Levulinic acid ethyl ester

Ethyl levulinate Levulinic acid, ethyl ester (8) Pentanoic acid, 4-oxo-, ethyl ester (9) (539-88-8)... 

SYNS ETHYLKETOVALERATE ETHYL 4-KETOVALERATE ETHYL LAEVULINATE ETHYL LEVULATE ETHYL 4-OXOPENTANOATE ETHYL 4-OXOVALERATE LEVULINIC ACID, ETHYL ESTER... 

Its condensation product with levulinic acid ethyl ester (70) was marketed under the name kelevan (Gilbert et ai, 1965 Anderson and Nakakihara, 1968 Strong and Sbur, 1968). 

Synonyms Ethyl 3-acetylpropionate Ethyl ketovalerate Ethyl 4-ketovalerate Ethyl y-ketovalerate Ethyl laevulinate Ethyl levulate Ethyl-4-oxopentanoate Ethyl-4-oxovalerate Levulinic acid, ethyl ester 4-Oxopentanoic acid ethyi ester Pentanoic acid, 4-oxo-, ethyl ester Classification Nonaromatic ester Definition Ester of levulinic acid and ethyl alcohol Empirical C7H12O3 Formula CH3COCH2CH2COOC2H5... 

Levulinic acid, butyl ester. See Butyl levulinate Levulinic acid, ethyl ester. See Ethyl levulinate Levulose. See Fructose Lewisoi 28-M. See Glyceryl rosinate Lexaine CS. See Cocamidopropyl betaine Lexaine CSB-50. See Cocamidopropyl hydroxysultaine,... 

Ethyl levulinate (4-oxopentanoic acid ethyl ester)... 

Oxopentanoic acid ethyl ester. See Ethyl levulinate... 

Diesel (Cu-Cie) Fatty acid esters (methyl = FAME, ethyl = FAEE) Levulinic acid esters (methyl, ethyl) DME Ethanol Fischer-Tropsch diesel (from bio-based synthesis gas) Deoxygenated and refined primary bioliquids... 

Levulinic acid is fairly easily converted into thiazole derivatives by the intermediate formation of an a-halogenated ketone such as the /3-bromo derivative (XL) or /3-chloro derivative, which reacts with thiourea to form 2-amino-4-methyl-5-thiazoleacetic acid (XLI) or with thioformamide to give 4-methyl-5-thiazoleacetic acid (XLII). The aminothiazole (XLI) and its ethyl ester (XLIII) have been converted into their corresponding sulfanilamide derivatives, (XLIV) and (XLV). These sulfanilamides, particularly the acid XLIV, have considerable chemotherapeutic activity moreover the acid possesses distinct solubility advantages over sulfathiazole itself. 

The introduction of the trimethylsilyl chloride trapping technique" led to improved yields in the case of simple aliphatic esters. The initial silylated products are easily isolated and can be converted into the acyloins simply and in high yield. For simple aliphatic esters the yields are in the range 56-92%. Use of trimethylsilyl esters, rather than simple alkyl esters, leads to faster reactions, but lower yields.Substituted esters which have been successfully used in the newer procedure include ethyl 2-ethylhexanoate (83%), ethyl trimethylsilylacetate (90%)," ethyl 3-trimethylsilylpropionate (65%)," ethyl phenylacetate (48%)," ethyl 3-phenylpropionate (79%)" and 2-(2-methoxycarbonylethyl)-2-methyl-l,3-dioxolane derived from levulinic acid (65%)." In the case of ethyl adamantane-l-carboxylate the yield using the newer procedure is reported to be inferior to that using the earlier procedure. 

Esterification, crotonic acid, 149 levulinic acid, 157 thiophene-2-carboxylic acid, 182 o-toluic acid, 162 Ester interchange, 152 Ethanolysis of ethyl iminoacetate, 159 Ether cleavage with HBr, 271... 

Levulinic acid is known to react with aldehydes at carbon atoms adjacent to both the acid (a) and keto (P and 8) groups to form a mixture of the a-, P-, and 8- alkylidene or arylidene derivatives 11,12), With excess formaldehyde, levulinic acid is substituted with five or six hydroxymethyl (methylol) groups, and cyclization to a lactone occurred 18), These condensation reactions could be utilized to produce inexpensive resins from the crude ethyl levulinate obtained from waste particle board without distillation. Another reason for studying the reactions of the ester with aldehydes is to determine the potential for similar reactions occurring during the cellulose... 

The reaction of ethyl levulinate with furfural gave a condensation product, of which the major isomer is presumed to be the 8-furfurylidenelevulinate ester, since the acid-catalyzed reaction of furfural with levulinic acid produces this isomer 19). Some of this reaction could occur during the preparation of ethyl levulinate, since furfural and acid catalyst are present, but no furfurylidenelevulinate ester was detected in the ether extract. Thus, if condensation reactions occur, the products stay in the char or the resin products and are likely of higher molecular weight. 

It is industrially produced by the acid-catalysed hydrolysis of carbohydrates such as cellulose or starch. The global production of levulinic aid is very small (<3,000 t/a), the acid is used as a solvent in the ethyl ester form and in small niche markets [16]. 

Reactions with functionalized alkyl halides significantly enhance the range of application of alkyl [ C]acetoacetates. Alkylation of ethyl [3- C]acetoacetate with halo esters, for example, followed by acid-mediated ketonic cleavage opens access to labeled keto acids/esters, as demonstrated by the synthesis of the [4- C]levulinic acid (307) a y-keto acid. The latter has served as a key intermediate in the synthesis of the 2,3-substituted indole 308 . Step 2 in Figure 6.85, the ketonic cleavage, has recently been shown to be accelerated by a factor of 20 when the reaction is submitted to microwave heating. ... 

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