4-Nonanoylmorpholine
From Wikipedia, the free encyclopedia
| 4-Nonanoylmorpholine | |
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| IUPAC name | 4-Nonanoylmorpholine |
| Other names | 4-(1-Oxononyl)morpholine, N-Nonanoylmorpholine, 1-(4-Morpholino)-1-nonanone, 4-Morpholinenonylic acid, Pelargonic acid morpholide, Pelargonic morpholide, N-Morpholino nonanamide, 1-Morpholin-4-ylnonan-1-one, MPA, MPK |
| Identifiers | |
| CAS number | [5299-64-9] |
| PubChem | |
| SMILES | CCCCCCCCC(=O)N1CCOCC1 |
| InChI | 1/C13H25NO2/c1-2-3-4-5-6-7-8- 13(15)14-9-11-16-12-10-14/h2-12H2,1H3 |
| Properties | |
| Molecular formula | C13H25NO2 |
| Molar mass | 227.34 g/mol |
| Appearance | Liquid |
| Boiling point |
310 - 315 °C |
| Solubility in water | Insoluble |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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4-Nonanoylmorpholine (pelargonic acid morpholide, N-nonanoylmorpholine, MPK or МПК (for морфолид пеларгоновой кислоты), or MPA) is an amide of pelargonic acid and morpholine.
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[edit] Properties
4-Nonanoylmorpholine was first synthetized in 1954 by L.M. Rice, from morpholine and chloroanhydride of pelargonic acid.
It is a liquid insoluble in water and soluble in polar organic solvents (eg. acetone, propanol, dimethyl formamide, and benzene) and fats. Its volatility is 27 mg/m3 at 20 °C and 43 mg/m3 at 35 °C.
[edit] Uses
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This section needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (November 2007) |
It is a used as a solvent in lachrymatory formulations containing CR gas or CS gas. It is reported to be effective against dogs and starts being effective in concentrations of over 20-40 mg.min/m3. It is considered very safe, with high differences between effective and toxic concentrations. At one time it was reportedly used as food seasoning with no reported adverse effects. However, its effectiveness when used alone is rather low even in the highest permitted concentration, so it is almost always used in combination with CR gas or CS gas commonly referred to as tear gas. In that combination, this blend is effective even against dogs and people under influence of alcohol or drugs. Its effect usually lasts for 15-30 minutes.
MPK blends withCR gas or CS gasare common personal self-defense chemical agents in Russia and Ukraine, but is virtually unknown elsewhere.
[edit] Natural occurrence
4-Nonanoylmorpholine naturally occurs as a pheromone of Aedes aegypti mosquitoes.[1]
[edit] References
- Collum D.B., Chen S.-C., Ganem B. (1978). "A new synthesis of amides and macrocyclic lactams" ([dead link]). J. Org. Chem. 43 (22): 4393–4394(2). doi:.
