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Isophorone(CAS No. 78-59-1)

Isophorone C9H14O (cas 78-59-1) Molecular Structure

78-59-1 Structure

Identification and Related Records

【Name】
Isophorone
【Iupac name】
3,5,5-trimethylcyclohex-2-en-1-one
【CAS Registry number】
78-59-1
【Synonyms】
1,1,3-Trimethyl-3-cyclohexene-5-one
1,5,5-Trimethyl-3-oxocyclohexene
1-Cyclohexen-3-one, 1,5,5-trimethyl-
3,5,5-Trimethyl-2-cyclohexen-1-one
3,5,5-Trimethyl-2-cyclohexene-1-one
3,5,5-Trimethyl-2-cyclohexenone
Isoacetophorone
Isoforon
Isophoron
NSC 403657
NSC 4881
a-Isophoron
a-Isophorone
iso-phorone
2-Cyclohexen-1-one,3,5,5-trimethyl-
【EINECS(EC#)】
201-126-0
【Molecular Formula】
C9H14O (Products with the same molecular formula)
【Molecular Weight】
138.2069
【Inchi】
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
【InChIKey】
HJOVHMDZYOCNQW-UHFFFAOYSA-N
【Canonical SMILES】
CC1=CC(=O)CC(C1)(C)C
【MOL File】
78-59-1.mol

Chemical and Physical Properties

【Appearance】
light yellow liquid
【Density】
0.923
【Melting Point】
-8℃
【Boiling Point】
215℃
【Vapour】
0.2 mm Hg ( 20 °C)
【Refractive Index】
1.476
【Flash Point】
84℃
【Solubilities】
Soluble in ether, acetone, alcohol
Has high solvent power for vinyl resins, cellulose esters, ether, and many substances soluble with difficulty in other solvents.
In water, 12,000 mg/l @ 25 deg C.
【Color/Form】
Water-white liquid
Colorless to white-liquid.
Clear liquid
【Stability】
Stable. Substances to be avoided include strong bases, strong acids and strong oxidizing agents.
【Storage temp】
2-8°C
【Spectral properties】
UV max (MeOH): 235.5 nm (e 14300)
Index of refraction: 1.4766 @ 18 deg C/D
MAXIMUM ABSORPTION (ALCOHOL): 236 NM (LOG E= 4.09); SADTLER REF NUMBER: 122 (IR, PRISM)
Intense mass spectral peaks: 82 m/z (100%), 138 m/z (17%), 54 m/z (13%), 41 m/z (13%)
IR: 36 (Sadtler Research Laboratories IR Grating Collection)
UV: 6-247 (Phillip et al., Organic Electronic Spectral Data, John Wiley & Sons, New York)
NMR: 7311 (Sadtler Research Laboratories Spectral Collection)
MASS: 57756 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
【Computed Properties】
Molecular Weight:138.20686 [g/mol]
Molecular Formula:C9H14O
XLogP3-AA:1.6
H-Bond Donor:0
H-Bond Acceptor:1
Rotatable Bond Count:0
Tautomer Count:8
Exact Mass:138.104465
MonoIsotopic Mass:138.104465
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Formal Charge:0
Complexity:187
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:1
Effective Rotor Count:0.6
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R21/22;R36/37;R40
【Safety Statements 】
S13;S23;S36/37/39;S46
【Safety】
Hazard Codes:Xn
Risk Statements:21/22-36/37-40
21/22:Harmful by inhalation, in contact with skin and if swallowed
36/37:Irritating to eyes and respiratory system
40:Limited evidence of a carcinogenic effect
Safety Statements:13-23-36/37/39-46
13:Keep away from food, drink and animal feeding stuffs
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
46:If swallowed, seek medical advice immediately and show this container or label
WGK Germany:1
Hazardous Substances Data:78-59-1(Hazardous Substances Data)
【Skin, Eye, and Respiratory Irritations】
... HUMAN VOLUNTEERS EXPOSED AT 40, 85, 200 & 400 PPM ISOPHORONE EXPERIENCED EYE, NOSE, & THROAT IRRITATION.
Irritates and burns eyes, nose, mucous membranes, respiratory tract.
Isophorone vapor (25 ppm) produced irritation to the eyes, nose, and throats of unacclimatized volunteers.
【Cleanup Methods】
If leak or spill has not ignited, use water spray to disperse vapors & to protect men attempting to stop leak.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surfact flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or comercial sorbents.
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.
Environmental considerations: Air spill: Apply water spray or mist ot knock kown vapors.
【Transport】
无资料?
【Fire Fighting Procedures】
Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.
Use water spray to keep fire exposed containers cool. Use flooding quantities of water as fog or spray, dry chemical, foam, or carbon dioxide.
【Fire Potential】
Flammable & explosive when exposed to heat or flame.
【Formulations/Preparations】
Purity: 98.0% by wt., min.
【Exposure Standards and Regulations】
Isophorone is listed as an indirect food additive for use only as a component of adhesives.
【Reactivities and Incompatibilities】
Incompatible with strong oxidizers
Oxidizers, strong alkalis, amines.
【Other Preventative Measures】
Irrigate eyes with water. Wash skin with abundant quantities of water.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
【Protective Equipment and Clothing】
... Wear appropriate chemical protective gloves, boots and goggles.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection
Recommendations for respirator selection. Max concn for use: 40 ppm. Respirator Class(es): Any chemical cartridge respirator with organic vapor cartridge(s). May require eye protection. Any supplied-air respirator. May require eye protection.
Recommendations for respirator selection. Max concn for use: 100 ppm. Respirator Class(es): Any supplied-air respirator operated in a continuous flow mode. May require eye protection. Any powered, air-purifying respirator with organic vapor cartridge(s). May require eye protection.
Recommendations for respirator selection. Max concn for use: 200 ppm. Respirator Class(es): Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s). Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister. Any powered, air-purifying respirator with a tight-fitting facepiece and organic vapor cartridge(s). May require eye protection. Any supplied-air respirator that has a tight-fitting facepiece and is operated in a continuous-flow mode. May require eye protection. Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece.
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: Respirator Class(es): Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode. Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive-pressure mode.
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Class(es): Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister. Any appropriate escape-type, self-contained breathing apparatus.
【Specification】

light yellow liquid
Safety Statements:13-23-36/37/39-46
13:Keep away from food, drink and animal feeding stuffs
23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
46:If swallowed, seek medical advice immediately and show this container or label
【Octanol/Water Partition Coefficient】
log Kow = 1.70
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
The following wastewater treatment technologies have been investigated for Isophorone. Concentration process: Biological treatment.
The following wastewater treatment technologies have been investigated for Isophorone. Concentration process: Solvent extraction.
The following wastewater treatment technologies have been investigated for Isophorone. Concentration process: Activated carbon.
Spray into incinerator or burn in paper packaging. Additional flammable solvent may be added.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

ACETONE ... IS PASSED OVER CALCIUM OXIDE, HYDROXIDE OR CARBIDE OR THEIR MIXT AT 350 DEG C AND ATMOSPHERIC PRESSURE, OR IT IS HEATED @ 200-250 DEG C UNDER PRESSURE. ISOPHORONE IS SEPARATED FROM RESULTANT PRODUCTS BY DISTILLATION.
Produced by the condensation of acetone in the liquid phase at ca. 200 deg C and 3.6 Mpa in the presence of an aqueous potassium hydroxide solution (ca. 1%). The process steps condensation, separation of unreacted acetone, and hydrolysis of byproducts can be carried out in a single reactor. Reaction in the gas phase at 350 deg C over calcium-aluminum oxide has also been reported.
Review of preparation and purification: G.S. Salvapati, M. Janardanarao, J. Sci. Ind. Res. 42, 261-267 (1983).
U.S. Imports

(1984) 9.81X10+8 g
(1986) 7.44X10+5 lb
U.S. Production

(1972) GREATER THAN 4.54X10+5 G
(1976) GREATER THAN 2.27X10+6 G
Worldwide production capacity for isophorone currently stands at ca. 50,000 tons annually.
【Sampling Procedures】
Activated charcoal, Ambersorb XE-348, and Amberlites XAD-2, XAD-4, and XAD-7 were evaluated as solid adsorbents for work-room air sampling of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl n-butyl ketone, cyclohexanone, and isophorone. Activated charcoal had good capacity for the compounds investigated, but most ketones decomposed on this adsorbent during storage. Ambersorb XE-348 also showed good capacity for most of the ketones and decomposition was insignificant. [Levin JO, Carleborg L; Ann Occup Hyg 31 (1): 31-8 (1987)] PubMed Abstract
NIOSH Method 2508. Analyte: isophorone; sampler: solid sorbent tube (petroleum-based charcoal, 100 mg/50 mg); flow rate: 0.01-1 l/min; vol: -min: 2 l, -max: 25 l; sample stability: at least 7 days @ 25 deg C.

Biomedical Effects and Toxicity

【Pharmacological Action】
LIQUID: Irritating to skin and eyes. Harmful if swallowed.
【Biomedical Effects and Toxicity】
The demonstrated toxicity of isophorone by oral, inhalation, and dermal exposures indicates that it is capable of passage across epithelial membranes.
Rabbits and rats treated orally with isophorone excreted unchanged isophorone in the expired air and in the urine.
Preliminary results of a pharmacokinetic study indicate that rats treated orally with 14C-isophorone excreted 93% of the radiolabel in the urine, expired air & feces in 24 hr. The majority was found in the urine indicating that isophorone was well absorbed. The wide distribution of isophorone in the organs of rats & a rabbit 1-5 hr after dosing by gavage with 4000 mg/kg indicates rapid GI absorption. In two rabbits given a gavage dose of 1000 mg/kg isophorone, a blood level of isophorone of 102 ug/L was found within 10 min. The level increased to 141 ug/L in 30 min & declined to
In rats exposed to 400 ppm isophorone for 4 hr & sacrificed immediately after exposure or 1.5 or 3 hr after exposure, levels of isophorone were highest in all tissues examined (brain, lungs, heart, stomach, liver, spleen, pancreas, kidney, adrenals, testicles, & ovaries) immediately after exposure. Levels ranged from 1.5-74 ug/g tissue wet weight. The levels declined rapidly in males but declined very little in females by 3 hr after exposure.
Radiolabel was widely distributed in male rats 24 hr after an oral dose of 14C-isophorone in corn oil, with highest levels in the liver, kidney, preputial gland, testes, brain, & lungs. Isophorone was widely distributed to the tissues of rats & a rabbit following treatment with isophorone at a gavage dose of 4000 mg/kg. The rats died within 1-5 hr & the rabbit died within an hr after dosing at which times the tissues were sampled for analysis. in rats, tissue levels of isophorone in ug/g tissue wet weight were as follows: stomach-6213, pancreas-2388, adrenals-1513, spleen-1038, liver-613, brain-378, lung-383, heart-387, kidney-465, testes-275, & ovaries-471. In the rabbit, tissue levels were as follows: stomach-5395, adrenals-1145, ovaries-3000, spleen-545, liver-515, kidney-295, heart-260, & lungs-50.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of isophorone with photochemically-produced hydroxyl radicals has been estimated as 8.1X10-11 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Isophorone is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2-4) nor to undergo direct photolysis due to the lack of absorption in the environmental UV spectrum (>290 nm)(5). The rate constant for the vapor-phase reaction of isophorone with ozone has been estimated as 7.4X10-17 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(6).

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