This William Moore article from a 1935 edition of Fuel Oil Journal does a nice job of explaining how vacuum vents once worked on one-pipe steam systems.
The Improved Webster Type "R" System of Steam Heating is a service bulletin from Warren Webster and Company (The Pioneers of Vacuum Steam Heating), established in 1888.
This manual was created by O-E Specialty Manufacturing Co. and outlines how to install the "O-E" Perfect System, which is a Vapor Vacuum heating system.
Here is the original Installation and Operating Instructions and Parts List for The H.B. Smith Company's Oil Fired Cast Iron Hot Water Boilers (No. OHB-13W). This is esti...