Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Reexamination Certificate
2007-10-24
2009-08-04
Zucker, Paul A (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
Reexamination Certificate
active
07569719
ABSTRACT:
This invention relates to processes for producing electron deficient olefins, such as 2-cyanoacrylates, using an iminium salt, and if desired contacting the reaction byproduct with alkali to generate an amine and separating that amine therefrom.
REFERENCES:
patent: 2363464 (1944-11-01), Senkus
patent: 2413249 (1946-12-01), Senkus
patent: 2413250 (1946-12-01), Senkus
patent: 2415046 (1947-01-01), Senkus
patent: 2582128 (1952-01-01), Hurwitz
patent: 2721858 (1955-10-01), Joyner et al.
patent: 2756251 (1956-07-01), Joyner et al.
patent: 2763677 (1956-09-01), Jeremias
patent: 3142698 (1964-07-01), Halpern et al.
patent: 3903055 (1975-09-01), Buck
patent: 3975422 (1976-08-01), Buck
patent: 3988299 (1976-10-01), Malofsky
patent: 4003942 (1977-01-01), Buck
patent: 4012402 (1977-03-01), Buck
patent: 4013703 (1977-03-01), Buck
patent: 4202920 (1980-05-01), Renner et al.
patent: 4364876 (1982-12-01), Kimura et al.
patent: 4512357 (1985-04-01), Earl
patent: 4556700 (1985-12-01), Harris et al.
patent: 4587059 (1986-05-01), Harth et al.
patent: 4622414 (1986-11-01), McKervey
patent: 4636539 (1987-01-01), Harris et al.
patent: 4695615 (1987-09-01), Leonard et al.
patent: 4718966 (1988-01-01), Harris et al.
patent: 4837260 (1989-06-01), Sato et al.
patent: 4855461 (1989-08-01), Harris
patent: 4876045 (1989-10-01), Longo et al.
patent: 4906317 (1990-03-01), Liu
patent: 5142098 (1992-08-01), Bru-Magniez et al.
patent: 5288794 (1994-02-01), Attarwala
patent: 5306752 (1994-04-01), Attarwala
patent: 5312864 (1994-05-01), Wenz et al.
patent: 5328944 (1994-07-01), Attarwala et al.
patent: 5424343 (1995-06-01), Attarwala
patent: 5424344 (1995-06-01), Lewin
patent: 5455369 (1995-10-01), Meier et al.
patent: 5624699 (1997-04-01), Lang
patent: 5703267 (1997-12-01), Takahashi et al.
patent: 5744642 (1998-04-01), Lantzsch et al.
patent: 6093780 (2000-07-01), Attarwala
patent: 6096848 (2000-08-01), Gololobov et al.
patent: 6245933 (2001-06-01), Malofsky et al.
patent: 6291544 (2001-09-01), Kotzev
patent: 6531460 (2003-03-01), Takenouchi et al.
patent: 6835789 (2004-12-01), Kneafsey et al.
patent: 2006/0094833 (2006-05-01), McDonnell et al.
patent: 0 459 617 (1991-12-01), None
patent: WO 94/15590 (1994-07-01), None
patent: WO 95/32183 (1995-11-01), None
patent: WO 99/14206 (1999-03-01), None
patent: WO 03/006225 (2003-01-01), None
patent: WO 03/086605 (2003-10-01), None
Carl, J. Buck, Unequivocal Synthesis of Bis(2-Cyanoacrylate) Monomers, I. Via Anthracene Adducts,Journal of Polymer Science, Polymer Chemistry Edition, vol. 16, 2475-507 (1978).
G. Jones, “The Knoevenagle Condensation”,Organic Reactions, vol. XV, 204, Wiley New York (1967).
F. Bigi et al., “Montmorillonite KSF as an Inorganic, Water Stable, and Reusable Catalyst for the Knoevenagel Synthesis of Coumarin-3-carboxylic Acids”,Journal Organic Chemistry, vol. 64, 1033-35 (1999).
B. Green et al., Synthesis of Steroidal 16, 17-Fused Unsaturated δ-Lactones1,Journal Organic Chemistry, vol. 50, 640-44 (1985).
P. Rao et al., “Zinc Chloride As A New Catalyst For Knoevenagel Condensation”,Tetrahedron Letters, vol. 32, No. 41, 5821-22 (1991).
J. S. Yadav et al., “Phosphane-Catalyzed Knoevenagel Condensation: A Facile Synthesis of Cyanoacrylates and α-Cyanonitriles”,European Journal Organic Chemistry, 546-51 (2004).
L. Tietze et al., Comprehensive Organic Synthesis, Pergamon Press, Oxford, vol. 2, Chapter 1.11, 341 (1991).
P. Laszlo, “Catalysis of Organic Reactions by Inorganic Solids”,Accounts of Chemical Research, vol. 19, 121-27 (1986).
K. Kloestra et al., “Base and Acid Catalysis by the Alkali-containing MCM-41 Mesoporous Molecular Sieve”,Journal Chemical Soc. Chem. Commun., 1005-06 (1995).
P. Lednor et al., “The Use of a High Surface Area Silicon Oxynitride as a Solid, Basic Catalyst”,Journal Chemical Society, Chem. Commun., 1625-26 (1991).
F. Bigi et al., “A Revision of the Biginelli Reaction Under Solid Acid Catalysis. Solvent-free Synthesis Of Dihydropyrimidines Over Montmorillonite KSF”,Tetrahedron Letters, vol. 40, 3456-68 (1999).
F. Bigi et al., “Clean synthesis in water: uncatalysed preparation of ylidenemalononitriles”,Green Chemistry, vol. 2, 101-03 (2000).
R. Breslow, “Hydrophobic Effects on Simple Organic Reactions in Water”,Accounts of Chemical Research, vol. 24, 159-64 (1991).
C. Li, “Organic Reactions in Aqueous Media—With a Focus on Carbon-Carbon Bond Formation”,Chemical Reviews, vol. 93, 2023-35 (1993).
T. Welton, “Room Temperature Ionic Liquids, Solvents for Synthesis and Catalysis”,Chemical Reviews, vol. 99, 2071-83 (1999).
D. Morrison et al., “Base-promoted reactions in ionic liquid solvents. The Knoevenagel and Robinson annulation reactions”,Tetrahderon Letters, vol. 42, 6053-55 (2001).
Fraga-Dubreiul et al., “Grafted ionic liquid-phase-supported synthesis of small organic molecules”,Tetrahderon Letter, vol. 42, 6097-6100 (2001).
M. Smietana et al., “Preparation of Silyl Enol Ethers Using (Bistrimethylsilyl)acetamide in Ionic Liquids”,Organic Letters, vol. 3, No. 7, 1037-39 (2001).
Li et al., “n-Butyl Pyridinium Nitrate as a Reusale Ionic Liquid Medium for Knoevenagel Condensation”,Chinese Chemical Letters, vol. 14, No. 5, 448-50 (2003).
J. Harjani et al., “Lewis acidic ionic liquids for the synthesis of electrophilic alkenes via the Knoevenagel condensation”,Tetrahedron Letters, vol. 43, 1127-30 (2002).
Xu et al., “Knoevenagel condensation Reaction Catalyzed by Functionalized Ionic Liquid 1-(2-Hydroxyethyl)-3-methyl Imidazolium Chloride”,Chinese Journal of Organic Chemistry, vol. 24(10), 1253-56 (2004).
Su et al., “Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate”,Synthesis 2003, No. 4, 555-59 (2003).
Moehrle et al., “Aminomethylierung von 1,3-Diketonen”,Pharmazie, vol. 40, 697-701 (1985).
J. March, “Reactions”,Advanced Organic Chemistry, 3rdEdition, Wiley & Sons Inc., 417 (1985).
J. March, “Addition to Carbon-Hetero Multiple Bonds”,Advanced Organic Chemistry, 3rdEdition, Wiley & Sons, 802-03 (1985).
M. B. Smith,Organic Synthesis, McGraw Hill International Chemistry Series, 1302 (1994).
Tehrani et al., “Product Class 8: Iminium Salts”,Science of Synthesis, vol. 27, 313-48 (2004).
B. Hin et al., “Facile Synthesis of α-Substituted Acrylate Esters”,Journal of Organic Chemistry, vol. 67, 7365-68 (2002).
Holy et al., “The Mannich Reaction-II Derivatization of Aldehydes and Ketones Using Dimethyl(methylene)ammonium Salts”,Tetrahedron Letters, vol. 5, 613-19 (1979).
Bryson et al., “Preformed Mannich Salts: A Facile Preparation of Dimethyl(methylene)ammonium Iodide”,Journal of Organic Chemistry, vol. 45, 524-25 (1980).
J. March, “The Pinacol Rearrangement”,Advanced Organic Chemistry, 3rdEdition, Wiley & Sons, 963-64 (1985).
J. March, “Free-Radical Substitution”,Advanced Organic Chemistry, 3rdEdition, Wiley & Sons, 642 (1985).
Jahn et al., “A Novel and Simple Method for the Preparation of Iminium Salts”,Tetrahderon Letters, vol. 34, No. 37, 5863-66 (1993).
R. J. Vijin et al., Synthesis, 573 (1994).
Davis, “Chemistry Letters”, vol. 33, Issue 9, 1072-77 (2004).
Davis et al., “Ionic Liquids in Synthesis”, P. Wasserscheld and T. Welton, eds., Wiley-VCH Verlag GmbH & Co., KGaA, Chapter 2 (2002).
M.G. Djamali, P. Burba, K.H. Lieser, “Synthese und Eigenschaften eines Celluloseaustauschers mit Diaminodibenzo-18-Krone-6 als Ankergruppe”, Die Angewandte Makromolecular Chemie, vol. 92, 145-54 (1980).
K. Babic, “Reactive and Functional Polymers”, vol. 66, 1494-1505 (2006).
Trumbo et al., “Copolymerization Behavior of 3-Isopropenyl-α,α-Dimethylbenzylamine and Preliminary Evalu
McArdle Ciaran B.
Zhao Ligang
Bauman Steven C.
Loctite (R&D) Limited
Zucker Paul A
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