Mesityl oxide

Mesityl oxide Basic information
Description References
Product Name:Mesityl oxide
Synonyms:Mesityloxide 0;Mesityl oxide technical grade, 90%;Isopropylideneacetone 4-Methyl-3-penten-2-one;4-METHYL-3-PENTENE-2-ONE;AKOS BBS-00004339;femanumber3368;isobutenylmethylketone;isopropylidene-aceton
CAS:141-79-7
MF:C6H10O
MW:98.14
EINECS:205-502-5
Product Categories:Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Acetone series
Mol File:141-79-7.mol
Mesityl oxide Structure
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
OdorStrong; peppermint; honeylike.
explosive limit1.4-10.1%(V)
Odor Typevegetable
Water Solubility 28 G/L (20 ºC)
Merck 14,5908
JECFA Number1131
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 limitsTLV-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
LogP1.37 at 20℃
CAS DataBase Reference141-79-7(CAS DataBase Reference)
NIST Chemistry Reference3-Penten-2-one, 4-methyl-(141-79-7)
EPA Substance Registry SystemMesityl oxide (141-79-7)
Safety Information
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 Temperature344 °C
TSCA Yes
HS Code 2914 19 90
HazardClass 3
PackingGroup III
Hazardous Substances Data141-79-7(Hazardous Substances Data)
ToxicityLD50 in mice (mg/kg): 710 ±85 intragastric; LC50 in mice (2 hr), rats (4 hr) (mg/m3): 10000 ±270, 9000 ±600 (Ismerov)
IDLA1,400 ppm [10% LEL]
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Mesityl oxide Usage And Synthesis
DescriptionMesity 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

DescriptionThe 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 PropertiesMesityl oxide is a clear, pale yellow, or colorless liquid with a strong peppermint odor. The odor threshold is 0.05 ppm.
Physical propertiesClear, 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).
OccurrenceReported 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
UsesMesityl oxide is used as a solvent for resins,gums, nitrocellulose, oils, lacquers, and inks;as an insect repellant; and in ore flotation..
UsesSolvent for nitrocellulose, many gums and resins, particularly vinyl resins. In lacquers, varnishes and enamels. In making methyl isobutyl ketone.
PreparationBy 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.
DefinitionChEBI: 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 DescriptionMesityl 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 ReactionsHighly flammable. Slightly soluble in water
Reactivity ProfileMixing 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].
HazardFlammable, moderate fire risk. Toxic by ingestion, inhalation, and skin absorption. Eye and upper respiratory tract irritant, central nervous system impairment.
Health HazardInhalation 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 HazardMesityl 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 HazardBehavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back.
Safety ProfilePoison 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 ExposureMesityl 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
ShippingUN1229 Mesitly oxide, Hazard Class: 3; Labels: 3-Flammable liquid.
Purification MethodsPurify 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.]
IncompatibilitiesMay 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 DisposalDissolve 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.
4-Methyl-3-penten-2-one O-methyl oxime Jasmone 1-(P-METHOXYPHENYL)-4-METHYL-1-PENTEN-3-ONE p-Toluquinone THYMOQUINONE 3,4-Dimethyl-3-[(trimethylsilyl)methyl]-4-penten-2-one 4-CARBETHOXY-2-ETHYL-3-METHYL-2-CYCLOHEXEN-1-ONE MESITYL OXIDE (4-METHYL-3 & 4-PENTEN-2-ONE) 2,5-Dimethyl-3,4-diphenylcyclopentadienone 4-CARBETHOXY-3-METHYL-2-CYCLOHEXEN-1-ONE 1-(5,5-Dimethyl-1-cyclohexen-1-yl)-3-methyl-4-penten-1-one 1,1-Difluoro-4-methyl-1-penten-3-one 3,5-Dimethyl-2-cyclohexen-1-one 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-2-methyl-1-penten-3-one 1-(1,3-Dimethyl-2-oxabicyclo[2.2.2]octan-3-yl)-4-methyl-3-penten-2-one 5-(Dimethylamino)-2-methyl-1-penten-3-one 3-Pentyl-1-diazo-4-methyl-3-penten-2-one TRIMESITYLPHOSPHINE

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