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Method for preparing 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine from 1,8- terpinum

A technology for terpene diols and diazidoalkanes, which is applied in the field of preparing alkanediamines, can solve the problems of difficult industrialization, little practical significance, reduced yield and the like, and achieves simple and easy operation, reduced risk, and reduced toxic effects

Active Publication Date: 2007-12-12
湖南松本林业科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest disadvantage of this method is the need to prepare special HN 3 solution, very dangerous, this method uses N 3 H / BF 3 -Et 2 O is a catalytic system, the system is very sensitive to moisture, and the solvents used are all organic solvents, the pollution is serious, it is difficult to realize industrialization, and the practical significance is not great
[0011] Jeffrey C. Bottaro et al. (Synth Commun, 1997: 1465-1467) proposed that at 25°C NaN 3 Stand still in 50% (wt) sulfuric acid solution with tert-butyl alcohol for 30h to obtain tert-butyl azide, this method is characterized by economy, environmental protection, easy separation of products and high purity of products, but the biggest disadvantage of this method Yes, a Schmidt rearrangement reaction will occur to generate amides and reduce the yield

Method used

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  • Method for preparing 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine from 1,8- terpinum
  • Method for preparing 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine from 1,8- terpinum
  • Method for preparing 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine from 1,8- terpinum

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Add 74.3g of water into a 250mL container that can be completely closed, add 90.8g of concentrated sulfuric acid dropwise under the condition of stirring and ice-water bath to prepare a 55% (wt) sulfuric acid solution, and add NaN below 15°C 3 11.8g, stirred for 5min to dissolve completely, then added 15.7g of 1,8-terpene diol, heated to 45°C and kept at a constant temperature for 6h, separated and dried to obtain diazide 11.6g of the mixture of alkane, after analyzing the diazide group in the mixture The content of alkane is 58.59% (wt).

Embodiment 2

[0034] Add 90.8g of water into a 250mL container that can be completely closed, add 74.3g of concentrated sulfuric acid dropwise under the condition of stirring and ice-water bath to prepare a 45% (wt) sulfuric acid solution, and add NaN below 15°C 3 11.8g, stirred for 5min to dissolve completely, then added 15.7g of 1,8-terpene diol, heated to 50°C and kept at a constant temperature for 8h, separated and dried to obtain diazide 13.2g of the mixture of alkane, after analyzing the diazide group in the mixture The content of alkane is 89.24% (wt).

Embodiment 3

[0036] Add 90.8g of water into a 250mL container that can be completely closed, add 74.3g of concentrated sulfuric acid dropwise under the condition of stirring and ice-water bath to prepare a 45% (wt) sulfuric acid solution, and add NaN below 15°C 3 11.8g, stirred for 5min to dissolve completely, then added 15.7g of 1,8-terpene diol, heated to 35°C and kept at a constant temperature for 40h, separated and dried to obtain diazide 12.4g of the mixture of alkane, after analyzing the diazide group in the mixture The content of alkanes was 50.3% (wt).

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Abstract

The invention relates to a method for preparing alkyl-diamine with 1, 8- terpin. It comprises following steps: preparing sulphuric acid solution with mass concentration being 10- 75% at closed condition, adding NaN3 at 10- 15 Deg. C, stirring thoroughly to disslove it in said sulphuric acid solution, then adding 1, 8- terpin, controlling temperature to be between 15-100 Deg. C, stewing, separating and drying after reaction finished and getting diazanyl. The molar ratio between NaN3 and 1, 8- terpin is (2.0- 3.0): 1, the invention employs 5%Pd-C or Lindlar as catalyst to reduce diazanyl and gets alkyl-diamine mixture, distilling, rectifying and getting final product alkyl-diamine. The invention employs NaN3 as raw material, which reduces raw material toxicity, it employs sulfuric acid solution as reaction medium and catalyst, which can be reused when the concentration is moderated, the cost is saved and pollution to enviroment is decreased.

Description

[0001] Prepared from 1,8-terpene diol Alkanediamine method technical field [0002] The present invention relates to a kind of preparation by 1,8-terpene diol Alkanediamine method. Background technique [0003] Alkanediamine (4-amino-α, α, 4-trimethyl-cyclohexanemethanamine) is a derivative of pinene, a monoterpenoid compound. It is a chemical compound with a molecular structure of: [0004] [0005] Alkanediamine is liquid in a wide temperature range and maintains low viscosity, heat resistance, will not be oxidized at high temperature, has good solubility in hydrocarbon petroleum solvents, and has high alkalinity and properties that can control its reactivity and stereoselectivity. [0006] Alkanediamine is an important curing agent for cycloaliphatic epoxy resins that has been identified. In addition, it can also be used as a bacterial inhibitor in soaps and a raw material for polyamides, polyurethanes, silanol condensation catalysts, and some new alkylation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/36C07C209/42
Inventor 赵振东冯志勇毕良武王婧李冬梅古研
Owner 湖南松本林业科技股份有限公司
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