Integrate chemical processes for industrial utilization of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C568S852000, C568S909000, C568S909500

Reexamination Certificate

active

07576227

ABSTRACT:
Integrated processes of preparing industrial chemicals starting from seed oil feedstock compositions containing one or more unsaturated fatty acids or unsaturated fatty acid esters, which are essentially free of metathesis catalyst poisons, particularly hydroperoxides; metathesis of the feedstock composition with a lower olefin, such as ethylene, to form a reduced chain olefin, preferably, a reduced chain α-olefin, and a reduced chain unsaturated acid or ester, preferably, a reduced chain α,ω-unsaturated acid or ester. The reduced chain unsaturated acid or ester may be (trans)esterified to form a polyester polyolefin, which may be epoxidized to form a polyester polyepoxide. The reduced chain unsaturated acid or ester may be hydroformylated with reduction to produce an α,ω-hydroxy acid or α,ω-hydroxy ester, which may be (trans)esterified with a polyol to form an α,ωpolyester polyol. Alternatively, the reduced chain unsaturated acid or ester may be hydroformylated with reductive amination to produce an α,ω-amino acid or α,ω-amino ester, which may be (trans)esterified to form an α,ωpolyester polyamine.

REFERENCES:
patent: 4545941 (1985-10-01), Rosenburg
patent: 4560792 (1985-12-01), Banasiak
patent: 4772758 (1988-09-01), Kaufhold
patent: 4943397 (1990-07-01), Johnson
patent: 5143885 (1992-09-01), Warwel et al.
patent: 5218131 (1993-06-01), Warwel et al.
patent: 5312940 (1994-05-01), Grubbs et al.
patent: 5342985 (1994-08-01), Herrmann et al.
patent: 5352812 (1994-10-01), Feldman et al.
patent: 5539060 (1996-07-01), Tsunogae et al.
patent: 5932664 (1999-08-01), Chen et al.
patent: 5973082 (1999-10-01), Elmore
patent: 6060572 (2000-05-01), Gillis et al.
patent: 6156692 (2000-12-01), Nubel et al.
patent: 6197894 (2001-03-01), Sunaga et al.
patent: 6635768 (2003-10-01), Herrmann et al.
patent: 7247684 (2007-07-01), Lopez et al.
patent: A1-281594 (1990-08-01), None
patent: 41 07 056 (1992-09-01), None
patent: 4107056 (1992-09-01), None
patent: 100 41 345 (2002-03-01), None
patent: 0 084 437 (1983-07-01), None
patent: 0 099 572 (1984-02-01), None
patent: 0 108 571 (1984-05-01), None
patent: 0 328 230 (1989-08-01), None
patent: 56 077243 (1981-06-01), None
patent: 62083036 (1987-04-01), None
patent: 03 066725 (1991-03-01), None
patent: 2 058 298 (1996-04-01), None
patent: WO 91/14665 (1991-10-01), None
patent: WO 93/20111 (1993-10-01), None
patent: 96/04289 (1996-02-01), None
patent: WO 96/04289 (1996-02-01), None
patent: WO 97/06185 (1997-02-01), None
patent: WO 99/00397 (1999-01-01), None
patent: WO 99/22866 (1999-05-01), None
patent: WO 00/15339 (2000-03-01), None
patent: WO 00/18751 (2000-04-01), None
patent: WO 00/58322 (2000-10-01), None
patent: WO 00/71554 (2000-11-01), None
patent: WO 02/076920 (2002-10-01), None
patent: WO 2004/037754 (2004-05-01), None
patent: WO 2006/132902 (2006-12-01), None
Chem. Abstr. of CN-1052893, 1991.
Ahn, Yu Mi et al., “A Convenient Method for the Efficient Removal of Ruthenium Byproducts Generated During Olefin Metathesis Reactions”, Organic Letters, vol. 3, pp. 1411-1413 (2001).
Biemann, Ursula et al., “New Synthesis with Oils and Fats as Renewable Raw Materials for the Chemical Industry”, Angewandte Chemie Int. Ed., vol. 39, pp. m2207-2224 (2000).
Buchowicz, W. et al., “Catalytic Activity and Selectivity of Ru(=CHPh)Cl2(PCy3)2in the Metathesis of Linear Alkenes”, Journal of Molecular Catalysis A: Chemical, vol. 148, pp. 97-103 (1999).
Derwent Abstract, AN 1991-015326 (DD 281594).
Dowden, James et al., “Olefin Metathesis in Non-Degassed Solvent Using a Recyclable, Polymer Supported Alkylideneruthenium”, Chemical Communications, pp. 37-38 (2001).
Gessler, Simon et al., “Synthesis and Metathesis Reactions of a Phosphine-Free Dihydroimidazole carbine Ruthenium Complex”, Tetrahedron Letters, vol. 41, pp. 9973-9976 (2000).
Kingsbury, Jason et al., “A Recycable Ru-Based Metathesis Catalyst”, Journal of the American Chemical Society, vol. 121, pp. 791-799 (1999).
Mandelli, Dalmo et al., “Ethenolysis of Esters of Vegetable Oils: Effect of B2O3Addition to Re2O7/SiO2.Al2O3-SnBu4and CH3ReO3/SiO2.Al2O3Metathesis Catalysts”, Journal of the American Oil Chemical Society, vol. 73, pp. 229-232 (1996).
Maynard, Heather et al., “Purification Technique for the Removal of Ruthenium from Olefin Metathesis Reaction Products”, Tetrahedron Letters, vol. 40, pp. 4137-4140 (1999).
Nubel, P.O. et al., “A Convenient Catalyst System Employing RuCl3or RuBr3for Metathesis of Acyclic Olfeins”, Journal of Molecular Catalysis A: Chemical, vol. 145, pp. 323-327 (1999).
Paquette, Leo et al., “A Convenient Method for Removing All Highly-Colored Byproducts Generated During Olefin Metathesis Reactions”, Organic Letters, vol. 2, pp. 1259-1261 (2000).
Refvik, M.D. et al., “Ruthenium-Catalyzed Metathesis of Vegetable Oils”, Journal of the American Oil Chemical Society, vol. 76, pp. 93-98 (1999).
Warwel, Siegfried et al., “Polymers and Surfactants on the Basis of Renewable Resources”, Chemosphere, vol. 43, pp. 39-48 (2001).
Yao, Qingwei, “A Soluble Polymer-Bound Ruthenium Carbene Complex: A Robust and Reusable Catalyst for Ring-Closing Olefin Metathesis”, Angewandte Chemie Intl. Ed., vol. 39, pp. 3896-3898 (2000); (German version: Yao, Qingwei, “Ein Iöslicher, polymergebundener rutheniumcarbenkomplex: ein robuster und wiederverwendbarer Katalysator für Ringschluss-Olefinmetathesen”, Angewandte Chemie, vol. 112, pp. 4060-4063 (2000)).
“An Improved Process for the Synthesis of Unsaturated Alcohols”, filed in the United States of American on Oct. 9, 2003, U.S. Appl. No. 60/509,908; Applicant; Bob R. Maughon et al.
“An Improved Process for the Synthesis of Unsaturated Alcohols”, filed in the United States of America on Sep. 14, 2004, U.S. Appl. No. 10/940,403; Applicant; Bob R. Maughon et al.
“Metathesis of Unsaturated Fatty Acids Esters or Unsaturated Fatty Acids with Lower Olefins”, filed in the United States of American on Feb. 27, 2002, U.S. Appl. No. 10/469,321; Applicant; Thomas H. Newman, et al.
Derwent Abstract, Accession No. 1971-79633S (SU 291908 A).
“National Standards for Biodiesel,” http://www.journeyto forever.org; http://journeytoforever.org/biodiesel—yield2.html; pp. 3-6; Feb. 22, 2008.
“Hydroperoxide Concentrations Detected in Methyl Oleate Commercial Drum Samples,” Jul. 10, 2001 to Aug. 22, 2001.
Co-pending U.S. Appl. No. 11/915,794, filed Nov. 28, 2007, in the names of Kenneth A Burdett, Morteza Mokhtarzadeh and Francis J. Timmer, for “Metathesis Process for Preparing an Alpha, Omega-Functionalized Olefin,” ; equivalent to WO 2006/132902.
Burdett, Kenneth A., “Renewable Monomer Feedstocks via Olefin Metathesis: Fundamental Mechanistic Studies of Methyl Oleate Ethenolysis with the First-Generation Grubbs Catalyst”, Organometallics, vol. 23, pp. 2027-2047, 2004.
Burdett, Kenneth A., et al., “Stabilization of Olefin Metathesis Product Mixtures”, filed in the United States of America on Mar. 21, 2005, U.S. Appl. No. 10/528,472.
E-mail message from R. Varjian to Austin Chemical, dated Mar. 2, 2001.
E-mail message from R. Varjian to Austin Chemical, dated Mar. 29, 2001.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Integrate chemical processes for industrial utilization of... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Integrate chemical processes for industrial utilization of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Integrate chemical processes for industrial utilization of... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4105104

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.