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1-Methylpiperidine
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Structural formula of 1-methylpiperidine.svg 100px 1-Methylpiperidine N-methylpiperidine 626-67-5 281417 11788 210-959-9 5522 12291 617374QZN4 2399 1S/C6H13N/c1-7-5-3-2-4-6-7/h2-6H2,1H3 PAMIQIKDUOTOBW-UHFFFAOYSA-N CN1CCCCC1
C6H13N 99.18 g·mol−1 0.82 g·cm−3 (20 °C)
N-Methylpiperidine https://pubchem.ncbi.nlm.nih.gov/compound/12291#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 02 05 06 07 Danger H225 H301 H302 H311 H312 H314 H331 H412 P210 P233 P240 P241 P242 P243 P260 P262 P264 P264+P265 P270 P271 P273 P280 P301+P316 P301+P317 P301+P330+P331 P302+P352 P302+P361+P354 P303+P361+P353 P304+P340 P305+P354+P338 P316 P317 P321 P330 P361+P364 P362+P364 P363 P370+P378 P403+P233 P403+P235 P405 P501
1-Methylpiperidine (IUPAC nomenclature) is an organic chemical compound belonging to the group of cyclic compounds and tertiary amines. The compound serves as a starting material for organic syntheses and for the production of catalyst systems.
Extraction and preparation
For the industrial production of 1-methylpiperidine, 5-amino-1-pentanol is reacted with methanol at 180–230 °C and 70–120 bar in the presence of an aluminum oxide-supported copper oxide catalyst. EP 2582669 Verfahren zur Herstellung eines zyklischen tertiären Methylamins 2015-10-07 Christof Wilhelm Wigbers Johann-Peter Melder Bernd Stein Harald Meissner BASF SE
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The reaction is performed in the liquid phase in a continuous tubular or multi-tubular reactor. The catalyst is arranged as a fixed bed reactor, through which the reaction mixture can flow from either below or above. The product is purified by multistage distillation.
Properties
Physical properties
1-Methylpiperidine has a relative density of 3.42 (density ratio to dry air at the same temperature and pressure) and a relative density of the vapor–air mixture of 1.10 (density ratio to dry air at 20 °C and under standard conditions). The dynamic viscosity at 20 °C is 5 mPa·s.1-Methylpiperidin 70310 626-67-5 2024-01-02
Chemical properties
1-Methylpiperidine is a highly flammable, colorless liquid with an amine-like odor. The compound belongs to the class of cyclic, tertiary amines and can also be considered a heterocyclic compound. N-Methylpiperidine is miscible with water and exhibits strong reactivity as an aqueous alkaline solution. At 20 °C, an aqueous solution of the compound (concentration: 100 g/l) has a pH value of 12. Violent reactions may occur with acids and oxidizing agents.
Use
1-Methylpiperidine is used, among other applications, as an intermediate in the production of the growth regulator mepiquat chloride.Roose Peter Amines, Aliphatic 2015-09-30 Ullmann's Encyclopedia of Industrial Chemistry 1–55 Wiley-VCH 10.1002/14356007.a02_001.pub2 978-3-527-30385-4 Eller Karsten Henkes Erhard Rossbacher Roland Höke Hartmut It is also used as a solvent and in the synthesis of other chemicals. Furthermore, 1-methylpiperidine serves as a reagent for the synthesis of catalyst systems based on ruthenium. It is also employed in the preparation of antibacterial imidazoleium, pyrroleidinium and piperidine salts.
Safety information
The vapors of 1-methylpiperidine form explosive mixtures with air. The substance is primarily absorbed via the respiratory tract. Significant absorption through the skin is also suspected. Ingestion or exposure causes acute irritation of the mucous membrane of the eye, the respiratory tract, and the skin. No chronic data are available for humans. Reproductive toxicity could not be demonstrated in animal studies, but no corresponding human data exist. No detailed information is available on mutagenicity or carcinogenicity. 1-Methylpiperidine has a lower explosion limit (LEL) of 1.1 % by volume and an upper explosion limit (OEL) of 9.9 % by volume. The ignition temperature is 205 °C, placing the substance in temperature class T3. With a flash point of 3 °C, 1-methylpiperidine is considered highly flammable. The compound is also classified as highly hazardous to the aquatic environment.
References
Category:Piperidines
Category:Tertiary amines