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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
http://eprints.utm.my/id/eprint/86949/
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spelling my.utm.869492020-10-30T05:13:37Z http://eprints.utm.my/id/eprint/86949/ Synthesis and characterization of amide based palm oil polyol via ring opening reaction 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 NonPeerReviewed application/pdf en http://eprints.utm.my/id/eprint/86949/1/SabrinaSoloiPSChE2018.pdf Soloi, Sabrina (2018) Synthesis and characterization of amide based palm oil polyol via ring opening reaction. PhD thesis, Universiti Teknologi Malaysia, Faculty of Engineering - School of Chemical & Energy Engineering. http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:131372
institution Universiti Teknologi Malaysia
building UTM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Malaysia
content_source UTM Institutional Repository
url_provider http://eprints.utm.my/
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
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
publishDate 2018
url http://eprints.utm.my/id/eprint/86949/1/SabrinaSoloiPSChE2018.pdf
http://eprints.utm.my/id/eprint/86949/
http://dms.library.utm.my:8080/vital/access/manager/Repository/vital:131372
_version_ 1683230688344539136
score 13.211869

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