The catalytic hydration of 1,2-, 1,3- and 1,4-dicyanobenzenes using nickel(0) catalysts

Journal of Molecular Catalysis A: Chemical

Volumn 266, Issue 1-2, 2007, Pages 139-148

  Crisóstomo, Carmela ^a   Crestani, Marco G ^a   García, Juventino J ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Catalysis; Dinitriles; Homogeneous; Hydration; Nickel

Indexed keywords

BENZENE; CATALYSIS; CATALYST ACTIVITY; HYDRATION; NICKEL COMPOUNDS; POLYAMIDES;

CYANOBENZAMIDES; DINITRILES; HOMOGENEOUS CATALYTIC HYDRATION; HYDRATION PRODUCTS;

CATALYSTS;

EID: 33947162403     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.10.054     Document Type: Article

References (52)

1. Recent reviews regarding the nitrile hydration process, both metal-mediated (stoichiometric), metal-catalyzed, and enzymatic hydrolysis:
2. Kukushkin V.Y., and Pombeiro A.J.L. Inorg. Chim. Acta 358 (2005) 1-21
3. Bokach N.A., and Kukushkin V.Y. Russ. Chem. Rev. 74 (2005) 153-170
4. Martínková L., and Mylerová V. Curr. Org. Chem. 7 (2003) 1279-1295
5. Kukushkin V.Y., and Pombeiro A.J.L. Chem. Rev. 102 (2002) 1771-1802
6. Maniar K.K. Polym. Plast. Technol. Eng. 43 (2004) 427-443
7. Ullmann's Encyclopedia of Industrial Chemistry, vol. 13. 6th ed. (2003), Wiley-VCH, Weinheim pp. 467-479
8. Ullmann's Encyclopedia of Industrial Chemistry, vol. 28. 6th ed. (2003), Wiley-VCH, Weinheim pp. 25-53
9. Levchik S.V., and Weil E.D. Polym. Int. 49 (2000) 1033-1073
10. Subbulakshmi M.S., Kasturiya N., Hansraj P., Bajaj A.K., and Agarwal J.M.S. Rev. Macromol. Chem. Phys. C 40 (2000) 85-104
11. Seavey K.C., Khare N.P., Liu Y.A., Williams T.N., and Chen C.-C. Ind. Eng. Chem. Res. 42 (2003) 3900-3913
12. T. Okawa, Mitsubishi Gas Chemical Co., Ltd., Japan. Jpn. Kokai Tokkyo Koho, Patent No. JP 2002322138, 2002.
13. M. Dotani, T. Ookawa, Mitsubishi Gas Chemical Co., Japan. Jpn. Kokai Tokkyo Koho, Patent No. JP 06128204, 1994
14. M. Dotani, T. Ookawa, Mitsubishi Gas Chemical Co., Japan. Jpn. Kokai Tokkyo Koho, Patent No. JP 06116221, 1994.
15. Breno K.L., Pluth M.D., and Tyler D.R. Organometallics 22 (2003) 1203-1211
16. L. Hartmut, Zimmer A.-G., Germany. Eur. Pat. Appl., Patent No. EP 684271, 1995
17. W. Hirosuke, H. Yoshinori, U. Takashi, Mitsubishi Chemical Industries Co., Ltd., Japan. Jpn. Kokai Tokkyo Koho, Patent No. JP 63014760, 1988.
18. Rey P., Rossi J.-C., Taillades J., Gros G., and Nore O.J. Agric. Food Chem. 52 (2004) 8155-8162
19. Franz E., and Steffen O. Synthesis 12 (2001) 1866-1872
20. Cull S.G., Woodley J.M., and Lye G.J. Biocatal. Biotransform. 19 (2001) 131-154
21. Some recent patents granted to Du Pont and BASF for the direct preparation of polyamides by polycondensation of dinitrile hydrolyzates and diamines, protected in a large number of countries, illustrate these facts and can be consulted in:
22. R.A. Hayes, D.N. Marks, M. de J. Van Eijndhoven, H.B. Sunkara, E. I. Du Pont de Nemours & Co., USA. PCT Int. Appl. Patent No. WO 2001079327, 2001
23. R.A. Hayes, D.N. Marks, M. De J. Van Eijndhove, E. I. Du Pont de Nemours & Co., USA. PCT Int. Appl. Patent No. WO 2000037537, 2000
24. F. Ohlbach, H. Luyken, BASF A.-G., Germany. Ger. Offen., Patent No. DE 19935398, 2001.
25. García J.J., Arévalo A., Brunkan N.M., and Jones W.D. Organometallics 23 (2004) 3997-4002
26. Garcia J.J., Brunkan N.M., and Jones W.D. J. Am. Chem. Soc. 124 (2002) 9547-9555
27. Garcia J.J., and Jones W.D. Organometallics 19 (2000) 5544-5545
28. A recent theoretical work that stresses the importance of strong electron donating ligands for the stabilization of the side-on coordination of a -CN moiety to a transition metal center can be consulted, in:
29. Huo C.F., Zeng T., Li Y.W., Beller M., and Jiao H. Organometallics 24 (2005) 6037-6042
30. Crestani M.G., Arévalo A., and García J.J. Adv. Synth. Catal. 348 (2006) 732-742
31. Ghaffar T., and Parkins A.W. J. Mol. Catal. A: Chem. 160 (2000) 249-261
32. Tfouni E., de Souza Macêdo A.M., Nunes Cardoso L., Queiroz Ferreira K., de Oliveira E.C., and Novais da Rocha Z. Inorg. Chim. Acta 358 (2005) 2909-2920
33. Angus P.M., and Jackson W.G. Inorg. Chim. Acta 343 (2003) 95-104
34. Balahura R.J., and Purcell W.L. Inorg. Chem. 20 (1981) 4159-4163
35. Balahura R.J., and Purcell W.L. Inorg. Chem. 18 (1979) 937-941
36. C-P coupling constants; an effect that is seemingly most dramatic in the case of complex 4.
37. C-P coupling constants from the series (indicated in Table 2) and in this instance, it seems reasonable to conclude that from all DCB substrates, it is this complex that would depict the more electron poor character at the coordinated -CN moiety and thus probably, the faster hydration rate.
38. 2-coordinated carbonyls, proposed herein.
39. 2-C,C-3-CN-quinoline)] were also confirmed; the former complex been found to evolve in THF solution only after an initial coordination of the nitrile to the corresponding [(dippe)Ni] moiety. (see Scheme 1, also in Ref. [9b]).
40. The alternative of nickel(0) going on and off for catalysis would imply that all nickel(0) intermediates required to yield the complete hydration of 1,3- and 1,4-DCB would have been formed within 72 h, at 180 °C. In the case of 1,2-DCB the same premise might imply additionally, that at the same temperature the free nickel catalysts should coordinate to the 1,2-phthalamide produced in situ in a fashion not conducive towards further hydration, therefore, not producing the corresponding dicarboxylic acid. Still, the selectivity and yield afforded at 120 °C for such product and not to 2-cyanobenzamide which would be expected to form otherwise, specially if free [(dippe)Ni] catalysts were to react randomly, an explanation based on an intramolecular migration of these species was found to be reasonable, at least for the time being.
41. Chou M.H., Szalda D.J., Creutz C., and Sutin N. Inorg. Chem. 33 (1994) 1674-1684
42. Chou M.H., Brunschwig B.S., Creutz C., Sutin N., Yeh A., Chang R.C., and Lin C.-T. Inorg. Chem. 31 (1992) 5347-5348
43. Scott F., Krüger C., and Betz P. J. Organomet. Chem. 387 (1990) 113-121
44. Vicic D.A., and Jones W.D. J. Am. Chem. Soc. 119 (1997) 10855-10856
45. Cloke F.G.N., Gibson V.C., Green M.L.H., Mtetwa V.S.B., and Prout K. J. Chem. Soc., Dalton Trans. (1988) 2227-2229
46. In: Weast R.C., and Astle M.J. (Eds). CRC Handbook of Data on Organic Compounds, V. I (A-O), fourth printing (1987), CRC Press Inc., Boca Raton 796-798
47. In: Weast R.C., and Astle M.J. (Eds). CRC Handbook of Data on Organic Compounds, V. II (P-Z), fourth printing (1987), CRC Press Inc., Boca Raton 110, 111, 113, 117, 321, 322
48. In: Budavari S. (Ed). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 11th ed. (1989), Merck & Co. Inc., Rahway 5080, 7342, 9095
49. The National Institute of Advanced Industrial Science and Technology (AIST), Japan, in: http://www.aist.go.jp/RIODB/SDBS/.
50. Advanced Chemistry Development Inc., ACD/HNMR Predictor, Version 5.11, 2001.
51. Advanced Chemistry Development Inc., ACD/CNMR Predictor, Version 5.10, 2001.
52. Advanced Chemistry Development Inc., ACD/ChemSketch, Version 5.08, 2001.