Kinetics and mechanism of the reaction between maleic anhydride and fatty acid esters and the structure of the products

European Journal of Lipid Science and Technology

Volumn 110, Issue 5, 2008, Pages 441-447

  Stefanoiu, Florina ^a   Candy, Laure ^a   Vaca Garcia, Carlos ^a   Borredon, Elisabeth ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

Activation energy; Alkenyl succinic anhydride; Ene reaction; Maleinization; Reaction order

Indexed keywords

HELIANTHUS;

EID: 54549119165     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.200700181     Document Type: Article

References (19)

1. L. Neimo: Internal sizing of paper. In: Papermaking Science and Technology. Fapet Oy Helsinki, Helsinki (Finland) 1999, pp. 151-203.
2. W. E. Scott: Sizing with synthetic sizing materials. In: Principles of Wet End Chemistry. Tappi, Tappi Press, Atlanta (USA) 1996, pp. 99-110.
3. M. Morard, C. Vaca-Garcia, M. Stevens, J. Van Acker, O. Pignolet, E. Borredon: Durability improvement of wood by treatment with methyl alkenoate succinic anhydrides (M-ASA) of vegetable origin. Int Biodeterior Biodegradation 2007, 59, 103-110.
4. W. F. Williamson, P. S. Landis, B. N. Rhodes: WO 9 961 563 (1999).
5. H. Warth, R. Mulhaupt, B. Hoffmann, S. Lawson: Polyester networks based upon epoxidized and maleinated natural oils. Angew Makromol Chem. 1997, 249, 79-92.
6. W. G. Bickford, P. Krauczunas, D. H. Wheeler: The reaction of nonconjugated unsatured fatty esters with maleic anhydride. Oil Soap. 1942, 23-27.
7. H. M. Teeter, M. J. Geerts, J. C. Cowan: Polymerization of drying oils. III. Some observations on reaction of maleic anhydride with methyl oleate and methyl linoleate. J Am Oil Chem Soc. 1948, 158-162.
8. H. Plimmer: The reaction of maleic anhydride with nonconjugated unsaturated fatty materials. J Oil Colour Chem Assoc. 1949, 32, 99-112.
9. O. B. Wurzburg: US 3 102 064 (1963).
10. P. G. Irwin, V. Selwitz, C. M. Selwitz: US 3 412 111 (1968).
11. P. Maekipeura, M. Kapanen, J. Tulisalo, S. Kpskimies: WO 9 723 474 (1997).
12. D. Binet, P. Gateau, J. P. Durand: US 5 739 355 (1998).
13. K. Holmberg, J. A. Johansson: Addition of maleic anhydride to esters of mono-unsaturated fatty acid. Acta Chem Scand. 1982, B36, 481-485.
14. J. O. Metzger, K. F. Leisinger: Die En-Reaktion und ihre Anwendung auf ungesättigte Fettstoffe. Fat Sci Technol. 1988, 90, 1-5.
15. F. R. Benn, J. Dwyer, L. Chappell: The ene reaction of maleic anhydride with alkenes. J Chem Soc. 1977, 533-535.
16. S. H. Nahm, H. N. Cheng: Transition state geometry and stereochemistry of the ene reaction between olefins and maleic anhydride. J Org Chem. 1986, 51, 5093-5100.
17. J. O. Metzger, U. Biermann: Produkte der thermischen En-Reaktion von ungesättigen Fettstoffen und Maleinsäureanhydrid. Fat Sci Technol. 1994, 96, 321-323.
18. J. Quesada: Production of alkenyl succinic anhydrides from low-erucic and low-linolenic rapeseed oil methyl esters. Eur J Lipid Sci Technol. 2003, 105, 281-287.
19. J. Quesada, M. Morard, C. Vaca-Garcia, E. Borredon: Preparation of alkenyl succinic anhydrides from vegetable oil FAME. J Am Oil Chem Soc. 2003, 80, 281-286.