Oleic acid methyl ester

Egg yolk TMAH Palmitic and oleic acid methyl esters 73... 

Calcium caseinate TMAH Pyrrole <50%, palmitic and oleic acid methyl esters <60% 1... 

Figure 12.12 THM GC/MS curves of a Winsor Newton lemon alkyd paint (a) and of an alkyd sample taken from Fontana s work Concetto spaziale (1961) (b). Peak assignments 1, 1,3 dimethoxy 2 propanol 2, 1,2,3 trimethoxy propane 3, 3 methoxy 1,2 propandiol 4, 4 chloro benzenamine 5, 3 methoxy 2,2 bis(methoxymethyl) 1 propanol 6, 3 chloro N methyl benzenamine 7, 3 methoxy 2 methoxymethyl 1 propanol 8, 4 chloro N methyl benzenamine 9, phthalic anhydride 10, 3 chloro 4 methoxy benzenamine 11, suberic acid dimethyl ester 12, dimethyl phthalate 13, azelaic acid dimethyl ester 14, sebacic acid dimethyl ester 15, palmitic acid methyl ester 16, oleic acid methyl ester 17, stearic acid methyl ester 18, 12 hydroxy stearic acid methyl ester 19, 12 methoxy stearic acid methyl ester 20, styrene 21, 2 (2 methoxyethoxy) ethanol 22, 1,1 oxybis(2 methoxy ethane) 23, benzoic acid methyl ester 24, adipic acid dimethyl ester 25, hexadecenoic acid methyl ester 26, dihydroisopimaric acid methyl ester 27, dehydroabietic acid methyl ester 28, 4 epidehydroabietol...

Acetic acid, butyl ester Acetic acid, pentyl ester Acetic acid, decyl ester Acetic acid, benzyl ester Acetic acid, benzyl ester Acetic acid, 1-cyclohexenyl ester Acetic acid, 3-cyclohexenyl ester Butyric acid, benzyl ester Phenylacetic acid, propyl ester Oleic acid, methyl ester Linoleic acid, methyl ester Linolenic acid, methyl ester Adipic acid, methyl ester Adipic acid, ethyl ester Adipic acid, diethyl ester Adipic acid, dipropyl ester Adipic acid, (methylethyl)ester Adipic acid,... 

Oleic acid methyl ester Call Tiss ° ... 

I Average conversion yield Linolenic acid methyl ester Linoleic acid methyl ester Oleic acid methyl ester... 

Fig. 6. Effect of molar ratio of methanol to oleic acid on yield of oleic acid methyl esters at 270°C for 20 min. The dashed line (—) represents data in transesterification from ref.23.

In view of the technical implementation of hydroesterification of oleic acid methyl esters, these disadvantages have to be avoided. 

The hydroesterification of oleic acid methyl ester was first described by Reppe [60]. He showed with the precursor Ni(CO)4 at a reaction temperature of 280°C and a carbon monoxide pressure of pco = 200 bar a 36% yield of the hydroesterification product after 16 h. 

The palladium-catalyzed hydroesterification of oleic acid methyl esters was investigated by Frankel and was conducted at lower reaction temperatures in comparison to the nickel catalysis [61]. For example, the hydroesterification of oleic acid methyl ester and methanol with PdCl2 and PPh3 was achieved at a pressure of 270 bar. A 62% yield of the hydroesterification product was achieved after 12 h. The new C-C bond was formed mostly at positions 9 and 10 of the carbon chain. Approximately 10% of the hydroesterification products were observed at positions Cg and Cn to Ci3, which could be attributed to isomerization of the double bond during the reaction. 

Operation of the Biodiesel Cost Optimizer is fast and easy, making it possible to make large sets of simulations in a short time. This helps better understanding the different value of the different fatty acid methyl esters. It will quickly become clear, when using the Biodiesel Cost Optimizer, that oleic acid methyl esters are the preferential FAME in every biodiesel formula. Oleic acid methyl esters bring a relatively high oxidation stability (50h or more), combined with a more than acceptable CN of around 56, and excellent melting point at -19 °C. Unfortunately, pure oleic acid methyl esters are not available in the market. 

Figure 2.2. FTIR (upper) transmission and Raman scattering (lower) of oleic acid methyl ester.

Synonyms (Z)-9-Octadecenoic acid methyl ester Oleic acid methyl ester Source Nilsson, W. B. Gauglitz, E. J. Jr. Hudson, J. K. J. Am. OilChem. Soc. (1991), 68(2), 87-91. 

Johnson-Matthey Co. has reported that oleic acid methyl ester or linoleic acid methyl ester can be hydroformylated in micellar media using a water-soluble rhodium complex of monocarboxylated triphenylphosphine 45 as catalyst. As a further example, polyunsaturated linolenic acid methyl ester can be hydroformylated to the triformyl derivative with a selectivity of 55% with a Rh/TPPTS catalytic system in the presence of CTAB (Scheme 1.23). ... 

Fig. 2. Chemical structures of typical slick-forming compounds, a.) oleyl alcohol (Z-9-octadecen-l-ol OLA), b.) oleic acid methyl ester (methyl Z-9-octadecenoate OLME), and c.) methyl palmitate (methyl hexadecanoate PME)...

Fig. 4. Spreading velocities [cm/s] in dependence on the distance from the source [cm] for pure oleyl alcohol (OLA top), a 75 mmol solution of OLA in ethanol (OLA/ethanol middle), and pure oleic acid methyl ester (OLME bottom) note the different ordinate scales...

Figure 10.4 Phase diagrams of the systems h O/NaCI-rape oleic acid methyl ester/suet-Lutensol AP9 at <(> = 0.50 and e = 0.10. The parameter 0 corresponds to the mass fraction of suet in the mixture of suet and rape oleic acid methyl ester. With increasing 0, the phase behaviour is shifted to higher temperatures and surfactant mass fractions. Because of the dominance of the Lc,-phase a phase diagram at 0 = 1.00 could not be obtained.

C and fatty alcohols when working at 180 °C. Starting from oleic acid methyl ester, yields of up to 84% were obtained. Conversions of oleochemical feedstocks with Rh catalysts were possible, too [45]. 

The fatty acid methyl ester contents in the reaction mixture were determined using a Donam 6100 GC gas chromatograph (Donam, South Korea) equipped with an HP-INNOWAX capillary column (30m x 0.32imn x 0.5 pm) and an flame ionization detector. The column oven temperature was maintained at 210 °C for analysis. The injector and detector temperatures were set to 250 and 250 °C, respectively. Helium was utilized as a carrier gas. The gas chromatography calibration was conducted via the analysis of standard solutions of palmitic acid methyl ester, stearic acid methyl ester, oleic acid methyl ester, linoleic acid methyl ester, linolenic acid methyl ester, and erucic acid methyl ester. The internal standard was diluted in pyridine, as were the reaction mixture samples. The conversion was expressed as the percentage of fatty acid methyl esters generated relative to the theoretical maximiun quantity, based on the amount of original oils. In this paper, the conversion was expressed as the fatty acid methyl ester content or in accordance with conversion. 

The in situ procedure as proposed by Sonnet et al. (18) is much more attractive for synthetic applications. With the use of only a moderate excess of monopersulfate (C=C KHSO5 = l 2-2.4), they achieved an 80% yield for the epoxidation of oleic acid methyl ester and 81-96% for the epoxidation of various plant oils. It is a twophase reaction with a crown-ether as phase-transfer catalyst yet a considerable amount of inorganic waste (six times the weight of the product) is produced. In a recent work (21), the phase-transfer catalyst was replaced by acetonitrile as a polar solvent. In summary, epoxidation by dioxiranes is a promising new method for oleo-chemistry, especially because it also works in combination with metal catalysts to influence diastereoselectivity (22) an enantioselective epoxidation with sugardioxiranes has also been reported (23). 

A very similar reaction catalyzed by M0O3 or Mo02(acac)2 has been disclosed by Degussa AG (42). CH3Re03 is also capable of catalyzing vicinal hydroxylation oleic acid methyl ester (31) and high-oleic sunflower oil (32) were hydroxylated with... 

Fig. 17. Molybdenum-catalyzed methoxyhydroxylation of oleic acid methyl ester by ferf-butyl hydroperoxide.

The two-step-process via metathesis of oleic acid methyl ester with ethylene, yielding 9-decenoic acid methyl ester and 1-decene (65,66), has the advantage that the production of the two products of direct cleavage can be decoupled. 1-Decene will be submitted to Oxidative cleavage only if there is a market for pelargonic acid. Be-... 

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