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| | Mesityl oxide Chemical Properties |
| Melting point | −53 °C(lit.) | | Boiling point | 129 °C(lit.) | | density | 0.858 g/mL at 25 °C(lit.) | | vapor pressure | 10.5 hPa (20 °C) | | FEMA | 3368 | 4-METHYL-3-PENTEN-2-ONE | | refractive index | n20/D 1.442(lit.) | | Fp | 87 °F | | storage temp. | Store below +30°C. | | solubility | 30g/l | | form | Liquid, Free Of Suspended Matter | | color | Clear | | Odor | Strong; peppermint; honeylike. | | explosive limit | 1.4-10.1%(V) | | Odor Type | vegetable | | Water Solubility | 28 G/L (20 ºC) | | Merck | 14,5908 | | JECFA Number | 1131 | | BRN | 1361550 | | Henry's Law Constant | (x 10-6 atm?m3/mol):
4.01 at 20 °C (approximate - calculated from water solubility and vapor pressure) | | Exposure limits | TLV-TWA 60 mg/m3 (15 ppm) (ACGIH),
10-h TWA 40 mg/m3 (10 ppm) (NIOSH);
STEL 100 mg/m3 (25 ppm); IDLH 5000
ppm. | | Stability: | Light Sensitive | | LogP | 1.37 at 20℃ | | CAS DataBase Reference | 141-79-7(CAS DataBase Reference) | | NIST Chemistry Reference | 3-Penten-2-one, 4-methyl-(141-79-7) | | EPA Substance Registry System | Mesityl oxide (141-79-7) |
| Hazard Codes | Xn | | Risk Statements | 10-20/21/22-36/37/38 | | Safety Statements | 25 | | RIDADR | UN 1229 3/PG 3 | | WGK Germany | 1 | | RTECS | SB4200000 | | Autoignition Temperature | 344 °C | | TSCA | Yes | | HS Code | 2914 19 90 | | HazardClass | 3 | | PackingGroup | III | | Hazardous Substances Data | 141-79-7(Hazardous Substances Data) | | Toxicity | LD50 in mice (mg/kg): 710 ±85 intragastric; LC50 in mice (2 hr), rats (4 hr) (mg/m3): 10000 ±270, 9000 ±600 (Ismerov) | | IDLA | 1,400 ppm [10% LEL] |
| | Mesityl oxide Usage And Synthesis |
| Description | Mesity oxide(141-79-7) is a tri-functional intermediate of considerable utility in the synthesis of a number of different types of organic compounds, such as mesityl oxide can be hydrogenated to methyl isobutyl ketone and other flavor ingredients in foods, such as 4- methyl-pentanone. Mesityl oxide can be used as a solvent for resins, gums, nitrocellulose, oils, lacquers, and inks. It is also used as an insect repellant and used in ore flotation.
| | References | [1] Pradyot Patnaik, A Comprehensive Guide to the Hazardous Properties of Chemical Substances, 3rd Edition, 2007
[2] Klaus Weissermel, and Hans-Jürgen Arpe, Industrial Organic Chemistry, 3rd Edition, 1997
[3] George A. Burdock, Fenaroli’s Handbook of Flavor Ingredients, 4th Edition, 2001
| | Description | The commercial grade of 4-methyl-3-penten-2-one exhibits an unpleasant grassy-green or pungent, acrylic odor. The pure material has a pleasant, honey-like odor. This substance may be prepared by reacting acetone or diacetone alcohol with iodine or other dehydrating agent; by condensation of acetone over sulfonated polystyrene-divinylbenzene resin used as an ion exchange catalyst. | | Chemical Properties | Mesityl oxide is a clear, pale yellow, or colorless liquid with a strong peppermint odor. The odor threshold is 0.05 ppm. | | Physical properties | Clear, pale yellow liquid with a strong, peppermint, or honey-like odor. Experimentally
determined detection and recognition odor threshold concentrations were 70 μg/m3 (17 ppbv) and
200 μg/m3 (50 ppbv), respectively (Hellman and Small, 1974). | | Occurrence | Reported found in orange juice, baked potato, bell pepper, sauerkraut, tomato, crisp bread, parmesan cheese,
milk, chicken fat, hop oil, rum, coffee, tea, peanut, passion fruit, mushroom, tamarind, prickly pear, buckwheat, basil, elder flower,
rosemary, shrimp, nectarine, clam and maté | | Uses | Mesityl oxide is used as a solvent for resins,gums, nitrocellulose, oils, lacquers, and inks;as an insect repellant; and in ore flotation.. | | Uses | Solvent for nitrocellulose, many gums and resins, particularly vinyl resins. In lacquers, varnishes and enamels. In making methyl isobutyl ketone. | | Preparation | By reacting acetone or diacetone alcohol with iodine or other dehydrating agent; by condensation of acetone over sulfonated polystyrene-divinylbenzene resin used as an ion exchange catalyst. | | Definition | ChEBI: 4-Methyl-3-penten-2-one, 9CI is an olefinic compound. It is functionally related to an acrylic acid. | | Synthesis Reference(s) | Tetrahedron Letters, 27, p. 3733, 1986 DOI: 10.1016/S0040-4039(00)83866-6 | | General Description | Mesityl oxide appears as a colorless, oily liquid with a pungent honey-like odor. Flash point 87 °F. Less dense than water and slightly soluble in water. Vapors heavier than air. Used in paint removers, as a solvent for plastics, and as an insect repellent. | | Air & Water Reactions | Highly flammable. Slightly soluble in water | | Reactivity Profile | Mixing MESITYL OXIDE in equal molar proportions with any of the following substances in a closed container caused the temperature and pressure to increase: 2-aminoethanol, chlorosulfonic acid, ethylene diamine, nitric acid, oleum, or sulfuric acid [NFPA 1991]. | | Hazard | Flammable, moderate fire risk. Toxic by
ingestion, inhalation, and skin absorption. Eye and
upper respiratory tract irritant, central nervous system impairment. | | Health Hazard | Inhalation causes irritation of nose and throat, headache, dizziness, difficult breathing. Contact with liquid or concentrated vapor causes severe eye irritation. Liquid irritates skin. Ingestion causes irritation of mouth and stomach. | | Health Hazard | Mesityl oxide is a moderately toxic substance, more toxic than the saturated ketones.Inhalation of its vapors can cause irritationto the eyes, skin, and mucous membranes. Inhumans, the irritation effect on the eyes andnose are reported to be 25 and 50 ppm. Athigh concentrations narcosis can result. Otherthan narcosis, prolonged exposure to highconcentrations can injure the lungs, liver, and kidney. A concentration of 2500 ppm waslethal to rats.
LD50 value, oral (rats): 1120 mg/kg. | | Fire Hazard | Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. | | Safety Profile | Poison by
intraperitoneal route. Moderately toxic by
ingestion. Mildly toxic by inhalation and skin
contact. Human systemic effects by
inhalation: conjunctiva irritation. This
compound is highly irritating to all tissues
on contact; its vapors also are irritating.
High concentrations are narcotic. It is
readdy absorbed through intact skin. Single
exposures tend to indicate that ths ketone
has greater acute and narcotic action than
isophorone. It can have harmful effects
upon the hdneys and liver, and may damage
the eyes and lungs to a serious degree.
Prolonged exposure can injure liver, kidneys,
and lungs. It can cause opaque cornea,
keratoconus, and extensive necrosis of
cornea. Dangerous fire hazard when
exposed to heat, sparks, or flame; can react
with oxidzing materials. Reacts violently
with 2-amino ethanol, chlorosulfonic acid,
ethylene diamine, HNO3, oleum, H2SO4. An
insect repellent. To fight fire, use alcohol
foam, CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also KETONES. | | Potential Exposure | Mesityl oxide is used as a solvent for
cellulose esters and ethers and other resins in lacquers and
inks. It is used in paint and varnish removers and as an
insect repellent | | Shipping | UN1229 Mesitly oxide, Hazard Class: 3; Labels:
3-Flammable liquid.
| | Purification Methods | Purify it by distillation, preferably in a vacuum or via the semicarbazone (m 165o) which is decomposed to pure ketone. The 2,4-dinitrophenylhydrazone (m 205-206o) crystallises from EtOH. [Johnson J Am Chem Soc 73 5888 1951, Johnson J Am Chem Soc 75 2720 1953, Erskine & Waight J Chem Soc 3425 1960, Beilstein 1 H 736, 1 I 382, 1 II 793, 1 III 2995, 1 IV 3471.] | | Incompatibilities | May form explosive mixture with air.
May be able to form explosive peroxides. May react
violently with nitric acid; aliphatic amines; alkanolamines, 2-
aminoethanol, ethylene diamine; chlorosulfonic acid; oleum
(fuming sulfuric acid). Not compatible with oxidizers, strong
acids; strong bases; reducing agents; halogens. Dissolves
some forms of plastics, resins and rubber. Attacks copper.
| | Waste Disposal | Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be observed. |
| | Mesityl oxide Preparation Products And Raw materials |
| Raw materials | Diacetone Alcohol-->2,6-Dimethyl-4-heptanone-->4-Methyl-3-penten-2-one oxime-->2-Pentanone, 4-chloro-4-methyl--->3,4-epoxy-4-methylpentan-2-one-->2-Heptanone, 4-hydroxy--->4-Methyl-4-(methylnitrosoamino)-2-pentanone-->4-METHYL-3-PENTEN-2-OL-->Ethoxyquin-->Phenetidine-->Cyclopropane, 2-bromo-1,1-dimethyl-3-methylene- | | Preparation Products | ADS-->4,4-DIMETHYL-2-PENTANONE-->Delta Damascone-->Damascenone-->4-AMINO-4-METHYL-2-PENTANONE HYDROGENOXALATE-->2,2,3,3-tetramethylhexane-->2,2,4,4,6-pentamethyl-hexahydropyrimidine-->7-Quinolinol, 1-ethyl-1,2-dihydro-2,2,4-trimethyl- |
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