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Synthesizing method of N,N-diethyl-3,7-dimethyl-(E)-2,6-octadiene-1-amine

A technology of dimethyl and octadiene, which is applied in chemical instruments and methods, condensation/addition reactions to prepare amino compounds, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem of low yield, Not suitable for industrial production and other problems, to achieve the effect of simple operation

Active Publication Date: 2011-02-09
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] N, N-diethyl-3,7-dimethyl-(E)-2,6-octadiene-1-amine synthesis technology has been reported both at home and abroad such as Takabe, K etc. report that it uses lithium metal, Diethylamine, myrcene reaction only gives 74%-77% yield (Takabe, K.; Katagiri, T.; Tanaka, J.; Fujita, T.; Watanabe, S.; Suga, K.Org.Synth .1993,8,188-191.); Wang Zhijun et al. reported that with metallic lithium, diethylamine, myrcene and adding solvent, the highest yield of 85.4% was obtained (Wang Zhijun et al., Fine Chemical Intermediates, 2005,35(3) , 42-44), but they were limited to using one kind of metal and did not use a mixture of various metals, especially never used auxiliary catalysts and their mixtures, resulting in a low yield and not suitable for industrial production

Method used

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  • Synthesizing method of N,N-diethyl-3,7-dimethyl-(E)-2,6-octadiene-1-amine

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Experimental program
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Effect test

Embodiment 1

[0010] Under the protection of nitrogen, add 10ml toluene, 17g myrcene (purity 80%), 10g diethylamine, 0.2g lithium, 4g styrene to a 100ml reaction flask under the protection of nitrogen, heat to 40 degree, after stirring for 18 hours, stop heating. When the temperature drops to room temperature, slowly add 20ml of deionized water dropwise to keep the system temperature below 40°C. After the dropwise addition is complete, stir for another 30 minutes, let it stand for liquid separation, extract the water phase with 20ml of toluene twice, combine and add to the organic phase , toluene and some impurities were evaporated under reduced pressure to obtain 20.6 g of colorless liquid, GC showed N, N-diethyl-3,7-dimethyl-(E)-2,6-octadien-1-amine The content is 92%, and the yield is 90.7%.

Embodiment 2

[0012] Under the protection of nitrogen, add 15ml cyclohexane, 17g myrcene (80% purity), 10g diethylamine, 0.2g lithium, 5g naphthalene to a 100ml reaction flask, heat to 80 degrees, after stirring for 15 hours, stop heating . When the temperature drops to room temperature, slowly add 20ml of deionized water dropwise, keeping the system temperature not exceeding 40 degrees, after the dropwise addition is completed, stir for another 30min, let it stand for liquid separation, extract the water phase twice with 20ml cyclohexane, combine and add In the organic phase, cyclohexane and some impurities were evaporated under reduced pressure to obtain 21 g of a colorless liquid. GC showed that N, N-diethyl-3,7-dimethyl-(E)-2,6-octadiene- The content of 1-amine was 91%, and the yield was 91%.

Embodiment 3

[0014] Under the protection of nitrogen, add 15ml methyl tert-butyl ether, 10g diethylamine, 0.2g lithium, 0.1g sodium, 5g styrene to a 100ml reaction bottle, after stirring for 30min, add 17g myrcene (purity 80%) , sealed, heated to 60 degrees, and after stirring for 17 hours, stop heating. When the temperature drops to room temperature, slowly add 20ml of deionized water dropwise to keep the system temperature below 40°C. After the dropwise addition is complete, stir for another 30min, let it stand for liquid separation, and extract the water phase twice with 20ml of methyl tert-butyl ether , combined and added to the organic phase, and evaporated under reduced pressure to remove methyl tert-butyl ether and some impurities to obtain 20.7 g of a colorless liquid. GC showed that N, N-diethyl-3,7-dimethyl-(E)-2 , the content of 6-octadien-1-amine was 93%, and the yield was 92.1%.

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Abstract

The invention relates to a synthesizing method of N,N-diethyl-3,7-dimethyl-(E)-2,6-octadiene-1-amine, belonging to the technical field of chemical industry. In the method, myrcene and diethylamine which are used as raw materials are synthesized into the N,N-diethyl-3,7-dimethyl-(E)-2,6-octadiene-1-amine with higher yield coefficient under the catalysis of metals and corresponding auxiliary catalysts. The invention has certain industrial prospect.

Description

technical field [0001] The invention belongs to the technical field of chemistry and chemical engineering, and in particular relates to a synthesis method of N,N-diethyl-3,7-dimethyl-(E)-2,6-octadiene-1-amine. Background technique [0002] N,N-diethyl-3,7-dimethyl-(E)-2,6-octadiene-1-amine is an important organic chemical intermediate, widely used, it has certain biological activity, It can be directly used as an insecticide with high efficiency and low toxicity; it can also be used as a fine chemical intermediate to synthesize bulk spices such as citral, citronellal and menthol; it can also be used as a drug precursor to synthesize some chiral drugs through asymmetric catalysis , such as methoprene, vitamin A and vitamin E. With the increasing application of fragrances and chiral drugs, the market demand for N,N-diethyl-3,7-dimethyl-(E)-2,6-octadien-1-amine is also increasing , but there is no industrial production factory in China. Therefore, it is of great significance...

Claims

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Application Information

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IPC IPC(8): B01J31/26C07C209/60C07C211/21
Inventor 姜标陈旭敏王万军赵小龙
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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