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Studies of diethylenetriaminepentaacetic acid degradation in pulp mill process liquors

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Blackwell, Damien Mark (1998) Studies of diethylenetriaminepentaacetic acid degradation in pulp mill process liquors. Research Master thesis, University of Tasmania.

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Abstract

The general focus of this study was to synthesise 1-(carboxymethyl)-4-[2-
[bis(carboxymethyl)amino]ethyl]-2-oxopiperazine (1a), a cyclic degradation
product of diethylenetriaminepentaacetic acid (DTPA) present in pulping liquors,
and then determine its complexing ability with metal ions of relevance to the
paper industry.
Three independent but related methods were developed for the preparation of 1a,
although ultimately it was necessary to fully develop only one. In this method, 2-
chloroethyliminodiacetonitrile was prepared by Mannich's reaction of 2-
chloroethylamine, formaldehyde and potassium cyanide and converted to dimethyl
2-chloroethyliminodiacetate by treatment with gaseous HC1 in methanol.
Alkylation of 1-methoxycarbonylmethyl-2-oxopiperazine with dimethyl 2-
chloroethyliminodiacetate produced 1-(methoxycarbonylmethyl)-4-[2-
[bis(methoxycarbonylmethyl)amino]ethyl]-2-oxopiperazine, which when
hydrolysed in acidic solution gave the trihydrochloride salt of 1a. The overall
yield of 1a trihydrochloride (via 1-methoxycarbonylmethyl-2-oxopiperazine) was
20%. Using this new method, sufficient quantities of 1a were synthesised for both
characterisation and complexing studies.

Item Type: Thesis (Research Master)
Keywords: Wood-pulp industry, Diethylenetriaminepentaacetic acid, Pulping
Copyright Holders: The Author
Copyright Information:

Copyright 1998 the Author – The University is continuing to endeavour to trace the copyright owner(s) and in the meantime this item has been reproduced here in good faith. We would be pleased to hear from the copyright owner(s).

Additional Information:

Thesis (M.Sc.)--University of Tasmania, 1998. Includes bibliographical references

Date Deposited: 25 Nov 2014 00:48
Last Modified: 04 May 2016 00:48
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