Synthesis and applications of some new antioxidant and anticorrosive additives for Egyptian diesel motor oils

Pyrimidine‐5‐carboxylate derivative Ia was utilised as a key intermediate for the synthesis of new pyrimidine derivatives. Thiopyrimidine derivative Ia undergo N‐methylation using methyl iodide afforded III. Methylsulfanyl moiety in II was easily removed when reacted with phenyl hydrazine and thiosemicarbazide afforded pyrimidine derivatives IV and VI, respectively. The reaction on nitrogen atom in Ia using 1,3‐dibromo‐propane, benzoyl chloride, phosphorous oxychloride afforded VIII, IX and X, respectively. The reaction using 1,3‐dibromo‐propane or 1,2‐dibromo‐ethane furnished the formation of the corresponding fused cycles containing sulfur. Representative compounds of the synthesised products were evaluated as antioxidant and corrosion inhibitors for gasoline lube oils. Copyright © 2010 John Wiley & Sons, Ltd.

[1]  D. Jun-xiu,et al.  A tribological study of (2‐sulphurone‐benzothiazole)‐3‐methyl‐dibutyl borate , 2001 .

[2]  B. Ranu,et al.  Indium(III) chloride-catalyzed one-pot synthesis of dihydropyrimidinones by a three-component coupling of 1,3-dicarbonyl compounds, aldehydes, and urea: an improved procedure for the Biginelli reaction. , 2000, The Journal of organic chemistry.

[3]  Fenfang Li,et al.  The performance and antiwear mechanism of (2-sulfurone-benzothiazole)-3-methyl esters as additives in synthetic lubricant , 2000 .

[4]  Y. Wan,et al.  Tribological performance and action mechanism of S-alkyl and S-benzimidazole substituted dialkyldithiocarbamates , 2000 .

[5]  A. M. Khalil,et al.  Synthesis and testing of some new antioxidant and anticorrosion additives with potential for use in turbine aviation oils , 2000 .

[6]  Q. Xue,et al.  A study of 2-(dibutylaminomethyl)-thiobenzimidazole as an oil additive , 1999 .

[7]  Q. Xue,et al.  The effect of molecular structure of heterocyclic compounds containing N, O and S on their tribological performance , 1999 .

[8]  Q. Xue,et al.  The tribological behaviors of 2-mercaptobenzoxazole derivatives as additives in liquid paraffin , 1998 .

[9]  C. Kappe,et al.  Dipolar Cycloaddition Reactions of Dihydropyrimidine-Fused Mesomeric Betaines. An Approach toward Conformationally Restricted Dihydropyrimidine Derivatives(1). , 1997, The Journal of organic chemistry.

[10]  Q. Xue,et al.  Antiwear and extreme pressure characteristics of 2-mercaptobenzothiazole derivative as the potential lubricating oil additive , 1996 .

[11]  Q. Xue,et al.  The tribological properties of S-(1H-benzotriazol-1-YL) methyl alkyl xanthates as additives in synthetic lubricants{copyright} , 1995 .

[12]  A. Goel,et al.  5-Cyano-2-thiouracils and their derivatives: a new class of leishmanicides , 1994 .

[13]  X. Qun-ji,et al.  A study of S-(1H-benzotriazol-1-yl)methyl N,N-dialkyldithiocarbamates as novel multifunctional oil additives , 1994 .

[14]  C. Chandrasekharan,et al.  The effect of nitrogen and sulphur compounds on extreme pressure lubrication , 1993 .

[15]  V. Verma,et al.  A study of N, O and S heterocyclic compounds as extreme pressure lubricant additives , 1990 .

[16]  A. G. Gad Allah,et al.  Inhibition of corrosion of α-brass (Cu-Zn, 67/33) in acid chloride solutions by some amino pyrazole derivatives , 1989 .

[17]  A. Zeman,et al.  The DSC cell—a versatile tool to study thermal-oxidative degradation of lubricants and related problems , 1984 .

[18]  M. Wesołowski.  Thermal analysis of petroleum products , 1981 .

[19]  Huang Wei.  Tribological Properties of Benzothiazole Derivatives as Additives in Rapeseed Oil , 2003 .

[20]  V. Kuksa,et al.  Utilization of the amidoalkylation reaction in the synthesis of hydrogenated pyrimidine-2-thiones , 1997 .

[21]  A. Bhattacharya,et al.  E.P. activity assessment of certain nitrogen and sulphur heterocyclic compounds as potential additives in four ball test , 1990 .

[22]  C. Kappe,et al.  Synthesis and reactions of “biginelli‐compounds”. Part I , 1989 .

[23]  J. C. Bell,et al.  Laboratory screening of engine lubricants for high temperature performance , 1989 .

[24]  A. El‐Barbary,et al.  A one-step synthesis of 2-methylthio-6-oxopyrimidine derivatives: preparation of fused pyrimidinones , 1985 .