Chemical Properties
Colorless oily liquid, melting point-5.8℃, boiling point 144℃（139-141℃，145.6-145.8℃）, density 0.9252（20/4℃）, refractive index 1.4977, flash point 33℃, soluble in dimethyl formamide, tetrahydrofuran, cold water, hot water, ethanol and ether, with mixed odor of Pyridine and mint.
Usage
2,6-Lutidine is widely used in organic synthesis as a raw material and solvent. In Pharmaceutical industry, it can be used for the production of antiatherosclerotic pyridinolcarbamate. It can also be used for the production of Cortisone acetate, hydrocortisone, niacin, lobeline and stilbazium iodide which is an anthelmintic and effective for the worm, fasciolopsis buski, whipworm, pinworm and so on. In addition, 2,6-Lutidine can be used as an auxiliaries for Pesticides, dyes, dyeing and printing and used as resin and rubber accelerator, intermediate of hot oil stabilizer. It can be oxidized to produce Dimethyl pyridine acid, which can be used as the stabilizer for hydrogen peroxide and acetic acid and used to synthesize lobelidine. 2,6-Lutidine is used as various kinds of nutty essence and cocoa, coffee, meat, bread and vegetable typed essence. It is also used to synthesize drugs for the treatment and first-aid of hypertension.
Preparation
2,6-Lutidine is obtained through the separation of β-methylpyridine which is a recycled product of coal coking byproduct.
Category
flammable liquid
Toxicity grade
high toxic
Acute toxicity
oral – rat LD50: 400mg/kg
Flammability hazard characteristics
flammable in case of fire, high temperature and oxidant, releasing toxic nitrogen oxides in case of heat.
Storage
Ventilated and dry warehouse with low temperature, separated from acids.
Fire extinguishing agents
Dry powder, dry sand, carbon dioxide, foam.
Chemical Properties
2,6-Dimethylpyridine has a powerful and diffusive minty-tarry odor. It has also been described to have the odor of
pyridine and peppermint
Chemical Properties
Colorless to yellow liquid
Occurrence
Reported found in bread, tea, peppermint oil, cheeses, chicken, beef, pork, beer, sherry, whiskies, cocoa, coffee, tea, oatmeal, rice bran, buckwheat and malt.
Uses
2,6-Lutidine is used as a solvent in organic synthesis and as a sterically hindered mild base. It is also used as a vulcanization accelerator for dyes, resins and rubber. It also acts as a food additive.
Uses
Isolated from the basic fraction of coal tar. A semi-volatile compound in tobacco.
Definition
ChEBI: A member of the class of methylpyridines that is pyridine carrying methyl substituents at positions 2 and 6.
Taste threshold values
Taste characteristics at 20 ppm: nutty, coffee, cocoa, musty, bready and meaty
General Description
A colorless liquid with a peppermint odor. Flash point 92°F. Less dense than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.
Air & Water Reactions
Highly flammable. Soluble in water.
Reactivity Profile
2,6-Lutidine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Flammability and Explosibility
Flammable
Synthesis
Synthesis from ethyl acetoacetate, formaldehyde and ammonia; isolated from basic fraction of coal tar
Purification Methods
Likely contaminants include 3-and 4-picoline (similar boiling points). However, they are removed by using BF3, with which they react preferentially, by adding 4mL of BF3 to 100mL of dry fractionally distilled 2,6-lutidine and redistilling. Distillation of commercial material from AlCl3 (14g per 100mL) can also be used to remove picolines (and water). Alternatively, lutidine (100mL) can be refluxed with ethyl benzenesulfonate (20g) or ethyl p-toluenesulfonate (20g) for 1hour, then the upper layer is cooled, separated and distilled. The distillate is refluxed with BaO or CaH2, then fractionally distilled through a glass helices-packed column. 2,6-Lutidine can be dried with KOH or sodium or by refluxing with (and distilling from) BaO, prior to distillation. For purification via its picrate, 2,6-lutidine, dissolved in absolute EtOH, is treated with an excess of warm ethanolic picric acid. The precipitate is filtered off, recrystallised from acetone (to give m 163-164.5o (166-167o), and partitioned between ammonia and CHCl3/diethyl ether. The organic layer, after washing with dilute aqueous KOH, is dried with Na2SO4 and fractionally distilled. [Warnhoff J Org Chem 27 4587 1962.] Alternatively, 2,6-lutidine can be purified via its urea complex, as described under 2,3-lutidine. Other purification procedures include azeotropic distillation with phenol [Coulson et al. J Appl Chem (London) 2 71 1952], fractional crystallisation by partial freezing, and vapour-phase chromatography using a 180-cm column of polyethylene glycol-400 (Shell, 5%) on Embacel (May and Baker) at 100o, with argon as carrier gas [Bamford & Block J Chem Soc 4989 1961]. The hydrochloride has m 235-237o, 239o (from EtOH). [Beilstein 20 II 160, 20 III/IV 2776, 20/6 V 32.]
