4 methylbenzenethiol

Example 3

A C20 uPAO dimer was alkylated with 4-methylbenzenethiol (obtained from Sigma-Aldrich) by acid catalyst as shown below in Scheme 2 to form Product II containing Compound-III and Compound-IV.

[Figure (not displayed)]

A glass reactor under N₂ atmosphere was charged with C20 uPAO dimer (1001.12 g, 3.57 mol), 4-methylbenzenethiol (500.10 g, 4.02 mol) (obtained from Sigma-Aldrich), and Amberlyst 15-H (20.0 g, 1.31 wt %) (obtained from Sigma-Aldrich) to form a mixture. The mixture was heated with stirring at 120° C. for 3 days. The reaction mixture was filtered through Celite to remove catalyst. The filtrate was distilled under vacuum to 140° C. to remove unreacted thiol and then to 215° C. to remove unreacted olefin. The distillation pot bottoms were treated with decolorizing carbon (20 g) and filtered through Celite. The filtrate was collected as Product II containing Compound-III and Compound-IV. The lube properties of Product II were determined as provided above and are shown below in TABLE VI.

Example 1

A C16 uPAO dimer was alkylated with 4-methylbenzenethiol by acid catalyst as shown below in Scheme 1 to form Product I containing Compound-I and Compound-II.

[Figure (not displayed)]

A glass reactor under N₂ atmosphere was charged with C16 uPAO dimer (242.1 g, 1.07 mol), 4-methylbenzenethiol (160.4 g, 1.29 mol) (obtained from Sigma-Aldrich), and Amberlyst-15H (6.89 g, 1.7 wt %) (obtained from Sigma-Aldrich) to form a mixture. The mixture was heated with stirring at 120° C. for 20 hours. The mixture was filtered to remove catalyst. The filtrate was distilled under vacuum to 160° C.-205° C. to remove unreacted olefin and thiol. The distillation pot bottoms were collected as Product I containing Compound-I and Compound-II in a molar ratio of approximately 97.5 to 2.5. The lube properties of Product I were determined as provided above and are shown below in TABLE IV.