Biphasic synthesis of phenylacetic and phenylenediacetic acids by interfacial carbonylation of benzyl chloride and dichloro-p-xylene

Chemical Engineering Science

Volumn 51, Issue 5, 1996, Pages 757-767

  Zhong, Yaping ^a   Godfrey, Veronica M ^a   Lim, Phooi K ^a   Brown, Philip A ^b  

^a North Carolina State University   (United States)

^b MALLINCKRODT PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACTIVATION ENERGY; CARBON MONOXIDE; CARBONYLATION; CATALYST ACTIVITY; CATALYSTS; HYDROLYSIS; INTERFACES (MATERIALS); MATHEMATICAL MODELS; PALLADIUM; SODIUM COMPOUNDS; SUBSTRATES;

BENZYL CHLORIDE; DICHLOROXYLENE; DODECYL SODIUM SULFATE; KINETIC MODEL; PHENYLACETIC ACID; PHENYLENEDIACETIC ACID;

SYNTHESIS (CHEMICAL);

EID: 0030104320     PISSN: 00092509     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-2509(95)00300-2     Document Type: Article

References (22)

1. Alper, H., Hashem, K. and Heveling, J., 1982, Selective phase transfer and palladium(0)-catalyzed carbonylation, carbal-koxylation, and reduction reactions. Organometallics 1, 775-778.
2. Amer, I. and Alper, H., 1989, Lanthanide-promoted and nickel cyanide-catalyzed carbonylation reactions under phase-transfer conditions. J. Am. Chem. Soc. 111, 927-930.
3. Amiens, C., Decaro, D., Chaudret, B., Bradley, J. S., Mazel, R. and Roucau, C., 1993, Selective synthesis, characterization, and spectroscopic studies on a novel class of reduced platinum and palladium particles stabilized by carbonyl and phosphine ligands. J. Am. Chem. Soc. 115, 11,638-11,639.
4. Arzoumanian, H., Buono, G., Choukard, M.B. and Petrignani, J.-F., 1988, Asymmetric carbonylation of α-methylbenzyl bromide catalyzed by oxazaphospholane-palladium complexes under phase-transfer conditions. Organometallics 7, 59-62.
5. Cassar, L., Foa, M. and Gardano, A., 1976, The use of phase-transfer catalysis in palladium-catalyzed carbonylation of organic halides. J. Organometallic Chem. 121, C55-C56.
6. Cornils, B. and Wiebus, E., 1995, Aqueous catalysts for organic reactions. Chemtech 25, 33-38.
7. Dautenhahn, P. C. and Lim, P. K., 1992, Biphasic synthesis of poly(2,6-dimethyl-1,4-phenylene oxide) using a surface-active coupling catalyst. Ind. Engng Chem. Res. 31, 463-469.
8. Ganesan, S., Lloyd, P. B., Gilleskie, G. L. and Lim, P. K., 1989, Segregation and chemical conversion at oil-water interface. Chem. Engng Sci. 44, 171-177.
9. Giles, D. W., Cha, J. A. and Lim, P. K., 1986, The aerobic and peroxide-induced coupling of aqueous thiols - I. Kinetic results and engineering significance. Chem. Engng Sci. 41, 3129-3140.
10. 3)]. Inorg. Chem. 32, 4965-4967.
11. Herrmann, W. A. and Kohlpaintner, C. W., 1993, Water-soluble ligands, metal complexes, and catalysts: synergism of homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. Engl. 32, 1524-1544.
12. Kalck, P. and Monteil, F., 1992, Use of water-soluble ligands in homogeneous catalysis. Adv. Organomet. Chem. 34, 219-284.
13. Kudo, K., Hidai, M. and Uchida, Y., 1971, Synthesis and properties of stable palladium(0) carbonyl complexes containing triphenylphosphine. J. Organometallic Chem. 33, 393-398.
14. Kuntz, E. G., 1987, Homogeneous catalysis in water. Chemtech 17, 570-575.
15. Lim, P. K. and Zhong, Y., 1995, Chemically-benign synthesis at organic-water interface, in Designing Chemical Syntheses and Processing for the Environment (Edited by P. Anastas and T. Williamson). American Chemical Society, Washington, DC (in press).
16. Lloyd, P. B., Ganesan S. and Lim, P. K., 1989, Segregation of metals at the oil-water interface: results and implications. Ind. Engng Chem. Res. 28, 577-584.
17. 12. J. Chem. Soc. Chem. Commun. 3, 218-219.
18. Okano, T., Okabe, N. and Kiji, J., 1992, Palladium-catalyzed, atmospheric pressure carbonylation of allylic halides under the influence of sodium hydroxide or alkox-ides. A facile synthesis of β,γ-unsaturated acids. Bull. Chem. Soc. Japan 65, 2589-2593.
19. Okano, T., Uchida, I., Nakagaki, T., Konishi, H. and Kiji, J., 1989, Carbonylation of benzyl chloride catalyzed by water-soluble palladium phosphine complex in a two-phase system. J. Mol. Catal. 54, 65-71.
20. 4, an intermediate in CO insertion into the Pd-Me bond. J. Am. Chem. Soc. 115, 10,388-10389.
21. Zhong, Y., Abrams, C. F. and Lim, P. K., 1995a, Biphasic synthesis of poly(2,6-dimethyl- 1,4-phenylene oxide) using a surface-active coupling catalyst. 2. Process improvements, additional kinetic results, and proposed reaction mechanism. Ind. Engng Chem. Res. 34, 1529-1535.
22. Zhong, Y., Abrams, C. F., Lim, P. K. and P. A. Brown, 1995b, Biphasic autoxidation of tetralin using surface-active catalyst complexes. J. phys. Chem. (submitted).