Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2007-01-16
2007-01-16
Witherspoon, Sikarl A. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S877000
Reexamination Certificate
active
10400558
ABSTRACT:
3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
REFERENCES:
patent: 2660602 (1953-11-01), Wiese
patent: 3754052 (1973-08-01), Hoffman
patent: 3836553 (1974-09-01), Fenton et al.
patent: 3940446 (1976-02-01), Kahn
patent: 4110403 (1978-08-01), Ichikawa et al.
patent: 4175204 (1979-11-01), Babler
patent: 4359587 (1982-11-01), Abdurakhmanov et al.
patent: 4421938 (1983-12-01), Windawi
patent: 4433175 (1984-02-01), Kaufhold
patent: 4590313 (1986-05-01), Grey et al.
patent: 4891446 (1990-01-01), Slaugh
patent: 5103066 (1992-04-01), Dessau
patent: 5227530 (1993-07-01), Satek et al.
patent: 5480668 (1996-01-01), Nofre et al.
patent: 5510508 (1996-04-01), Claude et al.
patent: 5728862 (1998-03-01), Prakash
patent: 5770775 (1998-06-01), Katritzky et al.
patent: 5808062 (1998-09-01), Domagala et al.
patent: 5856584 (1999-01-01), Prakash et al.
patent: 0 529 804 (1996-04-01), None
patent: 0 747 123 (1996-12-01), None
patent: 0 866 073 (1998-09-01), None
patent: 0 884 299 (1998-12-01), None
patent: 693390 (1953-07-01), None
patent: 1 500 447 (1975-01-01), None
patent: 1 500 884 (1976-08-01), None
patent: WO 97/18035 (1997-05-01), None
patent: WO 97/49490 (1997-12-01), None
patent: WO 98/00233 (1998-01-01), None
patent: WO 99/21817 (1999-05-01), None
Banthorpe, D., et al., “Mechanism of Elimination Reactions. Part XX. The Inessentiality of Steric Strain in Biomolecular Olefin Elimination,” J. Chem. Soc., 1960, pp. 4054-4087 (incomplete copy).
Brandstrom, A., et al., “A Method for the Preparation oftert-Alkylacetic Acids,” Acta. Chem. Scand., vol. 13., No. 3, 1959, pp. 608-610.
Kosolapoff, G., “Preparation of Alcohols by the Grignard Method from Olefin Oxides. II. Synthesis of 3,3-dimethyl-1-butanol and 4,4-dimethyl-1-pentanol from Ethylene Oxide and 2-heptanol, and of 5-methyl-5-hexanol from Propylene Oxide,” Chem. Abstracts, vol. 43, No. 16, 1949, Abstract No. 6155b.
Nystrom, et al., “Reduction of Organic Compounds by Lithium Aluminum Hydride. II. Carboxylic Acids,” JACS, vol. 69, No. 1197, 1947, pp. 2548-2549.
Ipatieff, et al., “Study in the Terpene Series. X. Isomerization Accompanying Hydrogenolysis of Alcohols,” The Journal of the American Chemical Society, vol. 73, Feb. 1951, pp. 553-555.
Randriamahefa, et al., “Improved Synthesis of Tertiary Alkylacetic Acids and Esters,” Journal of Synthetic Organic Chemistry, No. 5, 1985, pp. 493-495.
Karleskind, et al., “Catalytic High Presusre Hydrogenation,” Oils and Fats Manual, vol. 2, pp. 1083-1084.
Pct International Search Report , PCT/US00/17946, Nov. 30, 2000, 5 pages.
Reid, M., et al., “Molecular Characterization of Microbial Alcohol Dehydrogenases,” Critical Reviews in Microbiology, 1994, 20(1), pp. 13-56.
Augustine, R., et al., “Hydrogenation V: Carbonyl Compounds,” Heterogeneous Catalysis for the Synthetic Chemist, Chapter 18, Jun. 1996, pp. 439-472.
Christiansen, J., et al., “A Method for the Preparation of Trialkylacetaldehydes,” Acta Chem. Scand. 13, No. 3, 1959, pp. 611-613.
Dave, P., et al., “An Improved Direct Oxidation of Alkyl Halides to Aldehydes,” Synthetic Communications, 16(11), 1986, pp. 1343-1346.
Kryukov, S., et al., “Synthesis of Oxygen-Containing Organic Compounds Based on C5-C6Olefins,” Neftekhimiya, undated, vol. 19, No. 5, pp. 762-766.
Cherkaev, V., et al., “Preparation of Aldehydes by Catalytic Dehydrogenation of Alcohols,” Maslo-Zhir. Prom. 34(11), 1968, pp. 22-25 (translated from Russian, Jan. 1999).
Gulkova, D., et al., “Dehydrogenation of Substituted Alcohols to Aldehydes on Zinc Oxide-Chromium Oxide Catalysts,” Czech. Collect. Chem. Commun., 1992, 57(11), pp. 2215-2226.
Jung, C., et al., “Dehydrogenation of Alcohols and Hydrogenation of Aldehydes Using Homogeneous Ruthenium Catalysts,” Organometallics, 1992, vol. 1, No. 4, pp. 658-666.
Krohn, K., et al., “Titanium- or Zirconium-Catalyzed Selective Dehydrogenation of Benzyl Alcohols to Aldehydes and Ketones withtert-Butyl Hydroperoxide,” Chem. Ber., 1990, 123(6), pp. 1357-1364.
Podrebarac, G., et al., “More Uses for Catalytic Distillation,” Chemtech, 1997, 27(5), pp. 37-45.
Aramendia, M., et al., “The Selectivity of NaZnPO4in the Dehydrogenation of Alcohols,” Chemistry Letters, 1994, Issue 8, pp. 1361-1364.
Liu, X. et al., “The Bis(bipyridine)copper(II)-Induced Activation of Dioxygen for the Catalytic Dehydrogenation of Alcohols,” J. Am. Chem. Soc, Nov. 10, 1992, 115(8), pp. 3239-3243.
Dobson, A., et al., “Complexes of the Platinum Metals. 7.1Homogenous Ruthenium and Osmium Catalysts for the Dehydrogenation of Primary and Secondary Alcohols,” Inorganic Chemistry, 1977, vol. 16, No. 1, pp. 137-142.
Rybak, W., et al., “Dehydrogenation of Alcohols Catalyzed by Polystyrene-Supported Ruthenium Complexes,” J. Mol. Catal., 1981, 11(2-3), pp. 365-370.
Neumann, R., “Mixed Addenda Phosphomolybdovanadates as Catalysts for Oxidations with Dioxygen and Hydrogen Peroxide,” Polyoxometalates, pp. 307-313.
Simpson, M., et al., “Catalytic Applications of Rhodium Complexes Containing Trialkylphosphines,” Coordination Chemistry Reviewed, 1996, 155, pp. 163-207.
Zhang, B., et al., “Metal Fibre—A Novel Catalyst Material for Selective Dehydrogenation of Alcohols,” Proceedings of the 10th International Congress on Catalysis, Jul. 19-24, 1992, pp. 2177-2280.
Yanagisawa, A., et al., “Selective Isomerization of 1,2-Epoxyalkanes to Aldehydes with Lithum Dialkylamides,” J. Chem. Sco., Chem. Commun., 1994, pp. 2103-2104.
Mischitz, M., et al., “Asymmetric Microbial Hydrolysis of Epoxides,” Tetrahedron: Asymmetry, 1995, vol. 6, No. 6, pp. 1261-1272.
Ipatieff, V., et al., “Study in the Terpene Series. X. Isomerization of Accompanying Hydrogenolysis of Alcohols,” Ipatieff High Pressure and Catalytic Laboratory, Department of Chemistry, Northwestern University, Feb. 1951, pp. 553-555.
Wann, S., et al., “Reduction of Carboxylic Acid Derivatives by BH4in Acidic Dimethyl Sulfoxide,” J. Org. Chem., 1981, 46, pp. 2579-2581.
Adkins, H., et al., “The Preparation of Aldehydes and Ketones by Dehydrogenation of Alcohols Over Copper-Chromium Oxide,” The Journal of The American Chemical Society, Jul. 1933, pp. 2992-2994, vol. 55, Easton, PA, US.
Ebner Jerry R.
Guo Zhi
Hershman Arnold
Klein Loraine M.
McGhee William D.
Senniger Powers
The Nutrasweet Company
Witherspoon Sikarl A.
LandOfFree
Process for the preparation of 3,3-dimethylbutanal does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of 3,3-dimethylbutanal, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of 3,3-dimethylbutanal will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3726231