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Cyclododecanone and method for producing same

A technology for cyclododecanone and its manufacturing method, which is applied in the field of cyclododecanone and its manufacturing, can solve the problems of unfavorable laurolactam, etc., and achieve the effects of easy commercial mass production, prevention of explosive reaction, and control of reaction heat

Pending Publication Date: 2022-05-27
HANWHA SOLUTIONS CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, according to the above-mentioned production method of cyclododecanone, there is a problem that a large amount of by-products (for example, cyclododecanol, cyclododecanediol, etc.) are produced
[0004] Therefore, the problems of the above-mentioned prior art have a negative impact on the construction of the entire process system for the manufacture of laurolactam, so it is still necessary to conduct research to find a more effective method

Method used

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  • Cyclododecanone and method for producing same
  • Cyclododecanone and method for producing same
  • Cyclododecanone and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0117] Step 1. Manufacturing method of cyclodecane oxide

[0118]

[0119] In a high-speed stirring batch (100 ml) reactor, add 25 g of cyclodecene, 0.075 g of H 2 WO 4 , H of 0.06g 3 PO 4 , 0.105g tri-n-octyl amine, 1.4g H 2 O, 1.02g of 50wt%H 2 O 2 。 Then, the reaction was performed at 80 °C for a total of 4 h. During the above reaction, while stirring the reactor contents at 1500 rpm, 85 μl of hydrogen peroxide per minute (50 wt% aqueous solution) is further injected by a pump.

[0120] According to the above manufacturing method, the conversion of cyclodecene is 98.8%, and the selectivity is 99.9%.

[0121] Step 2. Manufacturing method of cyclodecone

[0122]

[0123] Using a glove box (Glovebox), under inactive conditions (inert condition), in a 50 ml round bottom flask was added in the reaction mixture containing cyclodecadecane epoxide obtained in step 1 above 5g, lithium bromide (LiBr) 0.085g. Then, after making a nitrogen balloon and attaching it to a flask, it is pl...

Embodiment 2 to Embodiment 6

[0128] As shown in Table 1 below, the amount and pattern of addition of hydrogen peroxide are adjusted, and each reaction is carried out by a method similar to the above example 1.

[0129] The results, the conversion rate and selectivity of each step are shown in Table 2 below.

[0130] 【Table 1】

[0131]

[0132] 【Table 2】

[0133]

Embodiment 7

[0134] (Example 7) Step 1. Manufacturing method of cyclodecane epoxide

[0135] In the high-speed stirring batch (Batch) reactor (100ml), add 25g of cyclodecene, 0.1g of Na 2 WO 4 , H of 0.06g 3 PO 4 , 0.12g of Aliquat336 (cognis), 1.4g of H 2O, 1.02g of 50wt%H 2 O 2 。 Then, the reaction was performed at 80 °C for a total of 4 h. During the above reaction, while stirring the reactor contents at 1500 rpm, further inject 85 μl of hydrogen peroxide per minute by pump.

[0136] The conversion of cyclodecadecane according to the above manufacturing method is 96.0%, and the selectivity is 98.1%.

[0137] Step 2. Manufacturing method of cyclodecone

[0138] Using the reaction mixture containing cyclodecdodecane epoxide obtained in step 1 above, the reaction was carried out by the same method as step 2 of the above example 1.

[0139] Step 3. Purification method of cyclodecone

[0140] The reaction was carried out by the same method as step 3 of the above embodiment 1.

[0141] Accordi...

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Abstract

The present invention relates to cyclododecanone and a method for producing the same, and according to the present invention, it is possible to provide a method for producing cyclododecanone capable of achieving a high conversion rate and minimizing the generation of unreacted materials and reaction by-products. Furthermore, the present invention achieves a high conversion rate and selectivity despite having a simplified process configuration, and thus can be usefully applied to an economical method for producing laurolactam, which is easy to commercially mass-produce. According to the present invention, the proportion of cyclododecanol, cyclododecanediol and the like obtained as reaction by-products in the final product can be significantly reduced, and cyclododecanone can be produced with a high conversion rate.

Description

Technical field [0001] The present invention relates to cyclodecyl ketones and manufacturing methods thereof. Background [0002] Cyclodecone (CDON, cyclododecanone) is used in the manufacture of laurolactam (laurolactam), which is an organic compound used as a monomer used in the manufacture of one of the engineering plastics polyamide (e.g., nylon-12, nylon 6-12, etc.). [0003] The manufacture of cyclodecagon can usually begin with cyclodecyltriene (CDT, cyclododecatriene). Specifically, cyclododecene (CDEN) is produced by selective hydrogenation in cyclodecene, and cyclododecene is made by oxidation. However, according to the above-described manufacturing methods of cyclodecones, having the problem of producing a large number of by-products (e.g., cyclodecanool, cyclodecanediol, etc.). [0004] Therefore, the problems of the above prior art have a negative impact on the construction of the entire process system for the manufacture of laurectam, so it is still necessary to exp...

Claims

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Application Information

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IPC IPC(8): C07C45/58C07C49/413C07C45/80C07C45/86C07D301/12C07D303/04B01J31/34
CPCC07C45/58C07D303/04C07D301/12B01J23/30B01J27/16B01J31/0237B01J31/34C07C45/80C07C45/86C07C2601/20B01J35/19C07C49/413B01J31/0239
Inventor 金芝娟徐玄张南镇
Owner HANWHA SOLUTIONS CORP
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