Radical telomerization of 3,3,3-trifluoropropene with diethyl hydrogen phosphonate: Characterization of the first telomeric adducts and assessment of the transfer constants

Journal of Fluorine Chemistry

Volumn 128, Issue 8, 2007, Pages 910-918

  Kostov, George ^a   Ameduri, Bruno ^a   Brandstadter, Stephan M ^b  

^a Hopital Saint Charles   (France)

^b LANXESS DEUTSCHLAND GMBH   (Germany)

Author keywords

3,3,3 Trifluoropropene; Diethyl hydrogen phosphonate; Kinetics of telomerization; Nuclear magnetic resonance; Radical telomerization; Transfer constant

Indexed keywords

EID: 34447318353     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2007.03.015     Document Type: Article

References (45)

1. C. Heid, D. Hoffmann, J. Polster, Ger. Patent 2,233,941 (1974); Chem. Abs. 81, 79 674b (1974) (assigned to Cassella Farbwerke Mainkur AG).
2. J. Mondt, Ger. Patent 3,128,143 (1983); Chem. Abs. 98, 145 138j (1983) (assigned to Hoechst AG).
3. W. Bloechl, Ger Patent 1,254,150 (1967); Chem. Abs. 68, 49 763u (1967).
4. K. Matsui, M. Ohayashi, E. Itou, S. Kondou, Jap. Patent 57,142,926 (1982); Chem. Abs. 98, 34 296 (1983) (assigned to Sagami Chem Res).
5. Stackman R.W. Ind. Eng. Chem., Prod. Res. Dev. 21 (1982) 328-332
6. Mahmood T., and Shreeve J.M. Inorg. Chem. 25 (1986) 3128-3133
7. Yamabe M., Akiyama K., Akatsuka Y., and Kato M. Eur. Polym. J. 36 (2000) 1035-1043
8. Chiotis A., Clouet G., and Brossas J. Polym. Bull. 7 (1982) 303-309
9. Shimata M., and Nakamura Y. ACS Symposium Series vol. 212 (1983), American Chemical Society, Washington, DC p. 237
10. J.A. Bittles, A.M. Joyce, US Patent 2,559,754 (1951); Chem. Abs., 46, 1026 (1952) (assigned to DuPont).
11. Brace N.O. J. Org. Chem. 3 (1961) 3197-3204
12. Inukai K., Ueda T., and Maramatsu H. J. Org. Chem. 29 (1964) 2224-2228
13. Haszeldine R.N., Hobson D.L., and Taylor D.R. J. Fluor. Chem. 8 (1976) 115-121
14. Boutevin B., Hervaud Y., and Pietrasanta Y. Phosphorus Sulfur 20 (1984) 197-204 (and references herein)
15. Boutevin B., Hervaud Y., and Pietrasanta Y. Phosphorus, Silicon Sulfur 20 (1984) 189-195
16. Hall C.R., Inch T.D., and Williams N.E. J. Chem. Soc., Perkin Trans. 1 (1985) 233-240
17. Blackburn G.M., and Kent D.E. J. Chem. Soc., Perkin Trans. 1 (1986) 6-12
18. D.J. Burton, R. Guneratne, W. Cen, R.L. Kirchmeier, A.S. Modak, W.A. Sanderson, J.M. Shreeve, D. Su, PCT Int. Patent WO 90,07,513 (1990); Chem. Abs. 114, 122 2704a (1990) (assigned to Gas Research Institute).
19. O.V. Korenchenko, Y.Y. Ivanov, A.Y. Aksinenko, V.A. Sokolov, I.V. Martinov, Khim. Farm. Zh. 26 (1992) 21-29; Chem. Abs. 118, 59 786u (1992).
20. Gaboyard M., Hervaud Y., and Boutevin B. J. Fluor. Chem. 107 (2001) 5-13 (and references herein)
21. Duc M., Ameduri B., and Boutevin B. J. Fluor. Chem. 112 (2001) 3-12
22. Pelaprat N., Rigal G., Boutevin B., Manséri A., and Belbachir M. Eur. Polym. J. 32 (1996) 1189-1195 (and references herein)
23. Brondino C., Boutevin B., Hervaud Y., Pelaprat N., and Manséri A. J. Fluor. Chem. 76 (1996) 193-201 (and references herein)
24. L.H. Chance, J.P. Moreau, US Patent 3,910,886 (1976) (assigned to US Agriculture).
25. A.N. Bolstad, US Patent 2,842,529 (1958) (assigned to 3M Co).
26. Sianesi D., and Caporiccio G. Makromol. Chem. (1965) 264-273
27. Brown D.W., and Wall L.A. J. Polym. Sci., Part A: Polym. Chem. 6 5 (1968) 1367-1375
28. D. Sianesi, G. Caporiccio, BE Patent 618320 (1962) (assigned to Montecatini).
29. Golschmidt A. J. Am. Chem. Soc. 73 (1951) 2940-2947
30. Brown D.W. Polym. Preprint (J. Amer. Chem. Soc.) 6 (1965) 965-971
31. Ameduri B., and Boutevin B. Well-Architectured Fluoropolymers: Synthesis, Properties and Applications (2004), Elsevier, Amsterdam p. 67
32. Vasil'eva T.T., Kochetkova V.A., Dostovalova V.I., Nelyubin B.V., and Freidlina R.K. Izv. Akad. Nauk SSSR, Ser. Khim. (1987) 808-816
33. Vasil'eva T.T., Kochetkova V.A., Dostovalova V.I., Nelyubin B.V., and Freidlina R.K. Izv. Akad. Nauk SSSR, Ser. Khim. (1989) 2558-2564
34. Vasil'eva T.T., Fokina I.A., and Vitt S.V. Izv. Akad. Nauk SSSR, Ser. Khim. (1991) 1384-1392
35. St.M. Brandstadter, B. Ameduri, G.K. Kostov, World Patent WO 2005074528 (2005) (assigned to Great Lakes Chem. Co).
36. Zamyslov R.A. Zh. Vses. Khim. Obsh. 31 (1986) 589-595
37. Ikonnikov N.S., Lamova N.I., and Terent'ev A.B. Izv. Akad. Nauk SSSR, Ser. Khim. (1988) 117-124
38. H.D. Block, Ger. Patent 2,514,640 (1976); Chem. Abs. 86, 72 867m (1976) (assigned to Bayer AG).
39. Gao Y., and Shreeve J.M. J. Synth. Org. Chem. 7 (2004) 1072-1079
40. Duc M., Boutevin B., Améduri B., Kharroubi M., and Sage J.M. Macromol. Chem. Phys. 199 (1998) 1271-1289
41. Bauduin G., Boutevin B., Bertocchio R., Lantz A., and Vergé C. J. Fluor. Chem. 90 (1998) 107-115
42. Balague J., Améduri B., Boutevin B., and Caporiccio G. J. Fluor. Chem. 70 (1995) 215-223
43. Boutevin B., Maliszewicz M., and Pietrasanta Y. Makromol. Chem. 186 (1985) 1467-1475
44. David C., and Gosselain P.A. Tetrahedron 70 (1962) 639-642
45. Valade D., Boyer C., Lacroix Desmazes P., Ameduri B., and Boutevin B. J. Polym. Sci, Part A: Polym. Chem. 44 (2006) 5763-5777