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Method for preparing 1,8-menthane diacetyl amide from turpentine

A technology of menthane diacetamide and turpentine, applied in the field of producing 1,8-mentane diacetamide, which can solve the problems of low efficiency, high cost, cumbersome purification process, etc.

Active Publication Date: 2015-11-11
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the shortcomings of the existing 1,8-mentane diacetamide preparation technology, such as low efficiency, high cost, and complicated purification process, the invention provides a method for preparing 1,8-mentane diacetamide from turpentine , using cheap and easy-to-obtain natural products turpentine or pinene and low-toxic acetonitrile as raw materials for isomerization and acylation reaction, which simplifies the production process route and reduces the production cost of 1,8-mentane diethylamide and its downstream products , reducing the hazards of the surrounding environment

Method used

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  • Method for preparing 1,8-menthane diacetyl amide from turpentine
  • Method for preparing 1,8-menthane diacetyl amide from turpentine

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Embodiment 1

[0032] Add 84.3g turpentine (94.5% pinene GC content, 0.58mol) and 63.2g acetonitrile (1.54mol) into a 1L reactor, mechanically stir until the solution is evenly mixed, slowly drop 225g60% H 2 SO 4 Aqueous solution (containing H 2 SO 4 1.38mol), after the dropwise addition was completed, the temperature was slowly raised to 75°C, and the heat preservation reaction was carried out for 5 hours. After the reaction was completed, the reaction solution was neutralized to neutrality with aqueous sodium hydroxide solution, extracted with ethyl acetate, and the organic layer was collected to precipitate the product , filtered and washed the precipitate to obtain 91.1 g (0.36 mol) of 1,8-mentane diacetamide.

Embodiment 2

[0034] Add 84.6g turpentine (94.5% pinene GC content, 0.59mol) and 79.0g acetonitrile (1.92mol) into a 1L reactor, stir mechanically until the solution is evenly mixed, and slowly drop in 225g60% H 2 SO 4 Aqueous solution (containing H 2 SO 4 1.38mol), after the dropwise addition was completed, the temperature was slowly raised to 75°C, and the heat preservation reaction was carried out for 5 hours. After the reaction was completed, the reaction solution was neutralized to neutrality with aqueous sodium hydroxide solution, extracted with ethyl acetate, and the organic layer was collected to precipitate the product , filtered and washed the precipitate to obtain 41.6 g (0.16 mol) of 1,8-mentane diacetamide.

Embodiment 3

[0036]Add 84.4g turpentine (94.5% pinene GC content, 0.59mol) and 39.5g acetonitrile (0.96mol) into a 1L reactor, stir mechanically until the solution is evenly mixed, and slowly drop in 225g60% H 2 SO 4 Aqueous solution (containing H 2 SO 4 1.38mol), after the dropwise addition was completed, the temperature was slowly raised to 75°C, and the heat preservation reaction was carried out for 5 hours. After the reaction was completed, the reaction solution was neutralized to neutrality with aqueous sodium hydroxide solution, extracted with ethyl acetate, and the organic layer was collected to precipitate the product , filtered and washed the precipitate to obtain 22.3 g (0.088 mol) of 1,8-mentane diacetamide.

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Abstract

The invention discloses a method for preparing 1,8-menthane diacetyl amide from turpentine, which comprises the following steps: reacting a raw material turpentine or industrial pinene with acetonitrile by using a strong protonic acid water solution as a catalyst to prepare the product; and after the reaction is sufficient, neutralizing the reaction solution with an inorganic strong alkali water solution, adding a non-water-soluble organic solvent for extraction, collecting and standing the organic layer to precipitate the product, filtering, and washing the precipitate to obtain the 1,8-menthane diacetyl amide solid. The 1,8-menthane diacetyl amide product obtained by the method has the advantages of high yield and favorable purity. Compared with the original preparation process, the method uses the cheaper and more accessible turpentine or industrial pinene as the raw material, is simple in process route, and greatly lowers the production cost of the 1,8-menthane diacetyl amide and downstream products thereof. Besides, the method has the advantages of low toxicity, simple operational process and the like.

Description

Technical field: [0001] The invention relates to a process for producing 1,8-mentane diacetamide, in particular to a process for producing 1,8-mentane diacetamide by a one-step reaction method of turpentine oil and acetonitrile. Background technique [0002] The amide C–N bond is an important structural element of biologically active molecules such as polypeptides and proteins in organisms. Therefore, many compounds with amide groups have excellent insecticidal, bacteriostatic, herbicidal, anti-plant virus and anti-tumor activities. , are widely used in medicine, pesticides and other fields. In addition, many amide compounds are also important organic synthesis intermediates, often used in the synthesis of heteroatoms or heterocyclic compounds, and have extremely important application values ​​in the chemical industry, fragrances, dyes, and textile industries. [0003] Since the first discovery of amide systemic fungicides by Schmeling et al. in the 1960s, dozens of drugs w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/06C07C231/06
Inventor 赵振东徐士超陈玉湘李冬梅毕良武王婧古研卢言菊
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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