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2-Ethylhexanol is mostly used in DOP (plasticizer).
2-Ethylhexanol (abbreviated 2-EH) is a branched, eight-carbon chiral alcohol.
2-Ethylhexanol is a colorless liquid that is poorly soluble in water but soluble in most organic solvents.
CAS Number: 104-76-7
EC Number: 203-234-3
IUPAC Name: 2-Ethylhexan-1-ol
Chemical Formula: C8H18O
Other names: 2-Ethylhexan-1-ol, 2-Ethylhexanol, 2-ETHYL-1-HEXANOL, 104-76-7, 2-Ethylhexyl alcohol, 1-Hexanol, 2-ethyl-, Ethylhexanol, 2-ETHYL HEXANOL, Alcohol, 2-ethylhexyl, 2-Aethylhexanol, FEMA No. 3151, 2-Aethylhexanol [German], CCRIS 2292, HSDB 1118, XZV7TAA77P, NSC 9300, EINECS 203-234-3, 2-ethyl1-hexanol, BRN 1719280, DTXSID5020605, CHEBI:16011, AI3-00940, NSC-9300, DTXCID10605, 2-ETHYL HEXANOL [FCC], EC 203-234-3, 2-ETHYL-1-HEXANOL [MI], 2-ETHYL-1-HEXANOL [FHFI], 2-ETHYL-1-HEXANOL [HSDB], 4-01-00-01783 (Beilstein Handbook Reference), 2-ETHYLHEXAN-1-OL [USP-RS], 2-ETHYLHEXAN-1-OL (USP-RS), (+-)-2-Ethyl-1-hexanol, 2Aethylhexanol, 2Ethyl1hexanol, 1Hexanol, 2ethyl, 2ethylhexyl alcohol, Alcohol, 2ethylhexyl, 2-ETHYLHEXANOL [INCI], (.+-.)-2-ETHYL-1-HEXANOL, USEPA/OPP Pesticide Code: 079098, 203-234-3, (+-)-2-ethyl-1-hexanol-, (+-)-2-ethylhexanol, inchi=1/c8h18o/c1-3-5-6-8(4-2)7-9/h8-9h,3-7h2,1-2h, xi-2-Ethyl-1-hexanol, (+/-)-2-ethylhexanol, (+/-)-2-ETHYL-1-HEXANOL-, 2-Ethyl-hexan-1-ol, Ethylhexanol, 2-, CAS-104-76-7, UNII-XZV7TAA77P, MFCD00004746, 2-ethyhexanol, 2-ethyl-hexanol, 2-ethylhexylalcohol, 2-ethyl 1-hexanol, 2-ethyl hexyl alcohol, SCHEMBL16324, MLS002415694, CHEMBL31637, Alcohols,c7-9-iso-,c8-rich, 2-Ethyl-1-hexanol, >=99%, FEMA 3151, NSC9300, HMS2268N10, WLN: Q1Y4 & 2, 2-Ethyl-1-hexanol, >=99.6%, Tox21_202071, Tox21_300019, LMFA05000703, MSK001028, STL453673, 2-Ethyl-1-hexanol, >=99%, FG, AKOS000120105, AKOS016843836, 2-Ethyl-1-hexanol, analytical standard, NCGC00091294-01, NCGC00091294-02, NCGC00091294-03, NCGC00254215-01, NCGC00259620-01, FE177893, LS-13540, SMR000112222, SY355604, 1ST001028, MSK001028-1000, CS-0016002, E0122, NS00001645, EN300-19353, C02498, D72516, 2-Ethyl-1-hexanol, puriss., >=99.0% (GC), 1ST001028-1000, 2-Ethyl-1-hexanol, SAJ first grade, >=99.0%, 2-Ethylhexanol Solution in Methanol, 1000?g/mL, 2-Ethylhexanol Solution in Methanol, 1000mug/mL, Q209388, 2-Ethylhexan-1-ol, United States Pharmacopeia (USP) Reference Standard
2-Ethylhexanol is produced on a massive scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers.
2-Ethylhexanol is encountered in plants, fruits, and wines.
The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.
The branching in 2-Ethylhexanol inhibits crystallization.
Esters of 2-ethylhexanol are similarly affected, which together with low volatility, is the basis of applications in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points.
Because 2-ethylhexanol is a fatty alcohol, its esters have emollient properties.
Representative is the diester bis(2-ethylhexyl) phthalate (DEHP), commonly used in PVC.
The triester tris (2-Ethylhexyl) trimellitate (TOTM) is another common plasticizer produced via the esterification of three 2-ethylhexanol per trimellitic acid.
2-Ethylhexanol is also commonly used as a low volatility solvent.
2-Ethylhexanol can also be used as a cetane number booster when reacted with nitric acid.
2-Ethylhexanol also used to react with epichlorohydrin and sodium hydroxide to produce the glycidyl ether of the molecule which is used as an epoxy reactive diluent in various coatings, adhesives and sealants applications.
2-Ethylhexanol can be used in the development of photos, production of rubber and extraction of oil and gas.
2-Ethylhexanol is produced industrially by the aldol condensation of n-butyraldehyde, followed by hydrogenation of the resulting hydroxyaldehyde.
About 2,500,000 tons are prepared in this way annually.
The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility.
Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol.
Alcohols prepared in this way are sometimes referred to as oxo alcohols.
The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.
2-Ethylhexanol 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.
2-Ethylhexanol is a primary alcohol that is hexan-1-ol substituted by an ethyl group.
2-Ethylhexanol has a role as a volatile oil component and a plant metabolite.
2-Ethylhexanol is an 8-carbon higher alcohol species.
2-Ethylhexanol is used to make the vinyl chloride plasticizer, bis(2-ethyl hexyl) phthalate.
2-Ethylhexanol is also used to make 2-ethyl hexyl acrylate for adhesives and paints.
2-Ethylhexanol is used for in numerous application such as fragrances, flavours and solvents.
Most commonly 2-Ethylhexanol is used in the production of other chemicals.
2-Ethylhexanol is suitable for use in a study to compare its susceptibilities of dynamic heat capacity and dielectric polarization under isothermal conditions.
2-Ethylhexanol may be used to study lipase-catalyzed transesterification (alcoholysis) of rapeseed oil and 2-ethyl-1-hexanol in the absence of solvent.
2-Ethylhexanol may be used in broadband dielectric spectroscopy studies of the polyalcohols- glycerol, xylitol and sorbitol.
2-Ethylhexanol may be used in the preparation of porous beads.
Main use of 2-Ethylhexanol is that of an intermediate under strictly controlled conditions.
Apart from this it is used in various products and processes as functional fluid, process chemical, cleaning agent and other purposes.
2-Ethylhexanol is an eight-carbon branched chain oxo alcohol having a high boiling point and slow evaporation rate.
2-Ethylhexanol is a versatile solvent featuring excellent reactivity as a chemical intermediate.
2-Ethylhexanol serves as a chain terminator in synthesizing condensation polymers and as an intermediate for plasticizers.
2-Ethylhexanol has low volatility and enhances the flow and gloss of baking enamels.
2-Ethylhexanol is also used as dispersing agent for pigment pastes.
2-Ethylhexanol is most commonly used in production of phthalates for rubber and plastic fabrication.
2-Ethylhexanol is also used as a low volatility solvent and an active component of textile finishing formulations.
2-Ethylhexanol (abbreviated 2-EH) is a fatty alcohol, an organic compound is a branched, eight-carbon chiral alcohol.
2-Ethylhexanol is a colorless liquid that is poorly soluble in water but soluble in most organic solvents.
2-Ethylhexanol is produced on a massive scale for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers.
2-Ethylhexanol is encountered in natural plant fragrances, and the odor has been reported as “heavy, earthy, and slightly floral” for the R enantiomer and “a light, sweet floral fragrance” for the S enantiomer.
2-Ethylhexanol is miscible with most organic solvents but has very limited miscibility with water.
2-Ethylhexanol has one primary hydroxyl group.
2-Ethylhexanol is a colorless liquid. 2-Ethylhexanol is widely used in the production of dioctyl phthalate (vinyl applications), acrylates, 2-ethylhexyl nitrate, lubrication oil additives, mining chemicals, special plasticizers, herbicides and ester oils (non-vinyl application areas).
2-Ethylhexanol is a colorless liquid that is poorly soluble in water but soluble in most organic solvents.
2-Ethylhexanol is used numerous applications such as solvents, flavors, and fragrances and especially as a precursor for the production of other chemicals such as emollients and plasticizers.
2-Ethylhexanol is used in the manufacture of phthalate & sebacate plasticizer and as a solvent in paint, textile, paper coating, leather finishing, etc.
2-Ethylhexanol is the most important C8 alcohol and is used mainly in manufacturing plasticizers.
Other minor uses include the manufacturing of 2-Ethylhexanol, 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.
2-Ethylhexanol is used as a flavor, fragrance and plasticizer.
2-Ethylhexanol is used to prepare diesters bis(2-ethylhexyl) phthalate.
2-Ethylhexanol reacts with nitric acid and used as an octane booster.
2-Ethylhexanols ester, 2-ethylhexyl ester is a component of sunscreen octocrylene.
Further, 2-Ethylhexanol is used as a low volatility solvent for resins, animal fats, waxes, vegetable oils and petroleum derivatives.
In addition to this, 2-Ethylhexanol is used in plasticizer, dioctyl phthalate, which is used in the production of polyvinyl chloride products.
2‐Ethyl hexanol is absorbed by the gastrointestinal tract and skin.
Alcohol dehydrogenase (ADH) rapidly oxidizes the hydroxyl group in 2-Ethylhexanol, forming 2‐ethyl hexanol.
2-Ethylhexanol is further oxidized by aldehyde dehydrogenase (ALDH), forming 2‐ethyl hexanol acid , which is excreted mainly as a glucuronate conjugate in urine.
ADH activity for 2-Ethylhexanol was reported to be 8.6 nmol/ mg/min and 4.2 nmol/mg/min in humans and mice, respectively.
Furthermore, ALDH activity for 2-Ethylhexanol was 3.6 nmol/mg/min and 5.6 nmol/mg/min in humans and mice, respectively.
Within 24 hours of orally administrating 2-Ethylhexanol at 8.3 mmol/ kg, 86.9% of the compound was excreted in urine as the glucuronide conjugate metabolite.
Following oral administration at doses of up to 300 mg/ kg, 2-Ethylhexanol was efficiently absorbed in male CD rats.
Within 28 hours, 2-Ethylhexanol metabolite was excreted in exhaled breath (as CO2; 6%‐7%), feces (8%‐9%), and urine (80%‐82%).
The major urinary metabolite of 2-Ethylhexanol was 2-Ethylhexanol, generated by decarboxylation of partially β‐oxidized 2-Ethylhexanol.
The other identified metabolites were 2‐ethyl‐5‐hydroxyhexanoic acid, 2‐ ethyl‐5‐ketohexanoic acid, and 2‐ethyl‐1,6‐hexanedioic acid.
A study showed that 2-Ethylhexanol is generated from hydrolysis of 2-Ethylhexanol in an environment simulating a concrete slab with a relative humidity (RH) between 70% and 100% and pH between 11 and 13.
In the study, DEHP hydrolysis and 2-Ethylhexanol emission increased with an increase in pH.
Since 2-Ethylhexanol has a half‐life of 100 years at pH 8 and 30°C, it is hardly degraded under normal indoor environment.
Additionally, 2-Ethylhexanol on the surface of cement with higher moisture content emits higher amount of 2-Ethylhexanol.
Thus, there is very little doubt that the amount of 2-Ethylhexanol emission by DEHP is related to the moisture content of the cement with which it has direct contact.
Therefore, dampness seems to play a major role in determining the amount of 2-Ethylhexanol emitted.
A study examined the relationship between RH and 2-Ethylhexanol indoor air concentration, and showed that in buildings with RH values of 58%‐75% and 21%‐22%, the 2-ethylo hexanol indoor air concentrations are 9 μg/m3 and 3 μg/m3 , respectively.
Additionally, in a room with high amount of 2-Ethylhexanol emission, the moisture content of its concrete floor was as high as 8.2%.
However, symptoms of the nose, throat, and lower respiratory tract were observed only in rooms with high 2-Ethylhexanol concentrations.
Faculty members who used a conference room with 2-Ethylhexanol concentration of over 336 μg/m3 showed a high prevalence of such complaints.
Therefore, 2-Ethylhexanol was estimated that the threshold at which symptoms appeared excessively in a population should be in the range of 65.5‐336 μg/m3.
In Finland, several respiratory and dermal symptoms and irritation in the eyes were reported in environments with 2-Ethylhexanol concentration of 1‐4 μg/m3.
In a rehabilitation center in Sweden, where airborne concentrations of 2-Ethylhexanol were very low (0.3‐0.6 μg/m3 ), the staff who had been previously exposed to VOCs as well as 2-Ethylhexanol developed SBS symptoms after 2 days of re‐exposure regardless of a 4‐month period without VOC exposure.
In a newly built university building in Japan, as the indoor concentration of 2-Ethylhexanol decreased by ventilation, the number of occupants who complained about headache and eye irritations decreased.
At a technical university in Switzerland, employees and students had complained about deteriorated indoor air quality after the building was renovated.
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.2-Ethylhexanol , also called octanol, is an 8-carbon higher alcohol species.
2-Ethylhexanol is hardly soluble in water, but is soluble in almost all organic solvents.
2-Ethylhexanol has very low-level impurities and may be used as a raw material for a wide variety of chemicals.
The largest market for 2-Ethylhexanol has been the plasticiser dioctyl phthalate (DOP) which is used in the manufacture polyvinyl chloride (PVC) products.
An issue for 2-Ethylhexanol producers is that DOP has been dogged by health hazard and environmental concerns.
In Europe, DOP and some other phthalate plasticisers have been banned in children’s articles or children’s articles that can be put in their mouths.
There are a number of other uses for 2-Ethylhexanol.
2-Ethylhexanol is used as a low volatility solvent for resins, waxes, animal fats, vegetable oils, disinfectants and insecticidal sprays, and petroleum derivatives.
2-ethyl hexonol derivatives are used as an additive for diesel fuel to reduce emissions and to improve the performance of lube oils and mining chemicals.
2-Ethylhexanol can be used in very low concentrations for aqueous anti-foam formulations used in the textiles and paper industries.
2-Ethylhexanol is used in the production of the diester of maleic acid, which is a starting material for surfactants, while it is a feedstock for 2-Ethylhexanol sulphate for use as a surfactant for electrolytes.
The general population may be exposed to 2-Ethylhexanol from inhalation of ambient air, ingestion of food and drinking water, or dermal absorption of this compound or other products containing 2-Ethylhexanol.
Studies have reported 2-Ethylhexanol emission from various sources, such as carpets, furnitures, computers, books and food wrappings.
Building materials, such as insulation and gypsum board, wallpaper, paint, PVC flooring, and adhesives, are also sources of 2-Ethylhexanol emissions.
Several reports point out that flooring is a prominent source of 2-Ethylhexanol air pollution in buildings.
The region of the highest 2-Ethylhexanol concentrations in apartment houses was concrete slabs surface, which was directly in contact with a vinyl carpet.
In a school conference room with a 2-Ethylhexanol air concentration of 1902 µg/m3 , the rates of 2-Ethylhexanol emission from the carpet tile and concrete surface beneath the carpet were 2492 μg/h/m2 and 12,697 μg/h/ m2 , respectively, measured using the double‐cylinder chamber method.
2-Ethylhexanol was also reported that 2-Ethylhexanol concentrations in the air increased with the amount of 2-Ethylhexanol emitted from the floor.
Using the FLEC method, 2-Ethylhexanol was detected after PVC flooring was directly attached to a concrete floor60 or after PVC flooring material was tightly attached to a self‐leveling (SL) material.
The amount of 2-Ethylhexanol emission increases as the moisture content of an SL material increases.
Taken together, long‐term emission of 2-Ethylhexanol can be attributed to the hydrolysis of DEHP contained in the flooring material,supported by the fact that 2-Ethylhexanol concentration in the air decreases significantly after plastic coverings, adhesives, and leveling layers are removed from the floor, all while the rooms were warmed to 55°C and simultaneously ventilated by additional exhaust fans for a week.
Several published studies have reported on various materials that emit 2-Ethylhexanol.
We postulated, based on the amount of 2-Ethylhexanol emission from flooring that compounds containing a 2‐ethyl‐1‐hexyl moiety, such as DEHP contained in PVC, and 2‐ethy hexyl acrylate contained in adhesives, are hydrolyzed to emit 2-Ethylhexanol when the backing of carpeting material was in contact with concrete floors.
Some employees even suffered from sickness and headache.
Indoor concentration of 2-Ethylhexanol was 4‐17 µg/m3 .
As described above, there are reports which claim that 2-Ethylhexanol is present indoors, even in a general living environment.
Possibly causing irritation and inflammation in the mucous membranes of the respiratory tract and nasal cavity.
However, the dose‐response relationship and the discrepancy in the lowest‐observed‐adverse‐effect‐level (LOAEL) among the countries remain to be further clarified.
Experimental inhalation or topical exposure settings To assess the acute effects of 2-Ethylhexanol, volunteers were exposed to 2-Ethylhexanol vapor (1 mg/m3 ) for 2 hours.
During exposure, the volunteers reported a significant increase in nasal and eye discomfort.
No differences in response were observed between the sexes, or between the atopic and nonatopic treatments.
Twenty‐four young men were assessed before, during, and after the 4‐hour exposure.
As 2-Ethylhexanol concentration increased in three levels, 8.14, 56.6, and 116 mg/m3 , nasal flow reduction and substance P concentration were increased.
To evaluate the effect of 2-Ethylhexanol on sensory irritation, 2-Ethylhexanol at mean concentrations of 1.5, 10, and 20 ppm (7.98, 53.2, and 106 mg/m3, respectively) were used for either constant or variable for the 4‐hour exposure.
USES:
Main application is as a feed stock in the manufacture of low volatility esters, the most important of it is Di-Octyl Phthalate (DOP or DEHP)
As low volatility Solvent for resins, animal fats, vegetable oils etc.
As low-volatility ingredient in solvent blends for dye stuffs & coating industries
Additive in dispersing & wetting agents for pigment pastes.
Feed stock in the manufacture of Ethoxylates & extractents for heavy metals.
Used in the production of derivatives like Di-Octyl Adipate, Di-Octyl Maleate, etc.
Feed stock in the manufacture of 2-Ethyl Hexyl Sulphate which is used as a surfactant for Electrolytes.
Used in the production of 2-Ethyl hexyl esters, which serves as thermal stabilizers and antioxidants/plastics.
Used in anti-foams for almost all aqueous systems.
Preparation Distribution Lacquers
cleaning agents
diluting a concentrated solution
oil drilling fluid
functional fluids
laboratory chemicals
intermediates
USAGE AREAS:
Paints & Coatings
Lubricants
Research Chemicals
Cleaning Products
Chemical Manufacturing
APPLICATIONS:
2-Ethylhexanol is used to make plasticizers for polyvinyl chloride.
Reaction with phthalic anhydride gives bis(2-ethyl hexyl) phthalate (DOP, DEHP).
Reaction with adipic acid gives bis(2-ethyl hexyl) adipate.
Moreover, esterification with acrylic acid gives 2-ethyl hexyl acrylate for use in adhesives and paints.
On the other hand, because it can dissolve many organic materials well, 2-Ethylhexanol is widely used as a low-volatility solvent.
Adhesives/sealants-B&C
Ag chem solvents
Agriculture intermediates
Architectural coatings
Auto OEM
Auto refinish
Automotive parts & accessories
Building materials
Construction chemicals
Diesel imed
Equipment & machinery
Gasoline intermediate
General industrial coatings
Graphic arts
Herbicides - intermediate for 2,4-d
Herbicides - intermediate for other
Industrial fuel imeds
Lubricants
Marine
Paints & coatings
Pipe non-food contact
Plasticizer
Process solvents
Protective coatings
Soap/detergents
Wetting agent
Wood coatings
CHARACTERISTICS:
2-Ethylhexanol (2EH), also called octanol, is an 8-carbon higher alcohol species.
2-Ethylhexanol is hardly soluble in water, but is soluble in almost all organic solvents.
ATTRIBUTES:
Defoaming, wetting, and dispersing characteristics
Excellent reactivity as an intermediate
Improves flow and gloss in baking finishes
Inert - Food use with limitations
Inert - Nonfood use
Inherently biodegradable
Non-HAP
Non-SARA
Slow evaporation rate
Very low water miscibility
PROPERTIES:
Quality Level: 100
vapor density: 4.49 (vs air)
vapor pressure: 0.2 mmHg ( 20 °C)
assay: ≥99.6%
autoignition temp.: 550 °F
expl. lim.: 0.88 %, 104 °F, 9.7 %, 113 °F
refractive index: n20/D 1.431 (lit.)
bp: 183-186 °C (lit.)
mp: −76 °C (lit.)
solubility: water, soluble g/L at 20 °C
FEATURES:
Readily forms esters with various acids
Very limited miscibility with water
Low volatility solvent
Enhances flow and gloss in baking finishes
Non-HAP (Hazardous Air Pollutant) Solvent
