The Synthesis of Water-soluble Polymers from Biomass Derivable Platform Molecules

Thomas James Farmer

The Synthesis of Water-soluble Polymers from Biomass Derivable Platform Molecules

Chemistry

Research output: Thesis › Doctoral Thesis

Abstract

This research aimed to demonstrate the potential to produce sustainable water-soluble polymers using platform molecules derivable from biomass. Diesters containing water-solubilising pendants were synthesised by means of esterification and subsequent Michael addition to α,β-unsaturated diacids, itaconic and fumaric acid. Attempts at using these diester monomers in the formation of water-soluble polymers failed, either as a result of pendant loss or due to pendant interaction with the transesterification catalyst. An alternative approach to the synthesis was therefore developed. Formation of α,β-unsaturated polyesters and subsequent Michael addition of pendants successfully generated a group of sustainable biomass derivable polyesters. Moreover, this altered methodology of synthesis offers the potential for a wider selection of biomass derivable polymers to be generated from future research. The unsaturated polyester backbones and the Michael donors used in this research were only a small selection from a larger pool of potential materials and chemicals. This research highlighted the potential of bio-platform molecules, obtainable from biorefineries, to yield polyesters with various properties. Of even greater value was the versatility of the synthetic methodologies (esterification, polytransesterification and Michael addition) that can be applied to the majority of the ‘top bio-platform molecules’ highlighted by the US Department of Energy.

In every synthetic step investigated careful consideration of the greenness and effects of methodology on the environment was given. To this end the use of heterogeneous catalysts, microwave activation, and avoidance of solvents and other auxiliaries was applied throughout, improving the ‘green credentials’ of the final water-soluble polymers obtained.

The family of polyesters produced during this research have the potential to replace current fossil fuel derived equivalents, thus achieving sustainability in the Home and Personal Care market where the environmental impact of products could be used as a powerful marketing tool.

Original language	English
Qualification	Doctor of Philosophy
Awarding Institution	Chemistry
Supervisors/Advisors	MacQuarrie, Duncan James, Supervisor Clark, James Hanley, Supervisor
Thesis sponsors	UNILEVER
Publisher	University of York
Publication status	Published - 2009

Cite this

@phdthesis{698b6e0e0d684597a6424d3f5591ddad,

title = "The Synthesis of Water-soluble Polymers from Biomass Derivable Platform Molecules",

abstract = "This research aimed to demonstrate the potential to produce sustainable water-soluble polymers using platform molecules derivable from biomass. Diesters containing water-solubilising pendants were synthesised by means of esterification and subsequent Michael addition to α,β-unsaturated diacids, itaconic and fumaric acid. Attempts at using these diester monomers in the formation of water-soluble polymers failed, either as a result of pendant loss or due to pendant interaction with the transesterification catalyst. An alternative approach to the synthesis was therefore developed. Formation of α,β-unsaturated polyesters and subsequent Michael addition of pendants successfully generated a group of sustainable biomass derivable polyesters. Moreover, this altered methodology of synthesis offers the potential for a wider selection of biomass derivable polymers to be generated from future research. The unsaturated polyester backbones and the Michael donors used in this research were only a small selection from a larger pool of potential materials and chemicals. This research highlighted the potential of bio-platform molecules, obtainable from biorefineries, to yield polyesters with various properties. Of even greater value was the versatility of the synthetic methodologies (esterification, polytransesterification and Michael addition) that can be applied to the majority of the {\textquoteleft}top bio-platform molecules{\textquoteright} highlighted by the US Department of Energy.In every synthetic step investigated careful consideration of the greenness and effects of methodology on the environment was given. To this end the use of heterogeneous catalysts, microwave activation, and avoidance of solvents and other auxiliaries was applied throughout, improving the {\textquoteleft}green credentials{\textquoteright} of the final water-soluble polymers obtained. The family of polyesters produced during this research have the potential to replace current fossil fuel derived equivalents, thus achieving sustainability in the Home and Personal Care market where the environmental impact of products could be used as a powerful marketing tool. ",

author = "Farmer, {Thomas James}",

year = "2009",

language = "English",

publisher = "University of York",

address = "United Kingdom",

school = "Chemistry",

}

TY - BOOK

T1 - The Synthesis of Water-soluble Polymers from Biomass Derivable Platform Molecules

AU - Farmer, Thomas James

PY - 2009

Y1 - 2009

N2 - This research aimed to demonstrate the potential to produce sustainable water-soluble polymers using platform molecules derivable from biomass. Diesters containing water-solubilising pendants were synthesised by means of esterification and subsequent Michael addition to α,β-unsaturated diacids, itaconic and fumaric acid. Attempts at using these diester monomers in the formation of water-soluble polymers failed, either as a result of pendant loss or due to pendant interaction with the transesterification catalyst. An alternative approach to the synthesis was therefore developed. Formation of α,β-unsaturated polyesters and subsequent Michael addition of pendants successfully generated a group of sustainable biomass derivable polyesters. Moreover, this altered methodology of synthesis offers the potential for a wider selection of biomass derivable polymers to be generated from future research. The unsaturated polyester backbones and the Michael donors used in this research were only a small selection from a larger pool of potential materials and chemicals. This research highlighted the potential of bio-platform molecules, obtainable from biorefineries, to yield polyesters with various properties. Of even greater value was the versatility of the synthetic methodologies (esterification, polytransesterification and Michael addition) that can be applied to the majority of the ‘top bio-platform molecules’ highlighted by the US Department of Energy.In every synthetic step investigated careful consideration of the greenness and effects of methodology on the environment was given. To this end the use of heterogeneous catalysts, microwave activation, and avoidance of solvents and other auxiliaries was applied throughout, improving the ‘green credentials’ of the final water-soluble polymers obtained. The family of polyesters produced during this research have the potential to replace current fossil fuel derived equivalents, thus achieving sustainability in the Home and Personal Care market where the environmental impact of products could be used as a powerful marketing tool.

AB - This research aimed to demonstrate the potential to produce sustainable water-soluble polymers using platform molecules derivable from biomass. Diesters containing water-solubilising pendants were synthesised by means of esterification and subsequent Michael addition to α,β-unsaturated diacids, itaconic and fumaric acid. Attempts at using these diester monomers in the formation of water-soluble polymers failed, either as a result of pendant loss or due to pendant interaction with the transesterification catalyst. An alternative approach to the synthesis was therefore developed. Formation of α,β-unsaturated polyesters and subsequent Michael addition of pendants successfully generated a group of sustainable biomass derivable polyesters. Moreover, this altered methodology of synthesis offers the potential for a wider selection of biomass derivable polymers to be generated from future research. The unsaturated polyester backbones and the Michael donors used in this research were only a small selection from a larger pool of potential materials and chemicals. This research highlighted the potential of bio-platform molecules, obtainable from biorefineries, to yield polyesters with various properties. Of even greater value was the versatility of the synthetic methodologies (esterification, polytransesterification and Michael addition) that can be applied to the majority of the ‘top bio-platform molecules’ highlighted by the US Department of Energy.In every synthetic step investigated careful consideration of the greenness and effects of methodology on the environment was given. To this end the use of heterogeneous catalysts, microwave activation, and avoidance of solvents and other auxiliaries was applied throughout, improving the ‘green credentials’ of the final water-soluble polymers obtained. The family of polyesters produced during this research have the potential to replace current fossil fuel derived equivalents, thus achieving sustainability in the Home and Personal Care market where the environmental impact of products could be used as a powerful marketing tool.

M3 - Doctoral Thesis

PB - University of York

ER -