Description
2-Ethylhexanol, also known as 2-Ethylhexan-1-ol, abbreviated as 2-EH, is a branched eight-carbon alcohol. In industry, 2-EH is mainly used to make ester plasticizers, which can be used to produce soft polyvinyl chloride. 2-EH can also be used to make a chemical used in the production of coating materials, adhesives, printing inks and impregnation agents. 2-EH occurs naturally in food and is used as a volatile flavoring agent and is indirectly approved as a food additive by the FDA. In addition, 2-EH is also used as an inert pesticide ingredient in pesticide formulations for cultivated crops, raw agricultural products (RAG) or animals.
Chemical Properties
2-Ethylhexanol is a clear, colorless to pale yellow oily liquid. It has a mild, oily, sweet, slightly floral odor reminiscent of rose and sweet, fatty-floral taste with a fruity note. Soluble in 720 times water, miscible in most organic solvents.
Occurrence
Reported found in papaya, peach, pear, blackberry, strawberry, cabbage, Parmesan and mozzarella cheese,
butter, roasted chicken, cognac, sherry, grape wines, tea, avocado, kiwifruit, crab and clam.
Uses
2-Ethylhexanol is the most important C8 alcohol and is mainly used as the alcohol component for the manufacture of ester plasticizers for soft poly(vinyl chloride) (PVC). Other minor uses include the manufacturing of 2-ethylhexyl acrylate, as a dispersing agent and wetting agent, as a solvent for gums and resins, as a cosolvent for nitrocellulose, and in ceramics, paper coatings, rubber latex, textiles, and fragrances.
Uses
2-Ethyl-1-hexanol is used as a flavor, fragrance and plasticizer. It is used to prepare diesters bis(2-ethylhexyl) phthalate. It reacts with nitric acid and used as an octane booster. Its ester, 2-ethylhexyl ester is a component of sunscreen octocrylene. Further, it is used as a low volatility solvent for resins, animal fats, waxes, vegetable oils and petroleum derivatives. In addition to this, it is used in plasticizer, dioctyl phthalate, which is used in the production of polyvinyl chloride products.
Preparation
2-ethylhexanol synthesis: Condensation of acetaldehyde into butanol aldehyde, dehydration to obtain crotonaldehyde, hydrogenation to n-butyraldehyde, condensation dehydration to obtain 2-ethyl-2-hexenal, and then hydrogenation to obtain 2-ethylhexanol.
Application
2-Ethyl-1-hexanol is suitable for use in a study to compare its susceptibilities of dynamic heat capacity and dielectric polarization under isothermal conditions. It may be used to study lipase-catalyzed transesterification (alcoholysis) of rapeseed oil and 2-ethyl-1-hexanol in the absence of solvent. 2-Ethyl-1-hexanol may be used in broadband dielectric spectroscopy studies of the polyalcohols-glycerol, xylitol and sorbitol. It may be used in the preparation of porous beads.
Definition
ChEBI: 2-Ethylhexanol is a primary alcohol that is hexan-1-ol substituted by an ethyl group at position 2. It has a role as a volatile oil component and a plant metabolite.
General Description
2-ethyl hexanol appears as a dark brown liquid with an aromatic odor. Insoluble in water and less dense than water. Flash point between 140 - 175°F. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2-Ethylhexanol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. 2-Ethylhexanol is incompatible with strong oxidizing agents and strong acids.
Health Hazard
Anesthesia, nausea, headache, dizziness; mildly irritating to skin and eyes.
Fire Hazard
2-Ethylhexanol is combustible.
Safety Profile
Moderately toxic by
ingestion, skin contact, intraperitoneal,
subcutaneous, and parented routes. An
experimental teratogen. Other experimental
reproductive effects. A severe eye and
moderate skin irritant. Mutation data
reported. A dangerous fire hazard when ex posed to heat or flame; can react vigorously
with oxidzing materials. To fight fire, use
foam, CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
fumes. See also ALCOHOLS.
Synthesis
By hydrogenation of aldehydes obtained by the oxo process; also synthesized from propylene; by catalytic reduction of
2-ethyl-2-hexenal and other similar patented processes.
Carcinogenicity
Male and female F344 rats
were dosed by oral gavage with 0, 50, 150, or 500 mg/kg
2-ethylhexanol (0.005% in aqueous Cremophor EL, a polyoxyl
35 castor oil), 5 days/week for 2 years. There were no
differences of biological importance between the vehicle
control and a water control group that was included in the
study. There was no evidence of treatment-related neoplastic
lesions in any of the exposed groups.
Toxicity evaluation
2-Ethylhexanol (2-EH) has low oral and dermal acute toxicity, but is moderately irritating to the skin and severely irritating to the eyes. In subchronic repeated-dose studies, liver effects were found, including liver enlargement and peroxisome proliferation in rats and mice. 2-EH is not carcinogenic to mice and rats. No evidence of neurotoxicity was found. Available data indicate that 2-EH is not mutagenic; it is not developmentally toxic. And overall exposure to 2-EH as an inert ingredient in pesticide products is not expected to be harmful to any population.
Toxics Screening Level
The Initial Threshold Screening Level (ITSL) for 2-ethylhexanol is 130 μg/m3 with a 24-hour averaging time.
