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

A technology of terpene diol and diazide alkanes, which is applied in the field of preparation of alkane diamines, can solve the problems of little practical significance, difficulty in realizing industrialization, and reduced yield, and achieve simple and easy operation, easy separation, and reduced risk sexual effect

Active Publication Date: 2009-05-13
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
[0010] 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
Comparison scheme
Effect test

Embodiment 1

[0031] Add 74.3g of water into a 250mL container that can be completely sealed, add 90.8g of concentrated sulfuric acid dropwise under stirring and ice-water bath to prepare a 55% (wt) sulfuric acid solution, add NaN below 15℃ 3 11.8g, stir for 5min to dissolve completely, then add 15.7g 1,8-terpene diol, heat to 45℃ and let stand for 6h, separate and dry to obtain the diazide group 11.6g of alkane mixture, after analyzing the diazide group in the mixture The alkane content is 58.59% (wt).

Embodiment 2

[0033] Add 90.8g of water into a 250mL container that can be completely sealed, add 74.3g of concentrated sulfuric acid dropwise under stirring and ice-water bath to prepare a 45% (wt) sulfuric acid solution, add NaN below 15℃ 3 11.8g, stir for 5min to dissolve completely, then add 15.7g 1,8-terpene diol, heat to 50℃ and let stand for 8h, separate and dry to obtain the diazide group 13.2g of alkane mixture, the diazide group in the mixture was analyzed The alkane content is 89.24% (wt).

Embodiment 3

[0035] Add 90.8g of water into a 250mL container that can be completely sealed, add 74.3g of concentrated sulfuric acid dropwise under stirring and ice-water bath to prepare a 45% (wt) sulfuric acid solution, add NaN below 15℃ 3 11.8g, stir for 5min to completely dissolve, then add 15.7g 1,8-terpene diol, heat to 35 ℃ constant temperature and stand for 40h, separate and dry to obtain the diazide group 12.4g of alkane mixture, after analyzing the diazide group in the mixture The alkane content is 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

Technical field [0001] The invention relates to a preparation made from 1,8-terpene diol Alkylene diamine method. Background technique [0002] Alkyl diamine (4-amino-α, α, 4-trimethyl-cyclohexanemethanamine) is a derivative of the monoterpenoid compound pinene. It is a chemical compound and its molecular structure is: [0003] [0004] Alkylene diamine is liquid in a wide temperature range, maintains low viscosity, heat resistance, will not be oxidized at high temperatures, has good solubility in hydrocarbon petroleum solvents, and has high alkalinity And can control its reactivity and stereoselectivity characteristics. [0005] Alkylene diamine is an important alicyclic epoxy resin curing agent that has been identified. In addition, it can also be used as a bacterial inhibitor in soaps and a raw material for polyamide, polyurethane, silanol condensation catalysts and some new alkylation ligands. ,use Diamine-treated polyester resin can also improve the dyeing ability ...

Claims

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Application Information

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Patent Type & Authority Patents(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