Synthesis of Palm Oil‐Based Diethanolamides

Abstract

In this work, Epoxidized Palm Olein (EPO o ) was blended with Refined Bleached Deodorized Palm Kernel Olein (RBDPKO o ) in a range of 10-100% (w/w) to react with diethanolamine (DEA) with a 1:3 molar ratio to produce diethanolamides that retained some epoxides. The epoxidized diethanolamides are proposed as a new type of vegetable oil derived polyols for rigid polyurethane. The optimal reaction temperature is 110°C for 5 h. In addition, the optimal amount of starting materials were determined to be 40% (w/w) of EPO o blended with 60% (w/w) of RBDPKO o . The diethanolamides appeared as non-viscous liquid at room temperature with a viscosity of 990.08 cP at 25°C and 427.09 cP at 40°C, a cloud point of 21°C, a pour point of 12°C and 0.78% of retained oxirane oxygen contents (OOC). The hydroxyl and the amine values of the diethanolamides were determined as 351.85 mg KOH/g sample and 4.5 mg KOH/g sample, respectively. In addition, chemical elucidation of the diethanolamides with functional epoxides was carried out using Gas Chromatography (GC) and Gas Chromatography Mass Spectrometry (GCMS) for the purpose of process development and quality control.

The Effect of Reaction Temperature on Retaining Oxirane Oxygen Contents in the Synthesis of Epoxidized Diethanolamides

“…Forty percent (w/w) of EPO o was blended with RBDPKO o as optimal starting material due to the diethanolamide products appeared as non-viscous liquid at room temperature with low viscosity as reported in another paper [14] . The staring material was then reacted with DEA at molar ratio of 1:3 (palm oil TAG: DEA) (Scheme 1).…”

“…The optimum reaction temperature and reaction duration from the previous study were 110°C for 5 h [14] . Therefore, in this study, we tried to retain maximum oxirane oxygen contents in diethanolamide products by reacting the reaction mixture at lower temperatures, ranging from 110-80°C.…”

“…In the previous study, there were 34.5% of epoxy ring breakings when the epoxidized palm olein (EPO o ) reacted with diethanolamine at 110°C for 5 h [14] . Consequently, in the present work, we report on the preparation method at different temperatures to retain maximum percentage of oxirane oxygen contents in epoxidized diethanolamide products.…”

“…A series of epoxidized diethanolamides had been produced by using varying amount of Epoxidized Palm Olein (EPO o ) and RBDPKO o to react with DEA [14] . The synthesized diethanolamides, consisting of reactive epoxy compounds, would provide extra cross-linking sites to allow the epoxides to react with diisocyanates to form oxazolidones during polyurethane foam production [15] .…”

Seed Oil Based Polyurethanes: An Insight

“…The properties of SO polyols obtained by either method mentioned previously, also influence the properties of FAP. Hydroxylated, hydroxymethylated, carboxylated SO followed by their amidation yield polyols with higher number of hydroxyl groups with improved distribution [50][51][52][53][54][55][56]. These are ideal candidates to produce PU foams.…”