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1,2-Cycloaddition of Haloalkenes to Conjugated Fatty Esters

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Journal of the American Oil Chemists’ Society

Abstract

We have studied the reaction of 1,1-dichloro-2,2-difluoro-, chlorotrifluoro-, and tetrafluoro-ethylenes and also hexafluoropropylene withcis,trans andtrans,trans isomers of conjugated methyl octadecadienoate. Reactions gave 50-82% yields of cycloaddition products. The pre-ponderance of products with a cyclobutane struc-ture and a double bonda,β to the cyclobutane ring was shown by IR and NMR spectra.

Reactions were carried out in diluent with hy-droquinone inhibitor at autogenous pressure and a temperature of 200C for 5 hr. The distilled adducts are colorless liquids with viscosities rang-ing from 11 to 19 centistokes at 100F. These products and their hydrogenated derivatives ex-hibit low pour points (down to -76F) and may be useful as low-temperature plasticizers or lubricant additives.

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References

  1. Bartlett, P. D., L. K. Montgomery and B. Scidel, J. Am. Chem. Soc.86, 616–622 (1964).

    Article  CAS  Google Scholar 

  2. Coffman, D. D., P. L. Barrick, R. D. Cramer and M. S. Raasch, —Ibid.71, 490–496 (1949).

    Article  CAS  Google Scholar 

  3. Danzig, M. J., J. L O’Donnell, E. W. Bell, J. C. Cowan and H. M. Tetter, JAOCS34, 136–138 (1957).

    Article  CAS  Google Scholar 

  4. Friedrich, J. P., E. W. Bell and R. E. Beal, —Ibid.39, 420 (1962).

    Article  CAS  Google Scholar 

  5. Friedrich, J. P., E. W. Bell and L. E. Gast, —Ibid.42, 643–645 (1965).

    Article  CAS  Google Scholar 

  6. Montgomery, L. K., K. Schueller and P. D. Bartlett, J. Am. Chem. Soc.86, 622–628 (1964).

    Article  CAS  Google Scholar 

  7. Roberts, J. D., and C. M. Shants, Org. Reactions12, 1–56 (1962).

    CAS  Google Scholar 

  8. Schneider, W. J., L. E. Gast and H. M. Teeter, JAOCS41, 605–606 (1964).

    Article  Google Scholar 

  9. Trutnorsky, H., Mikrochlm. Acta1963, 499.

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Authors and Affiliations

  1. Northern Regional Research Laboratory, 61604, Peoria, Illinois

    E. W. Bell, J. P. Friedrich, L. E. Gast & J. C. Cowan

Authors
  1. E. W. Bell
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  2. J. P. Friedrich
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  3. L. E. Gast
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  4. J. C. Cowan
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Additional information

N. Utiliz. Ees. and Dev. Div., ARS, USDA.

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Bell, E.W., Friedrich, J.P., Gast, L.E. et al. 1,2-Cycloaddition of Haloalkenes to Conjugated Fatty Esters. J Am Oil Chem Soc 45, 388–392 (1968). https://doi.org/10.1007/BF02667117

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  • DOI: https://doi.org/10.1007/BF02667117

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