Processes and catalyst compositions for hydrocyanation of monool

Details Processes and catalyst compositions for hydrocyanation of monool Processes and catalyst compositions for hydrocyanation of monool

1995-04-26

1997-11-18

Richter, Johann

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

Organic compounds

Nitriles

558337, C07C25330

Patent

active

056889860

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to processes and catalyst compositions useful in the hydrocyanation of monoolefins. In particular, the invention relates to the hydrocyanation of monoolefins using zero-valent nickel and a bidentate phosphite ligand in the presence of a Lewis acid promoter.
BACKGROUND OF THE INVENTION
Hydrocyanation catalyst systems, particularly pertaining to the hydrocyanation of olefins, are known in the art. For example, systems useful for the hydrocyanation of butadiene to form pentenenitrile and in the subsequent hydrocyanation of pentenenitrile (PN) to form adiponitrile (ADN), are known in the commercially important nylon synthesis field. The hydrocyanation of olefins using transition metal complexes with monodentate phosphite ligand is documented in the prior art. See for example; U.S. Pat. Nos. 3,496,215, 3,631,191, 3,655,723 and 3,766,237, and Tolman, C. A.; McKinney, R. J.; Seidel, W. C.; Druliner, J. D.; and Stevens, W. R.; Advances in Catalysis, 33, 1, 1985.
The hydrocyanation of activated olefins such as with conjugated olefins (e.g., butadiene and styrene) and strained olefins (e.g., norbornene) proceeds without the use of a Lewis acid promoter, while hydrocyanation of unactivated olefins such as 1-octene and 3-pentenenitrile requires the use of a Lewis acid promoter. Teachings regarding the use of a promoter in the hydrocyanation reaction appear, for example, in U.S. Pat. No. 3,496,217. This patent discloses an improvement in hydrocyanation using a promoter selected from a large number of metal cation compounds with a variety of anions as catalyst promoters.
U.S. Pat. No. 3,496,218 discloses a nickel hydrocyanation catalyst promoted with various boron-containing compounds, including triphenylboron and alkali metal borohydrides. U.S. Pat. No. 4,774,353 discloses a process for the preparation of dinitriles, including ADN, from unsaturated nitriles, including PN, in the presence of a zero-valent nickel catalyst and a triorganotin catalyst promoter. U.S. Pat. No. 4,874,884 discloses a process for producing ADN by the zero-valent nickel catalyzed hydrocyanation of pentenenitriles in the presence of a synergistic combination of promoters selected in accordance with the reaction kinetics of the ADN synthesis.
Bidentate phosphite ligands similar to those used in the present invention for the hydrocyanation of monoolefins have been shown to be useful ligands in the hydrocyanation of activated olefins. See, for example: Baker, M. J., and Pringle, P. G.; J. Chem. Soc., Chem. Commun., 1292, 1991; Baker, M. J.; Harrison, K. N.; Orpen, A. G.; Pringle, P. G.; and Shaw, G.; J. Chem. Soc.; Chem. Commun., 803, 1991, Union Carbide, WO 93,03839.
Also, some of the ligands of the present invention have been disclosed with rhodium in catalyst complexes useful for the hydroformylation of functionalized olefins; see, Cuny, G. D., Buchwald, S. L., J. Am. Chem. Soc. 1993, 115, 2066.
The present invention provides for novel processes and catalyst precursor compositions which are more rapid, selective, efficient and stable than current processes and catalyst complexes employed in the hydrocyanation of monoolefins. Other objects and advantages of the present invention will become apparent to those skilled in the art upon reference to the detailed description of the invention which hereinafter follows.


SUMMARY OF THE INVENTION

The present invention provides a process for hydrocyanation comprising reacting a nonconjugated acyclic aliphatic monoolefin, a monoolefin conjugated to an ester group, e.g., methyl pent-2-eneoate, or a monoolefin conjugated to a nitrile group, e.g., 3-pentenenitrile; with a source of HCN in the presence of a catalyst precursor composition comprising zero-valent nickel and a bidentate phosphite ligand of Formula I, ##STR1## wherein each R.sup.1 is independently a tertiary substituted hydrocarbon of up to 12 carbon atoms, or OR.sup.4 wherein R.sup.4 is C.sub.1 to C.sub.12 alkyl; 12 carbon atoms; organonitrile. Preferably, the reaction is carried out in the presence o

REFERENCES:
patent: 3496210 (1970-02-01), Drinkard, Jr. et al.
patent: 3496215 (1970-02-01), Drinkard, Jr. et al.
patent: 3496217 (1970-02-01), Drinkard, Jr. et al.
patent: 3496218 (1970-02-01), Drinkard, Jr.
patent: 3536748 (1970-10-01), Drinkard, Jr. et al.
patent: 3547942 (1970-12-01), Godefroi et al.
patent: 3574701 (1971-04-01), Kominami et al.
patent: 3578695 (1971-05-01), Milberger et al.
patent: 3584029 (1971-06-01), Kominami et al.
patent: 3631191 (1971-12-01), Kane et al.
patent: 3655723 (1972-04-01), Drinkard, Jr.
patent: 3676481 (1972-07-01), Chia
patent: 3739011 (1973-06-01), Drinkard, Jr.
patent: 3766231 (1973-10-01), Gosser et al.
patent: 3766237 (1973-10-01), Chia et al.
patent: 3773809 (1973-11-01), Walter
patent: 3775461 (1973-11-01), Drinkard et al.
patent: 3798256 (1974-03-01), King et al.
patent: 3846461 (1974-11-01), Shook, Jr.
patent: 3847959 (1974-11-01), Shook, Jr. et al.
patent: 3852325 (1974-12-01), King
patent: 3852328 (1974-12-01), Chia et al.
patent: 3852329 (1974-12-01), Tomlinson
patent: 3853948 (1974-12-01), Drinkard, Jr. et al.
patent: 3865864 (1975-02-01), Nakajima et al.
patent: 3869500 (1975-03-01), Kominami et al.
patent: 3903120 (1975-09-01), Shook, Jr. et al.
patent: 3925445 (1975-12-01), King et al.
patent: 4298546 (1981-11-01), McGill
patent: 4371474 (1983-02-01), Rapoport
patent: 4599206 (1986-07-01), Billig et al.
patent: 4668651 (1987-05-01), Billig et al.
patent: 4688651 (1987-08-01), Dysart
patent: 4705881 (1987-11-01), Rapoport
patent: 4714773 (1987-12-01), Rapoport
patent: 4717775 (1988-01-01), Billig et al.
patent: 4769498 (1988-09-01), Billig et al.
patent: 4774353 (1988-09-01), Hall et al.
patent: 4783546 (1988-11-01), Burke et al.
patent: 4810815 (1989-03-01), Bryndza
patent: 4874884 (1989-10-01), McKinney et al.
patent: 5202297 (1993-04-01), Lorz et al.
patent: 5235113 (1993-08-01), Sato et al.
patent: 5312957 (1994-05-01), Casalnuovo et al.
patent: 5312996 (1994-05-01), Packett
patent: 5360938 (1994-11-01), Babin et al.
patent: 5364950 (1994-11-01), Babin et al.
patent: 5440067 (1995-08-01), Druliner
patent: 5491266 (1996-02-01), Babin et al.
patent: 5512695 (1996-04-01), Kreutzer et al.
Cuny, G.D. et al, "Practical, High-Yield, Regioselective, Rhodium-Catalyzed Hydroformylation of Functionalized .alpha.-Olefins", J. Am. Chem. Soc., 115, 2066-2068 (1993).
Burgstahler, A.W. et al, "Improved Modification of the Rosenmund Reduction", Synthesis, 767-768 (1976).
Tolman, C.A. et al, "Homogeneous Nickel-Catalyzed Olefin Hydrocyanation", Advances in Catalysis, 33 (1985).
Baker, M.J. et al, "Chelating Diphosphite Complexes of Nickel(0) and Platinum(0): Their Remarkable Stability and Hydrocyanation Activity", J. Chem. Soc., Chem. Commun., pp. 803-804 (1991).
Baker, M.J. et al, "Chiral Aryl Diphosphites: A New Class of Ligands for Hydrocyanation Catalysis", J. Chem. Soc., Chem. Communi., 1292-1293 (1991). Inorganic Chemistry, 9(10), 2354-2357 (1970).
Kurokawa, H. et al, "Skeletal Rearrangement of Unsaturated Nitriles over Solid-Base Catalysts", J. of Catalysis, 141, 94-101 (1993).
Pastor, S.D. et al, "Conformation of Eight-Membered Dioxathiasilocin Heterocycles in Solution", Phosphorus and Sulfur, 32, 105-111 (1987).
Yamada, F. et al, "Substituted Bisphenols as Antioxidants for Autoxidation of Tetralin", Bull. Chem. Soc. Japan, 62, 3603-3608 (1989).

Affiliated with

Also associated with

Rating

Processes and catalyst compositions for hydrocyanation of monool does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Processes and catalyst compositions for hydrocyanation of monool, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Processes and catalyst compositions for hydrocyanation of monool will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1567101