Efficient Esterification of Long Chain Aliphatic Carboxylic Acids with Alcohols over ZrOCl2·8H2O Catalyst

Kshudiram Mantri; Kenichi Komura; Yoshihiro Sugi

doi:10.1055/s-2005-869951

PAPER

Efficient Esterification of Long Chain Aliphatic Carboxylic Acids with Alcohols over ZrOCl₂·8H₂O Catalyst

Kshudiram Mantri, Kenichi Komura, Yoshihiro Sugi*
Department of Materials Science and Technology, Faculty of Engineering, Gifu University, Yanagido, 1-1, Gifu 501-1193, Japan
Fax: +81(58)2932597; e-Mail: sugi@apchem.gifu-u.ac.jp;

Abstract

Alle Artikel dieser Rubrik

Abstract

Direct condensation of equimolar amounts of long chain carboxylic acids and alcohols could be achieved by using zirconyl chloride as an efficient catalyst. ZrOCl₂·8H₂O showed high activity for esterification between primary acids and alcohols; however, it was less active in the combination of branched acid and secondary alcohols to give the corresponding esters.

Key words

esterification - long chain aliphatic carboxylic acid - long chain aliphatic alcohol - zirconyl chloride

Volltext

Referenzen

References

1 Larock RC. Comprehensive Organic Transformations VCH; New York: 1989. p.966

2 Otera J. Esterification: Methods, Reactions and Applications Wiley-VCH; Weinheim: 2003. p.303

3 The Chemistry of Carboxylic Acid and Esters Patai S. Wiley; New York: 1969.

4a Olah GA. Keumi T. Meidar D. Synthesis 1978, 929

4b Masaki Y. Tanaka N. Miura T. Chem. Lett. 1997, 55

4c Kadaba PK. Synthesis 1972, 628

4d Lawrance WW. Tetrahedron Lett. 1971, 3453

4e Nakao R. Oka K. Fukumoto T. Bull. Chem. Soc. Jpn. 1981, 54: 1267

4f Kumar AK. Chottopadhyay TK. Tetrahedron Lett. 1987, 28: 3713

5 Rama S. Lingaiah N. Devi BLAP. Prasad RBN. Suryanarayana I. Sai Prasad PS. Appl. Catal., A 2004, 276: 163

6 Kawabata T. Mizugaki T. Ebitani K. Kaneda K. Tetrahedron Lett. 2003, 44: 9205

7 Saroja M. Kaimol TNB. Synth. Commun. 1986, 11: 1423

8a Ishihara K. Ohara S. Yamamoto H. Science 2000, 290: 1140

8b Ishihara K. Nakayama M. Ohara S. Yamamoto H. Synlett 2001, 1117

8c Ishihara K. Nakayama M. Ohara S. Yamamoto H. Tetrahedron 2002, 58: 8179

8d Nakayama M. Sato A. Ishihara K. Yamamoto H. Adv. Synth. Catal. 2004, 346: 1275

9 Bartoli G. Boeglin J. Bosco M. Locatelli M. Massaccesi M. Melchiorre P. Sambri L. Adv. Synth. Catal. 2005, 347: 33

10a Kantam ML. Bhaskar V. Choundary BM. Catal. Lett. 2002, 78: 185

10b Wakasugi K. Misaki T. Yamada K. Tanabe Y. Tetrahedron Lett. 2000, 41: 5249

10c Manabe K. Iimura S. Sun X.-M. Kobayashi S. J. Am. Chem. Soc. 2002, 124: 11971

10d Hao X. Yoshida A. Nishikido J. Tetrahedron Lett. 2004, 45: 781

10e Wakasugi K. Nakamura A. Iida A. Nishii Y. Nakatani N. Fukushima S. Tanabe Y. Tetrahedron 2003, 59: 5337

10f Oohashi Y. Fukumoto K. Mukaiyama T. Chem. Lett. 2004, 968