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Method for preparing 1,4-cyclohexanedicarboxylic acid dichloride

A technology of cyclohexanedicarbonyl chloride and cyclohexanedicarboxylic acid is applied in the directions of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as reduction of cis ratio, difficulty in manufacturing, etc., and achieves high ratio Effect

Active Publication Date: 2017-09-12
TORAY FINE CHEMICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is the following problem: as the temperature increases, the cis-isomer is converted to the trans-isomer, and the cis-isomer ratio decreases
[0008] Against the background as described above, 1,4-cyclohexanedicarboxylic acid chloride, which has a low yellow coloring component, contains a small amount of acid gas components, has a high cis ratio, and is liquid at room temperature and is easy to handle industrially, is being sought. is difficult to manufacture

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] The cis-isomer ratio is above 60%, and it is a colorless transparent liquid at room temperature, SO 2 Method for producing 1,4-cyclohexanedicarbonyl chloride with a content of 0.5% or less and a reduction in the cis ratio of the raw material within 5%

[0070] Charge 895kg (5.20kmol) of 1,4-cyclohexanedicarboxylic acid into a 2000L reaction tank equipped with a thermometer, a stirrer, and a condenser, and then charge 1,361kg (11.4kmol) of thionyl chloride. After stirring at 50°C for about 8 hours, a light yellow solution with turbidity was obtained. Then, while controlling the temperature at 45 to 50°C, the pressure was gradually increased while observing the foaming in the tank, and the pressure was reduced to a vacuum degree of 40 Torr to perform a degassing process. After the foaming in the tank had subsided, nitrogen gas was introduced from the bottom valve, thereby passing nitrogen gas into the reaction liquid, keeping the reduced pressure at 47 Torr, and ventilat...

Embodiment 2

[0073] Method for producing 1,4-cyclohexanedicarboxylic acid chloride which is a colorless transparent liquid at 20°C or higher with a cis-isomer ratio of 50% or more

[0074] According to the conditions described in Example 1, 1,4-cyclohexanedicarboxylic acid and thionyl chloride were charged, stirred at 68-70°C for about 8 hours, and a light yellow solution with turbidity was obtained. Then, at 68-70° C., the experiment was carried out in the same manner as in Example 1, and nitrogen gas was flowed for 66 hours. The amount of ventilation of nitrogen gas was performed at 2 L / Hr. Then, thin-film distillation was performed in the same manner as in Example 1 to obtain 998 kg (4.77 kmol) of colorless and transparent 1,4-cyclohexanedicarbonyl chloride.

[0075] As a result of GC analysis, the chemical purity was 99.2%, and the cis-body / trans-body=54.0 / 46.0. The reduction of the cis-body was 19.4. Also, SO 2 The content rate is 0.02%.

Embodiment 3

[0077] Colorless transparent liquid at room temperature, SO 2 Method for producing 1,4-cyclohexanedicarbonyl chloride with a content of 1.0% or less and a reduction in the cis ratio of the raw material within 5%

[0078] According to the conditions described in Example 1, 1,4-cyclohexanedicarboxylic acid and thionyl chloride were charged into a 2000L reaction tank equipped with a thermometer, agitator, and condenser, and stirred at 45-50°C for about 8 hours to obtain Yellow solution with turbidity. Then, the degassing step was implemented under the conditions described in Example 1, and was implemented under the condition that the flow rate of nitrogen gas was 2 L / Hr. Then thin film distillation was carried out according to the conditions described in Example 1 to obtain 995 kg (4.76 kmol) of colorless and transparent 1,4-cyclohexanedicarbonyl chloride.

[0079] According to the results of GC analysis, the chemical purity was 99.3%, and the cis-body / trans-body=72.8 / 27.2. Th...

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PUM

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Abstract

The invention relates to a method for preparing 1,4-cyclohexanedicarboxylic acid dichloride. Provided is 1,4-cyclohexanedicarboxylic acid dichloride containing few acidic gas components and predominantly containing cis isomers, which are industrially easy to handle. A method for preparing 1,4-cyclohexanedicarboxylic acid dichloride includes reacting 1,4-cyclohexanedicarboxylic acid containing at least 60% cis isomers with thionyl chloride. The 1,4-cyclohexanedicarboxylic acid dichloride contains at least 50% cis isomers, and the 1,4-cyclohexanedicarboxylic acid dichloride contains acidic gas in an amount of 1.0% by weight or less.

Description

technical field [0001] The present invention is a method for producing 1,4-cyclohexanedicarbonyl chloride. In particular, there is provided a production method that not only preferentially produces the cis-isomer with a low melting point and is easy to handle industrially, but also suppresses isomerization from the cis-isomer to the trans-isomer during production, and efficiently removes the contained acidity. Impurities. Background technique [0002] 1,4-Cyclohexanedicarbonyl dichloride (1,4-Cyclohexanedicarbonyl dichloride) is an important raw material used as a monomer for synthetic resins, a raw material for resin additives, and a raw material for pharmaceutical intermediates. [0003] There are cis- and trans-isomers in 1,4-cyclohexanedicarboxylic acid chloride. The cis-isomer has a lower melting point than the trans-isomer, and 1,4-cyclohexanedicarbonyl chloride, which has a high ratio of the cis-isomer, becomes a liquid at room temperature and is easy to use as an i...

Claims

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Application Information

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IPC IPC(8): C07C51/60C07C61/09
CPCC07C51/60C07B2200/09C07C61/09C07C51/64C07C2601/14
Inventor 菅原一起西川健
Owner TORAY FINE CHEMICALS CO LTD
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