Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2002-05-01
2004-07-20
O'Sullivan, Peter (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S090000, C564S096000
Reexamination Certificate
active
06765115
ABSTRACT:
FIELD OF THE INVENTION
The present invention is directed to a high yield process for producing dimetal sulfonyl amide salts which are highly useful as imidizing agents in the preparation of sulfonyl imides, which are in turn useful as strong acid catalysts, as electrolyte salts in electrochemical cells, and as monomers suitable for incorporation into ionomers. The products disclosed are useful in electrochemical applications such as batteries, fuel cells, electrolysis cells, ion exchange membranes, sensors and electrochemical capacitors.
BACKGROUND OF THE INVENTION
Methods for imidizing chemical compositions containing sulfonyl fluorides particularly fluorinated sulfonyl fluorides are known in the art. For example, DesMarteau, U.S. Pat. No. 5,463,005, discloses substituted perfluoro-olefins of the formula
where X═CH or N, Z═H, K, Na, or Group I or II metal, R=one or more fluorocarbon groups including fluorocarbon ethers and/or sulfonyl groups and/or perfluoro non-oxy acid groups, Y=perfluoroalkyl or F, and m=0 or 1.
Xue, Ph.D. thesis, Clemson University, 1996, discloses the formation of the monomer
CF
2
═CF—OCF
2
CF
2
SO
2
N(Na)SO
2
CF
3
by reaction of CF
2
═CF—OCF
2
CF
2
SO
2
Cl with CF
3
SO
2
NHNa in the presence of Na
2
CO
3
in acetonitrile
Further disclosed by Xue, op.cit,, is CF
3
SO
2
NNa
2
made by reacting a mixture of CF
3
SO
2
NHNa and NaH in THF for four hours at room temperature. Xue's CF
3
SO
2
NNa
2
composition is reacted with a cyclic sulfone of the formula
to produce the vinyl ether monomer, CF
2
═CF—OCF
2
CF
2
SO
2
N(Na)SO
2
CF
3
at a yield of 4%, the remainder of the product being two saturated species, both present in larger quantities.
Behrend and Haas, J. Fluorine Chem. 4 (1974) 99-106, disclose the synthesis of CF
3
SO
2
NAg
2
made from CF
3
SO
2
NAg
2
.NH
3
at 200° C. CF
3
SO
2
NAg
2
.NH
3
is formed from CF
3
SO
2
NH
2
and AgNO
3
in aqueous solution while adding an aqueous solution of ammonia dropwise.
Meu&bgr;doerffer et al, Chemiker Zeitung, 96. Jahrgang (1972) No. 10, 582-583 disclose a method for synthesizing RSO
2
NH
2
where R is perfluoroalkyl.
SUMMARY OF THE INVENTION
The present invention is a composition comprising sulfonyl amide salts, of which at least 50 mol-% of said salts are dimetal sulfonyl amide salts represented by the formula
(RSO
2
NM
b
)
3-b
M′
c
(I)
wherein R is aryl, fluoro-aryl, or XCF
2
— where X is H, halogen, fluorinated or non-fluorinated linear or cyclic alkyl radicals having 1-10 carbon, optionally substituted by one or more ether oxygens, M′ is an alkaline earth metal, b=1 or 2, c=0 or 1, M is alkaline earth or alkali metal when b is 1 or 2 respectively and c=0, and M is alkali metal when b=1 and c=1, with the proviso that c≢1 when b=2.
The present invention further provides for a process for forming a dimetal sulfonyl amide salt comprising:
contacting in an atmosphere having a water vapor concentration of less than 50 parts per million,
at least one alkali or alkaline earth hydride,
a sulfonyl amide or monometal sulfonyl amide salt thereof having the formula
(RSO
2
NH)
3-a
M″ (II)
wherein a=1 or 2, M″ is alkaline earth metal when a=1, M″ is alkali metal or hydrogen when a=2, and R is aryl, fluoro-aryl, or XCF
2
— where X is H, halogen, or a fluorinated or non-fluorinated linear or cyclic alkyl radical having 1-10 carbons, optionally substituted by one or more ether oxygens;
and,
at least one aprotic liquid substantially free of water, thereby forming a reaction mixture; and,
reacting said reaction mixture forming a precipitate of (RSO
2
NM
b
)
3-b
M′
c
;
and separating said precipitate from said liquid.
As used herein, the term “reacting” is intended to mean allowing at least two components in a reaction mixture to react to form at least one product. “Reacting” may optionally include stirring and/or heating or cooling.
REFERENCES:
patent: 5463005 (1995-10-01), Desmarteau
patent: 6252111 (2001-06-01), Sakai et al.
patent: 6319428 (2001-11-01), Michot et al.
Von Johann N. Meubdoerffer, et al. Bisperfluoralkansulfonylimide, Chemiker Zeitung, (19872) pp. 582-583, vol. 96.
Behrend, et al. Trifluormethyl-Schwefel-stickstoff-verbindungen, Journal of Fluorine Chemistry, (1974) pp. 99-106, vol. 4.
E.I. du Pont de Nemours and Company
O'Sullivan Peter
LandOfFree
Method for preparing dimetal sulfonyl amide salts does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method for preparing dimetal sulfonyl amide salts, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for preparing dimetal sulfonyl amide salts will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3243040