New Method of Synthesis of Oligoetherols with Carbazole Ring.

Renata Lubczak

doi:10.17344/acsi.2014.1296

Abstract

The new method of synthesis of multifuntional oligoetherols with carbazole ring suitable for obtaining the polyurethane foams of enhanced thermal resistance was presented. At the first step of the synthesis the carbazole was reacted with excess glycidol to obtain the product of (n +1) functionality, where n is number of equivalents of glycidol reacted with carbazole. This semiproduct was then reacted with oxiranes like ethylene and propylene oxides or alkylene carbonates like ethylene and propylene carbonates. The progress of reaction as well as structure of the products were studied by classic and instrumental methods like elemental analysis, IR, (1)H-NMR, and MALDI-ToF spectroscopies. Some physico-chemical properties of the products were described.

Highlights

In another procedure the oligoetherols were obtained in multistep reaction sequence: the reaction of carbazole with ethylene chloride, with diethanolamine to get diol, which was reacted with oxiranes.[18]
The reaction of carbazole with glycidol without solvent was performed at the carbazole : glycidol molar ratio 1 : 1–1 : 10
In the presence of TEA catalyst still carbazole remained untouched while glycidol converted into polyglycidol products

Summary

Introduction

The linear oligoetherols were obtained by its reaction with glycerol epichlorhydrin to give 9-(2,3-epoxypropyl)carbazole followed by epoxide ring opening with water, ethylene glycol or ethanolamine, and further conversion by reaction with oxiranes to get bi-functional oligoetherols.[16,17,18] In another procedure the oligoetherols were obtained in multistep reaction sequence: the reaction of carbazole with ethylene chloride, with diethanolamine to get diol, which was reacted with oxiranes.[18] Initially obtained 9-(2,3-epoxypropyl)carbazole was converted into multifunctional product by ring opening with glycerol or sorbitol.[20,22] These products were hydroxyalkylated with oxiranes and further used to obtain linear polyurethanes (PU) and PU foams of good thermal resistance. The protocol leading to multifunctional derivatives (oligoetherols) is described, together with the structure and properties of products, which are suitable substrates to obtain PU foams of enhanced thermal resistance

Experimental Section

2. Analytical Methods

Results and Discussion

Conclusions