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Method for producing lactam compound
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A technology of lactam compounds and compounds, which is applied in the field of preparation of lactam compounds, can solve the problems of unfavorable energy and processes, etc.
Inactive Publication Date: 2009-09-30
DAICEL CHEM IND LTD
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Therefore, from the viewpoint of the industrial production method of lactam compounds, this method is unfavorable in terms of energy and process.
Method used
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[0069] [Preparation of Cyclic Oxime Compound]
[0070] If the cyclic oxime compound represented by formula (1) is prepared by, for example, the production method shown below, not only can it be easily and efficiently prepared under mild conditions, but also the reaction for synthesizing the cyclic oxime compound and the The rearrangement of the lactam compound can be carried out in one step, and there is no need to separate and purify the cyclic oxime compound midway, so it is extremely advantageous.
[0071] That is to say, the cyclic oxime compound represented by formula (1) can preferably be prepared by the following method, in the presence of a nitrogen-atom-containing cyclic compound containing a skeleton represented by the following formula (6) as a constituent part of the ring, making The cycloalkane corresponding to the cyclic oxime compound represented by formula (1) reacts with nitrite or nitrite.
[0072] [chemical formula 7]
[0073]
[0074] (In the formula, ...
Embodiment 1
[0090] Cyclododecanone oxime (10 mmol), 2,4,6-trichloro-1,3,5-triazine (2 mol%), and toluene (8 mL) were added to the reactor, and stirred at 80° C. for 2 hours. After the reaction, analysis by gas chromatography revealed that the yield of laurolactam was 95%.
Embodiment 2
[0092] Add cyclododecanone oxime (10mmol), 2,4,6-trichloro-1,3,5-triazine (2 mole %), cyclododecane (8g) to the reactor, stir at 80°C 2 hours. After the reaction, analysis by gas chromatography revealed that the yield of laurolactam was 96%.
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Abstract
The present invention discloses a method for commercially efficiently producing a lactam compound having 8-15 carbon atoms at low cost, wherein a rearrangement reaction of a cyclic oxime compound is caused to proceed without producing much by-products such as ammonium sulfate. Specifically disclosed is a method for producing a lactam compound, which is characterized in that a lactam compound represented by the formula (2) below is produced by rearranging a cyclic oxime compound represented by the formula (1) below in a nonpolar solvent B in the presence of an aromatic compound A wherein a leaving group is bonded to a carbon atom constituting the aromatic ring,and a heteroatom or a carbon atom bonded with an electron-withdrawing group is contained as an atom constituting the aromatic ring. (In the formula (1), m represents an integer of 7-14.) (In the formula (2), m is as defined above).
Description
technical field [0001] The present invention relates to a method for producing a lactam compound having 8 to 15 carbon atoms, which is useful as a raw material for medicines, agricultural chemicals, dyes, polyamides, and the like. More specifically, the present invention relates to a method for preparing corresponding lactam compounds by rearrangement reaction of cyclic oxime compounds with 8-15 carbon atoms. Background technique [0002] The technology of preparing corresponding lactams from cyclic oxime compounds by so-called Beckmann rearrangement is very important in industry. Conventionally, for this type of production, a method in which oleum of stoichiometric equivalent or more is used acts, but the problem is the handling of a large amount of ammonium sulfate produced by side reactions. [0003] In view of this problem, a method is disclosed in which an aromatic compound having at least one carbon atom having a leaving group is used as a Beckmann rearrangement catal...
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