Preparation method of 5,5-dimethyl-1,3-cyclohexamethylenediamine

A technology of cyclohexanediamine and dimethyl, which is applied in the field of chemical synthesis, can solve the problems of being unsuitable for industrial production scale-up, low product yield and purity, and cumbersome post-treatment, and achieves benefits for scale-up of industrial production, low cost, and method novel effects

Inactive Publication Date: 2015-05-06
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Experiments show that LiAlH 4 The reduction method has low safety, the system exothermic is very obvious during the feeding process, and the reaction system expands rapidly in the container during the reaction process, causing the system to be easily flushed, posing a safety hazard, and the post-treatment is very cumbersome, and the yield and purity of the obtained product are average. lower
Therefore, this method is not suitable for industrial scale-up

Method used

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  • Preparation method of 5,5-dimethyl-1,3-cyclohexamethylenediamine
  • Preparation method of 5,5-dimethyl-1,3-cyclohexamethylenediamine
  • Preparation method of 5,5-dimethyl-1,3-cyclohexamethylenediamine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Step 1, the preparation of 5,5-dimethyl-1,3-cyclohexanedione

[0028] Add 64.4g (0.937mol) sodium ethylate, 138.4g (0.856mol) diethyl malonate, 80.0g (0.815mol) 4-methyl-3-penten-2-one, 257.8g absolute ethanol to In a 2L three-neck flask, stir and mix well, heat to reflux, and stir at reflux for 1 to 2 hours. TLC detects that 4-methyl-3-penten-2-one has reacted completely and there is no residue. Add a mixed solution of 123.0g (1.972mol) KOH and 566g tap water, and stir under reflux for 6-10h. Ethanol in the system was evaporated, and 300g4mol / L HCl aq was added dropwise to the remaining aqueous solution system to adjust the pH value of the system to 1-2, a yellow solid gradually precipitated in the system, cooled to room temperature, and suction filtered, the filter cake was a yellow solid, The filter cake was rinsed with tap water (100 g x 5). After the filter cake was dried, 90.0 g of light yellow granular solid was obtained, the yield was 78.8% (calculated as 4-me...

Embodiment 2

[0034] Step 1, the preparation of 5,5-dimethyl-1,3-cyclohexanedione

[0035] Add 50.6g (0.937mol) sodium methoxide, 138.4g (0.856mol) diethyl malonate, 80.0g (0.815mol) 4-methyl-3-penten-2-one, and 203g methanol to a 2L three-necked flask , stir and mix, heat to reflux, and stir at reflux for 1 to 2 hours. TLC detects that 4-methyl-3-penten-2-one has reacted completely and there is no residue. Add a mixed solution made of 78.9g (1.972mol) NaOH and 363g tap water, and stir under reflux for 6-10h. The methanol in the system was evaporated, and 300g4mol / L HCl aq was added dropwise to the remaining aqueous solution to adjust the pH value of the system to 1-2. A yellow solid gradually precipitated in the system, cooled to room temperature, and suction filtered. The filter cake was a yellow solid. Tap water (100g×5) rinses the filter cake. After the filter cake was dried, 88.5 g of light yellow granular solid was obtained, with a yield of 77.5% (calculated as 4-methyl-3-penten-2-o...

Embodiment 3

[0041] Step 1, the preparation of 5,5-dimethyl-1,3-cyclohexanedione

[0042] Add 76.9 g (0.937 mol) sodium isopropoxide, 138.4 g (0.856 mol) diethyl malonate, 80.0 g (0.815 mol) 4-methyl-3-penten-2-one, 269.8 g tetrahydrofuran to 2L In the three-neck flask, stir and mix well, heat to reflux, and stir at reflux for 1-2 hours. TLC detects that 4-methyl-3-penten-2-one has reacted completely and there is no residue. Add a mixed solution of 123.0g (1.972mol) KOH and 566g tap water, and stir under reflux for 6-10h. The tetrahydrofuran in the system was evaporated, and 300g4mol / L HCl aq was added dropwise to the remaining aqueous solution system to adjust the pH value of the system to 1-2. A yellow solid gradually precipitated in the system, cooled to room temperature, and suction filtered. The filter cake was a yellow solid. The filter cake was rinsed with tap water (100 g x 5). After the filter cake was dried, 87.2 g of a yellowish granular solid was obtained, with a yield of 76....

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Abstract

The invention relates to a preparation method of 5,5-dimethyl-1,3-cyclohexamethylenediamine, which comprises the following steps: 1. preparing 5,5-dimethyl-1,3-cyclohexyldione from 4-methyl-3-pentenyl-2-one and diethyl malonate; 2. adding the 5,5-dimethyl-1,3-cyclohexyldione into a polar organic solvent, carrying out condensation reaction with hydroxylamine hydrochloride under the action of an alkaline reagent to prepare 5,5-dimethyl-1,3-cyclohexyldiketodioxime; and 3. adding a polar organic solvent into the 5,5-dimethyl-1,3-cyclohexyldiketodioxime, and carrying out catalytic hydrogenation reduction reaction under the catalytic action of a metal catalyst to prepare the 5,5-dimethyl-1,3-cyclohexamethylenediamine. The total yield of the method is 50-55%, the gas-phase purity and content can reach 98.0% above, and the method has high safety and is simple to operate and beneficial to industrial production amplification.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of 5,5-dimethyl-1,3-cyclohexanediamine, which is simple in operation and beneficial to industrial production scale-up. Background technique [0002] Cyclohexanediamine compounds are a class of compounds that are widely used, and are widely used in pharmaceutical intermediates, epoxy resin curing agents (such as coatings, adhesives, composite materials, etc.), chiral synthesis reagents, catalysts, polyamides, etc. Resins, dyes, polyamide fibers, etc. [0003] 5,5-Dimethyl-1,3-cyclohexanediamine is one of the cyclohexanediamine compounds, the molecular formula is C 8 h 18 N 2 , has the following structural formula: However, this compound is not commercially available in the international market. Therefore, the development and application of the compound will have great prospects. [0004] [0005] In the prior art, the intermediat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/36C07C209/40
Inventor 郝飞跃刘一王志勇贾公明周银波崔明
Owner VALIANT CO LTD
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