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Alkynated and azidated octadecane as model compounds for kinetic studies of Huisgen 1,3‐dipolar cycloaddition in vegetable oils
Author(s) -
Hong Jian,
Radojčić Dragana,
Hairabedian Djavan,
Wan Xianmei,
Petrović Zoran S.
Publication year - 2015
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201400461
Subject(s) - octadecane , cycloaddition , chemistry , kinetics , 1,3 dipolar cycloaddition , reactivity (psychology) , polymer chemistry , organic chemistry , catalysis , physics , quantum mechanics , medicine , alternative medicine , pathology
Alkynated and azidated octadecane, synthesized from 9‐octadecene, were used as model compounds for alkynated and azidated vegetable oils to study the kinetics of thermal Huisgen 1,3‐dipolar cycloaddition. Alkyne and azide groups of alkynated and azidated octadecane possess low reactivity as they are branched in the middle of an 18‐carbon chain. Reaction kinetics was studied by GPC, 1 H NMR, and DSC. Detailed kinetic analysis revealed that the reaction of alkynated and azidated octadecane required 24 h to reach 90% conversion at 100°C. The activation energy of the reaction is 55 kJ/mol. Practical applications : The kinetics study of this model reaction is necessary for estimating the extent of reaction and necessary curing time of the thermal polycycloaddition of alkynated and azidated vegetable oils whose main components are triglyceride‐containing aliphatic chains of 16–22 carbons. Kinetics of thermal Huisgen 1,3‐dipolar cycloaddition of alkynated and azidated octadecane (A‐OCD and Az‐OCD) as model compounds for alkynated and azidated vegetable oils was studied by GPC, DSC, and spectroscopic methods.