2,6-Lutidine
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| Names | |
|---|---|
| Preferred IUPAC name
2,6-Dimethylpyridine | |
| Other names
Lutidine | |
| Identifiers | |
| 3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.262 |
| PubChem CID |
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| UNII | |
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| Properties | |
| C7H9N | |
| Molar mass | 107.153 g/mol |
| Appearance | Clear oily liquid |
| Density | 0.9252 |
| Melting point | −5.8 °C (21.6 °F; 267.3 K) |
| Boiling point | 144 °C (291 °F; 417 K) |
| 27.2% at 45.3 °C | |
| Acidity (pKa) | 6.60[2] |
| -71.72·10−6 cm3/mol | |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is  ?) | |
| Infobox references | |
2,6-Lutidine is a natural heterocyclic aromatic organic compound with the formula (CH3)2C5H3N. It is one of several dimethyl-substituted derivative of pyridine. It is a colorless liquid with mildly basic properties and a pungent, noxious odor.
Occurrence and production
It is produced industrially by the reaction of formaldehyde, acetaldehyde, and ammonia.[3] It was isolated from the basic fraction of coal tar and from bone oil.[1] It has been detected in waste water from oil shale processing sites and former creosoting facilities.
Uses
2,6-Lutidine has been evaluated for use as a food additive owing to its nutty aroma when present in solution at very low concentrations.[4]
Due to the steric effects of the two methyl groups, 2,6-lutidine is only weakly nucleophilic. It is moderately basic, with a pKa of 6.60.[2] In organic synthesis, 2,6-lutidine is thus sometimes used as a sterically hindered mild base.
Biodegradation
Though pyridine is an excellent source of carbon, nitrogen, and energy for certain microorganisms, methylation significantly retards degradation of the pyridine ring. 2,6-Lutidine was found to be significantly more resistant to microbiological degradation than any of the picoline isomers or 2,4-lutidine in soil.[5] Significant volatilization loss was observed in liquid media. Estimated time for complete degradation was > 30 days.[6]
See also
References
- 1 2 Merck Index, 11th Edition, 5485.
- 1 2 Zvi Rappoport: CRC Handbook of Tables for Organic Compound Identification, Third Edition, CRC Press, Boca Raton, Florida, 1984, ISBN 0-8493-0303-6, p. 438.
- ↑ Shinkichi Shimizu, Nanao Watanabe, Toshiaki Kataoka, Takayuki Shoji, Nobuyuki Abe, Sinji Morishita, Hisao Ichimura "Pyridine and Pyridine Derivatives" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; John Wiley & Sons: New York. doi: 10.1002/14356007.a22_399
- ↑ Sims, G. K. and E.J. O'Loughlin. 1989. Degradation of pyridines in the environment, CRC Critical Reviews in Environmental Control. 19(4): 309–340.
- ↑ Sims, G. K.; L.E. Sommers (1985). "Degradation of pyridine derivatives in soil". Journal of Environmental Quality. 14: 580–584.
- ↑ Sims, G. K. and L.E. Sommers. 1986. Biodegradation of pyridine derivatives in soil suspensions. Environmental Toxicology and Chemistry. 5: 503–509.