Summary
-
1.
Debromination methyl linoleate has been polymerized at 290° and 300° for varying periods, and analysis has been made for monomer, dimer, trimer, normal, and conjugated linoleate.
-
2.
The disappearance of normal linoleate follows a first order reaction rate with values of K=0.10 hr.−1 at 300° and 0.05 hr.−1 at 290°.
-
3.
Polymerization of mixtures of normal and conjugated linoleate indicate that dimer may be formed by their reaction with each other.
-
4.
The value for K, the first order reaction velocity constant for disappearance of normal linoleate, decreases to a limiting value on dilution with methyl stearate. This limiting value is about one-fourth that obtained on undiluted linoleate.
-
5.
The above facts are qualitatively explained by assuming that the mechanism of dimerization of normal linoleate is extensively: N»C relatively slow N+C→D relatively rapid.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Kino, Sci. Papers Inst. phys. chem. res. (Tokyo)15, 127–9, 130–136 (1931);16, 127–32, 133–5 (1931);18, 77–82 (1932);20 103–8 (1933);21, 63–8 (1933);24, 25–32, 218–25 (1934);26, 91–7 (1935);28, 140–5 (1935),29, 31–6 (1936).
Kappelmeier, Faben-Ztg.38, 1018–20, 1077–9 (1933).
Steger and van Loon, Rec. trav. chim.53, 769–78 (1934).
Brod, France, and Evans, Ind. Eng. Chem.,32, 114–8 (1939).
Bradley and Johnston, Ind. Eng. Chem.32, 802–9 (1940).
Bradley and Johnston, Ind. Eng. Chem.33, 86–9 (1941).
Bradley and Richardson, Ind. Eng. Chem.32, 963–9 (1940).
Scheiber, Farbe u. Lacke1929, 585–7,1936, 315–6, 329–30, 341 351–2, Felte u Seifen43, 103–5 (1936).
Kappelmeier, Farben. Ztg.38, 1018–20, 1077–9, 1933).
Ahmad and Farmer, J. Chem. Soc.1940, 1176–8.
Lawson and Spoerri, Paint, Oil & Chem. Rev.110 (6) 13–16 (1947).
Kass in “Protective and Decorative Coatings,” Vol. IV Ch. 12, 1944, J. J. Matiello, John Wiley & Sons Inc., N. Y.
Mitchell, Kraybill, and Zscheille, Ind. Eng. Chem. Anal. Ed.15, 1–3 (1943).
Cowan, Falkenburg, and Teeter, Ind. Eng. Chem. Anal. Ed.16, 90–2 (1944).
Terry and Wheeler, Oil and Soap23, 88–90 (1946).
S. S. Glasstone, Text Book of Physical Chemistry, D. Van Nostrand Co., N. Y., p. 1047.
Anderson and Porter, paper presented at Symposium on Drying Oils, University of Minnesota, March, 1947.
Author information
Authors and Affiliations
Additional information
Member of the New York Bar; member of law firm of Davis and Gilbert, New York, N. Y.
About this article
Cite this article
Paschke, R.F., Wheeler, D.H. Thermal polymerization of unsaturated fatty esters normal methyl linoleate. J Am Oil Chem Soc 26, 278–283 (1949). https://doi.org/10.1007/BF02651484
Issue Date:
DOI: https://doi.org/10.1007/BF02651484