Phosphonite containing catalysts for hydroformylation processes

Details Phosphonite containing catalysts for hydroformylation processes Phosphonite containing catalysts for hydroformylation processes

2011-01-18

2011-01-18

Witherspoon, Sikarl A (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus containing

C568S454000, C502S166000, C502S213000

Reexamination Certificate

active

07872157

ABSTRACT:
Novel trivalent organophosphonite ligands having the structure of general formula (I):wherein R is an alkyl or aryl group containing 1 to 30 carbon atoms; Ar1and Ar2are aryl groups containing 4 to 30 carbon atoms; R1 to R6 are H or alkyl or aryl hydrocarbon radicals containing 1 to 40 carbon atoms; and X is a connecting group or a simple chemical bond, were developed and found to be very active for hydroformylation processes for ethylenically unsaturated substrates. Catalyst solutions prepared from these ligands with a Rh metal show an unusual “ligand acceleration effect” for simple alkenes, i.e., the hydroformylation activity increases as the concentration of ligand increases, and are capable of producing linear or branched aldehydes under typical hydroformylation conditions.

REFERENCES:
patent: 4348495 (1982-09-01), Buysch et al.
patent: 4381359 (1983-04-01), Idel et al.
patent: 4599206 (1986-07-01), Billig et al.
patent: 4608239 (1986-08-01), Devon
patent: 4668651 (1987-05-01), Billig et al.
patent: 4835299 (1989-05-01), Maher et al.
patent: 4873213 (1989-10-01), Puckette et al.
patent: 4912155 (1990-03-01), Burton
patent: 5298541 (1994-03-01), Bohshar et al.
patent: 5712403 (1998-01-01), Sato et al.
patent: 5744649 (1998-04-01), Bryant et al.
patent: 5840647 (1998-11-01), Puckette et al.
patent: 6130358 (2000-10-01), Tolleson et al.
patent: 6265620 (2001-07-01), Urata et al.
patent: 6362354 (2002-03-01), Bunel et al.
patent: 6437192 (2002-08-01), Bunel
patent: 6440891 (2002-08-01), Maas et al.
patent: 6906225 (2005-06-01), Puckette et al.
patent: 6995292 (2006-02-01), Tolleson et al.
patent: 2003/0144559 (2003-07-01), Hess et al.
patent: 2007/0112219 (2007-05-01), Ortmann et al.
patent: 2008/0154067 (2008-06-01), Liu et al.
patent: 0 301 355 (1989-02-01), None
patent: 0 416 321 (1991-03-01), None
patent: 07 216157 (1995-08-01), None
patent: 2000-026355 (2000-01-01), None
patent: 2001-213834 (2001-08-01), None
patent: 2006/003431 (2006-01-01), None
patent: 2008/088495 (2008-07-01), None
patent: 2009/085161 (2009-07-01), None
Aubry et al., “The unusual inhibition of a dirhodium tetraphosphine-based bimetallic hydroformylation catalyst by PPh3”, C.R. Chimie 5, 2002, pp. 473-480.
Barros et al., “Rhodium catalyzed hydroformylation of conjugated dienes: Remarkable accelerative effect of triphenylphosphine”, Catalysis Communications 8, 2007, pp. 747-750.
Claver et al., “Biarylphosphonites: a class of monodentate phosphorus (III) ligands that outperform their chelating analogues in asymmetric hydrogenation catalysis”, Feb. 29, 2000, Apr. 17, 2000, P.G. Pringle, Chem. Comm., pp. 961-962.
da Silva et al., “Rhodium catalyzed hydroformylation of linalool”, Applied Catalysis A: General 309, 2006, pp. 169-176.
Diéguez et al., “High-Pressure Infrared Studies of Rhodium Complexes Containing Thiolate Bridge Ligands under Hydroformylation Conditions”, Organometallics, 1999, 18, pp. 2107-2115.
Gordon and Ford, The Chemist's Companion, Kinetics and Energetics, 1972, pp. 156-161, John Wiley & Sons, New York.
International Search Report and Written Opinion dated Mar. 26, 2009 for International Application No. PCT/US2008/013774.
International Search Report and Written Opinion dated Apr. 24, 2009 for International Application No. PCT/US2008/013773.
International Search Report and Written Opinion dated May 2, 2008 for International Application No. PCT/US2007/024968.
Jeon et al., “Hydroformylation of Mixed Octenes Using Rhodium=Bulky Phosphonite Complexes with Excellent Catalytic Activity and Stability”, The Chemical Society of Japan, 2004, pp. 174-175, vol. 33, No. 2.
Kalck, “Cooperative Effect Between Two Metal Centres in Hydroformylation: Routes Towards Heterobimetallic Catalysts”, Polyhedron, vol. 7, No. 22/23, pp. 2441-2450, 1988.
Kamer et al., “Rhodium Phosphite Catalysts” in Rhodium Catalyzed Hyrdoformylation, Edited by van Leeuwen et al., Kluwer Academic Publishers, 2000, pp. 35-62.
Meyer et al., “Preparation and Single Crystal X-Ray Diffraction Study of Some Fluorophosphites and Phosphite Esters”, Z. Naturforsch, Bi. Chem. Sci., 48b, pp. 659-671, 1993.
Notice of Allowance dated Apr. 27, 2009 for U.S. Appl. No. 11/941,217.
Office Action dated Jul. 20, 2007 from U.S. Appl. No. 11/670,628, abandoned.
Office Action dated Sep. 8, 2008 from co-pending U.S. Appl. No. 11/941,217.
Olivier and Booth, “Make Aldehydes by New Oxo Process”, Hydrocarbon Processing, Apr. 1970, pp. 112-114.
Puckette, “Halophosphite Ligands for the Rhodium Catalyzed Low-Pressure Hydroformylation Reaction” in “Catalysis of Organic Reactions”, Edited by S. R. Schmidt, CRC Press, 2006, pp. 31-38.
Quin, Louis D., “The Common 3-Coordinate Functions”, “A Guide to Organophosphorus Chemistry”, 2000, pp. 44-91, Chapter 3, Wiley-Interscience.
Selent et al., “Novel Oxyfunctionalized Phosphonite Ligands for the Hydroformylation of Isomeric n-Olefins”, Agnew. Chem. Inc., 2000, pp. 1639-1641, 39, No. 9, Wiley-VCH Verlag GmbH, D-69451 Weinheim, 2000.
Senderowitz et al., “A Smart Monte Carlo Technique for Free Energy Simulation of Muliconformational Molecules”, Journal Am. Soc., 1995, pp. 8211-8219, American Chemical Society.
Smith and March, March's Advanced Organic Chemistry, Free-Energy Differences between Equatorial and Axial Substiuents on a Cyclohexane Ring (A Values), pp. 174-175, 2001, Fifth Edition, John Wiley and Sons, Inc., New York.
Tullock and Coffman, “Synthesis of Fluorides by Metathesis with Sodium Fluoride”, J. Org. Chem., vol. 25, pp. 2016-2019, 1960.
U.S. Appl. No. 61/016,665 filed Dec. 26, 2007, Liu et al., now expired.
U.S. Appl. No. 61/016,661 filed Dec. 26, 2007; Liu, now expired.
U.S. Appl. No. 12/330,023 filed on Dec. 8, 2008.
U.S. Appl. No. 60/871,158 filed Dec. 21, 2006, Liu et al., now expired.
U.S. Appl. No. 11/670,628 filed Feb. 2, 2007, Liu et al., now abandoned.
U.S. Appl. No. 11/941,217 filed Nov. 16, 2007, Liu et al., now published as U.S. 2008-0154067.
U.S. Appl. No. 12/489,029 filed June 22, 2009, Puckette et al.
van Leeuwen and Roobeek, “Hydroformylation of Less Reactive Olefins with Modified Rhodium Catalysts”, Journal of Organometallic Chemistry, 258, 1983, pp. 343-350.
van Leeuwen et al., “Phosphines as ligands; Bite angle effects for diphosphines”, Rhodium Catalyzed Hyrdoformylation, Edited by van Leeuwen et al., Kluwer Academic Publishers, 2000, pp. 63-75.
van Rooy et al., “Bulky Diphosphite-Modified Rhodium Catalysts: Hydroformylation and Characterization”, Organometallics, 1996, 15, pp. 835-847.
White et al., “Structural Implications of Nuclear Magnetic Resonance Studies on 1-R-1-Phospha-2,6-dioxacyclohexanes”, Journal of the American Chemical Society, 92:24, Dec. 2, 1970, pp. 7125-7135.
Chandrasekaran et al., “The Effect of Very Bulky Groups on the Equilibrium of Penta- and Hexa- coordinated Phosphoranes”, Phosphorus, Sulfur, and Silicon, vol. 181, 2006, pp. 1493-1511.
Office Action date of notification Jan. 29, 2010 received in co-pending U.S. Appl. No. 12/489,029.
Notice of Allowance and Fees Due date of mailing May 27, 2010 received in co-pending U.S. Appl. No. 12/330,023.
Notice of Allowance and Fees Due date of mailing Mar. 1, 2010 received in co-pending U.S. Appl. No. 12/330,023.
Notice of Allowance and Fees Due date of mailing Nov. 16, 2009 received in co-pending U.S. Appl. No. 12/330,023.
Notice of Allowance and Fees Due date of mailing Jul. 23, 2009 received in co-pending U.S. Appl. No. 12/330,023.
Notification of Transmittal of the International Search Report and the Written Opinion of the International Searching Authority, or the Declaration date of mailing Aug. 9, 2010 received in International Application No. PCT/US10/01642.

Affiliated with

Also associated with

Rating

Phosphonite containing catalysts for hydroformylation processes does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Phosphonite containing catalysts for hydroformylation processes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phosphonite containing catalysts for hydroformylation processes will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2723074