Method for producing imide compound
Disclosed is a method for producing “a salt or a complex comprising imide and an organic base”, characterized by reacting halogenated sulfuryl or halogenated phosphoryl with ammonia in the presence of an organic base. According to this method, a target imide compound can be produced in a high yield while significantly suppressing the production of by-products. Further, by reacting the obtained imide compound with an alkali metal hydroxide or an alkaline earth metal hydroxide, an imide metal salt can be easily derived.
1. A method for producing a salt or a complex comprising imide and an organic base represented by the formula [1]
where R represents a halosulfonyl group (—SO 2 X 1 where X 1 is a halogen) or dihalophosphoryl group (—POX 2 X 3 where X 2 and X 3 are identical or different halogens) and B represents an organic base, comprising the step of:
reacting a dihalogenated sulfuryl (SO 2 X 4 X 5 where X 4 and X 5 represent identical or different halogens and identical to or different from the above-mentioned X 1 ) or halogenated phosphoryl (P(═O)X 6 X 7 X 8 where X 6 , X 7 and X 8 represent identical or different halogens and identical to or different from the above-mentioned X 2 or X 3 ) with ammonia in the presence of an organic base,
wherein the ammonia is brought into the reaction after the organic base and the dihalogenated sulfuryl or the halogenated phosphoryl are made firstly coexistent in the reaction system.
2. A method for producing a salt or a complex comprising imide and an organic base represented by the formula [1]
where R represents a halosulfonyl group (—SO 2 X 1 where X 1 is a halogen) or dihalophosphoryl group (—POX 2 X 3 where X 2 and X 3 are identical or different halogens) and B represents an organic base, comprising the step of:
reacting a dihalogenated sulfuryl (SO 2 X 4 X 5 where X 4 and X 5 represent identical or different halogens and identical to or different from the above-mentioned X 1 ) with ammonia in the presence of an organic base,
wherein the ammonia is brought into the reaction after the organic base and the dihalogenated sulfuryl are made firstly coexistent in the reaction system.
3. A method as claimed in claim 1 , wherein the organic base is a tertiary amine represented by the formula [2]
where R 1 , R 2 and R 3 are identical or different and represent a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, or an aryl group (a part or all of hydrogen atoms of the aryl group may be substituted with halogen, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, amino group, nitro group, acetyl group, cyano group or hydroxyl group),
a nitrogen-containing heteroaromatic compound, or
a compound having an imine framework as follows:
—C═N—C—.
4. A method as claimed in claim 1 , wherein the organic base is trimethylamine, triethylamine, diisopropylethylamine, tri-n-propylamine, tributylamine or pyridine.
5. A method as claimed in claim 1 , wherein the organic base is in an amount of 1 to 50 moles relative to 1 mole of ammonia.
6. A method as claimed in claim 1 , wherein the dihalogenated sulfuryl or halogenated phosphoryl is used in an amount of 1 to 10 moles relative to 1 mole of ammonia.
7. A method as claimed in claim 1 , wherein the dihalogenated sulfuryl or halogenated phosphoryl is reacted with ammonia in the presence of the organic base at a reaction temperature of −50 to 150° C.
8. A method for producing an imide metal salt represented by the formula [3]
where R represents a halosulfonyl group (—SO 2 X 1 where X 1 is a halogen) or dihalophosphoryl group (—POX 2 X 3 where X 2 and X 3 are identical or different halogens) M represents an alkali metal or alkaline earth metal, and n represents an integer identical to the valence of the metal, comprising the steps of:
(a) reacting a dihalogenated sulfuryl (SO 2 X 4 X 5 where X 4 and X 5 represent identical or different halogens and identical to or different from the above-mentioned X 1 ) or halogenated phosphoryl (P(═O)X 6 X 7 X 8 where X 6 , X 7 and X 8 represent identical or different halogens and identical to or different from the above-mentioned X 2 or X 3 ) with ammonia in the presence of an organic base,
wherein the ammonia is brought into the reaction after the organic base and the dihalogenated sulfuryl or the halogenated phosphoryl are made firstly coexistent in the reaction system, thereby producing a salt or a complex comprising imide and an organic base represented by the formula [1]
where B represents the organic base; and
(b) reacting the salt or the complex comprising imide and the organic base with a hydroxide or carbonate of alkali metal or a hydroxide or carbonate of alkaline earth metal.