Synthesis and characterization of amide based palm oil polyol via ring opening reaction

The used of epoxidized palm oil (EPO) as intermediate for polyol production has been the main interest due to the ability of the epoxy group to react with various nucleophiles such as hydroxyl and amines. However, there are relatively limited number of articles that discuss the mechanism of ring ope...

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Main Author:	Soloi, Sabrina
Format:	Thesis
Language:	English
Published:	2018
Subjects:	TP Chemical technology
Online Access:	http://eprints.utm.my/id/eprint/86949/1/SabrinaSoloiPSChE2018.pdf
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spelling	my-utm-ep.869492020-10-30T05:13:37Z Synthesis and characterization of amide based palm oil polyol via ring opening reaction 2018 Soloi, Sabrina TP Chemical technology The used of epoxidized palm oil (EPO) as intermediate for polyol production has been the main interest due to the ability of the epoxy group to react with various nucleophiles such as hydroxyl and amines. However, there are relatively limited number of articles that discuss the mechanism of ring opening reaction of EPO with nucleophiles. In this study, the epoxy ring of EPO underwent ring opening reaction using isopropanolamine (IPA) as the nucleophile and boron trifluoride ethanol complex as catalyst. The mechanism of this reaction was following unimolecular nucleophilic substitution reaction (SN1) based on detail analysis using Fourier transform infrared (FTIR) spectroscopy and nuclear magnetic resonance (NMR). Reaction time, reaction temperature, catalyst amount and molar ratio of EPO:IPA were varied in order to investigate the efficiency of IPA as the ring opening reagent. It was found that the ring opening reaction occurred after 6 hours of reaction at 60oC with 1 mL of boron trifluoride ethanol complex catalyst and at the ratio of 1:3 EPO:IPA. However, small trace of unopened epoxy ring was detected by FTIR and NMR analyses at 824-830 cm-1 and 2.89 ppm. Further analysis with FTIR and NMR revealed that IPA preferred to attack the ester linkages over the epoxy ring, thus producing amide polyols as the main product. Findings from mass spectroscopy analysis and gel permeation chromatography showed that amide polyols had shorter chain length with the molecular weights ranging from 400 to 600 Da with broad distribution. From hydroxyl value analysis, amide polyols have functionality of 2, thus suitable to be used as precursor in many chemical reactions. Further investigation with thermogravimetric analysis showed that amide polyols had thermal decomposition at temperatures of 600oC, indicating that they can be used at high- temperature reactions. 2018 Thesis http://eprints.utm.my/id/eprint/86949/ http://eprints.utm.my/id/eprint/86949/1/SabrinaSoloiPSChE2018.pdf application/pdf en public http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:131372 phd doctoral Universiti Teknologi Malaysia, Faculty of Engineering - School of Chemical & Energy Engineering Faculty of Engineering - School of Chemical & Energy Engineering
institution	Universiti Teknologi Malaysia
collection	UTM Institutional Repository
language	English
topic	TP Chemical technology
spellingShingle	TP Chemical technology Soloi, Sabrina Synthesis and characterization of amide based palm oil polyol via ring opening reaction
description	The used of epoxidized palm oil (EPO) as intermediate for polyol production has been the main interest due to the ability of the epoxy group to react with various nucleophiles such as hydroxyl and amines. However, there are relatively limited number of articles that discuss the mechanism of ring opening reaction of EPO with nucleophiles. In this study, the epoxy ring of EPO underwent ring opening reaction using isopropanolamine (IPA) as the nucleophile and boron trifluoride ethanol complex as catalyst. The mechanism of this reaction was following unimolecular nucleophilic substitution reaction (SN1) based on detail analysis using Fourier transform infrared (FTIR) spectroscopy and nuclear magnetic resonance (NMR). Reaction time, reaction temperature, catalyst amount and molar ratio of EPO:IPA were varied in order to investigate the efficiency of IPA as the ring opening reagent. It was found that the ring opening reaction occurred after 6 hours of reaction at 60oC with 1 mL of boron trifluoride ethanol complex catalyst and at the ratio of 1:3 EPO:IPA. However, small trace of unopened epoxy ring was detected by FTIR and NMR analyses at 824-830 cm-1 and 2.89 ppm. Further analysis with FTIR and NMR revealed that IPA preferred to attack the ester linkages over the epoxy ring, thus producing amide polyols as the main product. Findings from mass spectroscopy analysis and gel permeation chromatography showed that amide polyols had shorter chain length with the molecular weights ranging from 400 to 600 Da with broad distribution. From hydroxyl value analysis, amide polyols have functionality of 2, thus suitable to be used as precursor in many chemical reactions. Further investigation with thermogravimetric analysis showed that amide polyols had thermal decomposition at temperatures of 600oC, indicating that they can be used at high- temperature reactions.
format	Thesis
qualification_name	Doctor of Philosophy (PhD.)
qualification_level	Doctorate
author	Soloi, Sabrina
author_facet	Soloi, Sabrina
author_sort	Soloi, Sabrina
title	Synthesis and characterization of amide based palm oil polyol via ring opening reaction
title_short	Synthesis and characterization of amide based palm oil polyol via ring opening reaction
title_full	Synthesis and characterization of amide based palm oil polyol via ring opening reaction
title_fullStr	Synthesis and characterization of amide based palm oil polyol via ring opening reaction
title_full_unstemmed	Synthesis and characterization of amide based palm oil polyol via ring opening reaction
title_sort	synthesis and characterization of amide based palm oil polyol via ring opening reaction
granting_institution	Universiti Teknologi Malaysia, Faculty of Engineering - School of Chemical & Energy Engineering
granting_department	Faculty of Engineering - School of Chemical & Energy Engineering
publishDate	2018
url	http://eprints.utm.my/id/eprint/86949/1/SabrinaSoloiPSChE2018.pdf
_version_	1747818515894632448

Synthesis and characterization of amide based palm oil polyol via ring opening reaction

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