Op and Maint manual (Form 33489-3, 99E1 and up) calls for 26 quarts of 30 wt in the tranny, also there's a filter just to the side and a little further to the rear of the park brake drum. Cat may have changed the specs for oil in later critters (mine is a 1960 model 99 E 1035) so someone else may chip in with updated info on this.
Happen to have the service manual open for a little later model (1970's) and everything gear and drive train used SAE 90 gear oil except the steering gear housing used SAE 30 lube oil and hydraulics was SAE 10W.
I expect yours would be the same.
Current lube designations have all changed now and here is a viscosity chart to help compare.