Methyl -4-decenoate

Methyl 2-Methylheptanoate Methyl Phenyl acetate Methyl B-Phenylproprionate Methyl Nonanoate Methyl Decenoate p-Methoxy Acetophenone Methyl Anthranilate Methyl 3-Methoxybenzoate Methyl 4-Methoxyphenylacetate... 

Most current studies of biodiesel chemistry, and the detailed chemical kinetic mechanisms derived therefrom, are based on surrogate molecules and mixtures the proxies contain the same or similar chemical functionalities as actual fuels, but are simplified systems designed to isolate particular aspects of the chemistry or behavior. Biodiesels in current use are alkyl esters of saturated and unsaturated fatty acids, with hpid chain lengths that range from about C14 to C22 (most typically C16 to C18), with the chemical composition varying from oil to oil. The surrogates used in the models are often smaller saturated and unsaturated lipids such as MB (and methyl butenoate), methyl hexanoate, or MD (and methyl decenoate). 

It has been shown that halogen-substituted alkenes can participate in the metathesis reaction, e.g. 5-bromo-l-pentene reacts with 2-pentene 11). A very interesting reaction is the conversion of methyl-9-octa-decenoate into 9-octadecene and dimethyl-9-octadecenedioate 12) ... 

Decenoic acid (143), easily prepared from the same telomer 142, was cyclized via acid chloride using A1C13 to give 2-pentyl-2-cyclopentenone (144). Michael addition of methyl malonate followed by removal of one ester group produced methyl dihydrojasmonate (145) (129) ... 

Polymers Catalytic reactions involving C=C bonds are widely used for the conversion of unsaturated fatty compounds to prepare useful monomers for polymer synthesis. Catalytic C-C coupling reactions of unsaturated fatty compounds have been reviewed by Biermann and Metzger [51]. Metathesis reactions involving unsaturated fatty compounds to prepare co-unsaturated fatty acid esters have been applied by Warwel et al. [52], Ethenolysis of methyl oleate catalyzed by ruthenium carbenes developed by Grubb yields 1-decene and methyl 9-decenoate (Scheme 3.6), which can be very useful to prepare monomers for polyolefins, polyesters, polyethers and polyamide such as Nylon 11. 

Recently, a patent described the use of Diplodia gossypina ATCC 10936 for the production of natural jasmonic acid [47]. With submerged cultures, up to 1.5 g L" jasmonic acid was obtained after 11 days of incubation the addition of 10-oxo-8-fra s-decenoic acid, a hormone stimulating mycelial growth, proved to be advantageous methyl jasmonate was obtained by autoclaving the... 

The gross structural features, presence of a tetramic acid and E-decenoyl side chain, could be inferred from NMR studies. Methanolysis (HCl/MeOH) of 47 and pentane extraction of the quenched reaction mixture gave two compounds that were determined to be the methyl esters of decenoic acid and N-(2-decenoyl)leucine. The nature of the 3-acyl tetramic acid was deduced from the identification of 48 and 49 in the aqueous portion of the methanolysis reaction mixture following treatment with trifluoroacetic acid anhydride. The unusual C-C bond fragmentation under acidic conditions, and the structure of the antibiotic was confirmed by synthesis of racemic 47 [86]. The configuration at the lone chiral centre was established as R by chiral GC. The carbon NMR spectrum of 47 indicated an equilibrium between three tautomers in which the A2-pyrrolin-4-one form is preferred (60%) and the two internal tautomers (50, 51) make equal contributions (20% each). 

Cl OH1802 9-decenoic acid 14436-32-9 540.00 47.740 2 20860 C10H19Br 1-bromo-4-methyl-1-isopropylcyclohexane 116836-10-3 498.15 43.706 2... 

To elucidate the mechanism of homogeneous hydrogenation catalyzed by Fe(CO)s, kinetic studies were carried out with mixtures of unsaturated fatty esters containing a radioactive label. A C-labeled methyl octadecadienoate-Fe(CO)3 complex was prepared to serve as a catalytic intermediate. Hydrogenation of methyl oleate (m-9-octa-decenoate) and palmitoleate (cis-9-hexadecenoate) and of their mixtures with methyl linoleate was also studied to determine the selectivity of this system, the function of the diene-Fe(CO)3 complex, and the mechanism of homogeneous isomerization. Mixtures of reaction intermediates with a label helped achieve unique simulation of the kinetic data with an analog computer. 

From the industrial point of view the co-metathesis of unsaturated fatty compounds, especially methyl oleate, with ethylene to form methyl 9-decenoate and 1-decene is becoming more important (eq. (3)). 

Figure 5.4 GC-MS total ion current (TIC) chromatogram of a red Italian wine (Corvina) after HS- SPME automated aroma enrichment using a 1 cm CAR-PDMS-DVB fiber. 1. ethyl acetate, 2. ethanol, 3. isobutyl alcohol, 4. isoamyl acetate, 5. isoamyl alcohols, 6. ethyl hexanoate, 7. methyl heptanoate (I.S.), 8. linalyl ethylether, 9. 1-hexanol, 10. ethyl octanoate, 11. acetic acid, 12. geranyl ethylether, 13. linalool, 14. ethyl decanoate, 15. diethylsuccinate, 16. ethyl 9-decenoate, 17. 2-phenethyl acetate, 18. hexanoic acid, 19. 2-phenylethanol, 20. octanoic acid, 21. decanoic acid...

The hydroformylation of co-alkene carboxylic acid methyl esters catalysed by a Rh/TPPTS system (Scheme 1.22) in a biphasic medium does not require additives with low molecular substrates such as methyl 4-pentenoate, whereas methyl esters of higher co-alkene carboxylic acids such as methyl 13-tetra-decenoate require the presence of surfactants as mass-transfer promoters. Surfactants, indeed, decrease the interfacial tension, forming aggregates above the critical micellar concentration that speed up the catalytic process by increasing the interfacial area. 

The reaction is highly influenced by the solvent therefore among others NMP, DMF, dioxane, methyl formamide, dimethyl acetamide and tetramethyl urea were tested. The best results were achieved in DMF and tetramethyl urea. Using these solvents and PdCl2/CuCl or RhCl3/FeCl3 [27] as catalysts, oxidations of 10-undecenoic acid methylester, 9-decenoic acid methylester and 13-tetradecenoic acid methylester were carried out on a preparative scale (Table 2). 

The synthesis of carboxylated perfluorovinyl ether was very difficult and no preparative method had been known before. Recently, however, several synthetic methods have been proposed. An example of the synthetic route to methyl perfluoro-5-oxa-6-heptenoate (M ) and methyl perfluoro-5,8-dioxa-6-methyl-9-decenoate (M2) is shown in the following scheme. 

Metathesis has been applied in oleochemistry for many years, but only fairly recently technical realization comes within reach [33, 34]. As typical catalysts, ruthenium carbene complexes of the Grubbs type are applied because of their very high activity (turnover numbers up to 200 000). In principle, oleochemical metathesis can be divided into two different types in self-metathesis the same fatty substrate reacts with itself and in cross-metathesis a fatty substrate reacts with, for example, a petrochemical alkene. The simplest case, the self-metathesis of methyl oleate forms 9-octadecene and dimethyl 9-octadecenedioate. The resulting diester can be used along with diols for the production of special, comparatively hydrophobic, polyesters. An interesting example of cross-metathesis is the reaction of methyl oleate with an excess of ethene, so-called ethenolysis. This provides two produds, each with a terminal double bond, 1-decene and methyl 9-decenoate (Scheme 3.3). 

The best results in terms of activity have been obtained with cationic surfactants such as octadecyltrimethylammonium bromide. The normal to branched (njiso) aldehydes ratio was found to be very dependent on the nature of the surfactant. For example, methyl 9-decenoate hydroformylation gave methyl 11-formylunde-canoate with an n/iso aldehydes ratio of 6.1 1, 4.0 1, 2.3 1 and with anionic, amphophilic, and cationic surfactants, respectively. Interestingly, hydroformylation of this substrate has also been achieved successfully with inverse-phase transfer catalysts such as chemically modified /l-cyclodcxtrins. In this approach, the cyclodextrin forms an inclusion complex with methyl 9-decenoate and transfers the alkene into the aqueous phase. Under optimal conditions, the aldehydes are obtained in a 100% yield and in an n/iso aldehydes ratio of 2.3 1 [10]. 

The accelerating influence of water as a solvent on the rate of the Claisen rearrangement was demonstrated by the rearrangement of sodium 8-vinyloxy-9-decenoate at 60 °C, giving rise to a 85 % yield of sodium (E)- 2-oxo-8-dodecenoate (11 a)146. The methyl ester lib was obtained in nearly equal yield despite the heterogeneous medium. 

Ethenolysis of unsaturated esters results in the synthesis of shorter-chain w-unsaturated esters, compounds with a broad range of application. Excess ethene can easily be used (e. g. by use of ethene pressures of 30-50 bar) to suppress self-metathesis of the ester and to force the conversion to completion. Ethenolysis of methyl oleate produces methyl 9-decenoate and 1-decene (Eq. 13) [37,38]. High conversion of methyl oleate can be obtained at room temperature by use of a Re207 catalyst promoted with tetraalkyltin. 

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