Dimethylformamide: Difference between revisions

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m clean up, replaced: Ichthyal → fishy using AWB
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| O = 1
| Appearance = Colourless liquid
| Odor = Ichthyalfishy, ammoniacal
| Density = 948 mg mL<sup>−1</sup>
| MeltingPtK = 212.7
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DMF is miscible with water in all proportions.<ref name=bipp>{{ Ullmann | author = Bipp, H.; Kieczka, H. | title = Formamides | doi = 10.1002/14356007.a12_001.pub2 }}</ref> The vapour pressure at 20°C is 3.5hPa.<ref>IPCS (International Programme on Chemical Safety) (1991). Environmental Health Criteria 114 “Dimethylformamide” United Nations Environment Programme, International Labour Organisation, World Health Organization; 1–124.</ref> A [[Henry's law]] constant of 7.47×10<sup>−5</sup> hPa·m<sup>3</sup>/mol can be deduced from an experimentally determined equilibrium constant at 25 °C.<ref>{{ cite journal | author = Taft, R. W.; Abraham, M. H.; Doherty, R. M.; Kamlet, M. J. | title = The molecular properties governing solubilities of organic nonelectrolytes in water | journal = Nature | year = 1985 | volume = 313 | issue = 6001 | pages = 384–386 | doi = 10.1038/313384a0 }}</ref> The [[partition coefficient]] logPOW is measured to −0.85.<ref>(BASF AG, department of analytical, unpublished data, J-No. 124659/08, 27.11.1987)</ref> Since the density of DMF (0.95 g/cm<sup>3</sup> at 20 °C<ref name=bipp/>) is very similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.
 
[[File:DMF resonances.png|thumb|left|400px|The two resonance forms of DMF]]{{ClearleftClear left}}
 
==Production==
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*It is also a common catalyst used in the synthesis of [[acyl halides]], in particular the synthesis of [[acyl chlorides]] from [[carboxylic acids]] using [[oxalyl chloride|oxalyl]] or [[thionyl chloride]].<ref name = clayden>{{ cite book | author = Clayden, J. | title = Organic Chemistry | publisher = Oxford University Press | location = Oxford | year = 2001 | pages = 276–296 | isbn = 0-19-850346-6 }}</ref>
*DMF penetrates most [[plastics]] and makes them [[Swelling (medical)|swell]]. This property makes it very suitable for [[solid phase peptide synthesis]]. It also frequently occurs as a component of [[paint strippers]] for this purpose.
*DMF is very effective at separating and suspending [[carbon nanotubes]], and is recommended by the [[National Institute of Standards and Technology|NIST]] for use in [[near infrared spectroscopy]] of such.<ref name=miiswcn>{{ cite book | author = Haddon, R.; Itkis, M. | editor = Freiman, S.; Hooker, S.; Migler; K.; Arepalli, S. | title = Publication 960-19 Measurement Issues in Single Wall Carbon Nanotubes | chapter = 3. Near-Infrared (NIR) Spectroscopy | publisher = NIST | year = 2008 | month = March | url = http://www.nist.gov/customcf/get_pdf.cfm?pub_id=852726 | format = pdf | page = 20 | accessdate = 2012-06-28 }}</ref>
*DMF can be utilized as a standard in proton NMR allowing for a quantitative determination of an unknown chemical.
*DMF is used as a solvent to recover [[olefins]] such as [[1,3-butadiene]] via [[extractive distillation]].