2,6-Xylidine
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| Chemical formula | C6H3NH2(CH3)2 |
|---|---|
| OTP appearance | colorless to reddish brown liquid |
| Index of refraction | 1.5601 |
| Molar Mass(g/mol) | 121.18 |
| Density(g/cc) | 0.9842 |
| Melting Point(°C) | 11.45 |
| Boiling Point(°C) | 215 |
| NFPA 704 |  0
0
0
|
Uses
Primary
- Feedstock for lidocaine and bupivacaine
Natural occurrence
- Does occur naturally as a trace component of crude oil and/or coal
Hazards
Production
Production
Synthesis
from xylene
2,6-Dimethylaniline is prepared by nitration of m-xylene and reduction, followed by removal of the 2,4-isomer by formation of the acetate salt, removal of the 2,5-isomer by formation of the hydrochloride salt, and recovery of the 2,6-isomer by sublimation.[1]
- For all xylidines, apart from 3,5-xylidine and, to some extent, 2,6-xylidine, reduction of nitroxylenes is the most important industrial production route. The corresponding nitroxylenes can be obtained by nitration of the pure xylenes. If mixtures of isomers are obtained, as with o- and m-xylenes, the nitro compounds can be easily separated by rectification.[2]
via dimethylnitrobenzene
- Prepare solution to 0.033 mol 2,6-dimethyl-nitrobenzene in 50 mL glacial acetic acid
- Dissolve 0.1 mol of tin (II) chloride dihydrate (SnCl2•2H2O) in 40 mL concentrated hydrochloric acid
- Combine solutions
- Mix thoroughly and let stand for 15 minutes
- Cool the reaction mixture and collect the precipitate that has formed by vacuum filtration
- Place the product in another flask, add 25 mL water and make solution strongly basic by adding 40-50 mL 8 M potassium hydroxide solution
- Cool solution to RT, extract aqueous mixture first with a 25 mL portion then an additional 10 mL portion of diethyl ether
- Combine the ether extracts, wash this solution twice with two 10 mL portions of water and dry it over anhydrous potassium carbonate
- Filter solution with gravity filtration and remove ether by simple distillation
- Transfer and weigh the 2,6-Xylidine
via xylenol
Combine 2,6-xylenol with ammonia in the vapor phase over a catalyst at high pressures and temperatures[3]
- C6H3(CH3)2(OH) + NH3{Al2O3C6H3(CH3)2(NH2) + H2O400-430°C; 90-220atm}→
Testing
Purification
Storage
Disposal
See Also
References
- ↑ 2,6-Xylidine
courtesy TOXNET, NIH. - ↑ Meyer, M "Xylidines".
Ullmann's Encyclopedia of Industrial Chemistry 7th ed. (1999-2016) John Wiley & Sons - ↑ US patent 4609760 "Process for the preparation of 2,6-xylidine"
Link courtesy Google