O Pegs Double Bond - C&EN Global Enterprise (ACS Publications)

Nov 6, 2010 - Ozone may replace bromine as the analytical tool for determining olefinic unsaturation. That's the opinion of A. Maggiolo, director of o...
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0 3 Pegs Double Bond Ozone may replace bromine as the analytical tool for determining olefinic imsaturation. That's the opinion of A. Maggiolo, director of organic re­ search and development at the Welsbach Foundation, Philadelphia. H e , S. Knesbach, and A. Tumolo have devel­ oped an analytical technique which measures imsaturation in mono- as well as polyunsaturates, whether the double bond is conjugated or not. In 1951, Boer and Kooyman dis­ covered that a constant stream of ozone is an excellent titrimetric reagent for the double bond. But the procedure they developed was too elaborate and time consuming, Maggiolo says; five hours were required for one determina­ tion. The older method involves using dyes which react with ozone giving a color change to show the endpoint. T h e new method eliminates the elaborate equipment that Boer and

Kooyman used. Maggiolo uses readily available commercial apparatus—a gasliquid reactor and an ozone meter. First, a weighed sample of olefin is cooled to —10° C. in a dry ice-alcohol bath. The researchers find that at this temperature they get a sharp end point of ozone absorption—at higher tempera­ tures, t h e products of ozonolysis, carbonyl compounds, react with the ozone. Then, ozone is passed into the reaction vessel, and the contents are stirred at about 1200 to 1500 r.p.m. At the end point, a sharp deflection of the meter's indicating needle shows the marked increase in unabsorbed ozone. The researchers express results as imsaturation equivalents—number of grams of material containing one double bond. They prefer this term to "ozone number," which they say has no chemi­ cal significance. One advantage of this method over bromination: The pres­ ence of tertiary hydrogens does not cause high varying results.

Ozone DeterminesUnsaturationQuantitatively

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Carl Schleicher & Schuell Co. Keene. New Hampshire

OCT.

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1958

Dept, C-58

C8EN

41

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