2-Ethylhexanoic acid

Base Information

• Chemical Name: 2-Ethylhexanoic acid
• CAS No.: 149-57-5
• Deprecated CAS: 202054-39-5,83829-68-9,83829-68-9
• Molecular Formula: C8H16O2
• Molecular Weight: 144.214
• Hs Code.: 2915.90
• European Community (EC) Number: 205-743-6
• ICSC Number: 0477
• NSC Number: 8881
• UN Number: 1993
• UNII: 01MU2J7VVZ
• DSSTox Substance ID: DTXSID9025293
• Nikkaji Number: J36.965I
• Wikipedia: 2-Ethylhexanoic_acid
• Wikidata: Q209384
• Metabolomics Workbench ID: 157
• ChEMBL ID: CHEMBL1162485
• Mol file: 149-57-5.mol

Synonyms:2-ethylhexanoic acid;Sinesto B

Chemical Property of 2-Ethylhexanoic acid

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: -59 °C
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 228 °C at 760 mmHg
• PKA: pK1:4.895 (25°C)
• Flash Point: 116.6 °C
• PSA: 37.30000
• Density: 0.926 g/cm³
• LogP: 2.28740
• Storage Temp.: room temp
• Solubility.: 1.4g/l
• Water Solubility.: 2 g/L (20 ºC)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 144.115029749
• Heavy Atom Count: 10
• Complexity: 99.4

Purity/Quality:

99% ^*data from raw suppliers

2-Ethylhexanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-41-37/38-20/21/22
• Safety Statements: 36/37-36/37/39-26-2

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CCCCC(CC)C(=O)O
• Inhalation Risk: A harmful contamination of the air will be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Uses: Paint and varnish driers (metallic salts). Ethylhexoates of light metals are used to convert some mineral oils to greases. Its esters are used as plasticizers. 2-Ethylhexanoic acid is used in the preparation of metal derivatives, which act as a catalyst in polymerization reactions. For example, tin 2-ethylhexanoate is used in the manufacturing of poly(lactic-co-glycolic acid). It is also used as a stabilizer for polyvinyl chlorides. It is also involved in solvent extraction and dye granulation. Further, it is used to prepare plasticizers, lubricants, detergents, flotation aids, corrosion inhibitors and alkyd resins. In addition to this, it serves as a catalyst for polyurethane foaming. 2-Ethylhexanoic acid can be used: As a reactant in esterification , decarboxylative alkynylation , and preparation of alkyl coumarins via decarboxylative coupling reactions.In the organocatalytic medium for the preparation of various 3,4-dihydropyrimidin-2(1H)-ones/thiones by Biginelli reaction.

Technology Process of 2-Ethylhexanoic acid

There total 91 articles about 2-Ethylhexanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

d,l-2-ethylhexanal (123-05-7) → heptan-3-ol (589-82-2) + 2-Ethylhexanoic acid (149-57-5) + heptan-3-one (106-35-4)

Guidance literature:

With dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate; In water; at 90 ℃; for 2h;

DOI:10.1016/S0040-4039(99)02310-2

Reference yield: 61.0%

d,l-2-ethylhexanal (123-05-7) → heptan-3-ol (589-82-2) + 2-Ethylhexanoic acid (149-57-5) + heptan-3-yl formate (54009-71-1)

Guidance literature:

With oxygen; In n-heptane; at 25 ℃; for 0.29h; under 3750.38 Torr; Time; Concentration; Flow reactor;

DOI:10.1021/ol401273k

Reference yield: 36.0%

propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + d,l-2-ethylhexanal (123-05-7) → propylene glycol (57-55-6,63625-56-9) + 2-Ethylhexanoic acid (149-57-5)

Guidance literature:

With sulfuric acid; water; oxygen; In water; at 60 ℃; for 16h; under 2280.15 Torr; pH=1;

DOI:10.1039/b922475k

upstream raw materials:

peracetic acid

d,l-2-ethylhexanal

2-Ethylhexyl alcohol

2-ethylhexenal

Downstream raw materials:

2-ethyl-hexanoic acid-(3-tetrahydro[2]furyl-propyl ester)

1-(2-ethyl-hexanoyloxy)-2-(2,4-dichloro-phenoxy)-ethane

butyl 2-ethylhexanoate

(-)-3-Ethoxycarbonyl-heptan

Refernces

• 1、 Richardson. "". . p. 975,978. Retrieved 1966.
• 2、 Mannam, Sreedevi,Sekar, Govindasamy. "Efficient CuCl-catalyzed selective and direct oxidation of β- And γ-substituted aliphatic primary alcohols to carboxylic acids". . p. 2822 - 2829. Retrieved 2010.
• 3、 Vanoye, Laurent,Abdelaal, Mohamed,Grundhauser, Kacy,Guicheret, Boris,Fongarland, Pascal,De Bellefon, Claude,Favre-Réguillon, Alain. "Reinvestigation of the Organocatalyzed Aerobic Oxidation of Aldehydes to Acids". . p. 10134 - 10138. Retrieved 2019.
• 4、 Berkessel, Albrecht,Biswas, Animesh,Harnying, Wacharee,Sudkaow, Panyapon. "N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading". supporting information. p. 19631 - 19636. Retrieved 2021/08/09.
• 5、 -. "Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound". Paragraph 0172; 0175-0176; 0182; 0185-0186; 0192; 0195-0196. . Retrieved 2020/05/02.