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Preparation method of epsilon-caprolactam

A technology of caprolactam and cyclohexanone oxime, which is applied in the field of purification and preparation of ε-caprolactam, can solve the problem that crude ε-caprolactam cannot be processed economically for a long time, and achieve the effects of small load, extended life and high product yield

Inactive Publication Date: 2005-09-28
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a result, crude ε-caprolactam cannot be treated economically for a long period of time by the hydrogenation process
[0015] According to the above description, when considering the ease of process operation and cost, traditional purification methods such as rectification, crystallization, extraction, ion exchange and hydrogenation, etc. cannot always satisfactorily obtain ε-caprolactam with industrially required purity.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] In a fluidized bed reactor equipped with a high silica content zeolite catalyst, a mixed liquid of cyclohexanone oxime, methanol and water (weight ratio is 1:1.8:0.052) is introduced together with the nitrogen passing through the evaporator. The Beckmann rearrangement was carried out at a reaction temperature of ℃, and the residence time was 8sec. The reaction gas is cooled and condensed to obtain a reaction mixture containing ε-caprolactam.

[0075] The reaction mixture was distilled to remove methanol, low-boiling impurities and high-boiling impurities to obtain crude ε-caprolactam with a purity of 98.97%. According to gas chromatography analysis, the content of cyclohexanone oxime was 584 ppm, the content of MTHI was 604 ppm, and the content of OHP was The content is 355ppm.

[0076]In a 200L reactor, add the crude ε-caprolactam (31.28kg) obtained after rectification and the mixed solvent of cyclohexane and n-heptane (weight ratio 1:3) (46.92kg), and heat to 70℃ The ε-ca...

Embodiment 2

[0081] The cyclohexanone oxime was subjected to Beckmann rearrangement, and the obtained crude ε-caprolactam was distilled in the same manner as in Example 1. The purity of the obtained crude ε-caprolactam was 99.20%. According to gas chromatography analysis, it contained 1736 ppm of cyclohexane. Ketone oxime, 300 ppm MTHI and 248 ppm OHP.

[0082] The obtained crude ε-caprolactam (50 g) was dissolved in a mixed solvent of cyclohexane and n-heptane (weight ratio 1:3) (75 g), and the resulting solution was cooled while stirring to crystallize ε-caprolactam. The crystalline ε-caprolactam was collected by a centrifugal separator, and the collected crystal ε-caprolactam was washed with the cyclohexane and n-heptane mixed solvent (25 g) used above to obtain ε-caprolactam crystals (46.32 g). The yield was 92.63%. The crystalline ε-caprolactam was analyzed as described above. As a result, the contents of cyclohexanone oxime, MTHI and OHP were all lower than the detection limit, the conte...

Embodiment 3

[0086] The cyclohexanone oxime was subjected to Beckmann rearrangement, and the crude ε-caprolactam was distilled in the same manner as in Example 1. The purity of the obtained crude ε-caprolactam was 99.08%. According to gas chromatography analysis, it contained 188 ppm of cyclohexanone oxime, 469ppm MTHI and 205ppm OHP.

[0087] The heptane (82.5 g) was heated into the distilled ε-caprolactam (55 g) and the resulting solution was kept at 70°C. Additional heptane (82.5 g) was cooled with ice.

[0088] Then, a mixture of ε-caprolactam and heptane maintained at 70°C and ice-cooled heptane were simultaneously added dropwise within 10 minutes into a flask maintained at 58°C to precipitate ε-caprolactam. After 30 minutes, the precipitated ε-caprolactam crystals were collected with a centrifugal collector, and the collected ε-caprolactam was washed with heptane (27.5g) to obtain ε-caprolactam crystals (34.76g). The yield was 63.2%. The obtained crystal ε-caprolactam was analyzed as des...

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Abstract

A high purity epsi-caprolactam is prepared by crystallizing an epsi-caprolactam from a hydrocarbon solution containing a crude epsi-caprolactam, and allowing the crystallized epsi-caprolactam in contact with hydrogen in the presence of a hydrogenation catalyst. This process can effectively remove impurities from a crude epsi-caprolactam, which is obtained by subjecting cyclohexanone oxime to the Beckmann rearrangement, and provide a high purity epsi-caprolactam.

Description

Technical field [0001] The invention relates to a purification and preparation method of ε-caprolactam. More specifically, the method for purification and preparation of ε-caprolactam involved in the present invention includes crystallization from a hydrocarbon solution containing crude ε-caprolactam obtained by any reaction, such as cyclohexanone oxime obtained by Beckmann rearrangement. There is a step of contacting ε-caprolactam with hydrogen in the presence of a hydrogenation catalyst. Background technique [0002] As an intermediate for preparing polyamides such as nylon 6, ε-caprolactam is an important compound, and many methods for preparing ε-caprolactam are known. For example, the Beckmann rearrangement of cyclohexanone oxime in the presence of acidic media such as oleum can produce ε-caprolactam industrially. However, this method has disadvantages such as producing a large amount of low-value by-product ammonium sulfate. [0003] As a method that ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D201/16
CPCC07D201/16C07D227/087
Inventor 深尾正美高峰宽
Owner SUMITOMO CHEM CO LTD