Sulfolane: A Versatile Dipolar Aprotic Solvent
1
CMC-Solutions, Overhemstraat
3, B-3320 Hoegaarden, Belgium
|
Publication type: Journal Article
Publication date: 2012-07-03
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 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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163
Total citations:
163
Citations from 2024:
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(17%)
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GOST
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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)
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Tilstam U. Sulfolane: A Versatile Dipolar Aprotic Solvent // Organic Process Research and Development. 2012. Vol. 16. No. 7. pp. 1273-1278.
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RIS
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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 -
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BibTex (up to 50 authors)
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@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}
}
Cite this
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.