Method for producing N,N'-dimethyl cyclohexanediamine

A technology of dimethylcyclohexanediamine and its production method, which is applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., to achieve the effects of low raw material cost, non-toxic production process and simple process

Inactive Publication Date: 2014-06-18
姜树林
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Literature (Journal of the American Chemical Society, 2002, 124(39):11684-11688) reported a production method of N,N' dimethylcyclohexanediamine, firstly cyclohexanediamine and chloroformate or formate reaction, and then use lithium aluminum hydride to reduce the above-mentioned dangerous goods reactant to obtain the target product. The disadvantages of this method are: the reaction raw materials are expensive, and the strong reducing agent lithium aluminum hydride is highly toxic.

Method used

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  • Method for producing N,N'-dimethyl cyclohexanediamine
  • Method for producing N,N'-dimethyl cyclohexanediamine

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Embodiment 1

[0019] Step 1: Sulfonation of Cyclohexanediamine

[0020] Dissolve 20mmol of 1,2-cyclohexanediamine in 10ml of pyridine, add the above solution dropwise into 10ml of pyridine solution mixed with 40mmol of p-toluenesulfonyl chloride, control the temperature below 60°C during the dropwise addition, when the color of the solution When it changes from colorless to dark red, after dropping, put it at room temperature to react for 7 hours, stop the reaction, add 15% hydrochloric acid to adjust the pH to 6-7, let it stand for 24 hours, filter, and wash the solid with 10ml of water for 3 times, 6.5 g of a white powdery solid were obtained.

[0021] Step 2: Methylation

[0022] Dissolve 7.18mmol of the product of step 1 in 60ml of acetonitrile, add 28.7mmol of potassium carbonate powder, stir at room temperature for 1h, add 28.7mmol of methyl iodide in an ice bath, react in an ice bath for 30min, remove the ice bath and then return to room temperature React for 12 hours, stop the rea...

Embodiment 2

[0026] Step 1: Sulfonation of Cyclohexanediamine

[0027] Dissolve 20mmol of 1,4-cyclohexanediamine in 10ml of pyridine, add the above solution dropwise into 10ml of pyridine solution mixed with 40mmol of p-toluenesulfonyl chloride, control the temperature below 60°C during the dropwise addition, when the color of the solution When it changes from colorless to dark red, after dropping, put it at room temperature to react for 7 hours, stop the reaction, add 15% hydrochloric acid to adjust the pH to 6-7, let it stand for 24 hours, filter, and wash the solid with 10ml of water for 3 times, 7.3 g of a white powdery solid were obtained.

[0028] Step 2: Methylation

[0029] Dissolve 7.18mmol of the product of step 1 in 60ml of acetonitrile, add 28.7mmol of potassium carbonate powder, stir at room temperature for 1h, add 28.7mmol of methyl iodide in an ice bath, react in an ice bath for 30min, remove the ice bath and then return to room temperature React for 12 hours, stop the rea...

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Abstract

The invention discloses a method for producing N,N'-dimethyl cyclohexanediamine, which comprises the following steps of: reacting cyclohexanediamine with aryl benzene sulfonyl chloride to protect the nitrogenous base; implementing a methylation by a methylating reagent; and removing aryl benzenesulfonyl by hydrolysis of sulfuric acid, to obtain the target product N,N'-dimethyl cyclohexanediamine. The method for producing N,N'-dimethyl cyclohexanediamine disclosed by the invention is simple in process, low in raw material cost, toxic-free in production process and high in product purity to be greater than 98%.

Description

technical field [0001] The invention relates to a production method of N,N' dimethylcyclohexanediamine. Background technique [0002] N,N'dimethylcyclohexanediamine, the molecular formula is C 8 h 17 N, also known as dimethylcyclohexylamine, is mainly used as a catalyst for rigid polyurethane foam, used in refrigerator rigid foam, panels, spraying, and on-site pouring of polyurethane rigid foam. Literature (Journal of the American Chemical Society, 2002, 124(39):11684-11688) reported a production method of N,N' dimethylcyclohexanediamine, firstly cyclohexanediamine and chloroformate Or formate reaction, and then use lithium aluminum hydride to reduce the above-mentioned dangerous goods reactant to obtain the target product. The disadvantages of this method are: the reaction raw materials are expensive, and the strong reducing agent lithium aluminum hydride is highly toxic. Therefore, it becomes very meaningful to find a safer, more reliable, and easier industrialized p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/36C07C209/62
Inventor 张燕程
Owner 姜树林
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