Simple and selective synthesis of 1-monolaurin without catalyst

Glycerol 1-monolaurate, also known popularly as 1-monolaurin, is a monoacylglycerol of lauric acid that has notable antimicrobial properties. It is present in abundant quantities is vegetable oils (i.e. coconut oil). Its most common route of preparation is from lauric acid and glycerol esterificatio...

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Main Author: CAYONA, RUEL
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Published: Archīum Ateneo 2018
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Online Access:https://archium.ateneo.edu/theses-dissertations/240
http://rizalls.lib.admu.edu.ph/#section=resource&resourceid=1563242681&currentIndex=0&view=fullDetailsDetailsTab
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spelling ph-ateneo-arc.theses-dissertations-12392021-03-21T13:36:02Z Simple and selective synthesis of 1-monolaurin without catalyst CAYONA, RUEL Glycerol 1-monolaurate, also known popularly as 1-monolaurin, is a monoacylglycerol of lauric acid that has notable antimicrobial properties. It is present in abundant quantities is vegetable oils (i.e. coconut oil). Its most common route of preparation is from lauric acid and glycerol esterification involving chemical catalysts and enzymes. Unfortunately, this reaction is but a messy reaction which generates a mixture of glycerides that is difficult to purify. Significant effort was invested in the development of highly-selective catalysts but by far none is successful at producing 1-monolaurin exclusively as product. In this work, a simple and selective method of synthesis of 1-monolaurin is described that does not involve catalyst but activated reactants, instead. Lauric acid was first converted to lauroyl chloride before it was reacted with a sodium salt of an activated glycerol derivative, sodium glyceroxide. These reactants were allowed to react in a one-pot system and neat (no solvent) condition at room temperature and pressure. The reaction was both kinetically- and thermodynamically-favorable notwithstanding the modest conditions employed. This result was not achieved before with chemical catalysts or enzymes. The present yield may be low (3.41%) but optimization of relevant reaction variables could increase the yield of the target product and prepare the conditions for bulk synthesis. Furthermore, the method is a very promising alternative to high-purity 1-monolaurin preparation and potentially adaptable general procedure for 1-monoacylglycerides. 2018-01-01T08:00:00Z text https://archium.ateneo.edu/theses-dissertations/240 http://rizalls.lib.admu.edu.ph/#section=resource&resourceid=1563242681&currentIndex=0&view=fullDetailsDetailsTab Theses and Dissertations (All) Archīum Ateneo Monoglycerides -- Synthesis Glycerides -- Synthesis.
institution Ateneo De Manila University
building Ateneo De Manila University Library
continent Asia
country Philippines
Philippines
content_provider Ateneo De Manila University Library
collection archium.Ateneo Institutional Repository
topic Monoglycerides -- Synthesis
Glycerides -- Synthesis.
spellingShingle Monoglycerides -- Synthesis
Glycerides -- Synthesis.
CAYONA, RUEL
Simple and selective synthesis of 1-monolaurin without catalyst
description Glycerol 1-monolaurate, also known popularly as 1-monolaurin, is a monoacylglycerol of lauric acid that has notable antimicrobial properties. It is present in abundant quantities is vegetable oils (i.e. coconut oil). Its most common route of preparation is from lauric acid and glycerol esterification involving chemical catalysts and enzymes. Unfortunately, this reaction is but a messy reaction which generates a mixture of glycerides that is difficult to purify. Significant effort was invested in the development of highly-selective catalysts but by far none is successful at producing 1-monolaurin exclusively as product. In this work, a simple and selective method of synthesis of 1-monolaurin is described that does not involve catalyst but activated reactants, instead. Lauric acid was first converted to lauroyl chloride before it was reacted with a sodium salt of an activated glycerol derivative, sodium glyceroxide. These reactants were allowed to react in a one-pot system and neat (no solvent) condition at room temperature and pressure. The reaction was both kinetically- and thermodynamically-favorable notwithstanding the modest conditions employed. This result was not achieved before with chemical catalysts or enzymes. The present yield may be low (3.41%) but optimization of relevant reaction variables could increase the yield of the target product and prepare the conditions for bulk synthesis. Furthermore, the method is a very promising alternative to high-purity 1-monolaurin preparation and potentially adaptable general procedure for 1-monoacylglycerides.
format text
author CAYONA, RUEL
author_facet CAYONA, RUEL
author_sort CAYONA, RUEL
title Simple and selective synthesis of 1-monolaurin without catalyst
title_short Simple and selective synthesis of 1-monolaurin without catalyst
title_full Simple and selective synthesis of 1-monolaurin without catalyst
title_fullStr Simple and selective synthesis of 1-monolaurin without catalyst
title_full_unstemmed Simple and selective synthesis of 1-monolaurin without catalyst
title_sort simple and selective synthesis of 1-monolaurin without catalyst
publisher Archīum Ateneo
publishDate 2018
url https://archium.ateneo.edu/theses-dissertations/240
http://rizalls.lib.admu.edu.ph/#section=resource&resourceid=1563242681&currentIndex=0&view=fullDetailsDetailsTab
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