816-19-3

Basic information

• Product Name: methyl 2-ethylhexanoate
• Synonyms: methyl 2-ethylhexanoate;2-Ethylhexanoic acid methyl ester;Ai3-33653;Einecs 212-429-2;Hexanoic acid, 2-ethyl-, methyl ester
• CAS NO: 816-19-3
• Molecular Formula: C₉H₁₈O₂
• Molecular Weight: 158.23802
• EINECS: 212-429-2
• Mol File: 816-19-3.mol

Chemical Properties

• Boiling Point: 176.5°C at 760 mmHg
• Flash Point: 59.4°C
• Appearance: /
• Density: 0.874g/cm³
• Vapor Pressure: 1.09mmHg at 25°C
• Refractive Index: 1.416
• Water Solubility: 202mg/L at 20℃
• CAS DataBase Reference: methyl 2-ethylhexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-ethylhexanoate(816-19-3)
• EPA Substance Registry System: methyl 2-ethylhexanoate(816-19-3)

Safety Data

• Hazardous Substances Data: 816-19-3(Hazardous Substances Data)

Usage

Flammability and Explosibility

Flammable

InChI:InChI=1/C9H18O2/c1-4-6-7-8(5-2)9(10)11-3/h8H,4-7H2,1-3H3

Upstream product

• 123-05-7 d,l-2-ethylhexanal 
• 149-57-5 2-Ethylhexanoic acid 
• 77-78-1 dimethyl sulfate 
• 90926-65-1 2-furfuryl-butyric acid methyl ester 
• 67-56-1 methanol 
• 592-76-7 1-Heptene 
• 7664-93-9 sulfuric acid 
• 14250-95-4 2-ethylhexanal dimethyl acetal 
• 616-38-6 carbonic acid dimethyl ester 
• 104-76-7 2-Ethylhexyl alcohol 
• 14686-13-6 (E)-hept-2-ene 
• 201230-82-2 carbon monoxide 
• 14686-14-7 trans-3-heptene 
• 760-67-8 2-ethylhexanoic acid chloride 

Downstream Products

• 41632-11-5 2-ethylhexanoic acid hydrazide 
• 26086-33-9 trimethylolpropane tri(2-ethyl hexanoate) 
• 67-56-1 methanol 
• 112-62-9 Methyl oleate 
• 112405-99-9 4-ethyl-1-phenyl-octane-1,3-dione 
• 63468-14-4 triethylene glycol 2-ethylhexanoate 
• 94-28-0 triethylene glycol bis(2-ethylhexanoate) 
• 31814-59-2 5,8-diethyl-7-hydroxydodecan-6-one 
• 57804-13-4 5,8-diethyl-dodecane-6,7-dione 
• 149-57-5 2-Ethylhexanoic acid 

Relevant articles and documents

METHOD FOR PREPARING HYDROXY OXIME

The present invention relates to a process for the preparation of hydroxy oximes. More particularly, the present invention relates to a method for preparing a hydroxy oxime capable of improving the yield of each process step and reducing the generation of ketoxime by-products which reduce the metal extractability of the hydroxy oxime as an extractant.

FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading

We report the discovery that simple carboxylic acids, such as benzoic acid, boost the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A simple and efficient protocol for the transformation of a wide range of sterically hindered α- and β-substituted aliphatic aldehydes/enals, catalyzed by a novel and readily accessible N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt, and benzoic acid as co-catalyst, was developed. A whole series of α/β-substituted aliphatic aldehydes/enals hitherto not amenable to NHC-catalyzed esterification could be reacted at typical catalyst loadings of 0.02–1.0 mol %. For benzaldehyde, even 0.005 mol % of NHC catalyst proved sufficient: the lowest value ever achieved in NHC catalysis. Preliminary studies point to carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates as the mechanistic basis of the observed effect.

SYNTHESIS OF TRIETHYLENE GLYCOL BIS(2-ETHYLHEXANOATE)

A process for the transesterification of methyl-2- ethylhexanoate with triethylene glycol to produce triethylene glycol di-2-ethylhexanoate is provided. In the process, methyl-2- ethylhexanoate is combined with triethylene glycol to form a first mixture. The first mixture is heated in the presence of a catalyst to form a second mixture comprising methanol and triethylene glycol di-2-ethylhexanoate. Methanol is separated from the second mixture to yield triethylene glycol di-2-ethylhexanoate. Na2CO3, CS2CO3, K2CO3, Rb2CO3, sodium methoxide or titanium isopropoxide are suitable catalysts.

ESTER SYNTHESIS USING HETEROGENEOUS AU/TIO2 CATALYST

A process for direct esterification of an alkyl aldehyde with an alkyl alcohol to produce an alkyl ester is disclosed. The process comprises reacting an alkyl aldehyde with an alkyl alcohol in the presence of an Au/TiOa catalyst, a base and an enal or oxygen to form an ester and an aldehyde. The process avoids liberation of water and avoids the step of oxidation of the alkyl aldehyde to an alkyl acid.

Iron-catalyzed selective production of methyl esters from aldehydes

A process for making methyl esters in high yields is provided. The process comprises contacting aliphatic or aromatic aldehydes and methanol with an iron catalyst, to catalyze the dehydrogenative coupling between aliphatic or aromatic aldehydes and methanol. The reaction is highly selective (99.9%) toward the formation of methyl esters over homoesters and alcohols and operates at temperatures of less than 100° C. for 2-8 hours.

Process for the production of esters

A process for making methyl esters in high yields. The process comprises contacting aliphatic or aromatic aldehydes and methanol with a homogeneous dimeric ruthenium catalyst, to catalyze the dehydrogenative coupling between aliphatic or aromatic aldehydes and methanol. The reaction is highly selective (99.9%) toward the formation of methyl esters over homoesters and alcohols and operates at temperatures of less than 100° C. for 2-8 hours.

Palladium/IzQO-Catalyzed coordination-insertion copolymerization of ethylene and 1,1-disubstituted ethylenes bearing a polar functional group

Coordination-insertion copolymerization of ethylene with 1,1-disubstituted ethylenes bearing a polar functional group, such as methyl methacrylate (MMA), is a long-standing challenge in catalytic polymerization. The major obstacle for this process is the huge difference in reactivity of ethylene versus 1,1-disubstituted ethylenes toward both coordination and insertion. Herein we report the copolymerization of ethylene and 1,1-disubstituted ethylenes by using an imidazo[1,5-a]quinolin-9-olate-1-ylidene-supported palladium catalyst. Various types of 1,1-disubstituted ethylenes were successfully incorporated into the polyethylene chain. In-depth characterization of the obtained copolymers and mechanistic inferences drawn from stoichiometric reactions of alkylpalladium complexes with methyl methacrylate and ethylene indicate that the copolymerization proceeds by the same coordination-insertion mechanism that has been postulated for ethylene.

The Pd-catalysed hydromethoxycarbonylation of aliphatic internal alkenes with minimal double bond isomerisation

The methoxycarbonylation of internal alkenes by a palladium(II)complex comprising PdCl2, bis(2-methoxyphenyl)phenylphosphine (2) and HCl has been investigated. The results presented herein demonstrate a non-isomerizing Pd-complex for the effective production of internal esters from the corresponding internal aliphatic alkenes. Selectivities of >70% were obtained for the desired internal esters with no signs of catalyst decomposition. The high selectivity for the internal esters is rationalized on the basis of the hemi-lability of the o-methoxy moiety which may assist in ligand dissociation. To the best of our knowledge this is one of the first reported hydromethoxycarbonylation routes to internal esters from their corresponding internal aliphatic alkenes.

Efficient flow fischer esterification of carboxylic acids with alcohols using sulfonic acid-functionalized silica as supported catalyst

Flow Fischer esterification of carboxylic acids using hydroxy-substituted sulfonic acid-functionalized silica (HOSAS) packed into a stainless steel column reactor was investigated. HO-SAS well catalyzed flow esterification of long chain carboxylic acids with methanol within 3min of residence time at 110°C, and the methyl esters were quantitatively obtained. The flow esterification protocol was applied to the synthesis of a variety of esters (19 examples) and scalable synthesis was also successful.