2-ETHYLHEXANOL

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

Identification of the substance: 2-Ethyl-1-hexanol
CAS number: 104-76-7
EC Number: 203-234-3

Synonyms:
2-Ethylhexanol
2-Ethylhexyl alcohol
Ethylhexanol (non-specific name)
2-Ethylhexan-1-ol
2-Éthylhexane-1-ol
2-Etilhexan-1-ol

2-ethyl hexanol appears as a dark brown liquid with an aromatic odor. 2-ethyl hexanol is insoluble in water and less dense than water.

The main uses for 2-ethylhexanol (2-EH) is in the production of plasticisers, coatings, adhesives and other speciality chemicals.

2-Ethylhexanol has low volatility and enhances the flow and gloss of baking enamels. It is also used as dispersing agent for pigment pastes.

2-ethylhexan-1-ol is a primary alcohol that is hexan-1-ol substituted by an ethyl group at position.
It has a role as a volatile oil component and a plant metabolite.

2-Ethylhexanol is most commonly used in production of phthalates for rubber and plastic fabrication. It is also used as a low volatility solvent and an active component of textile finishing formulations.

2-Ethylhexanol is a colourless liquid. 2-Ethylhexanol is a precursor for production of plasticisers used to manufacture cable insulation and car interior materials. It is used as a solvent for plastics and varnishes, defoamer, fragrance compound, as well as in the production of herbicides, Cetane Improver additives and additives to oils. 2-Ethylhexanol esters are used in the production of food packaging materials.

ChEBI

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

CAS Number: 104-76-7
HS Number: 29051685

2-Ethylhexan-1-ol; 2-Ethyl-1-Hexanol; 2-Ethylhexyl alcohol

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-Ethyl-1-hexanol
Synonym: Isooctyl alcohol

CAS Number 104-76-7
Linear Formula CH3(CH2)3CH(C2H5)CH2OH
Molecular Weight 130.23
Beilstein/REAXYS Number 1719280
EC Number 203-234-3
MDL number MFCD00004746
PubChem Substance ID 24878263
NACRES NA.22

2-ethylhexanol is a clear, mobile and neutral liquid with a characteristic odour.
2-ethylhexanol is miscible with most common organic solvents but its miscibility with water is very limited.
2-ethylhexanol enters into the reactions that are typical of primary alcohols.
For instance, 2-ethylhexanol readily forms esters with various acids.

2-Ethylhexanol
CAS: 104-76-7

2-Ethylhexanol (2-Ethylhexanol) is a clear, colorless, fatty alcohol that is insoluble in water but soluble in most organic solvents.
2-Ethylhexanol can be readily converted into esters that have a variety of uses.
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.

Product description
2-Ethylhexanol is an eight-carbon branched chain oxo alcohol having a high boiling point and slow evaporation rate.
It is a versatile solvent featuring excellent reactivity as a chemical intermediate. It serves as a chain terminator in synthesizing condensation polymers and as an intermediate for plasticizers. Eastman™ 2-Ethylhexanol has low volatility and enhances the flow and gloss of baking enamels. It is also used as dispersing agent for pigment pastes.

The chemical substances for this product are listed as Inert Ingredients Permitted for Use in Nonfood Use Pesticide Products, and in Food Use Pesticide Products with limitations, under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA). For details on specific permissions, click here.

2-Ethyl Hexanol (2-EH) is a clear, uniform, nontoxic liquid with a characteristic odor, insoluble in water, soluble in organic solvent. It is obtained indirectly in OXO synthesis from propylene and synthesis gas.

General description
2-Ethyl-1-hexanol is a monohydroxy alcohol reagent. It is a glass-forming alcohol.[1]

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.

2-ETHYL HEXANOL
(.+-.)-2-ETHYL-1-HEXANOL
2-ETHYL-1-HEXANOL
ETHYLHEXANOL
2-ETHYLHEXANOL
2-ETHYLHEXYL ALCOHOL

2-Ethylhexanol
2-Ethyl-1-hexanol
2-Ethylhexyl Alcohol
Isooctanol
Octyl Alcohol

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

Applications
Manufacture of low volatility esters (for example, dioctylphthalate)
Low volatility solvent (for resins, animal fats, waxes, vegetable oils and petroleum derivatives)
Coatings
Ethoxylates
Herbicides
Extractant production (heavy metals)

Physical properties
Molecular Weight: 130.23
Relative Evaporation Rate nBuAc=1 <0.01
Vapor Pressure at 20C, mmHg: 0.06
Density at 20 C lb/gal: 6.94
Specific Gravity at 20/20 C : 0.833
Viscosity at 20C cP 10.3
Surface Tension
(dynes/cm at 20C) 26.9
(dynes/cm at 25C) –
Hansen Solubility Parameters
Total 9.9
Non-Polar 7.8
Polar 1.6
Hydrogen Bonding 5.8
Boiling Point, C at 760mm Hg 184.6
Solubility at 20C
%Wt In Water 0.07
%Wt Water in 2.6
Closed Cup Flash Point F 162
SARA 313 (see note 1†) N
Hazardous Air Pollutant (see note 2††) N
† Note 1: Superfund Amendments and Reauthorization Act of 1986 (SARA) Title III
Section 313
†† Note 2: Hazardous Air Pollutants listed under Title III of the Clean Air Act
Classification/Registry Numbers
CAS Number 104-76-7
EINECS 203-234-3

2-ETHYLHEXANOL is a clear, high-boiling point and low volatility solvent with a characteristic odor.

2-ETHYLHEXANOL is miscible with most organic solvents but has very limited miscibility with water.

Uses:
Stabilizers
Plasticizers
Coatings additives
Lubricants
Pharmaceuticals
Pesticides
Perfumes
Food additives
Preservatives
Chemical intermediates

Benefits:
Low molecular weight
Water-soluble
Provide proper balance of desired properties in a formulation.

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.

Substance name:2-ethyl-1-hexanol
Trade name:Ethyl Hexanol
EC no:203-234-3
CAS no:104-76-7
HS code:29051685
Formula:C8H18O
Synonyms:1-hexanol, 2-ethyl- / 2-EH (=2-ethyl hexanol) / 2-EH alcohol / 2-ethyl 2-hexan-1-ol / 2-ethyl hexanol / 2-ethyl hexyl alcohol / 2-ethylhexan-1-ol / 2-ethylhexanol / alcohol C8 / corexit 8814 / ethylhexanol / EXXAL 8 / FORMULA No 91270 / isooctanol (=2-ethyl-1-hexanol) / isooctyl alcohol (=2-ethyl-1-hexanol) / octyl alcohol (=2-ethyl-1-hexanol) / octyl alcohol(2-EH)(=2-ethyl-1-hexanol) / Substances with a flash-point above 60 °C and not more than 100 °C / Substances with a flash-point above 60 °C and not more than 100 °C, which do not belong to another class)

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.
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 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.

Properties and applications
The branching in 2-ethylhexanol inhibits its crystallization due to packing disruption; this results in a very low freezing point.
Esters of 2-ethylhexanol are similarly affected and it therefore finds application as a feedstock in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points.

A significant portion of 2-ethylhexanol manufactured is used as a precursor for the synthesis of the diester bis(2-ethylhexyl) phthalate (DEHP), a plasticizer.
Because it is a fatty alcohol, its esters tend to have emollient properties.
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.
It can be used in the development of photos, production of rubber and extraction of oil and gas.

Industrial production
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.

Synthesis of 2-Ethylhexanol

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.[8]

Health effects
2-Ethylhexanol exhibits low toxicity in animal models, with LD50 ranging from 2-3 g/kg (rat).
2-Ethylhexanol has been identified as a cause of indoor air quality related health problems, such as respiratory system irritation, as a volatile organic compound.
2-Ethylhexanol is emitted to air from a PVC flooring installed on concrete that had not been dried properly.[

Nomenclature
Although isooctanol (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives, IUPAC naming conventions dictate that this name is properly applied to another isomer of octanol, 6-methylheptan-1-ol.
The Chemical Abstracts Service likewise indexes isooctanol (CAS# 26952-21-6) as 6-methylheptan-1-ol.

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 used mainly in manufacturing plasticizers. 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.

General Description
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.

Chemical Reactivity
Reactivity 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.

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.

Chemical 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.
2-Ethylhexanol Preparation Products And Raw materials

Raw materials
HEAVY CUT RESIDUE OIL 2-Amino-3-chlorobenzoic acid Crotonaldehyde PROPYLENE Butyraldehyde ALDOL
Preparation Products
polyoxyethylene isooctyl ether phosphate 2-Ethylhexyl acrylate AZELAIC ACID DI(2-ETHYLHEXYL) ESTER ISOOCTYL THIOGLYCOLATE 2-Methyl-1-propanol Triisooctyl phosphite 2-Ethylhexyl diphenyl phosphate Bis(2-ethylhexyl) phosphate Dioctyl adipate Tris(2-ethylhexyl) phosphate Dioctyl sebacate Dioctyl maleate 2-Ethylhexanoic acid 2-METHOXY-5-(2′-ETHYLHEXYLOXY)BENZENE-1& SULFONATED ALIPHATIC POLYESTER SEBACIC ACID DI-N-OCTYL ESTER Di-(2-Ethylhexyl)4,5-Epoxytetrahydrophthalate 2-Ethylhexyl bromide DI-N-OCTYL PHTHALATE Di-(2-ethylhexyl)peroxydicarbonate bis(2-ethylhexyl) phenyl phosphite Dioctyl sulfosuccinate sodium salt Bis(2-ethylhexyl) adipate 2-ethylhexyl hydrogen -2-ethylhexylphosphonate Diisooctyl sebacate Bis(2-ethylhexyl) phthalate 2-Ethylhexylamine 1-Butanol 3-(Chloromethyl)heptane Antioxidant and antiseptic agent T202 Dibutyl maleate Dioctyl terephthalate

ALCOHOL C8ETHYL-1-HEXANOL, 2-FEMA 3151ISOOCTANOLISOOCTYL ALCOHOL’ISOOCTYL ALCOHOL’1-ETHYL-N-AMYLCARBINOL2-ETHYLHEXANOL2-ETHYLHEXYL ALCOHOL2-ETHYL-1-HEXANOL2EHOCTANOLOCTYL ALCOHOL2-Ethylhexanol 104-76-71-hexanol,2-ethyl-2-aethylhexanol2-ethvlhexanol2-ethyl-1-hexano2-ethyl2-hexan-1-o12-ethylhexan-2-ethylhexanol(flammableliquids,n.o.s.)2-ETHYL-1-HEXANOL 99.5+%2-Ethylhexan-1-ol2-Ethyl-l-hexanol2-Ethyl-1-hexanol,Isooctyl alcoholIsooctanol, extra pureIsooctanol, HPLC grade2-Ethylhexan-1-ol (1.5 mL)2-Ethyl-1-hexanol, 99% 1LT2-Ethyl-1-hexanol, 99% 5ML2-ETHYL-1-HEXANOL pure2-Ethylhexyl Alcohol Octanol Octyl Alcohol2-ETHYL-1-HEXANOL FOR SYNTHESISEthyl-1-hexa2-Ethyl-1-hexanol puriss., >=99.0% (GC)2-Ethyl-1-hexaHEPES STERILE 1M PH 7.32-Ethyl-hexanol-1ETHYLHEXANOL, 2-2-ETHYL-1-HEXANOL, >=99.6%2-ETHYL-1-HEXANOL, 99+%2EthylHexanol(Octanol)2-ethylhexanol,2-ethyl-1-hexanolOCTANOL,1-(SG)Aerofroth 88alcoolethyl-2hexyliqueEthylhexanolEthylhexyl alcoholHexan-1-ol, 2-ethylHexanol, 2-ethyl2-Ethylhexanol / isooctyl alcolol2-Ethyl-1-HexanolSolution(SecondSource),50,000mg/L,1ml2-Ethyl-1-HexanolSolution(SecondSource),50,000mg/L,2×0.6ml2-Ethyl-1-HexanolSolution,50,000mg/L,2×0.6ml2-Ethyl-1-hexanol>2-Ethyl-1-HexanolSolution,SecondSource,4000mg/L,1ml2-Ethyl-1-HexanolSolution,1000mg/L,1ml2-Ethyl-1-HexanolSolution,4000mg/L,1ml

Chemical Properties
colourless liquid
Chemical Properties

2-Ethyl-1-hexanol has a mild, oily, sweet, slightly floral odor reminiscent of rose and sweet, fatty-floral taste with a fruity note
Chemical Properties
2-Ethylhexanol is a clear, colorless liquid.

General Description
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.

Chemical 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.

2-Ethylhexanol Preparation Products And Raw materials
Raw materials
HEAVY CUT RESIDUE OIL 2-Amino-3-chlorobenzoic acid Crotonaldehyde PROPYLENE Butyraldehyde ALDOL

Synonyms:
2-Ethylhexanol
2-Ethylhexyl alcohol
Ethylhexanol (non-specific name)
2-Ethylhexan-1-ol
2-Éthylhexane-1-ol
2-Etilhexan-1-ol

The largest market for 2-EH has been the plasticiser dioctyl phthalate (DOP) which is used in the manufacture polyvinyl chloride (PVC) products.
An issue for 2-EH 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.
As a result, producers have been developing alternative plasticisers.
For example, BASF has switched from 2-EH to 2-propylheptanol (2-PH) to make a plasticiser called di-isononyl-cyclohexane dicarboxylate (DINCH) for use in sensitive applications where exposure to toxicological and exposure issues are of concern.
DINCH has received approval from the European Food Safety Authority (EFSA) for use in food contact applications such as cling film, tubes and sealants.
Citrates, or citric acid esters, are also being used as plasticisers for PVC products.
Other plasticisers such as trioctyl trimellitate, dioctyl adipate and dioctyl terephthalate can be made from 2-EH and the corresponding acid.
It is also used to make heavy metal salts to serve as thermal stabilizers for PVC.
However, a growing area for 2-EH has been its use in the manufacture of acrylate and methacrylate esters.
Their principal markets are acrylic emulsion polymers for pressure-sensitive adhesives, textiles and surface coatings, which includes high-solids automotive paints.
Demand for waterborne acrylic products that replace organic solvent-based products is being driven by increasingly stringent air emission regulations.
There are a number of other uses for 2-EH. It is used as a low volatility solvent for resins, waxes, animal fats, vegetable oils, disinfectants and insecticidal sprays, and petroleum derivatives.
2-EH derivatives are used as an additive for diesel fuel to reduce emissions and to improve the performance of lube oils and mining chemicals.
It can be used in very low concentrations for aqueous anti-foam formulations used in the textiles and paper industries.
2-EH 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-ethylhexyl sulphate for use as a surfactant for electrolytes.

Applications/uses
Adhesives/sealants-B&C
Agriculture intermediates
Architectural coatings
Auto OEM
Auto refinish
Automotive parts & accessories
Building materials
Construction chemicals
Diesel imed
Equipment & machinery
Gasoline intermediates
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

Key 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
REACH compliant
Slow evaporation rate
Very low water miscibility

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.

104-76-7 [RN]
1-Hexanol, 2-ethyl- [ACD/Index Name]
203-234-3 [EINECS]
2-Aethylhexanol [German]
2-Ethyl-1-hexanol [ACD/IUPAC Name]
2-Ethyl-1-hexanol [German] [ACD/IUPAC Name]
2-Éthyl-1-hexanol [French] [ACD/IUPAC Name]
2-ethylhexan-1-ol
2-Ethylhexanol [Wiki]
3151
Alcohol, 2-ethylhexyl
hexanol, 2-ethyl-
isooctanol
ISOOCTYL ALCOHOL
MP0350000
UNII:XZV7TAA77P
XZV7TAA77P
(??)-2-Ethyl-1-hexanol
(±)-2-ethylhexanol
104767 [Beilstein]
1-HEXANOL, 2-ETHYL-,
202480-75-9 [RN]
2-Ethyl-1-hexanol 100 Âµg/mL in Methanol
2-ethyl-1-hexanol 99%
2-ethyl-1-hexanol, ???
2-ethyl-1-hexanol, 99%
2-ethyl-1-hexanol，ar
2-Ethyl-1-hexanol-d17
2-Ethyl-1-hexyl alcohol
2-Ethyl-1-hexylalcohol
2-ethyl-hexan-1-ol
2-ethyl–hexanol
2-Ethyl-hexanol
2-ethylhexanol, 99%
2-ETHYLHEXANOL|2-ETHYLHEXAN-1-OL
2-Ethyl-hexanol-1
2-Ethylhexyl alcohol
2-乙基己醇 [Chinese]
4-01-00-01783 [Beilstein]
Ethyl-1-hexanol,2-
ETHYLHEXANOL
Ethylhexanol, 2-
Ethylhexyl alcohol
Hexan-1-ol, 2-ethyl
hexan-1-ol, 2-ethyl-
http://www.hmdb.ca/metabolites/HMDB0031231
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16011
Isocotyl alcohol, Isooctanol
Octyl alcohol
Q1Y4 & 2 [WLN]
Surfynol 104A

WHAT IS 2-ETHYLHEXANOL
2-Ethylhexanol (abbreviated 2-EH) is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents.

INCI: 2-Ethylhexanol
Chemical Formula: C8H18O
CAS Number: 104-76-7
PRODUCT SPECİFİCATİONS
CHARACTERİSTİCS
Chemical Formula   C8H18O
CAS Number   104-76-7
Molar Weight   130.231 g/mol
Melting Point   -76°C
Boiling Point   180-186°C
Flash Point   73°C

2-ETHYLHEXANOL FORMULA
2-Ethylhexanol is an organic compound that derives its name from a primary alcohol known as hexan-o-l with an ethyl group at position 2.
It is synonymously known as 2-Ethyl-1-hexanol or xi-2-Ethyl-1-hexanol.
The molecular formula is C8H18O and this compound is commonly abbreviated as 2-EH or 2EH.
The chemical is naturally found in corns, olive oil, tobacco, tea, blueberries and alcoholic beverages.

PROPERTIES OF 2-ETHYLHEXANOL
The average molecular weight of this compound is approximately 130.23g/mol.
2-Ethylhexanol belongs to a class of organic compounds known as fatty alcohols, and it’s a colorless liquid that is less soluble in water but soluble in most organic solvents.
It melts at -76° C and boils between 183-185° C and has an intense and unpleasant taste with a characteristic odor.
2-Ethylhexanol reacts violently with oxidants and strong bases while it readily forms esters with various acids.
When heated or burned, the substance decomposes by emitting acrid smoke and fumes.
It is a low-volatile solvent and the heat of combustion of 2-ethylhexanol is -1263.81 kcal/mol at 25° C while the heat of vaporization is about 10.8 kcal/mol at boiling point.

APPLICATIONS
2-Ethylhexanol is utilized in the manufacture of:

Soap detergents
Protective coats
Lubricants
Herbicides
Paints

It’s also used:
in processing other solvents
as a food additive

INDUSTRIAL USES
Industries may use 2-Ethylhexanol in the

Extraction of oil and gas
Production of cosmetics
Manufacture of plastics and rubber products
Development of photos and film
Making of anti-foam agents used in the textiles and paper industries
It can be used as a

Plating agent and surface treating agent
Adhesive and sealant
Corrosion inhibitor and anti-scaling agent
Intermediate industrial fuel
General industrial coating
SAFETY AND HAZARDS
As with other chemicals, 2-ethylhexanol requires handling with care and implementation of safety measures.
Some of the harmful effects this compound can cause if not handled appropriately include:

Skin irritations
Serious eye damage or irritation
Respiratory problems when inhaled
Headaches, dizziness, nausea and fatigue
PRECAUTIONS
When handling 2-ethylhexanol ensure that you:

Avoid inhaling vapors
Handle opened packages with protective gloves
Wash any part of your body that gets into contact with the compound with a lot of water
Keep away from sources of fire
Dispose of the contaminated gloves after use where necessary
Use protective glasses
Keep the container with this compound tightly closed in a dry, well-ventilated place
Even though 2-EH has a non-natural source, it can also be produced by the decomposition of plasticizers by microorganisms such as bacteria and fungi.
Synthetic construction materials also create it. It’s found in fruits such as cassava, raw and roasted earth almonds, raw beef and duck meat.
2-EH is less toxic to aquatic organisms and has low adverse effects on the environment.

2-Ethylhexanol Derivatives as Nonionic Surfactants: Synthesis and Properties
Wiesław Hreczuch, Karolina Dąbrowska, Arkadiusz Chruściel, Agata Sznajdrowska & Katarzyna Materna
Journal of Surfactants and Detergents volume 19, pages155–164(2016)Cite this article

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Abstract
The synthesis and basic properties of 2-ethylhexanol based innovative nonionic surfactants are described in this paper.
2-Ethylhexanol as an available and relatively inexpensive raw material was used as the hydrophobe source modified by propoxylation and followed by polyethoxylation.
As the result, six series of 2-ethylhexyl alcohol polyalkoxylates (EHP m E n ) were obtained with three steps of propoxylation, each followed by polyethoxylation and two series only with polyethoxylation (EHE n ). Two different catalysts were used, a dimetalcyanide and KOH.
Values of average conversion rates and chemical content of the obtained products (GC, TG and GPC techniques) were compared.
The influence of the applied catalyst and polyaddition degree on the homologue distribution, reactant conversion and amount of byproducts is discussed.
The basic physicochemical parameters including refractive index, solubility in polar media, foaming properties and wettability were investigated and compared.
Furthermore, surface activity parameters, i.e. surface tension (γ CMC) and critical micelle concentrations were determined.
Results are compared to C12–14 alcohol ethoxylates (LaE n ).
Accordingly, it was found that the studied 2-ethylhexyl alcohol based compounds are effective, low foaming nonionic surfactants.

Introduction
Surface active agents have a wide range of applications.
Approximately 60 % of all surfactants are used in cleaning formulations, including household detergents, cosmetics, toiletry and hygiene products.
Additionally, they are used in industrial cleaning (e.g. in situ) and as disinfection agents providing veterinary hygiene.
The rest of surfactants are used in agrochemical and industrial applications where “detergency” is not so important, i.e., construction, coatings, inks, herbicides.
Their global production reaches several million tons per year. Therefore, the impact of every new kind surfactant on humans and the environment must be investigated.
However, it can be observed that producers and consumers are not willing to cover the increased costs of natural raw materials.
This is exemplified by a surprisingly low market share of relatively expensive alkyl polyglucosides, in spite of their completely natural origin and good performance.
Thus, one of the most important elements to develop and implement innovative surfactants is searching for alternative sources—raw materials at competitive prices, which meet the required safety and environmental criteria.
An example of such a material is 2-ethylhexyl alcohol, which is widely available and relatively inexpensive, in comparison to C12–C14 alcohols.
These fatty alcohols which are commonly used in the synthesis of surface active agents usually have between 11 and 18 carbon atoms per molecule.
Generally, it is assumed that only then hydrophobic character of the hydrocarbon chain is sufficient for surfactants with suitable performance properties in the household and industrial applications for emulsification, wetting, washing or cleaning.
However, effective implementations of C10 or even C6 hydrophobes for cleaning purposes were reported in the literature [1, 2].

2-Ethylhexanol (2-EH) is an oxo alcohol, mostly used in the production of phthalate plasticizers (approx. 70 %) and acrylate esters (approx. 20 %).
As the result of a radical reduction in application of the 2-EH derived phthalates during the last decade, significant spare capacities of 2-ethylhexanol can be available for new applications at competitive prices.

2-Ethylhexanol polyoxyethylates have not been widely used as nonionic surfactants previously, because they are not amphiphilic enough.
Their share in the production of polyoxyethylates is assessed to be <1 %, which may mean values near zero in practice [3].

Polyaddition of oxirane is usually carried out in the presence of alkaline catalysts, mostly sodium and potassium hydroxides.
There are also known oxyalkylation catalysts, obtained from rare-earth metals, which provide a narrower range of homologue distribution and a relatively higher conversion of starter, as compared to the alkaline catalysts.
The alkoxylation reaction could include also the so called double metal cyanide (DMC) catalyst, which generates narrow range distribution of homologues.
DMC type catalyst is much more reactive than KOH. These catalysts are salts composed of cation of a transition metal and an anion complex built of the second transition metal atom coordinated with the complexing anion CN−.

The aim of this work was to investigate basic characteristics of 2-ethylhexyl alcohol derivatives as nonionic surfactants synthesized in the presence of innovative DMC catalyst and compare them with two groups of nonionic surfactants, one obtained with the traditional catalyst KOH, and the other constituted by dodecyl alcohol ethoxylates.
The studied series of products can be described by the following formula: EHP m E n , where 0 ≤ m ≤ 3, 3 ≤ n ≤ 12 and n, m are natural numbers, reflecting the average polyaddition degree of methyloxirane (P) and oxirane (E) (Scheme 1).
The concept of the 2-EH based surfactants seems to respond complex environment, economic, and application requirements on the global market of detergents.

The following chemicals were used as raw materials for the syntheses:

2-Ethylhexyl alcohol (molecular weight M w = 130 g mol−1), ≥99.5 % pure, manufactured by Azoty Nitrogen Works in Kędzierzyn-Koźle, Poland.

Oxirane (M w = 44 g mol−1), 99.9 % pure, manufactured by PKN ORLEN S.A., Plock, Poland;

Methyloxirane (M w = 58 g mol−1), manufactured by PCC Rokita S.A., in Brzeg Dolny, Poland;

Potassium hydroxide 85 %, analytical grade, purchased from Chempur, Piekary Śląskie, Poland;

DMC-based catalyst manufactured by MEXEO Company in Kędzierzyn-Koźle, Poland;

C12–C14 alcohol, acquired from PCC Rokita S.A., in Brzeg Dolny, Poland.

Synthesis
Ethoxylation and propoxylation reactions were performed in a procedure as found in the literature [5].
The syntheses were carried out using a 1-dm3 autoclave, which is composed of automatic mixer, heating mantle and cooler.
A pre-designed amount of alkylene oxide was introduced into the reactor charged with a weighed amount of starter and catalyst, following prior dehydration by a nitrogen purge at 120 °C for 20 min.
The syntheses were conducted at 130 °C. Then, the final product was kept for another 60 min at the reaction temperature.
At the end of synthesis, the product was cooled down and unloaded.

Measurements
Gas Chromatography Determination
Gas chromatography was conducted using a Perkin Elmer GC apparatus composed of a flame-ionization detector. Separation was conducted under specified conditions. The column temperature was programmed in the range 70–300 °C with the temperature raised at a rate 8 °C min−1, the injector and detector temperatures were set at 300 and 400 °C, respectively.
Argon was used as the carrier gas.

Thermogravimetric Measurements
Thermogravimetric analysis was performed using a Mettler Toledo Stare TGA/DSC1 unit (Leicester, UK) under nitrogen. Samples between 2 and 10 mg were placed in aluminium pans and heated from 30 to 450 °C at a heating rate of 10 °C min−1.

Density
Measurements of density were carried out with Rudolph Research Analytical densimeter.
The temperature was controlled and it was set up at 20 °C. Calibration was performed using deionized water and air as a reference substances.
The uncertainty of the measurements was <10−5 g cm−3.

Refractive Index
Measurements of the refractive indices were conducted using a Rudolph Research Analytical refractometer.
The temperature was controlled electronically and it was set at 20 °C. The uncertainty of measurements was <105.

Hydroxyl Number
The specified amount of sample was weighed into a 250-cm3 Erlenmeyer flask and recorded to the nearest 0.0002 g.
The specified amount of acetic anhydride–pyridine reagent was accurately pipetted into the flask, and a reflux condenser was attached.
The flasks were placed in the 95–100 °C oil bath for 15 min. Next, the flasks were removed from the oil bath, cooled and 10 cm3 of deionized water was added.
Using a dropper, 1 cm3 of phenolphthalein solution was added.
The burette was filled and the sample was titrated using methanolic potassium hydroxide to a faint pink color.
The hydroxyl value was calculated from the expression 56.1 v/m, where v is the difference, in cm3, between the two titrations and m is the quantity, in g, of the substance taken.

Cloud Point
Cloud point (CP) measurements of 1 % EHE n and EHP1E n butyldiglycol solutions (BDG) were determined and evaluated visually.
The solution was heated until it fully clouded. Then the solution was cooled down with stirring until clarified.
The cloud point was taken as the temperature at which the solution was completely transparent.
CP values were averaged over six measurements.

Foaming
The measurements were determined using a 1-dm3 cylinder loaded with 200 cm3 1 % solution of the sample. Then, 30 shakes for 30 s were performed.
After shaking, the height of the produced foam (mm) was measured.
The measurements were repeated after 1 and 10 min. Tests were performed three times for each sample.

Surface Tension
Surface tension measurements of the surfactant aqueous solutions were performed using a Drop Shape Analyzer from Krüss, Germany.
The accuracy of each measurement was ±0.01 mN m−1.
The temperature was set at 25 °C and controlled by a thermostatic bath.
The drop shape method was used.
Surface tension measurements were based on the camera image and calculated by analyzing the shape of the hanging drop using Laplace equation and specific software [6].
The values of the critical micelle concentration (CMC) were calculated using a linear regression analysis method.

Wettability
Measurements were carried out by the use of Drop Shape Analyzer DSA 100E (Krüss GmbH, Germany).
The basis for the determination of the contact angle is the image of the drop on the examined surface (paraffin).
After determination of actual drop shape and the contact line, the drop shape is adapted to fit a mathematical model used to calculate the contact angle.
The most exact method to calculate this value is Young–Laplace fitting (sessile drop fitting). The complete drop contour is evaluated.
After successful fitting of the Young–Laplace equation, the contact angle is determined as the angle between the solid/liquid and liquid/air phases.

Results and Discussion
Homologue Distribution
Derivatives of 2-ethylhexyl alcohol were synthesized by the polyoxyalkylation reaction.

Methyloxirane was added to 2-ethylhexanol in order to increase its hydrophobic character in the first step, followed by polyethoxylation, to obtain amphiphilic compounds.

Conclusions
Six series of 2-ethylhexanol alkoxylates were investigated as innovative surfactants, represented by a general formula EHP m E n , where m is a natural number within the range 0 ≤ m ≤ 3; surfactants were obtained with a KOH and a DMC-type catalyst, respectively.
Each of the series included ethoxylation products of average polyaddition degree (n) equal to 3, 6, 9 and 12.

It was confirmed that the DMC-type catalyst provides significantly narrower distribution of homologues and higher conversion of the starting material.
Additionally, higher selectivity and lower content of byproducts was also evidenced in the case of the DMC-type catalyst as compared to KOH.

The performed studies show that the DMC and KOH-derived EHP m E n surfactant series exhibit comparable physicochemical properties, as well as interfacial performance similar to that of reference C12–C14 alcohol ethoxylates.
Generally, the concept of insertion of P m blocks into the EHE n molecule was positively confirmed by its influence on relative decrease of the CMC values.
Moreover, the values of minimum surface area A min increase with the elongation of polyethylene ether chain.
This could be caused by the steric effect of the branched hydrophobes, as compared to the linear LaE n products, which can adsorb vertically at the interface.
Additionally, foam stability of the EHP m based ethoxylates was lower, as compared to that of their LaE n equivalents.
EHP m E n alkoxylates exhibit typical properties of low foaming nonionic surfactants and most of the physicochemical properties and surface activity is similar to that of the La-based surfactants.

Summarizing, EHP m E n alkoxylates obtained using a cheap and accessible raw material have a high potential for application.
Furthermore, the sterically specific structure of their hydrophobic moiety is very interesting.
herefore, this will be a subject of our further studies in more complex formulations.

Identification of the substance: 2-Ethyl-1-hexanol
CAS number 104-76-7
Synonyms:
2-Ethylhexanol
2-Ethylhexyl alcohol
Ethylhexanol (non-specific name)
2-Ethylhexan-1-ol
2-Éthylhexane-1-ol
2-Etilhexan-1-ol

2-EH is a branched, eight-carbon alcohol. After the lighter alcohols (those with one to four carbons such as methanol or butanol), 2-EH is the most important synthetic alcohol (Elvers et al 1989).
2-EH occurs naturally in food, is used as a flavor volatile(JECFA 1993), and is approved as an Indirect Food Additive by the U.S. Food and Drug Administration (FDA).
A flavor volatile is a compound naturally present in a food or added by the manufacturer.
In a food product these compounds may be present in the air about a food and when eaten and can affect the sensory properties of the food as it is hydrated and diluted with saliva.

Pesticides
In terms of pesticide use, 2-EH is used only as an inert ingredient.
There are currently no registered pesticide products containing 2-EH as an active ingredient.
2-EH is used as a solvent, cosolvent, adjuvant of surfactants, or defoamer in pesticide products used on agricultural food crops, animals, ornamental plants, and in residentialuse pesticides such as insect sprays.

Other Uses
Industrially, 2-EH is mainly used in the manufacture of ester plasticizers which are used in producing soft polyvinyl chloride.
The other major use of 2-EH is in the manufacture of a chemical used in the manufacture of coating materials, adhesives, printing inks, and impregnating agents.
In addition to its industrial uses, 2-EH is added to foods and beverages as a flavor volatile; there are two indirect FDA Food Additive uses for 2-EH

2-Ethyl hexanol: Solvent used below 10% in organic coating formulations when a late evaporating polar tail solvent is required. Also called isooctanol or isooctyl alcohol.

March 25, 2022

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2-ETHYLHEXANOL

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