Abstract
Acrylate esters of various hydroxy acid derivatives obtainable from castor oil have been synthesized and characterized. Synthetic methods evaluated include acid- and base-catalyzed alcoholysis of methyl acrylate, esterification with acrylic acid, acrylyl chloride, or acrylic anhydride, and esterification with β-chloropropionyl chloride or anhydride followed by dehydrohalogenation. The two-step esterification-dehydrohalogenation procedure gives most satisfactory yields and purity. Preparation, purification, and characterization of the compounds are described and the various synthetic methods are evaluated.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
For a comprehensive review, see Clarke, J. T. in “Monomers,” edited by E. R. Blout, W. P. Hohenstein and H. Mark, Interscience Publishers, New York, 1951.
(a) Lynn, J. W. (Union Carbide Corp.) U.S. 3,010,925 (1961); (b) CIBA, Ltd., Swiss 261,121 (1949); (c) CIBA, Ltd., Swiss 265,396–265,401 (1950); Medalia, A. I. U.S. 2,868, 755 (1959).
Applewhite, T. H., J. S. Nelson and L. A. Goldblatt, JAOCS40, 101–104 (1963).
Applewhite, T. H., and J. S. Nelson, manuscript in preparation.
Applewhite, T. H., M. J. Diamond and L. A. Goldblatt, JAOCS38, 609–614 (1961).
Stempel, G. H., Jr., R. P. Cross and R. P. Mariella, J. Am. Chem. Soc.72, 2299–2300 (1950).
Nelson, J. S., L. A. Goldblatt and T. H. Applewhite, J. Org. Chem.28, 1905–1907 (1963).
Swern, D., and E. F. Jordan, Jr., Biochem. Preparations2, 104–105 (1952).
Straus, F., H. Heinze and L. Salzmann, Chem. Ber.66, 631–639 (1933).
Binder, R. G., T. H. Applewhite, G. O. Kohler and L. A. Goldblatt, JAOCS39, 513–517 (1962).
Rehberg, C. E., Org. Syn.26, 18–21 (1946).
Diamond, M. J., T. H. Applewhite, R. E. Knowles and L. A. Goldblatt, JAOCS41, 9–13 (1964).
Mattson, F. H., R. A. Volpenhein and J. B. Martin, J. Lipid Res.5, 374–377 (1964).
Tipson, R. S., J. Org. Chem.9, 235–241 (1944).
Tachibana, T., and H. Kambara, J. Am. Chem. Soc.87, 3015–3016 (1965).
Leduc, P., and P. Chabrier, Bull. Soc. Chim. France1963, 2271–2276 (1963).
See also Hickmott, P. W., J. Chem. Soc.1964, 883–887 (1964).
Marvel, C. S., and R. L. Frank, J. Am. Chem. Soc.64, 1675–1678 (1942).
Hall, H. K., Jr., J. Am. Chem. Soc.78, 2717–2719 (1956).
Coppinger, G. M., J. Am. Chem. Soc.76, 1372–1373 (1954).
Author information
Authors and Affiliations
Additional information
W. Utiliz. Res. Dev. Div., ARS, USDA.
About this article
Cite this article
Nelson, J.S., Applewhite, T.H. Castor-based derivatives: Synthesis of some acrylate esters. J Am Oil Chem Soc 43, 542–545 (1966). https://doi.org/10.1007/BF02679869
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02679869