Urea as an Efficient Reagent for the Synthesis of 3-Ethyl-3-(hydroxymethyl)oxetane: A Novel Component in Cationic Ring-Opening Polymerisation
(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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- author
- Annby, Ulf ; Rehnberg, Nicola LU ; Samuelsson, Jesper and Teichert, Oliver
- publishing date
- 2001-11
- 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}}, }