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Cycloalkylation reactions of fatty amines with α,ω-dihaloalkanes: Role of bis-quaternary ammonium salts as phase-transfer catalysts

Paper ID Volume ID Publish Year Pages File Format Full-Text
52741 46885 2007 6 PDF Available
Title
Cycloalkylation reactions of fatty amines with α,ω-dihaloalkanes: Role of bis-quaternary ammonium salts as phase-transfer catalysts
Abstract

Bis-quaternary salts are effective phase-transfer catalysts in the cycloalkylation phase reactions of amines. The catalytic activity of these quats is similar to that of conventional quaternary ammonium catalysts, such as benzyltriethylammonium chloride and tetraethylammonium bromide. Bis-quaternary ammonium surfactants have attracted great interest. They are constituted of two hydrophilic groups per molecular unit, separated by a spacer. This is quite different from the catalytic behavior for the conventional surfactant, which leads to a more selective alkylation. Phase-transfer catalysis and micellar phase-transfer catalysis are two well-known methods of promoting reactions mainly between lipophilic and hydrophilic reactants. An intramolecular cycloalkylation of fatty amines, C12H25NH2 and C16H33NH2, with several α,ω-dihaloalkanes, viz., 1,2-dibromoethane C2H4Br2, trans-1,4-dichloro-2-butene C4H6Cl2, 1,6-dibromohexane Br(CH2)6Br, under PTC conditions are reported. In particular, the cycloalkylation of amine with an excess of α,ω-dihaloalkane has been studied in the presence of 1.9 × 10−6 mol% bis-quaternary dihalide surfactants (I and II) as PT catalysts and sodium hydroxide (25%) as a base, at 50–60 °C. The reaction was completed in less than 4 h selectively yielding the desired cycloadduct. The structures of the synthesized cycloadducts formed were evidenced by elemental analyses, IR and 1H NMR spectral analyses.

Keywords
Bis-quaternary amines; Phase-transfer catalysis; Micellar phase-transfer catalysis; Analytical applications; Cycloalkylation; Liquid–liquid reactions; Catalyst activity
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Cycloalkylation reactions of fatty amines with α,ω-dihaloalkanes: Role of bis-quaternary ammonium salts as phase-transfer catalysts
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 8, Issue 6, June 2007, Pages 855–860
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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