I am not an expert, but I believe they were made in the 1800s and probably the 1880s.
Chesapeake And Ohio (C&O) Railroad Monkey Wrench Cast Iron RARE RAILROAD ANTIQUE
Norfolk And Western (N&W) Railroad Monkey Wrench All Metal RARE RAILROAD ANTIQUE
Antique L COES RAILROAD Monkey Wrench Worcester MA 1800's ~Wooden Handle ~
Antique Midwest central Monkey Wrench 15" Railroad Special MCRR
Antique Russwin 18” Monkey Wrench Wood Handles Railroad Wrench
ANTIQUE L. COES Med Under Loops Railroad Monkey Wrench Hammer Made in USA 12"L