α-olefin containing Schiff base copper complex[J].Journal of Tribology,2012,134(3):1-8.
[32]刘琼,龙军,武志强,等.摩擦改进剂烷基链特性对减摩性能的影响[J].石油学报(石油加工),2014,30(2):189-193.(LIU Qiong,LONG Jun,WU Zhiqiang,et al.Effect of alkyl chain characteristic of friction modifier on friction-reducing[J].Acta Petrolei Sinica(Petroleum Processing Section),2014,30(2):189-193.)