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Urea as an Efficient Reagent for the Synthesis of 3-Ethyl-3-(hydroxymethyl)oxetane: A Novel Component in Cationic Ring-Opening Polymerisation

Annby, Ulf ; Rehnberg, Nicola LU orcid ; Samuelsson, Jesper and Teichert, Oliver (2001) In Organic Process Research & Development 5. p.568-571
Abstract
Urea is a very attractive chemical raw material for large-scale production as it combines low cost with virtually unlimited supply and essentially no toxic effects. Here, we present a study on its use in the dehydration of trimethylolpropane with formation of 3-ethyl-3-(hydroxymethyl)oxetane. The reaction consists of carbonylation of trimethylolpropane and subsequent extrusion of carbon dioxide. The first step was run at a temperature of 120−160 °C at a pressure of approximately 300 mmHg for 1−5 h. Most likely, carbamates of TMP constitute the major product. In the latter step, the temperature was increased to 195−215 °C, the pressure was reduced to 10−50 mmHg, and the final product was isolated by distillation. A spiroorthocarbonate of... (More)
Urea is a very attractive chemical raw material for large-scale production as it combines low cost with virtually unlimited supply and essentially no toxic effects. Here, we present a study on its use in the dehydration of trimethylolpropane with formation of 3-ethyl-3-(hydroxymethyl)oxetane. The reaction consists of carbonylation of trimethylolpropane and subsequent extrusion of carbon dioxide. The first step was run at a temperature of 120−160 °C at a pressure of approximately 300 mmHg for 1−5 h. Most likely, carbamates of TMP constitute the major product. In the latter step, the temperature was increased to 195−215 °C, the pressure was reduced to 10−50 mmHg, and the final product was isolated by distillation. A spiroorthocarbonate of TMP was formed as an unexpected by-product. The process has been demonstrated on a multikilogram scale. Toxicological screening revealed 3-ethyl-3-(hydroxy-methyl)oxetane to be irritating to eye but not to skin. (Less)
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type
Contribution to journal
publication status
published
subject
in
Organic Process Research & Development
volume
5
pages
4 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:0035562959
ISSN
1083-6160
DOI
10.1021/op010037j
language
English
LU publication?
no
id
516d8177-4b15-4cf0-9247-3043eb81297a
date added to LUP
2021-10-21 11:23:11
date last changed
2022-02-02 00:44:39
@article{516d8177-4b15-4cf0-9247-3043eb81297a,
  abstract     = {{Urea is a very attractive chemical raw material for large-scale production as it combines low cost with virtually unlimited supply and essentially no toxic effects. Here, we present a study on its use in the dehydration of trimethylolpropane with formation of 3-ethyl-3-(hydroxymethyl)oxetane. The reaction consists of carbonylation of trimethylolpropane and subsequent extrusion of carbon dioxide. The first step was run at a temperature of 120−160 °C at a pressure of approximately 300 mmHg for 1−5 h. Most likely, carbamates of TMP constitute the major product. In the latter step, the temperature was increased to 195−215 °C, the pressure was reduced to 10−50 mmHg, and the final product was isolated by distillation. A spiroorthocarbonate of TMP was formed as an unexpected by-product. The process has been demonstrated on a multikilogram scale. Toxicological screening revealed 3-ethyl-3-(hydroxy-methyl)oxetane to be irritating to eye but not to skin.}},
  author       = {{Annby, Ulf and Rehnberg, Nicola and Samuelsson, Jesper and Teichert, Oliver}},
  issn         = {{1083-6160}},
  language     = {{eng}},
  pages        = {{568--571}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Organic Process Research & Development}},
  title        = {{Urea as an Efficient Reagent for the Synthesis of 3-Ethyl-3-(hydroxymethyl)oxetane: A Novel Component in Cationic Ring-Opening Polymerisation}},
  url          = {{http://dx.doi.org/10.1021/op010037j}},
  doi          = {{10.1021/op010037j}},
  volume       = {{5}},
  year         = {{2001}},
}