U.S. patent application number 09/773648 was filed with the patent office on 2001-09-13 for process for producing sulfonylimide compound.
Invention is credited to Sakamoto, Yoshitaka, Yonezawa, Tetsuo.
Application Number | 20010021790 09/773648 |
Document ID | / |
Family ID | 26584465 |
Filed Date | 2001-09-13 |
United States Patent
Application |
20010021790 |
Kind Code |
A1 |
Yonezawa, Tetsuo ; et
al. |
September 13, 2001 |
Process for producing sulfonylimide compound
Abstract
A process for producing sulfonylimide compound is represented by
the formula (I) MN(SO.sub.2R.sub.f.sup.1) (SO.sub.2R.sub.f.sup.2)
industrially easily at a low cost in an efficient manner comprising
reactions of at least one sulfonyl halogenides represented by the
formula (II) R.sub.fSO.sub.2X with anhydrous ammonia or an ammonium
salt in the presence of a fluorine compound represented by the
formula (III) MF, in which X represents either F or Cl among
halogen elements of VIIb group in the periodic table, and M
represents any one of Li, Na, K and Cs among alkali metals of group
Ia in the periodic table, R.sub.f.sup.1 and R.sub.f.sup.2, which
may be the same or different, respectively represent any one of a
straight chain or branched compound of a fluoroalkyl,
perfluoroalkyl, fluoroallyl or fluoroalkenyl group having 1 to 12
carbon atoms, and R.sub.f in the formula (II) represents the same
group as R.sub.f.sup.1 or R.sub.f.sup.2 in the formula (I).
Inventors: |
Yonezawa, Tetsuo; (Osaka,
JP) ; Sakamoto, Yoshitaka; (Osaka, JP) |
Correspondence
Address: |
KODA & ANDROLIA
Suite 3850
2029 Century Park East
Los Angeles
CA
90067-3024
US
|
Family ID: |
26584465 |
Appl. No.: |
09/773648 |
Filed: |
January 31, 2001 |
Current U.S.
Class: |
564/80 |
Current CPC
Class: |
C07C 303/38 20130101;
C07C 311/48 20130101; C07C 303/38 20130101 |
Class at
Publication: |
564/80 |
International
Class: |
C07C 311/03 |
Foreign Application Data
Date |
Code |
Application Number |
Jan 31, 2000 |
JP |
2000-021578 |
Claims
What is claimed is:
1. A process for producing a sulfonylimide compound represented by
the formula (I): MN (SO.sub.2R.sub.f.sup.1)(SO.sub.2R.sub.f.sup.2),
wherein M represents any one of Li, Na, K and Cs among alkali
metals of group Ia in the periodic table, R.sub.f.sup.1 and
R.sub.f.sup.2, which are the same or different and respectively
represent any one of a straight chain or branched compound of a
fluoroalkyl, perfluoroaklyl, fluoroallyl or fluoroalkenyl group
having 1 to 12 carbon atoms, wherein the process reacts: at least
one of sulfonyl halogenides represented by the formula (II):
R.sub.fSO.sub.2X, wherein R.sub.f represents the same or identical
group as R.sub.f.sup.1 or R.sub.f.sup.2 in the formula (I), and X
represents either F or Cl among halogen elements of VIIb group in
the periodic table, with anhydrous ammonia or an ammonium salt, and
with a fluorine compound represented by the Formula (II): MF,
wherein M represents any one of Li, Na, K and Cs among alkali
metals of group Ia in the periodic table.
2. A process for producing a sulfonylimide compound represented by
the formula (I): MN (SO.sub.2R.sub.f.sup.1)(SO.sub.2R.sub.f.sup.2)
wherein M represents any one of Li, Na, K and Cs among alkali
metals of group Ia in the periodic table, R.sub.f.sup.1 and
R.sub.f.sup.2, which are the same or different and respectively
represent any one of a straight chain or branched compound of a
fluoroalkyl, perfluoroaklyl, fluoroallyl or fluoroalkenyl group
having 1 to 12 carbon atoms, wherein the process reacts: a
sulfonylamide represented by the formula (IV):
R.sub.fSO.sub.2NH.sub.2, wherein R.sub.f represents the same group
as R.sub.f.sup.1 or R.sub.f.sup.2 in the formula (I), with at least
one of sulfonyl halogenides represented by the formula (II):
R.sub.fSO.sub.2X, wherein R.sub.f represents the same or identical
group as R.sub.f.sup.1 or R.sub.f.sup.2 in the formula (I), and X
represents either F or Cl among halogen elements of VIIb group in
the element periodic table, and with a fluorine compound
represented by the formula (III): MF, wherein M represents any one
of Li, Na, K and Cs among alkali metals of group Ia in the periodic
table.
3. The process for producing a sulfonylimide compound according to
claim 1, wherein an ammonium fluoride or an ammonium
hydrogendifluoride is used as the ammonium salt.
Description
BACKGROUND OF THE INVENTION
[0001] 1. Technical field of the Invention
[0002] The present invention relates to a process for producing a
sulfonylimide compound represented by the formula:
MN(SO.sub.2R.sub.f.sup.1)(SO.sub.2R.sub.f.sup.2)
[0003] 2. Description of Prior Art
[0004] Sulfonylimide compounds are safe as a solute of a battery
electrolyte and battery electrolyte that uses the sulfonylimide
compound as a solute has a high energy density and exhibits high
conductivity. Hence, the sulfonylimide compounds are regarded as a
promising solute of a battery electrolyte. Also, the sulfonylimide
compounds are useful as a Lewis acid catalyst and an ionic
conduction agent.
[0005] The sulfonylimide compounds represented by the formula (I)
MN(SO.sub.2R.sub.f.sup.1)(SO.sub.2R.sub.f.sup.2) may be synthesized
by the process proposed by D. D. Desmarteau et al. in INORGANIC
CHEMISTORY VOL. 23, No. 23, P3720-3723 (1984).
[0006] In this synthetic method, as shown by the following formula,
trifluoromethylsulfonyl fluoride is reacted with ammonium, the
resulting product is treated using hydrochloric acid to produce
trifluoromethylsulfonylamide, which is then reacted with sodium
methylate and then with hexamethyldisilazane, and the resulting
product is reacted with trifluoromethylsulfonyl fluoride, thus
obtaining an imide sodium salt. 1
[0007] However, this process involves multi-reaction steps and
hence takes longer. Also, expensive hexamethyldisilazane must be
used to obtain an intermediate, and the yield is as low as about
50%.
[0008] In the above-described formula (I), M represents any one of
Li, Na, K and Cs among alkali metals of group Ia in the periodic
table. R.sub.f.sup.1 and R.sub.f.sup.2, which may be the same or
different, respectively represent any one of a straight chain or
branched compound of a fluoroalkyl, perfluoroalkyl, fluoroallyl and
fluoroalkenyl group having 1 to 12 carbon atoms (the same
hereafter).
[0009] In the Japanese Patent Application National Publication No.
Hei3-501860, a method is disclosed in which a silazane metal
compound is reacted with a perfluorosulfonyl halide compound to
obtain an imide compound. In the Japanese Patent Application
National Publication No. Hei4-501118, a method is disclosed in
which an ionic nitride is reacted with a halogenated sulfonic acid
to obtain in imide compound.
[0010] However, the silazane metal compound and the ionic nitride
used in each of the above prior art are expensive, and hence the
above methods are not an economical production method.
[0011] Also, in the Japanese Patent Application Laid-Open(Kokai)
No. Hei8-81436, a method is disclosed in which anhydrous ammonia or
a sulfonylamide and a sulfonyl fluoride are reacted with a tertiary
amine or a heterocyclic amine, and the reaction product is further
reacted with, for instance, a hydroxide containing an alkali metal
and an alkali earth metal to produce imide salts.
[0012] In this method, because the product in the first stage is
generated as an amine salt, it must be further reacted with an
inorganic salt. Also, since a tertiary amine or a heterocyclic
amine is used in the reaction, problems concerning work environment
caused by the odor and disposal of the amine occur. Moreover,
because the anhydrous ammonia is always used, an autoclave as the
reactor and a low temperature cooling unit are required. This
method is, therefore, unsuitable for mass-production.
[0013] As outlined above, the prior art involves a long reaction
step and uses expensive raw materials, and it is hence hard to say
that these methods in prior art are industrially acceptable
methods.
[0014] In the Japanese Patent Application Laid-Open (Kokai) No.
Hei8-81436, anhydrous ammonia, a perfluoroalkylsulfonyl fluoride
and a tertiary amine are reacted with each other. To obtain an
imide salt, at least two steps are required; and in the reaction, a
tertiary amine or a heterocyclic amine is used, causing possibility
of pollution of work environment derived from the odor and the
like. Further, the product must be reacted with an alkali metal or
the like in an aqueous solution in the second step, and at this
time, it is necessary to dispose the amine which is freed and
distilled together with water, causing increased production
costs.
SUMMARY OF THE INVENTION
[0015] It is an object of the present invention to solve these
various problems and to produce a sulfonylimide compound
industrially easily at a low cost in an efficient manner.
[0016] The inventors of the present application have made earnest
studies to accomplish the above object and as a result found that a
sulfonylimide compound (represented by the formula (I)
MN(SO.sub.2R.sub.f.sup.1) (SO.sub.2R.sub.f.sup.2)) which is free
from the foregoing problems can be produced industrially easily at
a low cost in an efficient manner.
[0017] More specifically, the present invention comprises a
reaction of at least one of the sulfonyl halogenides represented by
the formula (II) R.sub.fSO.sub.2X with anhydrous ammonium or an
ammonium salt in the presence of fluorine compounds represented by
the formula (III) MF.
[0018] In the above-described formulas (I) and (II), M represents
any one of Li, Na, K and Cs among alkali metals of group Ia in the
periodic table, and X represents either F or Cl among halogen
elements of VIIb group in the periodic table. Also, R.sub.f in the
above-described formula (II) represents the same or identical group
as R.sub.f.sup.1 or R.sub.f.sup.2 in the formula (I).
[0019] The inventors have also found that sulfonylimide compound
represented by the formula (I) MN(SO.sub.2R.sub.f.sup.1)
(SO.sub.2R.sub.f.sup.2) can be produced in the mild conditions that
anhydrous ammonium is not always used and in only one-step reaction
by reacting a sulfonylamide represented by the formula (IV)
R.sub.fSO.sub.2NH.sub.2, at least one of the sulfonyl halogenides
represented by the formula (II) R.sub.fSO.sub.2X, and fluorine
compound represented by the formula (III)MF with each other.
[0020] Li, Na, K, Rb, Cs and Fr exist as the alkali metals of Ia
group in the periodic table. Among these metals, especially any one
of Li, Na, K and Cs is selected and used. Therefore, in the case of
these metals, the fluorine compounds that are used are LiF, NaF, KF
(as KF, any one of calcine-dried KF (cd KF) and spray-dried KF (sd
KF) produced by a spray drying method may be used) and CsF
[0021] The reason why Li, Na, K, and Cs are preferred among alkali
metals of group Ia in the periodic table is that they are
relatively cheap and suitable to produce sulfonylimide compounds
industrially easily, at a low cost and in an efficient manner.
Especially, K is prominent for the above property among Li, Na, K,
and Cs.
[0022] In the present invention, on the other hand, the
sulfonylimide compound can be produced by using an ammonium salt.
As the ammonium salt in this case, it is desirable to use ammonium
fluoride or ammonium hydrogendifluoride. These of either one of
these compounds has the advantage that a specific reactor
(autoclave) is not required.
[0023] CF.sub.3SO.sub.2Cl among sulfonyl halogenides represented by
the formula (II) R.sub.fSO.sub.2X, which is sold on the market as a
reagent, can be usually handled as liquid because its boiling point
is 30.degree. C., relatively high among these kinds of
compounds.
[0024] Although "sulfonylimide" and "sulfonylamide" in the present
specification should be expressed formally as "sulfonimide" and
"sulfonamide", respectively, both are handled as the same
significance.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0025] The embodiment of the present invention will be hereinafter
explained in detail.
[0026] The object compounds which has been produced in multi-steps
in the prior art can be produced in one step by introducing a
fluorine compound represented by the formula (III) MF, at least one
of the sulfonyl halogenides represented by the formula (II)
R.sub.fSO.sub.2X, and anhydrous ammonia or an ammonium salt into an
inert solvent and reacting the mixture as shown by the following
formula 2, 3, 4, and 5.
[0027] This is due to the basicity of the fluorine compound
represented by the formula (III) MF.
[0028] (1) In the case where R.sub.f.sup.1 and R.sub.f.sup.2 in the
formula (I) MN(SO.sub.2R.sub.f.sup.1) (SO.sub.2R.sub.f.sup.2) are
the same or equal to each other:
NH.sub.3+2R.sub.fSO.sub.2X+6MF.fwdarw.MN(SO.sub.2R.sub.f).sub.2+3MFHF+2MX
Reaction Formula 2
[0029] One mol of anhydrous ammonium, 2 mol of at least one of the
sulfonyl halogenides represented by the formula (II)
R.sub.fSO.sub.2X and 6 mol of a fluorine compound represented by
the formula (III) MF are introduced into a reactor and the mixture
is reacted in a solvent.
[0030] After completion of the reaction, 2 mol of the by-produced
MX and 3 moles of hydrogendifluoride salt MFHF are removed by
filtration, and the filtrate is concentrated. The sulfonylimide
compound represented by the formula (I) MN(SO.sub.2R.sub.f).sub.2
can be thereby produced.
[0031] (2) In the case where R.sub.f.sup.1 and R.sub.f.sup.2 in the
formula (I) MN(SO.sub.2R.sub.f.sup.1)(SO.sub.2R.sub.f.sup.2) are
different from each other:
[0032] A sulfonylamide containing the R.sub.f.sup.1 group which is
produced by a known process shown below is reacted with at least
one of the sulfonyl halogenides having a desired R.sub.f.sup.2
group. A sulfonylimide compound with the R.sub.f.sup.1 group and
the R.sub.f.sup.2 group are respectively constituted of an
objective group can be thereby produced. 2
[0033] (3) In the case of using an ammonium salt:
(R.sub.f.sup.1SO.sub.2X)(R.sub.f.sup.2SO.sub.2X)+7MF+NH.sub.4F.fwdarw.MN(S-
O.sub.2R.sub.f.sup.1)(SO.sub.2R.sub.f.sup.2)+4MFHF+2MX Reaction
Formula 5
[0034] wherein R.sub.f.sup.1 and R.sub.f.sup.2 are the same or
different.
[0035] One mol of an ammonium salt, 2 mol of at least one of the
sulfonyl halogenides represented by the formula (II)
R.sub.fSO.sub.2X and 7 mol of a fluorine compound represented by
the formula (III) MF are introduced into a reactor, and the mixture
is reacted in a solvent.
[0036] After completion of the reaction, 2 mol of the by-produced
MX and 4 mol of the by-produced hydrogendifluoride MFHF are removed
by filtration, and then the filtrate is concentrated. The
sulfonylimide compound represented by the formula (I)
MN(SO.sub.2R.sub.f.sup.1) (SO.sub.2R.sub.f.sup.2) can be thereby
produced.
[0037] These reactions can occur in a temperature range between
about -30.degree. C. and 200.degree. C. At a temperature less than
this range, the reaction rate is very low whereas at the
temperature exceeding the above range, decomposition of the
compounds, solvent and product to be used arises. A more preferable
temperature range for the reactions is between 0.degree. C. and
100.degree. C.
[0038] As to the solvent, any solvent can be used without
particular limitations as far as it is inert to the reaction
materials. For example, ethers such as diethyl ether and
tetrahydrofuran, halogenated hydrocarbons such as dichloromethane
and dichloroethane, hydrocarbons such as benzene, heptane and
hexane and nitrites such as acetonitrile can be used.
[0039] In order to produce various sulfonylimide compounds other
than those described above, a sulfonylimide compound obtained by
these production methods is made into an acid by using concentrated
sulfuric acid and the acid is distilled to thereby synthesize a
sulfonylimidic acid
[HN(SO.sub.2R.sub.f.sup.1)(SO.sub.2R.sub.f.sup.2)]. This acid can
be further reacted with a compound selected from hydroxides,
oxides, carbonates and acetates of metals corresponding to this
acid.
[0040] In this case, fluorine compounds represented by the formula
(III) MF to be used in the synthesis of a sulfonylimide compound
can be compounded and used.
EXAMPLES
[0041] The present invention will be described in more detail by
way of examples, which, of course, do not limit the present
invention.
Example 1
[0042] A flask with four necks was charged with 150 ml of
acetonitrile, 23.4 g of potassium fluoride and 20 g of
trifluoromethylsulfonylamide CF.sub.3SO.sub.2NH.sub.2. The reactor
was soaked in a 40.degree. C. hot water bath, and 25.1 g of
trifluoromethylsulfonyl fluoride CF.sub.3SO.sub.2F was introduced
with sufficient stirring. The reaction solution was subjected to
filtration, and the filtrate was concentrated under reduced
pressure to obtain potassium bistrifluoromethylsulfonylimid- e
KN(SO.sub.2CF.sub.3).sub.2 in an amount of 42.7 g. The yield was
99%.
[0043] Next, 42.7 g of this potassium
bistrifluoromethylsulfonylimide was added in a flask that was
charged with 60 ml of concentrated sulfuric acid, and the mixture
was dissolved under heat. Under reduced pressure, 34.6 g of
bistrifluoromethylsulfonylimidic acid HN(SO.sub.2CF.sub.3).sub.- 2
was distilled by distillation. The yield was 92%.
[0044] Then, 34.6 g of the resulting
bistrifluoromethylsulfonylimidic acid was dissolved in pure water
and reacted with 4.5 g of lithium carbonate. Excess lithium
carbonate was removed by filtration, and the filtrate was
concentrated to obtain 34.6 g of lithium
bistrifluoromethylsulfonylimide LiN(SO.sub.2CF.sub.3).sub.2. The
yield was 98%.
Example 2
[0045] An autoclave made of stainless was charged with 200 ml of
acetonitrile and 68.3 g of potassium fluoride. The reactor was
cooled to -60.degree. C. in a dry ice/methanol bath, and 5 g of
anhydrous ammonia was introduced.
[0046] In succession, 90.0 g of trifluoromethylsulfonyl fluoride
CF.sub.3SO.sub.2F was introduced, and the temperature of the
mixture was returned to ambient temperature with sufficient
stirring. After that, the reactor was soaked in a 40.degree. C. hot
water bath, and the reaction was completed while stirring
sufficiently. The reaction solution was subjected to filtration,
and the filtrate was concentrated under reduced pressure to obtain
88.2 g of potassium bistrifluoromethylsulfonylimide
KN(SO.sub.2CF.sub.3).sub.2. The yield was 95%.
Example 3
[0047] A flask with four necks was charged with 1 liter of
methylene chloride, 10 g of ammonium fluoride and 78.4 g of
potassium fluoride. The reactor was soaked in a 40.degree. C. hot
water bath, and 82.1 g of trifluoromethylsulfonyl fluoride
CF.sub.3SO.sub.2F was introduced while stirring sufficiently. The
reaction solution was subjected to filtration, and the filtrate was
concentrated under reduced pressure to obtain 81.5 g of potassium
bistrifluoromethylsulfonylimide KN(SO.sub.2CF.sub.3).sub.2. The
yield was 95%.
Example 4
[0048] A flask was charged with 300 ml of DMF (dimethylformamide),
30 g of perfluorobutylsulfonyl fluoride C.sub.4F.sub.9SO.sub.2F,
15.1 g of trifluoromethylsulfonylamide CF.sub.3SO.sub.2NH.sub.2 and
13 g of sodium fluoride, and the mixure was heated to 100.degree.
C. and sufficiently stirred to react. The reaction solution was
subjected to filtration, and the filtrate was concentrated under
reduced pressure to obtain 35.1 g of sodium
perfluorobutylsulfonyl-trifluoromethylsulfonylimide
NaN(SO.sub.2C.sub.4F.sub.9)(SO.sub.2CF.sub.3). The yield was
78.0%.
Example 5
[0049] A flask with four necks was charged with 200 ml of
acetonitrile, 12 g of perfluorobuthylsulfonyl fluoride
C.sub.4F.sub.9SO.sub.2F, 15.0 g of cesium fluoride, and 0.73 g of
ammonium fluoride, and the mixture was heated 50.degree. C. and
sufficiently stirred to react. The reaction solution was subjected
to filtration, and the filtrate was concentrated under reduced
pressure to obtain 12.5 g of cesium bisperfluorobuthylsulfo-
nylimide CsN(SO.sub.2C.sub.4F.sub.9).sub.2. The yield was
89.3%.
Example 6
[0050] An autoclave made of stainless was charged with 100 ml of
dichloromethane, 100 ml of DMF (dimethylformamide) and 30.5 g of
lithium fluoride. The reactor was cooled to -60.degree. C. in a dry
ice/ methanol bath, and 5 g of anhydrous ammonia was
introduced.
[0051] In succession, 100.0 g of trifluoromethylsulfonyl floride
CF.sub.3SO.sub.2F was introduced, and the temperature of the
mixture was returned to ambient temperature with sufficient
stirring. After that, the reactor was soaked in a 50.degree. C. hot
water bath, and the reaction was run while stirring
sufficiently.
[0052] The reaction solution was subjected to filtration, and the
filtrate was concentrated under reduced pressure, but only 1.7 g of
lithium bistrifluoromethylsulfonylimide LiN(SO.sub.2CF.sub.3).sub.2
was obtained (the yield was 2.0%).
[0053] Although the amount and percentage yield of the product
compound in this case were lower than in the case of other
examples, this case is expected to be improved by further studies.
Such an improved case should be indeed in the scope of the present
invention.
Example 7
[0054] A flask with four necks was charged with 150 ml of
acetonitrile, 31.2 g of potassium fluoride, and 10 g of
trifluoromethylsulfonylamide CF.sub.3SO.sub.2NH.sub.2 were added.
The reactor was soaked in a 40.degree. C. water bath, and 11.3 g of
trifluoromethylsulfonyl chloride CF.sub.3SO.sub.2Cl was introduced
while stirring sufficiently. The reaction solution was subjected to
filtration, and the filtrate was concentrated under reduced
pressure to obtain 21.4 g of potassium
bistrifluoromethylsulfonylimide KN(SO.sub.2CF.sub.3).sub.2. The
yield was 96%.
[0055] In succession, 21.4 g of potassium
bistrifluoromethylsulfonylimide was added in a flask that was
charged with 30 ml of concentrated sulfuric acid, and the mixture
was dissolved under heat. And then, 15.6 g of
bistrifluoromethylsulfonylimidic acid HN(SO.sub.2CF.sub.3).sub.2
was distilled by distillation under reduced pressure. The yield was
83%.
[0056] The resulting 15.6 g of bistrifluoromethylsulfonylimidic
acid was dissolved in the pure water and reacted with 2.1 g of
lithium carbonate. Excess lithium carbonate was subjected to
filtration, and the filtrate was concentrated to obtain 15.4 g of
lithium bistrifluoromethylsulfonylim- ide
LiN(SO.sub.2CF.sub.3).sub.2. The yield was 97%.
Example 8
[0057] A flask with four necks was charged with 200 ml of methylene
chloride, 10 g of ammonium fluoride, and 110 g of potassium
fluoride. The reactor was soaked in a 40.degree. C. water bath, and
91.0 g of trifluoromethylsulfonyl chloride CF.sub.3SO.sub.2Cl was
introduced while stirring sufficiently. The reaction solution was
subjected to filtration, and the filtrate was concentrated under
reduced pressure to obtain 81.0 g of potassium
bistrifluoromethylsulfonylimide KN(SO.sub.2CF.sub.3).sub.2. The
yield was 94%.
Example 9
[0058] A flask with four necks was charged with 5 g of ammonium
fluoride, 143.6 g of cesium fluoride, and 200 ml of
tetrahydrofuran. With sufficiently stirring the reactor, 22.8 g of
trifluoromethylsulfonyl chloride CF.sub.3SO.sub.2Cl was introduced,
and then 27.3 g of pentafluoroethylsulfonyl fluoride
C.sub.2F.sub.5SO.sub.2F was added. The reaction solution was
treated in the same way as Example 2 to obtain 62 g of cesium
perfluoroethylsulfonyl trifluoromethylsulfonylimide
CsN(SO.sub.2C.sub.2F.sub.5) (SO.sub.2CF.sub.3). The yield was
99.2%.
Example 10
[0059] In a SUS (stainless)-made autoclave, 200 ml of methylene
chloride, 300 ml of DMF (dimethylformamide), 45.6 g of lithium
fluoride, and 99.0 g of trifluoromethylsulfonyl chloride
CF.sub.3SO.sub.2Cl were added. The reactor was cooled to
-60.degree. C. in a methanol/dry ice bath, and 5 g of anhydrous
ammonia was introduced.
[0060] The reaction mixture was returned to the room temperature
while stirring sufficiently, and then the reactor was soaked in a
80.degree. C. water bath, and the reaction was run while stirring
sufficiently. Consequently, the reaction solution was treated in
the same way as Example 2, but only 0.8 g of lithium
bistrifluoromethylsulfonylimide LiN(SO.sub.2CF.sub.3).sub.2 was
obtained (the yield was 0.9%). The amount and yield of the product
were considerably lower than the cases of other Examples, however,
further improvement may be expected by the future investigations.
This invention naturally includes such a case.
Example 11
[0061] In a SUS (stainless)-made autoclave, 200 ml of methylene
chloride, 300 ml of DMF (dimethylformamide), 74.1 g of sodium
fluoride, and 49.5 g of trifluoromethylsulfonyl chloride
CF.sub.3SO.sub.2Cl were added. The reactor was cooled to
-60.degree. C. in a methanol/dry ice bath, and 5 g of anhydrous
ammonia was introduced.
[0062] Consequently, 88.8 g of perfluorobuthylsulfonyl fluoride
C.sub.4F.sub.9SO.sub.2F was added, and the reaction mixture was
returned to the room temperature with stirring sufficiently. And
then, the reactor was soaked in a 80.degree. C. water bath, and the
reaction was run while stirring sufficiently. Consequently, the
reaction solution was treated in the same way as Example 2, to
obtain 18 g of sodium perfluorobuthylsulfonyl
trifluoromethylsulfonylimide NaN(SO.sub.2C.sub.4F.sub.9)
(SO.sub.2CF.sub.3). The yield was 13.5%.
[0063] It should be noted that the sulfonylimide compounds obtained
in the above examples were respectively confirmed by identifying
them using an infrared absorption spectrum.
[0064] As seen from the above description, the production process
of the present invention has such an effect that sulfonylimide
compounds useful as lithium battery electrolytes and organic
synthetic catalysts are produced industrially easily at a low cost
in an efficient manner.
[0065] Furthermore, the production process according to the present
invention has such an effect that by reacting a sulfonylamide, a
sulfonyl fluoride and a fluorine compound with each other, a
sulfonylimide compound useful as lithium battery electrolytes and
organic synthtic catalysts is produced under a mild condition that
anhydrous ammonia is not always used, and in one stage. Also, a
specific reactor (autoclave) is not required unlike the case that
uses anhydrous ammonia.
* * * * *