ISOPHORONE

Isophorone is an α,β-unsaturated cyclic ketone. 
Isophorone is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. 
Isophorone is used as a solvent and as a precursor to polymers.
Isophorone is produced on a large scale industrially.

CAS Number: 78-59-1
EC Number: 201-126-0
IUPAC Name: 3,5,5-Trimethylcyclohex-2-en-1-one
Chemical Formula: C9H14O

Other names: 78-59-1, Isoacetophorone, 3,5,5-Trimethylcyclohex-2-en-1-one, Isoforone, 3,5,5-Trimethylcyclohex-2-enone, Isooctopherone, Isoforon, Izoforon, 3,5,5-Trimethyl-2-cyclohexen-1-one, 2-Cyclohexen-1-one, 3,5,5-trimethyl-, alpha-Isophorone, 1,1,3-Trimethyl-3-cyclohexene-5-one, Isophoron, 3,5,5-Trimethyl-2-cyclohexenone, .alpha.-Isophoron, NCI-C55618, 3,5,5-Trimethyl-2-cyclohexen-1-on, UNII-2BR99VR6WA, 3,5,5-Trimetil-2-cicloesen-1-one, .alpha.-Isophorone, Isophorone, 97%, NSC 403657, 3,5,5-Trimethyl-2-cyclohexene-1-one, 2BR99VR6WA, CHEBI:34800, NSC4881, 3,5,5-Trimethylcyclohexen-2-one-1, 3,3,5-Trimethyl-2-cyclohexen-1-one, DSSTox_CID_759, DSSTox_RID_75774, DSSTox_GSID_20759, Izoforon, 3,5-Trimethyl-2-cyclohexenone, Isoforone, Caswell No. 506, 3,5-Trimetil-2-cicloesen-1-one, 3,5-Trimethyl-2-cyclohexen-1-one, 1,3-Trimethyl-3-cyclohexene-5-one, 3,5-Trimethyl-2-cyclohexene-1-one, WLN: L6V BUTJ C1 D1 D1, 2-Cyclohexen-1-one,5,5-trimethyl-, CAS-78-59-1, FEMA No. 3553, CCRIS 1353, HSDB 619, ISOPHORONE, REAG, EINECS 201-126-0, 3,5-Trimethyl-2-cyclohexen-1-on, EPA Pesticide Chemical Code 047401, BRN 1280721, 3,5,5-Trimethylcyclohexenone, a-Isophorone, AI3-00046, 3,5,5-Trimethylcyclohexen one, alpha -isophoron, alpha -isophorone, 3,5,5-Trimetil-2-cicloesen-1-one, nchem.180-comp3, 3,5,5-Trimethyl-2-cyclohexen-1-on, 1,5,5-Trimethyl-1-cyclohexen-3-one, Isophorone Reagent Grade, EC 201-126-0, SCHEMBL22522, Isophorone, >=97%, FG, 4-07-00-00165, BIDD:ER0627, Isophorone, analytical standard, CHEMBL1882894, DTXSID8020759, FEMA 3553, 3,5,5-trimethyl-cyclohex-2-enone, HY-Y0932, Isophorone-2,4,4,6,6-, NSC-4881, Tox21_202312, Tox21_300050, BBL027346, MFCD00001584, NSC403657, s2998, STK801792, ZINC14822379, AKOS000120392, 3,5,5-trimethylcyclohex-2-ene-1-one, 3,5,5-trimethylcyclohexa-2-en-1-one, MCULE-5564101474, NSC-403657, 3,3,5-trimethyl-cyclohex-5-en-1-one, 3,5,5-trimethyl-cyclohex-2-en-1-one, 1,1, 3-Trimethyl-3-cyclohexene-5-one, 3,5, 5-Trimethyl-2-cyclohexene-1-one, NCGC00164006-01, NCGC00164006-02, NCGC00164006-03, NCGC00254115-01, NCGC00259861-01, 3,3,5-trimethyl-cyclohex-5 -en-1-one, AC-10580, K387, VS-08530, Isophorone, Vetec(TM) reagent grade, 97%, CS-0015924, FT-0627443, I0151, D72515, A839454, Q415519, W-104274, F0001-2053, 201-126-0, 2BR99VR6WA, 2-Cyclohexen-1-one, 3,5,5-trimethyl-, 3,5,5-Trimethyl-2-cyclohexen-1-on, 3,5,5-Trimethyl-2-cyclohexen-1-on, 3,5,5-Trimethyl-2-cyclohexen-1-one, 3,5,5-Triméthyl-2-cyclohexén-1-one, 3,5,5-Trimethylcyclohex-2-en-1-one, 78-59-1, GW7700000, Isophorone, L6V BUTJ C1 E1 E1, 异佛尔酮, 1,1,3-trimethyl-3-cyclohexene-5-one, 1,5,5-Trimethyl-1-cyclohexen-3-one, 14397-59-2, 2-Cyclohexen-1-one, 3,5, 5-trimethyl-, 3,3,5-Trimethyl-2-cyclohexen-1-one, 3,3,5-trimethyl-2-cyclohexene-1-one, 3,5,5-trimethyl-1-cyclohex-2-enone, 3,5,5-Trimethyl-2-cyclohexen-1-on, 3,5,5-Trimethyl-2-cyclohexene-1-one, 3,5,5-trimethylcyclohex-2-enone, 3,5,5-Trimethylcyclohexen one, 3,5,5-Trimethylcyclohexen-2-one-1, 3,5,5-Trimethylcyclohexenone, 3,5,5-Trimetil-2-cicloesen-1-one, 3,5,5-Trimetil-2-cicloesen-1-one, 4-07-00-00165, a-Isophorone, BB_NC-0161, Cyclohex-2-en-1-one, 3,5,5-trimethyl-, Diisophorone, EINECS 201-126-0, FEMA 3553, Isoacetophorone, Isoforon, Isoforone, Isoforone, Isooctopherone, Isophoron, ISOPHORONE (3-METHYL-D3, 2,4,4,6,6-D5), Isophorone;3,5,5-Trimethyl-2-cyclohexene-1-one, ISOPHORONE-2,4,4,6,6-D5, Izoforon, Izoforon, l04130, NCGC00164006-01, ST5330654, UNII:2BR99VR6WA, UNII-2BR99VR6WA, VS-08530, WLN: L6V BUTJ C1 D1 D1, α -isophoron, α -isophorone, α-Isophoron, α-isophorone, α-Isophorone

Isophorone is a clear liquid that smells like peppermint. 
Isophorone can be dissolved in water.
Isophorone is used in industries to help dissolve other chemicals such as printing inks, paints, lacquers, and adhesives. 

Isophorone can also be used as an intermediate to make other chemicals.
Although isophorone is an industrial chemical, Isophorone also occurs naturally in cranberries.
Acts as a stable, colorless, high-boiling, low vapor pressure solvent. 

Isophorone is used as solvent for vinyl chloride-acetate based coatings, solvent for nitrocellulose lacquers, solvent for printing inks, and solvent for lacquer thinners. 
Exhibits slight solubility in water but good miscibility with most lacquer solvents. 
Possesses high solvency power, and high dilution ratio for aromatic hydrocarbons.

Physical Description of Isophorone:
Isophorone appears as a 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. 
Isophorone is used as a solvent and in pesticides.

Uses of Isophorone:
Isophorone is used mainly as a solvent for concentrated vinyl chloride/acetate-based coating systems for metal cans, other metal paints, nitrocellulose finishes, and printing inks for plastics.
Isophorone is also used in some herbicide and pesticide formulations and in adhesives for plastics, polyvinylchloride, and polystyrene materials.
Isophorone is an intermediate in the synthesis of 3,5-xylenol, 3,3,5-trimethylcyclohexanol, and plant growth retardants.

Isophorone is used mainly as a solvent for concentrated vinyl chloride/acetate-based coating systems for metal cans, other metal paints, nitrocellulose finishes, and printing inks for plastics. 
Isophorone is an intermediate in the synthesis of 3,5-xylenol, 3,3,5-trimethylcyclohexanol, and plant growth retardants.

Isophorone is used as a solvent for coatings, especially vinyl resins applied by roller. 
Also used as a chemical intermediate and a solvent for other materials.

Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses.

Solvent for lacquers & plastics.
Solvent for many oils, fats, gums, resins, nitrocellulose, & vinyl-resin copolymers.
Chem int for 3,3,5-trimethylcyclohexanol, & 3,5-xylenol; specialty solvent.

Industry Uses of Isophorone:
Intermediates
Solvents (which become part of product formulation or mixture)
Waste

Consumer Uses of Isophorone:
Paints and coatings

Use Classification of Isophorone:
Hazardous Air Pollutants (HAPs)

Food additives - Flavoring Agents

Flavoring Agents - JECFA Flavorings Index

Flavouring Agent - FLAVOURING_AGENT; - JECFA Functional Classes

Fire Hazards - Carcinogens, Flammable - 2nd degree, Reactive - 1st degree

Applications of Isophorone:
The partly hydrogenated derivative trimethylcyclohexanone is used in production of polycarbonates. 
Isophorone condenses with phenol to give an analogue of bisphenol A. 

Polycarbonates produced by phosgenation of these two diols produces a polymer with improved thermal stability.
Trimethyladipic acid and 2,2,4-trimethylhexamethylenediamine are produced from trimethylcyclohexanone and trimethylcyclohexanol. 

They are used to make specialty polyamides. 
Hydrocyanation gives the nitrile followed by reductive amination gives isophorone diamine. 
This diamine is used to produce isophorone diisocyanate which has certain niche applications.

Full hydrogenation gives 3,3,5-Trimethylcyclohexanol, a precursor to both sunscreens and chemical weapons.

Structure and reactivity of Isophorone:
Isophorone undergoes reactions characteristic of an α,β-unsaturated ketone. 
Hydrogenation gives the cyclohexanone derivative. 
Epoxidation with basic hydrogen peroxide affords the oxide.

Isophorone is degraded by attack of hydroxyl radicals.

Photodimerization of Isophorone:
When exposed to sunlight in aqueous solutions, isophorone undergoes 2+2 photocycloaddition to give three isomeric photodimers. 
These "diketomers" are cis-syn-cis, head to tail (HT), cys-anti-cys (HT), and head-head (HH). 
The formation of HH photodimers is favored over HT photodimers with increasing polarity of the medium.

Natural Occurrence of Isophorone:
Isophorone occurs naturally in cranberries.

Synthesis of Isophorone:
Isophorone is produced on a multi-thousand ton scale by the aldol condensation of acetone using KOH. 
Diacetone alcohol, mesityl oxide, and 3-hydroxy-3,5,5-trimethylcyclohexan-1-one are intermediates. 
A side product is beta-isophorone, where the C=C group is not conjugated with the ketone.

Human Metabolite Information of Isophorone:

Cellular Locations of Isophorone:
Cytoplasm
Extracellular

Methods of Manufacturing of Isophorone:
Acetone is passed over calcium oxide, hydroxide or carbide or their mixt at 350 °c and atmospheric pressure, or Isophorone is heated  200-250 °c under pressure. 
Isophorone is separated from resultant products by distillation.

Produced by the condensation of acetone in the liquid phase at ca. 200 °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 by products can be carried out in a single reactor. 
Reaction in the gas phase at 350 °C over calcium-aluminum oxide has also been reported.

General Manufacturing Information of Isophorone:

Industry Processing Sectors of Isophorone:
Paint and coating manufacturing
Pesticide, fertilizer, and other agricultural chemical manufacturing
Printing ink manufacturing

Analytic Laboratory Methods of Isophorone:
NIOSH Method 2508. Isophorone. 
Technique: Gas chromatography, FID. 

The working range for this method is 0.35 to 70 ppm (2 to 400 mg/cu m) for a 12-L air sample. 
Estimated limit of detection: 0.02 mg per sample.

Isophorone has been determined in water by gas chromatography and mass spectrometry.

EPA Method 609-A. Nitroaromatics and Isophorone in Wastewater by Gas Chromatography with Electron Capture Detection. 
Detection limit = 16.000 ug/l.

EPA Method 609-B. Nitroaromatics and Isophorone in Wastewater by Gas Chromatography with Flame Ionization Detection. 
Detection limit = 5.7 ug/l.

Sources and Potential Exposure of Isophorone:
Major sources of airborne isophorone are the printing and the metal coating industries.  
Coal-fired power plants may also emit isophorone to the air.

Individuals may be exposed to isophorone through breathing contaminated air, especially people who work with inks, paints, lacquers, and adhesives.
Isophorone has been detected in the drinking water of several cities at very low concentrations.

Assessing Personal Exposure of Isophorone:
No medical tests are currently available to determine human exposure to isophorone.

Physical Properties of Isophorone:
Isophorone is a water-white colored liquid with a peppermint-like odor.
The chemical formula for isophorone is C9H14O and the molecular weight is 138.21 g/mol.

The vapor pressure for isophorone is 0.3 mm Hg at 20 °C and Isophorone has an octanol/water partition coefficient (log Kow) of 1.67.
Isophorone has an odor threshold of 0.20 parts per million (ppm).
Isophorone is slightly soluble in water.

History of Isophorone:
The use of isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which is a waste product of phenol synthesis by the Hock method.

Production of the solvent isophorone started in 1962 in the Herne nitrogen works of Hibernia AG. 
The development of the new solvent resulted from the search for ways in which to dispose of or recycle acetone. 
In 1967 Isophorone production was carried out in what is today the Herne plant of Evonik Industries AG and was previously the Hibernia factory Herne I.

Putting the first production plant into operation in 1967 signaled the start of acetone chemistry in Herne that was intended to position the site for the future and that still provides Isophorone with security today. 
When VEBA AG reorganized Isophorone chemical business, the Herne plants were transferred to Hüls AG in 1979 and so was the Isophorone product family. 
Since 1992 product variants of Isophorone and since 1999 Isophorone are today also manufactured at the Evonik site in Mobile, Alabama.

Isophorone has excellent solvent properties for binders, resins, and numerous chemical products. 
Isophorone is used as high boiling solvent in paints, printing inks and adhesives. 

In these applications Isophorone improves flowing properties and brightness. 
Because of Isophorone special chemical structure, Isophorone serves as starting material for production of several chemicals, which otherwise are hardly producible. 

These Isophorone derivatives are used in many different areas. 
In the construction industry, for example, they are used as corrosion protection on bridges, scaffolding or sluices. 
They are used in wood preservatives and to seal floors.