volume 16 issue 7 pages 1273-1278

Sulfolane: A Versatile Dipolar Aprotic Solvent

Ulf Tilstam 1
1
 
CMC-Solutions, Overhemstraat 3, B-3320 Hoegaarden, Belgium
Publication typeJournal Article
Publication date2012-07-03
scimago Q1
wos Q1
SJR0.865
CiteScore5.4
Impact factor3.5
ISSN10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Sulfolane is a highly stable and attractive alternative to other more common dipolar aprotic solvents such as DMSO, DMF, DMAC, and NMP. Sulfolane is more toxic than the other solvents but has a very low skin penetration in comparison to that of the others. A high skin penetration is not beneficial for organic solvents as dissolved toxic compounds might be transferred through the skin. Sulfolane has a high dipole moment (μ = 4.7 debye), elevated relative permittivity (eυ = 43.4), and a high Hildebrand solubility parameter (δ = 27.2 [MPa]1/2). This means a high solvency power for reactions containing polarizable intermediates. Sulfolane is capable of strong solvation of cations by the oxygens in the sulfone group which increases the nucleophilicity of the corresponding less solvated anions. With its high stability against strong acids and bases as well as its thermal stability sulfolane is a solvent that can be operated within a wide range of reaction conditions. This makes it the solvent of choice for diff...
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GOST Copy
Tilstam U. Sulfolane: A Versatile Dipolar Aprotic Solvent // Organic Process Research and Development. 2012. Vol. 16. No. 7. pp. 1273-1278.
GOST all authors (up to 50) Copy
Tilstam U. Sulfolane: A Versatile Dipolar Aprotic Solvent // Organic Process Research and Development. 2012. Vol. 16. No. 7. pp. 1273-1278.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/op300108w
UR - https://doi.org/10.1021/op300108w
TI - Sulfolane: A Versatile Dipolar Aprotic Solvent
T2 - Organic Process Research and Development
AU - Tilstam, Ulf
PY - 2012
DA - 2012/07/03
PB - American Chemical Society (ACS)
SP - 1273-1278
IS - 7
VL - 16
SN - 1083-6160
SN - 1520-586X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Tilstam,
author = {Ulf Tilstam},
title = {Sulfolane: A Versatile Dipolar Aprotic Solvent},
journal = {Organic Process Research and Development},
year = {2012},
volume = {16},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/op300108w},
number = {7},
pages = {1273--1278},
doi = {10.1021/op300108w}
}
MLA
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MLA Copy
Tilstam, Ulf. “Sulfolane: A Versatile Dipolar Aprotic Solvent.” Organic Process Research and Development, vol. 16, no. 7, Jul. 2012, pp. 1273-1278. https://doi.org/10.1021/op300108w.