Method for producing amide compound
View Patent ↗The present invention relates to a method for producing a high purity, high quality amide compound, particularly, lactam. A first embodiment of the present invention is characterized in that an amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in a solution recycled into an oxime-forming step is controlled to an amount of 0.4 mol % or less based on the ketone as a starting material. A second embodiment of the present invention is characterized in that one or more compounds selected from the group consisting of a ketone, an oxime and an amide compound are purified by hydrogenation and/or crystallization for eliminating impurities containing a double bond. A third embodiment of the present invention is characterized in that a content of impurities having a cyclic bridge structure is controlled by using a cycloalkanone purified by recrystallization.
1. A process for producing an amide compound, comprising:
reacting a ketone and hydroxylamine in the presence of an organic solvent to give an oxime (hereinafter, referred to as an oxime-forming step),
conducting Beckmann rearrangement of the oxime using a Beckmann rearrangement catalyst to give an amide compound (hereinafter, referred to as a rearrangement step), and
separating the amide compound thus produced and the solvent, and recycling the separated solvent into the oxime-forming step (hereinafter, referred to as a solvent-recycling step);
wherein an amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in the solvent separated in the solvent-recycling step and recycled into the oxime-forming step is controlled to an amount of 0.4 mol % or less based on the ketone as the starting material,
wherein an amount of each of an aldoxime compound and an amidoxime compound contained in the reaction solution in the oxime-forming step is controlled to an amount of 0.4 mol % or less based on the oxime, and
wherein the amide compound is laurolactam and/or caprolactam, the ketone is cyclododecanone and/or cyclohexanone, and the oxime is cyclododecanone oxime and/or cyclohexanone oxime.
2. The process for producing an amide compound according to claim 1 , wherein the Beckmann rearrangement catalyst contains a halogen atom.
3. The process for producing an amide compound according to claim 1 , wherein the organic solvent is an aromatic hydrocarbon.
4. The process for producing an amide compound according to claim 1 , wherein the ketone is cyclododecanone, the amide compound is laurolactam, and the oxime is cyclododecanone oxime.
5. The process for producing an amide compound according to claim 1 , wherein the rearrangement catalyst is a compound having at least two structures represented by formula (5):
-A-X (5)
wherein A represents C (carbon atom), P, N, S, B or Si and X represents an electron-withdrawing leaving group, wherein A is attached to, in addition to X, one or two or more atoms or groups.
6. The process for producing an amide compound according to claim 1 , wherein the rearrangement catalyst is trichlorotriazine, thionyl chloride, phosphorous trichloride or phosphorous pentachloride.
7. The process for producing an amide compound according to claim 1 , wherein the solvent used in the oxime-forming step and the solvent used in the rearrangement step are the same.
8. The process for producing an amide compound according to claim 7 , wherein the solvent is toluene or xylene.