Method for producing alcohols

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

Reexamination Certificate

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C568S830000, C568S914000

Reexamination Certificate

active

07569735

ABSTRACT:
A method for producing alcohols which comprises reducing esters or lactones with hydrogen gas in the presence of a catalyst comprising (i) a ruthenium compound, (ii) a monodentate monophosphine or a bidentate bisphosphine, and (iii) an amine. Examples of the catalyst include a ruthenium (Ru) complex represented by the formula:RuX1X2(LP)m(LN)n[X1and X2each represent an anionic ligand, LPrepresents a phosphine ligand, m is 1 when LPis bidentate, while m is 2 when LPis monodentate, LNrepresents an amine ligand, and n is 1 when LNis bidentate, while n is 2 when LNis monodentate.] and a catalyst comprising an amine and a ruthenium (Ru) complex of the formula: RuX1X2(LP1)r[LP1represents a monophosphine ligand and r is 3 or 4.].

REFERENCES:
patent: 2001-247499 (2001-09-01), None
patent: 2004-238306 (2004-08-01), None
patent: 2004-300131 (2004-10-01), None
patent: 2005-524704 (2005-08-01), None
patent: 11-189600 (1999-07-01), None
patent: WO 2006/106483 (2006-10-01), None
patent: WO 2006/106484 (2006-10-01), None
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Nomura, K., et al., “Direct synthesis of 2-phenylethanol by hydrogenation of methyl phenylacetate using homogeneous ruthenium-phosphine catalysis under low hydrogen pressure”, Journal of Molecular Catalysis A: Chemical, 2001, pp. 345-349, vol. 166, Elsevier.
Zhang, J., et al., “Efficient Homogeneous Catalytic Hydrogenation of Esters to Alcohols”, Angewandte Chemie Int. Ed., 2006, pp. 1113-1115, vol. 45, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Kitamura, M., et al., “Asymmetric Hydrogenation of 3-OXO Carboxylates Using BINAP-Ruthenium Complexes: (R)-(-)-Methyl 3-Hydroxybutanoate (Butanoic acid, 3-hydroxy-, methyl ester, (R)-)”, Org. Synth., 1993, pp. 1-13.
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Saudan, L., et al., “Dihydrogen Reduction of Carboxylic Esters to Alcohols under the Catalysis of Homogeneous Ruthenium Complexes: High Efficiency and Unprecedented Chemoselectivity”, Angew. Chem. Int. Ed., Aug. 2007, pp. 7473-7476, vol. 46.
Teunissen, H., et al., “Homogeneous ruthenium catalyzed hydrogenation of esters to alcohols”, Chem. Commun., Jan. 1998, 1367-1368, vol. 1998.

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