Abstract
Water can be used very advantageously as the solvent in homogeneous catalytic reactions and thus gives rise to a specific class of aqueous biphasic reactions among two-phase reactions. This new use of water has two very positive consequences: an advantageous effect on the selectivity of the homogeneous catalytic reactions and the opportunity, for the first time, to “immobilize” the homogeneous catalyst by means of the “liquid support” water, then to separate it simply and immediately from the reaction products after its task is complete and thus to return it to the catalysis cycle. Apart from the industrial use of hydroformylation (oxo process), fine chemicals are also being increasingly prepared by the aqueous, homogeneously catalyzed biphasic technique.
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References
Lubineau A (1996) Chemistry & Industry Feb 19, 123; Lubineau A, Augé J, Queneau Y (1994) Synthesis 8:714
Lubineau A (1998) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis-concepts and applications. Wiley-VCH, Weinheim, chap 2.1
Li Ch-J (1993) Chem Rev 93:2023
Southern TG (1989) Polyhedron 8(4):407
Cornils B, Herrmann WA (eds) (1998) Aqueous-phase organometallic catalysis-concepts and applications, Wiley-VCH, Weinheim
Parshall GW, Ittel SD (1992) Homogeneous catalysis, 2nd edn.; Wiley-Interscience, New York
Dickson RS (1985) Homogeneous catalysis with compounds of rhodium and iridium. Reidel, Dordrecht, Boston
Cornils B (1980) Hydroformylation. In: Falbe J (ed) New syntheses with carbon monoxide, Springer, Berlin Heidelberg New York, p 177
Gick W (Celanese, Ruhrchemie works), private communication
cf. Cornils B (1980) Hydroformylation. In: Falbe J (ed) New syntheses with carbon monoxide, Springer, Berlin Heidelberg New York, p 158 ff
e.g. Abraham MH, Grellier PL, Nasehzadeh A, Walker RAC ( 1988) J Chem Soc Perkin Trans 2:1717
Nienburg H (1953) DE Patent 948 150 Chemische Verwertungsgesellschaft Oberhausen mbH; Falbe J (ed) (1980) New syntheses with carbon monoxide, Springer, Berlin Heidelberg New York, sect 1.6.2.1.2
Kolling H, Büchner K, Stiebling E ( 1965) DE Patent 949 737, ( 1952) GB Patent 736875 Ruhrchemie AG
Tummes H, Meis J (1965) US Patent 3 462 500 Ruhrchemie AG
Manassen J (1973) In: Basolo F, Burwell RL (eds) Catalysis in research, Plenum, London, p183
cf. Panster P, Wieland St in Herrmann WA (eds) Applied homomogeneous catalysis with organometallic complexes, vols 1–2, VCH, Weinheim [53], section 3.1.1.3; Artley TR (1985) Supported metal complexes. Reidel, Dordrecht; Ford WT (1984) CHEMTECH 7:436
Cornils B, preliminary results
Keim W (1984) Chem Ing Tech 56:850; Bauer RS, Orinda HC, Glockner PW, Keim W (1972) US Patent 3 635 937 Shell Oil Comp
Joó F, Beck MT ( 1975) React Kin Catal Lett 2:257
Kuntz EG (1976) FR Patent 2 314 910,2 349 562,2 338 253,2 366 237 Rhône-Poulenc
In Sep. 1971 Celanese Chem. Co. started commercial Rh-catalyzed propylene oxo unit at Bishop,TX-first one in the world; cf. Celanese Annual Report 1974, p 9; Hughes OR, Douglas ME (1971) DE-OS Patent 2 125 382 Celanese Corp
Fowler R, Connor H, Baehl RA (1976) CHEMTECH 772
Osborn JA, Wilkinson G, Young JF (1965) Chem Commun 17, 131; Osborne JA, Jardine FH, Young JF, Wilkinson G (1966) J Chem Soc A 1711
Slaugh, LH, Mullineaux RD (1966) US Patent 3 239.566 and 3 239 571 Shell Oil Co
Cornils B, Kuntz EG (1995) J Organomet Chem 502:177
Cornils B (1998) Org Proc Res Dev 2:121
Cornils B, Falbe J (1984) Proc 4th Int Symp on Homogeneous Catalysis, Leningrad, p 487
Bach H, Gick W, Wiebus E, Cornils B ( 1984) Int Symp High-Pressure Chem Eng, Erlangen, Germany, Preprints, p 129
Bach H, Gick W, Wiebus E, Cornils B, (1984) 8th ICC, Berlin, Preprints, vol V, p 417; Chem Abstr (1987) 106:198.051; cited also in Behr A, Röper M (1984) Erdgas und Kohle 37(11):485
Bach H, Gick W, Wiebus E, Cornils B (1986) 1st IUPAC Symp Org Chem, Jerusalem, Abstracts, p 295
Wiebus E, Cornils B (1994) Chem-Ing-Tech 66:916
Cornils B, Wiebus E (1995) CHEMTECH 25:33
Wiebus E, Cornils B (1996) Hydrocarb Proc March, 63
Cornils B (1998) Ind Catal News No 2
Cornils B (1998) J Mol Catal, A 143:10
Cornils B, Kohlpaintner CW, Wiebus E ( 1998) In: McKetta JJ (ed) Encyclopedia of chemical processing and design, Marcel Dekker, New York, Vol. 66, p 273
Hildebrand JH (1935) J Am Chem Soc 57:866
Duve G, Fuchs O, Overbeck H (1976) Lösemittel, 6th edn. Hoechst AG, Frankfurt/M, p 49; also cited in Reichardt C (1990) Solvents and solvent effects in organic chemistry, VCH, Weinheim, Fig 2-2
Cornils B,W iebus E (1996) Recl TravChim Pays-Bas 115:211
Wachsen O, Himmler K, Cornils B (1998) Catalysis Today, 42:373
Beller M, Cornils B, Frohning CD Kohlpaintner CW (1995) J Mol Catal A 104:17
Cornils B (1980) Hydroformylation. In: Falbe J (ed) New syntheses with carbon monoxide, Springer, Berlin Heidelberg New York, p 174
Behr A, Keim W (1987) Erdöl Erdgas Kohle 103:126; Behr A (1998) Chem-Ing-Tech 70:685
Deshpande RM, Divekar SS, Bhanage BM, Chaudhari RV (1992) J Mol Catal A 75:L19; Purwanto P, Delmas H (1994) Symposium: Catalysis in Multiphase Reactors, Lyon, France, Abstracts C IV-2; Purwanto P, Delmas H (1995) Catal Today 24:135; Tinucci, L, Platona E (1989) EP Patent 0 380 154 Eniricerche SpA; Hablot I, Jenck J, Casamatta G, Delmas H (1992) Chem Eng Sci 47:2689; Bahrmann H, Cornils B, Konkol W, Lipps W ( 1984) DE-OS Patent 3 412 335 Ruhrchemie AG; Bahrmann H, Lappe P (1992) EP Patent 0 602 463 Hoechst AG
Cornils B, Bahrmann H, Lipps W, Konkol W (1985) DE Patent 3 511 428 Ruhrchemie AG
Kanagasabapathy S, Xia Z, Papadogianakis G, Fell B (1995) J Prakt Chem/Chem Ztg 337:446; Fell B, Papadogianakis G (1991) J Mol Catal 66:143; Ding H, Hanson BE, Bartik T, Bartik B (1994) Organometallics 13:3761; Russell MJH, Murrer BA (1983) US Patent 4 399 312 Johnson Matthey plc; Cornils B, Konkol W, Bahrmann H, Bach HW, Wiebus E (1984) DE Patent 3 411 034 Ruhrchemie AG; Bahrmann H, Papadogianakis G, Fell B (1989) EP Patent 0 435 084 Hoechst AG
Bahrmann H, Cornils B, Konkol W, Lipps W (1984) DE Patent 3 420 491 Ruhrchemie AG
Andriollo, A et al (1997) J Mol Catal A 116:157; Bahrmann H et al (1996) J Organomet Chem 520:97; Smith RT, Ungar RK, Sanderson LJ, Baird MC (1983) Organometallics 2:1138; Smith RT, Baird MC (1982) Inorg Chim Acta 62:135; Haggin J (1995) Chem Eng News April 17, 25; Ding H, Kang J, Hanson BE, Kohlpaintner, CW (1997) J Mol Catal A 124:21; Amrani Y, Sinou D (1984) J Mol Catal 24:231; Herd O, Langhans KP, Stelzer O, Weferling N, Sheldrick WS (1993) Angew Chem 105:1097; Manassen J, Dror Y (1983) US Patent 4 415 500 Yeda Res and Dev Comp; Herrmann WA, Gooßen LJ, Köcher C, Artus GRJ (1996) Angew Chem 108:2980; (1995) 107:2602; Herrmann WA et al (1995) J Mol Catal A 97:65
Ding H, Hanson BE (1995) J Mol Catal A 99:131
Herrmann WA, Kellner J, Riepl H (1990) J Organomet Chem 389:103; Russell MJH,Murrer BA (1980) DE Patent 3 135 127 Johnson Matthey plc; Buhling A, Kamer PCJ, van Leeuwen PWNM, Elgersma JW (1995) J Mol Catal A 98, 69; Buhling A, Kamer PCJ, van Leeuwen PWNM, Elgersma JW (1997) J Mol Catal 116:297; Lavenot L, Roucoux A, Patin H (1997) J Mol Catal A 118:153; Bahrmann H, Cornils B, Konkol W, Lipps W, Wiebus E et al ( 1984) EP Patent 0 163 234, (1984) EP Patent 0 183 200, (1984) DE-OS Patent 3 447 030, (1985) EP Patents 0 216 315, (1987) EP Patent 0 302 375 Ruhrchemie AG/Hoechst AG
Ritter U, Winkhofer N, Schmidt H-G, Roesky HW (1996) Angew Chem Int Ed Engl 35:524; Herrmann WA, Kulpe J, Kellner J, Riepl H ( 1988) EP Patent 0 372 313 Hoechst AG
Jin Z,Y an Y, Zuo H, Fell B (1996) J Prakt Chem/Chem Ztg 338:124; (1997) J Mol Catal A 116:55
Chen J, Alper H (1996) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic complexes, vol 2. VCH, Weinheim, p 844; Bergbreiter DE (1987) CHEMTECH Nov 688; Bergbreiter DE, Zhang L, Mariagnanam (1993) J Am Chem Soc 115:9295; Cenini S, Ragaini F (1996) J Mol Catal A 105:145; Manassen J (1971) Platinium Metal Rev 15:142; Mercier F, Mathey F (1993) J Organomet Chem 462:103; Bayer E, Schurig V (1975) Angew Chem Int Ed Engl 14:493; (1976) CHEMTECH March, 212
Chaudhari RV, Bhanage BM, Deshpande RM, Delmas H (1995) Nature 373:501; Fell B, Papadogianakis G (1993) J Prakt Chem/Chem Ztg 335:75
Sawamura M, Kitayama K, Ito Y (1993) Tetrahedron Asymmetry 4:1829; Monflier E, Fremy, G, Castanet Y, Mortreux A ( 1995) Angew Chem 107:2450
Arhancet JP, Davis ME, Merola JS, Hanson BE (1989) Nature 339:454; (1990) J Catal 121:327; Dav ME (1992) CHEMTECH August, 498; Joó F, Beck MT (1984) J Mol Catal 24:135; Fremy G, Monflier E, Carpentier J-F, Castanet Y, Mortreux A (1995) Angew Chem 107:1608
Anderson JR et al (1997) J Mol Catal A 116:109; Yamashita K et al (1993) EP Patent 0 552 908 Asahi Kasei KK
Healy FJ, Livingston JR, Mozeleski EJ, Stevens JG ( 1994) US Patent 5 298 669 Exxon Chem Patent Inc; Gosser LW, Knoth WH, Parshall GW (1977) J Mol Catal 2:253; Bahrmann H, Haubs M, Kreuder W, Müller T (1988) EP 0 374 615 Hoechst AG; IT Horváth et al (1998) J Am Chem Soc 120:3133
Jin Z, Zheng X (1998) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis-concepts and applications, Wiley-VCH, Weinheim, p 233
Bahrmann H (1996) In: Cornils B, Herrmann WA (eds) Applied homomogeneous catalysis with organometallic complexes, vols 1–2, VCH, Weinheim
Bahrmann H, Haubs M, Müller T, Schöpper N, Cornils B (1997) J Organomet Chem 545/546:139
Cornils B, Wiebus E et al (1984) DE-OS Patent 3 413 427 and EP Patent 0 158 246 Ruhrchemie AG
Deshpande RM,P urwanto P, Delmas H, Chaudhari RV (1997) J Mol Catal A 126:133
N. Yoshimura (1998) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis-concepts and applications, Wiley-VCH, Weinheim, chap 6.7; Bahrmann H ( 1996) In: Cornils B, Herrmann WA (eds) Applied homomogeneous catalysis with organometallic complexes, vol 2, VCH, Weinheim, p 351
Mercier C, Chabardes P (1994) Pure Appl Chem 66:1509
Kohlpaintner CW, Beller M (1997) J Mol Catal 116:259
S Haber (1998) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis-concepts and applications, Wiley-VCH, Weinheim, chap 6. 10
Horváth IT, Rábai J (1994) Science 266:72
Chauvin Y, Olivier-Bourbigou H (1995) CHEMTECH Sept 26; Olivier H, (1998) In: Cornils B, Herrmann WA (eds) Aqueous-phase organometallic catalysis-concepts and applications, Wiley-VCH, Weinheim, chap 6.10
Subramaniam B, McHugh MA ( 1986) Ind Eng Chem Proc Des Dev 25:1; Rathke JW, Klingler RJ, Krause TR (1991) Organometallics 10:1350; Kainz S, Koch D,Baumann W, Leitner W (1997) Angew Chem 109:1699; Angew Chem Int Ed Engl 36:1628
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Cornils, B. (1999). Modern Solvent Systems in Industrial Homogeneous Catalysis. In: Knochel, P. (eds) Modern Solvents in Organic Synthesis. Topics in Current Chemistry, vol 206. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48664-X_6
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