Methyl decanoate oxidation

Glaude, P.A., Herbinet, O., Bax, S., Biet, J., Warth, V., Battin-Leclerc, F. Modeling of the oxidation of methyl esters-Validation for methyl hexanoate, methyl heptanoate, and methyl decanoate in a jet-stirred reactor. Combust. Flame 157, 2035-2050 (2010)... 

Even larger esters have been considered. Herbinet et al. in 2008 developed an oxidation mechanism for methyl decanoate (MD) oxidation, by combining models for n-alkanes and MB, and then adding additional reactions specific to MD. This model was compared with results from engine experiments and a JSR. That same year, Seshadri et al. " looked at extinction and ignition of MD in laminar nonpremixed flows and used a skeletal version of the Herbinet et al. model to simulate the results. In... 

Phytanic acid, the product of chlorophyll that causes problems for individuals with Refsum s disease, is 3,7,11,15-tetramethyl hexa-decanoic acid. Suggest a route for its oxidation that is consistent with what you have learned in this chapter. Hint The methyl group at C-3 effectively blocks hydroxylation and normal /3-oxidation. You may wish to initiate breakdown in some other way.)... 

The relative reactivity of primary and secondary positions adjacent to oxygen can be strongly dependent on the nature of the oxidant. For example, treatment of the methyl ethers (8) and (10) with chromium trioxide in acetic acid leads to the formation of the formates (9) and (11), respectively (equations 13 and 14). In direct contrast, n-decyl methyl ether is oxidized exclusively to methyl n-decanoate (83% yield) by ruthenium tetroxide (equation 11). Under similar reaction conations, 3 -cholestanol methyl ether gives cholestan-3-one as the mqjor product, togedier with traces of the corresponding formate. Therefore, at least in the case of ruthenium tetroxide, primary positions appear to be more reactive than tertiary. 

Myristic acid occurs naturally in nutmeg butter and in most animal and vegetables fats. Synthetically, it may be prepared by electrolysis of methyl hydrogen adipate and decanoic acid or by Maurer oxidation of myristyl alcohol. 

Linear unsaturated and epoxidized polyesters via enzymatic polymerization were reported as well [58]. For this long-chain symmetrically unsaturated a,co-dicarboxylic acid dimethyl esters (C18, C20, C26) were synthesized using metathesis techniques from 9-decanoic, 10-undecanoic, and 13-tetradecanoic acid methyl esters, respectively. The dicarboxylic acid dimethyl esters were epoxidized via chemoenzymatic oxidation with hydrogen peroxide/methyl acetate and Novozym... 

The diversity associated with silyl protecting groups as well as the chemical conditions available for their removal makes them attractive alternatives to benzyl protection of the hydroxy groups of either D- or L-tartaric acid derivatives. O-isopropylidene-L-threitol (37) is mono-protected with er -butyldimethylsilyl chloride to furnish 266, which is converted in three steps to the nitrile 267. Reduction with DIBAL and Wittig olefination followed by desilylation with fluoride and Swern oxidation of the resulting alcohol provides aldehyde 268, which reacts with methyl 10-(triphenylphosphorane)-9-oxo-decanoate (269) to afford enone 270. Reduction of 270 with subsequent preparative TLC and acetal hydrolysis furnishes (9R)-271 and (9 S)-272, both interesting unsaturated trihydroxy Cig fatty acid metabolites isolated from vegetables [91] (Scheme 62). 

Acenaphthene n-Amyl alcohol Arachidic acid Arachidyl alcohol Benzidine dihydrochloride 2-Butyl octanoic acid Butyloctanol Calcium sulfate Cetylarachidol Cocamine Cocopropylenediamine Cyclodextrin p-Cyclodextrin 1,10-Decanediol 2-Decyl tetradecanoic acid Dihydroxyethyl cocamine oxide Dodecylhexadecanol 2-Hexyl decanoic acid Hydroxypropyl-o-cyclodextrin Hydroxypropyl-P-cyclodextrin Hydroxypropyl-y-cyclodextrin 12-Hydroxystearyl alcohol Isobutyl oleate Kelp Lead phthalate, basic Methoxyethanol 2-Methoxy-5-nitroaniline Methoxy tripropylene glycol acrylate Methylene chloride 2-Octyl dodecanoic acid Oleamine PEG-25 castor oil PEG-30 castor oil PEG-36 castor oil PEG-40 castor oil PEG-200 castor oil PEG-5 hydrogenated castor oil PEG-25 hydrogenated castor oil Polyamide Polysorbate 85 Pyridine Quartz Sodium isopropyl naphthalene sulfonate Soybean (Glycine soja) meal Sucrose Sulfur Tallow amine N-Tallow-1,3-diaminopropane dioleate p-Toluene sulfonic acid Tri methyl amine Tungstic acid Undecylenic acid Vinyl compounds and polymers plastics additive... 

Volatile fatty acids p resent in wine may derive from the anabolism of lipids, resulting in compounds with even number of carbon atoms, by oxidative decarboxylation of a-keto acids or by the oxidation of aldehydes. Volatile fatty acids synthesised from a-keto acids are mainly propanoic add, 2-methyl-l-propanoic acid (isobutyric acid), 2-methyl-l-butanoic acid, 3-methyl-l-butanoic acid (isovaleric acid 3-methylbutyric add) and phenylacetic add. From lipid metabolism, the following fatty acids are reported butanoic add (butyric), hexanoic acid (caproic), odanoic acid (caprylic) and decanoic add (capric) (Dubois, 1994). Although fatty adds are charaderized by unpleasant notes (Table 1), only few compounds of this family attain its perception threshold. However, their flavour is essential to the aromatic equilibrium of wines (Etievant, 1991). 

Selected data from Lambelet etal. (2003). Fatty acid composition of refined low-erucic rapeseed oil (also known as canola oiI)(%) C16 0,4.7 CI8 0,1.7 CI8 I,6I.7 C18 2,20.0 CI8 3,8.3 C20 1,1.3 other, 2.3. Oxyphytosterols include oxides of brassicasterol, campesterol and sitosterol. Cyclic monomers include cis and trans methyl 9-(2-butyIcycIopentyI)nonanoate and cis and trans methyl I0-(2-propylcyclopentyl) decanoate, cis methyl I0-(2-propyIcycIopentenyI) decanoate, and cis methyI9-(2-propylcyclohexyl) nonanoate. 

---