Patented Oct. 26, 1926.

1,604,472

UNITED STATES PATENT OFFICE.

DoNALD ARCHER NIGHTING-ALE, OF AMBLER, PENNSYLVANIA, ASSIGNOR TO THE
KETOID COMPANY, OF WILMINGTON, DELAWARE, A CORPORATION OF DELAWARE.
METHOD OF MAKING ACETYL SALICYLIC ACID.
NoDrawing. Application filed July 22, 1924, Serial No. 727,488. Renewed March 18, 1926.
My invention relates to the manufacture salicylic acid is dissolved in about five times
of the mono acetic acid ester of salicylic its weight of dry ethyl ether. Keten
acid. (CHO) is passed through the solution to
This substance, more usually known as the point of saturation. On evaporation of
5 acetyl salicylic acid (and to trade as as the ether there remains a mass of needle
pirin) is commonly prepared from salicylic like crystals of acetyl salicylic acid.
acid, acetic acid and acetic anhydride. The The reaction that takes place may be rep 35
process is somewhat tedious in that it in resented by the following equation:
volves fractional crystallization, with its at CHO-H-CHO=CHO,
10 tendant losses.
The object of my invention is to provide a Having now described my invention, what
cheaper and more rapid method of me nufac I claim as new and desire to secure by Let 4)
turing acetyl-salicylic acid of a high degree ters Patent, is:
of purity, with a practically quantitative 1. The method of manufacturing acetyl
15 yield. salicylic acid which comprises reacting upon
My invention is based on my discover salicylic acid with keten.
that keten when brought in contact wit 2. The method of manufacturing acetyl 45
salicylic acid will effect a rapid esterification Salicylic acid which comprises reacting upon
of the salicylic acid by direct addition and salicylic acid with keten in the presence of
20 therefore without the formation of water a neutral solvent which is also a solvent of
of decomposition, which is a drawback to keten.
the old method, and my invention consists 3. The method of manufacturing acetyl
broadly speaking in the method of manufac salicylic acid which consists in dissolving
turing acetyl salicylic acid by bringing keten salicylic acid in a neutral solvent which is
25 into contact with salicylic acid. also a solvent of keten and passing keten gas
The time required for this reaction is cont through the solution.
siderably shortened by the use of a mutual DONALD A. NIGHTINGALE.
solvent. For example: A given quantity of