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Synthetic method of dimethyl cyclohexanediamine aromatic ring
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The technology of a kind of dimethylcyclohexanediamine and the synthesis method is applied in the field of synthesis of aromatic ring of dimethylcyclohexanediamine, which can solve the problems that lithium aluminum hydride, a strong reducing agent, is highly toxic, and the price of reaction raw materials is expensive, etc., and achieves Easy operation and simple process
Inactive Publication Date: 2014-12-17
姜树林
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Literature (Journal of the American Chemical Society, 2002,124(39):11684-11688) reports a production method of dimethylcyclohexanediamine, first reacting cyclohexanediamine with chloroformate or formate , and then use lithium aluminum hydride to reduce the above-mentioned dangerous reactants 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.
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Embodiment 1
[0017] Step 1: Sulfonation of o-phenylenediamine
[0018] Dissolve 20mmol of o-phenylenediamine in 10ml of pyridine, add the above solution dropwise to 40mmol of p-toluenesulfonyl chloride in 10ml of pyridine solution, control the temperature below 60℃ during the dropwise addition, when the color of the solution changes from colorless to dark red When the dripping was completed, it was left to react at room temperature for 7 hours, the reaction was stopped, 15% hydrochloric acid was added to adjust the pH to 6-7, left standing for 24 hours, filtered and washed with water (10ml×3) to obtain 7.0300g of white powdery solid.
[0019] Step 2: Methylation
[0020] Dissolve 7.18 mmol of the product in step 1 in 60 ml of acetonitrile, add 28.7 mmol of potassium carbonate powder, stir at room temperature for 1 h, put 28.7 mmol of methyl iodide in an ice bath, react for 30 min, remove the ice bath and react at room temperature for 12 h, stop the reaction, Acetonitrile was removed by ro...
Embodiment 2
[0026] Step 1: Sulfonation of o-phenylenediamine
[0027] Dissolve 20mmol of p-phenylenediamine in 10ml of pyridine, add the above solution dropwise to 40mmol of p-toluenesulfonyl chloride
[0028] In 10ml of pyridine solution, the temperature of the dropwise addition process was controlled below 60°C. When the color of the solution changed from colorless to dark red, the dropping was completed, and the reaction was placed at room temperature for 7h. The reaction was stopped, and 15% hydrochloric acid was added to adjust the pH to 6. -7, stand for 24h, filter, and wash with water (10ml×3) to obtain 7.45g of white powdery solid.
[0029] Step 2: Methylation
[0030] Dissolve 7.18 mmol of the product in step 1 in 60 ml of acetonitrile, add 28.7 mmol of potassium carbonate powder, stir at room temperature for 1 h, put 28.7 mmol of methyl iodide in an ice bath, react for 30 min, remove the ice bath and react at room temperature for 12 h, stop the reaction, Acetonitrile was remov...
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Abstract
The invention discloses a synthetic method of a dimethyl cyclohexanediamine aromatic ring. The method comprises the steps of: carrying out a reaction of phenylenediamine and aryl benzene sulfonyl chloride for protecting nitrogenous bases; then, carrying out methylation with methyl iodide, methyl bromide or dimethyl sulfate; hydrolyzing sulfuric acid to remove aryl benzenesulfonic acid groups to obtain dimethyl o-phenylenediamine; and finally, carrying out deep hydrogenation reaction of a benzene ring under the effect of a palladium-carbon catalyst, and carrying out post-treatment to obtain dimethyl cyclohexanediamine. The synthetic method of the dimethyl cyclohexanediamine aromatic ring provided by the invention is simple in process and easy to operate, and the total yield of products reaches 40-60%.
Description
technical field [0001] The invention relates to a method for synthesizing an aromatic ring of dimethylcyclohexanediamine. Background technique [0002] Dimethylcyclohexylamine, the molecular formula is C8H17N, also known as N,N' - dimethylcyclohexylamine, the main use is as a catalyst for rigid polyurethane foam, used in refrigerator rigid foam, plate, spraying, on-site pouring polyurethane Hard bubbles. The literature (Journal of the American Chemical Society, 2002, 124(39): 11684-11688) reported a method for producing dimethylcyclohexanediamine, first reacting cyclohexanediamine with chloroformate or formate , and then use lithium aluminum hydride to reduce the above-mentioned dangerous goods reactants 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 is very meaningful to find a safer, more reliable and easier industrialized p...
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