Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2011-08-23
2011-08-23
Sullivan, Daniel (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
Reexamination Certificate
active
08003818
ABSTRACT:
The invention provides a process for the hydrogenation of a reactant selected from the group consisting of: at the ring-closing carbon atom and has a proton at a(a) a 5- or 6-membered lactone that is substituted carbon atom adjacent to the ring-closing carbon atom;(b) an ester of a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group; and(c) a carboxylic acid having a gamma-carbonyl group and a proton at a carbon atom adjacent to the carbon atom of the carbonyl group,wherein the reactant is contacted with a strongly acidic heterogeneous catalyst comprising a hydrogenating metal, in the presence of hydrogen, at a temperature in the range of from 100 to 350° C. and a pressure in the range of from 1 to 150 bar (absolute).The invention further provides a fuel composition, preferably a diesel composition, comprising di-alkyl 4-methylnonanedioate or di-alkyl 3-ethyl-4-methylheptanedioate.
REFERENCES:
patent: 3849457 (1974-11-01), Haag
patent: 3968294 (1976-07-01), Robitschek et al.
patent: 4048196 (1977-09-01), Broecker et al.
patent: 4301077 (1981-11-01), Pesa et al.
patent: 4594130 (1986-06-01), Chang et al.
patent: 4652685 (1987-03-01), Cawse et al.
patent: 4797382 (1989-01-01), De Thomas et al.
patent: 4885411 (1989-12-01), De Thomas et al.
patent: 4904342 (1990-02-01), Arnoldy et al.
patent: 5068105 (1991-11-01), Lewis et al.
patent: 5456964 (1995-10-01), Tamura et al.
patent: 5596113 (1997-01-01), Douglas et al.
patent: 5608105 (1997-03-01), Fitzpatrick
patent: 5614564 (1997-03-01), Hwang et al.
patent: 5883266 (1999-03-01), Elliott et al.
patent: 5892107 (1999-04-01), Farone et al.
patent: 6054611 (2000-04-01), Farone et al.
patent: 6527914 (2003-03-01), Shevchenko et al.
patent: 6894199 (2005-05-01), Heikkila et al.
patent: 2002/0069987 (2002-06-01), Pye
patent: 2004/0224902 (2004-11-01), Shukla et al.
patent: 2004/0231810 (2004-11-01), Rouso et al.
patent: 2005/0221078 (2005-10-01), Lu et al.
patent: 2006/0135793 (2006-06-01), Blessing et al.
patent: 2006/0162239 (2006-07-01), Van Den Brink et al.
patent: 2007/0034345 (2007-02-01), Petrus et al.
patent: 2007/0100162 (2007-05-01), Petrus et al.
patent: 0069409 (1983-01-01), None
patent: 69409 (1985-11-01), None
patent: 472474 (1996-01-01), None
patent: 1036878 (2000-09-01), None
patent: 1240580 (1971-07-01), None
patent: 2040275 (1980-08-01), None
patent: 05140323 (1993-06-01), None
patent: 7-18269 (1995-01-01), None
patent: 09059519 (1997-03-01), None
patent: 11029647 (1999-02-01), None
patent: 82/00483 (1982-02-01), None
patent: 98/26869 (1998-06-01), None
patent: 99/65851 (1999-12-01), None
patent: 01/59202 (2001-08-01), None
patent: 02/074760 (2002-09-01), None
patent: WO 02085833 (2002-10-01), None
patent: 2003/014231 (2003-02-01), None
patent: 2005/058856 (2005-06-01), None
patent: 2005/059016 (2005-06-01), None
Wan et al., Ruthenium(II)-sulfonated BINAP: a novel water-soluble asymmetric hydrogenation catalyst, Tetrahedron: Asymmetry (1993), 4(12), 2461-2468.
Behr et at., Aqueous biphasic catalysis as a powerful tool for catalyst recycling in telomerization and hydrogenation chemistry, Green Chemistry (2003), 5(2), 198-204.
Fabre et al., Catalytic Hydrogenation of Arabinonic Acid and Lactones to Arabitol, Journal of Catalysis (2002), 208(1), 247-254.
Henin et al., {Enantioselective photodeconjugation of conjugated esters and lactones in the presence of ephedrine, Tetrahedron (1989), 45(19), 6171-96}.
Melikyan et al., {Low-molecular-weight bioregulators. III. Synthesis of 4E-tridecenyl acetate, the sex pheromone ofKeiferia lycopersicella, Khimiya Prirodnykh Soedinenii (1990), (1), 102-6}.
European Patent Office Search Report dated Jun. 22, 2005, Application No. 04106969.1.
Kirk-Othmer's Encyclopedia of Chemical Technology, 3rd ed., 1981, vol. 13, p. 909.
Ullmann's Encyclopedia of Industrial Chemistry, 5th ed., 1990, vol. A15, p. 80.
Smook, Handbook for Pulp and Paper Technologies, Angus Wilde Publications, 2nd edition, p. 333., 1992.
Copending U.S. Appl. No. 11/420,981 (United States Publication No. US2007/00034345 A1), 2007.
Copending U.S. Appl. No. 11/582,888 (United States Publication No. US2007/0100162 A1), 2007.
Heitz et al., “Solvent Effects on Liquefaction: Solubilization Profiles of a Canadian Prototype Wood,Populus deltoides, in the Presence of Different Solvents”, Can. J. Chem. Eng., 72:1021-1027, Dec. 1994.
Yamada, “Rapid Liquefaction of Lignocellulosic Waste by Using Ethylene Carbonate” Biores. Technol., 70:61-67,1999.
European Search Report for Application No. 03 25 7858, 2009.
Leonard, H., “Levulinic Acid as a Basic Chemical Raw Material,” Newport Industries, Inc., Pensacola, Florida, 48(6):1331-1341, Aug. 1956.
Lange Jean-Paul
Petrus Leonardus
Van Den Brink Peter John
Von Hebel Klaas Lambertus
Sawyer Jennifer Cho
Shell Oil Company
Sullivan Daniel
LandOfFree
Process for the hydrogenation of a lactone or of a... 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 hydrogenation of a lactone or of a..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the hydrogenation of a lactone or of a... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2795780