Organic compounds -- part of the class 532-570 series – Organic compounds – Carbonate esters
Reexamination Certificate
2006-01-24
2006-01-24
Shameem, Golam M M (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbonate esters
C558S260000, C558S276000
Reexamination Certificate
active
06989459
ABSTRACT:
Applicant has discovered an in situ method of preparing quaternary ammonium methocarbonate salts and quaternary ammonium alkylcarbonate salts in high yield from tertiary amines, methanol, and at least one of a cyclic carbonate, an aliphatic polyester (such as a polycarbonate), or an ester (such as a carbonate ester), and their subsequent conversion to quaternary ammonium bicarbonates, quaternary ammonium carbonates or both in a one-pot reaction. According to one embodiment of the invention, the method includes reacting an amine and methanol with at least one of a cyclic carbonate and an aliphatic polyester to yield a quaternary ammonium methocarbonate. This method does not produce or require the handling of corrosive quaternary ammonium hydroxides. Another embodiment is a method of preparing quaternary ammonium alkylcarbonate salts by reacting tertiary amines, methanol, and an ester. The quaternary ammonium methocarbonate or alkylcarbonate can be converted to the corresponding bicarbonate, carbonate, or mixture thereof by methods known in the art.
REFERENCES:
patent: 2635100 (1953-04-01), Werntz et al.
patent: 3642858 (1972-02-01), Frevel et al.
patent: 3803201 (1974-04-01), Gilpin et al.
patent: 4062884 (1977-12-01), Romano et al.
patent: 4181676 (1980-01-01), Buysch et al.
patent: 4572769 (1986-02-01), Shimizu
patent: 4634509 (1987-01-01), Shimizu et al.
patent: 4652667 (1987-03-01), Green
patent: 4661609 (1987-04-01), Knifton
patent: 4691041 (1987-09-01), Duranleau et al.
patent: 4734518 (1988-03-01), Knifton
patent: 4776929 (1988-10-01), Aoyami et al.
patent: 4892944 (1990-01-01), Mori et al.
patent: 5091543 (1992-02-01), Grey
patent: 5214182 (1993-05-01), Knifton
patent: 5438034 (1995-08-01), Walker
patent: 5523487 (1996-06-01), Walker
patent: 5833741 (1998-11-01), Walker
patent: 6080789 (2000-06-01), Lutz
patent: 0291074 (1988-11-01), None
Chemical Abstract 108:194813.
Chemical Abstract 109:140942c.
Chemical Abstract 144:246824j.
Chemical Abstract 116:58737a.
Chemical Abstract 116:20680p.
Chemical Abstract 117:191329f.
Chemical Abstract 118:168685f.
Chemical Abstract 112:186941y.
Chemical Abstract 123:9063p.
Chemical Abstract 116:83918t.
Chemical Abstract 108:195813j.
Chemical Abstract 109:200000f.
Chemical Abstract 110:212114e.
Chemical Abstract 112:9801h.
Chemical Abstract 122:186906r
Chemical Abstract 125:186942z.
Chemical Abstract 114:246809h.
Chemical Abstract 115:282480y.
Chemical Abstract 117:214936t.
Chemical Abstract 117:111138e.
Chemical Abstract 119:138758k.
Chemical Abstract 119:141608s.
Chemical Abstract 118:254406x.
Chemical Abstract 115:282446s.
Chemical Abstract 121:230349s.
Chemical Abstract 117:193966k.
Chemical Abstract 116:237798t.
Chemical Abstract 116:193723h.
Chemical Abstract 112:258494j.
Chemical Abstract 121:38041u.
Chemical Abstract 121:179111d.
Chemical Abstract 121:133543t.
Chemical Abstract 114:246810b.
Chemical Abstract 95:6499c.
Chemical Abstract 122:160111c.
Chemical Abstract 122:160112d.
Chemical Abstract 122:217155b, and 122:217155c.
Chemical Abstract 118:80498m.
Chemical Abstract 111:23523x.
Chemical Abstract 122:132593t.
“Reactions of Trihalogenated Esters with Triethylamine and Anions”, Arlene C. Pierce and Madeleine M. Joullie,J. Org. Chem.vol. 27, pp. 3968-3973 (1962).
“Industrial Organic Nitrogen Compounds”, ASTLE . . . Ed; Reinhold Pub. (1961), p. 61.
“Reaction of Xanthates witht-Amines, VI. The Reaction Mechanism”, Hiroshi Yoshida,Bull. of Chem. Soc. of JP,vol. 42, p. 1948-1954 (1969).
“Zur solvensfreien Darstellung von Tetramethylammoniumsalzen: Synthese und Charakterisierung von et al.”, B. Altert und M. Jansen,Z. Anorg. Allg. Chem.621, p. 1735-1740 (1995).
“The Rate of Addition of Methyl Esters to Trimethylamine”,JACS55:4079-4089 (Oct. 1933).
Yagi, O. et al.: “Synthesis of pure tetramethylammonium hydroxide solution free from chloride ion by the electrolysis of its hydrogen carbonate” Chemistry Letters, vol. 12, 1993, pp. 2041-2044, XP002218995 p. 2042; table 1.
Database WPI, Section Ch, Week 199141, Derwent Publications Ltd., London, GB; AN 1991-298749; XP002218996 & JP 03 197449 A (Mitsui Petrochem Ind Co Ltd), Aug. 28, 1991, abstract.
Database WPI, Section Ch, Week 199517, Derwent Publications Ltd., London, GB; AN 1995-128295, XP002218997 & JP 07 053478 A (Mitsubishi Gas Chem Co Inc), Feb. 28, 1995, abstract.
Int'l Search Report mailed Nov. 27, 2002 for Int's Application No. PCT/US 02/21236.
Darby & Darby
Lonza Inc.
Shameem Golam M M
LandOfFree
In situ process for preparing quaternary ammonium... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with In situ process for preparing quaternary ammonium..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and In situ process for preparing quaternary ammonium... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3604137