2-ETHYLHEXANOIC ACID

2-Ethylhexanoic acid

2-Ethylhexanoic acid is the organic compound with the formula CH3(CH2)3CH(C2H5)CO2H. It is a carboxylic acid that is widely used to prepare lipophilic metal derivatives that are soluble in nonpolar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.

2-ethylhexanoic acid
Skeletal formula of 2-ethylhexanoic acid
2-Ethylhexanoic acid molecule
Names
IUPAC name
2-Ethylhexanoic acid [1]
Identifiers
CAS number
149-57-5 ☑
72377-05-0 S enantiomer ☒
56006-48-5 enantiomer R ☒
3D model (JSmol)
Interactive image
Reference Beilstein 1750468
CHEMBL
ChEMBL1162485 ☑
ChEMBL1162487 ☒
ChEMBL1162486 ☒
ChemSpider
8373 ☑
70431 R ☒
119200 S ☒
ECHA Info Card 100.005.222
CE number
205-743-6
Mesh 2-ethylhexanoic acid +
PubChem CID
8697
78052 R
135309 S
RTECS number
MO7700000
UNII
01MU2J7VVZ ☑
CompTox Dashboard (EPA)
DTXSID9025293 Edit this on Wikidata
InChI [show]
Smiles [show]
Properties
Chemical formula C 8 H 16 O 2
Molar mass 144.214 g mol −1
Appearance Colorless liquid
Density 903 mg mL −1
Melting point -59.00 ° C; -74.20 ° F; 214.15K
Boiling point 228.1 ° C; 442.5 ° F; 501.2K
log P 2.579
Vapor pressure <1 Pa (at 25 ° C)
Acidity (p K a) 4.819
Basicity (p K b) 9.178
Refractive index (n D) 1.425
Thermochemistry
Enthalpy of
std formation (Δ f H ⦵ 298) −635.1 kJ mol −1
Enthalpy of
standard combustion (Δ c H ⦵ 298) -4.8013–4.7979 MJ mol −1
Dangers
GHS pictograms GHS05: Corrosive GHS07: Harmful GHS08: Danger to health
SGH Danger signal word
GHS Hazard Statements H312, H318, H361
GHS precautionary statements P280, P305 + 351 + 338
breaking point 114 ° C (237 ° F; 387 K)
auto - ignition
temperature 371 ° C (700 ° F; 644 K)
Explosive limits 0.9 to 6.7%
Lethal Dose or Concentration (DL, LC):
LD 50 (median dose)
1.142 g kg -1 (skin, rabbit)
3 g kg -1 (oral, rat)
Related compounds
Related compounds
2-methylhexane
3-methylhexane
Valnoctamide
2-Methylheptane
3-Methylheptane
2-Ethylhexanol
Valproic acid
Propylheptyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 ° C [77 ° F], 100 kPa).
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Infobox references
2-Ethylhexanoic acid is the organic compound with the formula CH 3 (CH 2) 3 CH (C 2 H 5) CO 2 H. It is a carboxylic acid widely used to prepare lipophilic metal derivatives soluble in non-polar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.

Production
2-Ethylhexanoic acid is produced industrially from propylene, which is hydroformylated to give butyraldehyde. Aldol condensation of the aldehyde gives 2-ethylhexenal, which is hydrogenated to 2-ethylhexanal. Oxidation of this aldehyde gives the carboxylic acid. [2]

Metal ethylhexanoates

65% solution of cobalt (II) bis (2-ethylhexanoate) in mineral spirits, bottle tilted to illustrate color and viscosity.
2-Ethylhexanoic acid forms compounds with metal cations which have stoichiometry in the form of metal acetates. These ethylhexanoate complexes are used in organic and industrial chemical synthesis. They function as catalysts in polymerizations as well as for oxidation reactions as "oil drying agents". [3] They are very soluble in nonpolar solvents. These metal complexes are often described as salts. However, they are not ionic coordination complexes but with a neutral charge. Their structures resemble the corresponding acetates.

Examples of metal ethylhexanoates
Aluminum hydroxyl bis (2-ethylhexanoate), used as a thickener
Tin (II) ethylhexanoate (CAS # 301-10-0), a catalyst for polylactide and poly (lactic-co-glycolic acid). [4]
Cobalt (II) ethylhexanoate (CAS # 136-52-7), a dryer for alkyd resins
Nickel (II) ethylhexanoate (CAS # 4454-16-4)
See as well
2-ethylhexanol

Properties
Related categories Building blocks, C8, Carbonyl compounds, Carboxylic acids, Chemical synthesis,
Organic building blocks
Less...
Quality level 200
vapor density 4.98 (vs air)
vapor pressure <0.01 mmHg (20 ° C)
  10 mmHg (115 ° C)
test ≥99%
self-ignition temp. 699 ° F
expl. lim. 1.04%, 135 ° F
Show more (15)
The description
General description
2-Ethylhexanoic acid (EHXA, 2-Ethylhexanoic acid) is an industrially important aliphatic carboxylic acid. [2] It is widely used as a stabilizer [1] and as a wood preservative. [1]
It has various industrial applications, such as: [3]
• coolant in automobiles
• synthetic lubricant
• wetting agent
• co-solvent
• paint drying
• anti-foam agent in pesticides

2-Ethylhexanoic acid is a branched chain fatty acid.

ChEBI
2-Ethylhexanoic acid is found in fruits. 2-Ethylhexanoic acid is found in grapes.

Human Metabolome Database (HMDB)
2-ethylhexanoate (isobaric with 2-propylpentanoate), also  t known as 2-ethylhexanoic acid, is classified as a member of medium chain fatty acids. Medium chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Ethylhexanoate (isobaric with 2-propylpentanoate) is considered to be slightly soluble (in water) and acidic.

Help on calculated properties New window
Property name Property value Reference
Molecular weight 144.21 g / mol calculated by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3 2.6 calculated by XLogP3 3.0 (PubChem release 2019.06.18)
Number of hydrogen bond donors 1 calculated by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Number of hydrogen bond acceptors 2 calculated by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Number of rotary links 5 calculated by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact mass 144.11503 g / mol calculated by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic mass 144.11503 g / mol calculated by PubChem 2.1 (PubChem release 2019.06.18)
Topological polar surface 37.3 Ų calculated by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Number of heavy atoms 10 calculated by PubChem
Formal load 0 calculated by PubChem
Complexity 99.4 calculated by Cactvs 3.4.6.11 (PubChem version 2019.06.18)
Number of isotopic atoms 0 calculated by PubChem
Defined number of atomic stereocenters 0 calculated by PubChem
Number 1 of undefined atomic stereocenter calculated by PubChem
Defined number of bond stereocenters 0 calculated by PubChem
Number of undefined binding stereocentre 0 calculated by PubChem
Number of covalently bound units 1 calculated by PubChem
The compound is canonized Yes

The description

Molecular Formula: C8H16O2

Main synonyms
French names:

2-BUTYLBUTANOIC ACID
2-ETHYLCAPROIC ACID
2-ethylhexanoic acid
3-HEPTANECARBOXYLIC ACID
2-ethylhexanoic acid
2-ethylhexanoic acid (racemic)
ALPHA-ETHYLCAPROIC ACID
BUTYLETHYLACETIC ACID
Ethylhexanoic acid
English Names:

2-ethylhexanoic acid
2-ethylhexanoic acid
2-Ethylhexanoic acid (racemic)
Ethylhexanoic acid
Use and sources of emission 1 2 3
2-ethylhexanoic acid is used as an intermediate in the manufacture of:

of metallic salts, used as:
drying agents in paints and varnishes
gelling agents in hydrocarbons
esters to form plasticizers such as polyvinylbutyral (PVB) resin
alkyd resins
dyes
of pharmaceutical products
catalysts.

2-Ethylhexanoic acid (2-Ethylhexanoic acid)
CAS Registry Number 149-57-5

What is it about?
2-Ethylhexanoic acid, also known as 2-Ethylhexanoic acid, is an industrial chemical.
How is it used?
2-Ethylhexanoic acid is largely used in the preparation of metal salts and soaps which serve as desiccants in paints and inks, and as thermal stabilizers in polyvinyl chloride (PVC).
2-Ethylhexanoic acid is also used in the manufacture of resins used in automotive windshields and vinyl flooring.
2-Ethylhexanoic Acid is not manufactured in Canada, but is imported there.
Why did the Government of Canada assess it?
Prior to evaluation, 2-Ethylhexanoic acid was determined to present a potential hazard to human health due to its classification by international organizations as a substance that can cause fetal developmental disorder in laboratory animals. and based on a high potential for exposure (excluding occupational exposure) for the general population of Canada.
2-Ethylhexanoic Acid has not been considered a high priority for its environmental risk assessment. However, the potential effects on the environment were also considered in this screening assessment.
How are Canadians exposed to it?
The general population of Canada may be exposed to 2-Ethylhexanoic Acid during the use of paints, antifreeze, products containing PVC and other products containing metal salts of 2-Ethylhexanoic Acid; however, this exposure is expected to be low.
How is it released into the environment?
Releases of 2-Ethylhexanoic Acid to the environment can arise from various waste streams as a result of its production, use and environmental degradation of certain plasticizers.
What are the results of the evaluation?
The Government of Canada has completed a science assessment of 2-Ethylhexanoic acid, called a screening assessment.
Screening assessments determine the potential risk to the general population (excluding exposure in the workplace) and the environment.
The indicate that 2-Ethylhexanoic acid is not expected to remain in the environment for a long time, nor to accumulate in organisms.
In addition, the amount of 2-Ethylhexanoic acid that can be released into the environment is below the toxic threshold for organisms.
The Government of Canada has therefore concluded that 2-Ethylhexanoic acid is not entering the environment in amounts or under conditions that endanger the environment.
The Government of Canada has also concluded that 2-Ethylhexanoic Acid is not hazardous to the health of the general population at current levels of exposure.
What is the Government of Canada doing?
Due to its use in large volumes, the Government of Canada is proposing to study whether it would be useful to include 2-ethylhexanoic acid in the Environmental Emergency Regulations, to ensure that measures in terms of prevention, preparedness, response and recovery are in place.
Based on the conclusions of the final assessment, the Government of Canada proposes that no further action be taken with respect to 2-Ethylhexanoic Acid.
The final screening assessment report was released to the public on September 10, 2011.
What Can Canadians Do?
The health risks of a chemical depend on the type of hazard the substance is likely to present (its potential to cause harm) and the dose (the degree of exposure to the substance). 2-Ethylhexanoic acid is not of concern for the environment or human health at the current level of exposure.
As a precaution, Canadians are reminded to carefully observe the warnings and directions for use of any product they use.
Canadians who handle 2-Ethylhexanoic Acid in the workplace should consult with their occupational health and safety representative for safe handling practices, applicable laws, and requirements under the Information System on Occupational Health and Safety. hazardous materials used at work (WHMIS).

2-Ethylhexanoic acid is the organic compound with the formula CH3 (CH2) 3CH (C2H5) CO2H. It is a carboxylic acid widely used to prepare lipophilic metal derivatives soluble in nonpolar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.

2-Ethylhexanoic acid is produced industrially in two stages from butyraldehyde. Aldol condensation of the aldehyde gives 2-ethylhexanal. Oxidation of the latter gives the carboxylic acid.

METALLIC ETHYLHEXANOATES

These derivatives containing lipophilic metals are used in many ways as catalysts in polymerizations, oxidation (drying agents) and organic synthesis. The high solubility of these metal complexes is attributable to the long hydrocarbon chain and to the presence of a chiral center which leads to mixtures of enantiomeric complexes. These metal complexes, which exist as mixtures of several diastereomers, are often described as salts. However, they are not ionic coordination complexes but neutral in charge. Their structures resemble the corresponding acetates.

GENERAL DESCRIPTION

2-Ethylhexanoic acid (EHXA, 2-EHA) is an industrially important aliphatic carboxylic acid. It is widely used as a stabilizer and as a wood preservative.
It has various industrial applications, such as:
• coolant in automobiles
• synthetic lubricant
• wetting agent
• co-solvent
• paint drying
• anti-foam agent in pesticides

PHARMACOLOGY AND BIOCHEMISTRY
ABSORPTION, DISTRIBUTION AND EXCRETION

The disposition of di-2- (ethylhexyl) adipate in humans after administration of the stable isotope-labeled test substance was investigated. Blood and urine samples were taken from six male volunteers after administration of 46 mg of 2H10-labeled di-2- (ethylhexyl) adipate. Blood was collected 0.5, 1, 2, 3, 4, 5, 6, 8 and 12 hours after administration. Urine was collected up to 96 hours after administration. No adverse effects were observed in any of the volunteers and no significant change in biochemical or hematological parameters was observed. The plasma did not contain any parent molecules; however, the 2-ethylhexanoic acid metabolite was detected, but the levels were below the limit of quantification. 2-Ethylhexanoic acid, as a conjugate, was also the major metabolite detected in urine.
 no metabolites were detected in urine. Conjugated 2-ethylhexanoic acid in the urine averaged 8.6% of the administered dose. An additional 3.5% of the dose consisted of 2-ethyl-5-hydroxyhexanoic acid, 2-ethylhexanedioic acid, 2-ethyl-5-keto-hexanoic acid and 2-ethylhexanol. / It was / concluded that 2-ethylhexanoic acid is an appropriate marker for biological monitoring in the estimation of di-2- (ethylhexyl) adipate dietary intake because it is the main metabolite identified and its level elimination is similar to that of other di-2- (ethylhexyl) adipate metabolites.
[2-14 (C) -Hexyl] 2-ethylhexanoic acid in corn oil was administered to female Fischer 344 rats either as a single oral gavage at 100 or 1000 mg / kg, or after 14 days of unlabeled oral 2-ethylhexanoic acid (100 mg / kg only). An aqueous solution of [2-14 (C) -hexyl] 2-ethylhexanoic acid was applied topically at 100 or 1000 mg / kg and another group of rats received 2-ethylhexanoic acid by intravenous injection. (1 mg / kg). Urine, feces, and blood were collected at various intervals over 96 hours. About 72 to 75 percent of the oral dose was excreted in the urine within 24 hours, and <10 percent was excreted after 24 hours. Approximately 50% of 14 (C) was excreted within the first 8 hours after the 100 mg / kg dose versus 20% after the 1000 mg / kg dose. Fecal excretion accounted for 7 to 12 percent of the two doses. After intravenous injection, 64 percent of l4 (C) was excreted in the urine and 2 percent in the stool. Repeated administration of unlabeled 2-ethylhexanoic acid (100 mg / kg) appeared to reduce urinary excretion of 14 (C) slightly to 55% in urine, while faecal excretion increased to 15% during the first 24 hours. After skin application, approximately 30 percent of the applied dose was excreted in the urine during the first 24 hours, followed by an additional 8 and 17 percent from 24 to 96 hours for the 100 and 1000 mg doses / kg, respectively. Fecal excretion was 7 percent for both doses. Skin absorption has been estimated between 63 and 70 percent compared to intravenous administration. After dermal application, peak blood concentrations of 14C occurred approximately 5.7 hours after application and the absorption half-life was 3.2 hours. The major urinary metabolites included 2-ethylhexanoic acid glucuronide, 2-ethyl-6-hydroxyhexanoic acid and 2-ethyl-1,6-hexanedioic acid glucuronide, and non-2-ethylhexanoic acid. metabolized. The proportions of each metabolite changed with dose and route of administration.

Male Wistar rats given 2-ethylhexanoic acid in drinking water (600 mg / kg per day) for 9 weeks eliminated 10 different metabolites, including 2-ethyl-1,6-hexanedioic acid, l 2-ethyl-6-hydroxyhexanoic acid, five other hydroxylated metabolites and two lactones, unsaturated 5,6-dehydro-2-ethylhexanoic acid and the parent compound (partly as a glucuronic acid conjugate).

MANUFACTURING METHODS

Produced by the aldol route from butyraldehyde in three stages: aldol condensation; hydrogenation of the carbon-carbon double bond; and the oxidation of the saturated branched chain aldehyde to 2-ethylhexanoic acid.
2-Ethylhexanoic acid is produced by oxidation of 2-ethyl-1-hexanol or 2-ethylhexanal; the latter is obtained with a yield of 95% by hydrogenation of 2-ethyl-2-hexenal, itself formed by the aldol condensation of n-butyraldehyde.

REACTIVITY PROFILE

2-Ethylhexanoic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They thus react with all bases, both organic (for example amines) and inorganic. Their reactions with the bases, called “neutralizations”, are accompanied by a substantial release of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six carbon atoms or less are freely or sparingly soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociates to some extent in water to give hydrogen ions. The pH of the carboxylic acid solutions is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve when neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form hydrogen gas and a meta salt. llique. Such reactions in principle also occur for solid carboxylic acids, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids can absorb enough water from the air and dissolve in it enough to corrode or dissolve iron, steel and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate hydrogen cyanide gas. The reaction is slower for dry solid carboxylic acids. Insoluble carboxylic acids react with cyanide solutions to cause the release of hydrogen cyanide gas. Flammable and / or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides and sulfides. Carboxylic acids, particularly in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and / or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but always heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids can initiate polymerization reactions; like other acids, they catalyze (often accelerate) chemical reactions.