Isophorone Chemical Properties
- Melting point:-8 °C (lit.)
- Boiling point:213-214 °C (lit.)
- Density 0.923 g/mL at 25 °C (lit.)
- vapor density 4.77 (vs air)
- vapor pressure 0.2 mm Hg ( 20 °C)
- refractive index n
- FEMA 3553 | ISOPHORONE
- Flash point:184 °F
- storage temp. Store below +30°C.
- solubility 14.5g/l
- form Liquid
- color Clear colorless to yellow
- OdorLike camphor.
- explosive limit0.8-3.8%(V)
- Water Solubility Soluble in water (12g/L).
- JECFA Number1112
- Merck 14,5196
- BRN 1280721
- Henry's Law Constant(x 10-6 atm?m3/mol): 5.8 (calculated, U.S. EPA, 1980a)
- Exposure limitsTLV-TWA 25 mg/m3 (5 ppm); IDLH 800 ppm.
- Stability:Stable. Substances to be avoided include strong bases, strong acids and strong oxidizing agents.
- CAS DataBase Reference78-59-1(CAS DataBase Reference)
- NIST Chemistry Reference2-Cyclohexen-1-one, 3,5,5-trimethyl-(78-59-1)
- EPA Substance Registry SystemIsophorone (78-59-1)
- Hazard Codes Xn
- Risk Statements 21/22-36/37-40
- Safety Statements 13-23-36/37/39-46
- RIDADR UN 3082 9 / PGIII
- WGK Germany 1
- RTECS GW7700000
- Autoignition Temperature864 °F
- TSCA Yes
- HS Code 2914 29 00
- Hazardous Substances Data78-59-1(Hazardous Substances Data)
- ToxicityLD50 in male, female rats and male mice (mg/kg): 2700 ±200, 2100 ±200, 2200 ±200 orally (PB90-180225)
Isophorone Usage And Synthesis
- DescriptionIsophorone (chemical formula: C9H14O) has its full name being 3, 5, 5-Trimethyl-2-cyclohexen-1-one. It is a kind of α, β-unsaturated cyclic ketone, and is a flavoring ingredient existing in cranberries and saffron. Isophorone can be used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticide. It can also act as an intermediate in organic synthesis as well as the ingredient in wood preservatives and floor sealants. It is mainly manufactured through the self-condensation of acetone with KOH.
- Chemical PropertiesIsophorone, an alpha, beta-unsaturated ketone, is also an industrial solvent used in a variety of different applications. Most of the isophorone used in industry is used in vinyl coatings and inks.
Isophorone is an insoluble, colorless to white liquid and has an odor similar to peppermint. Its characteristic odor is detectable at concentrations as low as 1.00 mg/m3 (0.2 ppm) (Ruth, 1986). Although not highly volatile, with a vapor pressure of 0.438mm Hg at 25 °C.
- DescriptionIsophorone has a slightly minty odor.
- Chemical PropertiesIsophorone has a peppermint-like odor.
- Physical propertiesClear, colorless liquid with a sharp peppermint or camphor-like odor. Experimentally determined detection and recognition odor threshold concentrations were 1.1 mg/m3 (190 ppbv) and 3.0 μg/m3 (530 ppbv), respectively (Hellman and Small, 1974).
- OccurrenceReported found in Burley tobacco, cranberry, macadamia nuts, peas, roasted filbert, saffron, wine, osmanthus, grapefruit juice, papaya, kohlrabi, Parmesan cheese, roast beef, black tea, oats, Japanese plum, prunes, plumcot, starfruit, mango, rice, buckwheat, okra and sweet grass oil.
- UsesSolvent for lacquers, resins, and plastics
- UsesIsophorone is used as a solvent for vinylresins and cellulose esters, and in pesticides.
- UsesSolvent in some printing inks, paints, lacquers and adhesives.
- DefinitionChEBI: A cyclic ketone, the structure of which is that of cyclohex-2-en-1-one substituted by methyl groups at positions 3, 5 and 5.
- Aroma threshold valuesDetection: 0.20 ppm; aroma characteristics at 1.0%: cooling, woody, camphoraceous, slightly green and herbal
- Taste threshold valuesTaste characteristics at 30 ppm: sweet, green, waxy, pungent camphoreous, cooling minty
- Synthesis Reference(s)Synthetic Communications, 22, p. 1845, 1992 DOI: 10.1080/00397919208021315
Synthesis, p. 905, 1978 DOI: 10.1055/s-1978-24936
- General DescriptionA clear colorless liquid, with a camphor-like odor. Less dense than water and insoluble in water. Boiling point 420°F. Flash point near 200°F. Contact irritates skin and eyes. Toxic by ingestion. Used as a solvent and in pesticides.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileKetones, such as Isophorone, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. Forms explosive peroxides
- HazardIrritant to skin and eyes. Possible carcinogen.
- Health HazardIsophorone is an irritant, moderately toxic athigh concentrations, mutagenic and possiblycarcinogenic. Inhalation of its vapors cancause mild irritation of the eyes, nose, andthroat. Exposure to 840 ppm for 4 hours resulted in severe eye irritation in guineapigs. Its irritation effect on human eyes maybe felt at 25–40 ppm. At concentrationsabove 200 ppm, it may cause irritation ofthe throat, headache, nausea, dizziness, and afeeling of suffocation (ACGIH 1986). In rats,exposure to 1840 ppm for 4 hours was fatal.Ingestion of isophorone can cause narcosis,dermatitis, headache, and dizziness.
LD50 value, oral (rats): 2330 mg/kg
Isophorone is mutagenic and when fed torats orally, 258 g/kg for 2 years, it causedkidney tumor. Its carcinogenicity on humansis not reported.
- Fire HazardCombustible.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Industrial usesIsophorone is an excellent solvent for cellulose esters, nitrocellulose, natural and synthetic resins. Isophorone has a very high aromatic hydrocarbon dilution ratio in nitrocellulose formulations: 5.7 for toluene and 5.1 for xylene. The excellent solvency of isophorone allows the preparation of 45% solids nitrocellulose solutions at room temperatures.
- Chemical SynthesisIsophorone is an intermediate in the synthesis of 3,5-xylenol, 3,3,5-trimethylcyclohexanol
- CarcinogenicityIn a 2 year bioassay in rats and mice (conducted by gavage on a 5- day/week treatment schedule) at dose levels of 0, 250, and 500 mg/kg/day isophorone, there was decreased survival of male rats and slight nephrotoxicity in female rats. There was no evidence of carcinogenicity in female rats or mice. In male rats, there was an increase in renal tumors in animals given either 250 or 500 mg/kg/day, and a low incidence of preputial gland tumors at 500 mg/kg. Other proliferative lesions in male rats included hyperplasia of the renal pelvis and tubular cell hyperplasia.
- Environmental FateBiological. The pure culture Aspergillus niger biodegraded isophorone to 3,5,5-trimethyl-2-
cyclo-hexene-1,4-dione, 3,5,5-trimethylcyclohexane-1,4-dione, (S)-4-hydroxy-3,5,5-trimethyl-2-
cyclohex-1-one, and 3-hydroxymethyl-5,5-dimethyl-2-cyclohexen-1-one (Mikami et al., 1981).
Chemical/Physical. At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 34 mg/L. The adsorbability of the carbon used was 193 mg/g carbon (Guisti et al., 1974).
Isophorone will not hydrolyze in water.
At influent concentrations of 10, 1.0, 0.1, and 0.001 mg/L, the GAC adsorption capacities were 78.3, 32.0, 13.1, and 5.4 mg/g, respectively (Dobbs and Cohen, 1980).
- Purification MethodsWash isophorone with aqueous 5% Na2CO3 and then distil it under reduced pressure immediately before use. Alternatively, it can be purified via the semicarbazone. [Erskine & Waight J Chem Soc 3425 1960, Beilstein 7 IV 165.]
- Toxicity evaluationThe toxicological mechanisms of isophorone are not well characterized. Critical effects include irritation, narcosis, malaise, fatigue, and CNS depression. Isophorone may induce its neurological effects by interference with neuronal impulse transmissions via physical interaction with nerve membrane components. In animal models, isophorone may also act by inducing neuropathy, involving binding to globulin proteins, although this mechanism may not be relevant to humans. Lesions of the liver have been observed after overexposure in mouse models, although it is not clear whether isophorone elicited the lesions directly or by enhancing an age-related process. DNA-binding studies in mice have shown no significant covalent binding of isophorone or its metabolites to DNA from liver or kidney cells, supporting a potential nongenotoxic mechanism of toxicity.
- Waste DisposalIncineration.
Isophorone Preparation Products And Raw materials
- ISOPHORONE DIISOCYANATE,Isophorone diisocyanate (mixture of isomers),ISOPHORONE DIISOCYANATE, 98%, MIXTURE OF ISOMERS,diisocyanated’isophoron Norandrostenedione 2-Cyclohexen-1-one 2-DEOXY-20-HYDROXYECDYSONE Glycyrrhizic acid 5-(1-HYDROXY-2,6,6-TRIMETHYL-4-OXOCYCLOHEX-2-ENYL)-3-METHYLPENTA-2,4-DIENOIC ACID 18alpha-Glycyrrhetinic acid MURISTERONE A VERBENONE Hydroxyecdysone QUASSIN (+)-Abscisic acid 1-HYDROXY-4-KETO-2-IONONE 2,2,6-trimethylcyclohex-2-en-1,4-dione (4-oxo-isophorone) (-)-VERBENONE POLYPODINE B Ecdysone 4-(Diethylamino)salicylaldehyde
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